Pharmacognosy Magazine

ORIGINAL ARTICLE
Year
: 2020  |  Volume : 16  |  Issue : 71  |  Page : 564--567

Chemical constituents from Saussurea pachyneura


Shuo Zhang1, Xiao-Man Tu1, Wan-Chang Zhang1, Guang-Bo Xie2,  
1 Department of Biotechnology, School of Life Science and Technology, University of Electronic Science and Technology of China, Chengdu, China
2 Department of Biotechnology, School of Life Science and Technology; Center for Informational Biology, University of Electronic Science and Technology of China, Chengdu, China

Correspondence Address:
Guang-Bo Xie
Department of Biotechnology, School of Life Science and Technology, University of Electronic Science and Technology of China, Chengdu 610054
China

Abstract

Background: Genus Saussurea is famous for its use in traditional Chinese medicine. Objectives: Saussurea pachyneura, a plant from genus Saussurea, was studied for its secondary metabolites. Materials and Methods: The air-dried whole plant material was extracted by ethanol. The compounds from the ethanolic extract were isolated and purified by silica gel, octadecylsilyl-silica gel, and Sephadex LH-20 column chromatography. Their structures were identified based on the spectral analysis. Results: A total of 13 compounds, including a new long-chain fatty acid ester (4), were isolated and identified from the ethanolic extract of S. pachyneura. Conclusion: This is the first study to report the phytochemical analysis of S. pachyneura and also the first study to isolate the compounds from ethanolic extract of the whole plant material of S. pachyneura.



How to cite this article:
Zhang S, Tu XM, Zhang WC, Xie GB. Chemical constituents from Saussurea pachyneura.Phcog Mag 2020;16:564-567


How to cite this URL:
Zhang S, Tu XM, Zhang WC, Xie GB. Chemical constituents from Saussurea pachyneura. Phcog Mag [serial online] 2020 [cited 2021 Jan 23 ];16:564-567
Available from: http://www.phcog.com/text.asp?2020/16/71/564/298692


Full Text



SUMMARY

  • The phytochemical investigation of the whole plant of Saussurea pachyneura DC resulted in the isolation of 13 compounds
  • These compounds include four phenylpropanoids (compounds 8–10, 12), three long-chain fatty acids/esters (compounds 1, 4, and 5), three steroids (compounds 3, 11, and 13), two triterpenoids (compounds 6 and 7), and one enyne (compound 2)
  • Compound 4 has been identified as a new long-chain fatty acid ester
  • This is the first phytochemical study on S. pachyneura.


[INLINE:1]

Abbreviations used: NMR: Nuclear magnetic resonance; HR-ESI-MS: High-resolution electrospray ionization mass spectrometry; CC: Column chromatography

 Introduction



Genus Saussurea DC. (Compositae) comprises approximately 400 species worldwide, and among them, approximately 264 species are distributed in China.[1] The roots, flowers, leaves, and whole plants of many Saussurea species have been used as traditional Tibetan medicine in China to treat rheumatoid arthritis, traumatic injury, gynecological diseases, altitude stress, and so on.[2]

Saussurea pachyneura Franch., a perennial herb from genus Saussurea, is mainly distributed on the hillside, scrub, meadow, and gravel area of the Hengduan Mountains, China, at an altitude of 3285–4700 m.[1] To date, there is no phytochemical data available in the literature on S. pachyneura. As a continuation of our phytochemical studies on medicinal plants collected in Tibetan area,[3],[4],[5],[6],[7] we conducted research on S. pachyneura. In this study, we report the isolation and structural elucidation of the 13 compounds isolated from the whole plant of S. pachyneura [Figure 1], including a new compound, ethyl (9Z,11E)-13-hydroxy-9,11-octadecadienoate (4).{Figure 1}

