A new approach to procyanidins synthesis with potent anti-adipogenic effects

Bioorg Med Chem Lett. 2019 Aug 15;29(16):2079-2084. doi: 10.1016/j.bmcl.2019.07.008. Epub 2019 Jul 5.

Abstract

Convenient structure modification of (+)-catechin (1) induced by nonthermal dielectric barrier discharge (DBD) plasma treatment afforded three novel methylene-linked flavan-3-ol oligomers, methylenetetracatechin (2), methylenetricatechin (3), and methylenedicatechin (4), together with two known catechin dimers, bis 8,8'-catechinylmethane (5) and bis 6,8'-catechinylmethane (6). The structures of the three new catechin oligomers 2-4 with methylene bridges were elucidated by detailed 1D- and 2D-NMR analysis, and the absolute configurations were established by the observation of circular dichroism (CD). The novel products 2 and 3 showed significantly enhanced anti-adipogenic capacities against both pancreatic lipase and differentiation of 3T3-L1 preadipocytes compared to the parent (+)-catechin.

Keywords: (+)-Catechin; Adipocyte differentiation; Dielectric barrier discharge plasma; Oligomerization; Pancreatic lipase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells
  • Adipocytes / drug effects*
  • Animals
  • Anti-Obesity Agents / chemical synthesis
  • Anti-Obesity Agents / pharmacology*
  • Catechin / analogs & derivatives*
  • Catechin / pharmacology*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology*
  • Lipase / antagonists & inhibitors
  • Mice
  • Molecular Structure
  • Proanthocyanidins / chemical synthesis
  • Proanthocyanidins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Obesity Agents
  • Enzyme Inhibitors
  • Proanthocyanidins
  • Catechin
  • Lipase