4.7 Article

Anti-inflammatory 12,20-Epoxypregnane and 11,12-seco-Pregnane Glycosides from the Stems of Hoya kerrii

Journal

JOURNAL OF NATURAL PRODUCTS
Volume 80, Issue 6, Pages 1714-1724

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.6b00730

Keywords

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Funding

  1. Thailand Research Fund [BRG5580012]
  2. Ramkhamhaeng University
  3. Royal Golden Jubilee Ph.D. Program
  4. Thailand Research Fund
  5. Center of Excellence for Innovation in Chemistry (PERCH-CIC)
  6. Commission on Higher Education
  7. Ministry of Education
  8. Mahidol University
  9. Office of the Higher Education Commission under the National Research Universitites Initiative

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Five 12,20-epoxypregnane glycosides (1-3, 5, and 6) and two 11,12-seco-pregnane glycosides (4 and 7) with spirodilactone motifs, as well as spirodilactone cleavage products 8 and 9, were isolated from the stems of Hoya kerrii. The relative configurations of the three related skeletons were supported by ROESY experiments and X-ray crystallographic analyses. The isolates were evaluated for their anti-inflammatory activity based on the inhibition of NO production in RAW264.7 cells, and some showed IC50 values ranging from 12.6 to 96.5 mu M. The most potent compound, 9a, was also examined for its anti-inflammatory mechanism against mRNA expression and was found to down-regulate mRNA expression of iNOS and COX-2 in a dose-dependent manner.

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