Actinidine

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.[2] It is one of several compounds that may be extracted from the valerian (Valeriana officinalis) root[3] and silver vine (Actinidia polygama), as well as several types of insects in the larval and imaginal stages.[4] Actinidine is a cat attractant, with effects like those of nepetalactone, the active compound found in catnip.

Not to be confused with Actinidin, Actinide, or Actinium.
Actinidine
Names
IUPAC name
(S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine
Identifiers
3D model (JSmol)
81308
ChEBI
ChemSpider
KEGG
Properties
C10H13N
Molar mass 147.221 g·mol−1
Melting point < 25 °C (77 °F; 298 K)
Boiling point 100 to 103 °C (212 to 217 °F; 373 to 376 K) at 9 mmHg[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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 L-citronellal is shown below.[6]

References
  1. Sakan, Takeo; Bulletin of the Chemical Society of Japan, 1959, V32, P315-16.
  2. Tsutsui, Minoru; Tsutsui, Ethel Ashworth (1959). "Diterpenoids". Chemical Reviews. 59 (6): 1031–75. doi:10.1021/cr50030a003.
  3. 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 (article in French)". Ann. Pharm. Fr. 37 (9–10): 413–20. PMID 547813.
  4. 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. doi:10.1016/s0965-1748(00)00163-6. PMID 11267897.
  5. Wu, I‐Hsin; Liu, Hsui‐Huei; Chen, Yu‐Yen; Tsai, Cheng‐Lung; Yu, Yi‐Ching; Hsiao, Chung‐Yi; Yeh, Wen‐Bin (2020). "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. doi:10.1111/ens.12410. S2CID 216322536.
  6. Chapter 14 - Alkaloids Derived from Terpenoids, Editors: Shinji Funayama, Geoffrey A. Cordell, Alkaloids, Academic Press, 2015, pp. 233-55
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