Determination of Plant Saponins and Some of Gypsophila Species: A review of the literature

Year 2008, Volume: 36 Issue: 2, 129 - 135, 01.04.2008

A. Nihal Yücekutlu Işık Bildacı

Abstract

In this study, chemical and physical properties of unripe saponins obtained by extraction from the roots ofÇöven Gypsophila simonii , an endemic plant, were investigated and isolated. Unripe saponins were separated into itscomponents by thin layer chromatography and the Rf values of spots obtained under this study were calculated. Thestructure of the component in the spot which was expected to be pure was investigated by spectral methods such as1H NMR,13C NMR, FTIR and EIMS and named Gypsogenin ester saponin. The findings indicate that the proposedstructure of that sponin was as a new Gypsogenin ester C31H51O3 [1]

Keywords

Gypsophila, Gypsophila simonii, Saponin, Sapogenins

References

• [1] Cevrimli, B. S., Kariptas E. and Yucekutlu A. N., Isolation of Saponin from Dried Roots of Gypsophila simonii Hub. Mor, Pakistan Journal of Biological Sciences, 10 (2007) 1944–1946.
• [2] Davis, P.H., Flora of Turkey and East Aegean Islands, 1972. University Press, Vol. 2, Edinburgh, 157.
• [3] Koyuncu, M., TUBITAK ve DPT Projesi; No: TBAG-DPT. Ç. Sek. 6 (199 T 094).
• [4] Acabes B., A. M. Diaz-Lanza and M. Bernabe, A saponin the roots of Gypsophila Bermejoi, Photochemistry, 7 (1998) 2077.
• [5] Hostettmann, K., and Marston, A., Chemistry and Pharmacology of Natural Products: Saponins. Cambridge University Press, pp. 326-327, 1998.
• [6] Borges, del Castillo, J., Zeitoun, B. A., Arriaga, F. J. and Vazquez, P., Fitoterapia, 57 (1986) 61.
• [7] Frechet, D., Christ, B., Monegier du Sorbier, B., Fischer, H. and Vuilhorgne, M., Phytochemistry, 30 (1991) 927.
• [8] Kochetkov, N. K., Khorlin, A. J. and Ovodov, J. S., Tetrahedron Lett., 8 (1963) 477.
• [9] Hani, M., Elgamal, A., Soliman, H. S. M., Duddeck, H., Mikhova, B. and Gartmann, M., Z., Naturforsch., 50 (1995) 563.
• [10] Hani, M., Elgamal A., Soliman H. S. M., Karawya, M. S., Mikhova, B. and Duddeck H., Phytochemistry, 38 (1995) 1481.
• [11] Agrawal, P. K., Jain D. C. and. Gupta R. K, Carbon-13 NMR spectroscopy of steroidal saponins, Phytochemistry, 24 (1984) 2479.
• [12] Hiller, M., M. Rochal, B. Linzer, Triterpen Saponine, Pharmazie, 21(1996) 713.
• [13] Bernadete, P. S., Allyne, C. S., Graziela, M. S., Tatiana P. M. and Jose´ P. P., A New Bioactive Steroidal Saponin from Agave attenuata, Z. Naturforsch., 57c (2002) 423-428.
• [14] Sung, T. V., Peter-Katalinic J., and Adam G., Bidesmosidik triterpenoid saponin from Schefflera octpylla, Phytochemistry, 30 (1991) 3717.
• [15] Yoshikawa, M., Murakami T., Madsuda H., and Yamarahara J., Bioactive saponins and glycosdes. III. Horse chesnut (1): The structures, inhibitory effects on ethanol absorption and hypogıycemic activity of escins Ia. Ib. 2b. and 3a from the seeds of Aesculus hippocastanum L., Chem. Pharm Bull., 44 (1996) 1454.
• [16] Zengin, A., Cemalettin B., Cyclamen coum bitkisinden izole edilen saponin maddesinin aydınlatılması, 12. Ulusal Kimya Kongresi, 1998, Trakya Üniversitesi Fen Edebiyat Fakültesi, Kimya.
• [17] Henry, M., Rochal M., and Bennini, B., Biosynthesis and accumulation of saponins in Gypsophila paniculata, Phytochemistry, 30 (1991)1819.
• [18] Frechet, D., Bruno C., Bertrand D.S., Four triterpenoid saponins from dried roots of Gypsophila species, Photochemistry, 30 (1991) 927.
• [19] Hostettmann, K., Marston, A. Saponins, Cambridge University Press: New York, NY, 1995, 232-306.
• [20] Akiyama, T., Tanaka, O., Shibata, S., Chemical Studies on the Oriental Plant Drugs, XXXII. Saponins of the Roots of Platycodon Grandiflorum A. De Candolle(3). The Structure of a Prosapogenin, 3-O-B-Glucosyl platycodigenin. Chem. Pharm. Bull. 20 (1972) 1957–1961.
• [21] Fenwick, G.R., Price K.R., Tsukamoto C. and Okubo K., Saponins. In Saponins in Toxic Substances in Crop Plants, [F.J.P. D’Mello, C.M. Duffus and J.H. Duffus, editors]. Cambridge: The Royal Society of Chemistry, 1991.
• [22] Kerem Z., Makkar H. P. S. and Becker K., The biological action of saponins in animal systems: a review, George Francis, British Journal of Nutrition, 88 (2002) 587–605.
• [23] Lasztity, R., Hidvegi, M., Bata, A., Saponins in food. Food Rev. Int. 14 (1998) 371–390.
