Cytotoxic phenanthrenequinones and 9,10-dihydrophenanthrenes from Calanthe arisanensis.

Abstract

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.

• Authors: Chia-Lin Lee, Fang-Rong Chang, Ming-Hon Yen, Donglei Yu, Yi-Nan Liu, Kenneth F Bastow, Susan L Morris-Natschke, Yang-Chang Wu, Kuo-Hsiung Lee
• Journal: Journal of natural products (J Nat Prod) Vol. 72 Issue 2 Pg. 210-3 (Feb 27 2009) ISSN: 1520-6025 [Electronic] United States
• PMID: 19193043 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents, Phytogenic
• Phenanthrenes
• Quinones
• Vincristine

Topics

• Antineoplastic Agents, Phytogenic (chemistry, isolation & purification, pharmacology)
• Drug Resistance, Neoplasm (drug effects)
• Drug Screening Assays, Antitumor
• Female
• Humans
• Male
• Molecular Structure
• Orchidaceae (chemistry)
• Phenanthrenes (chemistry, isolation & purification, pharmacology)
• Plants, Medicinal (chemistry)
• Quinones (chemistry, isolation & purification, pharmacology)
• Vincristine (pharmacology)