Biosynthesis of saponins in the genus Medicago |
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Authors: | Aldo Tava Carla Scotti and Pinarosa Avato |
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Institution: | (1) CRA-FLC Centro di Ricerca per le Produzioni Foraggere e Lattiero Casearie, v.le Piacenza 29, 26900 Lodi, Italy;(2) Dipartimento Farmaco-Chimico, Universit? di Bari Aldo Moro, via Orabona 4, 70125 Bari, Italy |
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Abstract: | Saponins from Medicago species are glycosidic compounds with an aglycone moiety formed through the enzymatic cyclization of 2,3-oxidosqualene by
the β-amyrin cyclase. All the saponins from Medicago genus possess the triterpenic pentacyclic nucleus belonging to the class of β-amyrin. The so formed β-amyrin skeleton can
be further modified by oxidative reactions, mediated by cytochromes belonging to the class of cytochrome P450, to give different
saponin compounds, characterized by the presence of hydroxyl or carboxyl groups located in specific positions of the triterpenic
skeleton. Based on the position and the oxidation degree of the substituents, it is possible to distinguish two groups of
saponins (sapogenins) in Medicago spp: (1) sapogenins possessing an OH group on C-24 (soyasapogenols A, B and E) without any substituent at the C-28 atom,
and (2) sapogenins possessing the COOH group at C-28 that are associated with different oxidation degrees (zero, OH, CHO,
COOH) at C-23. These results seem to indicate that the oxidation at C-24 and the presence of the COOH group at C-28 are mutually
exclusive. The subdivision in the aglycone moiety is reflected also in the sugar moiety, operated by glycosyltranferases,
as the saponins of the two groups differ for the position and the nature of the sugar chains. Based on these findings, new
considerations on the biosynthesis of saponins in the genus Medicago can be drawn and a biosynthetic scheme is proposed. |
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