Isolation and absolute configuration determination of aliphatic sulfates as the Daphnia kairomones inducing morphological defense of a phytoplankton-part 2

Ko Yasumoto; Akinori Nishigami; Hiroaki Aoi; Chise Tsuchihashi; Fumie Kasai; Takenori Kusumi; Takashi Ooi

doi:10.1248/cpb.56.129

Isolation and absolute configuration determination of aliphatic sulfates as the Daphnia kairomones inducing morphological defense of a phytoplankton-part 2

Chem Pharm Bull (Tokyo). 2008 Jan;56(1):129-32. doi: 10.1248/cpb.56.129.

Authors

Ko Yasumoto¹, Akinori Nishigami, Hiroaki Aoi, Chise Tsuchihashi, Fumie Kasai, Takenori Kusumi, Takashi Ooi

Affiliation

¹ Institute of Health Biosciences, The University of Tokushima Graduate School, Tokushima, Japan.

PMID: 18175993
DOI: 10.1248/cpb.56.129

Abstract

4,8-Dimethylnonyl sulfate (1) and 3-methyl-4E-decenyl sulfate (2) were isolated from Daphnia pulex as the Daphnia kairomones that induced morphological defense of a freshwater phytoplankton Scenedesmus gutwinskii var. heterospina (NIES-802). The absolute configuration at C4 of 1 was determined by Ohrui's method applied to alcohol 3. The absolute stereochemistry at C3 of 2 was determined by (1)H-NMR analysis of the (R)-1NMA ester of alcohol 11.

MeSH terms

Animals
Daphnia / chemistry*
Fresh Water
Magnetic Resonance Spectroscopy
Molecular Structure
Pheromones / chemistry
Pheromones / isolation & purification*
Pheromones / pharmacology*
Phytoplankton / drug effects*
Sulfuric Acid Esters / chemistry*
Sulfuric Acid Esters / isolation & purification*
Sulfuric Acid Esters / pharmacology

Substances

3-methyl-4E-decenyl sulfate
4,8-dimethylnonyl sulfate
Pheromones
Sulfuric Acid Esters