Abstract
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.
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References
The Japanese standards for non-pharmacopoeial crude drugs 2018, The Ministry of Hearth Labour and Welfare, Japan
Neaf R (2011) The volatile and semi-volatile constituents of agarwood, the infected heartwood of Aquilaria species: a review. Flavor Fragr J 26:73–89
Yagura T, Shibayama N, Ito M, Kiuchi F, Honda G (2005) Three novel diepoxy tetrahydrochromones from agarwood artificially produced by intentional wounding. Tetrahedron Lett 46:4395–4398
Kishida K, Ito M (2009) Components of agarwood oils and their effects on spontaneous motor activity of mice. Shoyakugaku Zasshi 63(2):39–45
Ishihara M, Tsuneya T (1993) Compounds of the agarwood smoke on heating. J Essent Oil Res 5:419–423
Takamatsu S, Ito M (2018) Agarotetrol: a source compound for low molecular weight aromatic compounds from agarwood heating. J Nat Med 72:537–541
Okudera Y, Ito M (2009) Production of agarwood fragrant constituents in Aquilaria calli and cell suspension cultures. Plant Biotechnol 26:307–315
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
Kanbe T, Ikuta-Shimadzu N, Hirano T (2005) Difference in the constituents of green tea leaves by storage conditions. Memoirs Beppu Univ 46:91–100
Sato Y (2015) Food preparation and off-flavor. J Cook Sci Jpn 48(5):333–341
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):560–564
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 79:1329–1334
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 21:911
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 21:1313
Subasinghe SMCUP, Heharacterisation DS (2015) Characterisation of agarwood type resin of Gyrinops walla Gaertn growing in selected populations in Sri Lanka. Ind Crops Prod 69:76–79
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 83:217–221
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):391–397
Yagura T (2004) Doctoral dissertation, Kyoto University
Japanese pharmacopoeia, seventeenth edition, The Ministry of Hearth Labour and Welfare, Japan
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):1–6
Annual report of the secretariat 2004, Convention on international trade in endangered species of wild fauna and flora
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 19:64–70
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This work was partly supported by the Kobayashi International Scholarship Foundation.
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Takamatsu, S., Ito, M. Agarotetrol in agarwood: its use in evaluation of agarwood quality. J Nat Med 74, 98–105 (2020). https://doi.org/10.1007/s11418-019-01349-w
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DOI: https://doi.org/10.1007/s11418-019-01349-w