Advertisement

Archives of Pharmacal Research

, Volume 31, Issue 8, pp 965–969 | Cite as

A new cytotoxic prenylated dihydrobenzofuran derivative and other chemical constituents from the rhizomes of Atractylodes lancea DC

  • Jin-ao Duan
  • Liuying Wang
  • Shihui Qian
  • Shulan Su
  • Yuping Tang
Research Articles Drug Discovery

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.

Key words

Atractylodes lancea Asteraceae Constituent Atractylenolide Dihydrobenzofuran Cytotoxicity 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Bai, Y., Lou, W., and Liu, Y., Studies on the chemical constituents of Vernonia volkameriifolia (Wall.) DC. Zhongcaoyao, 16, 530–532 (1985).Google Scholar
  2. Bohlmann, F, Baruah, R. N., King, R. M., and Robinson, H., Alicyclic diterpenes from Cronquistianthus bishopii. Planta Med., 51, 167–168 (1985).PubMedCrossRefGoogle Scholar
  3. Crichton, E. G., and Waterman, P. G., Dihydromammea C/OB: a new coumarin from the seed of Mammea Africana. Phytochmistry, 17, 1783–1786 (1978).CrossRefGoogle Scholar
  4. 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).PubMedGoogle Scholar
  5. 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).PubMedGoogle Scholar
  6. Jares, E. A., Tettamanzi, M. C., and Pomilio, A. B., Sitosterol 3-O-β-D-glucuronopyranoside from Senecio bonariensis. Phytochemistry, 29, 340–341 (1990).CrossRefGoogle Scholar
  7. 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).CrossRefGoogle Scholar
  8. 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).PubMedCrossRefGoogle Scholar
  9. 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).PubMedGoogle Scholar
  10. 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).PubMedCrossRefGoogle Scholar
  11. 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).Google Scholar
  12. 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).Google Scholar
  13. 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).CrossRefGoogle Scholar
  14. 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).Google Scholar
  15. 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).CrossRefGoogle Scholar
  16. 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).PubMedCrossRefGoogle Scholar
  17. 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).PubMedCrossRefGoogle Scholar
  18. 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).Google Scholar
  19. Zhao, Q., Hao, X. J., Chen, Y. Z., and Zou, C., Sesquterpenoids from Hedychium yunnanense. Yunnan Zhiwu Yanjiu, 17, 201–203 (1995).Google Scholar
  20. 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).Google Scholar

Copyright information

© The Pharmaceutical Society of Korea 2008

Authors and Affiliations

  • Jin-ao Duan
    • 1
  • Liuying Wang
    • 2
    • 3
  • Shihui Qian
    • 4
  • Shulan Su
    • 1
    • 2
  • Yuping Tang
    • 1
  1. 1.Jiangsu Key Laboratory for TCM formulae ResearchNanjing University of Chinese MedicineNanjingChina
  2. 2.Pharmaceutical collegeJiangsu UniversityZhenjiangChina
  3. 3.Nanjing Hailing R&D for Chinese Traditional MedicineNanjingChina
  4. 4.Jiangsu Institute of Traditional Chinese MedicineNanjingChina

Personalised recommendations