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One new pregnane glycoside from the seeds of cultivated Brucea javanica

  • Jie-Qing Liu
  • Cui-Fang Wang
  • Xing-Yao Li
  • Jian-Chao Chen
  • Yan Li
  • Ming-Hua Qiu
Research Articles Drug Design and Discovery

Abstract

A new pregnane glycoside, named (20R)-O-(3)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-pregn-5-en-3β,20-diol (1), and seven known compounds, brusatol (2), bruceine B (3), bruceine D (4), yadanziolide A (5), bruceine E (6), yadanzioside G (7), and yadanzioside B (8), were isolated from the cultivated dry seeds of Brucea javanica. The structure of 1 was elucidated on the basis of 1D- and 2D-NMR spectroscopic analyses. Their inhibitory effects on tumor cells were also tested. Compound 1 was slightly active against HL-60, SMMC-7721, A-549, and MCF-7 tumor cells. Compounds 2 and 3 demonstrated significant inhibitory activities against all tested cells. These results indicate that cultivated B. javanica could replace the wild plant as an antitumor plant resource.

Key words

Brucea javanica Pregnane glycoside Antitumor activity Brusatol 

References

  1. Anderson, F., Judith, L., Gilardi, R., and George, C., Structure of bruceine B hydrate. Acta Crystallogr. C, 43, 801–803 (1987).CrossRefGoogle Scholar
  2. Christine, K., Tran, V. S., Trinh, T. T., Mai, V. T., and Gunter, A., (20R)-O-(3)-α-L-arabinopyranosyl-pregn-5-en-3β,20-diol from Brucea javanica. Phytochemistry, 38, 699–701 (1995).CrossRefGoogle Scholar
  3. Cooley, G., Kirk, D. N., Morgan, R. E., and Sá e Melo, M. L., Pyridine-induced shifts in the 1H nuclear magnetic resonance spectra of 20-hydroxypregnane derivatives. J. Chem. Soc. Perkin Trans. I, 1390–1395 (1977).CrossRefGoogle Scholar
  4. Harigaya, Y., Konda, Y., Iguchi, M., and Onda, M., Spectroscopic studies of brusatol. J. Nat. Prod., 52, 740–748 (1989).CrossRefGoogle Scholar
  5. Lau, S. T., Lin, Z. X., Zhao, M., and Leung, P. S., Brucea javanica fruit induces cytotoxicity and apoptosis in pancreatic adenocarcinoma cell lines. Phytother. Res., 22, 477–486 (2008).PubMedCrossRefGoogle Scholar
  6. Lee, K. H., Imakura, Y., Sumida, Y., Wu, R. Y., and Hall, I. H., Antitumor agents. 33. Isolation and structural elucidation of bruceoside-A and -B, novel antileukemic quassinoid glycosides, and brucein-D and -E from Brucea javanica. J. Org. Chem., 44, 2180–2185 (1979).CrossRefGoogle Scholar
  7. Li, X. and Tso, S. H., Studies on the anticancer principles in the seed of Yadanzi (Brucea javanica). III. Isolation and structural elucidation of bruceoside A, bruceoside B, bruceine E, and bruceine F. Zhong Cao Yao, 11, 530–532 (1980).Google Scholar
  8. Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol Methods, 65, 55–63 (1983).PubMedCrossRefGoogle Scholar
  9. Reed, L. J. and Muench, H., A simple method of estimating fifty percent endpoints. Am. J. Hyg., 27, 493–497 (1938).Google Scholar
  10. Saka, T., Yoshimura, S., Ishibashi, M., Tsuyuki, T., Takahashi, T., Honda, T., and Nakanishi, T., New quassinoid glycosides, yadanziosides A-H, from Brucea javanica. Chem. Pharm. Bull., 32, 4702–4705 (1984).Google Scholar
  11. Sharma, S. C. and Agarwal, V. K., Brucea javanica (Linn.) Merr.: a potent anticancer and antimalarial plant. A review. Indian J. Pharm. Sci., 55, 77–85 (1993).Google Scholar
  12. Srivastar, S., Deepak, D., and Khare, A., Three novel Prognane Glycosides from Leptadenia Reticulata Wight and Arn. Tetrahedron, 50, 789–798 (1994).CrossRefGoogle Scholar
  13. Yoshimura, S., Sakaki, T., Ishibashi, M., Tsuyuki, T., Takahashi, T., Matsushita, K., and Honda, T., Structures of yadanziolides A, B, and C, new bitter principles from Brucea javanica. Chem. Pharm. Bull., 32, 4698–4701 (1984).Google Scholar

Copyright information

© The Pharmaceutical Society of Korea and Springer Netherlands 2011

Authors and Affiliations

  • Jie-Qing Liu
    • 1
  • Cui-Fang Wang
    • 1
  • Xing-Yao Li
    • 1
  • Jian-Chao Chen
    • 1
  • Yan Li
    • 1
  • Ming-Hua Qiu
    • 1
  1. 1.State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of BotanyChinese Academy of SciencesKunmingYunnan, China

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