NMR and MS data for novel bioactive constituents from Pugionium cornutum L. Gaertn.

The data presented in this article are associated with the research article entitled "Bioactive Constituents Study of Pugionium cornutum L. Gaertn on Intestinal Motility" [1]. The aim of this data was to provide the 1D, 2D NMR and MS spectrum of novel bioactive compounds from P. cornutum.

Data

The dataset contains raw analysis data obtained through the chemistry research of the dried roots of Mongolian medicinal and edible plant, Pugionium cornutum L. Gaertn. Information about the eight new compounds pugcornols A (1), B (2), C (3), and D (4), pugcornosides A (5), B (6), C (7), and D (8) has been presented in Fig. 1, Fig. 2, Fig. 3, Fig. 4, Fig. 5, Fig. 6, Fig. 7, Fig. 8, Fig. 9, Fig. 10, Fig. 11, Fig. 12, Fig. 13, Fig. 14, Fig. 15, Fig. 16, Fig. 17, Fig. 18, Fig. 19, Fig. 20, Fig. 21, Fig. 22, Fig. 23, Fig. 24, Fig. 25, Fig. 26, Fig. 27, Fig. 28, Fig. 29, Fig. 30, Fig. 31, Fig. 32, Fig. 33, Fig. 34, Fig. 35, Fig. 36, Fig. 37, Fig. 38, Fig. 39, Fig. 40, Fig. 41, Fig. 42, Fig. 43, Fig. 44, Fig. 45.

Fig. 1

1H NMR (500 MHz, DMSO‑d6) spectrum of compound 1.

Fig. 2

13C NMR (125 MHz, DMSO‑d6) spectrum of compound 1.

Fig. 3

DEPT 135 (DMSO‑d6) spectrum of compound 1.

Fig. 4

1H 1H COSY (DMSO‑d6) spectrum of compound 1.

Fig. 5

HSQC (DMSO‑d6) spectrum of compound 1.

Fig. 6

HMBC (DMSO‑d6) spectrum of compound 1.

Fig. 7

HRESI-TOF-MS spectrum of compound 1.

Fig. 8

1H NMR (500 MHz, CD3OD) spectrum of compound 2.

Fig. 9

13C NMR (125 MHz, CD3OD) spectrum of compound 2.

Fig. 10

DEPT 135 (CD3OD) spectrum of compound 2.

Fig. 11

1H 1H COSY (CD3OD) spectrum of compound 2.

Fig. 12

HSQC (CD3OD) spectrum of compound 2.

Fig. 13

HMBC (CD3OD) spectrum of compound 2.

Fig. 14

HRESI-TOF-MS spectrum of compound 2.

Fig. 15

1H NMR (500 MHz, CD3OD) spectrum of compound 3.

Fig. 16

13C NMR (125 MHz, CD3OD) spectrum of compound 3.

Fig. 17

DEPT 135 (CD3OD) spectrum of compound 3.

Fig. 18

1H 1H COSY (CD3OD) spectrum of compound 3.

Fig. 19

HSQC (CD3OD) spectrum of compound 3.

Fig. 20

HMBC (CD3OD) spectrum of compound 3.

Fig. 21

HRESI-TOF-MS spectrum of compound 3.

Fig. 22

1H NMR (500 MHz, CD3OD) spectrum of compound 4.

Fig. 23

13C NMR (125 MHz, CD3OD) spectrum of compound 4.

Fig. 24

DEPT 135 (CD3OD) spectrum of compound 4.

Fig. 25

1H 1H COSY (CD3OD) spectrum of compound 4.

Fig. 26

HSQC (CD3OD) spectrum of compound 4.

Fig. 27

HMBC (CD3OD) spectrum of compound 4.

Fig. 28

HRESI-TOF-MS spectrum of compound 4.

Fig. 29

1H NMR (500 MHz, CD3OD) spectrum of compound 5.

Fig. 30

13C NMR (125 MHz, CD3OD) spectrum of compound 5.

Fig. 31

DEPT 135 (CD3OD) spectrum of compound 5.

Fig. 32

1H 1H COSY (CD3OD) spectrum of compound 5.

Fig. 33

HSQC (CD3OD) spectrum of compound 5.

Fig. 34

HMBC (CD3OD) spectrum of compound 5.

Fig. 35

HRESI-TOF-MS spectrum of compound 5.

Fig. 36

1H NMR (500 MHz, CD3OD) spectrum of compound 6.

Fig. 37

13C NMR (125 MHz, CD3OD) spectrum of compound 6.

Fig. 38

DEPT 135 (CD3OD) spectrum of compound 6.

Fig. 39

1H 1H COSY (CD3OD) spectrum of compound 6.

Fig. 40

HSQC (CD3OD) spectrum of compound 6.

Fig. 41

HMBC (CD3OD) spectrum of compound 6.

Fig. 42

HRESI-TOF-MS spectrum of compound 6.

Fig. 43

1H NMR (500 MHz, CD3OD) spectrum of compound 7.

Fig. 44

13C NMR (125 MHz, CD3OD) spectrum of compound 7.

Fig. 45

DEPT 135 (CD3OD) spectrum of compound 7.

