Secondary metabolites from Rubiaceae species.

This study describes some characteristics of the Rubiaceae family pertaining to the occurrence and distribution of secondary metabolites in the main genera of this family. It reports the review of phytochemical studies addressing all species of Rubiaceae, published between 1990 and 2014. Iridoids, anthraquinones, triterpenes, indole alkaloids as well as other varying alkaloid subclasses, have shown to be the most common. These compounds have been mostly isolated from the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. The occurrence and distribution of iridoids, alkaloids and anthraquinones point out their chemotaxonomic correlation among tribes and subfamilies. From an evolutionary point of view, Rubioideae is the most ancient subfamily, followed by Ixoroideae and finally Cinchonoideae. The chemical biosynthetic pathway, which is not so specific in Rubioideae, can explain this and large amounts of both iridoids and indole alkaloids are produced. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it produces indole alkaloids together with other alkaloids. The chemical biosynthetic pathway now supports this botanical conclusion.

1. Introduction

The Rubiaceae family is characterized by the production of bioactive metabolites with great pharmacological potential. These metabolites can be used as chemotaxonomic markers even for genera and subfamilies [1,2]. Usually, taxa are classified according to different botanical characteristics; classical taxonomic systems only consider the plant morphological characters, while modern systems correlate their various combinations, including the chemical composition. Studies correlating classical plant taxonomy to chemical data can be found as far back as 1699 [3].

Phytochemical compounds can be a useful tool for characterizing, describing and classifying plant species. The distribution of secondary metabolites in Rubiaceae follows patterns that may help characterize the botanical group (subfamily, tribe or genera). These patterns relative to chemotaxonomy are often used to establish the botanical origin [4].

In recent years, Rubiaceae species have been thoroughly studied from a phytochemical viewpoint. However, very few studies have used this knowledge as a tool in taxonomic studies. When conducting bioprospecting studies of a plant, all botanical and chemotaxonomic information is of great importance, since it increases the likelihood of finding bioactive compounds, which enables the discovery of new Nature-originated drugs [5]. Therefore, the present study aims to conduct a literature survey on phytochemical studies addressing species of Rubiaceae published from 1990 to 2014, and describe their secondary metabolites occurrence and distribution in the subfamilies, tribes and main genera of this family.

2. Taxonomic Classification of Rubiaceae

The Rubiaceae family has a cosmopolitan distribution, mostly concentrated in the tropics. Being one of the largest in the Magnoliopsida class, it ranks fourth in diversity of species among Angiosperms [4]. It includes approximately 637 genera and 13,000 species [5,6]. In Brazil, nearly 120 genera and 1400 species occur, representing one of the most important economic, ornamental and medicinal plant families in the Brazilian flora [7].

The Rubiaceae family taxonomic classification is complex and there are still some gaps which have to be filled. According to the classification of Robbrecht [8], the Rubiaceae family is divided into four subfamilies: Rubioideae, Cinchonoideae, Antirheoideae and Ixoroideae. However, more recent studies suggest this family to be divided into three subfamilies: Rubioideae, Cinchonoideae and Ixoroideae, as some authors do not recognize Antirheoideae as a subfamily, since molecular studies have shown it to be polyphyletic with no standardized occurrence of a chemical marker [9,10,11,12,13,14,15,16]. Due to the abundance of species, the subfamilies were divided into 43 tribes (an intermediate clade between genus and subfamily) [16], which are listed in Figure 1.

Figure 1

Subfamilies and tribes belonging to the Rubiaceae family [16].

Due to the lack of studies that can complement the extant information on geographical distribution, morpho-anatomical characteristics and molecular data, there are still genera and species not allocated into any tribe [16]. The evaluation of the chemical profile of these species may indicate a more complete phylogenetic distribution, since the secondary metabolites are the results of adaptation and evolution of a specific taxon to environment [17]. Thus, the profile of secondary metabolites distribution can bring new information for the taxonomic classification of this family.

3. Chemical and Biological Aspects of Rubiaceae

The Rubiaceae family presents a large diversity of substances such as iridoids, indole alkaloids, anthraquinones, terpenoids (diterpenes and triterpenes), flavonoids and other phenolic derivatives, with emphasis on production of bioactive alkaloids [2]. Alkaloids are secondary metabolites that can generate various drugs with important pharmacological effects and used to find out physiological responses and biochemical mechanisms of action [18].

The number of described products, the structural diversity and pharmacological activities reported for various species of Rubiaceae demonstrate this family to be a promising source of new bioactive substances, which may give rise to new products as active molecules or even drug prototypes. Many of these plants have widespread use in folk medicine and some showed anti-inflammatory, analgesic, antibacterial, mutagenic, antiviral, antioxidant, effect on vascular diseases as well as activity on the central nervous system [19].

In the Ixoroideae subfamily, the genus Coffea is one of the most economically important, mainly the species Coffea arabica, popularly known as coffee, which has caffeine as one of its principal chemical components. This substance acts as stimulant of the central nervous system, as well as vasoconstrictor, bronchodilator and diuretic, besides being one of the components of migraine drugs [18]. Genipa, the Brazilian jenipapo (Genipa americana) with antiangiogenic, anti-inflammatory and antioxidant activity [20,21,22] is another important genus from which genipin was isolated, a colorless iridoid, used by indigenous people to tattoo their skin, since it produces a black coloration when it reacts with skin proteins. Its fruits are used to make wines, liqueurs, jams, soft drinks, etc. [23].

In the Cinchonoideae subfamily, Cinchona species are the source of quinine, isolated in 1820 by Pelletier and Caventou [24], and which for about 200 years was the only active substance against malaria, and can be considered as responsible for the development of synthetic antimalarials [1,25]. More than 50 new substances were isolated from alkaloid-rich Uncaria species [19], as Uncaria tomentosa, known as “unha de gato”, is one of most used plants in Brazilian folk medicine. Studies have shown that alkaloids isolated from this plant have immunostimulant and antitumor activity [26,27]. Other groups of substances such as triterpenes and procyanidins presented anti-inflammatory activity [28,29].

Psychotria, belonging to the Rubioideae subfamily, are plants that produce substances with activity on the central nervous system, such as Psychotria viridis, popularly known as “ayahuasca” which means “soul wine”. P. viridis is used in religious ceremonies in association with Banisteriopsis caapi, a species from the Malpighiaceae family [30,31]. Their hallucinogenic effect is due to the synergy that occurs between the alkaloid N,N-dimethyltryptamine (DMT), present in the leaves of P. viridis, and β-carboline indole alkaloids (harmine, harmaline and tetrahydroharmine) present in the bark of B. caapi [32]. Cephaelis is another important genus, especially C. ipecacuanha, a plant traditionally used by the Brazilian population, an important source of emetine, an alkaloid with emetic, antihelminthic and expectorant effects [33,34]. In Brazil, species of Palicourea are considered responsible for about half of all cattle deaths brought about by natural poisoning [35]. Some selected isolated compounds from Rubiaceae species are shown in Table 1 and Figure 2.

Table 1

Some metabolites isolated from Rubiaceae.

Genera	Class	Substance	Structure *
Cephaelis	Alkaloid	Emetine	I
	Lactone	Chelidonic acid	II
	Alkaloid	Cephalin	III
	Alkaloid	Psycotrin	IV
Cinchona	Alkaloid	Quinine	V
	Triterpene	Cincholic acid	VI
	Triterpene	Quinovic acid	VII
	Alkaloid	Quinidine	VIII
	Alkaloid	Cinchonine	IX
	Alkaloid	Cinchonidine	X
Coffea	Methyl xantine	Caffeine	XI
	Diterpene	Cafestol	XII
	Anthraquinone	Galiosin	XIII
	Anthraquinone	Copareolatin	XIV
	Anthraquinone	Munjistin	XV
Corynanthe	Alkaloid	Yohimbine	XVI
Galium	Iridoide	Macedonine	XVII
Genipa	Monoterpene	Genipin	XVIII
Hedyotis	Anthraquinone	Alizarin	XIX
Landerbergia	Alkaloid	Quinidine	VIII
	Alkaloid	Cinchonine	IX
	Alkaloid	Cinchonidine	X
Morinda	Anthraquinone	Alizarin	XIX
Mussaenda	Triterpene	Arjunolic acid	XX
Oldenlandia	Anthraquinone	Alizarin	XIX
Psychotria	Alkaloid	Psycotrin	IV
	Alkaloid	Cephalin	III
Relbunium	Anthraquinone	Purpurin	XXI
Remijia	Alkaloid	Quinidine	VIII
	Alkaloid	Cinchonine	IX
	Alkaloid	Cinchonidine	X
Rubia	Anthraquinone	Purpurin	XXI
	Anthraquinone	Alizarin	XIX

* shown in Figure 2.

Figure 2

Different classes of compounds isolated from Rubiaceae.

4. Chemotaxonomic Considerations

Chemotaxonomic studies use chemical characteristics, particularly secondary metabolites from a group of organisms to determine their taxonomic classification [36]. This correlation between phytochemical compounds and morphological data becomes an important tool to determine plant classification, phylogeny and evolution [37,38,39].

The plant evolution process, from a morphological point of view, occured by the successive appearance of small weeds, larger herbs, shrubs and, finally, trees achieving the climax with primitive angiosperms. Then, the evolutionary polarity became inverted, woody plant being gradually replaced by herbaceous plants [40,41]. As explained by Gottlieb: “The most conspicuous evolutionary trend in the gross morphology of land plants concerns the successive appearance of small weeds, larger herbs, shrubs and, finally, trees. This trend had attained or even had passed its climax with the primitive angiosperms and within this division the evolutionary polarity became inverted, woody plants being gradually replaced by herbaceous plants.

These successional phenomena are paralleled by micromolecular compositions. The ubiquitous flavonoids excepted, polyketides and terpenoids dominate the chemical compositions of bryophytes and pteridophytes. Shikimate-derived aromatics became numerically significant only in gymnosperms and attain predominance over other biosynthetic classes in primitive angiosperms. Concomitantly, here secondary metabolism reflects the trend from woody to herbaceous forms by inactivation of cinnamoyl/cinnamyl-derivatives through two phenomena: (i) extension of the shikimate pathway by reduction of cinnamyl alcohols to allylphenols and propenylphenols and (ii) gradual curtailment of the final steps of the shikimate pathway. The former alternative is most frequent in the primitive magnolialean block, where oxidative oligomerization of the precursors leads to neolignans. The first consequence of the latter alternative, the accumulation of phenylalanine and tyrosine, again very frequent in the magnolialean block, occurs also in the rosiflorean block. Oxidative elaboration of these amino acids leads to benzylisoquinolines. Further shortening of the shikimate pathway is restricted to the rosiflorean block. It leads to the accumulation of chorismic acid, the precursor of anthranilate- and of tryptophane-derived alkaloids, and of shikimic acid, the precursor of gallic acid- and ellagic acid-derived tannins. With gallic acid, the possibilities of diversifying the production of micromolecules through gradual curtailment of the shikimate pathway seem to be exhausted. In the most highly advanced, mostly sympetalous, angiosperms, shikimate-derived secondary metabolites play a relatively minor role. In these lineages, the full potential of acetate utilization leads to polyacetylenes, while mevalonate utilization leads to steroidal alkaloids, iridoids, alkaloids, sesquiterpene lactones, etc. In comparison with the polyketides and terpenoids of less advanced plant groups mentioned above, these compounds all show a high state of oxidation.” [40].

Regarding the distribution of the major secondary metabolites in Rubiaceae, indole alkaloids are indicated as the main chemical markers of this family [42,43,44,45,46]. Iridoids, anthraquinones, triterpene glycosides, flavonoids, lignoids, terpenes and phenols derivatives, were also reported [47]. Indole alkaloids occur just in families belonging to the Gentianales order (Loganiaceae, Rubiaceae, Apocynaceae and Naucleaceae), where one observes monoterpene indole alkaloids mainly [48]. The occurrence of indole alkaloids out of Gentianales order is quite rare and when found they are usually simple indole alkaloids.

A good correlation between the biosynthetic pathways and morphological aspects of the Ixoroideae, Cinchonoideae and Rubioideae subfamilies is obtained by evaluating chemical data, combined with the parameters cited by Robbrecht [8]. Each one of these subfamilies presents a different and typical profile of indole alkaloids, iridoids and anthraquinones which are considered as Rubiaceae chemotaxonomic markers [49]. Other studies based on chemotaxonomic data obtained by gas chromatography coupled to mass spectrometry show that the iridoid glycosides are present in several different species belonging to the Rubiaceae subfamilies [50,51,52]. Monoterpene indole alkaloids, especially which are derivatives of tryptamine and monoterpene (iridoid) secologanin are another predominant class in Rubiaceae. Quinoline alkaloids, which are products from the monoterpene indole and isoquinoline alkaloids rearrangement, yielding emetine-type alkaloids, are also characteristic of Rubiaceae, however, strychnine class alkaloids are not present in this family. Other alkaloid types are quite heterogeneous leading to a hard chemotaxonomic correlation [53].

Several studies have reported the use of chemical data to assist plant taxonomy [53]. Interest in this area increased due to the appearance of fast and accurate analytical techniques. However, there are still limitations on the application of chemical data in systematics. Even with a growing number of phytochemical studies, there are still many plants that remain without any chemical study.

5. Data Obtained Through the Bibliographic Survey

The present study sought to survey phytochemical studies of all species of Rubiaceae published in ScienceDirect and CAS SciFinder websites between 1990 and 2014. The data compiled in this review show the distribution of the studied species classified by their respective tribes and subfamilies as well as the isolated compounds and their chemical classes (Table 2).

Table 2

Compounds isolated from Rubiaceae species, organized by subfamily and tribe.

