A bioactive cycloartane triterpene from Garcinia hombroniana

Nat Prod Res. 2016 Jun;30(12):1388-97. doi: 10.1080/14786419.2015.1060594. Epub 2015 Jul 9.

Abstract

The dichloromethane bark extract of Garcinia hombroniana yielded one new cycloartane triterpene; (22Z,24E)-3β-hydroxycycloart-14,22,24-trien-26-oic acid (1) together with five known compounds: garcihombronane G (2), garcihombronane J (3), 3β acetoxy-9α-hydroxy-17,14-friedolanostan-14,24-dien-26-oic acid (4), (22Z, 24E)-3β, 9α-dihydroxy-17,14-friedolanostan-14,22,24-trien-26-oic acid (5) and 3β, 23α-dihydroxy-17,14-friedolanostan-8,14,24-trien-26-oic acid (6). Their structures were established by the spectral techniques of NMR and ESI-MS. These compounds together with some previously isolated compounds; garcihombronane B (7), garcihombronane D (8) 2,3',4,5'-tetrahydroxy-6-methoxybenzophenone (9), volkensiflavone (10), 4''-O-methyll-volkensiflavone (11), volkensiflavone-7-O-glucopyranoside (12), volkensiflavone-7-O-rhamnopyranoside (13), Morelloflavone (14), 3''-O-methyl-morelloflavone (15) and morelloflavone-7-O-glucopyranoside (16) were evaluated for cholinesterase enzymes inhibitory activities using acetylcholinesterase and butyrylcholinesterase. In these activities, compounds 1-9 showed good dual inhibition on both the enzymes while compounds 10-16 did not reasonably contribute to both the cholinesterases inhibitory effects.

Keywords: (22Z, 24E)-3β-hydroxycycloart-14,22,24-trien-26-oic acid; Garcinia hombroniana; acetylcholinesterase; butyrylcholinesterase.

MeSH terms

  • Acetylcholinesterase / metabolism
  • Biflavonoids / chemistry
  • Biflavonoids / pharmacology
  • Butyrylcholinesterase / metabolism
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology*
  • Drug Evaluation, Preclinical / methods
  • Garcinia / chemistry*
  • Molecular Structure
  • Spectrometry, Mass, Electrospray Ionization
  • Triterpenes / chemistry
  • Triterpenes / pharmacology

Substances

  • (22Z,24E)-3beta-hydroxycycloart-14,22,24-trien-26-oic acid
  • Biflavonoids
  • Cholinesterase Inhibitors
  • Triterpenes
  • garcihombronane G
  • garcihombronane J
  • morelloflavone
  • cycloartane
  • Acetylcholinesterase
  • Butyrylcholinesterase