Abstract
Two new tirucallane triterpenoids, aquilacallanes A–B (1–2), together with 15 known compounds (3–17) were isolated from the leaves of Aquilaria sinensis. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses. All compounds were evaluated for their cytotoxic activity against five human cancer cell lines. The known compounds, ursolic acid (7) and 5,7,4′-trimethoxyflavone (14), exhibited weak cytotoxic activity against some cells.
Similar content being viewed by others
References
Arai, Y., M. Hirohara, and H. Ageta. 1989. Fern constituents: three new skeletal triterpenoid hydrocarbons isolated from Polypoldiodes niponica. Tetrahedron Letters 30: 7209–7212.
Dai, H.F., J. Liu, Z. Han, Y.B. Zeng, H. Wang, and W.L. Mei. 2010. Two new 2-(2-phenylethyl)chromones from Chinese eaglewood. Journal of Asian Natural Products Research 12: 134–137.
Feng, J., X.W. Yang, and R.F. Wang. 2011. Bio-assay guided isolation and identification of α-glucosidase inhibitors from the leaves of Aquilaria sinensis. Phytochemistry 72: 242–247.
Gadgoli, C., and S.H. Mishra. 2007. Antihepatotoxic activity of 5-Hydroxy 3,4′,6,7-tetramethoxy flavone from Achillea millefolium. Pharmacology 1: 391–399.
Gao, Y.H., J.M. Liu, H.X. Lu, and Z.X. Wei. 2012. Two new 2-(2-phenylethyl)chromen-4-ones from Aquilaria sinensis (Lour.) Gilg. Helvetica Chimica Acta 95: 951–954.
Hashimoto, K., S. Nakahara, T. Inoue, Y. Sumida, M. Takahashi, and Y. Masada. 1985. A new chromone from agarwood and pyrolysis products of chromone derivatives. Chemical and Pharmaceutical Bulletin 33: 5088–5091.
Jain, T.C., and S.C. Bhattacharyya. 1959. Structure, stereochemistry and absolute configuration of agarol, a new sesquiterpene alcohol from agarwood oil. Tetrahedron Letters 1: 13–17.
Kizu, H., and T. Tomimori. 1982. Studies on the constituents of Clematis species. V. On the saponins of the root of Clematis chinensis Osbeck. Chemical and Pharmaceutical Bulletin 30: 3340–3346.
Maheshwari, M.L., T.C. Jain, R.B. Bates, and S.C. Bhattacharyya. 1963a. Terpenoids-XLI: structure and absolute configuration of α-agarofuran, β-agarofuran and dihydroagarofuran. Tetrahedron 19: 1079–1090.
Maheshwari, M.L., K.R. Varma, and S.C. Bhattacharyya. 1963b. Terpenoids-XLVII: structure and absolute configuration of norketoagarofuran, 4-hydroxydihydroagarofuran, 3,4-dihydroxydihydroagarofuran and conversion of β-agarofuran to α-agarofuran. Tetrahedron 19: 1519–1525.
Mishra, M., Y.N. Shukla, and S. Kumar. 2000. Euphane triterpenoid and lipid constituents from Butea monosperma. Phytochemistry 54: 835–838.
Mosmann, T. 1983. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. Journal of Immunological Methods 65: 55–63.
Nakanishi, T., E. Yamagata, K. Yoneda, and I. Miura. 1981. Jinkohol, a prezizane sesquiterpene alcohol from agarwood. Phytochemistry 20: 1597–1599.
Nakanishi, T., E. Yamagata, K. Yoneda, T. Nagashima, I. Kawasaki, T. Yoshida, H. Mori, and I. Miura. 1984. Three fragrant sesquiterpenes of agarwood. Phytochemistry 23: 2066–2067.
Nie, C., Y. Song, D. Chen, P. Xue, P. Tu, K. Wang, and J. Chen. 2009. Studies on chemical constituents of leaves of Aquilaria sinensis. Zhongguo Zhongyao Zazhi 34: 858–860.
Qi, J., J.J. Lu, J.H. Liu, and B.Y. Yu. 2009. Flavonoid and a rare benzophenone glycoside from the leaves of Aquilaria sinensis. Chemical and Pharmaceutical Bulletin 57: 134–137.