Subfamily	Tribe	Species	Compound (s)	References
Cinchonoideae	CHI	Chiococca alba	Triterpene glycosides: chiococcasaponins I–V	[65]
			Cetoalcohols: 4-hydroxy-heptadecan-7-one; 5-hydroxy-octadecan-11-onePhenylcoumarines: 5,7,4′-trimethoxy-4-phenylcoumarineLignans: exostemin; matairesinol; d-mannitol	[66]
			Seco-iridoids: albosides I–III	[67]
			Nor-seco-pimarane: merilactone	[68]
			Triterpene: 3-β-hydroxyolean-12,15-dien-28-oic acid	[69]
			Triterpene glycosides: O-α-d-apiofuranosyl (1→3)-[α-d-apiofuranosyl (1→4)]-α-l-rhamnopyranosyl (1→2)-α-l-arabinopyranosyl 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12,15-dien-28-oate; 28-O-α-d-apiofuranosyl (1→3)-α-l-rhamnopyranosyl (1→2)-α-l-arabinopyranosyl 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12,15-dien-28-oate	[70]
			Ent-kaurane diterpenes: 1-hydroxy-18-nor-kaur-4,16-dien-3-one; 15-hydroxy-kaur-16-en-3-one; kaur-16-en-19-ol; kaurenoic acid; merilactone; ribenone	[71]
			Ent-kaurane: ent-17-hydroxy-16α-kauran-3-one	[72]
		Chiococca braquiata	Flavonoids: 4′-methoxykaempferol-7-(acetyloxy)-3,5-O-α-l-rhamnoside; apigenin; 7-O-methoxyquercetrin; quercetrinTriterpenes: α-amirin; β-amirin; ursolic acid; oleanolic acid	[73]
		Coutarea hexandra	Coumarins: 5-O-β-d-glucopyranosyl-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one; 5-O-β-d-galactopyranosyl-4-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-oneCucurbitacins: 23,24-dihydrocucurbitacin F; 23,24-dihydro-25-acetylcucurbitacin F; 2-O-β-d-glucopyranosyl-23,24-dihydrocucurbitacin F	[74]
		Exostema acuminatum	Nor-diterpenes: ent-16,17-diidroxicauran-19-nor-4-en-3-one;ent-16,17-dihydroxy-kauran-19-nor-4-en-3-onePhenylcoumarins: 5,7,4′-trimethoxy-4-phenylcoumarin;7,4′-dimethoxy-5-hydroxy-4-phenylcoumarin;5,7,4′-trimethoxy-3′-hydroxy-4- phenylcoumarin;5,7,4′-trimethoxy-8-hydroxy-4-phenylcoumarin (exostemin I);5,7,4′-trimethoxy-8,3′-dihydroxy-4′-phenylcoumarin;	[75]
			7,4′-dimethoxy-5,3′-hydroxy-4′-phenylcoumarin	[75]
		Exostema caribaeum	Phenylcoumarin: 5-O-β-d-galactopyranosyl-7-methoxy-3′, 4′-dihydroxy-4-phenylcoumarin	[76]
		Hintonia latiflora	Phenylcoumarin: 5-O-(6′′acetyl-β-d-glucopyranosyl)-7,3′,4′-trihydroxy-4-phenylcoumarinPhenylstyrene: 6-O-β-d-glucopyranosyl-2,3′,4β-trihydroxy-4-methoxy-β-phenylstyrene	[77]
		Hintonia standleyana	Phenylcoumarin: 3-O-β-d-glucopyranosyl-23,24-dihydrocucurbitacin F; 5-O-[β-d-apiofuranosyl-(1→6)-β-d-glucopyranosyl]-7-methoxy-3′,4′-dihydroxy-4-phenyl-coumarin; desoxycordifolinic acid	[78]
	CIN	Cinchona ledgeriana	Quinolinic alkaloids: quinine; quinidine; cinchonidine and cinchonine	[79,80]
		Cinchona robusta	Anthraquinones: robustaquinones A–H; 1,3,8-trihydroxy-2-methoxyanthraquinone; copareolatin 6-methyl ether	[81]
		Ladenbergia oblongifolia	Alkaloids: epicinchonicinol; cinchonidicinol; mixture of dihydrocinchonicinol and dihydrocinchonidicinol	[82]
		Remijia peruviana	Quinolinic alkaloids: quinine; cuprein; cinchonine; acetylcupreine; N-ethylquinine	[83]
			Alkaloids: remijinine; epiremijinine; 5-acetylapocinchonamine; N-acetyldeoxy-cinchonicinol; N-acetylcinchonicinol	[84]
		Sickingia tinctoria	Indole alkaloids: sickingin; 5-carboxystrictosidine; ophiorines A–B; lyalosidic acid	[85]
		Sickingia williamsii	Indole alkaloids: sickingin; 5α-carboxystrictosidine; ophiorines A–B; lyalosidic acid	[85]
	GUE	Antirhea acutata	Triterpene-methyl ester: nor-seco-cycloartane	[86]
		Antirhea lucida	Indole alkaloids: N,N-methyl-3′-indolylmethyl-5-methoxytryptamine; N,N-dimethyltryptamine; 6-methoxy-2-methyl-1,2,3,4-tetrahydro-13-carboline	[87]
		Antirhea portoricensis	Indole alkaloids: 20-epiantirhine; isoantirhine; antirhine; yohimbol; epi-yohimbol; 19(S)-hydroxydihydrocorinanteol	[88]
		Chomelia obtusa	Triterpenes: 3-O-β-d-quinovopyranosyl-28-O-β-d-glycopyranosyl quinovic acid; 3-O-β-d-quinovopyranosyl-28-O-β-d-glycopyranosyl cincholic acid; ursolic acid; oleanolic acidFlavonoids: (3-O-β-d-glycopyranosyl quercetin; 3-O-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] quercetin;3,5-O-dicaffeoyl quinic acid; 4,5-O-dicaffeoyl quinic acid	[89]
		Guettarda grazielae	Triterpenes: α-amyrin acetate; cycloartenone; 3β,19α,23-trihydroxyurs-12-ene; 3-β-O-β-d-glucopyranosylquinovic acid; 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic; acid ursolic acid	[90]
			Iridoid: guettardodiolSeco-iridoid: sarracenin; 7α-morroniside; 7β-morroniside	[91]
		Guettarda noumeana	Quinolinic alkaloids: cupreine; dihydrocupreine;N-methyldihydroquinicinol; N-methylquinicinol	[92]
		Guettarda pohliana	Triterpenes: ursolic acid; oleanolic acid; pomolic acid; rotundic acid; 3β,6β,19α,23-tetra-hydroxyurs-12-en-28-oic acid; clethric acidMonoterpene: 5-O-caffeoylquinic acid; loliolideSeco-iridoid: secoxiloganin	[93]
			Triterpenes glycosides: 28-O-β-d-glycopyranosyl-3-O-β-d-quinovopyranosyl quinovic acid; 28-O-β-d-glycopyranosyl-3-O-β-d-glycopyranosyl quinovic acid; 3-O-β-d-glycopyranosyl quinovic acid; 28-O-β-d-glycopyranosyl-3-O-β-d-glycopyranosyl cincholic acid; quinovic acid; daucosterolPhenolic compound: 4,5-O-dicaffeoylquinic acid	[94]
		Guettarda speciosa	Phenolic compounds: 1-O-α-d-glucuronide 3-O-benzoyl ester; guettardionosideIndole alkaloid: cadambineIridoid glycoside: sweroside; morronisideSteroids: ecdysone; icariside D1Triterpene: quinovic glycoside C	[95]
		Machaonia brasiliensis	Steroids: 3β-O-β-glucopyranosyl stigmasterol; 3β-O-β-glucopyranosyl sitosterolSeco-iridoid: secologanosideFlavonoid: 7-O-β-glucopyranosyl quercetagetinClorogenic acids: 4,5-O-dicaffeoylquinic acid; 5-O-caffeoylquinic acid.	[96]
		Neolamarckia cadamba	Indole alkaloids: neolamarckines A–B	[97]
		Neolaugeria resinosa	Oxindole alkaloids: neolaugerine; isoneolaugerine; 15-hydroxyneolaugerine	[98]
		Timonius timon	Triterpenes: 3β,6β,23-trihydroxy-olean-12-en-28-oic acid; 3β,6β,19α,23-tetrahydroxy-olean-12-en-28α-oic acid	[99]
	HAM/HIL	Chione venosa var. venosa	Acetophenone derivatives: ortho-hydroxy-acetophenone-azine; acetophenone-2-O-β-d-glucopyranoside; acetophenone-2-O-[β-d-apiofuranosyl-(1→6′)-O-β-d-glucopyranosyl]Iridoid glycosides: 4α-morroniside; sweroside; diderrosideTriterpene: daucosterol	[100]
	HAM	Deppea blumenaviensis	β-carboline alkaloids: deppeaninol	[101]
		Hamelia magniflora	Indole alkaloids: magniflorine; ajmalicine	[102]
		Hamelia patens	Indole alkaloids: (−)-hamelin; tetrahydroalstonin; aricine; pteropodine; isopteropodine; uncarine F; speciophylline; palmirine; mitraphylline; rumberine	[103]
	HYM	Hymenodictyon excelsum	Triterpenes: 3β-hydroxy-11-oxours-12-en-28-oic acid; 3β-hydroxy-27-p-(Z)-coumaroyloxyolean-12-en-28-oic acid; 3-oxo-11α,12α-epoxyurs-13β,28-olide; 3β-hydroxy-11α,12α-epoxyurs-13β,28-olide; 3β-hydroxyurs-11-en-13(28)-lactone; oleanolic acid; uncarinic acid E (3β-hydroxy-27-(E)-p-coumaroyloxyolean-12-en-28-oic acid; ursolic acid; ursonic acid; 3β-(formyloxy)-urs-12-en-28-oic acid	[104]
		Hymenodictyon floribundum	Glycosides: scopolin; himexelsin or xeroboside; scopoletin	[105]
			Iridoids: floribundane A–B	[106]
	ISE	Isertia haenkeana	Indole alkaloids: dihydroquinamine; epidihydroquinamine; apodihydrocinchonamine; 3-carbomethoxy-5-(l′-hydroxyethyl) pyridine	[107]
		Isertia pittieri	Triterpene glycosides: pyrocincholic acid 3β-O-α-d-quinovopyranosyl-28-[β-d-glucopyranosyl(1→6)-β-d-glucopyranosyl] ester; pyrocincholic acid 3β-O-β-d-quinovopyranosyl(1→6)-α-d-glucopyranosyl-28-[-β-d-glucopyranosyl(1→2)-β-d-glucopyranosyl] ester; quinovic acid 3α-O-R-l-rhamnopyranosyl(28→1)-β-d-glucopyranosyl ester; quinovic acid 3β-O-β-d-glucopyranosyl(1→4)-R-l-rhamnopyranosyl-(28→1)-β-d-glucopyranosyl ester	[108]
	NAU	Adina cordifolia	Coumarins: umbelliferone; skimmin; 7-methoxycoumarin and 7-hydroxy-8-acetyl coumarin	[109]
		Adina racemosa	Flavonoid glycosides: quercetin3-O-R-l-rhamnopyranosyl(16)-(3-O-trans-p-coumaroyl)-α-d-galactopyranoside; quercetin 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-p-coumaroyl)-R-l-rhamnopyranosyl(1→2)]-(4-O-trans-p-coumaroyl)-α-d-galactopyranoside; kaempferol 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-p-coumaroyl)-R-l-rhamno-pyranosyl(1→2)]-(4-O-trans-p-coumaroyl)-β-d-galactopyranoside; quercetin 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-p-coumaroyl)-R-l-rhamnopyranosyl(1→2)]-(3-O-trans-p-coumaroyl)-β-d-galactopyranoside; quercetin 3-O-R-l-rhamnopyranosyl(1→6)-[(4-O-trans-caffeoyl)-R-l-hamnopyranosyl-(1→2)]-(3-O-trans-p-coumaroyl)-β-d-galactopyranoside	[110]
			Secoiridoid glucosides: adinosides A–E; grandifloroside 11-methyl ester	[111]
		Adina rubella	Triterpenes glycosides: quinovic acid 3-O-β-d-glucopyranosyl (l→4)-β-d-fucopyranoside; quinovic acid 3-O-β-d-glucopyranosyl (1→4)-β-d-fucopyranoside (28→1)-β-d-glucopyranosyl ester; quinovic acid 3-O-β-d-glucopyranosyl (1→4)-α-l-rhamnopyranosyl-(28→1)-β-d-glucopyranosyl ester; quinovic acid 3-O-β-d-glucopyranosyl (1→2)-β-d-glucopyranosyl-(28→1)-β-d-glucopyranosyl ester	[112]
			27-Nor-triterpene glycosides: rubellosides C–D	[113]
		Adina polycephala	Iridoids: genipin-1-O-α-l-rhamnopyranosyl (1→6)-α-d-glucopyranoside	[114]
		Cephalanthus glabratus	Oxindole alkaloids: tetrahydroalstonine; mitraphylline; uncarine E	[115]
		Cephalanthus occidentalis	Triterpenes glycosides: 3-O-α-glucopyranosylcincholic acid; cincholic acid 28-O-α-glucopyranosyl ester; 3-O-β-glucopyranosyl-(1→4)-β-fucopyranosylcincholic acid; 3-O-β-glucopyranosyl-(1→4)-β-fucopyranosylcincholic acid 28-O-β-glucopyranosyl ester; 3-O-β-glucopyranosylcincholic acid 28-O-α-arabinopyranosyl-(1→2)-β-glucopyranosyl ester; 3-O-β-glucopyranosylquinovic acid 28-O-α-arabinopyranosyl-(1→2)-β-glucopyranosyl ester	[116]
		Corynanthe pachyceras	Indole alkaloids: corynanthine; α-yohimbine; dihydrocorynanthine; corynantheine; corynantheidine	[117]
		Mitragyna diversifolia	Monoterpe indole alkaloids: mitradiversifoline; specionoxeine-N(4)-oxide; 7-hydroxyisopaynantheine; 3-dehydropaynantheine; 3-isopaynantheine-N(4)-oxide	[118]
		Mitragyna inermis	27-Nor-glycosides triterpene: inermisides I–IITriterpenes: quinovic acid; 3-O-[β-d-glucopyranosyl-(1→4)-α-l-rhamnopyranosyl]; β-d-glucopyranosyl-[3-O-(β-d-glucopyranosyl)]-quinovic acid; 3-O-(β-d-6-deoxy-glucopyranosyl) quinovic acid	[119]
			Indole alkaloids: naucleactonin D; nauclefilline; angustoline; angustine; naucleficine; nauclefidineTriterpenes: barbinervic acid; quinovic acid; 3-O-α-l-rhamnopyranoside acid; betulinic acid; oleanolic acid; ursolic acid; strictosamide	[120]
			Oxindole alkaloids: mitraphylline; isomitraphylline; speciophylline; pteropodine	[121]
		Mitragyna parvifolia	Oxindole alkaloids: 16,17-dihydro-17β-hydroxyisomitraphylline; 16,17-dihydro-17β-hydroxymitraphylline; 2-isomitraphylline; mitraphylline	[122]
		Mitragyna rotundifolia	Triterpene glycosides: quinovic acid 3-O-β-d-6-deoxy-glucopyranoside 28-O-β-d-glucopyranosyl ester; quinovic acid 27-O-α-l-rhamnopyranosyl ester; 3-O-α-l-rhamnopyranoside; quinovic acid 27-O-β-d-glucopyranosyl ester; quinovic acid 3-O-6-deoxy- glucopyranoside; quinovic acid 27-O-β-d-glucopyranosyl ester; cincholic acid 3-O-β-d-6-deoxy-glucopyranoside; cincholic acid 28-O-β-d-glucopyranosyl ester	[123]
		Mitragyna speciosa	Indole alkaloids: mitragynine; speciogynine; speciociliatine; 7-hydroxy-mitragynine; paynantheine	[124]
		Nauclea cadamba	Gluco-indole alkaloids: 3β-dihydroisocadambine; cadambine; 3α-dihydrocadambine; 16-carbomethoxynaufoline; nauclechine; 5,11,12,5α-tetrahydroindolo[3,2-g]-pyridino-[4,3-b]indolizine	[125]
		Nauclea diderrichii	Triterpene glycosides: quinovic acid 3-O-α-l-rhamnopyranosyl (28→1)-β-d-gluco-pyranosyl ester; quinovic acid 3-O-β-d-glucopyranosyl (1→2)-d-glucopyranoside; quinovic acid 3-O-β-l-fucopyranosyl (28→1)-β-d-glucopyranosyl ester	[126]
			Indole alkaloids: 3α-5α-tetrahydrodeoxycordifoline; cadambine acid	[127]
Nauclea latifolia		Indole alkaloids: latifoliamides A–E; angustoline	[128]
Nauclea officinalis		Indole alkaloids: naucleficines A–E; naucleidinal; angustoline	[129]
		Indole alkaloids: naucline; angustine; angustidine; nauclefine; naucletine	[130]
		Triterpenes: 3β,19α,23,24-tetrahydroxyurs-12-en-28-oic acid; 2β,3β,19α,24-tetrahydroxyurs-12-en-28-oic acid; 3-oxo-urs-12-ene-27; 28-dioic acid; quinovic acid 3-β-rhamnopyranoside	[131]
Nauclea orientalis		Tetrahydro-β-carboline monoterpene alkaloid glucosides: naucleaorine; epimethoxynaucleaorine; strictosidine lactamTriterpenes: oleanolic acid; 3,4,5-trimethoxyphenol; 3-hydroxyurs-12-en-28-oic acid methyl ester; 3α,23-dihydroxyurs-12-en-28-oic acid; 3α,19α,23-trihydroxyurs-12-en-28-oic acid methyl ester	[132]
		Indole alkaloids: nauclealines A–B; naucleosides A–B; strictosamide; vincosamide; pumiloside	[133]
		Indole alkaloids: naucleaorals A–B	[134]
Nauclea pobeguinii		Indole alkaloids: naucleidinal; magniflorine; naucleofficine D; diastereoisomers of 3,14-dihydroangustoline; strictosidine; desoxycordifoline; 3α,5α-tetrahydrodeoxycordifoline lactamPhenolic compound: kelampayoside A	[135]
		Indole alkaloid: nauclequinine; nauclefoline; nauclefidine	[136]
Neonauclea purpurea		Quinolinic alkaloid: 2,6-dimethoxy-1,4-benzoquinone	[137]
		Indole alkaloids: cadambine; α-dihydrocadambine
Neonauclea sessilifolia		Triterpene glycosides: 3-O-β-d-glucopyranosyl quinovic acid; 3-O-β-d-glucopyranosyl-(1→2)-β-d-quinovopyranosyl quinovic acid; 3-O-β-d-quinovopyranosyl pyrocincholic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester; 3-O-α-l-rhamnopyranosyl-(1→4)-β-d quinovopyranosyl pyrocincholic acid 28-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranosyl ester	[138]
		Triterpene: ursolic acid	[139]
		Chromone-secoiridoid glycosides: sessilifoside; 7′′-O-β-d glucopyranosylsessilifosideIndole alkaloid glycosides: neonaucleosides A–CGlycosides: 5-hydroxy-2-methylchromone-7-O-β-d-apiofuranosyl-(1→6)-β-d-glucopyranoside; sweroside; loganin; grandifloroside; quinovic acid 3β-O-β-d-quinovopyranoside-28-O-β-d-glucopyranoside	[140]
Ochreinauclea maingayii		Indole alkaloids: neonaucline; cadamine; naucledine	[141]
Pausinystalia johimbe		Monoterpene indole alkaloid: yohimbine	[142]
Uncaria attenuata		Oxindole alkaloids: corynoxine; corynoxine B; isocorynoxeine; epi-allo-corynantheine; dihydrocorynantheine pseudoindoxylIndole alkaloids: 19-epi-3-iso-ajmalicineTriterpene: ursolic acid	[19]
Uncaria borneensis		Alkaloids: isorhynchophylline; rhynchophylline; isocorynoxeine; corynoxeine;Indole alkaloids: allo-yohimbine; pseudo-yohimbine; 3-epi-β-yohimbine	[143]
Uncaria callophylla		Indole alkaloids: dihydro-corynantheine; gambirine; isogambirine; gambireine; rotundifoline; callophylline; callophyllines A–B; yohimbine; pseudoyohimbine; β-yohimbine; α-yohimbine	[144]
		Indole alkaloids: callophyllines A–B; 3-epi-β-yohimbine; gambirine	[144]
Uncaria cordata var. cordata and Uncaria cordata var. ferruginea		Indole alkaloids: dihydrocorynantheine	[143]
Uncaria elliptica		Pentacyclic oxindole alkaloids: formosanine; isomitraphylline; mitraphyllineIndole alkaloids: ajmalicine	[145]
		Triterpenes: 3β,6β,19α-trihydroxy-23-oxo-urs-12-en-28-oic acid; 3β,6β,19α,23-trihydroxy-23-oxo-urs-en-28-oic acid; 3,6-dioxo-19α-hydroxy-urs-12-ene-28-oic acid; 3β,6β-diacetoxi-19-hydroxy-urs-12-ene-28-oic acid; quinovic acid 3β-O-β-d-quinopyranosyl-(28→1)-β-d-glucopyranosyl ester	[145]
Uncaria gambir		Proanthocyanidins: gambiriins A1–A2 ; gambiriins B1–B2; (+)-catechin; (+)-epicatechin; procyanidin B1; procyanidin B3; gambiriin	[146]
Uncaria glabrata		Monoterpene indole alkaloids: 14α-hydroxyrauniticine; rauniticine; uncarine C–E; glabratine; deoxycordifoline	[147]
Uncaria guianensis		Indole alkaloid: 3-isoajmalicineOxindole alkaloids: isomitraphylline; mitraphylline; isomitraphylinic acid	[38]
		Indole alkaloid: ajmalicineOxindole alkaloids: formosanine or uncarine B; isomitraphylline; mitraphylline	[148]
		Triterpenes: quinovic acid 3β-O-β-d-quinovopyranoside; quinovic acid 3β-O-β-d-fucopyranosyl-(27→1)-β-d-quinovopyranosyl ester; quinovic acid 3β-O-[β-d-glucopyranosyl-(1→3)-β-d-fucopyranosyl]-(27→1)-β-d-glucopyranosyl ester; quinovic acid 38-O-β-d-fucopyranoside	[149]
Uncaria hirsuta		Bis(monoterpenoid) indole alkaloid glucosides: hirsutaside D; bahienoside A–B; neonaucleoside B	[150]
		Phenolic compound: chlorogenic acidAlkaloid: uncarine BFlavonoids: quercitrin; rutin; hiperin; neohesperidin	[151]
Uncaria lanosa var. glabrata and Uncaria lanosa var. ferrea		Pentacyclic oxindole alkaloids: isopteropodine; pteropodine	[143]
Uncaria longiflora var. longiflora		Alkaloids: isorhynchophylline; rhynchophylline; iso-corynoxeine; corynoxeine	[143]
Uncaria longiflora var. pteropoda		Pentacyclic oxindole alkaloids: pteropodine; isopteropodine	[143]
		Pentacyclic oxindole alkaloids: pteropodine; isopteropodine	[152]
Uncaria macrophylla		Oxindole alkaloids: rhynchophylline; isorhynchophylline; corynoxine; corynoxine B	[153]
Uncaria rhynchophylla		Indole alkaloids: tetrahydroalstonine; tetrahydroalstonine-N-oxide; akuamigine; (4R)-akuamigina-N-oxide; (4S)-akuamigine-N-oxide; corynantheine; dihydrocorynantheine; dihydrocorynantheine-N-oxide; hirsuteine; geissoschizine methyl ether; hirsutine N-oxide; akuamigine pseudoindoxyl; rauniticine pseudoindoxyl; 3-isorauninticine pseudoindoxyl; dihydrocorynantheine pseudoindoxyl; vallesiachotamine; vincoside lactam; strictosamide; rhynchophyne; 2′-O-β-d-glucopyranosyl-11-hydroxyvincoside lactam; angustine; angustoline; angustidine	[154]
		Sesquiterpene indole alkaloids: (5S)-5-carboxystrictosidine; 3,4-dehydro-(5S)-5-carboxystrictosidineIndole alkaloids: cadambine; 3α-dihydrocadambine; 3β-isodihydrocadambinePentacyclic oxindole alkaloids: isorhynchophylline; rhynchophylline; corynoxeine; isocorynoxeine; corynoxeine; rhynchophylline N-oxide; isorhynchophylline N-oxide; macrophylline A; 18-19-dehydrocorynoxinic acid; 22-O-demethyl-22-O-β-d-glucopyranosyl isocorynoxeine	[154]
		Oxindole alkaloids: rhynchophylline; corynoxeine; corynanteine; hirsutine	[155]
		Oxindole alkaloids: isocorynoxeine; isorhynchophylline; orynoxeine; rhynchophyllineIndole alkaloids: corynanteine; dihydrocorynanteine	[156]
		Pentacyclic oxindole alkaloids: 22-O-demethyl-22-O-β-glucopyranosyl isorhynchophylline; 22-O-demethyl-22-O-β-glucopyranosyl rhynchophylline; 22-O-demethyl-22-O-β-glucopyranosyl isocorynoxeine; isorhynchophylline acid; 9-hydroxy isocorynoxeine; 18,19-dehydrocorynoxinic acid; 18,19 dehydrocorynoxinic acid B; rhynchophyllic acid; 9-hydroxycorynoxeine; isocorynoxeine N-oxide; rhynchophylline acid N-oxide; corynoxeine N-oxide; isocorynoxeine; rhynchophylline; isorhynchophylline N-oxide; isorhynchophylline; corynoxeineIndole alkaloid: vincoside lactamPhenolic compounds: chlorogenic acid; neochlorogenic; cryptochlorogenic; quinic acid; cis-5-caffeoylquinic acid; procyanidin b1; procyanidin b2; catechin; epi-catechin; rutin	[157]
Uncaria salaccensis		Oxindole alkaloids: 3-oxo-7-hydroxy-3,7-secorhynchophylline	[158]
Uncaria sinensis		Alkaloids: isohynchophyllic acid; pteropodic acid; 3α-dihydrocadambine; 3β-isodihydrocadambine	[159]
		Proanthocyanidin: procyanidin B-1	[160]
Uncaria tomentosa		Pentacyclic alkaloids: isomitraphylline; mitraphylline; uncarine F; speciophylline; isopterophylline; pterophylline; isocorynoxeineTetratacyclic alkaloids: corynoxeine; isorincophylline; rincophylline	[161]
		Alkaloids: cinchonain Ia; cinchonain Ib	[162]
	Oxindole alkaloids: uncarines C–E; mitraphylline; isomitraphyllineIridoid glycosides: 7-deoxyloganic acid	[163]
	Triterpenes glycosides: 3-oxo-6β-19α-dihydroxyurs-12-en-28-oic acid; 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic acid;3β-methoxy-16α-hydroxyurs-12,19(29)-dien-27,28-dioic acid;3β-hydroxyurs-12-en-27,28-dioic acid	[164]
	Oxindole alkaloids: pteropodine; isopteropodine; speciophylline; uncarine F; mitraphylline; isomitraphylline; rincophylline; isorincophylline	[165]
	Oxindole alkaloids: mitraphylline	[166,167]
	Indole alkaloid: 3-isoajmalicine	[168]
	Alkaloids: cinchonain Ia; cinchonain Ib	[162]
	Iridoids: tomentosides A–BPhenolic compound: (−)-epi-cathequin	[169]
	Triterpenes: oleanolic acid; 3β,6β,19α-trihydroxyurs-12-en-28-oic acid	[170]
	Triterpenes: 3β,6β,19α-trihydroxyurs-12-en-23-al-28-oic acid; 3β,19α-dihydroxy-6-oxo-urs-12-en-23-al-28-oic acid; 3β,19α-dihydroxy-6-oxo-urs-12-en-23-ol-28-oic acid	[171]
	Triterpene: 23-nor-24-esomethylene-3β,6β-19α-trihydroxyurs-12-en-28 oic acid; 3β,6β,19α-trihydroxyurs-12-en-28-oic acid; 3-oxo-6β,19α-dihydroxyurs-12-en-28 oic acid; oleanic acid	[169]
Uncaria villosa	Indole alkaloids: villocarines A–D	[172]
Ixorideae	ALB	Alberta magna	Iridoids: (+)-5-acetaldehyde-l-formyl-2-methylcyclopentan; 5-acetaldehyde-1-formyl-2- methylcyclopent-1-ene; 1,4α,5,6,7α-hexahydro-1-hydroxy-7-methylcyclopenta-pyran-4-carboxaldeyde; 4,4α,5,7α-tetrahydro-1-hydroxy-4-(hydroxymethylene)-7-methylcyclopentane-pyran-3-(1H)-one; 5-deoxystansioside; 6,10-bisdeoxyaucubin; boschnaloside	[173]
	COF	Coffea sp	Alkaloid: caffeine	[174]
		Coffea bengalensis	Alkaloid: caffeineDiterpene: 16-epicafestol	[175]
		Nematostylis anthophylla	Triterpene glycosides: randianin; 2′′-O-acetylrandianin; 6′′-O-acetylrandianin	[176]
		Tricalysia dubia	Diterpenes: tricalysiol A–B; tricalysiolide B; tricalysioside G tricalysioside L	[177]
			Ent-kaurane glycosides: tricalysiosides A–G	[178]
		Tricalysia okelensis	Ent-kaurane glycosides: ent-kauran-3α,16α,17-triol-19-al 3-O-[5-O-vanilloyl-β-d-apiopyranosyl(1→6)]-β-d-glucopyranoside; ent-kauran-3α,16α,17-triol-19-al; 3-O-[5-O-E-sinapoyl-β-d-apiopyranosyl(1→6)]-β-d-glucopyranoside	[179]
	CON	Calycophyllum spruceanum	Seco-iridoids: 7-methoxydiderroside,6′-O-acetyldiderroside; 8-O-tigloyldiderroside; loganetin; loganin; secoxyloganin; kingiside; diderroside	[180]
		Chimarrhis turbinata	Indole monoterpene alkaloids: strictosidine; strictosidine acid; 5α-arboxystrictosidine; isovallesiachotamine; vallesiachotamine; turbinatine; 3,4-dehydro-strictosidine; turbinatineβ-Carboline alkaloids: cordifoline; deoxycordifoline; harman-3-carboxylic acid	[181]
		Crossopteryx febrifuga	Triterpene glycosides: 3β-(α-l-rhamnopyranosyloxi)-28-O-(β-d-glucopyranosyl)urs-12,20(30)-diene-27,28-dioic acid	[182]
		Emmenopterys henryi	Triterpenes: 3β,19α,23-trihydroxyurs-12-en-24-al-28-oic acid; 3β,19α,24-trihydroxy-23-norurs-12-en-28-oic acid; 3β,12β-dihydroxy-5α-pregnane-14,16-dien-20-one; and 12β-hydroxy-5α-pregnane-14,16-dien-3,20-dione; 3β,19α,23,24-tetrahydroxyurs-12-en-28-oic acid; pomolic acid; 3β,6β,19α,23-tetrahydroxyurs-12-en-28-oic acid; 3β,6β,23-trihydroxyolean-12-en-28-oic acid; 3β,6β,19α,23-tetrahydroxyolean-12-en-28-oic acid; 3β,23,24-trihydroxyolean-12-en-28-oic acid; 3β,12β-dihydroxy-5α-pregnane-16-en-20-one; 12β-dihydroxy-5α-pregnane-16-en-3,20-dione	[183]
		Pogonopus speciosus	Alkaloids: 1′,2′,3′,4′-tetradehydrotubulosine; tubulosine; psychotrine	[184]
		Pogonopus tubulosus	Alkaloid: tubulosine	[185]
			Alkaloids: tubulosine; psychotrine; cephaeline	[186]
		Simira glaziovii	Alkaloids: aribin; ophiorine B; lyalosideMonoterpenes: methyl 3,4-dimethoxycinamate	[187]
		Simira eliezeriana	Diterpenes: simirane A [(5R,6R,8R,9R,10S,11S,13S)-6 β,11β -dihydroxy-2,4(18),15-erythroxylatrien-1-one]; simirane B [(5S,8R,9R,10S,11S,13S)-11-hydroxy-2,4(18),15-erythroxylatrien-1-one]	[188]
	GAR	Alibertia edulis	Iridoids: 6β-hydroxy-7-epigardoside methyl ester	[189]
		Alibertia macrophylla	Diterpene: ent-kaurane-2β,3α,16α-triolTriterpenes: lupenone; germanicone; α-amirenone; β-amirenone; lupeol; oleanolic acid; ursolic acidGlucosidic iridoids: 6α-hydroxygeniposide; 6β-hydroxygeniposide; gardenoside; shanziside methylesterPhenolic acids: protocatechuic; vanilic; caffeic	[190]
		Alibertia myrciifolia	Coumarin: scopoletin	[64]
			Flavonoid: corymbosin	[191]
			Iridoid: 10-O-vanilloylgeniposidic acid	[192]
			Triterpenes: pomolic acid methyl ester; ursolic acid methyl ester; oleanolic acid methyl ester	[193]
		Alibertia sessilis	Phenolic compounds: 3,4,5-trimethoxyphenyl-1-O-β-d-(5-O-syringoyl)-apiofuranosyl-(1→6)-β-d-glucopyranosideIridoids: geniposidic acid; geniposide; 6α-hydroxygeniposide; 6β-hydroxygeniposideLignans glycosides: (+)-lyoniresinol-3α-O-β-d-glucopyranoside; (−)-lyoniresinol-3α-O-β-d-glucopyranoside	[64]
			Flavonoids: quercetin-3-O-β-d-(2′′-O-trans-p-coumaroyl)-rutinoside; kaempherol-3-O-β-d-(2′′-O-trans-p-coumaroyl)-rutinosideTriterpenes: oleanolic acid; ursolic acid; epi-betulinic acidIridoids: gardenoside; deacetylasperuloside; 10-dehydrogardenoside; β-gardiol; α-gardiol	[46]
		Burchellia bubalina	Iridoids: β-gardiol; α-gardiol; garjasmine	[60]
		Canthium gilfillanii	Iridoid: geniposidic acid	[61]
		Catunaregam nilotica	Triterpene glycosides: 28-O-β-d-glucopyranosyl-3-O(O-α-l-rhamnopyranosyl-(1→3)-O-β-d-glucopyranosyl]-(1→3)]-β-d-glucopyranosyl) oleanolate; 3-O-[2′,3′-di-O-(β-d-glucopyranosyl)-β-d-glucopyranosyl] oleanolic acid; 3-O-(O-α-l-rhamnopyranosyl-(1→3)-O-[O-β-d-glucopyranosyl-(1→3)]-β-d-glucopyranosyl) oleanolic acid; 3-O-[O-β-d-glucopyranosyl-(1→3)-β-d-glucopyranosyl] oleanolic acid	[194]
		Catunaregam spinosa	Triterpene glycosides: catunarosides A–D; swartziatrioside; aralia-saponin V–IV	[195]
		Coptosapelta flavescens	Anthraquinones: 1,4-dimethoxy-2-methylanthraquinone; 2-amino-3-methoxycarbonyl-1,4-naphtoquinone	[196]
		Duroia hirsuta	Iridoid: plumericin	[197]
			Iridoid lactone: duroinFlavonol: ether flavonol-3-O-methyl	[198]
		Duroia macrophylla	Triterpenes: oleanolic acid; ursolic acid	[199]
		Gardenia collinsae	Triterpenes: 20R,24R-epoxy-3-oxodammarane-25ξ, 26-diol; C-24-epimer; 20R,24R-ocotilone	[200]
		Gardenia gummifera	Cycloartane triterpenes: dikamaliartanes A–FFlavonoid: 3′,5,5′-trihydroxy-4′,6,7,8-tetramethoxyflavone	[201]
		Gardenia jasminoides	Coumarines: ferrulic acid; skimmin; uracil; 5,8-di-(3-methyl-2,3-dihydroxy-butyloxypsoralen); 3-O-α-d-glucopyranosyl-(1→4)-β-d-glucopyranosyloxypeucedanin	[202]
			Iridoids: genipin 1-O-β-d-d-isomaltoside; 1,10-di-O-β-d-glucopyranoside; genipin 1-O-β-d-gentiobioside; geniposide; scandoside methyl ester; deacetylasperulosidic acid methyl ester; 6-O-methyldeacetylasperulosidic acid methyl ester; gardenoside	[59]
			Iridoids: 8-epi-apodantheroside; 7β,8β-epoxy-8α-dihydrogeniposide	[203]
			Iridoids: 6′-O-[(E)-sinapoyl] gardoside; 4′′-O-[(E)-p-coumaroyl]-gentiobiosylgenipin; 6′-O-[(E)-caffeoyl]-deacetylasperulosidic acid methyl ester	[204]
			Iridoid: 6-O-sinapoylgeniposide	[205]
			Monoterpenes: gardenone; gardendiol	[206]
			Carotenoids: crocetin; crocetin mono (β-d-glucosyl) ester; crocetin di-(β-d-glucosyl) ester; crocetin mono-(β-gentiobiosyl) ester; crocetin (β-d-glucosyl)-(β-gentiobiosyl) ester; crocin [crocetin-di-(β-gentiobiosyl)ester]; crocetin (β-gentiobiosyl)-(β-neapolitanosyl) ester; crocetin-di-(β-neapolitanosyl) ester	[207]
			Monoterpenes: jasminosides J–K; 6′-O-trans-sinapoyljasminoside B; 6′-O-trans-sinapoyljasminoside L; jasminosides M–P; jasminoside C; jasminol E; sacranoside B	[208]
			Flavonoid: luteolin-7-O-β-d-glucopyranosideTriterpenes: ursolic acid; oleanolic acid; methyl 3,4-di-O-caffeoylquinate; methyl 5-O-caffeoyl-3-O-sinapoylquinate; methyl 3,5-di-O-caffeoyl-4-O-(3-hydroxy-3-methyl)glutaroylquinate; methyl 5-O-caffeoyl-4-O-sinapoylquinateGlycosides: 2-methyl-l-erythritol-4-O-(6-O-trans-sinapoyl)-β-d-glucopyranoside; 2-methyl-l-erythritol-1-O-(6-O-trans-sinapoyl)-β-d-glucopyranoside	[209]
			Iridoids: 6′-O-trans-p-coumaroyl geniposidic acid; 11-(6-O-trans-sinapoyl glucopyranosyl)-gardendiol; 10-(6-O-trans-sinapoyl glucopyranosyl)gardendiol; 6′′-O-trans-sinapoylgenipin gentiobioside; 6′′-O-trans-cinnamoylgenipin gentiobioside; 10-O-succinoylgeniposide; 6′-O-acetylgeniposide; 6′′-O-trans-p-coumaroylgenipin gentiobioside	[210]
			Iridoids: gardaloside	[211]
