Cytotoxic phenanthrenequinones and 9,10-dihydrophenanthrenes from Calanthe arisanensis.
Two new phenanthrenequinones, calanquinones B and C (2 and 3) and four new 9,10-dihydrophenanthrenes, calanhydroquinones A-C (4-6) and calanphenanthrene A (7), along with five known compounds (1 and 8-11), were isolated from an EtOAc-soluble extract of Calanthe arisanensis through bioassay-guided fractionation. Their structures were identified from spectroscopic data, and the compounds were tested for in vitro cytotoxic activity against human lung (A549), prostate (PC-3 and DU145), colon (HCT-8), breast (MCF-7), nasopharyngeal (KB), and vincristine-resistant nasopharyngeal (KBVIN) cancer cell lines. Compound 1 showed the highest potency (EC(50) < 0.5 microg/mL) against all seven cancer cell lines, with the greatest activity against breast cancer MCF-7 cells (EC(50) < 0.02 microg/mL). Generally, except for 7, compounds 2-11 also showed significant cytotoxic activity (EC(50) < 4 microg/mL) against some cell lines (especially PC-3 and MCF-7) in the panel.
Lee
Chia-Lin
CL
Natural Products Research Laboratories, Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599, USA.
Chang
Fang-Rong
FR
Yen
Ming-Hon
MH
Yu
Donglei
D
Liu
Yi-Nan
YN
Bastow
Kenneth F
KF
Morris-Natschke
Susan L
SL
Wu
Yang-Chang
YC
Lee
Kuo-Hsiung
KH
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D019008:Drug Resistance, Neoplasm / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005260:Female; D006801:Humans; D008297:Male; D015394:Molecular Structure; D029595:Orchidaceae / Q000737:chemistry*; D010616:Phenanthrenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D010946:Plants, Medicinal / Q000737:chemistry*; D011809:Quinones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014750:Vincristine / Q000494:pharmacology
D000972:Antineoplastic Agents, Phytogenic; D010616:Phenanthrenes; D011809:Quinones; D014750:Vincristine