 Materials and Methods



General

Nuclear magnetic resonance (NMR) spectra were recorded on Bruker AV II-400 and 600 spectrometers with tetramethylsilane as an internal standard. Melting points were measured on an X-4 digital display micro melting point apparatus and uncorrected. High-resolution electrospray ionization mass spectrometry (HR-ESI-MS) was acquired on a Waters Q-TOF Premier. Column chromatography (CC) was conducted using silica gel (Qingdao Marine Chemical Industry, 200–300 mesh), octadecylsilyl-silica gel (YMC, aperture 120 Š, particle size 50 μm), and Sephadex LH-20 (GE Healthcare). All reagents and solvents used in the separation and purification of compounds were of analytical grade and were purchased from local firms.

Plant material

The whole plant material of S. pachyneura was collected in August 2016 from Zheduo Mountain, Kangding County, Sichuan Province, China. The plant was identified by Prof. Qin-Mao Fang, Institute of Traditional Chinese medicine Medicinal Resources and Cultivation, Sichuan Academy of Chinese Medicine Science. A voucher specimen (No. SP 1608) has been deposited in the School of Life Science and Technology, University of Electronic Science and Technology of China.

Extraction and isolation

The air-dried whole plant material of S. pachyneura (6 kg) was powdered and extracted with 95% aqueous ethanol at room temperature (3 × 10 L, up to 7 days). The solvent was evaporated in vacuo to yield ethanolic extract, which was suspended in distilled water (9 L) and then extracted with EtOAc (3 × 10 L). The EtOAc extract (90 g) was subjected to CC over silica gel (200–300 mesh, 2 kg) and eluted with a gradient solvent system (petroleum ether: EtOAc, 120:1–1:1) to yield 20 fractions (Fr. 1–20). Fraction 5 (1.1 g) was separated by silica gel chromatography (cyclohexane: acetone, 30:1) to yield 10 subfractions (Sub-Fr. 5-1–5-10). Subfraction 5-4 (86 mg) was purified by Sephadex LH-20 CC (CHCl3:MeOH, 2:1) to yield compound 1 (67 mg). Subfraction 5–6 (320 mg) was separated by silica gel chromatography (cyclohexane: acetone, 50:1) and purified on Sephadex LH-20 CC (CHCl3:MeOH, 2:1) to yield compound 2 (12 mg). Subfraction 5–8 (420 mg) was isolated by silica gel chromatography (cyclohexane: acetone, 50:1) and Sephadex LH-20 CC (CHCl3:MeOH, 2:1) and subsequently recrystallized (CHCl3:MeOH, 2:1) to yield compound 3 (51 mg). Fraction 8 (1.3 g) was isolated by silica gel chromatography (cyclohexane: acetone, 70:1), Sephadex LH-20 CC (CHCl3:MeOH, 2:1), and preparative thin-layer chromatography (TLC) (cyclohexane: acetone, 5:1) to yield compound 4 (13 mg). Fraction 9 was isolated by silica gel chromatography (cyclohexane: EtOAc, 40:1–30:1) and preparative TLC (CHCl3:acetone, 20:1) and then purified on Sephadex LH-20 CC (CHCl3:MeOH, 2:1) to yield compound 5 (1.5 mg). Fraction 11 (1.3 g) was isolated by silica gel chromatography (cyclohexane: EtOAc, 15:1) and recrystallized (petroleum ether); the crystals were then purified by Sephadex LH-20 CC (CHCl3:MeOH, 2:1) to yield compounds 6 and 7 (15 mg). Fraction 13 (1.0 g) was isolated by silica gel chromatography (cyclohexane: EtOAc, 15:1) and octadecylsilyl-silica gel chromatography (MeOH) and then purified on Sephadex LH-20 (CHCl3:MeOH, 2:1) to yield compound 8 (4.2 mg). Fraction 14 (766 mg) was isolated by silica gel chromatography (cyclohexane: EtOAc, 15:1–10:1) and recrystallized (cyclohexane). Subsequently, the crystals were purified by Sephadex LH-20 (CHCl3:MeOH, 2:1) to yield compound 9 (8.9 mg). Fraction 15 (1.1 g) was isolated by silica gel chromatography (cyclohexane: EtOAc, 8:1) to yield 10 subfractions (Sub-Fr. 15-1–15-10). Compound 10 (7.8 mg) was obtained from subfraction 15-5 by recrystallization (petroleum ether) and by isolation via Sephadex LH-20 CC (CHCl3:MeOH, 2:1). Compound 11 (2.3 mg) was obtained from subfraction 15-8 by octadecylsilyl-silica gel chromatography (MeOH). Fraction 16 (1.0 g) was isolated by silica gel chromatography (cyclohexane: acetone, 7:1–3:1) and purified by Sephadex LH-20 CC (CHCl3:MeOH, 2:1) to yield compound 12 (10 mg). Fraction 18 (2.0 g) was isolated by silica gel chromatography (cyclohexane: EtOAc, 5:1) and octadecylsilyl-silica gel chromatography (MeOH) to yield compound 13 (23.7 mg).

