- PRUNETIN 5-O-β-D-GLUCOPYRANOSIDE, AN ISOFLAVONE FROM THE PEDUNCLE OF PRUNUS AVIUM AND P. CERASUS
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Prunetin 5-glucoside was isolated from cherry peduncle Prunus avium and P. cerasus.The structure was fully assigned on the basis of NMR evidence.It is the second 5-O-glycosylated isoflavonoid to be reported. Key Word Index-Prunus avium; P. ceraus; Rosaceae; cherry; peduncle; prunetin 5-glucoside; isoflavone.
- Khalid, S. A.,Gellert, M.,Szendrei, K.,Duddeck, Helmut
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- Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids
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Methylation of free hydroxyl groups is an important modification for flavonoids. It not only greatly increases absorption and oral bioavailability of flavonoids, but also brings new biological activities. Flavonoid methylation is usually achieved by a specific group of plant O-methyltransferases (OMTs) which typically exhibit high substrate specificity. Here we investigated the effect of several residues in the binding pocket of the Clarkia breweri isoeugenol OMT on the substrate scope and regioselectivity against flavonoids. The mutation T133M, identified as reported in our previous publication, increased the activity of the enzyme against several flavonoids, namely eriodictyol, naringenin, luteolin, quercetin and even the isoflavonoid genistein, while a reduced set of amino acids at positions 322 and 326 affected both, the activity and the regioselectivity of the methyltranferase. On the basis of this work, methylated flavonoids that are rare in nature were produced in high purity.
- Tang, Qingyun,Vianney, Yoanes M.,Weisz, Klaus,Grathwol, Christoph W.,Link, Andreas,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.
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p. 3721 - 3727
(2020/06/02)
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- Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones
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In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.
- Lu, Tzy-Ming,Ko, Horng-Huey,Ng, Lean-Teik,Hsieh, Yen-Pin
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p. 963 - 979
(2015/06/25)
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- Synthesis and cytotoxic activity of genistein derivatives
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A series of genistein derivatives was prepared and tested in vitro against leukocythemia (HL-60), colorectal adenocarcinoma (HT-29), and human gastric adenocarcinoma (SGC-7901) cell lines. Among these derivatives, 4′,5-di-n-octoxy-7-gem-difluoromethylenegenistein, 9f, had the strongest activity against HL-60, HT-29, and SGC-7901 cells.[Figure not available: see fulltext.]
- Zheng, Xing,Yao, Xu,Liu, Yunmei,Zheng, Zitong,Cao, Jianguo,Liao, Duanfang
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experimental part
p. 1296 - 1306
(2011/10/12)
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- Unsaturated genistein disaccharide glycoside as a novel agent affecting microtubules
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Genistein, due to its recognized chemopreventive and antitumor potential, is a molecule of interest as a lead compound in drug design. While multiple molecular targets for genistein have been identified, so far neither for this isoflavonoid nor for its na
- Rusin, Aleksandra,Gogler, Agnieszka,Glowala-Kosinska, Magdalena,Bochenek, Daria,Gruca, Aleksandra,Grynkiewicz, Grzegorz,Zawisza, Jadwiga,Szeja, Wieslaw,Krawczyk, Zdzislaw
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body text
p. 4939 - 4943
(2010/03/02)
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- Genistein derivatives as selective estrogen receptor modulators: Sonochemical synthesis and in vivo anti-osteoporotic action
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Genistein derivatives were synthesized from genistein through a facile sonochemical approach in high yields. The bioassay was performed on ovariectomized (OVX) rats in terms of bone mineral density (BMD) and the weight of bone ash (WBA) to lead to the discovery of eight novel genistein-based selective estrogen receptor modulators. Attention to the structure-activity relationship disclosed that the newly introduced 2-hydroxyethylthio scaffolds were essential for the anti-osteoporotic activity. Moreover, the anti-osteoporotic action of genistein, deprivable by methylation, could be restored and enhanced by subsequent sulfonation. The most promising compound was 4′,5,7-tri[3-(2-hydroxyethylthio)propoxy]isoflavone, displaying 24% (or 8%) increment in BMD and 31% (or 11%) increase in WBA of the femora relative to those discerned with the OVX (or genistein) group. Acute toxicity test showed that none of the active compounds was acutely toxic.
- Wang, Shi F.,Jiang, Qing,Ye, Yong H.,Li, Yang,Tan, Ren X.
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p. 4880 - 4890
(2007/10/03)
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- COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH
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The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.
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Page/Page column 17
(2010/11/30)
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- FLAVONOID 5-GLUCOSIDES FROM PRUNUS CERASUS BARK AND THEIR CHARACTERISTIC WEAK GLYCOSIDIC BONDING
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Pinostrobin 5-glucoside, a novel flavanone glycoside, was isolated from the bark of Prunus cerasus.As it was not found in P. avium, the substance is useful to distinguish these two species.Apigenin 5-glucoside, genkwanin 5-glucoside and neosakuranin were also isolated from the bark of P. cerasus.They occur in both species as minor components.These 5-glucosides together with genistein 5-glucoside, prunetin 5-glucoside, sakuranin, tectochrysin 5-glucoside and luteolin 5-glucoside were hydrolysed in malic acid.The isoflavone and flavone 5-glucosides were shown to be hydrolysed more rapidly than the flavanone 5-glucosides, whereas no hydrolysis was observed with the corresponding 7-glucosides under the same conditions.The chalcone 2'-glucoside neosakuranin was transformed at first to the corresponding flavanone 5-glucoside, which was hydrolysed thereafter. Key Word Index - Prunus cerasus; Prunus avium; Rosaceae; bark; pinostrobin 5-glucoside; flavonoid 5-glucosides; hydrolysis.
- Geibel, Martin,Feucht, Walter
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p. 1519 - 1521
(2007/10/02)
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- TWO ISOFLAVONE GALACTOSIDES FROM DALBERGIA SPINOSA
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Key Word Index-Dalbergia spinosa; Leguminosae; leaves; prunetin 4'-O-β-D-galactoside; 7-methyltectorigenin 4'-O-β-D-galactoside; stem-bark; known isoflavones.Abstract-The chemical examination of the leaves and steam-bark of Dalbergia spinosa has yielded, in addition to a number of known isoflavones, two new isoflavone galactosides, prunetin 4'-O-β-D-galactoside and 7-methyltectorigenin 4'-O-β-D-galactoside.
- Narayanan, Venkateswaran,Nagarajan, Natesan Shanmugan
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p. 2364 - 2365
(2007/10/02)
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- Studies on Zoospore-Attracting Activity. I. Synthesis of Isoflavones and Their Attracting Activity to Aphanomyces euteiches Zoospore
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Prunetin (2) and its derivatives were synthesized in order to study the relationship between structure and attracting activity to Aphanomyces euteiches zoospore.All of the derivatives (1, 2, 4 and 6), which had a hydroxyl group at the C-5 position in the isoflavone, showed attracting activity, but the methyl ether derivatives (3, 5, 7 and 8) do not have or have very weak attracting activity.The isoflavones (1, 2, and 4) with strong attracting activity also had estrogenic activity.Keywords - isoflavone; prunetin; genistein; biochanin A; 5-methylgenistein; 5-hydroxy-4',7-dimethoxyisoflavone; Aphanomyces euteiches; zoospore; attracting activity; estrogenic activity
- Sekizaki, Haruo,Yokosawa, Ryozo
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p. 4876 - 4880
(2007/10/02)
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