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The mating hormones α1 and α2 induce sexual reproduction of the phytopathogenic genus Phytophthora. To demonstrate the structural elements responsible to hormonal activity, 17 derivatives of α1 and α2 were synthesized and their hormonal activity (oospore-inducing activity) was evaluated. The terminal ester derivatives of α1 (diacetate and dibenzoate) retained the hormonal activity, whereas a dicarbamate derivative completely suppressed the activity. Even monocarbamates showed weak activities; among them the 1-O-carbamate was less active than 16-O-carbamate, suggesting that the 1-OH group is a little more important than 16-OH. Dihydro, dehydro, and demethyl derivatives exhibited the minimum level of activity. Surviving activity of 15-epi-α1 suggested a less importance of this stereochemistry. Contrary to α1, not only the terminal diacetate derivative but also monoacetates of α2 exhibited no or little activity. Among the monoacetates, 1-O-acetyl-α2 exhibited little yet relatively better activity than the others. No activity was observed for mono- and dicarbamoyl derivatives of α2. Dihydro α2 with the saturated double bond lost most of the activity. These findings suggest that both the mating hormones α1 and α2 require most of the functional (hydroxyl, keto, and olefinic) groups they possess in their natural form for inducing the sexual reproduction of Phytophthora., (Copyright © 2011. Published by Elsevier Ltd.)

The heterothallic species of the agricultural pest Phytophthora use mating hormones α1 and α2 to regulate their sexual reproduction. Here we describe the absolute stereostructure of the second mating hormone α2 as defined by spectroscopic analysis and total synthesis. We have uncovered not only the interspecies universality of α hormones but also the pathway by which α2 is biosynthesized from phytol by A2-mating type strains and metabolized to α1 by A1 strains.

An important biological event in phytopathogens of the genus Phytophthora is sexual reproduction, which is conducted by two mating types, A1 and A2. A factor known as hormone alpha1 is secreted by the A1 mating type and induces the formation of sexual spores (oospores) in the A2 mating type. Here we describe the asymmetric synthesis and assignment of the absolute configuration of hormone alpha1 by oospore-inducing assays of the synthesized isomers.

Water molds of the genus Phytophthora include many plant pathogens responsible for epidemics such as potato blight and sudden oak death, causing global economic damages. Sexual reproduction is of biological importance in Phytophthora and has been believed to be stimulated by unknown endogenous factors named a hormones. We describe here the chemical characterization of a Phytophthora mating hormone, a1, which was obtained from approximately 2 tons of culture fluid of one mating type of a species and which induced sexual spores on the counter-mating type at a nanogram level.

Abstract: The stereochemistry of α1, the first identified mating hormone of the plant pathogen Phytophthora, has been unknown due to its acyclic flexible nature. Here, two stereogenic centers of α1 are determined to be (3RS,15R)-configuration by NMR analysis of the Mosher’s esters of α1 and a synthetic model compound. The information obtained here will be helpful for reducing the burden of the researchers who are trying to synthesize all the possible stereoisomers of α1 to elucidate its full stereochemistry. [Copyright &y& Elsevier]

Abstract: The first synthesis of a stereoisomeric mixture of hormone α1, the mating hormone of Phytophthora, was achieved, and the synthetic mixture was confirmed to be hormonally active. [Copyright &y& Elsevier]