			Iridoids: garjasmine; dunnisin; α-gardiol; β-gardiol; diffusoside A diffusoside B; genameside C; deacetylasperulosidic acid	[212]
		Gardenia jasminoides var. radicans	Iridoid glycoside: 6′′-O-trans-feruloylgenipin gentiobioside; 2′-O-trans-p-coumaroylgardoside; 2′-O-trans-feruloylgardoside	[213]
		Gardenia lucida	Cycloartane triterpenes: dikamaliartanes A–FFlavonoid: 3′,5,5′-trihydroxy-4′,6,7,8-tetramethoxyflavone	[201]
		Gardenia saxatilis	Triterpenes: lupenone; lupeol; betulinic acid; messagenic acid A; messagenic acid B; oleanolic acid; ursolic acid; acid (27-O-feruloyloxybetulinic acid; 27-O-p-(Z)- and 27-O-p-(E)-coumarate esters of betulinic acid and a mixture of uncarinic acid E (27-O-p-(E)-coumaroyloxyoleanolic acid) and 27-O-p-(E)-coumaroyloxyursolic acid	[214]
		Gardenia sootepensis	Sesquiterpene: sootepdienone	[215]
		Gardenia thailandica	Flavonoids: 5,7-dihydroxy-7,2′,3′,4′,5′,6′-hexamethoxyflavone; 5,7-dihydroxy-2′,3′,4′,5′,6′-pentamethoxyflavone; 5-hydroxy-7,2′,3′,4′,5′-pentamethoxyflavone; 5,7-dihydroxy-2′,3′,4′,5′-tetramethoxyflavoneTriterpenes: thailandiol; gardenolic acid; quadrangularic E acid; 3β-hydroxy-5α-cycloart-24(31)-en-28-oic acid	[216]
		Gardenia fructus	Iridoids: genipin 1-O-β-gentiobioside; 10-O-acetylgeniposide; 6α-hydroxygeniposide; 6β-hydroxygeniposide; gardenoside; picrocrocinic acid; 6′-O-sinapoyljasminoside; 10-O-(4′′-O-methylsuccinoyl) geniposide; jasminosides Q–R; 6-O-p-coumaroylgeniposide; 6′-O-acetylgeniposide; 6′-O-sinapoylgeniposide	[217]
			Iridoids: geniposidic acid; genipin 1-β-gentiobioside; geniposide; genipinFlavonoids: rutin; crocin-1; crocin-2Phenolic compound: chlorogenic acid	[218]
			Iridoid glycosides: gardenoside; genipin 1-O-β-d-isomaltoside; genipin 1,10-di-O-β-d-glucopyranoside; genipin 1-O-β-d-gentiobioside; geniposide; scandoside methyl ester; deacetylasperulosidic acid methyl ester	[59]
		Genipa americana	Iridoids: genipaol; genipin; tarenoside; geniposidic acid; geniposide; genamesides A–D; genipin-gentiobioside; gardenoside; gardendiol; shanzhiside	[219]
			Monoterpenes: genipacetal; genipic acid; genipinic acid
		Genipa spruceana	Cycloartane triterpene: genipatriol	[220]
		Lamprothamnus zanguebaricus	Phenolic acids: 1-(3-hydroxy-4-methoxy-5-methylphenyl)-ethanone; 1-(3-hydroxy-4-methoxyphenyl)-ethanone	[221]
		Oxyanthus pallidus	Cycloartane glycosides: pallidiosides A–CTriterpenes: oleanolic acid; 3-O-β-d-glucopyranosyl-β-sitosterol	[222]
		Oxyanthus pyriformis	Cyanogenic glycosides: prunasin; amygdalin	[223]
		Oxyanthus speciosus	Phenolic compounds: 2-(2-hydroxy)-ethanol-β-d-glucopyranoside	[61]
			Cyanogenic glycosides: holocalin	[223]
		Pavetta owariensis	Proanthocyanidins: pavetannin A1; pavetannin A2; cinnamtannin B1; pavetanninB1; pavetannin B3; pavetannin B5; pavetannin B6	[224]
		Psydrax livida	Phenolic compounds: psydrosideMonoterpene: psydrin	[61]
Randia dumetorum		Iridoid: 11-methylixoside	[225]
		Triterpenes: α-l-arabinosyl(1→3)-β-galactopyranosyl(1→3)-3-β-hydroxyolean-12-en-28-methyloate	[226]
Randia Formosa		Triterpenes glycosides: randiasaponins I–VII; ilexoside XXVII; ilexoside XXXVII	[227]
Randia siamensis		Triterpenes: ursolic acid; pseudoginsenoside-RP 1; pseudoginsenoside-RT 1	[228]
Randia spinosa		Iridoid glycosides: randinoside; galioside; deacetylasperulosidic acid methyl ester; scandoside methyl ester; geniposide; gardenoside	[229]
Rothmannia macrophylla		Iridoids: macrophylloside	[230]
Rothmannia urcelliformis		Iridoid: genipinIridoid alcaloidal: gardenamide A; 4-oxonicotinamide-1-(1′-β-d-ribofuranoside)	[231]
Schumanniophyton problematicum		Alkaloids: rohitukine; rohitukine N-oxide; flavopiridol	[232]
Scyphiphora hydrophyllacea		Iridoid: scyphiphorin A1–A2; scyphiphorin B1–B2	[233,234]
Tocoyena brasiliensis		Triterpene glycosides: 3-O-β-d-quinovopyranosyl quinovic acid; 3-O-β-d-glucopyranosyl quinovic acid; 28-O-β-glucopyranosyl ester derivative of quinovic acidFlavonoid: ramnazin-3-O-rutinoside	[235]
Tocoyena bullata		Iridoid glycoside: gardenoside	[236]
Tocoyena formosa		Iridoids: α-gardiol; β-gardiol; gardenoside	[237]
IXO	Enterospermum madagascariensis	Sesquiterpenes: 2-hydroxy-10-epi-zonarene; 2,15-dihydroxycalamenene; guaia-4,6-dien-3-one	[238]
	Enterospermum pruinosum	Triterpenes glycosides: longispinogenin; 3,16-di-O-β-d-glucopyranoside; triacetyllongispinogenin; diglucoside	[239]
	Ixora coccinea	Triterpene: ursolic acid	[240]
		Proanthocyanidins: ixoratannin A-2; epicatechin; procyanidin A2; cinnamtannin B-1Flavonoids: kaempferol-7-O-α-l-rhamnoside; kaempferol-3-O-α-l-rhamnoside; quercetin-3-O-α-l-rhamnopyranoside; kaempferol-3,7-O-α-l-dirhamnnoside	[241]
		Triterpenes: lupeol; ixorene; 17β-dammara-12,20-diene-3β-ol	[242,243]
		Fenolic compounds: 3-O-caffeoylquinic acid; 5-O-caffeoylquinic acid; catechin; epicatechin; rutin; quercetin; kaempferol; quercetin 3-O-glucoside; quercetin 3-O-galactoside; kaempferol 7-O-glucoside	[244]
MUS	Heinsia crinata	Triterpene glycosides: heinsiagenin A-3β-O-(β-glucopyranosyl-(1→2)-β-d-glucopyranosyl-(1→6)-[α-l-rhamnpyranosyl-(1→2)]-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside); heinsiagenin A-3β-O-(α-l-rhamnopynosyl-(1→2)-β-d-glucopyranosyl-(1→2)-β-d-glucopyranoside)	[245]
	Mussaenda dona aurora	Iridoid glycoside: shanshiside D	[246]
	Mussaenda erythrophylla	Flavonoid: 5-hydroxy-7,4′-dimethoxyflavones;Phenolic compounds: 3-iso-cumaryloxycyclopropane-1-oic acid; 4-hydroxy-3-methoxy cinnamic acid	[247]
	Mussaenda incana	Iridolactona: shanzhilactoneIridoid glycosides: barlerin; mussaenosideTriterpene: lupeol	[248]
	Mussaenda macrophylla	Iridoid: 6-epi-barlerin	[249]
	Mussaenda roxburghii	Iridoid: shanzhiol	[250]
	Mussaenda pubescens	Monoterpenes: mussaenins A–C	[251]
		Triterpene glycosides: mussaendosides R-S; 6 α-hydroxygeniposide; 3β-O-β-d-glucopyranosyl quinovic acid 28-O-β-d-glucopyranosyl ester	[252]
OCT	Villaria odorata	Alkenoyloxy alkenol: villarinol	[253]
		Iridoids: morindolide; hydrophylin A; hydrophylin BSesquiterpene: vomifoliol	[254]
PAV	Pavetta owariensis	Proanthocyanidins: proanthocyanidin A-2; proanthocyanidin A-4; pavetannin AFlavonoids: (+)-catechin; (−)-epicatechin; (+)-epicatechin	[224]
	Tarenna attenuata	Iridoids: tarenninosides A–G	[255]
	Tarenna gracilipes	Cycloartane glycosides: tareciliosides H–M	[256]
		Cycloartane glycosides: tareciliosides A–G	[257]
	Tarenna madagascariensis	Iridoids: tarennin; gardenoside; geniposidic acidPhenolic compounds: p-cumaric acid; cafeic acid; chlorogenic acidFlavonoids: kaempferol 3-O-β-d-glucopyranoside-7-O-α-l-rhamnopyranoside; kaempferol 3-O-α-l-rhamnopyranoside-7-O-α-l-rhamnopyranoside; quercetin 3-O-α-l-rhamnopyranoside-7-O-α-l-rhamnopyranoside; kaempferol 3-O-α-l-(3′′-O-acetyl)-rhamnopyranoside-7-O-α-l-rhamnopyranoside; kaempferol 3-O-α-l-(4′′-O-acetyl) rhamnopyranoside-7-O-α-l-rhamnopyranoside	[258]
POS	Molopanthera paniculata	Iridoid glycosides: barlerin; shanzhiside methyl ester	[259]
SAB	Sabicea brasiliensis	Phenolic compounds: 5-O-caffeoylquinic acid; 3,5-O-dicaffeoylquinic acid; 4,5-O-dicaffeoylquinic acidCoumarine: scopoletinTriterpene: ursolic acid	[260]
	Sabicea grisea var. grisea	Steroid: octacosanol	[261]
		Coumarine: scopoletinPhenolic compounds: ethyl caffeate; salicylic acidSteroid: 3-O-β-d-glucopyranosylsitosterolTriterpene: vanillic acid	[262]
VAN	Canthium berberidifolium	Iridoid glycosides: 6-O-β-d-apiofuranosyl-mussaenosidic acidPhenolic diglycosides: canthosides A–D	[263]
	Canthium multiflorum	Iridoid: 6-oxo-genipin; macrophylloside; garjasmine; gardenine; gardenamide; deacetylasperulosidic acid; 6α-hydroxygeniposide; galioside; aitchisonide BTriterpenes: vanillic acid 4-O-β-d-(6-O-benzoylglucopyranoside); oleanolic acid; quinovic acid	[264]
	Canthium schimperianum	Cyanogenic glycoside esterified with an iridoid glycoside: 2R-[(2-methoxybenzoyl-genoposidyl)-5-O-β-d-apiofuranosyl-(1→6)-β-glucopyranosyl-oxy]-2-phenyl acetonitrile; oxyanthin	[265]
	Fadogia agrestis	Monoterpene glycosides: (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-β-d-glucopyranosyl-(12)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-(2-O-((2E,6Z)-8-hydroxy-2,6-dimethyloctadienoyl)-α-l-rhamnopyranosyl)-(1→3)-α-l-rhamnopyranosyl) oxy]-octadien-1-yl α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-(2-O-((2E,6Z)-8-hydroxy-2,6-dimethyloctadienoyl)-α-l-rhamnopyranosyl)-(1→3)-4-O-acetyl-α-l-rhamnopyranosyl) oxy]-octadien-1-yl α-l-rhamnopyranoside; (2E,6Z)-2,6-dimethyl-8-[(O-α-l-rhamnopyranosyl-(1→3)-(2-O-((2E,6Z)-8-hydroxy-2,6-dimethyloctadienoyl)-α-l-rhamnopyranosyl)-(1→3)-α-l-rhamnopyranosyl)-oxy]-octadien-1-yl-O-β-d-glucopyranosyl-(1→2)-α-l-rhamnopyranoside	[266]
	Fadogia ancylantha	Triterpene glycosides: 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-[R-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl] ester; 3-O-β-d-glucopyranosyl-3-β-hydroxyolean-12-en-28-oic acid 28-O-[-d-apiofuranosyl-(1→2)-β-d-glucopyranosyl] ester	[267]
	Fadogia homblei	Coumarine: scopoletinFlavones: luteolin; quercetin-3-O-β-d-galactosideTriterpenes: lupeol; betulinic acid; 3β-dodecanoyllup-20(29)-en-28-al; lup-20(29)-en-3β-ylhexadecanoate; oleanolic acid; ursolic acidLignan: 4,4′-dihydroxy-3,3′-dimethoxy-7,9′; 7′,9-diepoxylignan-((−)-pinoresinol)	[268]
	Vangueria spinosa	Proanthocyanidin: (−)-epicatechin-3-O-β-glucopyranoside	[269]
*	Augusta longifolia	Triterpenes: ursolic acid; acyl lupeolCoumarin: scopoletinFlavonoids: naringenin; kaempferol; quercetin; myricitrin; rutin	[270]
	Myrioneuron nutans	Alkaloid: myrobotinol	[271]
	Wendlandia formosana	Iridoid glycosides: 10-O-caffeoyl scandoside methyl ester; 6-methoxy scandoside methyl ester; scandoside methyl ester; methyl deacetyl asperulosidate; 10-O-caffeoyl daphyllosideTriterpene: ursolic acid	[272]
	Wendlandia tinctoria	Iridoid glycosides: 5-dehydro-8-epi-adoxosidic acid; 5-dehydro-8-epi-mussaenoside; 10-O-dihydroferuloyldeacetyldaphylloside; wendoside; 8-epi-mussaenoside	[273,274]
		Iridoids: 5-dehydro-8-epi-adoxosidic acid; wendoside	[273]
Rubioideae	ARG	Argostemma yappii	Pyrrolidinoindole alkaloid: (+)-isochimonanthine	[275]
	COU	Anthocephalus chinensis	Seco-iridoid glycoside: 3′-O-caffeoylsweroside; loganine; 8-epikingiside; loganic acid; swerosidePhenolic apiglycosides: kelampayosides A–BIndole alkaloids: cadambine; strictosidine lactam; 5α-carboxystrictosidine; desoxycordifoline	[276]
		Coussarea brevicaulis	Triterpenes: 3-epi-spathodic acid; coussaric acid; barbinervic acid; scutellaric acid	[277]
		Coussarea hydrangeifolia	Phenylpropanoid glycosides: 1′-O-benzyl-α-l-rhamnopyranosyl-(1′′→6′)-β-d-glucopyranoside; α-l-xylopyranosyl-(4′′→2′)-(3-O-β-d-glucopyranosyl)-10-O-(E)-caffeoyl-β-d-glucopyranoside; 1,6-di-O-caffeoyl-β-d-glucopyranoside; 1-O-(E)-caffeoyl-β-d-glucopyranoside 1-O-(E)-feruloyl-β-d-glucopyranoside	[278]
		Coussarea paniculata	Triterpenes: lupeol; lupeyl acetate; botulin; betulinic acid; 3-epi-betulinic acid; 3-epi-betulinaldehyde; oleanolic acid; ursolic acid; lup-20(29)-en-3β,25-diol; lup-20(29)-en-11R-ol-25,3β-lactone; 3-deoxybetulonic acid	[279]
		Coussarea platyphylla	Triterpenes: betulonic acid; betulinic acidIridoid: monotropeinDiterpene: trans-phytol	[280]
		Cruckshanksia pumila	Iridoids: asperuloside; 7-α-methoxysweroside; swertiamarine	[246,281]
		Heterophyllaea pustulata	Anthraquinones: soranjidiol; soranjidiol-1-methyl ether; rubiadin; rubiadin-1-methyl ether; damnacanthal; damnacanthol	[282]
			Anthraquinones: soranjidiol; rubiadin; rubiadin-1-methyl ether	[283]
	KNO	Knoxia corymbosa	Chromone glycosides: corymbosins K1–K4; noreugenin; undulatoside A	[284]
		Knoxia valerianoides	Anthraquinones: 2-hydroxymethylknoxiavaledin; 2-ethoxymethylknoxiavaledin; 2-formylknoxiavaledin	[285]
			Anthraquinones: lucidin; lucidin-ω-methyl ether; rubiadin; damnacanthol; 1,3,6-trihydroxy-2-methoxymethylanthraquinone; 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone; 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-β-primeveroside; vanillic acid	[286]
		Pentas bussei	Pentacyclic cyclol-type naphthohydroquinone: eriobrucinol; methyl 5,10-dihydroxy-7-methoxy-1,1,3α-trimethyl-1a,2,3,3a,10c,10d-hexahydro-1H-4-oxacyclobuta[cd]-indeno[5,6-a]naphthalene-9-carboxylate	[287]
			Benzochromene: methyl-5,10-dihydroxy-7-methoxy-3-methyl-3-[4-methyl-3-pentenyl]-3H-benzo[f]chromene-9-carboxylate	[288]
		Pentas lanceolata	Anthraquinones: 5,6-dihydroxydamnacanthol; nordamnacanthal ; lucidin-ω-methyl ether; damnacanthol	[289]
			Iridoid: tudoside; 13(R)-epi-gaertneroside; 13(R)-epi-epoxygaertneroside; (E)-uenfoside; (Z)-uenfoside	[290]
		Pentas longiflora	Quinones: pentalongin; mollugin	[291]
			Quinones: pentalongin; mollugin; trans-3,4-dihydroxy-3,4-dihydromollugin; methyl-2,3-epoxy-3-prenyl-1,4-naphthoquinone-2-carboxylate; tectoquinone; 3-hydroxymollugin	[289]
		Pentas micrantha	Anthraquinones: tectoquinone; lucidin-ω-methyl ether; damnacanthol; rubiadin-1-methyl ether; rubiadin; damnacanthal; 5,6-dihydroxydamnacanthol; munjistin methyl ester	[292]
		Pentas schimperi	Anthraquinones: schimperiquinones A–B; cleomiscosin A; 2-hydroxymethylanthraquinoneTriterpene: oleanolic acid	[293]
			Triterpenes: oleanolic acid; ursolic acid	[294]
	LAS	Lasianthus fordii	Iridoid glycosides: asperuloside; deacetylasperuloside; methyl deacetyl-asperuloside; megastigmane glucoside; lasianthionoside A–C	[295]
		Lasianthus gardneri	Triterpenes: lupenone; lupeol; ursolic acid; canaric acid; 3,4-seco-lupane	[296]
		Lasianthus wallichii	Iridoids: iridolactone; iridoid dimer of asperuloside; asperulosidic acid	[297]
		Ronabea emetic	Iridoid glycosides: asperuloside; 6-hydroxygeniposide; deacetylasperulosidic acid; asperulosidic acid	[298]
	MOR	Coelospermum billardieri	Iridoids: coelobillardin	[299]
