Bioactive 30-noroleanane triterpenes from the pericarps of Akebia trifoliata

Molecules. 2014 Apr 4;19(4):4301-12. doi: 10.3390/molecules19044301.

Abstract

Two new 30-noroleanane triterpenes, 2α,3β,20α-trihydroxy-30-norolean-12-en-28-oic acid (1), 2α,3β-dihydroxy-23-oxo-30-norolean-12,20(29)-dien-28-oic acid (2), were isolated from the pericarps of Akebia trifoliata, together with four known ones, 3β-akebonoic acid (3), 2α,3β-dihydroxy-30-noroleana-12,20(29)-dien-28-oic acid (4), 3α-akebonoic acid (5) and quinatic acid (6). Their structures were established on the basis of detailed spectroscopic analysis, and they were all isolated from the pericarps of A. trifoliata for the first time. Compounds 3-6 showed in vitro bacteriostatic activity against four assayed Gram-positive bacterial strains. In particular 3 showed antibacterial activity toward MRSA with a MIC value 25 μg/mL, which was more potent than kanamycin (MIC 125 μg/mL). No compounds showed antibacterial activity toward the three Gram-negative bacteria tested. Compounds 4 and 5 showed interesting in vitro growth inhibitory activity against human tumor A549 and HeLa cell lines, with IC50 values ranging from 8.8 and 5.6 μM, respectively. Compounds 1, 2, 5 and 6 were further revealed to show significant in vitro α-glucosidase inhibitory activity with IC50 values from 0.035 to 0.367 mM, which were more potent than the reference compound acarbose (IC50 0.409 mM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acarbose / pharmacology
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry*
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Fruit / chemistry*
  • Glycoside Hydrolase Inhibitors
  • Gram-Negative Bacteria / drug effects
  • Gram-Negative Bacteria / growth & development
  • Gram-Positive Bacteria / drug effects
  • Gram-Positive Bacteria / growth & development
  • Humans
  • Magnoliaceae / chemistry*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / pharmacology
  • alpha-Glucosidases / chemistry

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents, Phytogenic
  • Glycoside Hydrolase Inhibitors
  • Triterpenes
  • alpha-Glucosidases
  • Acarbose