Chemical and biological investigation of Indigofera ammoxylum (DC.) Polhill. red and white phenotypes through feature-based molecular networking

peer reviewedChemical investigation of ethyl acetate bark extracts of Indigofera ammoxylum red and white phenotypes led to the bio-guided isolation of four previously undescribed flavonoids, named (2S,3R)-3′,7-dihydroxy-4′,6-dimethoxyflavanol (1), (2S,3R)-6-methoxy-7-hydroxyflavanol (2), 2′,3′,7-trihydroxy-4′,6-dimethoxyisoflavone (7) and 2′,5'-dimethoxy-4′,5,7-trihydroxyisoflavanone (8), along with 14 known compounds (3-6 and 9-18). The previously undescribed structures were characterized based on NMR, HRESIMS, UV and IR data. Published spectroscopic data were used to deduce the structure of the known compounds. Eleven of the 18 isolated metabolites were evaluated for anti-inflammatory activity and cytotoxic activity against human liver carcinoma cells and human colon and colorectal adenocarcinoma cells. All tested compounds showed an anti-inflammatory activity (IC 50 NO < 25 μg/mL), and compounds 2 and 3 were more selective than the positive control dexamethasone. Afromorsin (6) showed promising cytotoxic properties against both cancer cell lines (IC 50 18.9 and 11.4 μg/mL). Feature-based molecular networking approach applied to bark and leaves extracts of the two phenotypes allowed to detect bioactive analogues, belonging to the families of flavones, isoflavones, flavanones, flavanols and flavonols, and to explore the chemodiversity of the species. The red and white phenotypes have a similar composition, whereas bark and leaves contain specific chemical entities. Finally, this approach highlighted a cluster of potentially bioactive and undescribed metabolites

Valorization of the biodiversity of Natural Regional Park of Luberon : Phytochemical and pharmacological studies of d'Inula Montana L.

Inula montana L. est une plante utilisée en médecine traditionnelle dans la région méditerranéenne. L’étude phytochimique a permis d’isoler et d’identifier 28 composés à partir des capitules et/ou feuilles d’Inula montana. Six sont des nouveaux composés : un acide sesquiterpénique, nommé Eldarine et cinq dérivés de l’inositol.Dix-neuf sont des composés décrits pour la première fois dans Inula montana.Une monographie de contrôle qualité des capitules d’Inula montana est proposée. Deux méthodes d’analyse qualitative et quantitative par CLUHP ont été mises au point et validées. La première méthode porte sur le dosage du Costunolide. La deuxième méthode concerne le profil des polyphénols avec une évaluation quantitative de trois composés. Ces deux méthodes d’analyse par CLUHP ont permis de réaliser une étude comparative des plantes sauvages et cultivées. Une étude comparative de la plante soumise à différents stress, tels que le stress salin et le stress UV-B ainsi que la plante obtenue par culture in vitro a été conduite.Des éco extraits actifs ont été préparés par extraction assistée par micro-ondes et ultrasons en utilisant les solvants verts à l’aide d’un plan d’expérience. L’activité anti-inflammatoire de différents extraits et molécules d’Inula montana ont été évalués in vitro. Les extraits et les produits purs présentent des activités importantes. Activités des teintures, préparation traditionnelles, d’Inula montana sont comparables à celles d’Arnica montana. Les études phytochimiques et pharmacologiques montrent qu’Inula montana pourrait être proposée comme une alternative à Arnica montana.Inula montana L. is used in traditional medicine of the Mediterranean region.Phytochemical study led to the isolation and identification of 28 compounds from flowers and leaves of Inula montana L. These compounds belong to the family of terpenes, polyphenols, and inositol derivatives.Six of them are new compounds: one new sesquiterpene acid, called Eldarin and five inositol derivatives.Nineteen compounds are reported for the first time in Inula montana.A quality control monography of flowers from Inula montana was established. Two methods of qualitative and quantitative analysis by UHPLC were developed and validated. The first method concerns the profile of sesquiterpene lactones with the quantification of Costunolide. The second method concerns the polyphenols profile with the quantitative evaluation of three compounds. These two methods of analysis by UHPLC allow to conduct the comparative study of wild and cultivated plant.These methods were also used for the comparative study of plants, subjected to different stress, such as salt and UV-B. The vegetal material obtained by in vitro culture was also analyzed by these methods.The active eco-extracts have been developed through the design of experiments by extraction assisted by microwaves and ultrasounds, using green solvents.The anti-inflammatory activity of different extracts and compounds of Inula montana was evaluated in vitro. The extracts and compounds show important activity. Activity of tinctures from Inula montana are similar to the activity of tinctures from Arnica montana.The phytochemical and pharmacological studies show that Inula montana could be proposed as an alternative to Arnica montana

