Nepetalactone
Note: I bet you didn’t know that.
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Summary by ChatGPT - the original is too long-winded: Nepetalactone
Nepetalactone refers to a group of stereoisomeric iridoids, primarily produced by Nepeta cataria (catnip) and other Nepeta species, where it acts as an insect repellent and is involved in defense against herbivores. It is also a sex pheromone in aphids. Nepetalactone is famous for inducing behavioral responses in two-thirds of adult cats and other felines, such as lions and jaguars, although not all felines are equally sensitive to it. The compound triggers similar reactions in domestic cats as morphine by stimulating endorphin release, but does not lead to opioid withdrawal symptoms.
Structurally, nepetalactone has three chiral centers and exists as eight possible stereoisomers. These isomers can be categorized based on the cis and trans orientations at the ring fusion and the placement of the methyl group. The (cis,trans)-isomer is the most common variant and is produced via biosynthetic pathways involving geranyl pyrophosphate, which is modified by enzymes into different nepetalactone isomers.
In felines, nepetalactone elicits behaviors such as rolling, licking, and rubbing against the source plant, likely due to its insect-repelling properties. The compound may help protect these animals by driving them to apply the repellent through grooming, particularly when they are exposed to biting insects while hunting.
References:
Lichman BR, et al. (2020). "The evolutionary origins of the cat attractant nepetalactone in catnip." Science Advances, 6(20), eaba0721. doi:10.1126/sciadv.aba0721.
Espín-Iturbe LT, et al. (2017). "Active and passive responses to catnip (Nepeta cataria) are affected by age, sex, and early gonadectomy in male and female cats." Behavioural Processes, 142, 110–115. doi:10.1016/j.beproc.2017.06.008.
McElvain SM, Bright RD, Johnson PR. (1941). "The constituents of the volatile oil of catnip. I. Nepetalic acid, nepetalactone, and related compounds." Journal of the American Chemical Society, 63(6), 1558–1563. doi:10.1021/ja01851a019.
Zimmermann N, et al. (2012). "Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix." Beilstein Journal of Organic Chemistry, 8(1), 1246–1255. doi:10.3762/bjoc.8.140.
Uenoyama R, et al. (2021). "The characteristic response of domestic cats to plant iridoids allows them to gain chemical defense against mosquitoes." Science Advances, 7(4), eabd9135. doi:10.1126/sciadv.abd9135.
Haynes WM, et al. (2014). "Physical constants of organic compounds." CRC Handbook of Chemistry and Physics (95th ed.), pp. 408–409.
Sherden NH, et al. (2018). "Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry." Phytochemistry, 145, 48–56. doi:10.1016/j.phytochem.2017.10.004.
Bol S, et al. (2017). "Responsiveness of cats (Felidae) to silver vine (Actinidia polygama), Tatarian honeysuckle (Lonicera tatarica), valerian (Valeriana officinalis), and catnip (Nepeta cataria)." BMC Veterinary Research, 13(1), 70. doi:10.1186/s12917-017-0987-6.
Döring TF. (2014). "How aphids find their host plants, and how they don’t." Annals of Applied Biology, 165(1), 3–26. doi:10.1111/aab.12142.
Flores FG, et al. (2012). "An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis." Nature, 492(7427), 138–142. doi:10.1038/nature11692.
Hill JO, et al. (1976). "Species-characteristic responses to catnip by undomesticated felids." Journal of Chemical Ecology, 2(2), 239–253. doi:10.1007/BF00987747.
Resende LS, et al. (2011). "Influence of cinnamon and catnip on the stereotypical pacing of oncilla cats (Leopardus tigrinus) in captivity." Journal of Applied Animal Welfare Science, 14(3), 247–254. doi:10.1080/10888705.2011.576981.