Microbial Transformation of (-)-alpha-Bisabolol Towards Bioactive Metabolites

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FIRAT Z., DEMİRCİ F., DEMİRCİ B., KIRMIZIBEKMEZ H., Baser K. H. C.

RECORDS OF NATURAL PRODUCTS, vol.15, no.6, pp.593-601, 2021 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 15 Issue: 6
  • Publication Date: 2021
  • Doi Number: 10.25135/rnp.252.2004.1615
  • Journal Name: RECORDS OF NATURAL PRODUCTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, ABI/INFORM, CAB Abstracts, EMBASE, Veterinary Science Database, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.593-601
  • Keywords: Matricaria recutita L., microbial transformation, bisabolol, antimicrobial activity, antioxidant activity, Penicillium neocrassum, BIOTRANSFORMATION, BISABOLOL, FUNGUS
  • Anadolu University Affiliated: Yes

Abstract

Bisabolol is one of the bioactive constituents of chamomile. It was aimed to biotransform (-)-alpha-bisabolol by different fungi for the production of new bioactive metabolites, which was converted to a-bisabolol oxide A and B by Thamnidium elegans. Additionally, the biotransformation by Penicillium neocrassum yielded a new metabolite, which was characterized as 2-(5-methyl-5-(6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)tetrahydrofuran-2-yl)propan-2-ol = bisafuranol. The substrate and its metabolite mixtures were tested using antioxidant DPPH center dot scavenging assay. Antimicrobial activity was evaluated by an in vitro microdilution assay against a panel of human pathogenic bacteria and yeasts resulting in the lowest MIC and MFC values of 150 mu g/mL. (-)-alpha-Bisabolol was effective against Propionibacterium acnes and Staphylococcus epidermidis (75, 37.5 mu g/mL, respectively). The antioxidant activity of the metabolites was found to be more effective in scavenging free radicals.