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Cytotoxic Isoprenylated Flavonoids from the Roots of Sophora flavescens
Author(s) -
Ding Peilan,
Chen Daofeng,
Bastow Kenneth F.,
Nyarko Alexander K.,
Wang Xihong,
Lee KuoHsiung
Publication year - 2004
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.200490230
Subject(s) - chemistry , sophora flavescens , cytotoxic t cell , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , cell culture , epidermoid carcinoma , traditional medicine , carcinoma , biochemistry , in vitro , medicine , matrine , chromatography , biology , genetics
Three new flavonoids, which are isoprenylated by fused 2,2‐dimethyl‐3,4‐dihydro‐2 H ‐pyran moieties, were isolated from the roots of Sophora flavescens and named flavenochromanes A–C ( 1 – 3 ). Their structures were elucidated by spectroscopic methods, including 2D‐NMR techniques. Flavenochromane C ( 3 ) showed strong cytotoxic activity against A549 (lung carcinoma), 1A9 (ovarian carcinoma), KB (epidermoid carcinoma of the nasopharynx), and KB‐Vin (drug‐resistant variant KB) cell lines with IC 50 values ≤1.7 μ M , and significant activity against the MCF‐7 (breast adenocarcinoma) cell line with an IC 50 value of 3.6 μ M . Flavenochromane B ( 2 ) displayed slightly lower inhibitory effects ( IC 50 3.2–6.9 μ M ) as compared with 3 .