Chemical Constituents of Gomphrena globosa. II

  • Dinda, Biswanath (Department of Chemistry, Tripura University) ;
  • Ghosh, Biplab (Department of Chemistry, Tripura University) ;
  • Achari, Basudev (Medicinal Chemistry Division, Indian Institute of Chemical Biology) ;
  • Arima, Shiho (School of Pharmaceutical Sciences, Kitasato University) ;
  • Sato, Nariko (School of Pharmaceutical Sciences, Kitasato University) ;
  • Harigaya, Yoshihiro (School of Pharmaceutical Sciences, Kitasato University)
  • Published : 2006.06.01

Abstract

One new sterol glucoside, $gomphsterol\;{\beta}-D-glucoside$ 1 along with known compounds, ${\beta}-sitosterol$, stigmasterol, campesterol, $stigmasterol-{\beta}-D-glucoside$, friedelin, 3-epi-friedelinol, allantoin, and $chrysoeriol-7-O-{\beta}-D-glucoside$ have been isolated from the aerial parts of Gomphrena globosa (Amaranthaceae). On the basis of spectroscopic (including 2D NMR) and chemical studies, the structure of 1 was elucidated as $(22E,24S)-24-ethylcholesta-7,9(11),22-trien-3{\beta}-ol-3-O-{\beta}-D-glucopyranoside$. Known compounds are reported for the first time from this plant species.

Keywords

References

  1. Achari, B., Basu, K., and Pakrashi, S.C., Studies on Indian Medicinal Plants, 78. Chemical investigation of Malvaviscus conzattii. J. Natural products, 47(4), 751-751 (1984) https://doi.org/10.1021/np50034a047
  2. Akihisa (Nee Itoh), T., $^{13}C$-NMR Spectral identification of sterols. In: David Nes, W., and Parish, E. J., (eds), Analysis of Sterols and Other Biologically Significant Steroids. London: Academic Press, pp. 251-265, 1989
  3. Buckingham, J., Dictionary of Natural Products, Vol 2. London: Chapman and Hall, pp. 2277, 1994
  4. Buckingham, J. and MacDonald, E, Dictionary of Organic Compounds, 6th ed. London: Chapman & Hall Electronic Publishing Division, pp. 3012, 1996
  5. Corey, E.J. and Ursprung, J.J., The structures of the triterpenes friedelin and cerin. J. American Chemical Society, 78(19), 5041-5051 (1956) https://doi.org/10.1021/ja01600a064
  6. Deb, D.B., The Flora of Tripura State, Vol. 2. New Delhi: Today & Tomorrow's Printers and Publishers, pp. 168-169 (1983)
  7. Dinda, B., Ghosh, B., Arima, S., Sato, N., and Harigaya, Y., Phytochemical investigation of Gomphrena globosa aerial parts. Indian J. Chemistry, 43B(10), 2223-2227 (2004)
  8. Hener, S., Wray, V., Metzger, J.W., and Strack, D., Betacyanins from flowers of Gomphrena globosa. Phytochemistry, 31(5), 1801-1807 (1992) https://doi.org/10.1016/0031-9422(92)83151-N
  9. Holland, L., Diakow, P.R.P., and Taylor, G. J., $^{13}C$-Nuclear magnetic resonance spectra of some C-19-hydroxy, C-5,6-epoxy , C-24 ethyl, and C-19 norsteroids. Canadian J. Chemistry, 56, 3121-3127 (1978) https://doi.org/10.1139/v78-510
  10. Liu, H.-K., Chang, T.-C., and Chu, C.-I., Expectorant principle from Gomphrena globosa-structure determination of a new flavone glycoside. Yao Hsush Tung Pao, 16(1), 55-56 (1981)
  11. Rashed, A.N., Afifi, F.U., Shaedah, M., and Taha, M.O., Investigation of the active constituents of Portulaca oleracea L. (Portulacaceae) growing in Jordan. Pakistan J.Pharmaceutical Science, 17(1), 37-45 (2004)
  12. Ravi, B.N., Kokke, W.C.M.C., Delseth, C., and Djerassi, C., Isolation and structure of 26, 27-cycloaplysterol (petrosterol)-a cyclopropanecontaining marine sterol. Tetrahedron Lett., (45), 4379-4380 (1978)
  13. Rubinstein, I., Goad, J.L., Clague, A.D.H. and Mulheirm, L.J., The 220 MHz NMR spectra of phytosterols, Phytochemistry, 15(1), 195-200 (1976) https://doi.org/10.1016/S0031-9422(00)89083-4
  14. Sahu, N.P., and Chakravarti, R.N., Constituents of the leaves of Argyreia speciosa, Phytochemistry, 10(8), 1949-1949 (1971)
  15. Skaitsa, H., Lazari, D., and Constantinidis, T., Flavonoid compounds of Lamyropsis cynaroides. Biochemical Systematics and Ecology, 28(8), 809-811 (2000) https://doi.org/10.1016/S0305-1978(99)00121-0
  16. Tanaka, R., and Matsunaga, S., Terpene dienols and other constituents from the bark of Phyllanthusflexuosus. Phytochemistry, 27(7), 2273-2277 (1988) https://doi.org/10.1016/0031-9422(88)80141-9
  17. Williams, D.H. and Fleming, I., Spectrometric Methods in Organic Chemistry, 4th ed. New Delhi: Tata McGraw-Hill, pp. 41, 1994