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J Insect Physiol

Title:		"N-(3-methylbutyl)butanamide: A novel amide in the venom of female social wasps, Vespula vulgaris"
Author(s):		El-Sayed AM; Brown RL; Bunn B;
Address:		"The New Zealand Institute for Plant and Food Research Limited, Gerald Street, 7608 Lincoln, New Zealand. Electronic address: ashraf.el-sayed@plantandfood.co.nz. Manaaki Whenua Landcare Research, 54 Gerald Street, 7608 Lincoln, New Zealand. The New Zealand Institute for Plant and Food Research Limited, Batchelar Road, 4474 Palmerston North, New Zealand"
Journal Title:		J Insect Physiol
Year:		2021
Volume:		20210927
Issue:
Page Number:		104311 -
DOI:		10.1016/j.jinsphys.2021.104311
ISSN/ISBN:		1879-1611 (Electronic) 0022-1910 (Linking)
Abstract:		"In New Zealand's ancient Fuscospora spp. or beech forests, two invasive Vespula social wasps Vespula vulgaris (L.) and Vespula germanica (F.) have become significant problems, adversely affecting native birds and invertebrate biodiversity. The nature of chemical communication in these two species is poorly understood, and this work was undertaken to identify the behaviourally active compounds in the venom of the common wasp, Vespula vulgaris (L.). Venom was removed from the stings of both workers and females and analyzed by coupled gas chromatography/electroantennographic detection (GC/EAD) and gas chromatography/mass spectrometry (GC/MS). Two compounds were present in the venom that consistently elicited EAD responses from the antennae of males and workers. Mass spectrometry analysis and syntheses of candidate structures revealed the structures to be N-(3-methylbutyl)acetamide (MBA) and N-(3-methylbutyl)butanamide (MBB). Gyne venom contains significantly larger amounts of MBA and MBB than worker venom. When these two compounds were tested in the field individually or as binary blends in combination with the known food odour (honeydew volatiles), only N-(3-methylbutyl)butanamide or blends containing this compound showed a strong repellent effect on workers to honeydew volatiles at all doses tested. This is the first report of the occurrence of N-(3-methylbutyl)butanamide in nature and the third amide to be identified in the venom of any social wasp. In addition, this work is the first to report the chemical analysis of the venom of V. vulgaris gyne. The repellency effect observed in this study of the venom compound suggests that our definition and understanding of the function of the alarm pheromone need to be reassessed"
Keywords:		Amides/*chemistry Animals Female Introduced Species Male New Zealand Odorants Pheromones/chemistry Venoms/*chemistry *Wasps/chemistry/classification Alarm pheromone N-(3-methylbutyl)acetamide N-(3-methylbutyl)butanamide Social wasps Venom Vespula vulgaris;
Notes:		"MedlineEl-Sayed, Ashraf M Brown, Robert L Bunn, Barry eng Research Support, Non-U.S. Gov't England 2021/10/01 J Insect Physiol. 2021 Nov-Dec; 135:104311. doi: 10.1016/j.jinsphys.2021.104311. Epub 2021 Sep 27"