 Results



New compound

Compound 4 was isolated as a white amorphous powder. Its molecular formula was determined to be C20H36O3 on the basis of HR-ESI-MS (m/z: [M + Na] + calc. 347.2562; found 347.2563) and its13 C-NMR spectroscopic data, indicated three degrees of unsaturation.

Analysis of the1 H and13 C NMR spectra of compound 4 [Table 1] showed a set of unsaturated fatty acid ester signals, one cis-olefin (δH5.43 [1H, dt, J = 7.6, 10.7 Hz], δC132.8; δH5.97 [1H, t, J = 10.9 Hz], δC127.8), one trans-olefin (δH6.48 [1H, dd, J = 11.0, 15.1 Hz], δC125.7; δH5.66 [1H, dd, J = 6.8, 15.2 Hz], δC135.9), one oxygen-bearing methine group (δH4.15 [1H, q, J = 6.5 Hz], δC72.9), one ethoxy group (δH4.12 [2H, q, J = 7.0 Hz], δC60.1; δH1.25 [3H, t, J = 7.0 Hz], δC14.2), one ester carbonyl group (δC173.9), one methyl group (δH0.88 [3H, t, J = 6.7 Hz], δC14.0), and a series of methylene groups (δH2.28 [2H, t, J = 7.5 Hz], δC34.3; δH2.17 [2H, m], δC27.8; δH1.30–1.61 [18H, m], δC37.3, 31.7, 29.4, 29.0, 29.0, 28.9, 25.1, 24.9, 22.6). A proton spin system (-CH2-CH (OH)-CH = CH-CH = CH-CH2-) was deduced from the1 H-1 H COSY spectra [Figure 2]. These NMR data were similar with (9Z,11E)-13-hydroxy-9,11-octadecadienoic acid,[8] an oxidation product of linoleic acid, except for the presence of one more ethoxy group, which indicated that compound 4 was the ethyl ester of (9Z,11E)-13-hydroxy-9,11-octadecadienoic acid. The comparison of NMR data between compound 4 and methyl (9Z,11E,13S)- 13-hydroxy-9,11-octadecadienoate further confirmed this deduction.[9],[10] Thus, the structure of compound 4 was elucidated and named as ethyl (9Z,11E)-13-hydroxy-9,11-octadecadienoate.{Table 1}{Figure 2}

