- Synthesis of xanthohumol and xanthohumol-d3from naringenin
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A six-step synthesis of xanthohumol (1a) and its d3-derivative (1b) from easily accessible naringenin is reported. The prenyl side chain was introduced by Mitsunobu reaction followed by the europium-catalyzed Claisen rearrangement and base-mediated opening of chromanone gave access to an α,β-conjugated ketone system. Compound1bwas used as an internal standard in stable isotope dilution assays of1ain two Polish beers.
- ?cianowski, Jacek,Andrusiak, Joanna,Budny, Marcin,Mylkie, Kinga,Wolan, Andrzej,Wysocka, Ma?gorzata
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p. 28934 - 28939
(2021/09/22)
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- Neuroregenerative Potential of Prenyl- And Pyranochalcones: A Structure-Activity Study
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Loss of neuronal tissue is a hallmark of age-related neurodegenerative diseases. Since adult neurogenesis has been confirmed in the human brain, great interest has arisen in substances stimulating the endogenous neuronal regeneration mechanism based on ad
- Aigner, Ludwig,Bieler, Lara,Couillard-Despres, Sebastien,Priglinger, Eleni,Riepl, Herbert M.,Urmann, Corinna
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supporting information
p. 2675 - 2682
(2021/10/12)
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- Synthesis and antiproliferative activity of minor hops prenylflavonoids and new insights on prenyl group cyclization
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Synthesis of minor prenylflavonoids found in hops and their non-natural derivatives were performed. The antiproliferative activity of the obtained compounds against some human cancer cell lines was investigated. Using xanthohumol isolated from spent hops
- Pop?o′ nski, Jaros?aw,Turlej, Eliza,Sordon, Sandra,Tronina, Tomasz,Bartma′ nska, Agnieszka,Wietrzyk, Joanna,Huszcza, Ewa
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- Chromane-like cyclic prenylflavonoids for the medical intervention in neurological disorders
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The present invention relates to certain chromane-like cyclic prenylflavonoids, in particular the compounds of formulae (I), (II) and (III) as described and defined herein, for use in the treatment or prevention of a neurological disorder, as well as their use in promoting neuronal differentiation, neurite outgrowth and neuroprotection.
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Page/Page column 39
(2017/01/23)
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- Analysis of the components of hard resin in hops (Humulus lupulus L.) and structural elucidation of their transformation products formed during the brewing process
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The resins from hops (Humulus lupulus L.), which add the bitter taste to beer, are classified into two main subfractions, namely, soft and hard resins. α- and β-Acids in soft resin and their transformation during the wort boiling process are well-studied; however, other constituents in resins, especially hard resin, have been unidentified. In this study, we identified humulinones and hulupones as soft-resin components, in addition to 4′-hydroxyallohumulinones and tricyclooxyisohumulones A and B as hard-resin components. These compounds are all oxidation products derived from α- and β-acids. We also investigated compositional changes in the hard resin during the wort boiling process, which has a significant effect on the taste of the beer, by using model boiling experiments. The major changes were identified to be isomerization of 4′-hydroxyallohumulinones into 4′- hydroxyallo-cis-humulinones, followed by decomposition into cis-oxyhumulinic acids. These findings will be helpful in systematically evaluating and optimizing the effect of the hard resin on beer quality.
