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One new pregnane glycoside from the seeds of cultivated Brucea javanica

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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.

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References

  • Anderson, F., Judith, L., Gilardi, R., and George, C., Structure of bruceine B hydrate. Acta Crystallogr. C, 43, 801–803 (1987).

    Article  Google Scholar 

  • 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).

    Article  Google Scholar 

  • 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).

    Article  Google Scholar 

  • Harigaya, Y., Konda, Y., Iguchi, M., and Onda, M., Spectroscopic studies of brusatol. J. Nat. Prod., 52, 740–748 (1989).

    Article  CAS  Google Scholar 

  • 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).

    Article  PubMed  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol Methods, 65, 55–63 (1983).

    Article  PubMed  CAS  Google Scholar 

  • Reed, L. J. and Muench, H., A simple method of estimating fifty percent endpoints. Am. J. Hyg., 27, 493–497 (1938).

    Google Scholar 

  • 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 

  • 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).

    CAS  Google Scholar 

  • Srivastar, S., Deepak, D., and Khare, A., Three novel Prognane Glycosides from Leptadenia Reticulata Wight and Arn. Tetrahedron, 50, 789–798 (1994).

    Article  Google Scholar 

  • 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).

    CAS  Google Scholar 

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Correspondence to Ming-Hua Qiu.

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Liu, JQ., Wang, CF., Li, XY. et al. One new pregnane glycoside from the seeds of cultivated Brucea javanica . Arch. Pharm. Res. 34, 1297–1300 (2011). https://doi.org/10.1007/s12272-011-0809-5

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  • DOI: https://doi.org/10.1007/s12272-011-0809-5

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