Secondary metabolites of Bagassa guianensis Aubl. wood: A study of the chemotaxonomy of the Moraceae family

International audienceIn order to explain the durability of the Moraceae plant family, phytochemistry of Bagassa guianensis was performed. Ethyl acetate extract was obtained from the heartwood and 18 secondary metabolites were isolated, including 6 moracins [6-O-methyl-moracin M, 6-O-methyl-moracin N and moracin Z; previously identified: moracin M, moracin N and moracin P], 8 stilbenoids [presently identified: ( )-epialboctalol and arachidin 4; previously identified: alboctalol, trans-resveratrol, arachidin 2, trans-oxyresveratrol and artogomezianol], 3 previously identified flavonoids, steppogenin, katuranin and dihydromorin, bsitosterol and resorcinol. Previous studies suggest that stilbenoids are responsible for the natural durability of wood. Our study has determined that B. guianensis is closely related to Morus sp. in phylogeny and should be included in the Moreae sensu stricto tribe of the Moraceae family

Approche métabolomique combinant l'analyse LC-MS/MS et les réseaux moléculaires pour suivre les constituants bioactifs des amandes de Calophyllum inophyllum (tamanu) pendant le processus de séchage

International audienceTamanu oil, obtained from the nuts of Calophyllum inophyllum L. (Calophyllaceae), was traditionally used to cure various skin problems and ailments in French Polynesia. Nuts and containing oil are also used for skin care. Since the drying of nuts is an important stage for oil preparation, the objective of our study was to develop an analytical method to evaluate oil quality during nuts drying process following different drying parameters. Using a metabolomic approach combining LC-MS/MS analysis and molecular networking, the obtained data revealed differences in the metabolites chemical classes occurring in resulting oils. For the first time, our study provides new findings regarding the occurrence and evolution of the metabolites in tamanu nuts during the drying process. The developed method provided a powerful analytical tool aiming a better identification of bioactive components formed in tamanu nuts during drying process and will be helpful to produce high quality oil for a natural active cosmetic ingredient. An efficient metabolomic approach was implemented to identify markers inducing variability in chemical composition during drying process of nuts. Thus, this set-up analytical method successfully applied in tamanu could be used to the study of metabolites of a wide range of plants.L'huile de tamanu, obtenue à partir des amandes de Calophyllum inophyllum L. (Calophyllaceae), est traditionnellement utilisée pour soigner divers problèmes et affections cutanées en Polynésie française. Les amandes et l'huile qu'elles contiennent sont également utilisées pour les soins de la peau. Elles sont connues pour traiter différents types d'affections cutanées et utilisées comme ingrédient cosmétique naturel. Le séchage des amandes étant une étape importante pour la préparation de l'huile, l'objectif de notre étude était de développer une méthode analytique pour évaluer la qualité de l'huile (composition chimique et rendement en huile) pendant le processus de séchage des amandes et en fonction de différents paramètres de séchage (facteurs abiotiques). En utilisant une approche métabolomique combinant l'analyse LC-MS/MS et la mise en réseau moléculaire, les données obtenues ont révélé des différences au sein des classes chimiques de métabolites présents dans les huiles. Des marqueurs induisant la variabilité de la composition chimique pendant le processus de séchage des amandes de tamanu ont pu être identifiés. La méthode développée fournit un bon outil analytique qui apporte une meilleure identification des composés bioactifs formés dans les amandes de tamanu pendant le processus de séchage et sera utile pour produire une huile de qualité en tant qu’ingrédient cosmétique naturel. De plus, cette approche métabolomique mise en place dans le cas du C. inophyllum pourra être utilisée pour l'étude des métabolites provenant d’une large gamme de plantes

Metabolomic approach using LC-MS/MS analysis and molecular networking to follow up bioactive constituents of Callophyllum inophyllum nuts during drying process

International audienc

Triterpenoid saponins from the aerial parts of Solidago virgaurea alpestris with inhibiting activity of Candida albicans yeast-hyphal conversion

