ABSTRACT
Two new potential antifungal coumarin glycosides, 6-chlorocoumarin 7-O-beta-D-glucopyranoside (1) and 7-hydroxy-4-trifluoromethyl-coumarin 5-O-beta-D-glucopyranoside (2), were synthesized via enzyme-mediated glycosylation of the respective aglycone, 6-chloro-7-hydroxycoumarin and 5,7-dihydroxy-4-trifluoromethylcoumarin, using transgenic hairy roots of Polygonum multiflorum. Instead of application of the isolated enzyme and exogenous sugar donors, hairy roots of P. multiflorum were successfully adapted as a whole-cell biocatalyst.
Subject(s)
Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Coumarins/chemical synthesis , Coumarins/pharmacology , Polygonum/chemistry , Catalysis , Coumarins/chemistry , Glycosides/chemical synthesis , Glycosides/chemistry , Glycosides/pharmacology , Indicators and Reagents , Magnetic Resonance Spectroscopy , Plant Roots/chemistry , Plant Roots/enzymology , Solubility , Spectrometry, Mass, Electrospray IonizationABSTRACT
Using 7-hydroxy-4-methylcoumarin (1), 7-hydroxy-4-phenylcoumarin (2), 5,7-dihydroxy-4-methylcoumarin (3), 7,8-dihydroxycoumarin (4) as substrates, three new compounds, 4-methylcoumarin-7-O-beta-D-xylopyranosyl (1 --> 6) beta-D-glucopyranoside (1b), 4-phenylcoumarin-7-O-beta-D-glucopyranosyl (1 --> 6) beta-D-glucopyranoside (2b), 4-methylcoumarin-5,7-O-beta-D-diglucoside (3b), along with four known compounds (1a, 2a, 3a and 4a) were biosynthesized by the cell suspension cultures of Catharanthus roseus as biocatalyst. Their structures were elucidated by analysis of the physicochemical properties and 1H NMR, 13C NMR, HMBC and ESI-MS spectra. Besides, the results also showed that this novel biocatalyst system of C. roseus cell cultures has a great capacity of regio-selective glycosylation to the hydroxyl group of the exogenous substrates. Co-culture time curves on conversion were also established.
Subject(s)
Catharanthus/metabolism , Coumarins/metabolism , Biotransformation , Cells, Cultured , Chromatography, High Pressure Liquid , Coculture Techniques , Dimethyl Sulfoxide , Kinetics , Magnetic Resonance Spectroscopy , Solvents , Spectrometry, Mass, Electrospray IonizationABSTRACT
To investigate the substrate specificity and regio-selectivity of coumarin glycosyltransferases in transgenic hairy roots of Polygonum multiflorum, esculetin (1) and eight hydroxycoumarins (2-9) were employed as substrates. Nine corresponding glycosides (10-18) involving four new compounds, 6-chloro-4-methylcoumarin 7-O-ß-D-glucopyranoside (15), 6-chloro-4-phenylcoumarin 7-O-ß-D-glucopyranoside (16), 8-hydroxy-4-methylcoumarin 7-O-ß-D-glucopyranoside (17), and 8-allyl-4-methylcoumarin 7-O-ß-D-glucopyranoside (18), were biosynthesized by the hairy roots.
Subject(s)
Coumarins/metabolism , Glycosides/biosynthesis , Glycosyltransferases/metabolism , Plant Roots/enzymology , Polygonum/enzymology , Chromatography, High Pressure Liquid , Coumarins/chemistry , Glycosides/chemistry , Glycosyltransferases/chemistry , Magnetic Resonance Spectroscopy , Molecular Structure , Plant Roots/chemistry , Plant Roots/genetics , Plants, Genetically Modified/chemistry , Plants, Genetically Modified/enzymology , Polygonum/chemistry , Polygonum/genetics , Stereoisomerism , Substrate SpecificityABSTRACT
Hand-foot-and-mouth disease is caused by intestinal virus infection. The viruses coxsackie A16 (CA16) and enterovirus 71 (EV71) are the main pathogens. Between them, the virus EV71 is more dangerous and easier to cause serious complications, which leads to death or disability. Currently, there are no effective antiviral drugs to treat EV71 infection. Therefore, developing an effective drug against EV71 virus activity is significant. It has a huge potency of screening the anti-EV71 components and developing the new drugs from the abundant traditional Chinese medicines (TCMs). Meanwhile, since hand-foot-and-mouth disease spread in Shanghai in 1981, a growing number of reports on TCMs treatment in clinic have been published. In addition, most of treatments with various ways are effective, which play a positive role on improving clinic treatment and controlling diseases. Moreover, special clinic advantages and features of TCMs were obviously shown.
