Artefact formation during acid hydrolysis of saponins from Medicago spp.
Phytochemistry
; 138: 116-127, 2017 Jun.
Article
em En
| MEDLINE
| ID: mdl-28256274
ABSTRACT
Artefact compounds obtained during acid hydrolysis of saponins from Medicago spp. (Fabaceae), have been monitored and evaluated by GC-FID. Their identification has been performed by GC-MS and 1H and 13C NMR. Saponins with different substituents on the triterpenic pentacyclic aglycones were considered, and their hydrolysis products were detected and quantified during 10 h of time course reaction. From soyasapogenol B glycoside the well known soyasapogenols B, C, D and F were obtained together with a previously undescribed sapogenol artefact identified as 3ß,22ß,24-trihydroxyolean-18(19)-en and named soyasapogenol H. From a zanhic acid saponin two major artefact compounds identified as 2ß,3ß,16α-trihydroxyolean-13(18)-en-23,28-dioic acid and 2ß,3ß,16α-trihydroxyolean-28,13ß-olide-23-oic acid were obtained, together with some zanhic acid. Other compounds, detected in very small amount in the reaction mixture, were also tentatively identified based on their GC-MS and UV spectra. The other most characteristic saponins in Medicago spp., hederagenin, bayogenin and medicagenic acid glycosides, under acidic condition of hydrolysis, released instead the correspondent aglycones and generated a negligible amount of artefacts. Nature of artefacts and mechanism of their formation, involving a stable tertiary carbocation, is here proposed and discussed for the first time.
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Saponinas
/
Medicago
Tipo de estudo:
Prognostic_studies
Idioma:
En
Revista:
Phytochemistry
Ano de publicação:
2017
Tipo de documento:
Article