Steroidal Triglycosides, Kurilensosides A, B, and C, and Other Polar Steroids from the Far Eastern Starfish Hippasteria kurilensis

• Published in: Journal of natural products (Washington, D.C.) Vol. 71; no. 5; pp. 793 - 798
• Main Authors: Kicha, Alla A., Ivanchina, Natalia V., Kalinovsky, Anatoly I., Dmitrenok, Pavel S., Agafonova, Irina G., Stonik, Valentin A.
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 01.05.2008; Amer Chemical Soc
• Subjects: Animals; Chemistry, Medicinal; Fertilization - drug effects; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Life Sciences & Biomedicine; Male; Molecular Structure; Ovum - drug effects; Pharmacology & Pharmacy; Plant Sciences; Russia; Science & Technology; Spermatozoa - drug effects; Starfish - chemistry; Steroids - chemistry; Steroids - isolation & purification; Steroids - pharmacology; Russia; GLYCOSIDES; SAPONINS
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np070637x

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.