Isolation of natural compounds from Phlomis stewartii showing α-glucosidase inhibitory activity

Phytochemistry. 2013 Dec:96:443-8. doi: 10.1016/j.phytochem.2013.09.015. Epub 2013 Oct 10.

Abstract

Stewartiiside (1), a phenylethanoid glycoside and three 28-nortriterpenoids: stewertiisins A-C [(17R)-19(18→17)-abeo-3α,18β,23,24-tetrahydroxy-28-norolean-12-ene, 2; (17R)-19(18→17)-abeo-2α,16β,18β,23,24-pentahydroxy-28-norolean-12-en-3-one, 3; (17R)-19(18→17)-abeo-2α,3α,23,24-tetrahydroxy-28-noroleane-11,13-diene, 4] together with eight known compounds: lunariifolioside (5), notohamosin A (6), phlomispentanol (7), isorhamnetin 3-(6-p-coumaroyl)-β-D-glucopyranoside (8), tiliroside (9), caffeic acid (10), p-hydrxybenzoic acid (11) and oleanolic acid (12) were isolated from the ethyl acetate soluble fraction of the methanolic extract of whole plant of Phlomis stewartii. The structures of these isolates (1-12) were elucidated by the combination of 1D ((1)H and (13)C NMR), 2D (HMQC, HMBC COSY, NOESY) NMR spectroscopy and mass spectrometry (EIMS, HREIMS, FABMS, HRFABMS) and in comparison with literature data of related compounds. All the isolates (1-12) showed α-glucosidase inhibitory activity with IC50 values ranging between 14.5 and 355.4 μM, whereas, compounds 1, 5, 9 and 10 showed promising α-glucosidase inhibitory activity with IC50 values below 30 μM.

Keywords: 28-Nortriterpenoids; Phenylethanosids; Phlomis stewartii; α-Glucosidase inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Caffeic Acids / chemistry
  • Caffeic Acids / isolation & purification*
  • Caffeic Acids / pharmacology*
  • Catechols / chemistry
  • Catechols / isolation & purification*
  • Catechols / pharmacology*
  • Glycoside Hydrolase Inhibitors*
  • Glycosides / chemistry
  • Glycosides / isolation & purification*
  • Glycosides / pharmacology*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pakistan
  • Phenanthrenes / chemistry
  • Phenanthrenes / isolation & purification*
  • Phenanthrenes / pharmacology*
  • Phlomis / chemistry*
  • Stereoisomerism

Substances

  • 2-(3,4-dihydroxyphenyl)ethylO-beta-apiofuranosyl-(1-6)-O-(O-beta-apiofuranosyl-(1-4)-alpha-rhamnopyranosyl-(1-3))-4-O-(E)-caffeoyl-beta-glucopyranoside
  • Caffeic Acids
  • Catechols
  • Glycoside Hydrolase Inhibitors
  • Glycosides
  • Phenanthrenes
  • stewartiiside
  • caffeic acid