title: Leonurusoleanolides E-J, minor spirocyclic triterpenoids from Leonurus japonicus fruits.
abstract: Six new (leonurusoleanolides E-J, 1-6) and five known (7-11) nortriterpenoids were isolated and characterized from the dried fruits of Leonurus japonicus. They all contain a distinctive 19(18→17)-abeo-28-noroleanane-type spirocylclic skeleton with a trans or a cis acyl substituent at C-3 or C-23. Similar to the previously known leonurusoleanolides A/B (7/8) and C/D (9/10), compounds 1/2 and 3/4 were also found to exist as equilibrium mixtures of trans and cis isomers. The isolated pure compounds and mixtures were evaluated for their cytotoxicity against a small panel of human cancer cell lines (BGC-823 and KE-97 gastric carcinoma, Huh-7 hepatocarcinoma, Jurkat T cell lymphoblasts, and MCF-7 breast adenocarcinoma) using the CellTiter-Glo luminescent cell viability assay method. Among them, (2α,3β,17R*,18β)-3-O-(trans-caffeoyl)-19(18→17)-abeo-28-norolean-12-ene-2,18,23-triol (leonurusoleanolide J, 6) showed the most potent cytotoxic activity, with IC50 values less than 10 μM.
authors: Department of Natural Products Chemistry, School of Pharmacy, Fudan University , Shanghai 201203, People's Republic of China.
authors: Miao
authors: M
authors: Ye
authors: Juan
authors: J
authors: Xiong
authors: Jing-Jing
authors: JJ
authors: Zhu
authors: Jun-Lin
authors: JL
authors: Hong
authors: Yun
authors: Y
authors: Zhao
authors: Hui
authors: H
authors: Fan
authors: Guo-Xun
authors: GX
authors: Yang
authors: Gang
authors: G
authors: Xia
authors: Jin-Feng
authors: JF
authors: Hu
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006528:Carcinoma, Hepatocellular; D002470:Cell Survival / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005638:Fruit / Q000737:chemistry; D006801:Humans; D020128:Inhibitory Concentration 50; D031332:Leonurus / Q000737:chemistry*; D008113:Liver Neoplasms; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D013141:Spiro Compounds; D014315:Triterpenes