» Articles » PMID: 24420478

Macrocyclic Lactones and Isopentenyl Esters in the Dufour's Gland Secretion of Halictine Bees (Hymenoptera: Halictidae)

Overview
Journal J Chem Ecol
Publisher Springer
Date 2014 Jan 15
PMID 24420478
Citations 16
Authors
Affiliations
Soon will be listed here.
Abstract

The volatile components of the Dufour's gland secretion of female halictid bees have been examined in 18 Nearctic species belonging toAgapostemon, Augochlora, Augochlorella, Augochloropsis, Dialictus, Evylaeus, Halictus, andLasioglossum. Nine saturated and unsaturated macrocyclic lactones ranging from C18 to C26 have been identified. Four of these compounds, the saturated C26 and the unsaturated C20, C22, and C24 lactones, are new natural products reported for halictine bees. A series of eight esters containing branched C5-alkenols and fatty acids has been identified in several species. The cell linings and pollen ball inAugochlora pura pura contain the same major lactones as the Dufour's gland. A discussion of the significance of the Dufour's gland secretion for apoid systematics and its function in the Halictidae is presented.

Citing Articles

Cuticular and Dufour's Gland Chemistry Reflect Reproductive and Social State in the Facultatively Eusocial Sweat Bee Megalopta genalis (Hymenoptera: Halictidae).

Kingwell C, Boroczky K, Steitz I, Ayasse M, Wcislo W J Chem Ecol. 2021; 47(4-5):420-432.

PMID: 33682070 DOI: 10.1007/s10886-021-01262-1.


3-Acetoxy-fatty acid isoprenyl esters from androconia of the ithomiine butterfly .

Mann F, Szczerbowski D, de Silva L, McClure M, Elias M, Schulz S Beilstein J Org Chem. 2020; 16:2776-2787.

PMID: 33281981 PMC: 7684689. DOI: 10.3762/bjoc.16.228.


Queen Recognition Signals in Two Primitively Eusocial Halictid Bees: Evolutionary Conservation and Caste-Specific Perception.

Steitz I, Brandt K, Biefel F, Minat A, Ayasse M Insects. 2019; 10(12).

PMID: 31766459 PMC: 6955767. DOI: 10.3390/insects10120416.


Evolution of Caste-Specific Chemical Profiles in Halictid Bees.

Steitz I, Kingwell C, Paxton R, Ayasse M J Chem Ecol. 2018; 44(9):827-837.

PMID: 30014321 DOI: 10.1007/s10886-018-0991-8.


Solitary bees reduce investment in communication compared with their social relatives.

Wittwer B, Hefetz A, Simon T, Murphy L, Elgar M, Pierce N Proc Natl Acad Sci U S A. 2017; 114(25):6569-6574.

PMID: 28533385 PMC: 5488929. DOI: 10.1073/pnas.1620780114.


References
1.
Langenbeck U, Mohring H, Dieckmann K . Gas chromatography of alpha-keto acids as their O-trimethyl silylquinoxalinol derivatives. J Chromatogr. 1975; 115(1):65-70. DOI: 10.1016/s0021-9673(00)89016-0. View

2.
Hefetz A, Fales H, Batra S . Natural Polyesters: Dufour's Gland Macrocyclic Lactones Form Brood Cell Laminesters in Colletes Bees. Science. 1979; 204(4391):415-7. DOI: 10.1126/science.204.4391.415. View

3.
Norden B, Batra S, Fales H, Hefetz A, Shaw G . Anthophora Bees: Unusual Glycerides from Maternal Dufour's Glands Serve as Larval Food and Cell Lining. Science. 1980; 207(4435):1095-7. DOI: 10.1126/science.207.4435.1095. View

4.
Weseloh R . Dufour's gland: source of sex pheromone in a hymenopterous parasitoid. Science. 1976; 193(4254):695-7. DOI: 10.1126/science.948746. View