Antioxidant Biomarkers from Vanda coerulea Stems Reduce Irradiated HaCaT PGE-2 Production as a Result of COX-2 Inhibition

BACKGROUND: In our investigations towards the isolation of potentially biologically active constituents from Orchidaceae, we carried out phytochemical and biological analyses of Vanda species. A preliminary biological screening revealed that Vanda coerulea (Griff. ex. Lindl) crude hydro-alcoholic stem extract displayed the best DPPH /(•)OH radical scavenging activity and in vitro inhibition of type 2 prostaglandin (PGE-2) release from UV(B) (60 mJ/cm(2)) irradiated HaCaT keratinocytes. PRINCIPAL FINDINGS: Bio-guided fractionation and phytochemical analysis led to the isolation of five stilbenoids: imbricatin (1) methoxycoelonin (2) gigantol (3) flavidin (4) and coelonin (5). Stilbenoids (1-3) were the most concentrated in crude hydro-alcoholic stem extract and were considered as Vanda coerulea stem biomarkers. Dihydro-phenanthropyran (1) and dihydro-phenanthrene (2) displayed the best DPPH/(•)OH radical scavenging activities as well as HaCaT intracellular antioxidant properties (using DCFH-DA probe: IC(50) 8.8 µM and 9.4 µM, respectively) compared to bibenzyle (3) (IC(50) 20.6 µM). In turn, the latter showed a constant inhibition of PGE-2 production, stronger than stilbenoids (1) and (2) (IC(50) 12.2 µM and 19.3 µM, respectively). Western blot analysis revealed that stilbenoids (1-3) inhibited COX-2 expression at 23 µM. Interestingly, stilbenoids (1) and (2) but not (3) were able to inhibit human recombinant COX-2 activity. CONCLUSIONS: Major antioxidant stilbenoids (1-3) from Vanda coerulea stems displayed an inhibition of UV(B)-induced COX-2 expression. Imbricatin (1) and methoxycoelonin (2) were also able to inhibit COX-2 activity in a concentration-dependent manner thereby reducing PGE-2 production from irradiated HaCaT cells. Our studies suggest that stilbenoids (1-3) could be potentially used for skin protection against the damage caused by UV(B) exposure

262_LicAdevs

Compilation of raw NMR data (FID) with structural description (pms file) and annotation (PDF) of the newly described dihydrobenzofuran derivatives (LicAF1 and LicAF2) of licochalcone A (LicA). The dataset contains 1D, 1H NMR of photoisomerized LicAF1/2 and LicA, as well as the 1D 1HNMR data of co-isolated major licorice compounds (echinatin, licoisoflavone A, licoflavone B, licochalcone B, glabrone)

Phytochemical and biological investigations of Vanda coerulea Griff ex. Lindl and Vanda teres (Roxb.) Lindl (Orchidaceae)

Des analyses phytochimiques des extraits hydro-alcooliques des tiges, feuilles et racines de Vanda coerulea Griff ex.Lindl et Vanda teres (Roxb.) Lindl (Orchidaceae) nous ont conduit à l'isolement et à l'identification de métabolites caractéristiques des tiges soit, cinq stilbénoïdes (flavidin, imbricatin, coelonin méthoxycoelonin et gigantol) et trois glucopyranosyloxybenzyle-malates, respectivement. Ces derniers, nouvellement décrits, ont été dénommés vandatérosides I à III. Les trois stilbénoïdes les plus concentrés, l'imbricatin, la méthoxycoelonin et le gigantol, présentent une activité anti-oxydante (neutralisation des EOR intracellulaires), anti-inflammatoire cutanée (inhibition de la production de PGE-2 et de l'expression de la COX-2) et inhibitrice de l'expression de MMP-1,2 et 9 impliquées dans la dégradation de la matrice dermique. Par ailleurs, le vandatéroside II et dans une moindre mesure le vandatéroside I stimulent l'activité enzymatique des complexes I et II et de la cytochrome C oxydase de la chaîne respiratoire mitochondriale. Les vandatérosides favorisent l'expression de trois protéines de différenciation des kératinocytes (involucrine, desmogléine I et transglutaminase I) contribuant au renouvellement de l'épiderme. Structuralement très différents, les stilbénoïdes de Vanda coerulea et les vandatérosides de Vanda teres présentent des activités in vitro complémentaires intéressantes dans une optique de prévention du vieillissement cutané.Phytochemical analyses of crude stem, leaf and root crude extracts of Vanda coerulea Griff ex.Lindl and Vanda teres (Roxb.) Lindl (Orchidaceae) led us to the identification of stem-specific metabolites such as five stilbenoids (flavidin, imbricatin, coelonin methoxycoelonin, and gigantol) and three glucosyloxybenzyl malates derivatives, respectively. The latter were described for the first time and thus were named vandaterosides I to III. The most concentrated stilbenoids, imbricatin, methoxycoelonin and gigantol, displayed antioxidant (intra-cellular ROS neutralization) and skin anti-inflammatory activities (inhibition of PGE-2 production and COX-2 expression). They were also able to prevent the release of MMP-1, 2 and 9 implied in dermal matrix breakdown. Vandateroside II, and to a lesser extend vandateroside I, enhanced the activities of mitochondrial respiratory enzymes: complex I, II and cytochrome C oxidase. Vandaterosides increased the expression of proteins implied in keratinocytes differentiation (involucrin, desmoglein I and transglutaminase I), thus they could facilitate skin rejuvenation. Stilbenoids isolated from Vanda coerulea and vandaterosides from Vanda teres, displayed complementary biological activities slowing down the skin ageing process

