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Guaiane Sesquiterpenoids Isolated from the Fruits of Torilis japonica and Their Cytotoxic Activity
Author(s) -
Kim Dong Chun,
Kim Jeong Ah,
Min Byung Sun,
Jang TaeSu,
Na MinKyun,
Lee Seung Ho
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900278
Subject(s) - chemistry , friedelin , phytochemical , cytotoxic t cell , cytotoxicity , stereochemistry , daucosterol , traditional medicine , biochemistry , chemical constituents , chromatography , in vitro , triterpenoid , medicine
Two new guaiane sesquiterpenoids, 11‐(acetyloxy)‐1,8‐dihydroxyguai‐4‐en‐3‐one ( 5 ) and (1 α ,6 β )‐1,6‐dihydroxytorilin ( 6 ), were isolated from the fruits of Torilis japonica (Umbelliferae), along with four known sesquiterpenes, torilin ( 1 ), torilolone ( 2 ), (1 β )‐1‐hydroxytorilin ( 3 ), and (1 α )‐1‐hydroxytorilin ( 4 ). During the phytochemical investigation, daucosterol, friedelin, and epifriedelanol were also isolated from the plant for the first time. The structures of the new sesquiterpenoids 5 and 6 were determined by comprehensive analyses of MS and NMR spectroscopic data. These isolates were evaluated against human breast cancer cells (MCF‐7) and Lewis lung carcinoma (LLC) cells. Compounds 1, 3 , and 4 exhibited cytotoxic activity against the LLC cells with IC 50 values of 31.3, 32.5, and 34.0 μg/ml, respectively. However, no significant cytotoxicity was found against the MCF‐7 cells for any of the compounds tested.