Lehrstuhl für Genetik, Technische Universität München, Freising, Germany.
Phytochemistry. 2009 Oct-Nov;70(15-16):1638-44. doi: 10.1016/j.phytochem.2009.05.002. Epub 2009 Jun 10.
Structurally related secondary products are rather rarely shared by organisms from different kingdoms. Consequently, the evolution of biosynthetic pathways of defence metabolites between distantly related organisms has not been broadly investigated. Thiazolylindoles are found in Arabidopsis thaliana, as the phytoalexin camalexin, and in a Streptomyces strain, which synthesizes a tumour-inhibitory derivative, designated BE-10988. Camalexin originates from cysteine and tryptophan, which is converted to indole-3-acetaldoxime and subsequently dehydrated to indole-3-acetonitrile. The metabolic origin of BE-10988 was determined by retrobiosynthetic NMR analysis and incorporation studies with direct precursors. Like camalexin, it is derived from tryptophan and cysteine. However, as BE-10988 is synthesized via indole-3-pyruvic acid, not via indole-3-acetaldoxime, independent mechanisms of tryptophan modification have evolved.
结构相关的次生代谢产物在不同生物界的生物中很少共享。因此，在亲缘关系较远的生物体之间，防御代谢物生物合成途径的进化并没有被广泛研究。噻唑并吲哚类化合物存在于拟南芥中，作为植物抗毒素卡马西平，以及链霉菌菌株中，该菌株合成一种具有肿瘤抑制作用的衍生物，命名为 BE-10988。卡马西平来源于半胱氨酸和色氨酸，色氨酸转化为吲哚-3-乙二肟，然后脱水生成吲哚-3-乙腈。BE-10988 的代谢起源通过反生物合成 NMR 分析和用直接前体进行的掺入研究来确定。与卡马西平一样，它也来源于色氨酸和半胱氨酸。然而，由于 BE-10988 是通过吲哚-3-丙酮酸合成的，而不是通过吲哚-3-乙二肟，因此进化出了独立的色氨酸修饰机制。
