Flavonoïdes prénylés et perméabilité membranaire

Barron, Denís; Balland, C.; Possety, Françoise; Ravanel, Patrick; Desfougères, Aline

doi:10.1080/12538078.1996.10515348

Cited by 20 publications

(7 citation statements)

References 17 publications

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“…Prenylflavonoids are a minor class of flavonoids characterized by a prenyl side chain attached to the aromatic benzopyrene skeleton (Heide 2009) and have a relatively narrow distribution in the plant kingdom (Botta et al 2005). This prenyl moiety increases the lipofilicity and confers to the flavonoid molecule a strong affinity to biological membranes, displaying a series of interesting biological activities (Barron et al 1996).…”

Section: Introductionmentioning

confidence: 99%

Fast Screening Method to Determine Hop’s Phytoestrogens in Beer

et al. 2010

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A novel, fast, and simple method to determine three phytoestrogens [xanthohumol (XN), isoxanthohumol (IXN), and 8-prenylnaringenin (8PN)] in beer samples by high-performance liquid chromatography with diode-array detection has been developed. The selected method involves purification by solid phase extraction and separation achieved on a C 18 column by using a gradient elution program. This consists of a mixture of acetonitrile, water, and methanol (all of them with 1% of acetic acid) at a flow ratio of 1 mL/min. The detection wavelengths were set at 370 nm for XN and 280 nm for IXN and 8PN. Average analyte recoveries were higher than 75% with relative standard deviations lower than 5%. The detection limits were between 0.01 and 0.08 mg/L, and the quantitation limits were between 0.02 and 0.15 mg/L. The method has been validated and applied to the analysis of several types of commercial beers obtained from local markets, where results showed the presence of IXN and 8PN in most of the samples and the absence of XN. Thus, the presented method gives to brewing chemists a validated, reliable, fast, and affordable analytical tool to identify and quantify the three most important hop's prenylflavonoids in beer.

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Section: Introductionmentioning

confidence: 99%

Fast Screening Method to Determine Hop’s Phytoestrogens in Beer

et al. 2010

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“…4−6 It is hypothesized that the prenyl side chain improves the membrane permeability of prenylated flavonoids, which consequently confers enhanced biological activities. 1,7−10 As a result of their health benefits, prenylated flavonoids are currently investigated as potential biopharmaceuticals and functional foods. Last but not least, prenylated (iso)flavonoids have also received interest because of their promising antimicrobial activity, 11−14 suggesting that they might also be used as food preservatives or antibiotics in clinical applications.…”

Section: Introductionmentioning

confidence: 99%

Toward Developing a Yeast Cell Factory for the Production of Prenylated Flavonoids

Levisson

Araya‐Cloutier

Bruijn

et al. 2019

J. Agric. Food Chem.

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Prenylated flavonoids possess a wide variety of biological activities, including estrogenic, antioxidant, antimicrobial, and anticancer activities. Hence, they have potential applications in food products, medicines, or supplements with health-promoting activities. However, the low abundance of prenylated flavonoids in nature is limiting their exploitation. Therefore, we investigated the prospect of producing prenylated flavonoids in the yeast Saccharomyces cerevisiae. As a proof of concept, we focused on the production of the potent phytoestrogen 8-prenylnaringenin. Introduction of the flavonoid prenyltransferase SfFPT from Sophora flavescens in naringenin-producing yeast strains resulted in de novo production of 8-prenylnaringenin. We generated several strains with increased production of the intermediate precursor naringenin, which finally resulted in a production of 0.12 mg L–1 (0.35 μM) 8-prenylnaringenin under shake flask conditions. A number of bottlenecks in prenylated flavonoid production were identified and are discussed.

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“…Barron and co-workers observed that the addition of hydrophobic groups increases the lipophilicity of molecules, therefore enhancing the cytotoxicity activity [ 12 ]. Based on this observation, allylation and acetonidation reactions were performed on soyauxinium nitrate ( 5 ), edulinine ( 3 ), ribalinine ( 4 ) and aborinine ( 6 ) which led to six semi-synthetic derivatives, among which five (compounds 3a, 3b, 4b, 5a and 6a ) are reported here for the first time ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

et al. 2022

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The chemical investigation of the total alkaloid extract (TAE) of the stem bark of Araliopsis soyauxii (Rutaceae) afforded an unreported indolopyridoquinazoline (compound 1) along with nine previously known alkaloids 2-10. In addition, six semi-synthetic derivatives 3a-c, 4b, 5a and 6a were prepared by allylation and acetonidation of soyauxinium nitrate (5), edulinine (3), ribalinine (4) and arborinine (6). The structures and spectroscopic data of five of them are reported herein for the first time. The suggested mechanism for the formation of the new N-allylindolopyridoquinazoline 5a is presented. The structures of natural and derived compounds were determined employing extensive NMR and MS techniques. The absolute configuration of stereogenic centers in compounds 2-4 were determined using NOESY technique and confirmed by the single-crystal X-ray diffraction (SC-XRD) technique. The use of SC-XRD further enabled us to carry out a structural revision of soyauxinium chloride recently isolated from the same plant to soyauxinium nitrate (5). The TAE, fractions, compounds 1-7 and 9, and semi-synthetic derivatives 3a-c, 4b, 5a and 6a were evaluated for their cytotoxic activity towards the cervix carcinoma cell line KB-3-1. No significant activity was recorded for most of the compounds except for 9, which showed moderate activity against the tested cancer cell lines.

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Flavonoïdes prénylés et perméabilité membranaire

Cited by 20 publications

References 17 publications

Fast Screening Method to Determine Hop’s Phytoestrogens in Beer

Fast Screening Method to Determine Hop’s Phytoestrogens in Beer

Toward Developing a Yeast Cell Factory for the Production of Prenylated Flavonoids

Soyauxinine, a New Indolopyridoquinazoline Alkaloid from the Stem Bark of Araliopsis soyauxii Engl. (Rutaceae)

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