Suntory Institute for Bioorganic Research, Shimamoto, Mishima, 618, Osaka, Japan.
J Chem Ecol. 1992 Nov;18(11):2083-94. doi: 10.1007/BF00981929.
Ergosta-5,7,24(28)-trien-3β-ol (trienol)6 was isolated from the intracellular symbiotes (symbiotic microorganisms) of the planthoppers,Nilaparvata lugens andLaodelphax striatellus. The steroidogenic end product of the symbiotes was found to depend on the environmental conditions, i.e., although trienol6 was produced under symbiotic conditions, ergosterol4 was formed in aerobic culture. When the normal diet was replaced by a steroiddeficient artificial one, the ratio of 24-methylenecholesterol5 to total insect sterols was significantly increased. The above study offers further corroborating evidence for our assumption that the host insects require 24-methylenecholesterol5 as an alternate source for cholesterol1 under certain environmental conditions. In our previous biotransformation experiments, 24methylenecholesterol5 was shown to be an immediate precursor of cholesterol1. However, the complexity of the insects' vital functions hindered all subsequent attempted transformations into cholesterol1 of sitosterol2, trienol6, and ergosterol4, under injection conditions.
麦角甾-5,7,24(28)-三烯-3β-醇(三烯醇)6 从稻褐飞虱和白背飞虱的细胞内共生体(共生微生物)中分离得到。共生体的甾醇生物合成终产物取决于环境条件,即在共生条件下产生三烯醇 6,而在需氧培养中形成麦角甾醇 4。当用缺乏类固醇的人工正常饮食替代正常饮食时,24-亚甲基胆固醇 5 与昆虫总甾醇的比例显著增加。上述研究为我们的假设提供了进一步的佐证,即在某些环境条件下,宿主昆虫需要 24-亚甲基胆固醇 5 作为胆固醇 1 的替代来源。在我们之前的生物转化实验中,24-亚甲基胆固醇 5 被证明是胆固醇 1 的直接前体。然而,昆虫生命功能的复杂性阻碍了所有后续试图在注射条件下将豆甾醇 2、三烯醇 6 和麦角甾醇 4 转化为胆固醇 1 的尝试。