Journals / Records of Natural Products / 2021 / Cilt: 15 - Sayı: 6

Microbial Transformation of (–)-α-Bisabolol Towards Bioactive Metabolites

Pages
593–601
DOI
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

The antioxidant activity of the metabolites was found to be more effective in scavenging free radicals.

📌 3 Key Takeaways

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Objective & Hypothesis:Bisabolol is one of the bioactive constituents of chamomile.
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Key Findings & Data: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.
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Conclusion & Impact:The antioxidant activity of the metabolites was found to be more effective in scavenging free radicals.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

Özet

Bisabolol is one of the bioactive constituents of chamomile. It was aimed to biotransform (–)-α- bisabolol by different fungi for the production of new bioactive metabolites, which was converted to α-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• 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 μg/mL. (–)-α-Bisabolol was effective against Propionibacterium acnes and Staphylococcus epidermidis (75, 37.5 μg/mL, respectively). The antioxidant activity of the metabolites was found to be more effective in scavenging free radicals.

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Cite This Article

FİRAT, Z., DEMİRCİ, F., DEMİRCİ, B., KIRMIZIBEKMEZ, H., BAŞER, H. C. (2021). Microbial Transformation of (–)-α-Bisabolol Towards Bioactive Metabolites. Records of Natural Products, Cilt: 15 - Sayı: 6, 593–601. https://ajindex.com/articles/340389

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References (12)

  1. K.H. Kubeczka (2015). History and sources of essential oil research, In: Handbook of Essential Oils: Science, Technology, and Applications, second ed., eds: K.H.C. Baser, G. Buchbauer, FL: CRC Press, Boca Raton, pp.5–43
  2. M. Ashour, M. Wink and J. Gershenzon (2010). Biochemistry of terpenoids: Monoterpenes, sesquiterpenes and diterpenes, In: Annual Plant Reviews: Biochemistry of Plant Secondary Metabolism, Second ed., ed: M. Wink, Wiley, New York, pp. 258-303
  3. K.A. El Sayed, M. Yousaf, M.T. Hamann, M.A. Avery, M. Kelly and P. Wipf (2002). Microbial and chemical transformation studies of the bioactive marine sesquiterpenes (S)-(+)-curcuphenol and - curcidiol isolated from a deep reef collection of Jamaican sponge Didiscus oxeata, J. Nat. Prod. 65, 1547-1553
  4. X.C. Ma, M. Ye, L.J. Wu and D.A. Guo (2006). Mircobial transformation of curdione by Mucor spinosus, Enzyme Microb Technol. 38, 367-371
  5. Z. Alresly, U. Lindequist, M. Lalk, A. Porzel, N. Arnold and L. A. Wessjohann (2016). Bioactive triterpenes from the fungus Piptoporus betulinus, Rec. Nat. Prod. 10, 103-108
  6. H. Schilcher (2005). Legal situation of German chamomile: Monographs, In: Chamomile Industrial Profiles, eds: R. Franke and H. Schilcher, FL: CRC Press, Boca Raton, pp.7-38
  7. G.P.P. Kamatou and A.M. Viljoen (2010). A review of the application and pharmacological properties of α-bisabolol and α-bisabolol-rich oils, J. Am. Oil Chem. Soc. 87, 1-7
  8. D.L. McKay and J.B. Blumberg (2006). A review of the bioactivity and potential health benefits of chamomile tea (Matricaria recutita L.), Phytother. Res. 20, 519-530
  9. G.O. Leite, A.F. Dubois, R.L. Seeger, A.A. Boligon, J.G.M. Costa, T.H. Lugokenski, A.R. Campos R. Fachinetto, J.P. Kamdem, J.B.T. Rocha and C. Wanger (2016). In vitro antioxidant activity investigation of Vanillomopsis arborea Baker aqueous extracts, essential oil and isolated compound: (-)-α-bisabolol. Pharmacologia 7, 193-201
  10. S. Baylac and P. Racine (2003). Inhibition of 5-lipoxygenase by essential oils and other natural fragrant extracts, Int. J. Aromatherapy. 13, 138-142
  11. B.F. Brehm-Stecher and E.A. Johnson (2003). Sensitization of Staphylococcus aureus and Escherichia coli to antibiotics by the sesquiterpenoids nerolidol, farnesol, bisabolol, and apritone, Antimicrob. Agents. Chemother. 47, 3357-3360
  12. M.A. Longo and M.A. Sanroman (2006). Production of food aroma compounds: Microbial and Enzymatic Methodologies, Food Technol. Biotechnol. 44