Cytotoxic calanquinone A from Calanthe arisanensis and its first total synthesis.
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.
Lee
Chia-Lin
CL
Natural Products Research Laboratories, School of Pharmacy, University of North Carolina at Chapel Hill, 315 Beard Hall, CB# 7360, NC 27599-7360, USA.
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
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
D000972:Antineoplastic Agents, Phytogenic; D011809:Quinones; C530567:calanquinone A; D014750:Vincristine; D017239:Paclitaxel