Isolation, structure elucidation, and synthesis of cytotoxic tryptanthrin analogues from Phaius mishmensis

Chen-Wei Jao; Wei-Chih Lin; Yao-Ting Wu; Pei-Lin Wu

doi:10.1021/np800064w

Isolation, structure elucidation, and synthesis of cytotoxic tryptanthrin analogues from Phaius mishmensis

J Nat Prod. 2008 Jul;71(7):1275-9. doi: 10.1021/np800064w. Epub 2008 May 29.

Authors

Chen-Wei Jao¹, Wei-Chih Lin, Yao-Ting Wu, Pei-Lin Wu

Affiliation

¹ Department of Chemistry, National Cheng Kung University, Tainan, 701, Taiwan, Republic of China.

PMID: 18507473
DOI: 10.1021/np800064w

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic* / chemistry
Antineoplastic Agents, Phytogenic* / isolation & purification
Antineoplastic Agents, Phytogenic* / pharmacology
Crystallography, X-Ray
Drug Screening Assays, Antitumor
Humans
Molecular Conformation
Molecular Structure
Orchidaceae / chemistry*
Plants, Medicinal / chemistry*
Quinazolines* / chemistry
Quinazolines* / isolation & purification
Quinazolines* / pharmacology
Taiwan

Substances

Antineoplastic Agents, Phytogenic
Quinazolines
tryptanthrine