Article

The Calyculaglycosides: Dilophol-Type Diterpene Glycosides Exhibiting Antiinflammatory Activity from the Caribbean Gorgonian Eunicea sp.(1)(,)(2).

Department of Chemistry, University of Puerto Rico, P.O. Box 23346, U.P.R. Station, Río Piedras, Puerto Rico 00931-3346 and Instituto de Ciencias Naturales-Museo de Historia Natural, Universidad Nacional de Colombia, Colombia.
The Journal of Organic Chemistry (impact factor: 4.45). 11/1997; 62(21):7183-7188. pp.7183-7188
Source: PubMed

ABSTRACT Three new diterpenoid hexose-glycosides, calyculaglycosides A-C (1-3) were isolated from the Caribbean gorgonian Eunicea sp. Calyculaglycosides A-C are rare diterpene glycosides possessing dilophol (4) aglycones related in biosynthetic origin to the elemene-type glycoside class of potent antiinflammatory agents known as fuscosides. The structures of the new compounds, which were assigned on the basis of spectral studies, were further corroborated by molecular modeling studies. Calyculaglycoside B (2) is an effective topical antiinflammatory agent stronger in potency than the industrial standard indomethacin. Calyculaglycoside B inhibits the synthesis of both prostaglandin PGE(2) and leukotriene LTB(4), suggesting it is a nonselective inhibitor of the 5-lipoxygenase and cyclooxygenase pathways. At concentrations of 10(-4)-10(-5)M, calyculaglycoside B produced LC(50)-level differential responses against a majority of the NCI ovarian cancer lines and several of the renal, prostate, and colon tumor lines.

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Keywords

5-lipoxygenase
 
biosynthetic origin
 
Caribbean gorgonian Eunicea sp
 
effective topical antiinflammatory agent stronger
 
elemene-type glycoside class
 
fuscosides
 
industrial standard indomethacin
 
LC(50)-level differential responses
 
leukotriene LTB(4)
 
molecular modeling studies
 
new compounds
 
new diterpenoid hexose-glycosides
 
potent antiinflammatory agents
 
prostaglandin PGE(2)
 
renal