Sorocenols G and H, Anti-MRSA Oxygen Heterocyclic Diels−Alder-Type Adducts from Sorocea muriculata Roots

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2008-10, Vol.71 (10), p.1764-1767
• Main Authors: Ross, Samir A, Rodríguez-Guzmán, Raquel, Radwan, Mohamed M, Jacob, Melissa, Ding, Yuanqing, Li, Xing-Cong, Ferreira, Daneel, Manly, Susan P
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - isolation & purification; Anti-Bacterial Agents - pharmacology; antibacterial properties; Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; antifungal properties; Aspergillus fumigatus; Aspergillus fumigatus - drug effects; Benzofurans - chemistry; Benzofurans - isolation & purification; Biological and medical sciences; Candida albicans; Candida albicans - drug effects; chemical structure; Cryptococcus neoformans; Cryptococcus neoformans - drug effects; cultured cells; cytotoxicity; General pharmacology; heterocyclic oxygen compounds; Inhibitory Concentration 50; Medical sciences; medicinal plants; medicinal properties; Methicillin Resistance - drug effects; Microbial Sensitivity Tests; Molecular Structure; Moraceae; Moraceae - chemistry; Oxygen - chemistry; Peru; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Roots - chemistry; Sorocea muriculata; sorocenol; spectral analysis; Staphylococcus aureus; Staphylococcus aureus - drug effects; Stilbenes - chemistry; Stilbenes - isolation & purification
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800446g

Bioassay-guided fractionation of a root extract of Sorocea muriculata led to the isolation and identification of two new oxygen heterocyclic Diels−Alder-type adducts, sorocenols G (1) and H (2), along with lupeol-3-(3′R-hydroxytetradecanoate) and oxyresveratrol. The structures of 1 and 2 were elucidated using 1D and 2D NMR spectroscopic and HRMS data and by comparison with reported values. The absolute configurations of 1 and 2 were established by analysis of their experimental and theoretically calculated CD spectra. Compounds 1 and 2 showed significant and selective activity against methicillin-resistant Staphylococcus aureus with IC50 values of 1.5 and 0.5 μM, respectively. Compound 2 also displayed antifungal activity against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus, with IC50 values of 5.4, 5.4, and 10.0 μM, respectively.