Protein tyrosine phosphatase 1B (PTP1B) inhibitors from Morinda citrifolia (Noni) and their insulin mimetic activity

J Nat Prod. 2013 Nov 22;76(11):2080-7. doi: 10.1021/np400533h. Epub 2013 Nov 13.

Abstract

As part of our ongoing search for new antidiabetic agents from medicinal plants, we found that a methanol extract of Morinda citrifolia showed potential stimulatory effects on glucose uptake in 3T3-L1 adipocyte cells. Bioassay-guided fractionation of this active extract yielded two new lignans (1 and 2) and three new neolignans (9, 10, and 14), as well as 10 known compounds (3-8, 11-13, and 15). The absolute configurations of compounds 9, 10, and 14 were determined by ECD spectra analysis. Compounds 3, 6, 7, and 15 showed inhibitory effects on PTP1B enzyme with IC50 values of 21.86 ± 0.48, 15.01 ± 0.20, 16.82 ± 0.42, and 4.12 ± 0.09 μM, respectively. Furthermore, compounds 3, 6, 7, and 15 showed strong stimulatory effects on 2-NBDG uptake in 3T3-L1 adipocyte cells. This study indicated the potential of compounds 3, 6, 7, and 15 as lead molecules for antidiabetic agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells / metabolism
  • 4-Chloro-7-nitrobenzofurazan / analogs & derivatives
  • 4-Chloro-7-nitrobenzofurazan / pharmacology
  • Adipocytes / drug effects
  • Animals
  • Deoxyglucose / analogs & derivatives
  • Deoxyglucose / pharmacology
  • Hypoglycemic Agents / chemistry
  • Hypoglycemic Agents / isolation & purification*
  • Hypoglycemic Agents / pharmacology
  • Inhibitory Concentration 50
  • Insulin / pharmacology*
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology*
  • Mice
  • Molecular Structure
  • Morinda / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
  • Republic of Korea

Substances

  • 3,4,3',4'-tetrahydroxy-9,7'beta-epoxylignano-7beta,9'-lactone
  • Hypoglycemic Agents
  • Insulin
  • Lignans
  • trans-(3)E-3-(3,4-dihydroxybenzylidene)-5-(3,4-dihydroxyphenyl)-4-(hydroxymethyl)dihydrofuran-2(3H)-one
  • Deoxyglucose
  • Protein Tyrosine Phosphatase, Non-Receptor Type 1
  • 4-Chloro-7-nitrobenzofurazan
  • 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose