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Transformation of Natural Products by Marine-Derived Microorganisms
Published in Se-Kwon Kim, Marine Biochemistry, 2023
Thayane Melo de Queiroz, André Luiz Meleiro Porto
De Lise and co-workers (2016) described the isolation, recombinant expression in E. coli, and partial characterisation of a α-L-rhamnosidase (α-RHA) obtained from the marine bacteria Novosphingobium sp. PP1Y, which was isolated from surface seawater (Italy). In this study, the α-RHA enzyme was used in the hydrolysis of the flavonoids naringin, rutin, and neohesperidin dihydrochalcone into their glycosylated derivatives. The reactions were performed in Na-phosphate buffer (pH 7.0) under magnetic stirring at 40°C for 1–3 hours (Figure 5.9).
Selected Botanicals and Plant Products That Lower Blood Glucose (Continued)
Published in Robert Fried, Richard M. Carlton, Type 2 Diabetes, 2018
Robert Fried, Richard M. Carlton
Three compounds that were major contributors to the antioxidant activity in these fractions were obtained by reverse-phase preparative HPLC and identified as quercetin 3-O-rutinoside-7-O-α-L-rhamnosidase (quercetin 3-rut-7-rha), quercetin 3-O-rutinoside (rutin), and (−)-epicatechin, using NMR spectroscopy, HMBC, and ESI-MS spectrometry. The concentration of quercetin 3-rut-7-rha was 17.25 mg per 100 g of lychee pulp fresh weight.
Biocatalyzed Synthesis of Antidiabetic Drugs
Published in Peter Grunwald, Pharmaceutical Biocatalysis, 2019
FSA was also shown to accept various other N-Cbz-protected aldehydes (Concia et al., 2009) and azido-substituted aldehydes (Sugiyama et al., 2007) (compounds 134, Fig. 11.46) in combination with DHA, hydroxyacetone (HA), 1-hydroxybutan-2-one (HB) or glycolaldehyde (GO) as nucleophiles to provide various structurally related pyrrolidine-type iminocyclitols (e.g., 136 or 137). This route has provided easy access to some interesting drugs; for instance, 1,4-dideoxy-1,4-imino-D-arabinitol (DAB, 138), a potent α-glucosidase inhibitor (Saludes et al., 2007) possessing therapeutic potential as anti-hyperglycemic agent because of its capability to inhibit glycogen phosphorylase and glucagon-stimulated glycogen breakdown (Andersen et al., 1999; Walls et al., 2008; Praly and Vidal, 2010) or 1,4,5-trideoxy-1,4-imino-D-arabinitol (5-DDAB, 139), which was found to have inhibitory properties against α- and β-mannosidase from jack beans and snails, respectively, and α- and β-glucosidase (Sugiyama et al., 2007); its corresponding enantiomer (5-DLAB) is an inhibitor of α-L-rhamnosidase from Penicillium decumbens (Provencher et al., 1994). Chemoenzymatic synthesis of pyrrolidine-type iminocyclitols using FSA.
Extensive metabolism of flavonoids relevant to their potential efficacy on Alzheimer’s disease
Published in Drug Metabolism Reviews, 2021
Linarin (acacetin-7-O-β-D-rutinoside) is a flavone rutinoside as well, and was converted to acacetin, apigenin and phloroglucinol via ring cleavage in rats after oral administration, the last of which, as well as 4-hydroxybenzoic acid and 4-hydroxy benzaldehyde, was degraded by rat intestinal bacteria (Feng et al. 2018). After incubated with human intestinal bacteria, it was hydrolyzed to acacetin-7-O-β-D-glucoside and then to acacetin in turn followed by mono-methylation, acetylation, hydroxylation or hydrogenation principally mediated by Escherichia sp. 4 and 34, Enterococcus sp. 45 and Bacillus sp. 46 (Tao et al. 2016), all of which expressed both α-L-rhamnosidase and β-D-glucosidase, except Bacillus sp. 46 only producing α-L-rhamnosidase.
Enzyme-assisted modification of flavonoids from Matricaria chamomilla: antioxidant activity and inhibitory effect on digestive enzymes
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2020
Elida Paula Dini de Franco, Fabiano Jares Contesini, Bianca Lima da Silva, Anna Maria Alves de Piloto Fernandes, Camila Wielewski Leme, João Pedro Gonçalves Cirino, Paula Renata Bueno Campos, Patrícia de Oliveira Carvalho
Commercial hesperidinase and β-galactosidase are widely employed in biotechnological deglycosylation processes producing the respective partially deglycosylated flavonoids or aglycones. Hesperidinase is a fungal enzyme that expresses both α-l-rhamnosidase (EC 3.2.1.40) and β-d-glucosidase (3.2.1.21) activities resulting in rhamnose and glucose release, respectively, from a variety of conjugated flavonoids17. β-galactosidase can be obtained in large quantities from a special strain of Aspergillus oryzae and exhibits a strong linkage specificity for β 1–4 linkages galactosyl residues18. Previous results have shown the feasibility of producing highly purified kaempferol from two kaempferol glycosides by enzymatic hydrolysis using the optimum combination of the enzymes hesperidinase and β-galactosidase15. The combination of these two enzymes may account for a significant metabolic change in plant extracts rich in conjugated flavonoids such as chamomile infusion.