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Cha, Kim, Lee, Subedi, Kim, and Lee: Phytochemical Constituents of Capsella bursa-pastoris and Their Anti-inflammatory Activity
Original Article

Natural Product Sciences 2018;24(2):132-138.

Published online: 20 January 2018

DOI: https://doi.org/10.20307/nps.2018.24.2.132

Phytochemical Constituents of Capsella bursa-pastoris and Their Anti-inflammatory Activity

Joon Min Cha1, Dong Hyun Kim1, Tae Hyun Lee1, Lalita Subedi2, Sun Yeou Kim2, Kang Ro Lee1, ∗

1Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, 2066 Seobu-Ro, Jangan-gu, Suwon, Gyeonggi-do 440–746, Republic of Korea

2Gachon Institute of Pharmaceutical Science, Gachon University, 191 Hambakmoero, Yeonsu-gu, Incheon 21936, Republic of Korea

∗Author for correspondence Kang Ro Lee, Natural Products Laboratory, School of Pharmacy, Sungkyunkwan University, 2066Seobu-Ro, Jangan-ku, Suwon, Gyeonggi-do 440-746, Republic of Korea. Tel: +82-31-290-7710; E-mail: krlee@skku.edu

Received 7 February 2018       Revised 2 April 2018       Accepted 2 April 2018

Copyright © 2018 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 – 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-β-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S, 5R, 6S, 7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), β-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-β-D-glucopyranoside (10), pinoresinol-4'-O-β-D-glucopyranoside (11), luteolin (12), quercetin-3-O-β-D-glucopyranoside (13), and luteolin 6-C-β-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 – 14 were for the first time reported from this plant source. The antiinflammatory effects of 1 – 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with IC50 values of 9.70 µM.

Keywords: Capsella bursa-pastoris, Cruciferae, Sulfur compound

References

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Fig. 1.
The structures of 1 – 14 isolated from C. bursa-pastoris.
nps-24-132f1.tif
Table 1.
1H and 13C NMR data of 1 in CD3OD (δ in ppm, 700 MHz for 1H and 175 MHz for 13C)
Position 1
δH (J in Hz) δC
1 4.37 d (9.4) 92.3
2 3.50m 72.8
3 3.40t (8.8) 79.6
4 3.30 m 71.6
5 3.30 m 82.61
6 3.64 dd (12.0, 5.5) 63.2
  3.86 dd (12.0, 1.8) 63.2
S-CH3 2.50 m 24.9

a1 H and

13 C NMR data were recorded at 700 and 175 MHz, respectively. Coupling constants (in Hz) are given in parentheses.

Table 2.
1H and 13C NMR data of 2 and 3 in CDCl3 (δ in ppm, 700 MHz for 1H and 175MHz for 13C)
Position 2 3
δH (J in Hz) δC δH (J in Hz) δC
1   119.8   119.9
2 2.28 t (7.0) 17.1 2.32t (7.1) 17.2
3 1.59 m 25.3 1.64m 25.3
4 1.23–1.30 m 28.9 1.25–1.29 m 29.2
5 1.38 m 28.6 1.38 m 28.8
6 1.38 m 28.7 1.38 m 28.9
7 1.23–1.30 m 28.5 1.25–1.29 m 28.7
8 1.23–1.30 m 29.0 1.25–1.29 m 28.7
9 1.70 m 22.5 1.25–1.29 m 29.3
10 2.66 m 54.7 1.74 m 22.6
  2.58 m      
11     2.73 m 54.6
      2.65 m  
CH3SO 2.51 s 38.6 2.57 s 38.6

a1 H and

13 C NMR data were recorded at 700 and 175 MHz, respectively. Coupling constants (in Hz) are given in parentheses.

Table 3.
Effects of compounds 1 – 14 on NO production in LPS-activated BV-2 cells
Compound IC50a (mM) Cell viability b (%)
1 44.10 118.28 ± 6.54
2 75.23 136.44 ± 5.13
3 144.64 117.91 ± 8.44
4 32.60 136.20 ± 11.20
5 153.71 152.92 ± 3.50
6 167.24 117.44 ± 2.83
7 >500 114.70 ± 8.48
8 77.12 119.36 ± 6.1
9 259.50 135.42 ± 10.68
10 63.55 112.15 ± 2.94
11 266.61 107.41 ± 2.63
12 9.70 137.66 ± 3.11
13 77.17 119.36 ± 6.13
14 146.69 120.36 ± 3.88
cL-NMMA 17.40 110.21 ± 4.56

a The IC50 value of each compound was defined as the concentration (μM) that caused 50% inhibition of NO production in LPS-activated BV-2 cells;

b Cell viability after treatment with 20 μM of each compound was determined by the MTT assay and is expressed as a percentage (%). The results are averages of three independent experiments, and the data are expressed as mean ± SD;

c L-NMMA was used as a positive control

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