The
effects of three B-type proanthocyanidin (PA) dimers covering
procyanidin B2 (B-0g), procyanidin B2 3′-O-gallate (B-1g),
and procyanidin B2 3,3′-di-O-gallate (B-2g) on 3T3-L1 preadipocyte
differentiation and the underlying mechanisms were investigated. The
results showed that digalloylated B-type PA dimers (B-2g) strongly
inhibited 3T3-L1 preadipocyte differentiation through disrupting the
integrity of the lipid raft structure and inhibiting the expression
of peroxisome proliferator-activated receptor gamma (PPARγ)
and CCAAT/enhancer-binding protein alpha (C/EBPα) and then downregulating
the expression of acetyl-CoA carboxylase (ACC) and fatty acid synthase
(FAS) factors, followed by B-1g, while B-0g had little effect. The
different inhibitory effects were mainly due to the difference in
the B-type PA dimer structure and the ability to interfere with lipid
rafts. The greater the galloylation degree of B-type PA dimers, the
stronger the ability to disrupt the lipid raft structure and oppose
3T3-L1 preadipocyte differentiation. In addition, galloylated B-type
PA dimers had greater molecular hydrophobicity and topological polarity
surface area and could penetrate into the lipid rafts to form multiple
hydrogen bonds with the rafts by molecular dynamics simulation. These
findings highlighted that the strong lipid raft-perturbing potency
of galloylated B-type PA dimers was responsible for inhibition of
3T3-L1 preadipocyte differentiation.
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