- Heterologous biosynthesis of prenylated resveratrol and evaluation of antioxidant activity
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Prenylated stilbenoids are good candidates of nutraceuticals presented in food resources. The levels of natural prenylated stilbenoids are usually low. Biotransformation is a promising synthesis strategy to produce novel bioactive compounds. However, information regarding biosynthesis of prenylated stilbenoids is rare. In this work, prenyltransferase and geranyl diphosphate biosynthesis pathway were overexpressed in E. coli. Multiple prenyltransferase genes were tested and Ambp1 was found to be effective on resveratrol geranylation. The products were identified by mass spectrometry and nuclear magnetic resonance spectroscopy as 4-C-geranyl resveratrol (1) and 3-O-geranyl resveratrol (2, novel chemical). By optimization of culture conditions, a yield of 36.9% was achieved for the conversion to geranylated resveratrol from resveratrol. These two compounds demonstrated good antioxidant activities with IC50 values of 28.09 μM for 4-C-geranyl resveratrol and 403.88 μM for 3-O-geranyl resveratrol. The results were helpful for developing novel technique to produce prenylated phenolics.
- Bo, Shengtao,Chang, Sui Kiat,Jiang, Yueming,Yang, Bao,Zhou, Ting,Zhu, Hong
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- PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
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The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
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Paragraph 00348; 00356
(2021/12/08)
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- Total synthesis and dual PPARα/γ agonist effects of Amorphastilbol and its synthetic derivatives
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Amorphastilbol (APH-1), isolated from a Robinia pseudoacacia var. umbraculifer seed extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) α/γ agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki-Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2-APH-12 for PPAR agonist activity. APH-4 and APH-11 were effective PPARα/γ transcriptional activators, compared with APH-1. Therefore, we suggest that APH-4 and APH-11 are novel dual PPARα/γ agonists and are potentially useful for treating type 2 diabetes by enhancing glucose and lipid metabolism.
- Kim, Taejung,Lee, Woojung,Jeong, Kyu Hyuk,Song, Jung Ho,Park, Soon-Hye,Choi, Pilju,Kim, Su-Nam,Lee, Seokjoon,Ham, Jungyeob
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p. 4122 - 4126
(2012/07/03)
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- Chemoenzymatic syntheses of prenylated aromatic small molecules using Streptomyces prenyltransferases with relaxed substrate specificities
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NphB is a soluble prenyltransferase from Streptomyces sp. strain CL190 that attaches a geranyl group to a 1,3,6,8-tetrahydroxynaphthalene-derived polyketide during the biosynthesis of anti-oxidant naphterpin. Here we report multiple chemoenzymatic syntheses of various prenylated compounds from aromatic substrates including flavonoids using two prenyltransferases NphB and SCO7190, a NphB homolog from Streptomyces coelicolor A3(2), as biocatalysts. NphB catalyzes carbon-carbon-based and carbon-oxygen-based geranylation of a diverse collection of hydroxyl-containing aromatic acceptors. Thus, this simple method using the prenyltransferases can be used to explore novel prenylated aromatic compounds with biological activities. Kinetic studies with NphB reveal that the prenylation reaction follows a sequential ordered mechanism.
- Kumano, Takuto,Richard, Stephane B.,Noel, Joseph P.,Nishiyama, Makoto,Kuzuyama, Tomohisa
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p. 8117 - 8126
(2008/12/23)
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- METABOLITES FROM CHLOROPHORA EXCELSA: POSSIBLE INTERMEDIATES IN THE BIOGENESIS OF A PENTASUBSTITUTED STILBENE
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Key Word Index-Chlorophora excelsa; Moraceae; 2,4-dihydroxybenzaldehyde; 3,5-dihydroxybenzaldehyde; 3,5-dihydroxy-4-geranylbenzaldehyde; 3',4,5'-trihydroxy-4'-geranylstilbene; 2,3',4,5'-tetrahydroxy-4'-geranylstilbene; 2,3',4,5'-tetrahydroxystilbene; 3,4'-7-tri-O-methylquercitin; 2'-methoxy-3,4',7-tri-O-methylquercitin.Abstract-A series comprising substituted hydroxyl-geranylstilbenes, substituted benzenoid compounds and quercitin-type flavones were isolated and characterized from the acetone extract of the heartwood of Chlorophora excelsa.
- Malan, Elfranco,Swinny, Ewald,Ferreira, Daneel,Hall, Alida J.
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p. 2309 - 2312
(2007/10/02)
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