Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Steroids of the spirostan and furostan series from Nolina microcarpa IV. Structures of nolinogenin, nolinospiroside B, and nolinofuroside B

Abstract

A glycoside has been isolated from the plantNolina microcarpa S. Wats. (family Dracaenaceae) which has been called nolinofuroside B and has the structure of 6β-methoxy-3β,5-cyclo-(25S)-furostan-1β,22α,26-triol 1-O-β-D-fucopyranoside 26-O-β-D-glucopyranoside (I). Enzymatic hydrolysis of the bioside (I) yielded nolinospiroside B (III) and nolinogenin (IV). The latter is 6β-methoxy-3β,5-cyclo-(25S)-spirostan-6β-ol, and glycoside (III) is its 1-O-β-D-fucopyranoside.

Literature cited

  1. 1.

    G. B. Shevchuk, Yu. S. Vollerner, A. S. Shashkov, and V. Ya. Chirva, Khim. Prir. Soedin., 672 and 678 (1991).

  2. 2.

    G. B. Shevchuk, Yu. S. Vollerner, A. S. Shashkov, M. B. Gorovits, and V. Ya. Chirva, Khim. Prir. Soedin., 801 (1991).

  3. 3.

    A. V. Kamernitskii, N. K. Abubakirov, M. B. Gorovits, Yu. S. Vollerner, N. E. Voishvillo, I. G. Reshetova, and V. A. Paseshnichenko, The Chemistry of the Spirostanols [in Russian], Moscow (1986), pp. 8–37.

  4. 4.

    E. Stahl, Thin Layer Chromatography, 1st English edition, Springer/Academic Press, New York (1965).

  5. 5.

    R. Kasai, M. Okihara, I. Asakawa, K. Mizutani, and K. Tanaka, Tetrahedron,35, 1427 (1979).

  6. 6.

    C. Altona and C. A. G. Hasnoot, Org. Magn. Res.,13, No. 6, 417 (1980).

  7. 7.

    S. Seo, Y. Tomita, K. Tori, and Y. Yoshimura, J. Am. Chem. Soc.,100, No. 11, 3331 (1978).

  8. 8.

    M. E. Wall, C. R. Eddy, M. L. McClennan, and M. E. Klumpp, Anal. Chem.,24, 1337 (1952).

  9. 9.

    C. R. Eddy, M. E. Wall, and M. K. Scott, Anal. Chem.,25, 266 (1953).

  10. 10.

    W. H. Faul and C. Djerassi, Org. Mass Spectrom.,3, 1187 (1970).

  11. 11.

    M. I. Isaev, M. B. Gorovits, and N. K. Abubakirov, Khim. Prir. Soedin., 156 (1989).

  12. 12.

    M. S. Gonzalez, D. A. Bustos, M. Zudenigo, and E. A. Ruveda, Tetrahedron,42, 755 (1986).

  13. 13.

    T. T. Gorovits, Khim. Prir. Soedin., 263 (1970).

Download references

Additional information

M. V. Frunze Simferopol' State University. Institute of Chemistry of Plant Substances, Uzbekistan Academy of Sciences, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 218–224, March–April, 1992.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Shevchuk, G.V., Vollerner, Y.S., Shashkov, A.S. et al. Steroids of the spirostan and furostan series from Nolina microcarpa IV. Structures of nolinogenin, nolinospiroside B, and nolinofuroside B. Chem Nat Compd 28, 187–192 (1992). https://doi.org/10.1007/BF00630172

Download citation

Keywords

  • Steroid
  • Organic Chemistry
  • Glycoside
  • Enzymatic Hydrolysis
  • Triol