		Morinda citrifolia	Anthraquinone glycosides: digiferruginol-1-methylether-11-O-β-gentiobioside; digiferruginol-11-O-β-primeveroside; damnacanthol-11-O-β-primeveroside; 1-methoxy-2-primeverosyloxymethyl-anthraquinone-3-olate; 1-hydroxy-2-primeverosyloxymethyl-anthraquinone-3-olate; 1-hydroxy-5,6-dimethoxy-2-methyl-7-primeverosyloxyanthraquinone	[300]
			Anthraquinones: alizarin or 1,2-dihydroxyanthraquinone	[301]
			Anthraquinones: 5,15-dimethylmorindol; alizarin 1-methyl ether; anthragallol 1,3-dimethyl ether; anthragallol 2-dimethyl ether; 6-hydroxy-anthragallol-1,3-dimethyl ether; demorindone-5-dimethyletherIridoids: morindacin; asuperlosidic acid; deacetylasperulosidic acid	[302]
			Fatty acid glucosides: 1,6-di-O-octanoyl-β-d-glicopiranose; 6-O-(-β-d-glucopyranosyl)-1-O-decanoyl-β-d-glicopyranose	[303]
			Iridoid glycosides: 6R-hydroxyadoxoside; 6β,7β-epoxy-8-epi-splendoside; americanin A; narcissoside; asperuloside; asperulosidic acid; borreriagenin; citrifolinin B epimer a; citrifolinin B epimer b; cytidine; deacetylasperuloside; dehydromethoxygaertneroside; epi-dihydrocornin; methylR-d-fructofuranoside; methyl-β-d-fructofuranoside; nicotiflorosideFatty acid glycoside : β-sitosterol 3-O-β-d-glucopyranoside	[304]
			Iridoid glycosides: 9-epi-6α-methoxy geniposidic acid	[305]
			Iridoids: morindacin	[302]
			Triterpenes: 1-O-(3′-methylbut-3′-enyl)-β-d-glucopyranose; 1-n-butyl-4-(5′-formyl-2′-furanyl)methylsuccinate; 4-epi-borreriageninIridoid glycosides: asperulosidic acid; deacetylasperulosidic acid; 1-n-butyl-4-methyl-2-hydroxysuccinate; 1-n-butyl-4-methyl-3-hydroxysuccinate	[306]
			Iridoid glycoside: citrifoside	[307]
		Morinda coreia	Iridoid glycosides: yopaaosides A–C; 10-O-acetylmonotropein; 6-O-acetylscandosidePhenolic glycosides: 3,4,5-trimethoxyphenyl 1-O-β-apiofuranosyl (1′→6′′)-β-glucopyranoside	[308]
		Morinda elliptica	Anthraquinones: 2-formyl-1-hydroxyanthraquinone; 1-hydroxy-2-methylanthraquinone; nordamnacanthal; damnacanthal; lucidin-ω-methyl ether; rubiadin; soranjidiol; morindone; rubiadin-l-methyl ether; alizarin-l-methyl ether; morindone-5-methyl ether	[309,310,311]
		Morinda longissima	Coumarine: scopoletin	[312]
		Morinda lucida	Anthraquinones: oruwal; oruwalol; damnacanthal; nor-damnacanthal; soranjidiol; alizarin-l-methyl ether; rubiadin; rubiadin-l-methyl ether; 2-methylanthraquinone; anthraquinone-2-aldehyde; l-hydroxy-2-methylanthraquinone; l-methoxy-2-methyl-anthraquinone; hexacosanoic acid	[313]
		Morinda morindoides	Flavonoids: quercetin; quercetin 7,4'-dimethylether; luteolin 7-glucoside; apigenin 7-glucoside; quercetin 3-rhamnoside; kaempferol 3-rhamnoside; quercetin 3-rutinoside; kaempferol 3-rutinoside; chrysoeriol 7-neohesperidoside	[314]
			Flavonoids: quercetin; quercetin-3-O-rutinoside; kaempferol-7-O-rhamnosylsophoroside; chrysoeriol-7-O-neohesperidoside; quercetin-7,4′-dimethylether; quercetin-3-O-rhamnoside; kaempferol-3-O-rhamnoside; kaempferol-3-O-rutinoside; apigenin-7-O-glucoside; luteolin-7-O-glucoside; kaempferol; apigenin; luteolinIridoids: epoxygaertneroside; methoxygaertneroside; gaertneroside; gaertneric acid	[315]
			Iridoid: 6′-O-acetyl-3′′-methoxygaertneroside	[316]
		Morinda officinalis	Monoterpene: monotropein	[317]
			Anthraquinones: 1,3,8-trihydroxy-2-methoxy anthraquinone; 2-hydroxy-1-methoxy-anthraquinone; rubiadin	[318]
		Morinda pandurifolia	Anthraquinones: soranjidiol; lucidin-ω-methyl ether; damnacanthal; 1-methoxy-2-methyl anthraquinone; 3-hydroxy-1-methoxy-2-methoxymethyl anthraquinone; anthragallol; nordamnacanthal; flavopurpurin; damnacanthal; lucidin; soranjidiolIridoid glycoside: asperulosidic acid	[319]
		Morinda royoc	Anthraquinones: nordamnacanthal; damnacanthal; lucidin; soranjidiol; rubiadin 1-methylether	[320]
		Morinda umbellata	nor-Iridoids: umbellatolides A–B	[321]
	OPH	Lerchea bracteata	Alkaloids: dihydrocorynantheol; dihydrositsirikine; β-hunterburnin methoclhoride; α-hunterburnine methoclhoride; dihydrocorynantheol; melinonine B; methobromide; yombine methobromide; 4-methylanthirine; diploceline; malindine; iso-malindine; dihydro-3-epi-corynantheol methoclhoride (lercheine)	[322]
		Myrioneuron faberi	Alkaloid: myriberine A	[323]
		Ophiorrhiza blumeana	Indole alkaloids: bracteatine; ophiorrhizine; ophiorrhizine-12-carboxylate; cinchonamine	[324]
		Ophiorrhiza bracteata	Indole alkaloids: bracteatine	[325]
		Ophiorrhiza communis	Indole alkaloids: harman; strictosidinic acid	[326]
		Ophiorrhiza hayatana	Anthraquinones: ophiohayatones A–C	[327]
		Ophiorrhiza kunstleri	Indole alkaloids: ophiorrhines A–B	[328]
		Ophiorrhiza liukiuensis	Monoterpene glycosides: demethylsecologanol; 3-O-glucosylsenburiside IIIndole alkaloids: camptothecin; 9-methoxycamptothecin; pumiloside; (3R)-deoxypumiloside; 10-methoxycamptothecin; estrictosamide; lyalosidic acid; ophiorrhines A–B; harmanIridoids: loganic acid; loganin; swertiaside ATriterpene: ursolic acid; epi-vogelosideMonoterpene: swerosideFlavonoid: hyperinCoumarin: scopoletin	[329]
			β-Carbolinic alkaloids: lyalosidic acid; lyaloside; 10-hydroxylyalosidic acid; ophiorrhines A–B; ophiorrhines methyl ester A–B	[330]
		Ophiorrhiza japonica	β-Carbolinic alkaloids: lyaloside; lyalosidic acid; 10-hydroxylyalosidic acid; ophiorrhines A–B; ophiorrhines methyl ester A–B
		Ophiorrhiza pumila	Pentacyclic alkaloid: camptothecin	[331]
			Anthraquinones:1-hydroxy-2-methylanthraquinone; 3-hydroxy-2-methylanthraquinone; 3-hydroxyanthraquinone-2-carbaldehyde; 1-hydroxy-2-hydroxymethylanthraquinone; 3-hydroxy-2-hydroxymethylanthraquinone; 1,3-dihydroxy-2-methylanthraquinone	[332]
			Alkaloids: camptothecin; 9-methoxycamptothecin; pumiloside; (3R)-deoxypumiloside	[329]
			Alkaloids: camptothecin; (3S)-pumiloside; (3S)-deoxypumiloside; (3R)-deoxy-pumiloside; strictosamide	[333]
			Alkaloids: camptothecin; pumiloside; (3S)-deoxypumiloside; (3R)-deoxypumiloside; strictosamide 9-methoxycamptothecin	[330]
		Ophiorrhiza rosacea	Indole alkaloids: ophiorrhines A and B	[328]
		Ophiorrhiza rugosa var decumbens	Anthraquinones: 1-hydroxy-2-hydroxymethyl-3-methoxyanthraquinone; 2-n-butoxy-methyl-1,3-dihydroxyanthraquinone	[334]
Ophiorrhiza trichocarpon		Indole alkaloids: ophiorrhisides A–F; 3,4,5,6-tetradehydrodolichantoside; lyaloside; dolichantoside; 5-oxostrictosidine	[335]
Ophiorrhiza tomentosa		Indole alkaloids: harman; strictosidinic acid	[326]
PAE	Paederia foetidae	Phenolic acid: ethyl p-methoxy-trans-cinnamate	[336]
	Paederia scandens	Iridoid glycosides: paederoside; paederoside B; asperuloside; paederosidic acid; methylpaederosidate; saprosmoside E	[337]
		Iridoid glycosides: paederoside; asperuloside; paederosidic acid; asperulosidic acid; paederosidic acid methyl ester; geniposide	[338]
		Iridoid glycosides: paederosidic acid; paederoside; asperulosidic acid; asperuloside; geniposidic acid; deacetylasperulosidic acid; decatilasperuloside methyl ester	[339]
		Iridoid: 6β-O-β-d glucosylparderosic acid	[340]
		Iridoid glycosides: asperuloside; paederoside; scanderoside	[341,342]
		Iridoid glycosides: 6′-O-E-feruloyl monotropein; 10-O-E-feruloyl monotropein	[343]
		Iridoid glycoside: paederoside B	[344]
PRI	Rennellia elliptica	Anthraquinone: 1,2-dimethoxy-6-methyl-9,10-anthraquinone; 1-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone; nordamnacanthal; 2-formyl-3-hydroxy-9,10-anthraquinone; damnacanthal; lucidin-ω-methyl ether; 3-hydroxy-2-methyl-9,10-anthraquinone; rubiadin; 3-hydroxy-2-methoxy-6-methyl-9,10-anthraquinone; rubiadin-1-methyl ether; 3-hydroxy-2-hydroxymethyl-9,10-anthraquinone	[345]
PSY	Camptotheca acuminata	Alkaloids: camptothecin; 10-hydroxycamptothecin	[346]
	Carapichea affinis	Alkaloids: cephaeline; emetine; ipecoside; 6-O-methylipecoside; 6-O-methyl-trans-cephaeloside; borucoside	[347]
	Cephaelis acuminata	Alkaloids: 2-O-β-d-glucopyranosyldemethylalangiside; demethylalangiside; 6′′-O-β-d-glucopyranosylipecoside; 6′′-O-α-d-glucopyranosylipecoside; ipecoside; (4R)-4-hydroxy-6,7-di-O-methyl ipecoside; (4S)-4-hydroxy-6,7-di-O-methylipecoside; 6,7-di-O-methylipecoside tetraacetate	[348]
		Alkaloids: emetine; cephaeline; neocephaeline 7-O-demethylcephaeline; 10-O-demethylcephaeline; 2′-n-(1′′-deoxy-1′′-β-d-buctopyranosyl) cephaeline; 2′′-n-(1′′-deoxy-1′′-β-d-fructopyranosyl) pyranosyl	[349]
	Cephaelis acuminata	Alkaloids: neocephaeline; 7′-O-demethylcephaeline; 10-O-demethylcephaeline; 2′-n-(10-deoxy-10-β-d-fructopyranosyl) cephaeline; 2′-n-(10-deoxy-10′′-β-d-fructopyranosyl) neocephaeline; emetine; cephaeline; psychotrine; protoemetine; 9-demethylprotoemetinol; isocephaeline	[349]
	Cephaelis dichroa	Indole alkaloids: vallesiachotamine lactone; vallesiachotamine; strictosamide; strictosidine; angustine	[350]
	Cephaelis ipecacuanha	Tetrahydroisoquinoline-monoterpene glucosides: 3-O-demethyl-2-O-methylalangiside; alangiside or ipecoside; 6-O-methylipecoside; 7-O-methylipecoside; 3-O-demethyl-2-O-methylalangiside; 2-O-methylalangiside	[351]
		Alkaloids: emetine; cephaeline; psychotrine; emetamine; O-methylpsycotrine	[352]
	Chassalia curviflora var. ophioxyloides	Indole alkaloids: alstrostine A; rudgeifoline	[353]
	Margaritopsis cymuligera	Pyrrolidinoindoline alkaloids: hodgkinsine; quadrigemine C	[354]
	Palicourea acuminata	Indole alkaloid: strictosidinic acid; methylester strictosidine; palicoside; bahienoside B; 5α-carboxystrictosidine; desoxycordifoline; lagamboside; vallesiachotamine	[355]
	Palicourea adusta	Monoterpenoid glucoindole alkaloids: lyaloside; tetra-(O-acetyl)-lyaloside; (E)-O-(6′)-cinnamoyl-4′′-hydroxy-3′′-methoxylyaloside; (E)-tetra-(O-acetyl)-O-(6′)-cinnamoyl-4′-hydroxy-3′-methoxylyaloside; (E)-tetra-(O-acetyl)-O-(6′)-cinnamoyl-4′′-hydroxy-3′′,5′′-dimethoxylyaloside	[356]
	Palicourea crocea	Monoterpenoid indole alkaloids: 3,4-dihydro-1-(1-β-d-glucopyranosyloxy-1,4α,5,7-tetrahydro-4-methoxycarbonylcyclopenta[c]pyran-7-yl)-β-carboline-N2-oxide; croceaine A; psychollatine	[357]
	Palicourea coriacea	Glucoindole alkaloids: 3-epi-strictosidinic acid; strictosidinic acid; strictosidinic ketoneAlkaloid: calycanthineTriterpene: ursolic acid	[358]
	Palicourea crocea	Monoterpene Indole Alkaloids: croceaines A–B	[359]
	Palicourea rigida	Indole alkaloid: vallesiachotamine	[360]
	Prismatomeris connata	Anthraquinone glycosides: 1-O-methylrubiadin 3-O-β-primeveroside; damnacanthol 3-O-β-primeveroside; rubiadin 3-O-β-primerveroside; lucidin 3-O-β-primeverosideo; 1,3-dihydroxy-2-(methoxymethyl) anthraquinone 3-O-β-primerveroside; digiferruginol ω-gentiobiose	[361]
		Phenolic compound glycoside: prismaconnatoside	[362]
	Prismatomeris malayana	Anthraquinone: 1,3-dihydroxy-5,6-dimethoxy-2-methoxymethyl-9,10-anthraquinone; 2-hydroxymethyl-1-methoxy-9,10-anthraquinone; tectoquinone; 1-hydroxy-2-methyl-9,10-anthraquinone; rubiadin; rubiadin-1-methyl ether; 1,3-dihydroxy-5,6-dimethoxy-2-methyl-9,10-anthraquinone; nordamnacanthal; damnacanthal	[363]
	Prismatomeris tetrandra	Iridoids: prismatomerin	[364,365]
	Psychotria bahiensis	Bis(monoterpenoid) indole alkaloid glucosides: bahienoside A; bahienoside B; 5R-carboxystrictosidine; angustine; strictosamide; (E)- and (Z)-vallesiachotamine	[366]
	Psychotria barbiflora	β-Carbolinic alkaloids: harman; strictosidinic acid	[367]
	Psychotria brachyceras	Monoterpene indole alkaloids: brachycerine	[368]
	Psychotria camponutans	Pyranonaphthoquinones: pentalongin; psychorubrin; 1-hydroxy-3,4-dihydro-1H-benz[g]isochromene-5,10-dione	[369]
	Psychotria colorata	Alkaloids: (−)-calycanthine; isocalycanthine; (+)-chimonanthine; hodgkinsine; quadrigemine C; (8-8a),(8′-8′a)-tetradehydroisocalycanthine 3a(R),3′a(R)	[370]
	Psychotria calocarpa	Alkaloids: psychotriasine	[371]
	Psychotria correae	Indole alkaloids: isodolichantoside; correantoside; 10-hydroxycorreantoside; correantines A–C e 20-epi-correantine BC13-Norisoprenoids: megastigm-5-ene-3,9-diol; S(+)-dehydrovomifoliolCarotenoids: lutein	[372]
	Psychotria glomerulata	Quinoline alkaloids: glomerulatines A−C; calycanthine; iso-calycanthine	[373]
	Psychotria ipecacuanha	Alkaloids: emetine; cephaeline	[374]
	Psychotria leiocarpa	Indole alkaloids: umbellatine; brachicerine; lyaloside; strictosamide; myrianthosines A–B; n,β-D-glucopyranosyl vincosamide quadrigemine AIridoid glucosides: asperuloside; deacetylasperuloside; loganin	[375]
	Psychotria myriantha	Indole alkaloids: strictosidinic acid	[376]
		Indole alkaloids: strictosidinic acid	[377]
	Psychotria nuda	Alkaloid: strictosamide	[378]
	Psychotria lyciiflora	Alkaloids: meso-chimonanthine; hodgkinsine; N-demethyl-meso- chimonanthine; quadrigemine C; isopsycotridine B; psychotridine; quadrigemine I; oleoidine; caledonine	[379]
	Psychotria oleoides
	Psychotria prunifolia	Alkaloids: strictosamide; 10-hydroxyiso-deppeaninol; N-oxide-10-hydroxy-antirhine	[380]
		Indole-β-carboline alkaloids: 10-hydroxyisodeppeaninol; N-oxide-10-hydroxy-antirhine; 14-oxoprunifoleine; strictosamide	[381]
		Indole-β-carboline alkaloids: 14-oxoprunifoleine; strictosamide; 10-hydroxyantirhine N-oxide; 10-hydroxyisodeppeaninol	[382]
	Psychotria suterella	Indole alkaloids: lyaloside; naucletine; strictosamide	[383]
	Psychotria umbellata	Indole alkaloids: psycollatine	[384]
	Psychotria vellosiana	Triterpenes: squalene; lupeolidsCoumarin: scopoletin	[385]
	Psychotria viridis	Alkaloid: dimethyltryptamine	[386]
	Rudgea jasminoides	Anthraquinone: 1,4-naphthohydroquinone	[387]
PUT	Plocama pendula	Naphthohydroquinones: mollugin 6-methyl ether; plocanaphthinLignans: syringaresinol; pinoresinol; lariciresinolCoumarin: scopoletin	[388]
		Anthraquinones: balonone; balonone; methyl ether; plocamanones A–C; knoxiadin; 5,6-dimethyl ether; plocamanone D; chionone; isozyganein dimethyl ether; lucidin 1,3-dimethyl ether; lucidin; 1-hydroxy-2-methyl-9,10-anthraquinone; tectoquinone; rubiadin 3-methyl ether; rubiadin 1-methyl ether; rubiadin dimethyl ether; rubiadin; lucidin 3-methyl ether; munjistin ethyl ester; ibericin; damnacanthol ω-ethyl ether; alizarin dimethyl ether; alizarin 1-methyl ether; anthragallol 1,2-dimethyl ether; 3-hydroxy-2-(hydroxymethyl)-9,10-anthraquinone	[389]
