Abstract
A set of novel trans-tiliroside derivatives were synthesized. The structures of the derivatives were identified by their IR, 1H-NMR, and MS spectra analysis. Their anti-diabetic activities were evaluated on the insulin resistant (IR) HepG2 cell model. As a result, compounds 7a, 7c, 7h, and trans-tiliroside exhibited significant glucose consumption-enhancing effects in IR-HepG2 cells compared with the positive control (metformin). This research provides useful clues for further design and discovery of anti-diabetic agents.
Highlights
The complex metabolic syndrome, diabetes mellitus, is a major worldwide human health concern that is estimated to affect 300 million people by the year 2025 [1]
Compound 6 was used as a key intermediate for the synthesis of derivatives 7a-7h, which were obtained by the Knoevenagel-Doebner reaction of 6 with a series of aldehydes in the presence of pyridine [9,10,11,12,13,14,15]
An insulin resistant (IR) HepG2 cell model [16,17,18] was used for appraising the anti-hyperglycemic effectws of the synthesized trans-tiliroside derivatives
Summary
The complex metabolic syndrome, diabetes mellitus, is a major worldwide human health concern that is estimated to affect 300 million people by the year 2025 [1]. Molecules 2010, 15 of insulin in the liver and peripheral tissues, together with pancreatic cell defects, is a major feature of the pathophysiology of human NIDDM [2,3,4]. Further photochemical and bioactive analysis studies afforded an anti-diabetic compound, kaempferol-3-O-β-D-(6-O-transp-cinnamoyl)glucopyranoside As a part of trans-tiliroside, kaempferol-3-O-β-D-glucopyranose (4) and related analogues revealed weak anti-diabetes activity [7,8], so the cinnamoyl part of trans-tiliroside is presumed to be the the critical factor for increasing the activity. This paper deals with the synthesis of a series of novel trans-tiliroside derivatives by replacing the cinnamoyl ring, as well as their biological activities
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