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De Novo Asymmetric Synthesis and Biological Analysis of the Daumone Pheromones in Caenorhabditis elegans and in the Soybean Cyst Nematode Heterodera glycines.

ABSTRACT: The de novo asymmetric total syntheses of daumone 1, daumone 3 along with 5 new analogs are described. The key steps of our approach are: the diastereoselective palladium catalyzed glycosylation reaction; the Noyori reduction of 2-acetylfuran and an ynone, which introduce the absolute stereochemistry of the sugar and aglycon portion of daumone; and an Achmatowicz rearrangement, an epoxidation and a ring opening installing the remaining asymmetry of daumone. The synthetic daumones 1 and 3 as well as related analogs were evaluated for dauer activity in C. elegans and for effects on hatching of the related nematode H. glycines. This data provides additional structure activity relationships (SAR) that further inform the study of nematode signaling.

SUBMITTER: Guo H

PROVIDER: S-EPMC5809136 | biostudies-literature | 2016 May

REPOSITORIES: biostudies-literature

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Publications

De Novo Asymmetric Synthesis and Biological Analysis of the Daumone Pheromones in Caenorhabditis elegans and in the Soybean Cyst Nematode Heterodera glycines.

Guo Haibing H La Clair James J JJ Masler Edward P EP O'Doherty George G Xing Yalan Y

Tetrahedron 20160316 18

The de novo asymmetric total syntheses of daumone 1, daumone 3 along with 5 new analogs are described. The key steps of our approach are: the diastereoselective palladium catalyzed glycosylation reaction; the Noyori reduction of 2-acetylfuran and an ynone, which introduce the absolute stereochemistry of the sugar and aglycon portion of daumone; and an Achmatowicz rearrangement, an epoxidation and a ring opening installing the remaining asymmetry of daumone. The synthetic dau ...[more]

PMID: 29445247

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Project description:The soybean cyst nematode (SCN), Heterodera glycines, causes economically significant damage to soybeans (Glycine max) in many parts of the world. The cysts of this nematode can remain quiescent in soils for many years as a reservoir of infection for future crops. To investigate bacterial communities associated with SCN cysts, cysts were obtained from eight SCN-infested farms in southern Ontario, Canada, and analyzed by culture-dependent and -independent means. Confocal laser scanning microscopy observations of cyst contents revealed a microbial flora located on the cyst exterior, within a polymer plug region and within the cyst. Microscopic counts using 5-(4,6-dichlorotriazine-2-yl)aminofluorescein staining and in situ hybridization (EUB 338) indicated that the cysts contained (2.6 +/- 0.5) x 10(5) bacteria (mean +/- standard deviation) with various cellular morphologies. Filamentous fungi were also observed. Live-dead staining indicated that the majority of cyst bacteria were viable. The probe Nile red also bound to the interior polymer, indicating that it is lipid rich in nature. Bacterial community profiles determined by denaturing gradient gel electrophoresis analysis were simple in composition. Bands shared by all eight samples included the actinobacterium genera Actinomadura and STREPTOMYCES: A collection of 290 bacteria were obtained by plating macerated surface-sterilized cysts onto nutrient broth yeast extract agar or on actinomycete medium. These were clustered into groups of siblings by repetitive extragenic palindromic PCR fingerprinting, and representative isolates were tentatively identified on the basis of 16S rRNA gene sequence. Thirty phylotypes were detected, with the collection dominated by Lysobacter and Variovorax spp. This study has revealed the cysts of this important plant pathogen to be rich in a variety of bacteria, some of which could presumably play a role in the ecology of SCN or have potential as biocontrol agents.

Dataset Information

De Novo Asymmetric Synthesis and Biological Analysis of the Daumone Pheromones in Caenorhabditis elegans and in the Soybean Cyst Nematode Heterodera glycines.

Publications

De Novo Asymmetric Synthesis and Biological Analysis of the Daumone Pheromones in <i>Caenorhabditis elegans</i> and in the Soybean Cyst Nematode <i>Heterodera glycines</i>.

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