4.7 Article

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

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 71, Issue 10, Pages 1764-1767

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/np800446g

Keywords

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Funding

  1. NIH IMSD Biomedical Research Internship [GM55379]
  2. University of Mississippi Graduate Honors Fellowship
  3. Department of Pharmacognosy
  4. NIH
  5. NIAID
  6. Division of AIDS [AI 27094]
  7. USDA Agricultural Research Service Specific Cooperative [58-6408-2-0009]

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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 I and 2 were established by analysis of their experimental and theoretically calculated CD spectra. Compounds I and 2 showed significant and selective activity against methicillin-resistant Staphylococcus aureus with IC(50) values of 1.5 and 0.5 mu M, 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 mu M, respectively.

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