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Minutaside A, new a-amylase inhibitor flavonol glucoside from Tagetes minuta: Antidiabetic, antioxidant, and molecular modeling studies

مؤلف البحث
Sabrin RM Ibrahim, Gamal A Mohamed, Mohamed MM Abdel-Latif, Shahenda M El-Messery, Nawal M Al Musayeib, Ibrahim A Shehata.
قسم البحث
مجلة البحث
Starch/Stärke
الناشر
WILEY-VCH Verlag GmbH
تصنيف البحث
1
عدد البحث
NULL
موقع البحث
DOI 10.1002/star.201500068
سنة البحث
2015
المشارك في البحث
ملخص البحث

Investigation of the EtOAc fraction of Tagetes minuta L. (Asteraceae) aerial parts has afforded a
new flavonol glucoside, minutaside A (quercetagetin 6-O-(6-O-hexanoyl)-b-D-glucopyranoside)
(1), together with four known flavonoids: axillarin 7-O-b-D-glucopyranoside (2), quercetagetin
3,7-dimethoxy-6-O-b-D-glucopyranoside (3), quercetagetin 7-methoxy-6-O-b-D-glucopyranoside
(4), and quercetagetin 6-O-b-D-glucopyranoside (5). Their structures were established by
multiple spectroscopic methods in addition to HRESIMS (high-resolution electrospray
ionisation mass spectra) and comparison with literature data. The antioxidant and anti-diabetic
activities of the isolated flavonoids were evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH)
and a-amylase inhibition assays. Compounds 1 and 5 showed significant antioxidant activity
(84.1 and 83.0% at a 20 mM dose, respectively). Compounds 1, 4, and 5 exhibited strong aamylase inhibitory activity compared with acarbose (a reference a-amylase inhibitor). However, 2
and 3 showed moderate activity. Molecular modeling studies of 1–5 that included docking,
flexible alignment, and surface mapping were performed to evaluate their recognition profile aamylase receptor. In docking simulations, 5 displayed a binding mode similar to that of acarbose
in the active site of a-amylase enzyme.