Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity

doi:10.1007/s13659-021-00321-0

Natural Products and Bioprospecting ›› 2021, Vol. 11 ›› Issue (6): 651-658.DOI: 10.1007/s13659-021-00321-0

• ORIGINAL ARTICLES • Previous Articles Next Articles

Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity

Ruo-Song Zhang^1,2, Yang-Yang Liu³, Pei-Feng Zhu^1,2, Qiong Jin^1,2, Zhi Dai³, Xiao-Dong Luo^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2 University of Chinese Academy of Sciences, Beijing 100049, China;
3 Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, China

Received:2021-09-16 Online:2021-12-10 Published:2021-12-24
Contact: Xiao-Dong Luo
Supported by:
This study was financially supported by the National Natural Science Foundation of China (Grant Nos. 31770388 and U1802281) and the Second Tibetan Plateau Scientific Expedition and Research (STEP) program (Grant No. 2019QZKK0502).

Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity

Ruo-Song Zhang^1,2, Yang-Yang Liu³, Pei-Feng Zhu^1,2, Qiong Jin^1,2, Zhi Dai³, Xiao-Dong Luo^1,3

1 State Key Laboratory of Phytochemistry and Plant Resources in West China and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
2 University of Chinese Academy of Sciences, Beijing 100049, China;
3 Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan Provincial Center for Research & Development of Natural Products, School of Chemical Science and Technology, Yunnan University, Kunming, China

通讯作者: Xiao-Dong Luo
基金资助:
This study was financially supported by the National Natural Science Foundation of China (Grant Nos. 31770388 and U1802281) and the Second Tibetan Plateau Scientific Expedition and Research (STEP) program (Grant No. 2019QZKK0502).

Abstract

Abstract: Phytochemical investigation on the roots of Asparagus cochinchinensis led to the isolation of one new furostanol saponin, named 26-O-β-D-glucopyranosyl-22α-hydroxyl-(25R)-Δ⁵⁽⁶⁾-furost-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1→ 2)-[β-Dglucopyranosyl-(1→ 4)-α-L-rhamnopyranosyl-(1→ 4)]-β-D-glucopyranoside (1), along with three known congeners (2-4). The structure of new saponin was elucidated via comprehensive inspection of its HRMS and NMR spectral data as well as chemical technology, whereas those of known ones were identified by comparison of their NMR and MS spectral data with those reported in literatures. All isolated saponins were evaluated for their cytotoxic effects on two human liver (MHCC97H) and lung adenocarcinoma (H1299) cancer cells in vitro. Among them, both 1 and 2 showed significant cytotoxicity against above mentioned cell lines. Further studies revealed that these two saponins could significantly inhibit their proliferation of MHCC97H and H1299 cells.

Key words: Steroid saponins, Asparagus cochinchinensis, Cytotoxicity, Structural elucidation

摘要： Phytochemical investigation on the roots of Asparagus cochinchinensis led to the isolation of one new furostanol saponin, named 26-O-β-D-glucopyranosyl-22α-hydroxyl-(25R)-Δ⁵⁽⁶⁾-furost-3β,26-diol-3-O-α-L-rhamnopyranosyl-(1→ 2)-[β-Dglucopyranosyl-(1→ 4)-α-L-rhamnopyranosyl-(1→ 4)]-β-D-glucopyranoside (1), along with three known congeners (2-4). The structure of new saponin was elucidated via comprehensive inspection of its HRMS and NMR spectral data as well as chemical technology, whereas those of known ones were identified by comparison of their NMR and MS spectral data with those reported in literatures. All isolated saponins were evaluated for their cytotoxic effects on two human liver (MHCC97H) and lung adenocarcinoma (H1299) cancer cells in vitro. Among them, both 1 and 2 showed significant cytotoxicity against above mentioned cell lines. Further studies revealed that these two saponins could significantly inhibit their proliferation of MHCC97H and H1299 cells.

关键词: Steroid saponins, Asparagus cochinchinensis, Cytotoxicity, Structural elucidation

Ruo-Song Zhang, Yang-Yang Liu, Pei-Feng Zhu, Qiong Jin, Zhi Dai, Xiao-Dong Luo. Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity[J]. Natural Products and Bioprospecting, 2021, 11(6): 651-658.

