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1.
Dihydrochalcones are plant secondary metabolites comprising molecules of significant commercial interest as antioxidants, antidiabetics, or sweeteners. To date, their heterologous biosynthesis in microorganisms has been achieved only by precursor feeding or as minor by-products in strains engineered for flavonoid production. Here, the native ScTSC13 was overexpressed in Saccharomyces cerevisiae to increase its side activity in reducing p-coumaroyl-CoA to p-dihydrocoumaroyl-CoA. De novo production of phloretin, the first committed dihydrochalcone, was achieved by co-expression of additional relevant pathway enzymes. Naringenin, a major by-product of the initial pathway, was practically eliminated by using a chalcone synthase from barley with unexpected substrate specificity. By further extension of the pathway from phloretin with decorating enzymes with known specificities for dihydrochalcones, and by exploiting substrate flexibility of enzymes involved in flavonoid biosynthesis, de novo production of the antioxidant molecule nothofagin, the antidiabetic molecule phlorizin, the sweet molecule naringin dihydrochalcone, and 3-hydroxyphloretin was achieved.  相似文献   
2.
Trunk wood of Iryanthera laevis Markgr. (Myristicaceae) contains 2′,4′-dihydroxy- 4,6′dimethoxydihydrochalcone, three 2′-hydroxy-4′,5′-methylenedioxyflavans with differently substituted A-rings (7-OH-6,8-diMe; 7-OH-5,8-diMe; 5-OH-7-OMe-6,8-diMe) and 1-(2′-hydroxy-4′-methoxy-5′-methylphenyl)-3(2″-hydroxy-4″,5″-methylenedioxphenyl)- propane, as well as three additional known diarylpropanes.  相似文献   
3.
The potential of UV spectrophotometry and an aluminium chloride (AlCl(3)) colorimetric method to determine the dihydrochalcone (DHC) and mangiferin contents of green rooibos and honeybush (C. genistoides) extracts, respectively, was investigated. The DHC content of rooibos water extracts, determined using UV spectroscopy, correlated with the sum of the aspalathin and nothofagin contents as quantified using HPLC (r = 0.98). A correlation coefficient of 0.91 was obtained when correlating the mangiferin content of C. genistoides methanol extracts, determined by the AlCl(3) colorimetric method, with the results obtained by HPLC. Using the linear equations from the correlations it was possible to predict the DHC and mangiferin contents of extracts from the respective spectrophotometric measurements to a reasonable accuracy as an alternative to HPLC. The total polyphenol (TP) content of rooibos water extracts can also be determined using UV spectrophotometry and aspalathin as a standard (r = 0.99) as an alternative to the Folin-Ciocalteau method. The TP content of rooibos extracts correlated (r = 0.99) with its total antioxidant activity (TAA) as determined with the ABTS radical cation scavenging assay, but the TP content of C. genistoides water extracts is not a good indication of their TAA (r = 0.27). The aspalathin content of rooibos extracts correlated with their TAA (r = 0.96), but the mangiferin content of honeybush water extracts only gave a moderate correlation with their TAA (r = 0.75).  相似文献   
4.
We developed a strategy for determination and quantification of glycosyl flavonoids using liquid chromatography-triple quadrupole mass spectrometry with neutral loss scan at 15 and 30eV collision energy in the positive ion mode. The fragmentation patterns of glycosyl flavonoids at 15 and 30eV showed that fragmentation of sugar moiety depended on the type of glycosidic bond to aglycone, the site of C-glycosylation, and the type of aglycone. C-Glycosyl dihydrochalcones especially stood out because they produced [M+H-162](+) even at 15eV such as O-glycoside in spite of C-glycoside. C-Glycosides were classified according to (i) the intensity ratio A of [M+H-150](+) to [M+H-120](+) at 30eV and (ii) the intensity ratio B of [M+H-120](+) at 15eV to one at 30eV. The 8-C-glycosides were A<1 and B<1, the 6-C-glycosides were A>1 and B<1, and the C-glycosyl dihydrochalcones were A>1 and B>1. Therefore, the intensity ratios of the neutral loss scan of 120 and 150Da at 30eV and those of 120, 162, and 308Da at 15eV allowed sequential distinction among these three types of C-glycosides as well as between O- and C-glycosides. Our method was applied for analysis of Rooibos tea, and the identified glycosides could be quantified specifically by the selected reaction monitoring method.  相似文献   
5.
