title: Biosynthesis of polar steroids from the Far Eastern starfish Patiria (=Asterina) pectinifera. Cholesterol and cholesterol sulfate are converted into polyhydroxylated sterols and monoglycoside asterosaponin P1 in feeding experiments.
abstract: For the first time, it is experimentally established that the dietary cholesterol and cholesterol sulfate are biosynthetic precursors of polyhydroxysteroids and related low molecular weight glycosides in starfishes. These deuterium labeled precursors were converted into partly deuterated 5α-cholestane-3β,6α,7α,8,15α,16β,26-heptaol, 5α-cholestane-3β,4β,6α,7α,8,15β,16β,26-octaol, and steroid monoside asterosaponin P1 in result of feeding experiments on the Far Eastern starfish Patiria (=Asterina) pectinifera. The incorporations of deuterium were established by MS and NMR spectroscopy. Scheme of the first stages of biosynthesis of polar steroids in these animals was suggested on the basis of inclusion of three from six deuterium atoms and determination of their positions in biosynthetic products, when [2,2,3,4,4,6-(2)H6]cholesterol 3-sulfate was used as precursor. It was also shown that labeled cholesterol is transformed into Δ(7)-cholesterol (lathosterol) in digestive organs and gonads of the starfish.
authors.affiliation: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Pr. 100-let Vladivostoku 159, 690022 Vladivostok, Russia.
authors.forename: Natalia V
authors.initials: NV
authors.lastname: Ivanchina
authors.forename: Alla A
authors.initials: AA
authors.lastname: Kicha
authors.forename: Timofey V
authors.initials: TV
authors.lastname: Malyarenko
authors.forename: Anatoly I
authors.initials: AI
authors.lastname: Kalinovsky
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Dmitrenok
authors.forename: Valentin A
authors.initials: VA
authors.lastname: Stonik
mesh_terms: D000818:Animals; D053898:Biosynthetic Pathways; D002776:Cholestanes / Q000378:metabolism*; D002784:Cholesterol / Q000378:metabolism; D002788:Cholesterol Esters / Q000378:metabolism*; D004041:Dietary Fats / Q000378:metabolism; D012503:Saponins / Q000096:biosynthesis*; D013215:Starfish / Q000378:metabolism*; D013256:Steroids / Q000096:biosynthesis
chemical_list: D002776:Cholestanes; D002788:Cholesterol Esters; D004041:Dietary Fats; D012503:Saponins; D013256:Steroids; D002784:Cholesterol; C007045:cholesteryl sulfate
keywords: Biosynthesis; Polyhydroxysteroids; Starfish