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Five new limonoids isolated from Walsura robusta |
Li Hou1,2,4, Cui-Xuan Mei1,3, Chun-Mao Yuan1,5, Gui-Hua Tang1, Duo-Zhi Chen1, Qing Zhao2, Hong-Ping He1,2, Ming-Ming Cao1, Xiao-Jiang Hao1,5,6,7 |
1. State Key Laboratory of Photochemistry 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. School of Ethnic Medicine, and School of Chinese Materia Medical, Yunnan University of Chinese Medicine, Kunming, 650500, China; 3. University of Chinese Academy of Sciences, Beijing, 100049, China; 4. Bureau of Commerce and Market Supervision of Management Committee of Hunan Xiangjiang New Area, Changsha, 410205, China; 5. The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang, 550014, China; 6. Research Unit of Chemical Biology of Natural Anti-Virus Products, Chinese Academy of Medical Sciences, Beijing, 100730, China; 7. Yunnan Characteristic Plant Extraction Laboratory, Kunming, 650106, China |
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Abstract Five new toosendanin limonoids with highly oxidative furan ring walsurobustones A-D (1-4), and one new furan ring degraded limonoid walsurobustone E (5) together with one known compound toonapubesic acid B (6) were isolated from the leaves of Walsura robusta. Their structures were elucidated by NMR and MS data. Especially, the absolute configuration of toonapubesic acid B (6) was confirmed by X-ray diffraction study. Compounds 1-6 exhibited good cytotoxicity against the cancer cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480.
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Keywords
Limonoids
Tetranortriterpenoids
Walsura robusta
Cytotoxicity
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Fund:This research was supported financially by grants from the National Natural Science Foundation of China (U1812403 to X.-J. Hao and 22177050 to M. Cao), Project of Yunnan Characteristic Plant Screening and R&D Service CXO Platform (2022YKZY001), Foundation of Central Asian Drug Discovery and Development Center of Chinese Academy of Sciences (CAM202103, China), and Youth Innovation Promotion Association CAS to M. Cao (2022-2026). |
Corresponding Authors:
Hong-Ping He,E-mail:hehongping@yahoo.com;Ming-Ming Cao,E-mail:caomingming@mail.kib.ac.cn;Xiao-Jiang Hao,E-mail:haoxj@mail.kib.ac.cn
E-mail: hehongping@yahoo.com;caomingming@mail.kib.ac.cn;haoxj@mail.kib.ac.cn
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Issue Date: 18 May 2023
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1 Luo J, Sun YP, Li QR, Kong LY. Research progress of meliaceous limonoids from 2011 to 2021. Nat Prod Rep. 2022;39:1325-65. 2 Tan QG, Luo XD. Meliaceous limonoids:chemistry and biological activities. Chem Rev. 2011;111:7437-522. 3 Peng H, Mabberley DJ. Flora of China. 2008;11:119-20. 4 Luo XD, Wu SH, Ma YB, Wu DG. Tetranortriterpenoids from Walsura yunnanensis. J Nat Prod. 2000;63:947-51. 5 Balakrishna K, Rao RB, Patra A, Ali SU. Constituents of Walsura piscidia. Fitoterapia. 1995;66:548. 6 Chatterjee A, Kundu AB, Chakrabortty T, Chandrasekharan S. Structure of walsurenol, a new pentacyclic triterpene alcohol from Walsura tubulata. Chem Commun 1968;418-9. 7 Govindachari TR, Kumari GNK, Suresh G. Triterpenoids from Walsura piscidia. Phytochemistry. 1995;39:167-70. 8 Lakshmi S, Subramanian K, Steiner T, Varghese B. Piscidinol-C, a triterpenoid from Walsura piscidia leaves. J Chem Crystallogr. 1999;29:1141-3. 9 Purushothaman KK, Duraiswamy K, Connolly J, Rycroft DS. Triterpenoids from Walsura piscidia. Phytochemistry. 1985;24:2349-54. 10 Yin S, Wang XN, Fan CQ, Liao SG, Yue JM. The first limonoid peroxide in the meliaceae family:Walsuronoid A from Walsura robusta. Org Lett. 2007;9:2353-6. 11 Zhou ZW, Yin S, Zhang HY, Fu Y, Yang SP, Wang XN, Wu Y, Tang XC, Yue JM. Walsucochins A and B with an unprecedented skeleton isolated from Walsura cochinchinensis. Org Lett. 2008;10:465-8. 12 Balakrishna K, Sukumar E, Connolly JD. Piscidenone and Piscidinol G, Two new protolimonoids from Walsura piscidia. Nat Prod Sci. 2003;9:192-4. 13 Luo XD, Wu SH, Ma YB, Wu DG. Chemical constituents from Walsura yunnanensis. Acta Bot Yunnanica. 2001;23:515-20. 14 Yang W, Kong LM, Li SF, Li Y, Zhang Y, He HP, Hao XJ. Five new mexicanolide type limonoids from Heynea trijuga. Nat Prod Bioprospect. 2012;2:145-9. 15 Cao MM, Zhang Y, Li XH, Peng ZG, Jiang JD, Gu YC, Di YT, Li XN, Chen DZ, Xia CF, He HP, Li SL, Hao XJ. Cyclohexane-fused octahydroquinolizine alkaloids from Myrioneuron faberi with activity against hepatitis C virus. J Org Chem. 2014;79:7945-50. 16 Wang GC, Yu JH, Shen Y, Leng Y, Zhang H, Yue JM. Limonoids and triterpenoids as 11beta-HSD1 inhibitors from Walsura robusta. J Nat Prod. 2016;79:899-906. 17 Mohankumar R, Ilango K, Pridiuldi V, Santhanakrishnan, Radhakrishnan V, Narasimhan S. Ethylenediamine:an effective reagent for deacetylation of natural products. J Asian Nat Prod Res. 2010;12:851-8. 18 Wang JR, Liu HL, Kurtán T, Mándi A, Antus S, Li J, Zhang HY, Guo YW. Protolimonoids and norlimonoids from the stem bark of Toona ciliata var. pubescens. Org Biomol Chem. 2011;9:7685-96. |
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