DISCOVERY AND DEVELOPMENT OF NATURAL PRODUCTS FOR PHARMACEUTICAL AND AGRICHEMICAL APPLICATIONS
Location: Natural Products Utilization Research
Title: Sorocenols G and H, Anti-MRSA Oxygen Heterocyclic Diels-Alder-type Adducts from Sorocea muriculata Roots
| Ross, Samir - |
| Rodriguez-Guzman, Raquel - |
| Radwan, Mohamed - |
| Jacob, Melissa - |
| Ding, Yuanqing - |
| Li, Xing-Cong - |
| Ferreira, Daneel - |
| Manly, Susan - |
Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 20, 2008
Publication Date: October 11, 2008
Citation: Ross, S.A., Rodriguez-Guzman, R., Radwan, M.M., Jacob, M., Ding, Y., Li, X., Ferreira, D., Manly, S.P. 2008. Sorocenols G and H, Anti-MRSA Oxygen Heterocyclic Diels-Alder-type Adducts from Sorocea muriculata Roots. Journal of Natural Products. 71(10):1764-1767.
Interpretive Summary: Two new oxygen heterocyclic Diels-Alder adducts have been isolated and identified from the root extract of Soracea muriculata. The isolated compounds exhibited significant and selective activity against Methicillin-Resistant Staphylococcus aureus.
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.