Agarotetrol in agarwood: its use in evaluation of agarwood quality

  • Sakura Takamatsu
  • Michiho ItoEmail author
Original Paper


Agarwood, which is used as medicine and incense, contains sesquiterpenes and chromones. Agarotetrol is a chromone derivative found in high concentrations in the water-extract fraction of agarwood and thus may be present in pharmaceutical products made from decoctions of agarwood. Agarotetrol has been reported to be present at the early stages of cell death in calli. We therefore examined the presence of agarotetrol in medical- and incense-grade agarwood, in agarwood-source plants lacking resin deposits, and in artificially made agarwood. Agarotetrol appeared as a large peak in the HPLC chromatograms of all samples of medical-grade and artificially made agarwood, and in most incense-grade agarwood samples. In contrast, agarwood samples lacking resin deposits did not contain agarotetrol. These results show that agarotetrol is characteristic of resin formation. Agarotetrol was also detected in decoctions of agarwood. A newly developed TLC method for the detection of agarotetrol in agarwood is described.


Agarwood Chromone derivatives Quality evaluation Agarotetrol 



This work was partly supported by the Kobayashi International Scholarship Foundation.


  1. 1.
    The Japanese standards for non-pharmacopoeial crude drugs 2018, The Ministry of Hearth Labour and Welfare, JapanGoogle Scholar
  2. 2.
    Neaf R (2011) The volatile and semi-volatile constituents of agarwood, the infected heartwood of Aquilaria species: a review. Flavor Fragr J 26:73–89CrossRefGoogle Scholar
  3. 3.
    Yagura T, Shibayama N, Ito M, Kiuchi F, Honda G (2005) Three novel diepoxy tetrahydrochromones from agarwood artificially produced by intentional wounding. Tetrahedron Lett 46:4395–4398CrossRefGoogle Scholar
  4. 4.
    Kishida K, Ito M (2009) Components of agarwood oils and their effects on spontaneous motor activity of mice. Shoyakugaku Zasshi 63(2):39–45Google Scholar
  5. 5.
    Ishihara M, Tsuneya T (1993) Compounds of the agarwood smoke on heating. J Essent Oil Res 5:419–423CrossRefGoogle Scholar
  6. 6.
    Takamatsu S, Ito M (2018) Agarotetrol: a source compound for low molecular weight aromatic compounds from agarwood heating. J Nat Med 72:537–541CrossRefGoogle Scholar
  7. 7.
    Okudera Y, Ito M (2009) Production of agarwood fragrant constituents in Aquilaria calli and cell suspension cultures. Plant Biotechnol 26:307–315CrossRefGoogle Scholar
  8. 8.
    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):2766–2773CrossRefGoogle Scholar
  9. 9.
    Kanbe T, Ikuta-Shimadzu N, Hirano T (2005) Difference in the constituents of green tea leaves by storage conditions. Memoirs Beppu Univ 46:91–100Google Scholar
  10. 10.
    Sato Y (2015) Food preparation and off-flavor. J Cook Sci Jpn 48(5):333–341Google Scholar
  11. 11.
    Yagura T, Ito M, Kiuchi F, Honda G, Shimada Y (2003) Four new 2-(2-phenylethyl) chromone derivatives from withered wood of Aquilaria sinensis. Chem Pharm Bull 51(5):560–564CrossRefGoogle Scholar
  12. 12.
    Yang DL, Mei WL, Zeng YB, Guo KZ, Zhao YX, Wang H, Zuo WJ, Dong WH, Wang QH, Dai HF (2013) 2-(2-phenylethyl) chromone derivatives in chinese agarwood “Qi-Nan” from Aquilaria sinensis. Planta Med 79:1329–1334CrossRefGoogle Scholar
  13. 13.
    Yang JL, Dong WH, Kong FD, Liao G, Wang J, Li W, Mei WL, Dai HF (2016) Characterization and analysis of 2-(2-Phenylethyl)-chromone derivatives from agarwood (Aquilaria crassna) by artificial holding for different times. Molecules 21:911CrossRefGoogle Scholar
  14. 14.
    Shao H, Mei WL, Dong WH, Gai CJ, Li W, Zhu GP, Dai HF (2016) 2-(2-phenylethyl) chromone derivatives of agarwood originating from Gyrinops salicifolia. Molecules 21:1313CrossRefGoogle Scholar
  15. 15.
    Subasinghe SMCUP, Heharacterisation DS (2015) Characterisation of agarwood type resin of Gyrinops walla Gaertn growing in selected populations in Sri Lanka. Ind Crops Prod 69:76–79CrossRefGoogle Scholar
  16. 16.
    Shu YQ, Meng LH, Li DL, Chuan HZ, Lan JH, Hui ZZ (2005) Production of 2-(2-phenylethyl) chromones in cell suspension cultures of Aquilaria sinensis. Plant Cell Tissue Organ Cult 83:217–221CrossRefGoogle Scholar
  17. 17.
    Shimada Y, Tominaga T, Kiyosawa S (1986) Studies on the agarwood (jinko). IV correlation between the grading of agarwood on the market and the chromone derivatives. Yakugaku Zasshi 106(5):391–397CrossRefGoogle Scholar
  18. 18.
    Yagura T (2004) Doctoral dissertation, Kyoto UniversityGoogle Scholar
  19. 19.
    Japanese pharmacopoeia, seventeenth edition, The Ministry of Hearth Labour and Welfare, JapanGoogle Scholar
  20. 20.
    Konishi T, Okutani Y, Iwagoe K, Kiyosawa S, Shimada Y (1989) Studies of the agarwood “Jinko” (IX)1 quantitative analysis of 2-(2-phenylethyl) chromone derivatives (supplement). Shoyakugaku Zasshi 43(1):1–6Google Scholar
  21. 21.
    Annual report of the secretariat 2004, Convention on international trade in endangered species of wild fauna and floraGoogle Scholar
  22. 22.
    Huang JQ, Liao YC, Chen HJ, Zhang Z (2017) Chemical solution is an efficient method to induce the formation of 2-(2-phenylethyl) chromone derivatives in Aquilaria sinensis. Phytochem Lett 19:64–70CrossRefGoogle Scholar

Copyright information

© The Japanese Society of Pharmacognosy 2019

Authors and Affiliations

  1. 1.Graduate School of Pharmaceutical SciencesKyoto UniversityKyotoJapan

Personalised recommendations