title: Pentacyclic triterpenes from Manilkara bidentata resin. Isolation, identification and biological properties.
abstract: Three pentacyclic triterpenes were isolated for the first time from resinous plant Manilkara bidentata. Ultrasound-assisted extraction with ethanol was chosen after a comparison of various extraction methods. Analysis of the extract was performed by HPLC with evaporative light scattering detection and semi-preparative HPLC has enabled us to isolate two urs-12-enes (3β-O-acetyl-α-amyrin and 3β-O-trans cinnamyl-α-amyrin) and a lupane-type derivative (3β-O-trans cinnamyl lupeol). Structures were elucidated on the basis of HRESIMS, atmospheric pressure photoionization MS, and homo- and heteronuclear correlation NMR experiments. Antioxidant and anti-inflammatory activities were determined on Manilkara extract and isolated fractions. We have also investigated their action on collagen and fibronectin synthesis, two very important proteins of the extracellular matrix. Thus, Manilkara extract was able to decrease IL-1β and IL-8 pro-inflammatory cytokines. These activities exhibit the potential use of Manilkara extract as an anti-inflammatory and anti-aging ingredient for pharmaceutical and cosmetic industries.
authors.affiliation: Institut de Chimie Organique et Analytique (ICOA), UMR-CNRS 7311, Université d'Orléans, Rue de Chartres, BP 6759 Orléans Cedex 2, France.
authors.forename: Boutayna
authors.initials: B
authors.lastname: Rhourri-Frih
authors.affiliation: LVMH Recherche., 185, Avenue de Verdun, 45804 Saint Jean de Braye, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Renimel
authors.affiliation: Laboratoire de Chimie et Physique Approche Multi échelle des Milieux Complexes (LCPA2MC) EA 4632, Institut Jean Barriol, Fédération de Recherche 2843, Université de Lorraine, ICPM, 1, Boulevard Arago, 57078 Metz Technopole Cedex 03, France.
authors.forename: Patrick
authors.initials: P
authors.lastname: Chaimbault
authors.affiliation: LVMH Recherche., 185, Avenue de Verdun, 45804 Saint Jean de Braye, France.
authors.forename: Patrice
authors.initials: P
authors.lastname: André
authors.affiliation: Spectropole, FR1739, Aix-Marseille Université, Campus Scientifique Saint Jérôme, service 511, 13397 Marseille Cedex 20, France.
authors.forename: Gaëtan
authors.initials: G
authors.lastname: Herbette
authors.affiliation: Institut de Chimie Organique et Analytique (ICOA), UMR-CNRS 7311, Université d'Orléans, Rue de Chartres, BP 6759 Orléans Cedex 2, France. Electronic address: michel.lafosse@univ-orleans.fr.
authors.forename: Michel
authors.initials: M
authors.lastname: Lafosse
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D003094:Collagen / Q000096:biosynthesis; D005109:Extracellular Matrix / Q000378:metabolism; D005353:Fibronectins / Q000096:biosynthesis; D006801:Humans; D053583:Interleukin-1beta / Q000378:metabolism; D016209:Interleukin-8 / Q000378:metabolism; D015603:Keratinocytes / Q000187:drug effects* / Q000378:metabolism; D032129:Manilkara / Q000737:chemistry*; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D012116:Resins, Plant / Q000737:chemistry / Q000494:pharmacology; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
chemical_list: D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D005353:Fibronectins; D053583:Interleukin-1beta; D016209:Interleukin-8; D010936:Plant Extracts; D012116:Resins, Plant; D014315:Triterpenes; D003094:Collagen
keywords: Anti-inflammatory activity; Extracellular matrix; Manilkara bidentata; Pentacyclic triterpenes; Radical scavenging activity; Sapotaceae