Triterpenoids from the fruits of Azadirachta indica (Meliaceae) |
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| Affiliation: | 1. Graduate School of Pharmaceutical Sciences, University of Tokushima, Shomachi 1-78, Tokushima 770-8505, Japan;2. Department of Botany, Faculty of Biological Sciences, Jahangirnagar University, Savar, Dhaka 1342, Bangladesh;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. Department of Pharmacy, Wuhan First Hospital, Wuhan 430022, Hubei, China;2. Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China;3. Tongji Hospital Affiliated to Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, China;4. Department of Pharmacy, Zhejiang University of Traditional Chinese Medicine, Zhejiang 310053, China;1. School of Traditional Chinese Medicine, Shenyang Pharmaceutical University, Shenyang 110016, China;2. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China;3. Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China;4. State Key Laboratory for Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, China |
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| Abstract: | Four new triterpenoids, indicalilacols A-D (1–4), were isolated from the MeOH extract of the fruits of Azadirachta indica, including a new 19(10 → 9β)abeo-tirucallane derivative, two new tirucallane-type triterpenoids, and a new euphane-type triterpenoid, along with three known tirucallane-type triterpenoids. Their structures were elucidated on the basis of spectroscopic analyses. The absolute configuration of 2 was elucidated by the chemical conversion of 2 into 21-oxo-melianodiol 24,25-acetonide. Compounds 2, 6–8 exhibited moderate cytotoxicity against three human cancer cell lines, including multidrug-resistant (MDR) cancer cells (KB-C2). Although compound 5 was not cytotoxic against any of the tested cancer cell lines, 5 showed cytotoxicity against KB-C2 cells in the presence of 2.5 μM colchicine, suggesting that 5 might have an MDR-reversal effect. |
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