Bioactive triterpene glycosides from the sea cucumber Holothuria fuscocinerea.
Bioassay-guided fractionation of the active n-BuOH extract of the sea cucumber Holothuria fuscocinerea resulted in the isolation of three new triterpene glycosides, fuscocinerosides A (1), B (2), and C (3), along with two known glycosides, pervicoside C (4) and holothurin A (5), as active compounds causing morphological abnormality of Pyricularia oryzae mycelia. Compounds 1-5 possess the same tetrasaccharide moiety, 3-O-methyl-beta-D-glucopyranosyl-(1-->3)-beta-D- glucopyranosyl-(1-->4)-beta-D-quinovopyranosyl-(1-->2)-4-O-sodiumsulfato-beta-D-xylopyranosyl, linked to C-3 of holostane triterpene aglycones that differ in their side chains and 17-substituents. Their structures were elucidated by extensive spectral studies as well as chemical evidence. All the glycosides showed in vitro cytotoxicity against two human tumor cell lines.
Zhang
Shu-Yu
SY
Research Center for Marine Drugs, School of Pharmacy, Second Military Medical University, Shanghai 200433, People's Republic of China.
Yi
Yang-Hua
YH
Tang
Hai-Feng
HF
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D012616:Sea Cucumbers / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology
D000970:Antineoplastic Agents; D006027:Glycosides; D014315:Triterpenes; C515360:fuscocineroside A; C515361:fuscocineroside B; C515362:fuscocineroside C