Isolation and absolute configuration determination of aliphatic sulfates as the Daphnia kairomones inducing morphological defense of a phytoplankton.
2,6-Dimethylheptyl sulfate (1) and 6-methyloctyl sulfate (3) 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 stereochemistry at C2 of 1 was determined by (1)H-NMR analysis of the (R)-MTPA ester of alcohol 2. The absolute configuration at C6 of 3 was determined by Ohrui's method applied to alcohol 4.
Yasumoto
Ko
K
Graduate School of Pharmaceutical Sciences, Tokushima University, Japan.
Nishigami
Akinori
A
Kasai
Fumie
F
Kusumi
Takenori
T
Ooi
Takashi
T
D017738:Alkanesulfonic Acids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D000818:Animals; D003621:Daphnia / Q000737:chemistry*; D006536:Heptanes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D044444:Scenedesmus / Q000187:drug effects* / Q000648:ultrastructure; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D013431:Sulfates / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*; D013463:Sulfuric Acid Esters / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology*
C420912:2,6-dimethylheptyl sulfate; C509490:6-methyloctyl sulfate; D017738:Alkanesulfonic Acids; D006536:Heptanes; D007202:Indicators and Reagents; D013431:Sulfates; D013463:Sulfuric Acid Esters