• [24] Oleszek, W.A., Chromatographic determination of plant saponins. J. Chromatogr. A. 967 (2002) 147–162.
• [25] Hostettmann, K., Marston, A., Saponins. Chemistry and pharmacology of natural products. Cambridge University Press, Cambridge, 2005.
• [26] Grenby, T.H., Intense sweeteners for the food industry: an overview. Trends Food Sci. Technol. 2 (1991) 2–6.
• [27] Kitagawa, I., Licorice root. A natural sweetener and an important ingredient in Chinese medicine. Pure Appl. Chem. 74 (2002) 1189– 1198.
• [28] Heng, L., Vincken, J.-P., van Koningsveld, G.A., Legger, L., Gruppen, H., van Boekel, M.A.J.S., Roozen, J.P., Voragen, A.G.J., Bitterness of saponins and their content in dry peas. J. Sci. Food Agric. 86 (2006) 1225–1231.
• [29] Price, K.R., Johnson, I.T., Fenwick, G.R., The chemistry and biological significance of saponins in foods and feedstuffs. Crit. Rev. Food Sci. Nutr. 26 (1987) 27–135.
• [30] Attele, A.S., Wu, J.A., Yuan, C.S., Ginseng pharmacology. Multiple constituents and multiple actions. Biochem. Pharmacol. 58 (1999) 1685–1693.
• [31] Sparg, S.G., Light, M.E., van Staden, J., Biological activities and distribution of plant saponins. J. Ethnopharmacol. 94 (2004) 219– 243.
• [32] Uematsu, Y., Hirata, K., Saito, K., Spectrophotometric determination of saponin in Yucca extract used as food additive. J. AOAC Int. 83 (2000) 1451–1454.
• [33] Hardman, R., in Board of Pharmaceutical Sciences (Editor), Conception and Contraception, Excerpta Medica, Amsterdam, p. 60, 1975.
• [34] Oakenful, D. & Sidhu, G. S. Could saponins be a useful treatment for hypercholesterolemia? Eur. J. Clin. Nutr., 44 (1990) 9-88.
• [35] Lilian, U. Thompson, Potential health benefits and problems associated with antinutrients in foods Food Research International 26 (1993) 131-149.
• [36] Corea, G., E. Fattorusso, V. Lanzotti, R. Capasso, A.A. Izzo, J. Agric. Food Chem. 53 (2005) 935.
• [37] Matsuura H., J. Nutr. 131 (2001) 1000.
• [38] Koch, H., Deutsche Apothek. Zeits. 133 (1993) 63.
• [39] Yoshiki, Y., Kudou, S., Okubo, K. Relationship Between Chemical Structures and Biological Activities of Triterpenoid Saponins from Soybean. Biosci. Biotechnol. Biochem. 62 (1998) 2291–2300.
• [40] Baytop T., İstanbul Üniversitesi Farmasotik Botanik Kitabı, İstanbul, 1991.
• [41] Mizutani, K., Othani K., Wei X., Saponins from Anemone rivularis, Planta Medica, 65 (1984) 327.
• [42] Baytop, T., Türkiye’de Bitkiler ile Tedavi, Nobel Tıp Kitap Evleri, 2. Baskı, İstanbul, 1999.
• [44] Marston, A., Wolfender J.L. and Hostettmann K., Analysis and isolation of saponins from plant material. In Saponins in Food, Feedstuffs and Medicinal Plants, Annual Proceedings of the Phytochemical Society, pp. 1–12, 2000.
• [45] Muir, A.D., Ballantyne K.D. and Hall T.W., LCMS and LC-MS/MS analysis of saponins and sapogenins – comparison of ionization techniques and their usefulness in compound identification. In Saponins in Food, Feedstuffs and Medicinal Plants, Annual Proceedings of the Phytochemical Society, pp. 35–42, 2000.
• [46] Schopke, T., Non-NMR methods for structure elucidation of saponins. In Saponins in Food, Feedstuffs and Medicinal Plants, Annual Proceedings of the Phytochemical Society, pp. 106–113, 2000.
• [47] Ismailov, A.I., Aliev A.M., Uchen. Zap. 37 (1974) 60.
• [48] Malaviya N., and Khanna M. Saponins from Deutzıa corymbosa, Phytochemistry, 30 (1991) 2798-2800.
• [49] Zhao, L., Chen W., and Fang Q., Triterpenoide saponins from Anemone flaccida, Planta Medica, 56 (1990) 92.
• [50] Delay, C., Gavin J.A., Aumelas A., Bonnet P.- A., and Roumestand C., Isolation and Structure Elucidation of a higly heamoltic Saponin from the Merck Saponin Extract Using High- Field Gradient- Enhance NMR Tecniques, Carbohydrate Research, 302 (1997) 67-78.
• [51] Zhao, W., Wolfender J.-L., Hostettmann K., Cheng K., Xu R., and Qin G.,Triterpenes and triterpenoide saponins from Mussaenda pubescens, Phytochemistry, 45 (1997) 1073- 1078.
• [52] Mostad, H. B. and Doehl J., Seperation and characterization of oleanene-type pen-tacyclıc triterpenes from Gypsophila arrostii by liquid chromatography-mass spectrometry, Journal of Chromatography, 396 (1987) 157-168.
• [53] Boders, C.L., Descending Paper Chromatography of Oligosaccarides, J. of Chem. Edu., 49 (1972) 437-438.