title: Bioactive Pentacyclic Triterpenoids from the Leaves of Cleistocalyx operculatus.
abstract: Thirteen new pentacyclic triterpenoids, cleistocalyxic acids A-K (1, 2, 4, 5, and 7-13) and cleistocalyxolides A (3) and B (6), and 15 known analogues (14-28), based on taraxastane, oleanane, ursane, multiflorane, and lupane skeletons, were isolated from the leaves of Cleistocalyx operculatus. The structures of 1-13 were elucidated by analysis of their spectroscopic data and ECD/TDDFT computations. Cleistocalyxolide A (3), presumed to be derived from the known taraxastane-type compound 14, has a rare rearranged triterpenoid backbone. Cleistocalyxic acid B (2) displayed cytotoxicity against HepG2, NCI-N87, and MCF-7 cancer cell lines with IC50values ranging from 3.2 to 6.5 μM, and cleistocalyxic acid D (5) was active against HepG2 and NCI-N87 cells with values around 5.0 μM. The noncytotoxic cleistocalyxic acid E (7) inhibited production of IL-6 by 68.1% and TNF-α by 53.7% in LPS-induced RAW 264.7 macrophages at a concentration of 2 μM.
authors: Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.|University of Chinese Academy of Sciences , Yuquanlu 19A, Beijing 100049, People's Republic of China.
authors: Chen
authors: C
authors: Wang
authors: Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
authors: Ping
authors: P
authors: Wu
authors: Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
authors: Shuai
authors: S
authors: Tian
authors: Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
authors: Jinghua
authors: J
authors: Xue
authors: Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
authors: Liangxiong
authors: L
authors: Xu
authors: Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
authors: Hanxiang
authors: H
authors: Li
authors: Key Laboratory of Plant Resources Conservation and Sustainable Utilization and Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences , Xingke Road 723, Tianhe District, Guangzhou 510650, People's Republic of China.
authors: Xiaoyi
authors: X
authors: Wei
mesh_terms: D000818:Animals; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D056945:Hep G2 Cells; D006801:Humans; D015850:Interleukin-6 / Q000378:metabolism; D061986:MCF-7 Cells; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D027822:Myrtaceae / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D009828:Oleanolic Acid / Q000031:analogs & derivatives; D053978:Pentacyclic Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha / Q000187:drug effects
chemical_list: D004365:Drugs, Chinese Herbal; D015850:Interleukin-6; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; D014409:Tumor Necrosis Factor-alpha; C413246:oleanane; C480546:lupane; D009828:Oleanolic Acid