Sorocenols G and H, anti-MRSA oxygen heterocyclic Diels-Alder-type adducts from Sorocea muriculata roots.
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 microM, respectively. Compound 2 also displayed antifungal activity against Candida albicans, Cryptococcus neoformans, and Aspergillus fumigatus, with IC 50 values of 5.4, 5.4, and 10.0 microM, respectively.
National Center for Natural Products Research and Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, Mississippi 38677-1848, USA. sross@olemiss.edu
Samir A
SA
Ross
Raquel
R
Rodríguez-Guzmán
Mohamed M
MM
Radwan
Melissa
M
Jacob
Yuanqing
Y
Ding
Xing-Cong
XC
Li
Daneel
D
Ferreira
Susan P
SP
Manly
D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D001232:Aspergillus fumigatus / Q000187:drug effects; D001572:Benzofurans / Q000737:chemistry* / Q000302:isolation & purification*; D002176:Candida albicans / Q000187:drug effects; D003455:Cryptococcus neoformans / Q000187:drug effects; D020128:Inhibitory Concentration 50; D016106:Methicillin Resistance / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D029586:Moraceae / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D010568:Peru; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D018517:Plant Roots / Q000737:chemistry; D013211:Staphylococcus aureus / Q000187:drug effects*; D013267:Stilbenes / Q000737:chemistry / Q000302:isolation & purification
D000900:Anti-Bacterial Agents; D000935:Antifungal Agents; D001572:Benzofurans; D010936:Plant Extracts; D013267:Stilbenes; C532997:sorocenol G; C532998:sorocenol H; C034912:puag-haad; D010100:Oxygen