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

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

1
Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, SFR CAP’SANTE, UFR de Pharmacie, Université de Reims Champagne-Ardenne, Reims 51687, France
2
Division of Pharmacognosy and Natural Products Chemistry, School of Pharmacy, University of Athens, Panepistimioupolis, Zografou, Athens 15771, Greece
3
Biomatériaux et Inflammation en Site Osseux, EA 4691, SFR CAP-Santé, UFR de Pharmacie, Université de Reims Champagne Ardenne, Reims 51100, France
*
Authors to whom correspondence should be addressed.
Academic Editor: Derek J. McPhee
Received: 18 October 2016 / Revised: 13 November 2016 / Accepted: 15 November 2016 / Published: 21 November 2016
(This article belongs to the Section Natural Products)
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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. View Full-Text
Keywords: dermo-cosmetic agents; Centrifugal Partition Chromatography; 13C-NMR dereplication; E-astringin; taxifolin; tyrosinase, elastase and collagenase activity dermo-cosmetic agents; Centrifugal Partition Chromatography; 13C-NMR dereplication; E-astringin; taxifolin; tyrosinase, elastase and collagenase activity
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MDPI and ACS Style

Angelis, A.; Hubert, J.; Aligiannis, N.; Michalea, R.; Abedini, A.; Nuzillard, J.-M.; Gangloff, S.C.; Skaltsounis, A.-L.; Renault, J.-H. Bio-Guided Isolation of Methanol-Soluble Metabolites of Common Spruce (Picea abies) Bark by-Products and Investigation of Their Dermo-Cosmetic Properties. Molecules 2016, 21, 1586.

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