Skip to main content
SpringerLink
Log in

Agarotetrol as an index for evaluating agarwood in crude drug products

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

Abstract

Agarotetrol in agarwood has been detected in water extracts or decoctions from medical use agarwood but the detection of agarotetrol has not been reported from other crude drugs. Agarwood generates the sedative benzylacetone upon heating. In this study, crude drug products containing many kinds of crude drugs in addition to agarwood were analyzed. Agarotetrol was detected and quantified, demonstrating that agarotetrol is useful for the quality evaluation of agarwood in complex prescriptions. High-performance liquid chromatography conditions to clearly separate agarotetrol from crude drug products were established and agarotetrol from Kampo decoctions was detected and quantified. Agarotetrol was also detected even from small crude drug product samples. These results suggest that agarotetrol is a useful component for the quality evaluation of agarwood in crude drug products.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

References

  1. Hashim YZH-Y, Kerr PG, Abbas P, Salleh HM (2016) Aquilaria spp. (agarwood) as source of health beneficial compounds: a review of traditional use, phytochemistry and pharmacology. J Ethnopharmacol 189:331–360

    Article  CAS  Google Scholar 

  2. Huo H-X, Gu Y-F, Sun H et al (2017) Anti-inflammatory 2-(2-phenylethyl) chromone derivatives from Chinese agarwood. Fitoterapia 18:49–55

    Article  Google Scholar 

  3. Li W, Cai C-H, Dong W-H et al (2014) 2-(2-Phenylethyl) chromone derivatives from Chinese agarwood induced by artificial holing. Fitoterapia 98:117–123

    Article  CAS  Google Scholar 

  4. Kumeta Y, Ito M (2010) Characterization of δ-guaiene synthases from cultured cells of Aquilaria, responsible for the formation of the sesquiterpenes in agarwood. Plant Physiol 154:1998–2007

    Article  CAS  Google Scholar 

  5. Naef R (2011) The volatile and semi-volatile constituents of agarwood, the infected heartwood of Aquilaria species: a review. Flavour Frag J 26:73–87

    Article  CAS  Google Scholar 

  6. Ishihara M, Tsuneya T, Uneyama K (1993) Components of the agarwood smoke on heating. J Essent Oil Res 5:419–423

    Article  CAS  Google Scholar 

  7. Takamatsu S, Ito M (2018) Agarotetrol: a source compound for low molecular weight aromatic compounds from agarwood heating. J Nat Med 72:537–541

    Article  CAS  Google Scholar 

  8. Dougnon G, Ito M (2020) Sedative effects of the essential oil from the leaves of Lantana camara occurring in the Republic of Benin via inhalation in mice. J Nat Med 74:159–169

    Article  CAS  Google Scholar 

  9. Miyoshi T, Ito M, Kitayama T et al (2013) Sedative effects of inhaled benzylacetone and structural features contributing to its activity. Biol Pharm Bull 36:1474–1481

    Article  CAS  Google Scholar 

  10. 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  CAS  Google Scholar 

  11. Takamatsu S, Ito M (2020) Agarotetrol in agarwood: its use in evaluation of agarwood quality. J Nat Med 74:98–105

    Article  CAS  Google Scholar 

  12. Yagura T, Shibayama N, Ito M et al (2005) Three novel diepoxy tetrahydrochromones from agarwood artificially produced by intentional wounding. Tetrahedron lett 46:4395–4398

    Article  CAS  Google Scholar 

  13. Goda H., Hakamatsuka T (2014) 日本生薬関係規格集2014. Jiho, Inc.

  14. Ito M (2009) 生薬学へのいざない-生薬学は今日の医療にどう役立つのか-. Kyoto Hirokawa Publishing Inc. p14-p15.

  15. The Japanese standards for non-Pharmacopoeial crude drugs 2018, The Ministry of Health Labor and Welfare, Japan

  16. Annual Report of the Secretariat 2004, Convention on International Trade in Endangered Species of Wild Fauna and Flora

  17. Akter S, Islam MT, Zulkefeli M, Khan SI (2013) Agarwood production-a multidisciplinary field to be explored in Bangladesh. Int J Pharm Life Sci 2:22–32

    Article  Google Scholar 

  18. Talucder MSA, Haque MM, Saha D (2016) Development of agar (Aquilaria malaccensis) cultivation, propagation technique and its potentiality as agroforestry component in bangladesh: a review. A Rev J Sylhet Agric Univ 3:149–157

    Google Scholar 

  19. Yan T, Yang S, Chen Y et al (2019) Chemical profiles of cultivated agarwood induced by different techniques. Molecules 24:1990

    Article  CAS  Google Scholar 

  20. Takamatsu S, Ito M (2021) Factors affecting 2-(2-phenylethyl) chromones in artificial agarwood. J Nat Med 1–10

  21. Shimada Y, Konishi T, Kiyosawa S, Nishi M, Miyahara K, Kawasaki T (1986) Studies on the Agarwood (Jinko). IV. Structures of 2-(2-Phenylethyl)chromone derivatives agarotetrol and isoagarotetrol. Chem Pharm Bull 34(7):2766–2773

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to Mitsuboshi Pharmaceutical Co., Ltd., Nakajimasyoyaku Co., Ltd., and Zenel Pharmaceutical Co., Ltd. for their assistance.

Author information

Authors and Affiliations

  1. Graduate School of Agriculture, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime, 790-8566, Japan

    Sakura Takamatsu

  2. National Institute of Health Sciences, 3-25-26 Tonomachi, Kawasaki-ku, Kawasaki City, Kanagawa, 210-9501, Japan

    Michiho Ito

Authors
  1. Sakura Takamatsu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Michiho Ito
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Michiho Ito.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 138 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Takamatsu, S., Ito, M. Agarotetrol as an index for evaluating agarwood in crude drug products. J Nat Med 76, 857–864 (2022). https://doi.org/10.1007/s11418-022-01632-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11418-022-01632-3

Keywords

Search

Navigation