Actinidine Explained

Actinidine is an iridoid produced in nature by a wide variety of plants and animals. It was the first cyclopentanoid monoterpene alkaloid to be discovered.[1] It is one of several compounds that may be extracted from the valerian (Valeriana officinalis) root[2] and silver vine (Actinidia polygama), as well as several types of insects in the larval and imaginal stages.[3] Actinidine is a cat attractant, with effects like those of nepetalactone, the active compound found in catnip.[4]

Certain species of stick insects, including Megacrania batesii and Megacrania tsudai, possess a chemical defense mechanism which involves the secretion of an actinidine-containing substance from the prothoracic glands, when threatened by a predator.[5]

Biosynthesis

A potential biosynthesis of actinidine from -citronellal is shown below.[6]

References

  1. Tsutsui. Minoru. Tsutsui. Ethel Ashworth. Diterpenoids. Chemical Reviews. 59. 6. 1031–1075. 1959. 10.1021/cr50030a003.
  2. Janot MM, Guilhem J, Contz O, Venera G, Cionga E . 1979. Contribution to the study of valerian alcaloids (Valeriana officinalis L.): actinidine and naphthyridylmethylketone, a new alkaloid . French. Ann. Pharm. Fr.. 37. 9–10. 413–20. 547813.
  3. Weibel DB, Oldham NJ, Feld B, Glombitza G, Dettner K, Boland W. 2001. Iridoid biosynthesis in staphylinid rove beetles (Coleoptera: Staphylinidae, Philonthinae). Insect Biochemistry and Molecular Biology. 31. 6–7. 583–591. 10.1016/s0965-1748(00)00163-6. 11267897.
  4. Lichman. Benjamin R.. Godden. Grant T.. Hamilton. John P.. Palmer. Lira. Kamileen. Mohamed O.. Zhao. Dongyan. Vaillancourt. Brieanne. Wood. Joshua C.. Sun. Miao. Kinser. Taliesin J.. Henry. Laura K.. 2020-05-01. The evolutionary origins of the cat attractant nepetalactone in catnip. Science Advances. en. 6. 20. eaba0721. 10.1126/sciadv.aba0721. 32426505. 7220310. 2020SciA....6..721L . 2375-2548. free.
  5. Life cycles, phenology and genetic structure of endangered Megacrania tsudai Shiraki (Phasmatodea: Phasmatidae): Male individuals from a geographic parthenogenesis species. Entomological Science. 23. 2. 183–192. 2020. 10.1111/ens.12410. Wu. I-Hsin. Liu. Hsui-Huei. Chen. Yu-Yen. Tsai. Cheng-Lung. Yu. Yi-Ching. Hsiao. Chung-Yi. Yeh. Wen-Bin. 216322536.
  6. Book: 14: Alkaloids Derived from Terpenoids . Shinji . Funayama . Geoffrey A. . Cordell . Alkaloids . Academic Press . 2015 . 233–255.

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