Abstract
A new prenylated dihydrobenzofuran derivative (1), was isolated from the rhizomes of Atractylodes lancea DC (Asteraceae), along with ten known compounds, including atractylenolide II (2), φ-taraxasteryl acetate (3), taraxerol acetate (4), β-sitosterol (5), stigmasterol (6), β-eudesmol (7), atractylenolide III (8), atractylenolide IV (9), daucosterol (10), and stigmasterol 3-O-β-D-glucopyranoside (11). The structure of the new compound (1) was elucidated as trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid by the combination of 1D, 2D NMR analysis and mass spectrometry, and it was the first reported 2,3-dihydrobenzofuran derivative having a carboxyl residue at C-5 and an isopentene moiety at C-7 contemporaneously. In addition, compound 1 exhibited significant cytotoxicity against cancer cell lines HCT-116 and MKN-45.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Bai, Y., Lou, W., and Liu, Y., Studies on the chemical constituents of Vernonia volkameriifolia (Wall.) DC. Zhongcaoyao, 16, 530–532 (1985).
Bohlmann, F, Baruah, R. N., King, R. M., and Robinson, H., Alicyclic diterpenes from Cronquistianthus bishopii. Planta Med., 51, 167–168 (1985).
Crichton, E. G., and Waterman, P. G., Dihydromammea C/OB: a new coumarin from the seed of Mammea Africana. Phytochmistry, 17, 1783–1786 (1978).
Friedrich, U., Siems, K., Solis, P. N., Gupta, M. P., and Jenett-Siems, K., New prenylated benzoic acid derivatives of Piper hispidum. Pharmazie, 60, 455–457 (2005).
Hikino, H., Hikino, Y., and Yosioka, I., Studies on the constituents of Atractylodes. IX. Structure and autoxidation of atractylon. Chem. Pharm. Bull., 12, 755–760 (1964).
Jares, E. A., Tettamanzi, M. C., and Pomilio, A. B., Sitosterol 3-O-β-D-glucuronopyranoside from Senecio bonariensis. Phytochemistry, 29, 340–341 (1990).
Kawasaki, C., Okuyama, T., and Shibata, S., Studies on coumarins of a Chinese drug “Qian-Hu”, Coumarins from “Zi-Hua Qian-Hu” (supplement). Planta Med., 50, 117–120 (1984).
Kitajima, J., Kamoshita, A., Ishikawa, T., Takano, A., Fukuda, T., Isoda, S., and Ida, Y., Glycosides of Atractylodes lancea. Chem. Pharm. Bull., 51, 673–678 (2003).
Kohjyouma, M., Nakajima, S., Namera, A., Shimizu, R., Mizukami, H., and Kohda, H., Random amplified polymorphic DNA analysis and variation of essential oil components of Atractylodes plants. Biol. Pharm. Bull., 20, 502–506 (1997).
Li, N., Deng, C., Li, Y., Ye, H., and Zhang, X., Gas chromatography — mass spectrometry following microwave distillation and headspace solid-phase microextraction for fast analysia of essential oil in dry traditional Chinese medicine. J. Chromatogr. A, 1133, 29–34 (2006).
Ling, Y., Bao, Y., Zhang, Y., Xiao, Y., and Zheng, J., Study on the chemical constituents of Taraxacum falciolbum Kitag. Zhongcaoyao, 31, 10–11 (2000).
Lou, F. C., Ma, Q. Y., and Du, F. L., Study on the chemical constituents of Lysimachia foenum-graecum Hance. Zhongguo Yaoke Daxue Xuebao, 20, 37–39 (1989).
Patra, A., Mukhopadhyay, A. K., and Mitra, A. K., Carbon-13 resonance assignments of some friedelanes and taraxasteranes. Org. Magn. Reson., 17, 166–168 (1981).
Qian, S. H., Wang, L. Y., Duan, J. A., and Feng, H. The research progress in chemical constituents and biological activities of Atractylodes lancea DC. Zhongguo Yesheng Zhiwu Ziyuan, 25, 8–11 (2006).
Sigstad, E. E., Catalan, C. A. N, Diaz, J. G., and Herz, W., Chromanones, benzofurans and other constituents from Ophryosporus lorentzii. Phytochemistry, 52, 1443–1445 (1996).
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107–1112 (1990).
Takeda, O., Miki, E., Terabayashi, S., Okada, M., Lu, Y., He, H. S., and He, S. A., A Comparative Study on Essential Oil Components of Wild and Cultivated Atractylodes lancea and A. chinensis. Planta Med., 62, 444–449 (1996).
Yang, N. Y., Qian, S. H., Duan, J. A., and Tian L. J., Studies on the chemical constituents of Eupatorium lindleyanum. Zhongguo Yaoke Daxue Xuebao, 34, 220–221 (2003).
Zhao, Q., Hao, X. J., Chen, Y. Z., and Zou, C., Sesquterpenoids from Hedychium yunnanense. Yunnan Zhiwu Yanjiu, 17, 201–203 (1995).
Zheng, W. P., Tang, Y. P., Lou, F. C., and Zhi, F., Studies on the constituents of Dendrobium chryseum Rolfe. Zhongguo Yaoke Daxue Xuebao, 31, 5–7 (2000).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Duan, Ja., Wang, L., Qian, S. et al. A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of Atractylodes lancea DC. Arch. Pharm. Res. 31, 965–969 (2008). https://doi.org/10.1007/s12272-001-1252-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-001-1252-z