Max Planck Institute for Chemical Ecology, Department of Bioorganic Chemistry, Hans-Knöll-Strasse 8, D-07745 Jena, Germany.
J Org Chem. 2010 Jun 18;75(12):3958-64. doi: 10.1021/jo1004372.
During sexual reproduction, female gametes or eggs of brown algae release pheromones to attract their male mating partners. The biologically active compounds comprise linear or alicyclic unsaturated hydrocarbons derived from the aliphatic terminus of C(20) polyunsaturated fatty acids (PUFAs) by oxidative cleavage. The current study addresses the stereochemical course of the pheromone biosynthesis using female gametes of the marine brown alga E. siliculosus and chiral deuterium-labeled arachidonic acids. The biosynthetic sequence is likely to proceed via an intermediary 9-hydroperoxyarachidonic acid, which is cleaved with loss of the C(16)-H(R) into the C(11)-hydrocarbon dictyopterene C and 9-oxonona-(5Z,7E)-dienoic acid.
在有性生殖过程中，褐藻的雌性配子或卵子会释放信息素来吸引雄性交配伙伴。这些具有生物活性的化合物由来自 C(20)多不饱和脂肪酸 (PUFA) 脂肪端的线性或脂环不饱和烃组成，通过氧化裂解而来。本研究使用海洋褐藻 E. siliculosus 的雌性配子和手性氘标记的花生四烯酸来研究信息素生物合成的立体化学过程。生物合成序列可能通过中间体 9-羟过氧花生四烯酸进行，该酸在失去 C(16)-H(R)后裂解，生成 C(11)-碳氢化合物二萜烯 C 和 9-氧代壬-(5Z,7E)-二烯酸。
