Saponins from Allium minutiflorum with antifungal activity
Three saponins, minutoside A–C, were isolated from the bulbs of Allium minutiflorum Regel. Their stereostructure was carried out by spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry, and chemical methods. The isolated compounds showed a significant antifungal activity depen...
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Published in | Phytochemistry (Oxford) Vol. 68; no. 5; pp. 596 - 603 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier Ltd
01.03.2007
Elsevier |
Subjects | |
Online Access | Get full text |
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Summary: | Three saponins, minutoside A–C, were isolated from the bulbs of
Allium minutiflorum Regel. Their stereostructure was carried out by spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry, and chemical methods. The isolated compounds showed a significant antifungal activity depending on their concentration and with the following rank: minutoside B
>
minutoside
C
≫
minutoside A.
Three saponins, named minutoside A (
1), minutoside B (
2), minutoside C (
3), and two known sapogenins, alliogenin and neoagigenin, were isolated from the bulbs of
Allium minutiflorum Regel. Elucidation of their structure was carried out by comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry. The structures of the new compounds were identified as (25R)-furost-2α,3β,6β,22α,26-pentaol 3-
O-[β-
d-xylopyranosyl-(1
→
3)-
O-β-
d-glucopyranosyl-(1
→
4)-
O-β-
d-galactopyranosyl] 26-
O-β-
d-glucopyranoside (
1), (25S)-spirostan-2α,3β,6β-triol 3-
O-β-
d-xylopyranosyl-(1
→
3)-
O-β-
d-glucopyranosyl-(1
→
4)-
O-β-
d-galactopyranoside (
2), and (25R)-furost-2α,3β,5α,6β,22α,26-esaol 3-
O-[β-
d-xylopyranosyl-(1
→
3)-
O-β-
d-glucopyranosyl-(1
→
4)-
O-β-
d-galactopyranosyl] 26-
O-β-
d-glucopyranoside (
3). The isolated compounds were evaluated for their antimicrobial activity. All the novel saponins showed a significant antifungal activity depending on their concentration and with the following rank: minutoside B
>
minutoside C
≫
minutoside A. No appreciable antibacterial activity was recorded. The possible role of these saponins in plant–microbe interactions is discussed. |
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Bibliography: | http://dx.doi.org/10.1016/j.phytochem.2006.10.009 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0031-9422 1873-3700 |
DOI: | 10.1016/j.phytochem.2006.10.009 |