New tirucallane triterpenoids from Picrasma quassioides with their potential antiproliferative activities on hepatoma cells |
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| Institution: | 1. State Key Laboratory of Natural Medicines, Department of Natural Medicinal Chemistry, China Pharmaceutical University, 24 Tong Jia Xiang, Nanjing 210009, People''s Republic of China;2. Testing & Analysis Center, Nanjing Normal University, Nanjing 210023, People''s Republic of China;1. State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zu Chong Zhi Road 555, Shanghai 201203, China;2. Dipartimento di Farmacia, Università di Napoli ‘Federico II’, Via D. Montesano, 49, 80131 Napoli, Italy;3. Syngenta Jealotts Hill International Research Centre, Berkshire RG42 6EY, United Kingdom;4. State Key Laboratory of Natural Medicines, China Pharmaceutical University, Nanjing 210009, China;1. College of Biological Resources and Environment Science, Qujing Normal University, Qujing 655011, Yunnan, China;2. Department of Pharmacy, 455 Hospital of People''s Liberation Army, Shanghai 200052, China;3. College of Physics and Electronic Engineering, Qujing Normal University, Qujing 655011, China |
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| Abstract: | Seven new tirucallane-type triterpenoids (1–7), kumuquassin A-G, along with 20 known analogues (8–27) were isolated from the stems of Picrasma quassioides. The structures and the absolute configurations of new compounds were elucidated by spectroscopic data, electronic circular dichroism (ECD) spectroscopic analyses and quantum ECD calculations. Notably, kumuquassin A (1) contains a rare Δ17, 20 double bond, kumuquassin B (2) is the first example of tirucallane triterpenoid possessing a 5/3 biheterocyclic ring system at the side chain. All the compounds were screened for the cytotoxicity against two human hepatoma cell lines, HepG2 and Hep3B, and several compounds exhibited promising activity. The most potential compound 3 was selected for cell cycle analysis, which showed that 3 could cause an accumulation of HepG2 cells at subG1 peak. Annexin V-FITC/PI staining further confirmed that compound 3 caused death of hepatoma cells through apoptosis induction. |
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| Keywords: | Tirucallane triterpenoids Cytotoxicity Anti-hepatoma |
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