Ruo-Song Zhang, Yang-Yang Liu, Pei-Feng Zhu, Qiong Jin, Zhi Dai, Xiao-Dong Luo. Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity[J]. 应用天然产物, 2021, 11(6): 651-658.

References

1. S.B. Mahato, A.N. Ganguly, N.P. Sahu, Phytochemistry 21, 959– 978 (1982)
2. S.L. Man, W.Y. Gao, Y.J. Zhang, L.Q. Huang, C.X. Liu, Fitoterapia 81, 703–714 (2010)
3. J.S. Kaunda, Y.J. Zhang, Nat. Product. Bioprospect. 9, 77–137 (2019)
4. J.P. Vincken, L. Heng, A. Groot, H. Gruppen, Phytochemistry 68, 275–297 (2007)
5. M. Sautour, A.C. Mitaine-Offer, T. Miyamoto, A. Dongmo, M.A. Lacaille-Dubois, Planta Med. 70, 90–92 (2004)
6. Y. Sauvaire, G. Ribes, J.C. Baccou, M.M.L. Mariani, Lipids 26, 191–197 (1991)
7. M.J. Liu, Z. Wang, Y. Ju, J.B. Zhou, Y. Wang, R.N.S. Wong, Biol. Pharm. Bull. 27, 1059–1065 (2004)
8. T. Nikaidoa, T. Ohmotoa, S. Kubo, Y. Mimaki, Y. Sashida, Phytochemistry 31, 2445–2450 (1992)
9. I. Podolak, A. Galanty, D. Sobolewska, Phytochem. Rev. 9, 425– 474 (2010)
10. C. Bachran, S. Bachran, M. Sutherland, D. Bachran, H. Fuchs, Mini-Rev. Med. Chem. 8, 575–584 (2008)
11. R. Jian, K.W. Zeng, J. Li, N. Li, Y. Jiang, P.F. Tu, Fitoterapia 84, 80–84 (2013)
12. Y. Shen, C.L. Xu, W.D. Xuan, H.L. Li, R.H. Liu, X.K. Xu, H.S. Chen, Arch. Pharmacal Res. 34, 1587–1591 (2011)
13. H.J. Zhang, K. Sydara, G.T. Tan, C.Y. Ma, B. Southavong, D.D. Soejarto, J.M. Pezzuto, H.H.S. Fong, J. Nat. Prod. 67, 194–200 (2004)
14. X.N. Li, C. Chu, D.P. Cheng, S.Q. Tong, J.Z. Yan, Nat. Prod. Commun. 7, 1357–1358 (2012)
15. X.N. Li, C. Chu, D.P. Cheng, S.Q. Tong, J.Z. Yan, Chem. Nat. Compd. 50, 326–328 (2014)
16. B. Liu, B.X. Li, D. Zhou, X.Y. Wen, Y.J. Wang, G. Chen, N. Li, Bioorg. Chem. 4, 105237 (2021)
17. J.E. Sung, H.A. Lee, J.E. Kim, W.B. Yun, B.S. An, S.Y. Yang, D.S. Kim, C.Y. Lee, H.S. Lee, H.S. Lee, C.J. Bae, D.Y. Hwang, Int. J. Mol. Med. 40, 1365–1376 (2017)
18. J.E. Sung, J.Y. Choi, J.E. Kim, H.A. Lee, W.B. Yun, J.J. Park, H.R. Kim, B.R. Song, D.S. Kim, C.Y. Lee, H.S. Lee, Y. Lim, D.Y. Hwang, Lab. Anim. Res. 33, 57–67 (2017)
19. P.F. Zhu, G.G. Cheng, L.Q. Zhao, A. Khan, X.W. Yang, B.Y. Zhang, M.C. Li, Y.P. Liu, X.D. Luo, J. Agric. Food Chem. 69, 6229–6239 (2021)
20. S. Kiyosawa, M. Hutoh, T. Komori, T. Nohara, I. Hosokawa, T. Kawasaki, Chem. Pharm. Bull. 16, 1162–1164 (1968)
21. Y. Shao, O. Poobrasert, E. Kennelly, C.K. Chin, C.T. Ho, M.T. Huang, S.A. Garrison, G.A. Cordell, Planta Med. 63, 258–262 (1996)
22. P.K. Agrawal, Steroids 70, 715–724 (2005)
23. B. Shao, H.Z. Guo, Y.J. Cui, M. Ye, J. Han, D. Guo, Phytochemistry 68, 623–630 (2007)
24. J. Zhang, T.Y. Hu, G.L. Shen, Y. Yang, Z.B. Gu, Zhongchengyao 37, 2682–2686 (2015)
25. J.S. Negi, P. Singh, G.P. Joshi, M.S. Rawat, V.K. Bisht, Phcog. Rev. 4, 215–220 (2010)
26. B. Song, W.L. Huang, Y. Li, Y.Y. Zhang, H.W. Zhang, Y. Jiang, C. Deng, X.M. Song, J.L. Liu, Nat. Prod. Res. 35, 1478–6419 (2019)
27. X.J. Qin, L.J. Zhang, Y. Zhang, W. Ni, X.Z. Yang, Q. Yu, H. Yan, L.K. An, H.Y. Liu, Bioorg. Chem. 99, 103788 (2020)
28. Y. Zhang, H.Z. Li, Y.J. Zhang, M.R. Jacob, S.I. Khan, X.C. Li, C.R. Yang, Steroids 71, 712–719 (2006)
29. X.J. Qin, W. Ni, C.X. Chen, H.Y. Liu, Nat. Product. Bioprospect. 8, 265–278 (2018)
30. T.M. Buttkea, J.A. McCubreya, T.C. Owen, J. Immunol. Methods 157, 233–240 (1993)
31. U. Farooq, S. Khan, S. Naz, A. Khan, A. Khan, A. Ahmed, A. Rauf, S.M. Bukhari, S.A. Khan, A. Kamil, N. Riaz, A.R. Khan, China J. Nat. Med. 15, 944–949 (2017)

