| ORIGINAL ARTICLES |
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Carascynol A, a hybrid of caryophyllane-type terpenoid and a C6 unit degraded by polyprenylated acylphloroglucinols from Hypericum ascyron |
| Ya-Li Hu1,2, Xing-Ren Li1, Gang Xu1 |
1 State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, and Yunnan Key Laboratory of Natural Medicinal Chemistry, Kunming 650201, Yunnan, People's Republic of China;
2 University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China |
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Abstract Carascynol A, an unprecedented 4/9/8 ring system hybrid with a peroxide bridge, was characterized from Hypericum ascyron. The architecture contains a caryophyllane-type moiety and a C6 unit derived from polyprenylated acylphloroglucinols. Its structure and absolute configuration were determined by comprehensive spectroscopic and X-ray difraction data. Biologically, compound 1 inhibited cell proliferation in LoVo, SW480, and HCT116 cell lines (IC50= 12.30-24.57 μM).
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| Keywords
Hypericum ascyron, Caryophyllane, Polyprenylated acylphloroglucinols, Cytotoxicity, Colon cancer
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| Fund:This work was fnancially supported by the NSFC-Joint Foundation of Yunnan Province (Grant No. U1902213) the Second Tibetan Plateau Scientifc Expedition and Research (STEP) program (Grant No. 2019QZKK0502-0303), Natural Science Foundation of Yunnan (Grant No. 2019FA003), CAS Interdisciplinary Innovation Team of CAS “Light of West China” Program, and the Fund of State Key Laboratory of Phytochemistry and Plant Resources in West China (Grant No. E0230211Z1). |
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Corresponding Authors:
Gang Xu, E-mail: xugang008@mail.kib.ac.cn
E-mail: xugang008@mail.kib.ac.cn
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Issue Date: 23 December 2022
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1. Sung H, Ferlay J, Siegel RL, Laversanne M, Soerjomataram I, Jemal A, Bray F. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries. CA A Cancer J Clin. 2021;71:209-49.
2. Engstrand J, Nilsson H, Stromberg C, Jonas E, Freedman J. Colorectal cancer liver metastases—a population-based study on incidence, management and survival. BMC Cancer. 2018;18:78.
3. Xie YH, Chen YX, Fang JY. Comprehensive review of targeted therapy for colorectal cancer. Signal Transduct Target Therapy. 2020;5:22.
4. Atanasov AG, Zotchev SB, Dirsch VM, the International Natural Product Sciences Taskforce, Supuran CT. Natural products in drug discovery: advances and opportunities. Nat Rev Drug Discov. 2021;20:200-16.
5. Chang SU. Dictionary of Chinese crude drugs. Shanghai: New Medical College Shanghai Scientifc Technological Publishers; 1997. p. 1002.
6. Kong LM, Long XW, Yang XW, Xia F, Khan A, Yan H, Deng J, Li X, Xu G. seco-Polycyclic polyprenylated acylphloroglucinols with unusual carbon skeletons from Hypericum ascyron. Tetrahedron Lett. 2017;58:2113-7.
7. Hu YL, Hu K, Kong LM, Xia F, Yang XW, Xu G. Norascyronones A and B, 2,3,4-nor-polycyclic polyprenylated acylphloroglucinols from Hypericum ascyron. Org Lett. 2019;21:1007-10.
8. Ciochina R, Grossman RB. Polycyclic polyprenylated acylphloroglucinols Chem. Rev. 2006;106:3963-86.
9. Yang XW, Grossman RB, Xu G. Research progress of polycyclic polyprenylated acylphloroglucinols. Chem Rev. 2018;118:3508-58.
10. Liao Y, Yang SY, Li XN, Yang XW, Xu G. Polyprenylated acylphloroglucinols from the fruits of Hypericum henryi. Sci China Chem. 2016;59:1216-23.
11. Yang XW, Yang J, Xu G. Skeleton reassignment of type C polycyclic polyprenylated acylphloroglucinols. J Nat Prod. 2017;79:108-13.
12. Zhang JJ, Yang XW, Liu X, Ma JZ, Liao Y, Xu G. 1,9-seco-Bicyclic polyprenylated acylphloroglucinols from Hypericum uralum. J Nat Prod. 2015;78:3075-9.
13. Zhang JJ, Yang XW, Ma JZ, Ye Y, Shen XL, Xu G. Cytotoxic polyprenylated acylphloroglucinol derivatives from Hypericum henryi. Tetrahedron. 2015;71:8315-9.
14. Pouységu L, Marguerit M, Gagnepain J, Lyvinec G, Eatherton AJ, Quideau S. Total synthesis of wasabidienones B1 and B0 via SIBX-mediated hydroxylative phenol dearomatization. Org Lett. 2008;10:5211-4.
15. Huang YR, Tippmann J, Becker T. Kinetic modeling of hop acids during wort boiling. Int J Biosci Biochem Bioinform. 2013;3:47-52.
16. Rakete S, Berger R, Böhme S, Glomb MA. Oxidation of isohumulones induces the formation of carboxylic acids by hydrolytic cleavage. J Agric Food Chem. 2014;62:7541-9.
17. Yang XW, Li YP, Su J, Ma WG, Xu G. Hyperjapones A-E, terpenoid polymethylated acylphloroglucinols from Hypericum japonicum. Org Lett. 2016;18:1876-9. |
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