Stereochemical course of pheromone biosynthesis in the arctiid moth,Creatonotos transiens

1984 ◽  
Vol 40 (7) ◽  
pp. 713-714 ◽  
Author(s):  
T. W. Bell ◽  
M. Boppré ◽  
D. Schneider ◽  
J. Meinwald
Keyword(s):  
Pheromone Biosynthesis ◽  
Arctiid Moth ◽  
Creatonotos Transiens

Organ Specific Storage of Dietary Pyrrolizidine Alkaloids in the Arctiid Moth Creatonotos transiens

1990 ◽  
Vol 45 (1-2) ◽  
pp. 115-120 ◽  
Author(s):  
A. Egelhaaf ◽  
K. Cölln ◽  
B. Schmitz ◽  
M. Buck ◽  
M. Wink ◽  
...  
Keyword(s):  
Pyrrolizidine Alkaloids ◽  
Developmental Stages ◽  
Pyrrolizidine Alkaloid ◽  
Chemical Defence ◽  
Pheromone Biosynthesis ◽  
Gas Liquid Chromatography ◽  
Specific Storage ◽  
Arctiid Moth ◽  
Organ Specific ◽  
Creatonotos Transiens

Abstract Larvae of the arctiid moth Creatonotos transiens obtained each 5 mg of heliotrine, a pyrrolizidine alkaloid, via an artificial diet. 7 S-H eliotrine is converted into its enantiomer, 7 R1-heliotrine, and some minor metabolites, such as callimorphine. 7 S- and 7 R-heliotrine are present in the insect predominantly (more than 97%) as their N-oxides. The distribution of heliotrine in the organs and tissues of larvae, prepupae, pupae and imagines was analyzed by capillary gas-liquid chromatography. A large proportion of the alkaloid is stored in the integument of all developmental stages, where it probably serves as a chemical defence compound against predators. Female imagines had transferred substantial amounts of heliotrine to their ovaries and subsequently to their eggs; males partly directed it to their pheromone biosynthesis.

Time-Course of Pyrrolizidine Alkaloid Processing in the Alkaloid Exploiting Arctiid Moth, Creatonotos transiens

1990 ◽  
Vol 45 (7-8) ◽  
pp. 881-894 ◽  
Author(s):  
Eva von Nickisch-Rosenegk ◽  
Dietrich Schneider ◽  
Michael Wink
Keyword(s):  
Laboratory Experiments ◽  
Time Course ◽  
Pyrrolizidine Alkaloids ◽  
Pyrrolizidine Alkaloid ◽  
Hydroxyl Group ◽  
Short Term ◽  
Arctiid Moth ◽  
Total Alkaloids ◽  
Creatonotos Transiens

Abstract The processing of dietary pyrrolizidine alkaloids by larvae and adults of the arctiid moth Creatonotos transiens was studied in time-course experiments: In larvae, pyrrolizidine alkaloid uptake is quickly followed by the transformation of the alkaloids into their N-oxides. Further- more, if 7 S-heliotrine is applied, a stereochemical inversion of the hydroxyl group at C 7 to 7 R-heliotrine can be observed within 48 h of feeding. The rate of this biotransformation is substantially higher in males which use the 7 R-form later as a precursor for the biosynthesis of 7 R-hydroxydanaidal, a pheromone. The resorbed pyrrolizidine alkaloids are deposited in the integument within 48 h, where they remain stored during the larval, pupal and partly also the imaginal stages. Virtually no alkaloids are lost during ecdysis. Some pyrrolizidine alkaloids can be recovered from the meconium which is released at eclosion by the imagines especially when disturbed. In the adults pyrrolizidine alkaloids are processed in different ways by the two sexes: In females, about 50-80% of total alkaloids are transferred from the integument to the ovaries and the eggs within 2 - 3 days after eclosion. If females mate with alkaloid-rich males they additionally receive with the spermatophore up to 290 jig pyrrolizidine alkaloid, which are further translocated to the eggs. A biparental endowment of eggs with acquired defence alkaloids is thus achieved. In males, 30-50% of pyrrolizidine alkaloids remain in the integu- ment; about 10 - 30% are transferred to the scent organ, the corema, where they are converted into 7 R-hydroxydanaidal. Another part (about 40%) is passed to the spermatophore. In the laboratory experiments, the sizes of the coremata and their respective 7 R-hydroxydanaidal contents are strongly dependent on the availability of dietary pyrrolizidine alkaloids during L6 and especially L7 stages. In the L7 stage even short-term feeding (4-6 h) on Senecio jaco- haea is sufficient to induce large coremata.

Biosynthesis of Pyrrolidine Alkaloid-Derived Pheromones in the Arctiid Moth, Creatonotos transiens: Stereochemical Conversion of Heliotrine

1988 ◽  
Vol 43 (9-10) ◽  
pp. 737-741 ◽  
Author(s):  
M. Wink ◽  
D. Schneider ◽  
L. Witte
Keyword(s):  
Developmental Stages ◽  
Pyrrolizidine Alkaloid ◽  
Major Metabolite ◽  
Arctiid Moth ◽  
Capillary Glc ◽  
Creatonotos Transiens ◽  
C Nmr

Abstract In larvae and later developmental stages of Creatonotos transiens, which had been reared on the pyrrolizidine alkaloid 7S-heliotrine, a new major metabolite was detected by capillary GLC. The structure of this metabolite was determined by GLC-MS (EI, CI-MS) and 13C NMR to be 7Rheliotrine and 7R-heliotrine-N-oxide. 7R-Heliotrine is likely to be the direct precursor for the pheromone R( - )-hydroxydanaidal.

scholarly journals Iridoid Sex Pheromone Biosynthesis in Aphids Mimics Iridoid‐Producing Plants

2021 ◽  
Author(s):  
Suzanne J. Partridge ◽  
David M. Withall ◽  
John C. Caulfield ◽  
John A. Pickett ◽  
Robert A. Stockman ◽  
...  
Keyword(s):  
Sex Pheromone ◽  
Pheromone Biosynthesis ◽  
Sex Pheromone Biosynthesis

scholarly journals Latest Developments in Insect Sex Pheromone Research and Its Application in Agricultural Pest Management

Insects ◽  
2021 ◽  
Vol 12 (6) ◽  
pp. 484
Author(s):  
Syed Arif Hussain Rizvi ◽  
Justin George ◽  
Gadi V. P. Reddy ◽  
Xinnian Zeng ◽  
Angel Guerrero
Keyword(s):  
Sex Pheromone ◽  
Pest Management ◽  
Interdisciplinary Approach ◽  
Pheromone Biosynthesis ◽  
Insect Pheromones ◽  
Agricultural Pest ◽  
Practical Applications ◽  
The Past ◽  
Significant Research ◽  
Recent Developments

Since the first identification of the silkworm moth sex pheromone in 1959, significant research has been reported on identifying and unravelling the sex pheromone mechanisms of hundreds of insect species. In the past two decades, the number of research studies on new insect pheromones, pheromone biosynthesis, mode of action, peripheral olfactory and neural mechanisms, and their practical applications in Integrated Pest Management has increased dramatically. An interdisciplinary approach that uses the advances and new techniques in analytical chemistry, chemical ecology, neurophysiology, genetics, and evolutionary and molecular biology has helped us to better understand the pheromone perception mechanisms and its practical application in agricultural pest management. In this review, we present the most recent developments in pheromone research and its application in the past two decades.

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