Journal
JOURNAL OF NATURAL PRODUCTS
Volume 72, Issue 7, Pages 1291-1298Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np900091y
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Funding
- NIH [P20RR 16456]
- National Center for Research Resources
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This study reports the isolation of nine new terpenoids (2-10), possessing two novel skeletons, from the Red Sea sponge Callyspongia (=Siphonochalina) siphonella. The identity of these novel skeletons was based oil X-ray crystallography and extensive spectral analyses. These compounds were evaluated for their ability to reverse P-glycoprotein (P-gp)-mediated multidrug resistance in human epidermoid cancer cells. Sipholenone E (3) was better than sipholenol A (1), a known P-gp modulator from this sponge, in reversing the P-gp-mediated multidrug resistance. Sipholenol L (6) and siphonellinol D (8) were nearly as active as sipholenol A. On the basis of X-ray crystallographic data and the established identity of 3-7, the structure of sipholenol 1 (11) is revised. A pharmacophore model of three hydrophobic points and two H-bond acceptors was generated for the active sipholane P-gp modulators.
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