[1]	Pengkun Li, Qin Li, Aimin Fu, Yang Xiao, Chunmei Chen, Hucheng Zhu, Changxing Qi, Wei Wei, Yuan Zhou, Yonghui Zhang. Emestrin-type epipolythiodioxopiperazines from Aspergillus nidulans with cytotoxic activities by regulating PI3K/AKT and mitochondrial apoptotic pathways [J]. Natural Products and Bioprospecting, 2025, 15(2): 17-17.
[2]	Dong-Yang Wang, Ming-Xing Li, Yan-Chao Xu, Peng Fu, Wei-Ming Zhu, Li-Ping Wang. Dibohemamines I-O from Streptomyces sp. GZWMJZ-662, an endophytic actinomycete from the medicinal and edible plant Houttuynia cordata Thunb. [J]. Natural Products and Bioprospecting, 2025, 15(1): 9-9.
[3]	Yue-Mei Chen, Nan-Kai Cao, Si-Si Zhu, Meng Ding, Hai-Zhen Liang, Ming-Bo Zhao, Ke-Wu Zeng, Peng-Fei Tu, Yong Jiang. Euchrestifolines A-O, fifteen novel carbazole alkaloids with potent anti-ferroptotic activity from Murraya euchrestifolia [J]. Natural Products and Bioprospecting, 2025, 15(1): 5-5.
[4]	Alica Fischle, Mika Lutsch, Florian Hübner, Linda Sch?ker-Hübner, Lina Schürmann, Finn K. Hansen, Svetlana A. Kalinina. Micro-scale screening of genetically modified Fusarium fujikuroi strain extends the apicidin family [J]. Natural Products and Bioprospecting, 2024, 14(6): 51-51.
[5]	Qi-Xiu Hai, Kun Hu, Su-Ping Chen, Yang-Yang Fu, Xiao-Nian Li, Han-Dong Sun, Hong-Ping He, Pema-Tenzin Puno. Silvaticusins A-D: ent-kaurane diterpenoids and a cyclobutane-containing ent-kaurane dimer from Isodon silvaticus [J]. Natural Products and Bioprospecting, 2024, 14(5): 45-45.
[6]	Fengli Li, Saisai Gu, Sitian Zhang, Shuyuan Mo, Jieru Guo, Zhengxi Hu, Yonghui Zhang. Three new amide derivatives from the fungus Alternaria brassicicola [J]. Natural Products and Bioprospecting, 2023, 13(4): 28-28.
[7]	Shuyuan Mo, Ziming Zhao, Zi Ye, Zhihong Huang, Yaxin Zhang, Wanqi Yang, Jianping Wang, Zhengxi Hu, Yonghui Zhang. New secondary metabolites with cytotoxicity from fungus Penicillium roqueforti [J]. Natural Products and Bioprospecting, 2023, 13(3): 17-17.
[8]	Li Hou, Cui-Xuan Mei, Chun-Mao Yuan, Gui-Hua Tang, Duo-Zhi Chen, Qing Zhao, Hong-Ping He, Ming-Ming Cao, Xiao-Jiang Hao. Five new limonoids isolated from Walsura robusta [J]. Natural Products and Bioprospecting, 2023, 13(2): 7-7.
