Molecular Markers for Pyrethrin Autoxidation in Stored Pyrethrum Crop: Analysis and Structure Determination.
Pyrethrum is a natural insecticide extracted from Tanacetum cinerariifolium. Six esters, the pyrethrins, are responsible for the extract's insecticidal activity. The oxidative degradation of pyrethrins through contact with aerial oxygen is a potential cause of pyrethrin losses during pyrethrum manufacture. Described here is the first investigation of the autoxidation chemistry of the six pyrethrin esters isolated from pyrethrum. It was found that pyrethrins I and II, the major pyrethrin esters present in pyrethrum, undergo autoxidation more readily than the minor pyrethrin esters, the jasmolins and cinerins. Chromatographic analysis of pyrethrin I and II autoxidation mixtures showed some correlation with a similar analysis performed on extracts from T. cinerariifolium crop, which had been stored for 12 weeks without added antioxidants. Two pyrethrin II autoxidation products were isolated, characterized, and shown to be present in extracts of stored T. cinerariifolium crop, confirming that autoxidation of pyrethrin esters does occur during crop storage.
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.
Jamie A
JA
Freemont
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.
Stuart W
SW
Littler
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.
Oliver E
OE
Hutt
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.|Institut de Recherche de Chimie Paris, CNRS - Chimie ParisTech , 11 rue Pierre et Marie Curie, 75005 Paris, France.
Stephanie
S
Mauger
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.
Adam G
AG
Meyer
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.|School of Chemical and Physical Sciences, Flinders University , Adelaide, South Australia 5042, Australia.
David A
DA
Winkler
Botanical Resources Australia , 44-46 Industrial Drive, Ulverstone, Tasmania 7315, Australia.
Maurice G
MG
Kerr
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.
John H
JH
Ryan
Botanical Resources Australia , 44-46 Industrial Drive, Ulverstone, Tasmania 7315, Australia.
Helen F
HF
Cole
CSIRO Manufacturing, Bag 10, Clayton South, Victoria 3169, Australia.|School of Chemical and Physical Sciences, Flinders University , Adelaide, South Australia 5042, Australia.
Peter J
PJ
Duggan
D011723:Chrysanthemum cinerariifolium / Q000737:chemistry*; D018556:Crops, Agricultural / Q000737:chemistry; D007306:Insecticides / Q000737:chemistry* / Q000302:isolation & purification; D010084:Oxidation-Reduction; D011722:Pyrethrins / Q000737:chemistry* / Q000302:isolation & purification
D007306:Insecticides; D011722:Pyrethrins
Tanacetum cinerariifolium; autoxidation; degradation; pyrethrins; pyrethrum