Atropisomeric Myristinins: Selective COX-2 Inhibitors and Antifungal Agents from Myristica cinnamomea

The first naturally occurring atropisomeric flavans, myristinins B (2), C (2a), E (4), and F (4a), together with their corresponding trans-isomers, myristinins A (1) and D (3), were isolated from the CH(2)Cl(2) extract of Myristica cinnamomea fruits. Compounds 1, the mixture of 2 and 2a, and the mix...

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Veröffentlicht in:	Journal of organic chemistry 2002-08, Vol.67 (16), p.5470-5475
Hauptverfasser:	SAWADJOON, Supaporn, KITTAKOOP, Prasat, KIRTIKARA, Kanyawim, VICHAI, Vanicha, TANTICHAROEN, Morakot, THEBTARANONTH, Yodhathai
Format:	Artikel
Sprache:	eng
Schlagworte:	Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Biological and medical sciences Cyclooxygenase 2 Cyclooxygenase 2 Inhibitors Cyclooxygenase Inhibitors - chemical synthesis Cyclooxygenase Inhibitors - chemistry Cyclooxygenase Inhibitors - pharmacology Drug Design Flavonoids - chemical synthesis Flavonoids - chemistry Flavonoids - pharmacology General pharmacology Indicators and Reagents Isoenzymes - metabolism Isomerism Magnetic Resonance Spectroscopy Medical sciences Molecular Conformation Molecular Structure Myristicaceae - chemistry Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments Prostaglandin-Endoperoxide Synthases - metabolism Structure-Activity Relationship
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Zusammenfassung:	The first naturally occurring atropisomeric flavans, myristinins B (2), C (2a), E (4), and F (4a), together with their corresponding trans-isomers, myristinins A (1) and D (3), were isolated from the CH(2)Cl(2) extract of Myristica cinnamomea fruits. Compounds 1, the mixture of 2 and 2a, and the mixture of 4 and 4a, exhibited antifungal activity against Candida albicans with IC(50) values ranging from 5.9 to 8.8 microg/mL, and they selectively inhibited the enzyme cyclooxygenase-2 (COX-2).
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo020045d