Bio-Guided Isolation of Methanol-Soluble Metabolites of Common Spruce (Picea abies) Bark by-Products and Investigation of Their Dermo-Cosmetic Properties

Molecules. 2016 Nov 21;21(11):1586. doi: 10.3390/molecules21111586.

Abstract

Common spruce (Picea abies L.) is a fast-growing coniferous tree, widely used in several countries for the production of sawn wood, timber and pulp. During this industrial exploitation, large quantities of barks are generated as waste materials. The aim of this study was the bio-guided investigation and the effective recovery of methanol-soluble metabolites of common spruce bark for the development of new dermo-cosmetic agents. The active methanol extract was initially fractionated by Centrifugal Partition Chromatography (CPC) using a triphasic solvent system in a step-gradient elution mode. All resulting fractions were evaluated for their antibacterial activity, antioxidant activity and their capability to inhibit tyrosinase, elastase and collagenase activity. In parallel, the chemical composition of each fraction was established by combining a 13C-NMR dereplication approach and 2D-NMR analyses. As a result, fourteen secondary metabolites corresponding to stilbene, flavonoid and phenolic acid derivatives were directly identified in the CPC fractions. A high amount (0.93 g) of E-astringin was recovered from 3 g of crude extract in a single 125 min run. E-Astringin significantly induced the tyrosinase activity while E-piceid, taxifolin, and taxifolin-3'-O-glucopyranoside exhibited significant anti-tyrosinase activity. The above compounds showed important anti-collagenase and antimicrobial activities, thus providing new perspectives for potential applications as cosmetic ingredients.

Keywords: 13C-NMR dereplication; Centrifugal Partition Chromatography; E-astringin; dermo-cosmetic agents; taxifolin; tyrosinase, elastase and collagenase activity.

MeSH terms

  • Anti-Infective Agents / chemistry
  • Anti-Infective Agents / pharmacology
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Chemical Fractionation / methods
  • Cosmetics / chemistry*
  • Cosmetics / isolation & purification*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Magnetic Resonance Spectroscopy
  • Methanol / chemistry*
  • Microbial Sensitivity Tests
  • Picea / chemistry*
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification*
  • Plant Extracts / pharmacology
  • Solubility

Substances

  • Anti-Infective Agents
  • Antioxidants
  • Cosmetics
  • Enzyme Inhibitors
  • Plant Extracts
  • Methanol