Phytochemical and biological investigations of Vanda coerulea Griff ex. Lindl and Vanda teres (Roxb.) Lindl (Orchidaceae)

Des analyses phytochimiques des extraits hydro-alcooliques des tiges, feuilles et racines de Vanda coerulea Griff ex.Lindl et Vanda teres (Roxb.) Lindl (Orchidaceae) nous ont conduit à l'isolement et à l'identification de métabolites caractéristiques desPhytochemical analyses of crude stem, leaf and root crude extracts of Vanda coerulea Griff ex.Lindl and Vanda teres (Roxb.) Lindl (Orchidaceae) led us to the identification of stem-specific metabolites such as five stilbenoids (flavidin, imbricatin, coel

Liquiritigenin: annotated 1D 1H NMR spectrum (400 MHz, DMSO-d6) and qNMR data for purity determination

This data set contains the qHNMR spectrum of Liquiritigenin acquired at 400 MHz in DMSO-d6. The sample was prepared with 3,5-dinotrobenzoic acid as internal calibrant (IC). The spreadsheets for the purity calculations by both the 100% method and the absolute IC method are also included. Furthermore, the data set contains the .mol file of liquiritigenin and the annotated/assigned 1D 1H spectrum as .pdf file

Etudes phytochimiques et biologiques de Vanda coerulea Griff ex. Lindl et de Vanda teres (Roxb) Lindl. (Orchidaceae)

Des analyses phytochimiques des extraits hydro-alcooliques des tiges, feuilles et racines de Vanda coerulea Griff ex.Lindl et Vanda teres (Roxb.) Lindl (Orchidaceae) nous ont conduit à l isolement et à l identification de métabolites caractéristiques des tiges soit, cinq stilbénoïdes (flavidin, imbricatin, coelonin méthoxycoelonin et gigantol) et trois glucopyranosyloxybenzyle-malates, respectivement. Ces derniers, nouvellement décrits, ont été dénommés vandatérosides I à III. Les trois stilbénoïdes les plus concentrés, l imbricatin, la méthoxycoelonin et le gigantol, présentent une activité anti-oxydante (neutralisation des EOR intracellulaires), anti-inflammatoire cutanée (inhibition de la production de PGE-2 et de l expression de la COX-2) et inhibitrice de l expression de MMP-1,2 et 9 impliquées dans la dégradation de la matrice dermique. Par ailleurs, le vandatéroside II et dans une moindre mesure le vandatéroside I stimulent l activité enzymatique des complexes I et II et de la cytochrome C oxydase de la chaîne respiratoire mitochondriale. Les vandatérosides favorisent l expression de trois protéines de différenciation des kératinocytes (involucrine, desmogléine I et transglutaminase I) contribuant au renouvellement de l épiderme. Structuralement très différents, les stilbénoïdes de Vanda coerulea et les vandatérosides de Vanda teres présentent des activités in vitro complémentaires intéressantes dans une optique de prévention du vieillissement cutané.Phytochemical analyses of crude stem, leaf and root crude extracts of Vanda coerulea Griff ex.Lindl and Vanda teres (Roxb.) Lindl (Orchidaceae) led us to the identification of stem-specific metabolites such as five stilbenoids (flavidin, imbricatin, coelonin methoxycoelonin, and gigantol) and three glucosyloxybenzyl malates derivatives, respectively. The latter were described for the first time and thus were named vandaterosides I to III. The most concentrated stilbenoids, imbricatin, methoxycoelonin and gigantol, displayed antioxidant (intra-cellular ROS neutralization) and skin anti-inflammatory activities (inhibition of PGE-2 production and COX-2 expression). They were also able to prevent the release of MMP-1, 2 and 9 implied in dermal matrix breakdown. Vandateroside II, and to a lesser extend vandateroside I, enhanced the activities of mitochondrial respiratory enzymes: complex I, II and cytochrome C oxidase. Vandaterosides increased the expression of proteins implied in keratinocytes differentiation (involucrin, desmoglein I and transglutaminase I), thus they could facilitate skin rejuvenation. Stilbenoids isolated from Vanda coerulea and vandaterosides from Vanda teres, displayed complementary biological activities slowing down the skin ageing process.STRASBOURG ILLKIRCH-Pharmacie (672182101) / SudocPARIS-BIUP (751062107) / SudocSudocFranceF

Arbres et allergies respiratoires dans l' Est de la France

STRASBOURG ILLKIRCH-Pharmacie (672182101) / SudocSudocFranceF

265_MoringaInfla

Contains the 1D 1H NMR data of the Moringa seed extract (MSE) and Moringa Isothiocyanate (MIC-1), as well as HiFSA data of MIC-1 (pms file). The repository also contains the quantitative 1H NMR spectra of the investigated turmeric extract and the enriched curcuminoid material, together with spreadsheets involved in the quantitative analysis. Finally, the data set contains the spreadsheets containing all data pertaining to the biological experiments and the figures in the main manuscript (doi: 10.1371/journal.pone.0182658)

282_8PA

This folder contains the NMR datasets ( 1D 1H, 2D COSY, HSQC, HMBC) related to the structural description of 8-prenylapigenin (8PA), the NMR data associated with the structure analysis of bavachalcone mistakenly sold as 8-prenylapigenin, as well as the structure verification of co-isolated abyssinone II and licochalcone C