		Triterpenes: 3-epi-pomolic acid 3α-acetate; baloic acid; meth; 19α-hydroxyoleanonic acid; 3β-hydroxyolean-11,13(18)-dien-28-oic acid; 3α-acetoxy-19α-hydroxyursa-12-en-28-oic acid; baloic acid;19α-hydroxyoleanonic acid	[390]
	Putoria calabrica	Flavonoids: calabricosides A–BIridoid: asperuloside; paederosidic acid; paederosideLignan glycosides: liriodendrin; dihydrodehydrodiconiferyl alcohol-4-O-β-d-glucopyranoside; 7S,8R,8′R-(–)-lariciresinol-4,4′-bis-O-β-d-glucopyranoside.	[391]
SPE	Borreria verticillata	Indole alkaloids: spermacoceine; borrerine; borreverine; isoborreverine	[392]
		Indole alkaloids: verticillatines A–BIridoids: scandoside methyl ester; 6′-O-(2-glyceryl) scandoside methyl ester; asperuloside acid	[393]
	Dunnia sinensis	Iridoid: dunnisinineIridoid glycoside: dunnisinoside	[394]
	Galianthe brasiliensis	Iridoid glycosides: asperuloside; deacetylasperuloside; mixture of Z- and E-6-O-p-coumaroylscandoside methyl ester	[395]
	Galianthe ramosa	Phenolic compound: epicatechinTriterpene: ursolic acidβ-carboline indole alkaloid: 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl) cyclopentanol	[396]
		β-carboline alkaloid: 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl) cyclopentanol; 9-methoxyindole alkaloid	[396]
	Galianthe thalictroides	β-carboline indole alkaloid: 1-methyl-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanol; 1-(hydroxymethyl)-3-(2-hydroxypropan-2-yl)-2-(5-methoxy-9H-β-carbolin-1-yl)-cyclopentanolAnthraquinones: 1-methylalizarin; morindaparvin-ACoumarin: scopoletin	[397]
	Hedyotis auricularia	β-Carboline alkaloid: auricularine	[398]
	Hedyotis capitellata	β-Carboline alkaloids: capitelline; cyclocapitelline; isocyclocapitelline; hedyocapitelline; hedyocapitine
	Hedyotis chrysotricha	β-Carboline alkaloid: chrysotricine
	Hedyotis capitellata	Anthraquinones: capitellataquinone A–D; rubiadin; anthragallol; 2-methyl ether; alizarin-1-methyl eter; digiferruginol; lucidin-3-O-β-glucoside	[399]
		β-Carboline alkaloids: capitelline; (−)-isocyclocapitelline; (+)-cyclocapitelline; isochrysotricine; chrysotricine	[400]
		β -Carboline alkaloids: capitelline; (+)-isocyclocapitelline; (+)-cyclocapitelline; isochrysotricine; chrysotricine	[401]
	Hedyotis chrysotricha	β-Carboline alkaloid: chrysotricine	[402]
	Hedyotis corymbosa	Iridoid glucosides: asperuloside; scandoside methyl ester	[403]
		Iridoids: hedycoryside A–C	[404]
	Hedyotis crassifolia	Triterpenes: ursolic acid; 3β-hydroxyurs-11-ene-23(13)-lactone; 3α,13β-dihydroxyurs-11-ene-28-oic acid; oleanolic acid; 3-β-d-glucopyranosyl-β-sitosterol and 3β,6β-dihydroxyolean-12-ene-28-oic acid	[405]
	Hedyotis diffusa	Iridoid glycosides: dunnisinoside; E-6-O-p-methoxycinnamoyl scandoside methyl ester; Z-6-O-p-methoxycinnamoyl scandoside methyl ester; E-6-O-p-feruloyl scandoside methyl ester; E-6-O-p-coumaroyl scandoside methyl ester; Z-6-O-p-coumaroyl scandoside methyl ester	[406]
		Iridoid glucosides: diffusosides A–B	[407]
		Anthraquinones: 2-methyl-3-methoxyanthraquinone; 2-methyl-3-hydroxyanthraquinone; 2-methyl-3-hydroxy-4-methoxyanthraquinone; 2,3-dimethoxy-6-methylanthraquinone	[398]
		Flavonoids: quercetin; quercetin 3-O-glucopyranoside; quercetin 3-O-sambubioside; quercetin 3-O-sophoroside; quercetin 3-O-rutinoside
	Hedyotis dichotoma	Anthraquinones:1,4-dihydroxy-2,3-dimethoxyanthraquinone; 1,4-dihydroxy-2-hydroxy-methylanthraquinone; 2,3-dimethoxy-9-hydroxy-1,4-anthraquinone; 2-hydroxymethyl-10-hydroxy-1,4-anthraquinoneFlavonoids: isovitexin	[398]
	Hedyotis intricata	Triterpene: lupeol; oleanolic acidIridoid: asperuloside	[408]
	Hedyotis hedyotidea	Iridoids: deacetylasperulosidic acid ethyl ester; hedyotoside; asperulosidic acid; asperuloside; deacetylasperuloside	[409]
	Hedyotis herbacea	Flavonoids: kaempferol 3-O-rutinoside; rutin; kaempferol 3-O-glucoside; kaempferol 3-O-arabinopyranoside; kaempferol-3-O-arabino pyranoside; quercetin 3-O-galactoside	[398,410] [410]
	Hedyotis nudicaulis	Triterpene glycosides: nudicaucins A–C; guaiacin D	[411]
	Hedyotis pinifolia	Anthraquinones:1,6-dihydroxy-7-methoxy-2-methylanthraquinone; 1,6-dihydroxy-2-methylanthraquinone; 3,6-dihydroxy-2-methylanthraquinon; 1,3,6-trihydroxy-2-methylanthraquinone	[412]
	Hedyotis tenelliflora	Iridoids: teneoside B	[413]
	Hedyotis verticillata	Flavonoids: kaempferitrin	[398]
	Hedyotis vestita	Stereoid: phytolFlavonoids: rutine; isohrametin 3-O-rutinoside; vomifoliol 9-O-β-d-glucopyranoside; auricularinIridoid: 6α-methoxygenyposide;Phenolic compound: sodium (1S,4aR,5R,7aR)-7-hydroxymethyl-5-methoxy-1-β-d-glucopyranosyloxy-1,4α,5,7α-tetrahydrocyclopenta[c]pyran-4-carboxylate	[414]
	Mitracarpus frigidus	Pyranonaphthoquinone: psychorubrin	[415]
	Mitracarpus scaber	Pentalongin hydroquinone diglycoside: harounoside	[416]
		Phenolic compounds: pentadecanoic; (Z)-octadec-9-enoic; tetradecanoic; (Z,Z)-octadeca-9,12-dienoic; (Z)-hexadec-9-enoic; octadecanoic; dodecanoic acid	[417]
	Mitracarpus villosus	Triterpenes: methyl ursalate; ursolic acid	[418]
	Oldenlandia corymbosa	Iridoid glycosides: geniposidic acid; scandoside; feretoside; 10-O-benzoylscandoside methyl ester; odenlandoside III; asperulosidic acid; deacetylasperulosidic acid	[419]
	Oldenlandia difusa	Triterpenes: ursolic acid	[420]
		Triterpenes: 2,6-dihydroxy-1-methoxy-3-methylanthraquinone; 2-hydroxy-1-methoxy-3-methylanthraquinone; 2-hydroxy-3-methylanthraquinone; quercetin-3-O-[2-O-(6-O-E-sinapoyl)-β-d-glucopyranosyl]-β-glucopyranoside; quercetina-3-O-[2-O-(6-O-E-feruloyl)-β-d-glucopyranosyl]-β-glucopyranoside; kaempferol-3-O-[2-O-(6-O-E-feruloyl)-β-d-glucopyranosyl]-β-galactopyranoside; quercetin-3-O-(2-O-β-d-glucopyranosyl)-β-d-glucopyranoside; rutin; quercertin	[421]
	Oldenlandia umbellata	Anthraquinones: 1,2,3-trimethoxyanthraquinone; 1,3-dimethoxy-2-hydroxy-anthraquinone; 1,2-dimethoxyanthraquinone; 1-methoxy-2-hydroxyanthraquinone; 1,2-dihydroxyanthraquinone	[422]
	Richardia grandiflora	Phenolic compounds: o-hydroxybenzoic acid; m-methoxy-p-hydroxybenzoic acid	[423]
	Saprosma fragrans	Anthraquinones: 4-dihydroxy-1-methoxyanthraquinone-2-corboxaldehyde; damnacanthal	[424]
	Saprosma hainanense	Alkaloids: saprosmine A; saprosmine B; marcanine A; quinolone; cleistopholine; 4-methoxycarbonyl-5; 10-benzogquinolinequinone; liriodenine	[425]
	Saprosma scortechinii	Iridoid: 6-O-epi-acetylscandoside	[426]
		Iridoids: 10-O-benzoyl deacetylasperulosidic acid; 3,4-dihydro-3α-methoxy-paederoside; saprosmosides A–H	[426]
		Bis-iridoid glucosides: saprosmosides A–FIridoid glucosides: 3,4-dihydro-3-methoxypaederoside; 10-O-benzoyldeacetylasperulosidic acid; deacetylasperuloside; asperuloside; paederoside; deacetylasperulosidic acid; scandoside; asperulosidic acid; 10-acetylscandoside; paederosidic acid; 6-epi-paederosidic acid; methylpaederosidate; monotropein	[427]
	Saprosma ternatum	Alkaloid: vittadinosideCoumarins: scopoletinIridoid glycosides: epiasperuloside; epipaederosidic acid; epipaederosiTriterpenes: betulinic acid; betulinaldehyde	[428]
	Spermacoce verticillata	Triterpenes: morolic acid; oleanolic acid; ursolic acid; 3,5-dioxofriedelaneFlavonoids: 3-O-α-l-rhamnopyranosyl quercetin; quercetinAnthraquinones: 2-hydroxy-3-methylanthraquinone	[429]
RUB	Asperula maximowiczii	Iridoids: asperuloides A–C	[430]
	Crucianella graeca	Coumarins: daphnin; daphnetin; daphnetin glucosideIridoids: deacetylasperulosidic acid; scandoside; asperuloside; asperulosidic acid; methyl ester of deacetylasperulosidic acid; dafiloside; geniposidic acid; 10-hydroxyloganin; deacetylasperuloside	[431]
	Crucianella maritima	Iridoid: deacetylasperulosidic acid 6'-glucoside sodium salt;Anthraquinones: 1-hydroxy-2-carbomethoxyanthraquinone; 6-methylanthragallol-2-methyl ether; 6-methylanthragallol-2,3-dimethyl ether; 6-methoxy-2-methylquinizarin; 1-hydroxy-2-methyl-6-methoxyanthraquinone	[432]
		Iridoids: asperuloside; asperulosidic acid; deacetylasperulosidic acid	[433]
	Cruciata glabra	Coumarins: daphnin; daphnetin; daphnetin glucosideIridoids: scandoside	[431]
	Cruciata laevipes	Coumarins: daphnin; daphnetin glucosideIridoids: scandoside; asperuloside; asperulosidic acid; methyl ester of deacetylasperulosidic acid; daphylloside
	Cruciata pedemontana	Coumarins: daphnin; daphnetin glucosideIridoids: scandoside; asperuloside; asperulosidic acid; methyl ester of deacetylasperulosidic acid; daphylloside
	Cruciata taurica	Monoterpenoid glycosides: cruciaside A (2,5-O-β-d-diglucopyranosyl-3-hydroxy-p-cymene); cruciaside B (5-O-β-d-glucopyranosyl-2,3-dihydroxy-p-cymene)	[434]
		Coumarin glucosides: daphnin; daphnetin glucoside; 7-O-(6′-acetoxy-β-d-glucopyranosyl)-8-hydroxycoumarin; 7-O-[6′-O-(3′′,4′′-dihydroxycinnamoyl)-β-d-glucopyranosyl]-8-hydroxycoumarin	[435]
	Crucianella graeca	Iridoids: deacetylasperulosidic acid; scandoside; asperuloside; asperulosidic acid; geniposidic acid; 10-hydroxyloganin; deacetylasperuloside; iridoid V3	[431]
	Galium album	Iridoid glycosides: secogalioside; asperuloside; deacetyl asperulosidic acid; scandoside; monotropein; asperulosidic acid; geniposidic acid; 10-hydroxyloganin; 10-hydroxymorroniside (isomers 7α e7β); daphylloside	[436]
	Galium aparine	Anthraquinone aldehyde: nordamnacanthal	[437]
	Galium lovcense	Iridoid glycosides: secogalioside; asperuloside; deacetyl asperulosidic acid; scandoside; monotropein; asperulosidic acid; geniposidic acid; 10-hydroxyloganin; 10-hydroxymorroniside (isomers 7α e7β); daphylloside; 7-β-hydroxy-11-methyl forsythide; 7-O-acetyl-10-acetoxyloganin	[436]
	Galium rivale	Iridoid glycosides: monotropein; scandoside; eacetylasperulosidic acid; geniposidic acid; asperulosidic acidTriterpene glycosides: rivalosides A–E e momordin II	[438]
	Galium macedonicum	Iridoid: macedonine	[439]
	Galium sinaicum	Anthraquinones: 6,7-dimethoxyxanthopurpurin; 6-hydroxy-7-methoxyrubiadin; 5-hydroxy-6-hydroxymethyl anthragallol 1,3-dimethyl ether; 7-carboxyanthragallol 1,3-dimethyl ether; anthragalloll-methyl ether 3-O-β-d-glucopyranoside; anthragallol l-methyl ether 3-O-rutinoside; anthragallol 3-O-rutinoside; alizarin 1-methyl ether 2-O-primeveroside	[440]
	Galium spurium	Flavonoids: asperulosidic acid ester ; asperuloside; caffeic acid; kaempferol-3-O-l-rhamnopyranoside; quercetin-3-O-[α-l-rhamnopyranosyl(1→6)-β-d-glucopyranoside]; isorhamnetin-3-O-glucopyranoside; quercetin-3-O-α-l-rhamnopyranoside; kaempferol-3-O-[α-l-rhamnopyranosyl(1→6)-β-d-glucopyranoside]; quercetin	[441]
	Galium verum	Anthraquinones: 1,3-dihydroxy-2 methoxy methyl; 1,3-dimethoxy-2-hydroxy; 1,3-dihydroxy-2-acetoxy; 1-hydroxy-2-hydroxy-methyl; 1,3-dihydroxy-2-methyl; 1-methoxy-2-hydroxy; 1,3-dihydroxy-2-hydroxy-methyl-6-methoxy; 1,6-dihydroxy-2-methyl anthraquinones	[442]
	Galium verum var. asiaticum	Iridoid glycoside: 10-p-dihydrocoumaroyl-6-α-hydroxygeniposide; 10-p-dihydrocoumaroyl deacetylasperuloside; asperulosidic acid methyl ester; asperuloside; asperulosidic acid; deacetylasperuloside; scandoside	[443]
	Rubia akane	Anthraquinones: 1,3-dihydroxyanthraquinone-2-al; lucidin-3-O-primeveroside	[437]
	Rubia cordifolia	Naphtoquinones: dihydromollugin; 2-carbomethoxy-3-(3'-hydroxy)-isopentyl-1,4-naphthohydroquinone 1,4-O-di-β-glucoside; 2-carbomethoxy-3-(3'-hydroxy) isopentyl-1,4-naphthohydroquinona 4-O-β-glucosideAnthraquinones: xanthopurpurin; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-β-glucoside; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone; 2-methyl-1-hydroxy-9,10-anthraquinone; 3-O-α-rhamnosyl(1→2)-β-glucoside; 3-O-(6'-O-acetyl)-α-rhamnosyl (1→2)-β-glucoside; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-(4′,6′-O-diacetyl)-α-rhamnosyl (1→2)-β-glucoside; 2-methyl-1,3,6-trihydroxy-9,10-anthraquinone 3-O-(3′,6′-O-diacetyl)-α-rhamnosyl (1→2)-β-glucoside	[444]
		Iridoids glycoside: 6-methoxygeniposidic acid; 6-methoxygeniposidic acid methyl esterTriterpene: oleanolic aldehyde acetateFenolic compound: furomollugin	[445]
	Rubia peregrina	Anthocyanins: cyanidin 3-O-glucoside; delphinidin 3-O-glucoside; cyanidin 3-O-arabinoside	[446]
	Rubia schumanniana	Anthraquinones glycosides: 1,3,6-trihydroxy-2-methyl anthraquinone; (2-methyl-1,3,6-trihydroxy-9,10-anthraquinone-3-O-α-L-rhamnopyranosyl (1→2)-β-d-glucopyranoside); 1-hydroxy-2-hydroxy-methylene-9,10-anthraquinone-11-O-β-d-glucopyranosyl (1→6)-β-d-glucopyranoside; digiferruginol glycoside	[447]
		Triterpenes: 3β-hydroxy-urs-30-p-Z-hydroxycinnamoyl-12-en-28-oic-acid; 3β-hydroxy-olean-30-p-E-hydroxycinnamoyl-12-en-28-oic-acid; 3β,6α-dihydroxy-urs-14-en-12-one	[448]
		Cyclopeptides: rubischumanins A–C; C-6β-oxy-RA IV; RA-IV; O-seco-RA-V	[448]
	Rubia yunnanensis	Triterpene: rubiarbonol K	[449]
	Rubia tinctorum	Anthraquinones: alizarin; lucidin; mollugin; xanthopurpurin; rubiadin	[450]
		Anthraquinones: 1-hydroxy-2-hydroxymethylanthraquinone 3-glucoside 2-hydroxymethyl-anthraquinone 3-glucoside; 3,8-dihydroxymethylanthraquinone 3-glucosideAnthraquinone glycosides: alizarin; lucidian-ω-ethyl ether; lucidin primeverosideIridoid: asperuloside	[451]
		Anthraquinones: pseudopurpurin; lucidin; alizarin; purpurin; alizarin-2-methylether; lucidin-ω-ethylether; nordamnacanthal; munjistin ethyl ester; lucidin primeveroside; ruberithric acid	[452,453]
	Rubia yunnanensis	Cyclic hexapeptides: rubiyunnanins A–B	[454]
		Triterpenes: rubiarbonones D–F; rubiarbosides F–G; rubiarbonone A; rubiarbonol A–B; rubiarbonone B; rubiarbonol A; rubiarbonol B; rubiarbonol F; rubiarbonol G; rubiarboside A	[455]
**	*	Luculia pinciana	Triterpene: luculiaoic acid A	[456]
			Triterpenes: vogeloside; epi-vogeloside; loganoside; loganin; cincholic acid 28-O-β-d-glucopyranosyl ester; cincholic acid-3-O-β-d-glucopyranoside, 28-O-β-d-glucopyranosyl ester; cincholic acid-3-O-β-d-glucopyranoside	[457]