Experimental design, materials, and methods

Study area description

Pugionium cornutum L. Gaertn (PC), Cruciferae family, is widely distributed in the Badain Jaran Desert, Kubuqi Desert, Mu Us Desert, Horqin sandy land, and Hulunbuir sandy land [2]. As the traditional arenicolous Mongolian medicine, PC has accumulated rich experience and knowledge of promoting gastrointestinal motility and improving indigestion [3]. Previously, a further phytochemical investigation on the 70% ethanol-water extract of the roots of P. cornutum led to the isolation and characterization of eight compounds that have been not reported previously. Among them, 1–4 were rare naturally occurring thiohydantoin derivatives. Herein, their structure characterization has been identified by various spectrometry methods including NMR and MS spectra.

Plant material

The roots of Pugionium cornutum L. Gaertn were collected from Alxa Youqi, Inner Mongolia Autonomous region, China, and identified by Dr. Li Tianxiang (Experiment Teaching Department, Tianjin University of Traditional Chinese Medicine). The voucher specimen was deposited at the Academy of Traditional Chinese Medicine of Tianjin University of TCM.

NMR and MS spectrum of the isolates

The dried roots of PC were refluxed with 70% ethanol-water for three times. Evaporation of the solvent under pressure provided a 70% ethanol-water extract, which was partitioned with H2O and EtOAc to gain H2O layer and EtOAc layer partition, respectively. The H2O layer partition was subjected to D101 macroporous resin CC and eluted with H2O, 95% EtOH, and acetone, successively. Then 95% EtOH eluate and EtOAc layer partition was isolated by silica gel, Sephadex LH-20 chromatography columns and preparative HPLC. As results, four new rare thiohydantoin derivatives pugcornols A (1), B (2), C (3), and D (4) [[4], [5], [6], [7]], two new glucosinolates pugcornosides A (5) [[8], [9], [10]], B (6) [10], two new others pugcornosides C (7) [11], D (8) were obtained and identified by using NMR, MS, ECD technologies, as well as chemical reaction.

Pugcornol A (1)

Colorless oil; [α]D25 –31.3 (conc. 0.12, MeOH); CD (conc. 0.0015 M, MeOH) mdeg (λnm): –1.39 (235), −3.33 (256), −3.60 (269); CD (conc. 0.0015 M, CH3CN) mdeg (λnm): –1.21 (229), −2.83 (245), −4.52 (267); UV λmax (MeOH) nm (log ε): 269 (3.81); IR νmax (KBr) cm−1: 3364, 2943, 1750, 1424, 1347, 1225, 1124, 1061, 1025; 1H NMR (DMSO‑d6, 500 MHz) and 13C NMR (DMSO‑d6, 125 MHz) data see Fig. 1, Fig. 2, Fig. 3, Fig. 4, Fig. 5, Fig. 6. HRESI-TOF-MS data see Fig. 7.

Pugcornol B (2)

Colorless oil; [α]D25 –39.3 (conc. 0.12, MeOH); CD (conc. 0.0015 M, MeOH) mdeg (λnm): –1.30 (223), −5.34 (270); CD (conc. 0.0015 M, CH3CN) mdeg (λnm): –1.56 (223), −6.80 (252), −4.81 (272); UV λmax (MeOH) nm (log ε): 277 (3.96); IR νmax (KBr) cm−1: 3355, 2941, 1750, 1428, 1346, 1236, 1133, 1049, 1010; 1H NMR (CD3OD, 500 MHz) and 13C NMR (CD3OD, 125 MHz) data Fig. 8, Fig. 9, Fig. 10, Fig. 11, Fig. 12, Fig. 13. HRESI-TOF-MS data see Fig. 14.

Pugcornol C (3)

Colorless oil; [α]D25 –36.1 (conc. 0.14, MeOH); CD (conc. 0.0015 M, MeOH) mdeg (λnm): –0.34 (228), −2.60 (253), −2.99 (269); CD (conc. 0.0015 M, CH3CN) mdeg (λnm): –1.26 (231), −3.91 (250), −5.16 (267); UV λmax (MeOH) nm (log ε): 249 (3.50), 268 (3.58); IR νmax (KBr) cm−1: 3365, 2935, 1749, 1419, 1347, 1236, 1133, 1050, 1015; 1H NMR (CD3OD, 500 MHz) and 13C NMR (CD3OD, 125 MHz) data Fig. 14, Fig. 15, Fig. 16, Fig. 17, Fig. 18, Fig. 19, Fig. 20. HRESI-TOF-MS data see Fig. 21.

Pugcornol D (4)

Colorless oil; [α]D25 –64.1 (conc. 0.13, MeOH); CD (conc. 0.0015 M, MeOH) mdeg (λnm): –35.54 (214), +14.06 (238), +0.12 (263); CD (conc. 0.0015 M, CH3CN) mdeg (λnm): –33.13 (212), 12.47 (238), +0.23 (262); UV λmax (MeOH) nm (log ε): 214 (3.44), 267 (2.38); IR νmax (KBr) cm−1: 3420, 2943, 1765, 1701, 1447, 1419, 1361, 1014; 1H NMR (CD3OD, 500 MHz) and 13C NMR (CD3OD, 125 MHz) data Fig. 22, Fig. 23, Fig. 24, Fig. 25, Fig. 26, Fig. 27. HRESI-TOF-MS data see Fig. 28.

