Schachtschabel Doreen, Schimek Christine, Wöstemeyer Johannes, Boland Wilhelm
Abteilung Bioorganische Chemie, Max-Planck-Institut für chemische Okologie, Hans-Knöll-Strasse 8, D-07745 Jena, Germany.
Phytochemistry. 2005 Jun;66(11):1358-65. doi: 10.1016/j.phytochem.2005.04.022.
In the course of their sexual interactions, zygomycete fungi communicate via an elaborate series of carotene-derived compounds, namely trisporic acid and its biosynthetic progenitors. A novel building-block strategy allowed the systematic generation of structurally modified trisporoids along with putative early biosynthetic precursors for physiological tests. The impact of discrete structural elements was documented by the ability of individual compounds to induce sexually committed hyphae in Mucor mucedo. The activity screening contributed to establish general structure-function relationships for trisporoid action. Most crucial for activity were the dimension of the longer side chain, the polarity of functional groups at C(4) and C(13), and the number of conjugated double bonds in the side chain. The presence of an oxygen substituent at the cyclohexene ring is not essential for function. The overall biological activity apparently results from the combination of the various structural elements.
在接合菌纲真菌的有性相互作用过程中，它们通过一系列复杂的类胡萝卜素衍生化合物进行交流，即三孢酸及其生物合成前体。一种新颖的构建模块策略使得能够系统地生成结构修饰的三孢酸类化合物以及用于生理测试的假定早期生物合成前体。通过单个化合物在总状毛霉中诱导性成熟菌丝的能力，记录了离散结构元件的影响。活性筛选有助于建立三孢酸类化合物作用的一般结构 - 功能关系。对于活性而言，最重要的是较长侧链的尺寸、C(4)和C(13)处官能团的极性以及侧链中共轭双键的数量。环己烯环上氧取代基的存在对功能并非必不可少。总体生物活性显然是由各种结构元件的组合产生的。
