3-methylquercetin and caffeic-acid

During their domestication process, the species of the genus Opuntia lose their ability to survive in the wild. Presence and concentration of secondary metabolites which play a role in the interaction with their surroundings are modified but without an identifiable pattern. A domestication gradient based on morphological characteristics has been previously described for the species in the Opuntia genus. Secondary metabolites are a diverse group of bioactive compounds that relate to a species evolution, both in their natural and artificial (domestication process) selection environments. In addition, these compounds are associated with plant resistance to stress when growing in the wild. A comprehensive characterization of secondary metabolite profiles in the Opuntia genus that accounts for the genotypic differences related to the degree of domestication has not previously been conducted. This study evaluated the phytochemical composition of young cladodes from fifteen variants, of O. ficus-indica, O. albicarpa Sheinvar, and O. megacantha Salm-Dyck, identified as species with a highly advanced, advanced and intermediate degree of domestication, respectively, and O. hyptiacantha A. Web, and O. streptacantha Lem. identified as wild-intermediate and wild species. Analyses were carried out using a HPLC-diode array detection technique. Out of the 13 identified and quantified phenolic molecules and terpenoids, only the caffeic, ferulic and syringic acids, and the terpenoid β-amyrin were present in all variants. The flavonoid luteolin was absent in all five species. Gallic, vallinic, p-hydroxybenzoic, chlorogenic and p-coumaric acids were only present in 53-87% of variants; flavonoids quercetin, isorhamnetin, rutin and apigenin in 47-87% of the variants. Both, oleanolic acid and peniocerol, were present only in 60% of variants. Isorhamnetin was absent in O. hyptiacantha and quercetin in O. streptacntha. Differences and similarities in the secondary metabolites content showed no recognizable trend relating to the degree of domestication across the species in this genus.

Topics: Apigenin; Caffeic Acids; Chlorogenic Acid; Chromatography, High Pressure Liquid; Coumaric Acids; Domestication; Flavonoids; Gallic Acid; Hydroxybenzoates; Oleanolic Acid; Opuntia; Quercetin; Rutin; Sterols; Terpenes; Vanillic Acid

New types of two-dimensional (2D) boron nitride (BN) were developed as a 2D scaffold material. After modification with ternary deep eutectic solvents (DES, ChCl-caffeic acid-ethylene glycol), the processed BN was applied to the preparation of magnetic molecularly imprinted polymers (MMIPs). In the polymerization of MMIPs, DESs and hydrophobic Fe3O4 magnetite were applied as the functional monomer and magnetically susceptible component, respectively. A 2D ellipsoid material was formed successfully by polymerization on the surface of the processed BN. The proposed 2D-MMIPs were characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, scanning electron microscopy, and nitrogen sorption analysis techniques. The surface area of the 2D-MMIPs was increased using eco-friendly chemicals. The proposed 2D-MMIPs had a 2D oblate structure and a large surface area. The 2D-MMIPs were used for the preconcentration of flavonoids from Ginkgo biloba leaf extracts. High performance liquid chromatography-ultraviolet analysis revealed that the 2D-MMIPs have higher recoveries for the flavonoids (quercetin 96.8%, isorhamnetin 93.6% and kaempferol 94.8%) in Ginkgo biloba leaves than common MMIPs.

Topics: Adsorption; Boron Compounds; Caffeic Acids; Choline; Ethylene Glycol; Flavonoids; Ginkgo biloba; Kaempferols; Magnetite Nanoparticles; Methacrylates; Molecular Imprinting; Plant Leaves; Polymerization; Polymers; Quercetin; Solvents

