Flavonoids and a naphthopyranone from Eriocaulon ligulatum and their mutagenic activity

A new acylated flavonoid, 6,4'-dimethoxyquereetin-3-O-beta-D-6 ''[3,4,5-trihydroxy (E)-cinnamoyl]glucopyranoside, and a naphthopyranone dimer, named eriocauline, together with 2 other known flavonoids, 6-methoxyapigenin-7-O-beta-D-glucopyranoside and 6-methoxyapigenin-7-O-beta-D-allopyranoside, have been isolated from the capitulae of Eriocaulon ligulatum. The compounds were identified using spectroscopic methods (HR-ESI-MS, and 1-D and 2-D NMR). The methanol extract exhibited mutagenic activity in the Salmonella/microsome assay, in strains TA100, TA97a and TA102 and for dichloromethane extract tested in strain TA98.

In vitro basal and metabolism-mediated cytotoxicity of flavonoids

The purpose of this study was to compare the basal cytotoxicity and metabolism-mediated cytotoxicity of kaempferol, quercetin and rutin. McCoy cells were exposed to various concentrations of the flavonols with and without the S9 system. The neutral red uptake assay was used to determine viability after 24 h at 35-37 degrees C. Dose-response curves were established for each flavonol in the presence and absence of external metabolizing systems. Kaempferol and quercetin were cytotoxic and provoked a dose-dependent decrease in cell viability, without the S9 system. The hepatic S9 microsomal fraction metabolized these compounds to less cytotoxic metabolites. In contrast, rutin at 500 mu g/ml failed to produce any overt signs of toxicity in either assay. (c) 2005 Elsevier Ltd. All rights reserved.

In Vitro Phytotoxicity and Antioxidant Activity of Selected Flavonoids

The knowledge of flavonoids involved in plant-plant interactions and their mechanisms of action are poor and, moreover, the structural characteristics required for these biological activities are scarcely known. The objective of this work was to study the possible in vitro phytotoxic effects of 27 flavonoids on the germination and early radical growth of Raphanus sativus L. and Lepidium sativum L., with the aim to evaluate the possible structure/activity relationship. Moreover, the antioxidant activity of the same compounds was also evaluated. Generally, in response to various tested flavonoids, germination was only slightly affected, whereas significant differences were observed in the activity of the various tested flavonoids against radical elongation. DPPH test confirms the antioxidant activity of luteolin, quercetin, catechol, morin, and catechin. The biological activity recorded is discussed in relation to the structure of compounds and their capability to interact with cell structures and physiology. No correlation was found between phytotoxic and antioxidant activities.

Antiproliferative Activity of Three Methoxylated Flavonoids Isolated from Zeyheria montana Mart. (Bignoniaceae) Leaves

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Flavonoids and antiulcerogenic activity from Byrsonima crassa leaves extracts

Byrsonima crassa Niedenzu (IK) (Malpighiaceae) is used in Brazilian folk medicine for the treatment of diseases related mainly to gastric ulcers. In this study, we evaluated the potential antiulcerogenic effect of three different extracts obtained from the leaves of Byrsonima crassa namely hydromethanolic (80% MeOH), methanolic (MeOH) and chloroformic extracts (CHCl3). The oral administration (250, 500 and 1000 mg/kg) of all the extracts reduced the formation of lesions associated with HCl/ethanol administration in mice. The 80% MeOH extract significantly reduced the incidence of gastric lesions by 74, 78 and 92% at doses of 250,500 and 1000 mg/kg, respectively (P < 0.01). The MeOH extract reduced the ulceration by 93 and 99% only at the doses of 500 and 1000 mg/kg (P < 0.01). The lower gastroprotective action (69%) was observed when animals were treated with CHCl3 extract at the dose of 1000 mg/kg (P < 0.01). Phytochemical investigation of Byrsonima crassa afforded five known substances: quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-alpha-L-arabinopyranoside, the biflavonoid amentoflavone, (+)-catechin and (-)-epicatechin. The presence of these phenolic compounds may probably explain the antiulcerogenic effect of the extracts of Byrsonima crassa leaves. (C) 2004 Elsevier B.V.. All rights reserved.

