Literature DB >> 17851404

Occurrence, biological activities and synthesis of kaurane diterpenes and their glycosides.

Pablo Anselmo García1, Alaíde Braga de Oliveira, Ronan Batista.   

Abstract

This paper presents a review on kaurane diterpenes and their glycoside derivatives, covering aspects of their occurrence, biological activities and the synthesis of these natural products and their analogues. First, it shows and classifies diterpenes, in accordance with the already established structural criteria in the literature. Then, kaurane diterpenes are presented, focusing on their chemical structures, occurrence in the plant kingdom and their main, recently described, biological activities. Moreover, the most significant works, published between 1964 and November 2006, which describe the total synthesis or structural transformations of some kaurane diterpenes, including either semisynthetic and/or microbiological methodologies, are consisely reviewed. At this point, some general considerations on glycosides are introduced, and kaurane glycosides are presented and discussed on the basis of their toxic importance and occurrence in the plant kingdom, having focused on related aspects of their biological activities and the relationships between these activities and the structural factors of their molecules. Finally, the principal methods of glycosidation by enzymatic and chemical processes are both presented, and a few papers on the synthesis of kaurane glycosides are succinctly discussed.

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Year:  2007        PMID: 17851404      PMCID: PMC6149336          DOI: 10.3390/12030455

Source DB:  PubMed          Journal:  Molecules        ISSN: 1420-3049            Impact factor:   4.411


  85 in total

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Journal:  Adv Biochem Eng Biotechnol       Date:  1997       Impact factor: 2.635

2.  Biotransformation of methyl ent-17-hydroxy-16beta-kauran-19-oate by Rhizopus stolonifer.

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Journal:  Appl Microbiol Biotechnol       Date:  2000-05       Impact factor: 4.813

3.  An anti-inflammatory ent-kaurane from the stems of Annona squamosa that inhibits various human neutrophil functions.

Authors:  Shang-Hsin Yeh; Fang-Rong Chang; Yang-Chang Wu; Yu-Liang Yang; Shi-Kai Zhuo; Tsong-Long Hwang
Journal:  Planta Med       Date:  2005-10       Impact factor: 3.352

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Journal:  J Nat Prod       Date:  1984 Nov-Dec       Impact factor: 4.050

5.  Cardiovascular and diuretic activity of kaurene derivatives of Xylopia aethiopica and Alepidea amatymbica.

Authors:  L I Somova; F O Shode; K Moodley; Y Govender
Journal:  J Ethnopharmacol       Date:  2001-10       Impact factor: 4.360

6.  Six new diterpenoids from Suregada multiflora.

Authors:  Ismet Ara Jahan; Nilufar Nahar; M Mosihuzzaman; Farzana Shaheen; M Iqbal Choudhary
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

7.  Ponicidin, an ent-kaurane diterpenoid derived from a constituent of the herbal supplement PC-SPES, Rabdosia rubescens, induces apoptosis by activation of caspase-3 and mitochondrial events in lung cancer cells in vitro.

Authors:  Jia Jun Liu; Ren Wei Huang; Dong Jun Lin; Jun Peng; Maohong Zhang; Xianglin Pan; Ming Hou; Xiang Yuan Wu; Qu Lin; Feng Chen
Journal:  Cancer Invest       Date:  2006-03       Impact factor: 2.176

Review 8.  Stevioside.

Authors:  Jan M C Geuns
Journal:  Phytochemistry       Date:  2003-11       Impact factor: 4.072

9.  Purification and characterization of an extremely thermostable beta-glucosidase from the hyperthermophilic archaeon Pyrococcus furiosus.

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Journal:  Eur J Biochem       Date:  1993-04-01

10.  Further study on the 1,4-alpha-transglucosylation of rubusoside, a sweet steviol-bisglucoside from Rubus suavissimus.

