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

Chen Wei Jao, Wei Chih Lin, Yao Ting Wu, Pei Lin Wu

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

189 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1275-1279
Number of pages	5
Journal	Journal of Natural Products
Volume	71
Issue number	7
DOIs	https://doi.org/10.1021/np800064w
Publication status	Published - 2008 Jul

All Science Journal Classification (ASJC) codes

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np800064w

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

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.",

author = "Jao, {Chen Wei} and Lin, {Wei Chih} and Wu, {Yao Ting} and Wu, {Pei Lin}",

year = "2008",

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T1 - Isolation, structure elucidation, and synthesis of cytotoxic tryptanthrin analogues from Phaius mishmensis

AU - Jao, Chen Wei

AU - Lin, Wei Chih

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AU - Wu, Pei Lin

PY - 2008/7

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AB - 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.

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

Abstract

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