title: 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.
authors.affiliation: Natural Products Research Laboratories, School of Pharmacy, University of North Carolina at Chapel Hill, 315 Beard Hall, CB# 7360, NC 27599-7360, USA.
authors.forename: Chia-Lin
authors.initials: CL
authors.lastname: Lee
authors.forename: Kyoko
authors.initials: K
authors.lastname: Nakagawa-Goto
authors.forename: Donglei
authors.initials: D
authors.lastname: Yu
authors.forename: Yi-Nan
authors.initials: YN
authors.lastname: Liu
authors.forename: Kenneth F
authors.initials: KF
authors.lastname: Bastow
authors.forename: Susan L
authors.initials: SL
authors.lastname: Morris-Natschke
authors.forename: Fang-Rong
authors.initials: FR
authors.lastname: Chang
authors.forename: Yang-Chang
authors.initials: YC
authors.lastname: Wu
authors.forename: Kuo-Hsiung
authors.initials: KH
authors.lastname: Lee
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D019008:Drug Resistance, Neoplasm / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D008297:Male; D029595:Orchidaceae / Q000737:chemistry*; D017239:Paclitaxel / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D014750:Vincristine / Q000494:pharmacology
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D011809:Quinones; C530567:calanquinone A; D014750:Vincristine; D017239:Paclitaxel