Antidiabetic ellagitannins from pomegranate flowers: inhibition of α-glucosidase and lipogenic gene expression.
Two new ellagitannins containing a rare 3-oxo-1,3,3a,8b-tetrahydrofuro[3,4-b]benzofuran moiety, namely punicatannins A (1) and B (2), were isolated from pomegranate (Punica granatum) flowers. Their structures with absolute configuration were determined by detailed analysis of spectroscopic data, electronic circular dichroism (ECD) calculation, and chemical hydrolysis. A plausible biogenetic route involving a key enzymatic 1,4-Michael addition is proposed. Punicatannin A showed potent inhibition of α-glucosidase and lipogenic gene expression.
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, Rhode Island 02881, USA.
Tao
T
Yuan
Yuanqing
Y
Ding
Chunpeng
C
Wan
Liya
L
Li
Jialin
J
Xu
Ke
K
Liu
Angela
A
Slitt
Daneel
D
Ferreira
Ikhlas A
IA
Khan
Navindra P
NP
Seeram
D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D035264:Flowers / Q000737:chemistry*; D015870:Gene Expression; D065089:Glycoside Hydrolase Inhibitors; D047348:Hydrolyzable Tannins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D007004:Hypoglycemic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D050155:Lipogenesis; D029561:Lythraceae / Q000737:chemistry*; D015394:Molecular Structure
D004791:Enzyme Inhibitors; D065089:Glycoside Hydrolase Inhibitors; D047348:Hydrolyzable Tannins; D007004:Hypoglycemic Agents