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

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.