Identification of behaviorally significant volatile compounds in the anal gland of the rabbit,Oryctolagus cuniculus

Goodrich, B. S.; Hesterman, E. R.; Murray, Keith E.; Mykytowycz, R.; Stanley, G.; Sugowdz, G.

doi:10.1007/bf00988922

Cited by 30 publications

(15 citation statements)

References 19 publications

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“…Benbernou et al 2007;Saito et al 2009;Nara et al 2011), including human Or1a1 and Or2w1 (Geithe et al 2017a,b). Z4-11Al is produced in the anal gland of male wild rabbits and may be involved in territorial marking; the aldehyde was found to affect the heart rate when perceived by other male rabbits (Goodrich et al 1978). The positional isomer (E)-2-undecenal is a bovid body odor (Gikonyo et al 2002) and olfactory sensory neurons of ticks tuned to aldehydes afford indirect evidence for aldehyes as vertebrate signals (Steullet and Guerin 1994).…”

Section: Discussionmentioning

confidence: 99%

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The Scent of the Fly

et al. 2018

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Abstract(Z)-4-undecenal (Z4-11Al) is the volatile pheromone produced by females of the vinegar fly Drosophila melanogaster. Female flies emit Z4-11Al for species-specific communication and mate-finding. A sensory panel finds that synthetic Z4-11Al has a characteristic flavour, which can be perceived even at the small amounts produced by a single female fly. Since only females produce Z4-11Al, and not males, we can reliably distinguish between single D. melanogaster males and females, according to their scent. Females release Z4-11Al at 2.4 ng/h and we readily sense 1 ng synthetic Z4-11Al in a glass of wine (0.03 nmol/L), while a tenfold concentration is perceived as a loud off-flavour. This corroborates the observation that a glass of wine is spoilt by a single D. melanogaster fly falling into it, which we here show is caused by Z4-11Al. The biological role of Z4-11Al or structurally related aldehydes in humans and the basis for this semiochemical convergence remains yet unclear.

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Section: Discussionmentioning

confidence: 99%

“…Cullere et al 2007;Perez-Cacho and Rouseff 2008;Shi et al 2013;Varlet et al 2006;Yang et al 2008). Moreover, Z4-11Al is an anal gland volatile in the rabbit (Goodrich et al 1978).…”

Section: Introductionmentioning

confidence: 99%

The Scent of the Fly

et al. 2018

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“…Unsaturated aldehydes are part of human skin emanations (Duffy et al 2018) and serve as cues for detecting the presence of humans (Li et al 2014). Intriguingly, milk from humans and rabbits contains (E)-2-decenal and (Z)-2-undecenal, respectively, and Z4-11Al has been found in rabbit anal glands, accelerating heartbeat upon perception (Goodrich et al 1978, Schaal et al 2003, Duffy et al 2018. Taken together, Z4-11Al is found in human food, it might even be produced by ourselves and could manifest food, social context, or both.…”

Section: Occurrence Of Z4-11al In Human Odour Scenesmentioning

confidence: 99%

The human odorant receptor OR10A6 is tuned to the pheromone of the commensal fruit fly Drosophila melanogaster

Frey

Kwadha

Wallin

et al. 2020

Preprint

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BackgroundAll living things speak chemical. The challenge is to discover the vocabulary, the volatile odorant chemicals that enable communication across phylogenies and to translate them to physiological, behavioural and ecological function. Olfactory receptors (ORs) interface animals with airborne odorants. Expression of single ORs in human embryonic kidney cells (HEK-293) makes it possible to interrogate ORs with synthetic chemicals and to identify cognate ligands that convey olfactory information.ResultsThe cosmopolitan strain of the vinegar fly Drosophila melanogaster has accompanied the human expansion out of Africa, more than ten thousand years ago. These flies are strictly anthropophilic and depend on human resources and housing for survival, particularly in colder climate zones. Curiously, humans sense the scent of a single fly, and more precisely the female pheromone (Z)-4 undecenal (Z4-11Al), at 10 ng/mL (0.06 µmol/L). A screening of all functional human ORs in a HEK-293 assay provides an explanation for this astounding sensitivity, as it shows that OR10A6, one of the most highly expressed human ORs, is specifically tuned to Z4-11Al. Chemical analysis of fly effluvia confirms that cosmopolitan D. melanogaster females release Z4-11Al, while females of an African fly strain from Zimbabwe release a 1:3-blend of Z4-11Al and (Z)-4 nonenal (Z4-9Al). Interestingly, a blend of Z4-9Al and Z4-11Al produces a different aroma than the the single compounds, which is why we readily differentiate cosmopolitan and Zimbabwe flies by nose.ConclusionThat we sensitively and specifically perceive the fly pheromone Z4-11Al suggests that it is a component of human odour scenes. This may have afforded a sensory drive during adaptation of commensal flies to human habitats and selected for a role of Z4-11Al in fly aggregation and premating communication. Screening ORs for key ligands leads to the discovery of messenger chemicals that enable chemical communication among and betwen vertebrate and invertebrate animals.

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“…1 H NMR: δ 0.87 (t, 3, J ) 7.2 Hz), 1.21-1.35 (m, 8), 1.41 (qt, 2, J ) 7.2 Hz), 1.57 (qt, 2, J ) 7.2 Hz), 2.00 (qd, 2, J ) 6.6 Hz), 2.05 (qd, 2, J ) 7.2 Hz), 3.64 (t, 2, J ) 6.6 Hz), 5.30-5.40 (m, 2). 13 C NMR 14.2, 22.8, 26.1, 27.1, 27.4, 29.2, 29.9, 32.0, 32.5, 62.9, 129.5, 130.5. MS m/z (%): 166 (M + -H2O, 3), 110 (11), 95 (33), 82 (43), 81 (45), 67 (87), 55 (80), 41 (100).…”

Section: Z-dodecenol (4) (A)mentioning

confidence: 99%

Improved Synthesis of (3E,7Z)-3,7-Tetradecadienyl Acetate, the Major Sex Pheromone Constituent of the Potato Pest Symmetrischema tangolias (Gyen)

Ragoussis

Perdikaris

Karamolegkos

et al. 2008

J. Agric. Food Chem.

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An efficient six-step synthesis of (3E,7Z)-3,7-tetradecadienyl acetate, the major component of the sex pheromone of the potato pest Symmetrischema tangolias (Gyen), is described, starting from the commercially available dihydropyran. The stereoselective formation of the 7Z double bond is accomplished by a Wittig reaction, while the 3E double bond is formed by a modified Knoevenagel condensation. The overall yield of the synthesis is 28%, giving the final product in high stereochemical purity (95%). The simplicity and the low cost of the herein reported synthesis suggest the potential practical use of the above pheromone in integrated management programs, for this serious insect pest.

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Identification of behaviorally significant volatile compounds in the anal gland of the rabbit,Oryctolagus cuniculus

Cited by 30 publications

References 19 publications

The Scent of the Fly

The Scent of the Fly

The human odorant receptor OR10A6 is tuned to the pheromone of the commensal fruit fly Drosophila melanogaster

Improved Synthesis of (3E,7Z)-3,7-Tetradecadienyl Acetate, the Major Sex Pheromone Constituent of the Potato Pest Symmetrischema tangolias (Gyen)

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