Kamara BI  Manong DT  Brandt EV 《Phytochemistry》2005,66(10):1126-1132
A new dimeric dihydrochalcone, rel-(1β,2α)-di-(2,4-dihydroxybenzoyl)-rel-(3β,4α)-di-(4-hydroxyphenyl)-cyclobutane, accompanied by its apparent precursor, the known chalcone isoliquiritigenin, have been isolated from the roots of Agapanthus africanus (Liliaceae). The structure is based on spectroscopic methods including extensive NMR analyses, mass spectrometry and circular dichroism. Conclusions regarding the structure and relative configuration are supported by synthesis of the dimeric dihydrochalcone via a pericyclic [π2s + π2s] photocyclo-addition of the corresponding chalcone and consideration of the molecular symmetry involved.  相似文献   
6.
The trunk wood of Iryanthera polyneura Ducke (Myristicaceae) contains pinocembrin, 1-(2′,4′-dihydroxyphenyl)-3-(3″,4″-methylenedioxyphenyl)-propane, 1-(2′,4′-dihydroxy-3′-methylphenyl)-3-(2″-methoxy-4″, 5″-methylenedioxyphenyl)-propane and 4,2′,4′-trihydroxy-3-methoxydihydrochalcone.  相似文献   
7.
Bioassay-guided phytochemical investigation of the EtOAc fraction from the leaves of a Chinese medicinal herb, Eucalyptus citriodora Hook, resulted in the isolation of a new compound rhodomyrtosone E (1), along with 12 known compounds (213). The structure of the new compound was established by 1D and 2D NMR, MS data and X-ray crystallographic analysis. Betulinic acid (2) and corosolic acid (5) increased glucose transporter 4 (GLUT-4) translocation by 2.38 and 1.78-fold, respectively.  相似文献   
8.
Fisetin and 2′,4′,6′-trihydroxydihyrochalcone 4′-O-β-neohesperidoside were synthesized from commercially available quercetin and naringin in five steps. The key steps are site-selective deacetylation and subsequent deoxygenation. The target molecules were obtained in 37% and 23% yields from the starting materials, respectively.  相似文献   
9.
Trilobatin [4?-(β-D-glucopyranosyloxy)-2?,4”,6?-trihydroxydihydrochalcone] was synthesized from commercially available naringin in three steps with an overall yield of 30%. The key step was the acid-catalyzed site-selective hydrolysis of terminal α-rhamnopyranosidic linkage in neohesperidose involved in naringin under controlled conditions, by applying a high-pressure steam sterilizer.  相似文献   
10.
Neohesperidin dihydrochalcone (NHDC) was recently introduced as an activator of mammalian alpha‐amylase. In the current study, the effect of NHDC has been investigated on bacterial and fungal alpha‐amylases. Enzyme assays and kinetic analysis demonstrated the capability of NHDC to significantly activate both tested alpha‐amylases. The ligand activation pattern was found to be more similar between the fungal and mammalian enzyme in comparison with the bacterial one. Further, thermostability experiments indicated a stability increase in the presence of NHDC for the bacterial enzyme. In silico (docking) test locates a putative binding site for NHDC on alpha‐amylase surface in domain B. This domain shows differences in various alpha‐amylase types, and the different behavior of the ligand toward the studied enzymes may be attributed to this fact. Copyright © 2015 John Wiley & Sons, Ltd.  相似文献   
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