The Sex Pheromones of Two Pine Sawfly Species, Gilpinia frutetorum and Gilpinia socia: Chemical Identification, Synthesis and Biological Activity

• 3,7-Dimethylpentadecan-2-ol and 3-methylpentadecan-2-ol were identified in female whole body extracts from the two pine sawfly species Gilpinia frutetorum and Gilpinia socia. This is the first observation of 3-methylpentadecan-2-ol in extracts of a female pine sawfly species. Synthetic and highly pure stereoisomers of 3,7-dimethylpentadecan-2-ol and 3-methylpentadecan-2-ol were used to verify that the (2S,3R,7R)isomer of 3,7-dimethylpentadecan-2-ol and (2S,3R)-3-methylpentadecan-2-ol were present in the extracts. The four stereoisomers of 3-methylpentadecan-2-ol and their biologically active esters were produced via chemoenzymatic methods and the synthesis is described in detail. Male G. socia antennae responded strongly in EAG recordings to the (2S,3R)-isomer of the acetate and propionate of 3-methylpentadecan-2-ol. Male antennae of both G. frutetorum and G. socia also responded to the (2S,3R,7R)- and (2S,3R,7S)-acetates of 3,7-dimethylpentadecan-2-ol.

Ämnesord

NATURVETENSKAP  -- Biologiska vetenskaper -- Biokemi och molekylärbiologi (hsv//swe)

NATURAL SCIENCES  -- Biological Sciences -- Biochemistry and Molecular Biology (hsv//eng)

MEDICIN OCH HÄLSOVETENSKAP  -- Medicinska grundvetenskaper -- Farmaceutisk vetenskap (hsv//swe)

MEDICAL AND HEALTH SCIENCES  -- Basic Medicine -- Pharmaceutical Sciences (hsv//eng)

Nyckelord

Kemi

Chemistry

Biologi

Biology

Gilpinia frutetorum

Sex Pheromone

Gilpinia socia

Gilpinia frutetorum; Gilpinia socia; Sex Pheromone

FARMACI

PHARMACY

Cell- och molekylärbiologi

Cell and molecular biology

diprionidae

hymenoptera

components

acetate

lipase

attractants

analogs

Publikations- och innehållstyp

art (ämneskategori)

ref (ämneskategori)