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NMR and LC‐MS n characterisation of two minor saponins from Ilex paraguariensis
Author(s) -
Martinet A.,
Ndjoko K.,
Terreaux C.,
Marston A.,
Hostettmann K.,
Schutz Y.
Publication year - 2001
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/1099-1565(200101/02)12:1<48::aid-pca560>3.0.co;2-#
Subject(s) - chemistry , oleanolic acid , aglycone , hydrolysis , acid hydrolysis , ursolic acid , oleanane , carbon 13 nmr , proton nmr , stereochemistry , triterpene , chromatography , organic chemistry , glycoside , medicine , alternative medicine , pathology
Two minor saponins obtained from the methanolic extract of the leaves of Ilex paraguariensis have been characterised by 13 C‐NMR, 1 H‐NMR, API‐MS and chemical hydrolysis as oleanolic acid‐3‐ O ‐{β‐ D ‐glucopyranosyl‐(1 → 3)‐α‐ L ‐arabinopyranosyl}‐(28 → 1)‐β‐ D ‐glucopyranosyl ester (guaiacin B) and oleanolic acid‐3‐ O ‐{β‐ D ‐glucopyranosyl‐(1 → 3)‐{α‐ L ‐rhamnopyranosyl‐(1 → 2)}‐α‐ L ‐arabinopyranosyl}‐(28 → 1)‐β‐ D ‐glucopyranosyl ester (nudicaucin C). Both are isomeric forms of the known matesaponins 1 (MSP 1) and 2 (MSP 2) and differ only by the nature of the aglycone: they have oleanolic acid instead of ursolic acid, as found in the matesaponins. These minor saponins have not been fully separated from their major isomers MSP 1 and 2 and were characterised by in‐mixture NMR analysis, LC‐MS and LC‐MS n experiments. Copyright © 2001 John Wiley & Sons, Ltd.