ALB: Alberteae; ARG: Argostemmateae; CHI: Chiococceae; CIN: Cinchoneae; COF: Coffeeae; CON: Condamineeae; COU: Coussareeae; GAR: Gardenieae; GUE: Guettardeae; HAM: Hamelieae; HIL: Hillieae; HYM: Hymenodictyeae; ISE: Isertieae; IXO: Ixoreae; KNO: Knoxieae; LAS: Lasiantheae; MOR: Morindeae; MUS: Mussaendeae; NAU: Naucleeae; OCT: Octotropideae; OPH: Ophiorrhizeae; PAE: Paederieae; PAV: Pavetteae; POS: Posoquerieae; PRI: Prismatomerideae; PSY: Psychotrieae; PUT: Putorieae; RUB: Rubieae; SAB: Sabiceeae; SPE: Spermacoceae; VAN: Vanguerieae. * Genera not allocated to any tribe. ** Genera unclassified to subfamily.

Based on the obtained data, the main occurrence of iridoids, anthraquinones, triterpenes, indole alkaloids and alkaloids belonging to different chemical subclasses, was observed. The chemical profile, as expressed by the occurrence of major categories of secondary metabolites (alkaloids, anthraquinones and iridoids) showed to be quite different for each subfamily. Furthermore, the study of specific classes may contribute to chemotaxonomic correlations, since there are compounds with restricted distribution [54]. These same classes of substances served as a distribution pattern to create and modify plant classification systems as proposed by Dahlgren [54].

