Journal of Natural Medicines

, Volume 67, Issue 4, pp 833–837 | Cite as

The sedative effect of inhaled terpinolene in mice and its structure–activity relationships

Note

Abstract

Terpinolene is a cyclic monoterpene compound found in some Labiatae herbs. In our previous study, we evaluated the sedative effect of inhaled essential oils of Microtoena patchoulii leaves in mice and isolated terpinolene as an active ingredient. We investigated the structure–activity relationships of terpinolene to identify the structural part essential to its sedative effect. Comparison of terpinolene analog activities showed that a double bond in the side-chain or pi bonds in the six-membered ring play important roles in the sedative effect. In another experiment using olfactory impaired mice, we further revealed that inhaled terpinolene exerted the effect after nasal absorption into the body.

Keywords

Sedative effect Inhalation Terpinolene Structure–activity relationship 

References

  1. 1.
    Senpuku M, Nonaka K, Ito M, Honda G (2007) Chemical composition of the essential oil of Microtoena patchoulii [(CB Clarke ex JD Hooker) CY Wu et Hsuan]. J Essent Oil Res 19:336–337CrossRefGoogle Scholar
  2. 2.
    Ito K, Ito M (2011) Sedative effects of vapor inhalation of the essential oil of Microtoena patchoulii and its related compounds. J Nat Med 65:336–343PubMedCrossRefGoogle Scholar
  3. 3.
    Takemoto H, Ito M, Shiraki T, Yagura T, Honda G (2008) Sedative effects of vapor inhalation of agarwood oil and spikenard extract and identification of their active components. J Nat Med 62:41–46PubMedCrossRefGoogle Scholar
  4. 4.
    Takemoto H, Yagura T, Ito M (2009) Evaluation of volatile components from spikenard: valerena-4,7(11)-diene is a highly active sedative compound. J Nat Med 63:380–385PubMedCrossRefGoogle Scholar
  5. 5.
    Kimura Y, Furukawa M, Kamide M, Sakumoto M, Miwa T, Umeda R (1989) Experimental study on the effect of the topical application of steroids on olfactory disturbance in mice. Nihon Jibiinkoka Gakkai Kaiho 92:1869–1875PubMedCrossRefGoogle Scholar
  6. 6.
    Chuah MI, Tennent R, Jacobs I (1995) Response of olfactory Schwann cells to intranasal zinc sulfate irrigation. J Neurosci Res 42:470–478PubMedCrossRefGoogle Scholar
  7. 7.
    Revial G, Jabin I, Pfau M (2000) Enantioselective synthesis of (+)-α-vetivone through the Michael reaction of chiral imines. Tetrahedron Asymmetry 11:4975–4983CrossRefGoogle Scholar
  8. 8.
    Wallenstein S, Zucker CL, Fleiss JL (1980) Some statistical methods useful in circulation research. Circ Res 47:1–9PubMedCrossRefGoogle Scholar
  9. 9.
    Mathews DF (1972) Response patterns of single neurons in the tortoise olfactory epithelium and olfactory bulb. J Gen Physiol 60:166–180PubMedCrossRefGoogle Scholar
  10. 10.
    Imamura K, Mataga N, Mori K (1992) Coding of odor molecules by mitral/tufted cells in rabbit olfactory bulb. I. Aliphatic compounds. J Neurophysiol 68:1986–2002PubMedGoogle Scholar
  11. 11.
    Johnson BA, Arguello S, Leon M (2007) Odorants with multiple oxygen-containing functional groups and other odorants with high water solubility preferentially activate posterior olfactory bulb glomeruli. J Comp Neurol 502:468–482PubMedCrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan 2013

Authors and Affiliations

  1. 1.Department of PharmacognosyGraduate School of Pharmaceutical Science, Kyoto UniversityKyotoJapan

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