Application of preparative high-speed counter-current chromatography for the separation of flavonoids from the leaves of Byrsonima crassa Niedenzu (IK)

The methanolic extract of the leaves of the medicinal plant Byrsonima crassa (Malpighiaceae) contain flavonoids with antioxidant activity. They were separated in a preparative scale using high-speed counter-current chromatography. The optimum solvent system used was composed of a mixture of ethyl acetate-n-propanol-water (140:8:80 (v/v/v)) and led to a successful separation between monoglucosilated flavonoids (quercetin-3-O-alpha-L-arabinoside, quercetin-3-O-beta-D-galactoside) and the biflavonoid amentoflavone in only 3.5 h. The purities of quercetin-3-O-alpha-L-arabinoside (95 mg), quercetin-3-O-beta-D-galactoside (16 mg) and the biflavonoid amentoflavone (114 mg) were all isolated at purity over 95%. Identification was performed by H-1 NMR, C-13 NMR and UV analyses. (C) 2004 Published by Elsevier B.V.

Effect of Mouriri pusa tannins and flavonoids on prevention and treatment against experimental gastric ulcer

Aim of the study: Mouriri pusa, popularly known as manapuca or jaboticaba do mato, is a plant from Brazilian cerrado that has been found to be commonly used in the treatment of gastrointestinal disturbs in its native region. The present work was carried out to investigate the effect of tannins (TF) and flavonoids (FF) fractions from Mouriri pusa leaves methanolic extract on the prevention and cicatrisation process of gastric ulcers, and also evaluate possible toxic effects.Materials and methods: The following protocols were taken in rats: acute assay, in which ulcers were induced by oral ethanol after pre-treatment with the fractions; and 14 days treatment assay, in which ulcers were treated for 14 days after induction by local injection of acetic acid.Results: In the acute model, treatment with either, TF (25 mg/kg) or FF (50 mg/kg), was able to reduce lesion area, showing gastroprotective effect. In addition, FF proved itself anti-inflammatory by reducing COX-2 levels. In acetic acid model, both fractions exhibited larger ulcers' regenerative mucosa, indicating cicatrisation enhancement. FF group also showed augmented cell proliferation, anti-inflammatory action and enhanced angiogenesis as well as increased mucus secretion. Moreover, concerning the toxicity parameters analyzed, no alteration in the fractions groups was observed.Conclusions: Tannins and flavonoids from Mouriri pusa provide beneficial effects against gastric ulcers with relative safety. (C) 2010 Elsevier B.V. All rights reserved.

Fast Screening for Antioxidant Properties of Flavonoids from Pterogyne nitens Using Electrochemical Methods

A fast, low-cost, convenient, and especially sensitive voltammetric screening approach for the study of the antioxidant properties of isoquercitrin and pedalitin from Pterogyne nitens is suggested in this work. These flavonoids were investigated for their redox properties using cyclic voltammetry in nonaqueous media using N,N-dimethylformamide and tetrabutylammonium tetrafluorborate as the supporting electrolyte, a glassy carbon working electrode, AglAgCl reference electrode, and Pt bare wire counter electrode. The comparative analysis of the activity of rutin has also been carried out. Moreover, combining HPLC with an electrochemical detector allowed qualitative and quantitative detection of micromolecules (e.g., isoquercitrin and pedalitin) that showed antioxidant activities. These results were then correlated to the inhibition of p-carotene bleaching determined by TLC autographic assay and to structural features of the flavonoids.

Dimeric alkaloids and flavonoids from Aristolochia ridicula

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

An LC-DAD Fingerprinting Method for Alkaloids, Flavonoids and Styrylpyrones from Cryptocarya mandioccana

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

High-Performance Liquid Chromatographic Quantification of Flavonoids in Eriocaulaceae Species and Their Antimicrobial Activity

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Mutagenicity of Flavonoids Assayed by Bacterial Reverse Mutation (Ames) Test

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)

Preparative separation of flavonoids from the medicinal plant Davilla elliptica St. Hill. by high-speed counter-current chromatography

Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)