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New Thymol Derivatives and Cytotoxic Constituents from the Root of Eupatorium cannabinum ssp. asiaticum
Author(s) -
Chen LiChai,
Lee TzongHuei,
Sung PingJyun,
Shu ChihWen,
Lim YunPing,
Cheng MingJen,
Kuo WenLung,
Chen JihJung
Publication year - 2014
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201300392
Subject(s) - thymol , chemistry , eupatorium , stereochemistry , phenol , cytotoxic t cell , cancer cell lines , cytotoxicity , botany , organic chemistry , food science , biochemistry , essential oil , in vitro , biology , genetics , cancer , cancer cell
Abstract Two new thymol (=5‐methyl‐2‐(1‐methylethyl)phenol) derivatives, 8,10‐didehydro‐9‐(3‐methylbutanoyl)thymol 3‐ O ‐tiglate ( 1 ) and 9‐ O ‐angeloyl‐8‐methoxythymol 3‐ O ‐isobutyrate ( 2 ), were isolated from the root of Eupatorium cannabinum ssp. asiaticum , together with six known compounds, 3 – 8 . The structures of 1 and 2 were determined through extensive 1D/2D‐NMR and MS analyses. Among the isolates, 9‐acetoxy‐8,10‐epoxythymol 3‐ O ‐tiglate ( 3 ) was the most cytotoxic, with IC 50 values of 0.02±0.01, 1.02±0.07, and 1.36±0.12 μg/ml, respectively, against DLD‐1, CCRF‐CEM, and HL‐60 cell lines. In addition, 10‐acetoxy‐9‐ O ‐angeloyl‐8‐hydroxythymol ( 4 ) and eupatobenzofuran ( 6 ) exhibited cytotoxicities, with IC 50 values of 1.14±0.16 and 2.63±0.22, and 7.63±0.94 and 2.31±0.14 μg/ml, respectively, against DLD‐1 and CCRF‐CEM cell lines.