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Asprecosides A-J, ten new pentacyclic triterpenoid glycosides with cytotoxic activity from the roots of Ilex asprella |
| Yuwei Wu1,2, Baihui Zhang1,2, Wenxian Li2, Lihua Peng3, Weilin Qiao3, Wei Li1,2, De-an Guo1,2 |
1. School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, People's Republic of China;
2. Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan, 528400, People's Republic of China;
3. Zhongshan Zhongzhi Pharmaceutical Group Co. Ltd., Zhongshan, 528400, People's Republic of China |
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Abstract Phytochemical study of the n-BuOH extract of Ilex asprella resulted in the discovery of ten new pentacyclic triterpenoid glycosides, comprising nine ursane-type glycosides (1-9) and one oleanane-type glycoside (10), along with seven known compounds (11-17). Compound 1 is the first reported 19,22-epoxy ursane triterpenoid glycoside, whereas 4 and 5 are rare examples of ursane triterpenoid glycosides containing a 28,19-lactone group. The structural characterization of these compounds was achieved using spectroscopic and chemical techniques, as well as single-crystal X-ray analysis. Compounds 7, 12, 15, and 17 exhibited moderate cytotoxic activities against H1975 and HCC827 cancer cells.
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| Keywords
Ilex asprella
Pentacyclic triterpenoid glycoside
Ursane
Oleanane
Cytotoxic activity
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| Fund:This work was supported by the Qi-Huang Chief Scientist Project of the National Administration of Traditional Chinese Medicine (2020). |
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Corresponding Authors:
Wei Li, E-mail:liwei1@simm.ac.cn;De-an Guo, E-mail:daguo@simm.ac.cn
E-mail: liwei1@simm.ac.cn;liwei1@simm.ac.cn;daguo@simm.ac.cn
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Issue Date: 17 May 2025
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[1] Lacaille-Dubois MA, Wagner H. New perspectives for natural triterpene glycosides as potential adjuvants. Phytomedicine. 2017;37:49-57.
[2] Vincken JP, Heng L, De Groot A, Gruppen H. Saponins, classification and occurrence in the plant kingdom. Phytochemistry. 2007;68:275-97.
[3] Li Y, Wang J, Li L, Song W, Li M, Hua X, Wang Y, Yuan J, Xue Z. Natural products of pentacyclic triterpenoids: from discovery to heterologous biosynthesis. Nat Prod Rep. 2023;40:1303-53.
[4] Dzubak P, Hajduch M, Vydra D, Hustova A, Kvasnica M, Biedermann D, Markova L, Urban M, Sarek J. Pharmacological activities of natural triterpenoids and their therapeutic implications. Nat Prod Rep. 2006;23:394-411.
[5] Lv N, Wang L, Zeng M, Wang Y, Yu B, Zeng W, Jiang X, Suo Y. Saponins as therapeutic candidates for atherosclerosis. Phytother Res. 2024;38:1651-80.
[6] Pham HTT, Ryu B, Cho HM, Lee BW, Yang WY, Park EJ, Tran VO, Oh WK. Oleanane hemiacetal glycosides from Gymnema latifolium and their inhibitory effects on protein tyrosine phosphatase 1B. Phytochemistry. 2020;170: 112181.
[7] Liu XG, Sun YQ, Bian J, Han T, Yue DD, Li DQ, Gao PY. Neuroprotective effects of triterpenoid saponins from Medicago sativa L. against H2O2-induced oxidative stress in SH-SY5Y cells. Bioorg Chem. 2019;83:468-76.
[8] Nguyen MK, Nguyen VP, Yang SY, Min BS, Kim JA. Astraoleanosides E-P, oleanane-type triterpenoid saponins from the aerial parts of Astragalus membranaceus Bunge and their β-glucuronidase inhibitory activity. Bioorg Chem. 2024;145: 107230.
[9] Yang XW, Dai Z, Wang B, Liu YP, Zhao XD, Luo XD. Antitumor triterpenoid saponin from the fruits of Avicennia marina. Nat Prod Bioprospect. 2018;8:347-53.