Known compounds

Compound 1: Pale yellow oil.1 H NMR (400 MHz, CDCl3): δH5.35 (4H, m, H-9, 10, 12, 13), 2.77 (2H, t, J = 6.6 Hz, H-11), 2.34 (2H, t, J = 7.4 Hz, H-2), 2.04 (4H, dd, J = 6.8, 13.6 Hz, H-8 and 14), 1.63 (2H, m, H-3), 1.25–1.31 (14H, m, 7 × CH2), 0.88 (3H, t, J = 6.8 Hz, H-18);13 C NMR (100 MHz, CDCl3): δC180.5 (C-28), 130.2 (C-9), 130.0 (C-13), 128.0 (C-10), 127.9 (C-12), 34.1 (C-2), 31.5 (C-16), 29.6 (C-7), 29.3 (C-15), 29.1 (C-4), 29.1 (C-5), 29.0 (C-6), 27.2 (C-14), 27.2 (C-8), 25.6 (C-11), 24.6 (C-3), 22.6 (C-17), 14.0 (C-18). By comparing the NMR data of compound 1 with those reported in the literature,[11] it was identified as linoleic acid.

Compound 2: Yellow oil.1 H NMR (400 MHz, CDCl3): δH5.81 (1H, ddt, J = 17.0, 10.2, 6.6 Hz, H-2), 5.00 (1H, ddd, J = 17.1, 3.6, 1.6 Hz, H-1), 4.93 (1H, dm, J = 10.1 Hz, H-1), 3.63 (1H, dt, J = 7.7, 5.1 Hz, H-8), 3.60 (1H, d, J = 4.0 Hz, H-10), 3.04 (1H, dd, J = 8.0, 4.0 Hz, H-9), 2.26 (2H, t, J = 7.0 Hz, H-15), 2.06 (2H, dd, J = 13.8, 6.7 Hz, H-3), 1.62 (2H, m, H-7), 1.56 (2H, q, J = 7.1 Hz, H-16), 1.52 (1H, m, H-6), 1.40 (4H, m, H-4 and H-5), 1.37 (1H, m, H-6), 0.99 (3H, t, J = 7.3 Hz, H-17).13 C-NMR (100 Hz, CDCl3): δC139.0 (C-2), 114.2 (C-1), 81.9 (C-14)*, 71.4 (C-13)*, 71.4 (C-8), 69.4 (C-11)*, 64.3 (C-12)*, 61.6 (C-9), 45.2 (C-10), 33.7 (C-3), 33.0 (C-7), 28.9 (C-5), 28.7 (C-4), 24.6 (C-6), 21.5 (C-16), 21.2 (C-15), 13.4 (C-17). (*may be interchanged). By comparing the NMR data of compound 2 with those reported in literature,[12] it was identified and named saupachynol.

Compound 3: Colorless needle (petroleum ether).1 H NMR (400 MHz, CDCl3): δH5.35 (1H, m, H-6), 3.52 (1H, m, H-3), 1.00 (3H, s, H-19), 0.92 (3H, d, J = 6.5 Hz, H-21), 0.84 (3H, t, J = 7.6 Hz, H-29), 0.83 (3H, d, J = 7.1 Hz, H-26), 0.81 (3H, d, J = 6.8 Hz, H-27), 0.67 (3H, s, H-18);13 C NMR (100 MHz, CDCl3): δC140.7 (C-5), 121.7 (C-6), 71.8 (C-3), 56.7 (C-14), 56.0 (C-17), 50.1 (C-9), 45.8 (C-24), 42.3 (C-4), 42.3 (C-13), 39.7 (C-12), 37.2 (C-1), 36.5 (C-10), 36.1 (C-20), 33.9 (C-22), 31.9 (C-7), 31.9 (C-8), 31.6 (C-2), 29.1 (C-25), 28.2 (C-16), 24.3 (C-15), 23.0 (C-28), 21.0 (C-11), 19.8 (C-26), 19.4 (C-19), 19.0 (C-27), 18.7 (C-21), 12.0 (C-18), 11.8 (C-29). By comparing the NMR data of compound 3 with those reported in the literature,[13] it was identified as β-sitosterol.