Rios, M.Y., and A.B. Aguilar-Guadarrama. 2002. Terpenes and a new bishomotriterpene from Esenbeckia stephani. Biochemical Systematics and Ecology 30: 1006–1008.
Schun, Y., G.A. Cordell, P.J. Cox, and R.A. Howie. 1986. Studies on thymelaeaceae. Part 4. Wallenone, a C32 triterpenoid from the leaves of Gyrinops walla. Phytochemistry 25: 753–755.
Seki, H., K. Ohyama, S. Sawai, M. Mizutani, T. Ohnishi, H. Sudo, H. Akashi, T. Aoki, K. Saito, and T. Muranake. 2008. Licorice β-amyrin 11-oxidase, a cytochrome P450 with a key role in the biosynthesis of the triterpene sweetener glycyrrhizin. Proceedings of the National Academy of Sciences 105: 14204–14209.
Shimada, Y., T. Tominaga, T. Konishi, and S. Kiyosawa. 1982. Studies on the agarwood (Jinko). I. Structures of 2-(2-phenylethyl) chromone derivatives. Chemical and Pharmaceutical Bulletin 30: 3791–3795.
Tundis, R., B. Deguin, F. Menichini, and F. Tillequin. 2002. Iridoids from Putoria calabrica. Biochemical Systematics and Ecology 30: 689–691.
Varma, K.R., M.L. Maheshwari, and S.C. Bhattacharyya. 1965. Terpenoids-LXII: the constitution of agarospirol, a sesquiterpenoid with a new skeleton. Tetrahedron 21: 115–138.
Wang, H.G., M.H. Zhou, J.J. Lu, and B.Y. Yu. 2008. Antitumor constituents from the leaves of Aquilaria sinensis (Lour.) Gilg. Linchan Huaxue Yu Gongye 28: 1–5.
Wang, L.Y., N.L. Wang, X.S. Yao, S. Miyata, and S. Kitanaka. 2003. Euphane and tirucallane triterpenes from the roots of Euphorbia kansui and their in vitro effects on the cell division of xenopus. Journal of Natural Products 66: 630–633.
Severi, J.A., Z.P. Lima, H. Kushima, A.R. Brito, L.C. Santos, W. Vileqas, and C.A. Hiruma-Lima. 2009. Polyphenols with antiulcerogenic action from aqueous decoction of mango Leaves (Mangifera indica L.). Molecules 14: 1098–1110.
Sutthanut, K., B. Sripanidkulchai, C. Yenjai, and M. Jay. 2007. Simultaneous identification and quantitation of 11 flavonoid constituents in Kaempferia parviflora by gas chromatography. Journal of Chromatography A 1143: 227–233.
Yagura, T., N. Shibayama, M. Ito, F. Kiuchi, and G. Honda. 2005. Three novel diepoxy tetrahydrochromones from agarwood artificially produced by intentional wounding. Tetrahedron Letters 46: 4395–4398.
Yang, L., L. Qiao, D. Xie, Y. Yuan, N. Chen, J. Dai, and S.X. Guo. 2012. 2-(2-Phenylethyl)chromones from Chinese eaglewood. Phytochemistry 76: 92–97.
Yim, S.H., H.J. Kim, and I.S. Lee. 2003. A polyacetylene and flavonoids from Cirsium rhinoceros. Archives of Pharmacal Research 26: 128–131.
Zhuo, M., H. Lu, B. Ren, W. Li, Z. Zhao, and H. Zhang. 2008. Chemical constituents of Gynura bicolor. Zhongcaoyao 39: 30–32.
Acknowledgments
This work was financially supported by the National Basic Research Program of China (973 Program Nos. 2011CB915503 and 2009CB522303), the National Natural Science Foundation of China (No. U0932602), and the State Key Laboratory of Phytochemistry and Plant Resources in West China (No. P2010-ZZ05).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Cheng, J.T., Han, Y.Q., He, J. et al. Two new tirucallane triterpenoids from the leaves of Aquilaria sinensis . Arch. Pharm. Res. 36, 1084–1089 (2013). https://doi.org/10.1007/s12272-013-0088-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-013-0088-4