[10] Yang X, Gao X, Du B, Zhao F, Feng X, Zhang H, Zhu Z, Xing J, Han Z, Tu P, Chai X. Ilex asprella aqueous extracts exert in vivo anti-inflammatory effects by regulating the NF-κB, JAK2/STAT3, and MAPK signaling pathways. J Ethnopharmacol. 2018;225:234-43.
[11] Bai C, Zhou X, Han L, Yu Y, Li N, Zhang M, Qu Z, Tu P. Two new 18, 19-seco triterpenoids from Ilex asprella (Hook. et Arn.) Champ. ex Benth. Fitoterapia. 2018;127:42-6.
[12] Wen Q, Lu Y, Chao Z, Chen DF. Anticomplement triterpenoids from the roots of Ilex asprella. Bioorg Med Chem Lett. 2017;27:880-6.
[13] Wang L, Cai Y, Zhang XQ, Fan CL, Zhang QW, Lai XP, Ye WC. New triterpenoid glycosides from the roots of Ilex asprella. Carbohydr Res. 2012;349:39-43.
[14] Lei Y, Shi SP, Song YL, Bi D, Tu PF. Triterpene saponins from the roots of Ilex asprella. Chem Biodivers. 2014;11:767-75.
[15] Huang XJ, Wen S, Guan XF, Wu ZL, Li MM, Fan CL, Zhang QW, Chan G, Wang Y, Ye WC. Eleven new triterpenoid glycosides from the roots of Ilex asprella. Chem Biodivers. 2019;16: e1900202.
[16] Kashiwada Y, Zhang DC, Chen YP, Cheng CM, Chen HT, Chang HC, Chang JJ, Lee KH. Anti-tumor agents, 145. Cytotoxic asprellic acids A and C and asprellic acid B, new p-coumaroyl triterpenes, from Ilex asprella. J Nat Prod. 1993;56:2077-82.
[17] Zhou M, Xu M, Ma XX, Zheng K, Yang K, Yang CR, Wang YF, Zhang YJ. Antiviral triterpenoid saponins from the roots of Ilex asprella. Planta Med. 2012;78:1702-5.
[18] Li W, Gan L, Yuan FY, Sang J, Huang D, Yin AP, Pu R, Tang GH, Guo D, Yin S. Biscroyunoid A, an anti-hepatic fibrotic 19-nor-clerodane diterpenoid dimer with a C-16-C-12' linkage from Croton yunnanensis. J Nat Prod. 2023;86:434-9.
[19] Wang D, Mei F, Nie J, Li Z, Zhang D, Guo D, Li W. Highly oxygenated clerodane furanoditerpenoids from the leaves and twigs of Croton yunnanensis. Chin J Nat Med. 2024;22:945-54.
[20] Li S, Zhao J, Wang W, Lu Y, Xu Q, Liu Y, Li X, Khan IA, Yang S. Seven new triterpenoids from the aerial parts of Ilex cornuta and protective effects against H2O2-induced myocardial cell injury. Phytochem Lett. 2015;14:178-84.
[21] Liao L, Zhou X, Liu YL, Xu QM, Li XR, Yang SL. Four new triterpenoidal saponins from Ilex cornuta and their cytotoxic activities. Phytochem Lett. 2013;6:429-34.
[22] Yan XL, Sang J, Zhang X, Lin Y, Long QD, Zhu QF, Liao SG. Euphorboside A, a cytotoxic meroterpenoid glycoside with an unusual humulene-phloroglucinol skeleton from Euphorbia kansuensis. Fitoterapia. 2021;153: 104966.
[23] Inada A, Kobayashi M, Murata H, Nakanishi T. Two new triterpenoid glycosides from leaves of Ilex chinensis Sims. Chem Pharm Bull. 1987;35:841-5.
[24] Cai Y, Zhang Q, Li Z, Fan C, Wang L, Zhang X, Ye W. Chemical constituents from roots of Ilex asprella. Chin Tradit Herb Drugs. 2010;41:1426-9.
[25] Li SS, Liu YL, Xu QM, Mao CM, Yang SL. Three new triterpenoids isolated from the aerial parts of Ilex cornuta and protective effects against H2O2-induced myocardial cell injury. Chin J Nat Med. 2017;15:115-20. |
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