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Abstract
A new bioactive sterol glycoside, 3β-O-(3′,4′-di-O-acetyl-β-d-arabinopyranosyl) -25ξ-cholestane-3β,5α,6β,26-tetrol-26-acetate) (carijoside A, 1), was isolated from an octocoral identified as Carijoa sp. The structure of glycoside 1 was established by spectroscopic methods and by comparison with spectral data for the other known glycosides. Carijoside A (1) displayed significant inhibitory effects on superoxide anion generation and elastase release by human neutrophils and this compound exhibited moderate cytotoxicity toward DLD-1, P388D1, HL-60, and CCRF-CEM tumor cells.
Highlights
Previous studies on the chemical constituents from the octocorals belonging to the genus Carijoa (=Telesto) have yielded a series of bioactive substances including amide [1], steroid [1,2,3,4], and prostanoid analogs [3,5]
Analysis of 2D NMR experiments revealed that carijoside A (1) was a pentose glycoside derivative of a known trihydroxy sterol, cholestane-3,5,6 -tetrol-26-acetate (=25 -cholestane-3,5,6,26-tetrol26-acetate) (2), a cytotoxic steroid previously isolated from Telesto riisei, collected from Northeast
Human neutrophils were obtained by means of dextran sedimentation and Ficoll centrifugation
Summary
Previous studies on the chemical constituents from the octocorals belonging to the genus Carijoa (=Telesto) have yielded a series of bioactive substances including amide [1], steroid [1,2,3,4], and prostanoid analogs [3,5]. In our continuing studies on the chemical constituents of octocorals distributed in Taiwan waters, a new sterol glycoside, carijoside A (1) (Figure 1) was isolated from an octocoral identified as Carijoa sp. The structure of 1 was determined by spectroscopic methods and by comparison of spectral data with those of known sterols. We describe the isolation, structure determination, and bioactivity of glycoside 1
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