Steroidal triglycosides, kurilensosides A, B, and C, and other polar steroids from the Far Eastern starfish Hippasteria kurilensis.
Three novel steroidal triglycosides, designated as kurilensosides A, B, and C (1- 3), were isolated along with a new steroidal diglycoside, kurilensoside D (4), and two new (6, 7) and one known (5) polyhydroxysteroid from the alcoholic extract of the Far Eastern starfish Hippasteria kurilensis. Compounds 1-3 are the first triglycosides containing two carbohydrate chains found from starfish. The structures of 1-7 were elucidated by spectroscopic methods (mainly 2D NMR) and chemical derivatization. Glycosides 1-4 and steroids 6 and 7 inhibited sea urchin egg fertilization by sperm preincubated with these compounds.
Kicha
Alla A
AA
Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russian Federation.
Ivanchina
Natalia V
NV
Kalinovsky
Anatoly I
AI
Dmitrenok
Pavel S
PS
Agafonova
Irina G
IG
Stonik
Valentin A
VA
D000818:Animals; D005306:Fertilization / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008297:Male; D015394:Molecular Structure; D010063:Ovum / Q000187:drug effects; D012426:Russia; D013094:Spermatozoa / Q000187:drug effects; D013215:Starfish / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D006027:Glycosides; D013256:Steroids; C530180:kurilensoside A; C530181:kurilensoside B; C530182:kurilensoside C