Authors:  K Ohtani; Y Aikawa; H Ishikawa; R Kasai; S Kitahata; K Mizutani; S Doi; M Nakaura; O Tanaka
Journal:  Agric Biol Chem       Date:  1991-02
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  16 in total

1.  Geopyxins A-E, ent-kaurane diterpenoids from endolichenic fungal strains Geopyxis aff. majalis and Geopyxis sp. AZ0066: structure-activity relationships of geopyxins and their analogues.

Authors:  E M Kithsiri Wijeratne; Bharat P Bashyal; Manping X Liu; Danilo D Rocha; G M Kamal B Gunaherath; Jana M U'Ren; Malkanthi K Gunatilaka; A Elizabeth Arnold; Luke Whitesell; A A Leslie Gunatilaka
Journal:  J Nat Prod       Date:  2012-01-20       Impact factor: 4.050

2.  Extracts of Sideritis scardica as triple monoamine reuptake inhibitors.

Authors:  Rainer Knörle
Journal:  J Neural Transm (Vienna)       Date:  2012-05-24       Impact factor: 3.575

Review 3.  Structural and Chemical Biology of Terpenoid Cyclases.

Authors:  David W Christianson
Journal:  Chem Rev       Date:  2017-08-25       Impact factor: 60.622

4.  ent-Kaurane glycosides from Tricalysia okelensis.

Authors:  Wen-Hui Xu; Melissa Ruth Jacob; Ameeta Kishore Agarwal; Alice Mae Clark; Zong-Suo Liang; Xing-Cong Li
Journal:  Chem Pharm Bull (Tokyo)       Date:  2010-02       Impact factor: 1.645

5.  The enantioselective construction of tetracyclic diterpene skeletons with Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation reactions.

Authors:  Sarah J Burke; William P Malachowski; Sharan K Mehta; Roselyn Appenteng
Journal:  Org Biomol Chem       Date:  2015-03-07       Impact factor: 3.876

Review 6.  Applications of Friedel-Crafts reactions in total synthesis of natural products.

Authors:  Majid M Heravi; Vahideh Zadsirjan; Pegah Saedi; Tayebeh Momeni
Journal:  RSC Adv       Date:  2018-12-03       Impact factor: 4.036

7.  ent-Kaurane-based regio- and stereoselective inverse electron demand hetero-Diels-Alder reactions: synthesis of dihydropyran-fused diterpenoids.

Authors:  Chunyong Ding; Lili Wang; Haijun Chen; Christopher Wild; Na Ye; Ye Ding; Tianzhi Wang; Mark A White; Qiang Shen; Jia Zhou
Journal:  Org Biomol Chem       Date:  2014-11-14       Impact factor: 3.876

Review 8.  Ethnobotany and the Role of Plant Natural Products in Antibiotic Drug Discovery.

Authors:  Gina Porras; François Chassagne; James T Lyles; Lewis Marquez; Micah Dettweiler; Akram M Salam; Tharanga Samarakoon; Sarah Shabih; Darya Raschid Farrokhi; Cassandra L Quave
Journal:  Chem Rev       Date:  2020-11-09       Impact factor: 60.622

9.  Anti-allodynic and Anti-hyperalgesic effects of an ethanolic extract and xylopic acid from the fruits of Xylopia aethiopica in murine models of neuropathic pain.

Authors:  Elvis O Ameyaw; Eric Woode; Eric Boakye-Gyasi; Wonder K M Abotsi; James Oppong Kyekyeku; Reimmel K Adosraku
Journal:  Pharmacognosy Res       Date:  2014-04

10.  Analgesic effects of an ethanol extract of the fruits of Xylopia aethiopica (Dunal) A. Rich (Annonaceae) and the major constituent, xylopic acid in murine models.

Authors:  Eric Woode; Elvis O Ameyaw; Eric Boakye-Gyasi; Wonder K M Abotsi
Journal:  J Pharm Bioallied Sci       Date:  2012-10
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