New thymol derivatives and cytotoxic constituents from the root of eupatorium cannabinum ssp. asiaticum
Journal
Chemistry and Biodiversity
Journal Volume
11
Journal Issue
9
Pages
1374 - 1380
Date Issued
2014
Author(s)
Chen, Li-Chai
Sung, Ping-Jyun
Shu, Chih-Wen
Lim, Yun-Ping
Cheng, Ming-Jen
Kuo, Wen-Lung
Chen, Jih-Jung
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 IC50 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 IC50 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. Copyright ? 2014 Verlag Helvetica Chimica Acta AG, Z?rich.
Subjects
Cytotoxic activity; Eupatorium cannabinum; Thymol derivatives
SDGs
Other Subjects
10 acetoxy 9 o angeloyl 8 hydroxythymol; 2h chromen 2 one; 8,10 didehydro 9 (3 methyl butanoyl)thymol 3 o tiglate; 9 acetoxy 8,10 epoxythymol 3 o tiglate; 9 o angeloyl 8 methoxythymol; 9 o angeloyl 8 methoxythymol 3 o isobutyrate; doxorubicin; euparin; eupatobenzofuran; pharmacology; plant extract; thymol; thymol; unclassified drug; Article; carbon nuclear magnetic resonance; cell line; chemical structure; chemistry; China; colorectal cancer cell line; controlled study; drug cytotoxicity; drug isolation; drug screening; electrospray mass spectrometry; Eupatorium; Eupatorium; Eupatorium cannabium ssp. asiaticum; herb; HL 60 cell line; human; human; human cell; IC50; isolation and purification; leukemia cell line; lymphoma cell line; medicinal plant; nonhuman; nuclear magnetic resonance spectroscopy; plant root; plant root; proton nuclear magnetic resonance; Taiwan; traditional medicine; Cell Line; chemistry; chemistry; chemistry; Drug Screening Assays, Antitumor; Eupatorium; Humans; Inhibitory Concentration 50; isolation and purification; Magnetic Resonance Spectroscopy; pharmacology; Plant Roots; Thymol; Eupatorium cannabinum
Type
journal article