TY - JOUR
T1 - Oleanolic acid and hederagenin glycosides from Weigela stelzneri
AU - Rezgui, Abdelmalek
AU - Mitaine-Offer, Anne Claire
AU - Miyamoto, Tomofumi
AU - Tanaka, Chiaki
AU - Delemasure, Stéphanie
AU - Dutartre, Patrick
AU - Lacaille-Dubois, Marie Aleth
PY - 2016/3/1
Y1 - 2016/3/1
N2 - Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, and 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosylhederagenin 28-O-β-d-xylopyranosyl-(1 → 6)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid and 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.
AB - Four previously undescribed and one known oleanolic acid glycosides were isolated from the roots of Weigela stelzneri, and one previously undescribed and three known hederagenin glycosides were isolated from the leaves. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid, 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid 28-O-β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl ester, and 3-O-β-d-glucopyranosyl-(1 → 2)-α-l-arabinopyranosylhederagenin 28-O-β-d-xylopyranosyl-(1 → 6)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranosyl ester. The majority of the isolated compounds were evaluated for their cytotoxicity against two tumor cell lines (SW480 and EMT-6), and for their anti-inflammatory activity. The compounds 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranosyloleanolic acid and 3-O-β-d-glucopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-xylopyranosyl-(1 → 4)-β-d-xylopyranosyl-(1 → 3)-α-l-rhamnopyranosyl-(1 → 2)-β-d-xylopyranosyloleanolic acid exhibited the strongest cytotoxicity on both cancer cell lines. They revealed a 50% significant inhibitory effect of the IL-1β production by PBMCs stimulated with LPS at a concentration inducing a very low toxicity of 23% and 28%, respectively.
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U2 - 10.1016/j.phytochem.2015.12.016
DO - 10.1016/j.phytochem.2015.12.016
M3 - Article
C2 - 26805449
AN - SCOPUS:84957439631
VL - 123
SP - 40
EP - 47
JO - Phytochemistry
JF - Phytochemistry
SN - 0031-9422
ER -