- Taniguchi, Yoshimasa,Taniguchi, Harumi,Yamada, Makiko,Matsukura, Yasuko,Koizumi, Hideki,Furihata, Kazuo,Shindo, Kazutoshi
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p. 11602 - 11612
(2015/02/19)
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- Regio- and stereospecific prenylation of flavonoids by Sophora flavescens prenyltransferase
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Prenylflavonoids are valuable natural products that are widely distributed in plants. They often possess divergent biological properties, including phytoestrogenic, anti-bacterial, anti-tumor, and anti-diabetic activities. The reaction catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylflavonoids and often contributes to the structural diversity and biological activity of these compounds. However, only a few plant flavonoid prenyltransferases have been identified thus far, and these prenyltransferases exhibit strict substrate specificity and low catalytic efficiency. In this article, a flavonoid prenyltransferase from Sophora flavescens, SfFPT, has been identified that displays high catalytic efficiency with high regiospecificity acting on C-8 of structurally different types of flavonoid (i.e., flavanone, flavone, flavanonol, and dihydrochalcone, etc.). Furthermore, SfPFT exhibits strict stereospecificity for levorotatory flavanones to produce (2S)-prenylflavanones. This study is the first to demonstrate the substrate promiscuity and stereospecificity of a plant flavonoid prenyltransferase in vitro. Given its substrate promiscuity and high catalytic efficiency, SfFPT can be used as an environmentally friendly and efficient biological catalyst for the regio- and stereospecific prenylation of flavonoids to produce bioactive compounds for potential therapeutic applications. Copyright
- Chen, Ridao,Liu, Xiao,Zou, Jianhua,Yin, Yunze,Ou, Bin,Li, Jianhua,Wang, Ruishan,Xie, Dan,Zhang, Peicheng,Dai, Jungui
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p. 1817 - 1828
(2013/07/19)
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- An efficient synthesis of the phytoestrogen 8-prenylnaringenin from isoxanthohumol with magnesium iodide etherate
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Xanthohumol was isolated from supercritical carbon dioxide-spent hop and transformed into isoxanthohumol. The demethylation of isoxanthohumol with the best yield 93% occurred when MgI2 etherate in anhydrous THF was applied. Salts such as MgBrs
- Anio?, Miros?aw,Szymańska, Katarzyna,Zo?nierczyk, Anna
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p. 9544 - 9547
(2008/12/22)
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- METHOD FOR PRODUCING NARINGENIN DERIVATIVES FROM XANTHOHUMOL
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The invention relates to an efficient method for producing naringenin derivatives from xanthohumol or derivatives thereof. The method comprises, in particular, the production of isoxanthohumol, for example, even in an enantiomer-enriched form, from xanthohumol and subsequently demethylating isoxanthohumol according to specific procedures while obtaining corresponding naringenin derivatives such as 8-prenylnaringenin.
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Page/Page column 9
(2008/06/13)
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- An efficient synthesis of the phytoestrogen 8-prenylnaringenin from xanthohumol by a novel demethylation process
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8-Prenylnaringenin, a flavonoid, is the strongest known phytoestrogen (plant derived estrogen mimic) used in phytomedicinal applications. Starting from xanthohumol a byproduct of hops-extraction, 8-prenylnaringenin can be synthesized via isoxanthohumol. Of various demethylation procedures tested, the best yield (92%) is obtained by treatment with scandium trifluoromethanesulfonate and potassium iodide without any need of protection. The demethylation with AlBr3/collidine and of the TIPS protected isoxanthohumol provides good results too.
- Wilhelm, Heike,Wessjohann, Ludger A.
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p. 6961 - 6966
(2007/10/03)
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- Production of hop extracts having oestrogenic and antiproliferative bioactivity
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The invention relates to a method for the production of a hop extract enriched in prenylated flavonoids or derivatives thereof, whereby the method comprises the steps of subjecting a hop product to an isomerisation reaction in the presence of an amount of a base and to at least one extraction.
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Page/Page column 7; 8
(2008/06/13)
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- Remedies
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The present invention provides a therapeutic agent or prophylactic agent for a disease requiring enhancement for growth factor production and a food, beverage or feed for enhancing growth factor production, each comprising as an effective ingredient: poly
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- Prenylflavonoids from Humulus lupulus
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Five flavonoids were isolated from the resin part of the female inflorescences of Humulus lupulus, together with four known hop flavonoids, i.e. xanthohumol, 2',4',6',4-tetrahydroxy-3'-C-prenylchalcone, iso- xanthohumol and 6-prenylnaringenin. The new hop
- Stevens, Jan F.,Ivancic, Monika,Hsu, Victor L.,Deinzer, Max L.
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p. 1575 - 1585
(2007/10/03)
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- Demethylxanthohumol: Isolation from Hops and Cyclisation to Flavanons
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Demethylxanthohumol (1) was isolated together with xanthohumol (2) from freshly harvested strobili of hops (humulus lupulus L.).Structure proof of 1 is based on spectroscopic data and on the transformation of 1 and 2 into trimethylxanthohumol (3).Treatmen
- Haensel, Rudolf,Schulz, Jutta
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