International audienceAs part of research for treatments to combat oral dryness, our evaluation of the activity of an aqueous extract of Solidago virgaurea (L.) ssp. alpestris (Asteraceae) revealed activity against Candida albicans hyphae, the pathogenic form of this yeast. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which six oleanane-type triterpenoid saponins were isolated. Three of these were isolated for the first time, as 3-O-(beta-D-glucopyranosyl-(1 -> 3)-beta-D-glucopyranosyl)-28-O-(beta-D-fucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl)-polygalacic acid (virgaureasaponin 4), 3-O-(beta-D-glucopyranosyl)-28-O-(beta-D-fucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl)-polygalacic acid (virgaureasaponin 5) and 3-O-(beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-(5-O-acetylapiofuranosyl-(1 -> 3)-[4-O-(3-(3-hydroxy-1-oxobutoxy)-1-oxobutyl)]-beta-D-fucopyranosyl]-polygalacic acid (virgaureasaponin 6).Their structures were established by carrying out 1D and 2D NMR experiments along with HRMS analyses. All of the six saponins were evaluated to ascertain their inhibition of C albicans yeast-hyphal conversion, and four of them showed significant inhibition

Oleodaphnoic Acid and Coriaceol, Two New Natural Products from the Stem Bark of Wikstroemia coriacea

molecule

Naphtho-Gamma-Pyrones Produced by Aspergillus tubingensis G131: New Source of Natural Nontoxic Antioxidants

International audienceSeven naphtho-gamma-pyrones (NγPs), including asperpyrone E, aurasperone A, dianhydroaurasperone C, fonsecin, fonsecinone A, fonsecin B, and ustilaginoidin A, were isolated from Aspergillus tubingensis G131, a non-toxigenic strain. The radical scavenging activity of these NγPs was evaluated using ABTS assay. The Trolox equivalent antioxidant capacity on the seven isolated NγPs ranged from 2.4 to 14.6 µmol L −1. The toxicity and ability of the NγPs to prevent H 2 O 2-mediated cell death were evaluated using normal/not cancerous cells (CHO cells). This cell-based assay showed that NγPs: (1) Are not toxic or weakly toxic towards cells and (2) are able to protect cells from oxidant injuries with an IC 50 on H 2 O 2-mediated cell death ranging from 2.25 to 1800 µmol mL −1. Our data show that A. tubingensis G131 strain is able to produce various NγPs possessing strong antioxidant activities and low toxicities, making this strain a good candidate for antioxidant applications in food and cosmetic industries

Pentacyclic triterpenes from Manilkara bidentata resin. Isolation, identification and biological properties

International audienceThree 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 (3 beta-O-acetyl-alpha-amyrin and 3 beta-O-trans cinnamyl-alpha-amyrin) and a lupane-type derivative (3 beta-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-1 beta 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

Triterpenoid saponins from the aerial parts of Solidago virgaurea alpestris with inhibiting activity of Candida albicans yeast-hyphal conversion

International audienceAs part of research for treatments to combat oral dryness, our evaluation of the activity of an aqueous extract of Solidago virgaurea (L.) ssp. alpestris (Asteraceae) revealed activity against Candida albicans hyphae, the pathogenic form of this yeast. Systematic bioassay-guided fractionation of this extract gave an active saponin-containing fraction from which six oleanane-type triterpenoid saponins were isolated. Three of these were isolated for the first time, as 3-O-(beta-D-glucopyranosyl-(1 -> 3)-beta-D-glucopyranosyl)-28-O-(beta-D-fucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl)-polygalacic acid (virgaureasaponin 4), 3-O-(beta-D-glucopyranosyl)-28-O-(beta-D-fucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl)-polygalacic acid (virgaureasaponin 5) and 3-O-(beta-D-glucopyranosyl)-28-O-(alpha-L-rhamnopyranosyl-(1 -> 3)-beta-D-xylopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 2)-(5-O-acetylapiofuranosyl-(1 -> 3)-[4-O-(3-(3-hydroxy-1-oxobutoxy)-1-oxobutyl)]-beta-D-fucopyranosyl]-polygalacic acid (virgaureasaponin 6).Their structures were established by carrying out 1D and 2D NMR experiments along with HRMS analyses. All of the six saponins were evaluated to ascertain their inhibition of C albicans yeast-hyphal conversion, and four of them showed significant inhibition