Misplaced Pages

Actinidine

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.

Not to be confused with Actinidin, Actinide, or Actinium.
Actinidine
Structural formula of actinidine
Space-filling
Names
Preferred IUPAC name (7S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopentapyridine
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 81308
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: 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/s1Key: ZHQQRIUYLMXDPP-ZETCQYMHBZ
SMILES
  • C(CC1)C2=C1C(C)=CN=C2
  • n1cc(c2c(c1)(CC2)C)C
Properties
Chemical formula C10H13N
Molar mass 147.221 g·mol
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. It is one of several compounds that may be extracted from the valerian (Valeriana officinalis) root and silver vine (Actinidia polygama), as well as several types of insects in the larval and imaginal stages. 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.

Biosynthesis

A potential biosynthesis of actinidine from L-citronellal is shown below.

References

  1. Sakan T (1959). "On the Structure of Actinidine and Matatabilactone, the Effective Components of Actinidia polygama". Bulletin of the Chemical Society of Japan. 32 (3): 315–316. doi:10.1246/bcsj.32.315.
  2. Tsutsui M, Tsutsui EA (1959). "Diterpenoids". Chemical Reviews. 59 (6): 1031–1075. 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". Ann. Pharm. Fr. (in French). 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. Lichman BR, Godden GT, Hamilton JP, Palmer L, Kamileen MO, Zhao D, Vaillancourt B, Wood JC, Sun M, Kinser TJ, Henry LK (2020-05-01). "The evolutionary origins of the cat attractant nepetalactone in catnip". Science Advances. 6 (20): eaba0721. Bibcode:2020SciA....6..721L. doi:10.1126/sciadv.aba0721. ISSN 2375-2548. PMC 7220310. PMID 32426505.
  6. Wu IH, Liu HH, Chen YY, Tsai CL, Yu YC, Hsiao CY, Yeh WB (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.
  7. Funayama S, Cordell GA, eds. (2015). "14: Alkaloids Derived from Terpenoids". Alkaloids. Academic Press. pp. 233–255.
Categories: