New Apigenin Glycoside, Polyphenolic Constituents, Anti-inflammatory and Hepatoprotective Activities of Gaillardia grandiflora and Gaillardia pulchella Aerial Parts.

ABSTRACT

BACKGROUND: Gaillardia grandiflora Hort. ex Van Houte and Gaillardia pulchella Foug are flowering plants widely cultivated in Egypt for their ornamental value. Previous reports demonstrated that sesquiterpene derivatives represent the major compounds in both species. Moreover, only few flavones were identified from genus Gaillardia and few studies on the cytotoxicity of G. pulchella were found. AIM OF THE STUDY Investigation of the phenolic constituents of the aerial parts of both species and evaluation of their anti-inflammatory and hepatoprotective activities. MATERIALS AND METHODS: The 80% aqueous methanol extracts (AME) were prepared for both plants and evaluated for their biological activities. Phytochemical investigation of both extracts resulted in isolation of twelve compounds, which have been identified on the basis of ultraviolet, 1D and 2D nuclear magnetic resonance spectroscopy and negative ESI-MS. RESULTS: The new 8-hydroxyapigenin 6-O-ß-D-apiofuranosyl-(1'''→6'')-C-ß-D-4C1-glucopyranoside was isolated from G. grandiflora for the first time in nature, along with schaftoside, luteolin 6-C-ß-D-4C1-glucopyranoside 8-methyl ether, apigenin 6-C-ß-D-4C1-glucopyranoside 8-methyl ether, isoorientin, isovitexin, 6-methoxyluteolin and hispidulin, as well as vicenin-2, vitexin, luteolin and apigenin, which were isolated from G. pulchella together with 6-methoxyluteolin. Furthermore, the AME of both species were found to be nontoxic to mice and exhibited significant anti-inflammatory and hepatoprotective activities in dose dependent manner. CONCLUSION: Current results shed light on the phenolic constituents of G. grandiflora and G. pulchella aerial parts and the safety of the AME of both species, in addition to their significant anti-inflammatory and hepatoprotective activities. Both plant species may be promising candidates for natural anti-inflammatory and hepatoprotective drugs. SUMMARY: Phytochemical investigation of Gaillardia grandiflora and Gaillardia pulchella 80% aqueous methanol extracts of the aerial parts led to the isolation of twelve compoundsThe new compound 8-hydroxyapigenin 6-O-ß-D-apiofuranosyl-(1''''→6'')-C-ß-D-4C1-glucopyranoside was isolated from G. grandiflora for the first time in natureSchaftoside, luteolin 6-C-ß-D-4C1-glucopyranoside 8-methyl ether, apigenin 6-C-ß-D-4C1-glucopyranoside 8-methyl ether, isoorientin, isovitexin, 6-methoxyluteolin and hispidulin were isolated from G. grandifloraVicenin-2, vitexin, luteolin, apigenin and 6-methoxyluteolin were isolated from G. pulchellaThe extracts of both species were nontoxic to mice up to 5 g/kg body weightBoth extracts exhibited significant anti-inflammatory and hepatoprotective activities in dose dependent manner Abbreviations used ALP Alkaline phosphatase; ALT Alanine aminotransferase; AME The 80% aqueous methanol extract of G. grandiflora or G. pulchella aerial parts; AST Aspartate aminotransferase; br d Broad doublet; Comp-PC Comparative paper chromatography; d Doublet; 2D-PC Two-dimensional paper chromatography; DMSO-d6 Deuterated dimethyl sulfoxide; G. Gaillardia; GPx Glutathione peroxidase; GRd Glutathione reductase; GSH glutathione; GST Glutathione-S-transferase; J Nuclear spin-spin coupling constant; m Multiplet; [M-H]- Molecular ion peak; MDA Malondialdehyde; m/z Mass/charge ratio; NO Nitric oxide; p Probability; PC Paper chromatography; Rf Retention flow; rpm Rotation per minute; s Singlet; SDE The ethanol extract of Scoparia dulcis; SE Standard error; SOD Superoxide dismutase; TMS Tetramethylsilane; λmax Maximum fluorescence emission wavelength.