RRC ID 41374
著者 Komatsu H, Watanabe M, Ohyama M, Enya T, Koyama K, Kanazawa T, Kawahara N, Sugimura T, Wakabayashi K.
タイトル Phenanthroindolizidine alkaloids as cytotoxic substances in a Danaid butterfly, Ideopsis similis, against human cancer cells.
ジャーナル J Med Chem
Abstract We previously reported the presence of cytotoxic substances in extracts of the Danaid butterfly, Ideopsis similis. In the present study, we isolated cytotoxic substances against a human gastric cancer cell line, TMK-1, in I. similis pupae, with an activity similar to that of the adult butterfly. The basic fraction, prepared from a methanol extract, accounted for 83% of the cytotoxic activity. Two major cytotoxic substances were purified by HPLC, and one was determined to be a new phenanthroindolizidine alkaloid, trans-(+)-3,14alpha-dihydroxy-6,7-dimethoxyphenanthroindolizidine (1), and the other a known compound, trans-(+)-3,14alpha-dihydroxy-4,6,7-trimethoxyphenanthroindolizidine (2). The IC(50) values for TMK-1 cells were 0.5 ng/mL and 0.7 ng/mL, respectively. These two compounds showed similar cytotoxic potential with four other cancer cell lines including cervical, lung, and colon carcinomas and leukemia. Quantitative analyses indicated the presence of each of the two phenanthroindolizidine alkaloids at levels of 11-74 microg in each larva, pupa, or adult of I. similis. However, 1 was not detected in the leaves of Tylophora tanakae, a host plant for larvae of I. similis, and the level of 2 (2 microg per gram of leaves) was far less than that in the larvae. Since the leaves of T. tanakae are known to contain various phenanthroindolizidines, compounds 1 and 2 are presumably metabolically converted from such alkaloids in larvae of I. similis.
巻・号 44(11)
ページ 1833-6
公開日 2001-5-24
DOI 10.1021/jm0004042
PII jm0004042
PMID 11356117
MeSH Alkaloids / chemistry Alkaloids / isolation & purification Alkaloids / pharmacology* Animals Antineoplastic Agents / chemistry Antineoplastic Agents / isolation & purification Antineoplastic Agents / pharmacology* Butterflies / chemistry* Chromatography, High Pressure Liquid Drug Screening Assays, Antitumor Humans Indolizines / chemistry Indolizines / isolation & purification Indolizines / pharmacology* Magnetic Resonance Spectroscopy Phenanthrenes / chemistry Phenanthrenes / isolation & purification Phenanthrenes / pharmacology* Plant Leaves / chemistry Tumor Cells, Cultured
IF 6.205
引用数 38
WOS 分野 CHEMISTRY, MEDICINAL
リソース情報
ヒト・動物細胞 HeLa(RCB0007)