Compound 5: White amorphous powder. HR-ESI-MS (negative) m/z 283.2620 [M-H]-, cald. for C18H35O2, 283.2637.1 H NMR (400 MHz, CDCl3): δH1.58 (2H, m, H-2), 1.25 (30H, m, 15 × CH2), 0.88 (3H, m, H-18). NMR and MS data comparison of compound 5 with those reported in the literature,[14] together with the comparison between compound 5 and standard in three different developing solvents (cyclohexane: EtOAc, 8:1; cyclohexane: acetone, 8:1; CHCl3:EtOAc, 20:1) confirmed that compound 5 was octadecanoic acid.

Mixture of compounds 6 and 7: White amorphous powder. NMR spectra data for compound 6:1 H NMR (400 MHz, DMSO-d 6): δH5.12 (1H, m, H-12), 2.99 (1H, m, H-3), 1.23, 1.03, 0.91, 0.89, 0.86, 0.74, 0.67 (each 3H, s, 7 × CH3);13 C NMR (100 MHz, CDCl3+ CD3 OD): δC180.6 (C-28), 143.8 (C-13), 122.2 (C-12), 78.6 (C-3), 55.2 (C-5), 47.5 (C-9), 46.3 (C-17), 45.9 (C-19), 41.2 (C-14), 39.4 (C-18), 39.1 (C-8), 38.6 (C-1), 38.6 (C-4), 36.9 (C-10), 33.8 (C-21), 33.0 (C-29), 32.6 (C-7), 32.5 (C-22), 30.5 (C-20), 27.9 (C-23), 27.8 (C-15), 27.6 (C-2), 26.6 (C-27), 23.4 (C-30), 23.3 (C-16), 22.9 (C-11), 18.2 (C-6), 16.8 (C-26), 15.4 (C-24), 15.2 (C-25). NMR spectra data for compound 7:

1 H NMR (400 MHz, DMSO-d 6): δH5.12 (1H, m, H-12), 2.99 (1H, m, H-3), 1.03, 0.89, 0.86, 0.74, 0.67 (each 3H, s, 5 × CH3), 0.90 (3H, d, J = 7.0 Hz, CH3), 0.81 (3H, d, J = 6.4 Hz, CH3);13 C NMR (100 MHz, CDCl3+ CD3 OD): δC180.6 (C-28), 138.1 (C-13), 125.4 (C-12), 78.6 (C-3), 55.2 (C-5), 52.8 (C-18), 47.7 (C-9), 47.5 (C-17), 41.2 (C-14), 39.4 (C-8), 39.1 (C-4), 39.0 (C-19), 38.6 (C-1), 38.4 (C-20), 36.9 (C-10), 36.7 (C-22), 33.0 (C-7), 30.5 (C-21), 27.9 (C-2), 27.6 (C-15), 27.6 (C-23), 23.2 (C-27), 22.9 (C-11), 20.9 (C-30), 18.2 (C-6), 16.8 (C-16), 16.7 (C-26), 16.6 (C-29), 15.4 (C-24), 15.1 (C-25). The mixture of compounds 6 and 7 was compared with standard samples (oleanolic acid and ursolic acid) by special TLC method, together with the comparison of NMR data with those reported in literature.[7] The comparison revealed that the mixture contained oleanolic acid and ursolic acid.

Compound 8: Yellow amorphous powder.1 H NMR (400 MHz, CDCl3): δH9.65 (1H, d, J = 7.7 Hz, H-9), 7.40 (1H, d, J = 15.8 Hz, H-7), 7.12 (1H, dd, J = 8.2, 1.9 Hz, H-6), 7.07 (1H, d, J = 1.8 Hz, H-2), 6.96 (1H, d, J = 8.2 Hz, H-5), 6.59 (1H, dd, J = 7.7, 15.8 Hz, H-8), 3.95 (3H, s, 2-OMe);13 C NMR (100 MHz, CDCl3): δC193.6 (C-9), 153.1 (C-7), 149.0 (C-4), 147.0 (C-3), 126.6 (C-1), 126.4 (C-8), 124.0 (C-6), 114.9 (C-5), 109.5 (C-2), 56.0 (2-OMe). By comparing the NMR data of compound 8 with those reported in the literature,[15] it was identified as coniferaldehyde.