Biologically Active Compounds from Chamaenerion angustifolium and Stachys annua Growing in Azerbaidzhan

International audienc

Chemical Constituents from Roots of Cephalaria media

International audienc

Targeted and non-targeted metabolomic analyses of Heterocapsa cf. bohaiensis under nickel and iron high concentration and its photophysiology

International audienceMicroalgae are able to adapt and to synthesize valuable compounds in response to abiotic stresses such as temperature, UV-radiation or metallic trace elements. We studied this faculty of adaptation by assessing the impact of high metal concentrations on Heterocapsa cf. bohaiensis, a newly isolated dinoflagellate from the New Caledonian coastal water rich in metals. We cultivated H. cf. bohaiensis in continuous culture mode using 10L photobioreactors and exposed the algae to high concentrations (10-3M) of nickel (Ni2+) and/or iron (Fe2+). We then followed its photosynthetic efficiency using Pulse Amplitude Modulated chlorophyll fluorometry and its metabolome with targeted (HPLC-UV-DAD, GC-MS) and non-targeted (LC-MS2 and NMR) approaches. The photosynthetic measurements indicate that H. cf. bohaiensis is tolerant to Ni2+ but sensitive to Fe2+ high concentrations. In presence of Fe2+, Fv/Fm and rETRm decreased from 0.62 to 0.47 and from 156 to 102, respectively. The JIP-tests (i.e. the fast chlorophyll fluorescence transient) suggest that the reduction of photosynthesis in response to Fe2+ is due to a disruption in the electron transport chain rather than a defect in the PSII light absorption and trapping which are on the contrary enhanced by Fe2+. The metabolomics analyses highlight the variation of the main dinoflagellate pigments, Chlorophyll c and a, peridinin, diadinoxanthin and diatoxanthin in response to time and metals and give a first glimpse on the complex metabolomic response to metal stress. These results bring new knowledge on this species and on the impact of nickel and iron on the microalgae photosynthetic pathway and metabolomic responses

Phytochemical Study of Stem Bark of Afzelia africana

International audienceAfzelia africana Sm. (Fabaceae) is a large deciduous tree, widespread in West Africa in dry forest areas, and is found mainly in the northern hemisphere, from Senegal to Cameroon and eastern Uganda. The plant is used in folk medicine to treat various diseases. In Nigeria, A. africana leaves and bark are employed in unstable pregnant and miscarriage, seeds are used in sore throat. Otherwise, leaves, roots, bark and mistletoes are used to treat neuropsychiatric disorders, in the Hauts Bassins region, in the western zone of Burkina Faso. A. africana exhibits several biological activities including antimicrobial antidiabetic and hypolipidemic effects. Methanolic stem bark extract of A. africana exhibited, in vitro, a high activity against Trypanosoma brucei brucei. An EtOAc extract prepared from stem bark of A. africana showed in vitro cytotoxic activity on prostate cancer and breast carcinoma cells.However, very little research has been conducted on this plant. In order to explore the phytochemistry and potential bioactive molecules of A. africana, the stem bark have been investigated. In the present study, we report the isolation of 15 compounds from this plant: five lignans and 10 flavonoids and derivatives. All the purified compounds are isolated for the first time from this plant

Targeted and non-targeted metabolomic analyses of Heterocapsa cf. bohaiensis under nickel and iron high concentration and its photophysiology

