Structurally Diverse Limonoids from Trichilia connaroides and Their Antitumor Activities
Ying Yan
State Key Laboratory of Functions and Applications of Medicinal Plants & College of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang, Guizhou, 550014 China
School of Medicine and Health Management, Guizhou Medical University, Guiyang, Guizhou, 550025 China
These authors contributed equally.
Search for more papers by this authorDan Wang
State Key Laboratory of Functions and Applications of Medicinal Plants & College of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang, Guizhou, 550014 China
These authors contributed equally.
Search for more papers by this authorFang-Jiao Zhou
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
These authors contributed equally.
Search for more papers by this authorYu-Han Zhao
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorXu-Jie Qin
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorYu Zhang
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorXiao Ding
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorCorresponding Author
Xiao-Jiang Hao
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
E-mail: [email protected]Search for more papers by this authorYing Yan
State Key Laboratory of Functions and Applications of Medicinal Plants & College of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang, Guizhou, 550014 China
School of Medicine and Health Management, Guizhou Medical University, Guiyang, Guizhou, 550025 China
These authors contributed equally.
Search for more papers by this authorDan Wang
State Key Laboratory of Functions and Applications of Medicinal Plants & College of Pharmacy, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D, Guizhou Medical University, Guiyang, Guizhou, 550014 China
These authors contributed equally.
Search for more papers by this authorFang-Jiao Zhou
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
These authors contributed equally.
Search for more papers by this authorYu-Han Zhao
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorXu-Jie Qin
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorYu Zhang
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorXiao Ding
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
Search for more papers by this authorCorresponding Author
Xiao-Jiang Hao
Key Laboratory of Phytochemistry and Natural Medicines, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, Yunnan, 650201 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
Twelve new limonoids (1—12), named trichilitins A—L, were isolated from the leaves and twigs of Trichilia connaroides, together with ten known compounds (13—22). The structures were elucidated by extensive spectroscopic investigations, X-ray diffraction analyses, and ECD calculations. Compound 1, which belongs to a unique class of ring B-seco limonoid, has been identified as 6/7/6/5 tetracyclic due to a key Baeyer-Villiger oxidation. Compounds 2—7 were identified as ring intact limonoids, while compounds 8—10 were established as ring D-seco ones, and 11 and 12 were determined to be rearranged ones. All of the compounds were tested for cytotoxicity against three human tumor cell lines (HCT-116, NCl-H1975, and SH-SY5Y). Compounds 6, 7, 13, 14, and 19 exhibited significant cytotoxic effects, especially 7 exhibited significant cytotoxic effects against HCT-116 with an IC50 value of 0.035 μmol·L–1 and was more active than the positive control, doxorubicin with an IC50 value of 0.20 μmol·L–1. Compound 7 effectively induced apoptosis of HCT-116, which was associated with S-phase cell cycle arrest. Furthermore, the Western blot analysis showed that compound 7 could induce cell cycle arrest by promoting the expression levels of p53 and p21.
Supporting Information
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