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.
Ross
Samir A
SA
National Center for Natural Products Research and Department of Pharmacognosy, School of Pharmacy, University of Mississippi, University, Mississippi 38677-1848, USA. sross@olemiss.edu
Rodríguez-Guzmán
Raquel
R
Radwan
Mohamed M
MM
Jacob
Melissa
M
Ding
Yuanqing
Y
Li
Xing-Cong
XC
Ferreira
Daneel
D
Manly
Susan P
SP
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