In Ixoroideae subfamily, the iridoids are found as chemotaxonomic markers, in Cinchonoideae the indole alkaloids predominate over other substances and in Rubioideae the anthraquinones are the major class of secondary metabolites (Figure 3). These global findings corroborate those found in the Brazilian Rubiaceae chemotaxonomic study by Bolzani [15].

Figure 3

Chemical diversity and major secondary metabolites distribution among Rubiaceae subfamilies observed in this revision. IXO: Ixoroideae, CIN: Cinchonoideae, RUB: Rubioideae.

Other studies also describe indole alkaloids as the class of substances of major occurrence in Cinchonoideae, especially in Guettardeae tribe [50,55]. Studies by Wijinsma and Verpoorte [56] and Bolzani et al. [15] describe the occurrence of standardized chemical markers: iridoids in Ixoroideae; indole alkaloids in Cinchonoideae and anthraquinones in Rubioideae. These data corroborate the one presented in this review.

Therefore, it was observed triterpenes widely distributed in all subfamilies, therefore a chemotaxonomic correlation cannot be established. The occurrence of a common pattern in secondary metabolism may suggest, strongly, taxons having a common ancestor. Thus, if there are morphological similarities, they can either be due to a common ancestry or convergent evolution [54]. Furthermore, the seco-iridoids are iridoids precursors and also participate in the biosynthesis of monoterpene indole alkaloids, so they may be involved in two distinct chemotaxonomic subdivisions [57,58]. Thus, different species may exhibit different chemical substance classes, but having the same precursor, which may indicates a phylogenetic relationship [59,60,61,62,63,64].

This survey found Rubioideae subfamily has the highest chemical diversity in Rubiaceae subfamily. Among the described tribes, the most chemically studied are: Naucleeae (44), Gardenieae (39), Psycotrieae (34), Spermacoceae (35), Rubieae (25) and Ophiorrhizeae (14); other tribes have around five to six studied species. In general, the species with the largest number of phytochemical studies recorded from 1990 to 2014 belong to the genera Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda. Plants from the Psycotrieae tribe were shown to be the major producers of alkaloids, since all phytochemical studies with genera belonging to this tribe (Camptotheca, Carapichea, Cephaelis, Chassalia, Margaritopsis, Palicourea and Psychotria) resulted in the isolation of alkaloids. In the Gardenieae tribe, the presence of iridoids was observed, not only in this survey, but also in other studies [59,60,61,62,64]. Studies showed Rubia, Galium and Morinda genera (subfamily Rubioideae) as important sources of anthraquinones, such as aglycone and rarely glycosides [56].

However, studies establishing a chemotaxonomic classification of plants are quite complex, since there are different types of secondary metabolites that can be distinct in correlated species. These differences in the production of secondary metabolites can be attributed to a number of factors such as genetic mutation, blocking of a biosynthetic pathway and changes in the metabolism due to infection. Soil and climatic variations such as altitude, soil type, macronutrients, micronutrients and water availability, plant age, ultraviolet radiation, rainfall, seasonality and circadian rhythm, also have great influence on the production of metabolites. Besides the fact that the chemical composition can be variable in accordance with the plant organ, it is necessary to study the plant as a whole, to be able to infer a degree of similarity [59,60,61,62,63,64].

Considering the chemical profile of the Rubiaceae family and the metabolic pathways used to produce it, Rubioideae is the most ancient subfamily from an evolutive point of view [16], then it was subdivided into Ixoroideae and finally into Cinchonoideae. The chemical biosynthetic pathway now supports this botanical conclusion. In Rubioideae, anthraquinones are the main metabolites and the pathways are not so specific, being iridoids and indole alkaloids produced also in a large amount. In Ixoroideae, the most active biosysthetic pathway is the one that produces iridoids; while in Cinchonoideae, it is the one that produces indole alkaloids together with other alkaloids.

6. Conclusions

This review has encompassed phytochemical studies of Rubiaceae species for the past 24 years. These substances have been isolated mainly from Uncaria, Psychotria, Hedyotis, Ophiorrhiza and Morinda genera. From the Rubioideae subfamily, 139 species were studied; 80 from the Ixoroideae, and 74 from the Cinchonoideae. Some correlations between iridoids, triterpenes, alkaloids and anthraquinones occurrence and distribution between tribes and subfamilies could be observed, providing chemotaxonomic clues. From an evolutionary point of view, the Rubioideae is the most ancient subfamily [16], then it was subdivided into the Ixoroideae and finally into the Cinchonoideae.