Polyphenols are phytochemicals that possess antioxidant and anti-inflammatory properties and improve glucose metabolism in animal experiments, although data from prospective epidemiologic studies examining polyphenol intakes in relation to type 2 diabetes (T2D) risk are inconsistent.. We examined urinary excretion of select flavonoid and phenolic acid metabolites, as biomarkers of intake, in relation to T2D risk.. Eight polyphenol metabolites (naringenin, hesperetin, quercetin, isorhamnetin, catechin, epicatechin, caffeic acid, and ferulic acid) were quantified in spot urine samples by liquid chromatography/mass spectrometry among 1111 T2D case-control pairs selected from the Nurses' Health Study (NHS) and NHSII.. Higher urinary excretion of hesperetin was associated with a lower T2D risk after multivariate adjustment: the OR comparing top vs. bottom quartiles was 0.68 (95% CI: 0.49, 0.96), although a linear trend was lacking (P = 0.30). The other measured polyphenols were not significantly associated with T2D risk after multivariate adjustment. However, during the early follow-up period [≤ 4.6 y (median) since urine sample collection], markers of flavanone intakes (naringenin and hesperetin) and flavonol intakes (quercetin and isorhamnetin) were significantly associated with a lower T2D risk. The ORs (95% CIs) comparing extreme quartiles were 0.61 (0.39, 0.98; P-trend: 0.03) for total flavanones and 0.55 (0.33, 0.92; P-trend: 0.04) for total flavonols (P-interaction with follow-up length: ≤ 0.04). An inverse association was also observed for caffeic acid during early follow-up only: the OR was 0.52 (95% CI: 0.32, 0.84; P-trend: 0.03). None of these markers was associated with T2D risk during later follow-up. Metabolites of flavan-3-ols and ferulic acid were not associated with T2D risk in either period.. These results suggest that specific flavonoid subclasses, including flavanones and flavonols, as well as caffeic acid, are associated with a lower T2D risk in relatively short-term follow-up but not during longer follow-up. Substantial within-person variability of the metabolites in single spot urine samples may limit the ability to capture associations with long-term disease risk.

Topics: Adult; Aged; Aged, 80 and over; Caffeic Acids; Case-Control Studies; Catechin; Coumaric Acids; Diabetes Mellitus, Type 2; Female; Flavanones; Follow-Up Studies; Hesperidin; Humans; Hydroxybenzoates; Middle Aged; Nutrition Assessment; Polyphenols; Prospective Studies; Quercetin; Risk Factors; Surveys and Questionnaires

To investigate the chemical constituents from Commelina communis, fifteen compounds were separated and purified by silica gel, Sephadex LH-20, and ODS column chromatography, and semi-preparative HPLC. By analyses of NMR and MS data as well as their physical and chemical properties, the structures of these compounds were identified as chrysoeriol-7-O-beta-D-glucoside( 1), methyl gallate(2), p-coumaric acid(3), protocatechuic acid(4), caffeic acid(5), p-hydroxybenzoic acid(6), 2-phenethyl-beta-D-gly-cosidase(7) , rhaponticin(8) , (7S, 8R) -dihydrodehydrodiconiferyl alcohol-9-O-beta-D-glucoside (9), isovitexin (10) , isofurcatain (11), isorhamnetin-3-O-beta-D-glucoside(12) , quercetin-3-O-alpha-L-rhamnoside (13) , isoquercitrin (14) , and 1, 2-dihydro-6, 8-dime-thoxy-7-1-(3, 5-dimethoxy-4-hydroxyphenyl) -N1, N2-bis-[2-( 4-hydroxyphenyl) ethyl] -2, 3-naphthalene dicarboxamide (15). Compounds 2, 5-9, 11, 13 were obtained from the genus Commelina for the first time.

Topics: Caffeic Acids; Chromatography, High Pressure Liquid; Commelina; Glucosides; Hydroxybenzoates; Quercetin

The aqueous and ethanol extracts from the leaves of Gochnatia polymorpha and further fractions obtained from the latter extract using solvents with increasing polarity, including its aqueous residue and the amino acid, 4-hydroxy-N-methyl-proline were investigated by carrageenin-induced pedal oedema formation. It was shown that the aqueous and ethanol extracts and the ethyl acetate fraction demonstrated significant antiinflammatory activity. The chemical investigation of the latter fraction revealed the presence of caffeic acid, chlorogenic acid, 3-0-methylquercetin, hyperosid and rutin. The amino acid 4-hydroxy-N-methyl-proline, a nonprotein amino acid that has not been reported before in the Asteraceae was isolated as a major compound and identified by spectroscopic methods.

Topics: Analgesics; Animals; Anti-Inflammatory Agents; Antioxidants; Antiviral Agents; Brazil; Caffeic Acids; Chlorogenic Acid; Chromatography, Gel; Chromatography, Thin Layer; Edema; Flavonols; Plant Extracts; Plant Leaves; Plants, Medicinal; Proline; Quercetin; Rats; Rutin