Relationship between cytotoxic activity and radical intensity of isoflavones from Sophora species.
Among 11 isoflavones tested, genistein [YS13] produced higher cytotoxic activity against human oral tumor cell lines (HSC-2, HSG) than against normal cells (human gingival fibroblast, HGF), suggesting its tumor-specific action. Electron spin resonance (ESR) spectroscopy showed that YS13 did not produce radical, nor scavenged O2*- generated by hypoxanthine-xanthine oxidase reaction system, suggesting that radical-mediated oxidation mechanism is not be involved in the YS13-induced cytotoxicity. Addition of one prenyl group produced YS18 and YS19 with higher anti-Helicobacter pylori activity. Addition of two prenyl groups produced YS21 with the highest cytotoxic activity but lower tumor-specificity. Since YS21 produced the highest amount of radical and most efficiently scavenged O2*-, this compound may induce cytotoxicity by radical-mediated oxidation mechanism. All isoflavones failed to induce anti-human immunodeficiency virus (HIV) activity. These data suggest the medicinal efficacy of isoflavones.
Shirataki
Y
Y
Faculty of Pharmaceutical Sciences, Josai University, Sakado, Saitama, Japan. shiratak@josai.ac.jp
Tani
S
S
Sakagami
H
H
Satoh
K
K
Nakashima
H
H
Gotoh
K
K
Motohashi
N
N
D000818:Animals; D000900:Anti-Bacterial Agents; D019380:Anti-HIV Agents / Q000737:chemistry / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000737:chemistry / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000633:toxicity*; D002294:Carcinoma, Squamous Cell / Q000188:drug therapy; D002417:Cattle; D004354:Drug Screening Assays, Antitumor; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D005881:Gingiva / Q000166:cytology / Q000187:drug effects; D006678:HIV / Q000187:drug effects; D016480:Helicobacter pylori / Q000187:drug effects; D006801:Humans; D007529:Isoflavones / Q000737:chemistry / Q000633:toxicity*; D009062:Mouth Neoplasms / Q000188:drug therapy; D012468:Salivary Gland Neoplasms / Q000188:drug therapy; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000378:metabolism
D000900:Anti-Bacterial Agents; D019380:Anti-HIV Agents; D000890:Anti-Infective Agents; D000970:Antineoplastic Agents; D016166:Free Radical Scavengers; D007529:Isoflavones; D013481:Superoxides