Compound 9: White amorphous powder. Melting point 144–146°C.1 H NMR (400 MHz, CD3 OD): δH7.53 (1H, d, J = 15.9 Hz, H-7), 7.03 (1H, d, J = 2.0 Hz, H-2), 6.93 (1H, dd, J = 8.2, 1.9 Hz, H-6), 6.77 (1H, d, J = 8.1 Hz, H-5), 6.24 (1H, d, J = 15.8 Hz, H-8), 4.21 (2H, q, J = 7.0 Hz, H-1'), 1.30 (3H, t, J = 7.1 Hz, H-2'). NMR data comparison of compound 9 with those reported in the literature,[16] in addition to the comparison between compound 9 and standards in three different developing solvents (cyclohexane: acetone, 2:1; cyclohexane: EtOAc, 1:1; CHCl3:acetone, 4:1), confirmed that compound 9 was ethyl caffeate.

Compound 10: White amorphous powder. HR-ESI-MS (positive) m/z 432.3240 [M + Na] +, cald. for C27H44O4 Na, 432.3241.1 H NMR (400 MHz, CD3 OD): δH7.55 (1H, d, J = 15.7 Hz, H-7), 7.05 (1H, d, J = 2.0 Hz, H-2), 6.94 (1H, dd, J = 8.2, 2.0 Hz, H-6), 6.81 (1H, d, J = 8.1 Hz, H-5), 6.24 (1H, d, J = 15.8 Hz, H-8), 4.17 (2H, t, J = 6.6 Hz, H-1'), 1.71 (2H, m, H-2'), 0.88 (3H, t, J = 6.4 Hz, H-18');13 C NMR (100 MHz, CDCl3+ CD3 OD): δC168.9 (C-9), 148.4 (C-3), 146.1 (C-4), 145.7 (C-7), 127.0 (C-1), 122.3 (C-6), 115.8 (C-8), 114.8 (C-5), 114.5 (C-2), 65.1 (C-1'), 29.1 (C-2'), 26.4–30.1 (C-3' to C-15'), 32.3 (C-16'), 23.1 (C-17'), 14.2 (C-18'). By comparing the NMR and MS data of compound 10 with those reported in the literature,[17] it was identified as octadecanoyl caffeate.

Compound 11: Colorless needle (MeOH).1 H NMR (400 MHz, CDCl3): δH6.50 (1H, d, J = 8.4 Hz, H-7), 6.24 (1H, d, J = 8.4 Hz, H-6), 5.22 (1H, dd, J = 15.2, 7.4 Hz, H-23), 5.13 (1H, dd, J = 15.2, 8.1 Hz, H-22), 3.97 (1H, m, H-3), 0.99 (3H, d, J = 6.6 Hz, H-21), 0.90 (3H, t, J = 6.8 Hz, H-28), 0.88 (3H, s, H-19), 0.83 (3H, d, J = 6.6 Hz, H-27), 0.81 (3H, s, H-18), 0.81 (3H, d, J = 6.6 Hz, H-26);13 C NMR (100 MHz, CDCl3): δC135.4 (C-6), 135.2 (C-22), 132.3 (C-23), 130.7 (C-7), 82.1 (C-5), 79.4 (C-8), 66.4 (C-3), 56.1 (C-17), 51.6 (C-14), 51.0 (C-9), 44.5 (C-13), 42.7 (C-24), 39.7 (C-20), 39.3 (C-12), 36.9 (C-4), 36.9 (C-10), 34.6 (C-1), 33.0 (C-25), 30.1 (C-2), 28.6 (C-16), 23.4 (C-11), 20.8 (C-21), 20.6 (C-15), 19.9 (C-27), 19.6 (C-26), 18.1 (C-19), 17.5 (C-28), 12.8 (C-18). By comparing the NMR data of compound 11 with those reported in the literature,[18] it was identified as 5α,8α- peroxyergosterol.