[9]	Ya-Li Hu, Xing-Ren Li, Gang Xu. Carascynol A, a hybrid of caryophyllane-type terpenoid and a C₆ unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron [J]. Natural Products and Bioprospecting, 2022, 12(6): 38-38.
[10]	Xin Zhang, Yun-Bao Ma, Xiao-Feng He, Tian-Ze Li, Chang-An Geng, Li-Hua Su, Shuang Tang, Zhen Gao, Ji-Jun Chen. Artemyrianosins A–J, cytotoxic germacrane-type sesquiterpene lactones from Artemisia myriantha [J]. Natural Products and Bioprospecting, 2022, 12(3): 16-16.
[11]	Natividad Herrera Cano, Sebastian A. Andujar, Cristina Theoduloz, Daniel A. Wunderlin, Ana N. Santiago, Guillermo Schmeda-Hirschmann, Ricardo D. Enriz, Gabriela E. Feresin. Arylated analogues of cypronazole: fungicidal effect and activity on human fibroblasts. Docking analysis and molecular dynamics simulations [J]. Natural Products and Bioprospecting, 2022, 12(2): 9-9.
[12]	Patrick O. Sakyi, Richard K. Amewu, Robert N. O. A. Devine, Emahi Ismaila, Whelton A. Miller, Samuel K. Kwofie. The Search for Putative Hits in Combating Leishmaniasis: The Contributions of Natural Products Over the Last Decade [J]. Natural Products and Bioprospecting, 2021, 11(5): 489-544.
[13]	Chen Shi, Yue-Ling Peng, Juan He, Zheng-Hui Li, Ji-Kai Liu, Tao Feng. Structures, Chemical Conversions, and Cytotoxicity of Tricholopardins C and D, Two Tricholoma Triterpenoids from the Wild Mushroom Tricholoma pardinum [J]. Natural Products and Bioprospecting, 2021, 11(2): 235-241.
[14]	Yi Chen, Song-Wei Li, Fang-Zhou Yin, Min Yang, Xia-Juan Huan, Ze-Hong Miao, Xiao-Ming Wang, Yue-Wei Guo. Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus [J]. Natural Products and Bioprospecting, 2021, 11(1): 73-79.
[15]	Mohammad Sanad Abu-Darwish, Célia Cabral, Zulfigar Ali, Mei Wang, Shabana I. Khan, Melissa R. Jacob, Surendra K. Jain, Babu L. Tekwani, Fazila Zulfiqar, Ikhlas A. Khan, Hatem Taifour, Lígia Salgueiro, Thomas Efferth. Salvia ceratophylla L. from South of Jordan: new insights on chemical composition and biological activities [J]. Natural Products and Bioprospecting, 2020, 10(5): 307-316.

Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity

Furostanol Saponins from Asparagus cochinchinensis and Their Cytotoxicity

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments