Sutter R P, Dadok J, Bothner-By A A, Smith R R, Mishra P K
Department of Biology, West Virginia University, Morgantown 26506-6057.
Biochemistry. 1989 May 2;28(9):4060-6. doi: 10.1021/bi00435a064.
Trisporic acids are end products of the sex-specific pheromones in mucoraceous fungi. We have found three new trisporic acids in cultures of Blakeslea trispora in which (+) and (-) mating types were separated by a membrane with 0.45-microns pores. Two of the trisporic acids were new compounds; the structure of the third [previously described by Miller and Sutter [(1984) J. Biol. Chem. 259, 6420] as methyl trisporate-E with a hydroxyl group at C-2] was revised. Trisporic acid-E(3R), trisporic acid-E(3S), and trisporic acid-D(2S) were in a 1:1:2 ratio, accounted for 9% of the total trisporic acids, and differed by the position and configuration of a hydroxyl group on the ring at C-2 or C-3, the conformation of the ring, the extent of rotation of the side chain relative to the ring, and either a carbonyl or hydroxyl group on the side chain at C-13. These three compounds accounted for only 0.5% of the total trisporic acids in combined mating type cultures. Since the combined cultures did not metabolize trisporic acid-E(3R), its biosynthesis apparently ceases when opposing mating types contact each other physically. We speculate that B. trispora and Phycomyces blakesleeanus utilize different pheromones to regulate an early event (possibly zygotropism) in sexual development.
三孢酸是毛霉科真菌中性别特异性信息素的终产物。我们在三孢布拉氏霉的培养物中发现了三种新的三孢酸，其中（+）和（-）交配型被一个带有0.45微米孔径的膜隔开。其中两种三孢酸是新化合物；第三种三孢酸（先前由米勒和萨特[（1984年）《生物化学杂志》259卷，6420页]描述为在C-2位带有羟基的三孢酸甲酯-E）的结构得到了修正。三孢酸-E(3R)、三孢酸-E(3S)和三孢酸-D(2S)的比例为1:1:2，占总三孢酸的9%，它们在C-2或C-3位环上羟基的位置和构型、环的构象、侧链相对于环的旋转程度以及C-13位侧链上的羰基或羟基方面存在差异。这三种化合物在混合交配型培养物中仅占总三孢酸的0.5%。由于混合培养物不会代谢三孢酸-E(3R)，其生物合成显然在相反交配型相互物理接触时停止。我们推测三孢布拉氏霉和布氏梨囊霉利用不同的信息素来调节有性发育中的一个早期事件（可能是向合子性）。
