Abstract
Saponins are complex multifunctional molecules made up of an aglycone (steroid or triterpene) and of one or several chains of sugars. They are polar and their isolation and separation require solvents and adsorbents of high polarities, sometimes associated with moderately high temperatures. A necessary step in their structural elucidation is the identification of their components, and this is often done by chemical or enzymic degradations. Under these conditions or during the isolation process, these fragile molecules lend themselves to structural changes and what is thought bona fide to be of natural origin, may be the artifactual product of a chemical rearrangement. Such transformations occur on the aglycone skeleton or on the sugar part, or consist in the loss of a labile substituent.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
T. J. King and J. P. Yardley, The structure of bassic acid, J. Chem. Soc. 4308 (1961).
I. Kitagawa, A. Inada, I. Yosioka, R. Somanathan, and M. U. S. Sultanbawa, Protobassic acid, a genuine sapogenol of seed kernels of Madhuca longifolia L., Chem. Pharm. Bull. 20:630 (1972).
G. Massiot, C. Lavaud, C. Delaude, G. Van Binst, S. P. F. Miller, and H. M. Fales, Saponins from Tridesmostemon claessenssi, Phytochemistry 29:3291 (1990).
I. Kitagawa, M. Yoshikawa, and J. Yosioka, Saponin and sapogenol XIII. Structures of three soybean saponins: soyasaponin I, soyasaponin II, and soyasaponin III, Chem. Pharm. Bull. 24:121 (1976).
I. Kitagawa, M. Yoshikawa, H. K. Wang, M. Saito, V. Tosirisuk, T. Fujiwara, and K. Tomita, Revised structures of soyasapogenols A, B and E, oleanene—sapogenols from soybean. Structures of soyasaponin I, II and III, Chem. Pharm. Bull. 30:2294 (1982).
C. Djerassi, D. B. Thomas, A. L. Livingston, and C. R. Thompson, The structure and stereochemisny of medicagenic acid, J. Am. Chem. Soc. 79:5292 (1957).
A. L. Livingston, Lucernic acid, a new triterpene from alfalfa, J. Org. Chem. 24:1567 (1959).
G. Massiot, C. Lavaud, D. Guillaume, and L. Le Men-Olivier, Reinvestigation of the sapogenins and prosapogenins from alfalfa (Medicago sativa), J. Agric. Food Chem. 36:902 (1988).
W. Oleszek, M. Jurzysta, M. Ploszynski, I. J. Colquhoun, K. R. Price, and G. R. Fenwick, Zahnic acid tridesmoside and other dominant saponins from alfalfa (Medicago sativa L.) aerial parts, J. Agric. Food Chem. 40:191 (1992).
M. Kapundu, A. Penders, R. Warin, C. Delaude, and R. Huls, Structure du kotschyoside, saponoside nouveau isolé de Aspilia kotschyi (Sch. Bip.) Oliv. Bull. Soc. Chim. Belg. 97:329 (1988).
G. Massiot, X-F. Chen, C. Lavaud, L. Le Men-Olivier, C. Delaude, A. Viari, P. Vigny, and J. Duval, Saponins from stem bark of Petersianthus macrocarpus, Phytochemistry 31:3571 (1992).
G. Massiot, C. Lavaud, M. Benkhaled, and L. Le Men-Olivier, Soyasaponin VI, a new maltol conjugate from alfalfa and soybean, J. Nat. Prod. 55:1339 (1992).
S. Tsurumi, T. Takagi, and T. Hashimoto, A γ-pyronyl—triterpenoid saponin from Pi sum sativum, Phytochemistry 31:2435 (1992).
S. Kudou, M. Tonomura, C. Tsukamoto, M. Shimoyamada, T. Uchida, and K. Okubo, Isolation and structural elucidation of the major genuine soybean saponin, Biosci. Biotech. Biochem. 56:142 (1992).
S. Kudou, M. Tonomura, C. Tsukamoto, T. Uchida, and K. Okubo, Isolation and structural elucidation of DDMP—conjugated soyasaponins as genuine saponins from soybean seeds, Biosci. Biotech. Biochem. 57:546(1993).
G. Massiot, M-G. Dijoux, C. Lavaud, L. Le Men-Olivier, J. D. Connolly, and D. M. Sheeley, Seco—glycosides of oleanolic acid from Beta vulgaris, Phytochemistry 37:1667 (1994).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1996 Plenum Press, New York
About this chapter
Cite this chapter
Massiot, G., Dijoux, MG., Lavaud, C. (1996). Saponins and Artifacts. In: Waller, G.R., Yamasaki, K. (eds) Saponins Used in Food and Agriculture. Advances in Experimental Medicine and Biology, vol 405. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0413-5_15
Download citation
DOI: https://doi.org/10.1007/978-1-4613-0413-5_15
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-8041-2
Online ISBN: 978-1-4613-0413-5
eBook Packages: Springer Book Archive