Isolation, structure elucidation, and synthesis of cytotoxic tryptanthrin analogues from Phaius mishmensis.
Bioassay-guided chromatographic separation of the cytotoxic MeOH extract of Phaius mishmensis led to the isolation of two known and six new indoloquinazolinones, phaitanthrins A-E (1-5) and methylisatoid (6). The structures of the new compounds were elucidated by spectroscopic analysis. Phaitanthrin A (1) and tryptanthrin (7) showed moderate cytotoxicity against MCF-7, NCI-H460, and SF-268 cell lines. A series of ketone adducts of tryptanthrin were prepared and tested initially for anticancer activity in vitro against MCF-7, NCI-H460, and SF-268 human cancer cell lines. The 3-pentanone adduct 13 showed activity similar to tryptanthrin.
Jao
Chen-Wei
CW
Department of Chemistry, National Cheng Kung University, Tainan, 701, Taiwan, Republic of China.
Lin
Wei-Chih
WC
Wu
Yao-Ting
YT
Wu
Pei-Lin
PL
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008968:Molecular Conformation; D015394:Molecular Structure; D029595:Orchidaceae / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry*; D011799:Quinazolines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D013624:Taiwan
D000972:Antineoplastic Agents, Phytogenic; D011799:Quinazolines; C046243:tryptanthrine