Compound 12: Yellow amorphous powder.1 H NMR (600 MHz, CDCl3): δH9.66 (1H, d, J = 7.6 Hz, H-9), 7.38 (1H, d, J = 15.7 Hz, H-7), 6.81 (2H, s, H-2 and H-6), 6.61 (1H, dd, J = 7.6, 15.7 Hz, H-8), 3.94 (6H, s, 2-OMe and 6-OMe);13 C NMR (150 MHz, CDCl3): δC193.5 (C-9), 153.2 (C-7), 147.3 (C-3 and C-5), 138.0 (C-4), 126.7 (C-8), 125.5 (C-1), 105.5 (C-2 and C-6), 56.4 (2-OMe and 6-OMe). By comparing the NMR data of compound 12 with those reported in the literature,[19] it was identified as sinapaldehyde.

Compound 13: White amorphous powder.1 H NMR (400 MHz, CDCl3): δH5.59 (1H, m, H-6), 3.85 (1H, m, H-7), 3.57 (1H, m, H-3) 1.00 (3H, s, H-19), 0.92 (3H, d, J = 6.4 Hz, H-21), 0.84 (3H, t, J = 7.6 Hz, H-29), 0.83 (3H, d, J = 7.6 Hz, H-26), 0.81 (3H, d, J = 7.0 Hz, H-27), 0.68 (3H, s, H-18);13 C NMR (100 MHz, CDCl3): δC146.2 (C-5), 123.8 (C-6), 71.3 (C-3), 65.3 (C-7), 55.7 (C-17), 49.4 (C-14), 45.8 (C-24), 42.2 (C-9), 42.1 (C-13), 42.0 (C-4), 39.1 (C-12), 37.5 (C-8), 37.4 (C-10), 37.0 (C-1), 36.1 (C-20), 33.9 (C-22), 31.3 (C-2), 29.1 (C-25), 28.2 (C-16), 25.9 (C-15), 24.3 (C-23), 23.0 (C-28), 20.7 (C-11), 19.8 (C-26), 19.0 (C-27), 18.8 (C-21), 18.2 (C-19), 12.0 (C-29), 11.6 (C-18). By comparing the NMR data of compound 13 with those reported in the literature,[20] it was identified as 7 α-hydroxysitosterol.

 Discussion and Conclusion



In Tibetan medicine, Saussurea kingie, Saussurea sungpanensis, and Saussurea katochaete are used as “[INSIDE:1] ” (transliteration: “gongbagaji”) to stanch bleeding and treat furuncle.[2]S. pachyneura was also used as “[INSIDE:2] ” in some Tibetan areas.[21] This is the first report on the phytochemical research of S. pachyneura. In this study, we identified the following 13 compounds from the ethanolic extract of the whole plant material of S. pachyneura: four phenylpropanoids (compounds 8–10 and 12), three long-chain fatty acids/esters (compounds 1, 4, and 5), three steroids (compounds 3, 11, and 13), two triterpenoids (compounds 6 and 7), and one enyne (compound 2).

Financial support and sponsorship

This work was financially supported by the Fundamental Research Funds for the Central Universities (ZYGX2016J120).

Conflicts of interest

There are no conflicts of interest.

References

1Shi Z, Jin S. Delectis florae reipublicae popularis sinicae agenda academiae sinicae edita. Flora Republicae Popularis Sinicae. Vol. 18. Beijing: Science Press; 1999. p. 143-5.
2Yang Y. Northwest institute of plateau biology, Chinese Academy of Sciences. Tibetan Medicine Records. Qinghai: Qinghai People's Publishing House; 1991.
3Xie G, Tian J, Kövér KE, Mándi A, Kurtán T. Structural and stereochemical studies of a tetralin norsesquiterpenoid from Ligularia kangtingensis. Chirality 2014;26:574-9.
4Tian J, Xie GB, Xie Y, Li TN. Terpenoids from Ligularia kangtingensis. Pharmacogn Mag 2015;11:44-7.
5Xie GB, Xie Y, Hu YZ, Zhu ZX. Cytotoxic sesquiterpenoids from Ligularia pleurocaulis. Phytochemistry 2016;125:99-105.
6Xie G, Wang X, Kurtán T, Mändi A, Wang T. Sibiralactone: A new monoterpene from Sibiraea angustata. Nat Prod Commun 2011;6:1799-800.
7Hu YZ, Zhang WC, Zhang S, Xie GB. Secondary metabolites from Sibiraea angustata. Phcog Mag 2018;14:525-7.
8Dong M, Oda Y, Hirota M. (10E,12Z,15Z)-9-hydroxy-10,12,15-octadecatrienoic acid methyl ester as an anti-inflammatory compound from Ehretia dicksonii. Biosci Biotechnol Biochem 2000;64:882-6.
9Yadav JS, Deshpande PK, Sharma GV. Stereoselective synthesis of (S)-13-hydroxy octadeca-(9Z,11E)-di- and (9Z,11E,15Z)-trienoic acids: Selfdefensive substances against rice blast disease. Tetrahedron Lett 1992;48:4465-74.
10Johnson DV, Griengl H. The chemoenzymatic synthesis of (S)-13-hydroxyoctadeca-(9Z,11E)-dienoic acid using the hydroxynitrile lyase from Hevea brasiliensis. Tetrahedron 1997;53:617-24.
11Nakano H, Cantrell CL, Mamonov LK, Osbrink WL, Ross SA. Echinopsacetylenes A and B, new thiophenes from Echinops transiliensis. Org Lett 2011;13:6228-31.
12Saito Y, Iwamoto Y, Okamoto Y, Gong X, Kuroda C, Tori M. Four new guaianolides and acetylenic alcohol from Saussurea katochaete collected in China. Nat Prod Commun 2012;7:447-50.
13Gan L, Wang B, Liang H, Zhao YY, Jiang FC. Chemcial constituents from Rubus alceaefolius Poir. J Beijing Med Univ 2000;32:226-8.
14Chen HG, Li M, Gong XJ, Zhou X, Tian Y. Chemical constituents from Sammosilene tunicoides. Chin Tradit Herbal Drugs 2010;41:204-6.
15Sy LK, Brown GD. Coniferaldehyde derivatives from tissue culture of Artemisia annua and Tanacetum parthenium. Phytochemistry 1999;50:781-5.
16Lee SJ, Jang HJ, Kim Y, Oh HM, Lee S, Jung K, et al. Inhibitory effects of Il-6-induced STAT3 activation of bio-active compounds derived from Salvia plebeian R. Br. Process Biochem 2016;51:2222-9.
17García-Argáez AN, Pérez-Amador MC, Aguirre-Hernández E, Martínez-Vázquez M. Two new caffeate esters from roots of Merremia tuberosa and M. dissecta. Planta Med 1999;65:678-9.
18Hybelbauerová S, Sejbal J, Dracínský M, Hahnová A, Koutek B. Chemical constituents of Stereum subtomentosum and two other birch-associated basidiomycetes: An interspecies comparative study. Chem Biodivers 2008;5:743-50.
19Chen YQ, Su J, Shen YH, Zhang W, Hu XJ, Xu WZ, et al. Studies on chemical constituents of Daphne holosericea (Diels) Hamay a. Chin Pharm J 2008;43:1453-6.
20Liu YF, Yang XW, Wu B. Chemical constituents of the flower buds of Tussilago farfara. J Chin Pharm Sci 2007;16:288-93.
21Gong HD, Xie DF. Investigation of the traditional Tibetan medicine plant resource of the Saussurea DC. In the east of Qinghai-Tibet plateau. J Anhui Agri Sci 2009;37:171-2.