Skip to main content
Log in

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

  • Note
  • Published:
Journal of Natural Medicines Aims and scope Submit manuscript

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3

References

  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 19:336–337

    Article  CAS  Google Scholar 

  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 65:336–343

    Article  PubMed  CAS  Google Scholar 

  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 62:41–46

    Article  PubMed  CAS  Google Scholar 

  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 63:380–385

    Article  PubMed  CAS  Google Scholar 

  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 92:1869–1875

    Article  PubMed  CAS  Google Scholar 

  6. Chuah MI, Tennent R, Jacobs I (1995) Response of olfactory Schwann cells to intranasal zinc sulfate irrigation. J Neurosci Res 42:470–478

    Article  PubMed  CAS  Google Scholar 

  7. Revial G, Jabin I, Pfau M (2000) Enantioselective synthesis of (+)-α-vetivone through the Michael reaction of chiral imines. Tetrahedron Asymmetry 11:4975–4983

    Article  CAS  Google Scholar 

  8. Wallenstein S, Zucker CL, Fleiss JL (1980) Some statistical methods useful in circulation research. Circ Res 47:1–9

    Article  PubMed  CAS  Google Scholar 

  9. Mathews DF (1972) Response patterns of single neurons in the tortoise olfactory epithelium and olfactory bulb. J Gen Physiol 60:166–180

    Article  PubMed  CAS  Google Scholar 

  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 68:1986–2002

    PubMed  CAS  Google Scholar 

  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 502:468–482

    Article  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Michiho Ito.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ito, K., Ito, M. The sedative effect of inhaled terpinolene in mice and its structure–activity relationships. J Nat Med 67, 833–837 (2013). https://doi.org/10.1007/s11418-012-0732-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-012-0732-1

Keywords

Navigation