International audienceMicroalgae are able to adapt and to synthesize valuable compounds in response to abiotic stresses such as temperature, UV-radiation or metallic trace elements. We studied this faculty of adaptation by assessing the impact of high metal concentrations on Heterocapsa cf. bohaiensis, a newly isolated dinoflagellate from the New Caledonian coastal water rich in metals. We cultivated H. cf. bohaiensis in continuous culture mode using 10L photobioreactors and exposed the algae to high concentrations (10-3M) of nickel (Ni2+) and/or iron (Fe2+). We then followed its photosynthetic efficiency using Pulse Amplitude Modulated chlorophyll fluorometry and its metabolome with targeted (HPLC-UV-DAD, GC-MS) and non-targeted (LC-MS2 and NMR) approaches. The photosynthetic measurements indicate that H. cf. bohaiensis is tolerant to Ni2+ but sensitive to Fe2+ high concentrations. In presence of Fe2+, Fv/Fm and rETRm decreased from 0.62 to 0.47 and from 156 to 102, respectively. The JIP-tests (i.e. the fast chlorophyll fluorescence transient) suggest that the reduction of photosynthesis in response to Fe2+ is due to a disruption in the electron transport chain rather than a defect in the PSII light absorption and trapping which are on the contrary enhanced by Fe2+. The metabolomics analyses highlight the variation of the main dinoflagellate pigments, Chlorophyll c and a, peridinin, diadinoxanthin and diatoxanthin in response to time and metals and give a first glimpse on the complex metabolomic response to metal stress. These results bring new knowledge on this species and on the impact of nickel and iron on the microalgae photosynthetic pathway and metabolomic responses

Targeted and non-targeted metabolomic analyses of Heterocapsa cf. bohaiensis under nickel and iron high concentration and its photophysiology

Microalgae are able to adapt and to synthesize valuable compounds in response to abiotic stresses such as temperature, UV-radiation or metallic trace elements. We studied this faculty of adaptation by assessing the impact of high metal concentrations on Heterocapsa cf. bohaiensis, a newly isolated dinoflagellate from the New Caledonian coastal water rich in metals. We cultivated H. cf. bohaiensis in continuous culture mode using 10L photobioreactors and exposed the algae to high concentrations (10-3M) of nickel (Ni2+) and/or iron (Fe2+). We then followed its photosynthetic efficiency using Pulse Amplitude Modulated chlorophyll fluorometry and its metabolome with targeted (HPLC-UV-DAD, GC-MS) and non-targeted (LC-MS2 and NMR) approaches. The photosynthetic measurements indicate that H. cf. bohaiensis is tolerant to Ni2+ but sensitive to Fe2+ high concentrations. In presence of Fe2+, Fv/Fm and rETRm decreased from 0.62 to 0.47 and from 156 to 102, respectively. The JIP-tests (i.e. the fast chlorophyll fluorescence transient) suggest that the reduction of photosynthesis in response to Fe2+ is due to a disruption in the electron transport chain rather than a defect in the PSII light absorption and trapping which are on the contrary enhanced by Fe2+. The metabolomics analyses highlight the variation of the main dinoflagellate pigments, Chlorophyll c and a, peridinin, diadinoxanthin and diatoxanthin in response to time and metals and give a first glimpse on the complex metabolomic response to metal stress. These results bring new knowledge on this species and on the impact of nickel and iron on the microalgae photosynthetic pathway and metabolomic responses

Identification of Antioxidant Metabolites from Five Plants (Calophyllum inophyllum, Gardenia taitensis, Curcuma longa, Cordia subcordata, Ficus prolixa) of the Polynesian Pharmacopoeia and Cosmetopoeia for Skin Care

Oxidative stress contributes to impairment of skin health, the wound healing process, and pathologies such as psoriasis or skin cancer. Five Polynesian medicinal plants, among the most traditionally used for skin care (pimples, wounds, burns, dermatoses) are studied herein for their antioxidant properties: Calophyllum inophyllum, Gardenia taitensis, Curcuma longa, Cordia subcordata, and Ficus prolixa. Plant extracts were submitted to in vitro bioassays related to antioxidant properties and their bioactive constituents were identified by a metabolomic analytical approach. High performance liquid chromatography with tandem mass spectrometry (HPLC-MS/MS) analysis was performed leading to the characterization of 61 metabolites. Compounds annotated for F. prolixa and C. subcordata extracts were reported for the first time. Antioxidant properties were evaluated by total phenolic content (TPC), free radical scavenging DPPH (1,1-diphenyl-2-picryl-hydrazyl), and Ferric Reducing Antioxidant Power activity (FRAP) assays. F. prolixa extract was the most active one and showed antioxidant intracellular activity on keratinocytes by Anti Oxydant Power 1 assay. Online HPLC-DPPH allowed the identification of phenolic bioactive compounds such as quercetin-O-rhamnoside, rosmarinic acid, chlorogenic acid, procyanidins, epicatechin, 5-O-caffeoylshikimic acid, and curcumin as being responsible for the scavenging properties of these plant extracts. These results highlight the potential of F. prolixa aerial roots as a source of antioxidants for skin care application