Actinidine

Actinidine
Names
	IUPAC name (S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine
Identifiers
CAS Number	524-03-8 ;
3D model (JSmol)	Interactive image; Interactive image;
Beilstein Reference	81308
ChEBI	CHEBI:2443 ;
ChemSpider	61533 ;
KEGG	C09910 ;
PubChem CID	68231;
CompTox Dashboard (EPA)	DTXSID70894115 ;
	InChI InChI=1S/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1 Key: ZHQQRIUYLMXDPP-ZETCQYMHSA-N ; InChI=1/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1 Key: ZHQQRIUYLMXDPP-ZETCQYMHBZ;
	SMILES C[C@@H](CC1)C2=C1C(C)=CN=C2; n1cc(c2c(c1)[C@H](CC2)C)C;
Properties
Chemical formula	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

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.

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

Sakan, Takeo; Bulletin of the Chemical Society of Japan, 1959, V32, P315-16.
Tsutsui, Minoru; Tsutsui, Ethel Ashworth (1959). "Diterpenoids". Chemical Reviews. 59 (6): 1031–75. doi:10.1021/cr50030a003.
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.
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.
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.
Chapter 14 - Alkaloids Derived from Terpenoids, Editors: Shinji Funayama, Geoffrey A. Cordell, Alkaloids, Academic Press, 2015, pp. 233-55

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[1] Sakan, Takeo; Bulletin of the Chemical Society of Japan, 1959, V32, P315-16.

[Tsutsui1959-2] 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.

[Wu2020-5] 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