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Cytotoxic calanquinone A from Calanthe arisanensis and its first total synthesis.

ABSTRACT: Calanquinone A (1) was isolated from an EtOAc-soluble extract of Calanthe arisanensis through bioassay-guided fractionation. Its structure was identified by spectroscopic methods. Compound 1 showed potent cytotoxicity (EC(50)<0.5microg/mL) against lung (A549), prostate (PC-3 and DU145), colon (HCT-8), breast (MCF7), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KB-VIN) cancer cell lines, and interestingly, showed an improved drug resistance profile compared to paclitaxel. The total synthesis of 1 was also achieved and is reported herein.

SUBMITTER: Lee CL

PROVIDER: S-EPMC2551759 | biostudies-literature | 2008 Aug

REPOSITORIES: biostudies-literature

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Cytotoxic calanquinone A from Calanthe arisanensis and its first total synthesis.

Lee Chia-Lin CL Nakagawa-Goto Kyoko K Yu Donglei D Liu Yi-Nan YN Bastow Kenneth F KF Morris-Natschke Susan L SL Chang Fang-Rong FR Wu Yang-Chang YC Lee Kuo-Hsiung KH

Bioorganic & medicinal chemistry letters 20080703 15

Calanquinone A (1) was isolated from an EtOAc-soluble extract of Calanthe arisanensis through bioassay-guided fractionation. Its structure was identified by spectroscopic methods. Compound 1 showed potent cytotoxicity (EC(50)<0.5microg/mL) against lung (A549), prostate (PC-3 and DU145), colon (HCT-8), breast (MCF7), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KB-VIN) cancer cell lines, and interestingly, showed an improved drug resistance profile compared to paclitaxel. The to ...[more]

PMID: 18640035

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