Pugcornoside A (5)

White powder; [α]D25 –23.2 (conc. 0.11, MeOH); UV λmax (MeOH) nm (log ε): 223 (3.61), 277 (3.18); IR νmax (KBr) cm−1: 3365, 2922, 1646, 1558, 1507, 1457, 1277, 1070; 1H NMR (CD3OD, 500 MHz) and 13C NMR (CD3OD, 125 MHz) data Fig. 29, Fig. 30, Fig. 31, Fig. 32, Fig. 33, Fig. 34. HRESI-TOF-MS data see Fig. 35.

Pugcornoside B (6)

White powder; [α]D25 –52.6 (conc. 0.13, MeOH); UV λmax (MeOH) nm (log ε): 220 (3.65), 277 (3.18); IR νmax (KBr) cm−1: 3366, 2918, 1600, 1507, 1456, 1436, 1278, 1045, 1072; 1H NMR (CD3OD, 500 MHz) and 13C NMR (CD3OD, 125 MHz) data Fig. 36, Fig. 37, Fig. 38, Fig. 39, Fig. 40, Fig. 41. HRESI-TOF-MS data see Fig. 42.

Pugcornoside C (7)

White powder; [α]D25 +6.3 (conc. 0.12,MeOH); UV λmax (MeOH) nm (log ε): 266 (2.94); IR νmax (KBr) cm−1: 3386, 2391, 1734, 1652, 1107, 1044; 1H NMR (CD3OD, 500 MHz) and 13C NMR (CD3OD, 125 MHz) data Fig. 43, Fig. 44, Fig. 45, Fig. 46, Fig. 47, Fig. 48. HRESI-TOF-MS data see Fig. 49.

Fig. 46

1H 1H COSY (CD3OD) spectrum of compound 7.

Fig. 47

HSQC (CD3OD) spectrum of compound 7.

Fig. 48

HMBC (CD3OD) spectrum of compound 7.

Fig. 49

HRESI-TOF-MS spectrum of compound 7.

Pugcornoside D (8)

White powder; [α]D25 +28.1 (conc. 0.12, MeOH); UV λmax (MeOH) nm (log ε): 205 (3.72), 262 (2.77); IR νmax (KBr) cm−1: 3420, 2933, 1733, 1635, 1466, 1339, 1267, 1154, 1112, 1047; 1H NMR (CD3OD, 500 MHz) and 13C NMR (CD3OD, 125 MHz) data Fig. 50, Fig. 51, Fig. 52, Fig. 53, Fig. 54, Fig. 55. HRESI-TOF-MS data see Fig. 56.

Fig. 50

1H NMR (500 MHz, CD3OD) spectrum of compound 8.

Fig. 51

13C NMR (125 MHz, CD3OD) spectrum of compound 8.

Fig. 52

DEPT 135 (CD3OD) spectrum of compound 8.

Fig. 53

1H 1H COSY (CD3OD) spectrum of compound 8.

Fig. 54

HSQC (CD3OD) spectrum of compound 8.

Fig. 55

HMBC (CD3OD) spectrum of compound 8.

Fig. 56

HRESI-TOF-MS spectrum of compound 8.

Specifications Table

Subject	Chemistry
Specific subject area	Natural products research
Type of data	Figure
How data were acquired	First, the compounds were isolated from the 70% ethanol-water extract of P. cornutum roots. Then the samples were dissolved in DMSO‑d6 or CD3OD before NMR test.
Data format	Raw and Analyzed
Parameters for data collection	The NMR spectra data parameters including chemical shift δ-values and coupling constant (J). The MS spectra data parameters including m/z.
Description of data collection	NMR spectra data of novel compounds from the roots of P. cornutum were recorded on a Bruker Advance-500 spectrometer using standard Bruker pulse programs (Bruker, Karlsruhe, Germany). Chemical shifts were shown as δ-values with reference to tetramethylsilane (TMS) as an internal standard. Positive- and negative-ion HRESI-TOF-MS of novel compounds from P. cornutum roots were recorded on an Agilent Technologies 6520 Accurate-Mass Q-Tof LC/MS spectrometer.
Data source location	Tianjin State Key Laboratory of Modern Chinese Medicine, Tianjin, China
Data accessibility	Data is with the article [1]
Related research article	W. Shi, J. Ruan, Y. Guo, Z. Ding, J. Yan, L. Qu, C. Zheng, Y. Zhang, T. Wang, Bioactive constituents study of Pugionium cornutum L. Gaertn on intestinal motility, Fitoerapia, 138 (2019) 104291.

Value of the Data• NMR and MS data of novel compounds is important for elucidating their chemical structures. • NMR and MS data of novel thiohydantoin derivatives is useful for the elucidating their chemical analogues. • This information will allow comparisons across different thiohydantoin derivatives and other new compounds from Pugionium species or Cruciferae family plant sources.