Dataset Information

3‴-O-Foliamenthoyl-Rutin, a New Flavonoid Glycoside from the Roots of Nymphoides peltata.

ABSTRACT: Nymphoides peltata (Menyanthaceae) has been used as a medicinal herb in traditional medicines to treat conditions such as strangury, polyuria, swelling, and as a diuretic and antipyretic. In our ongoing research to discover novel structural and/or biological natural products in natural resources, five flavonoids, quercetin (1), quercitrin (2), isoquercetin (3), quercetin-3-O-vicianoside (4), and rutin (5), as well as a new flavonoid glycoside, 3‴-O-foliamenthoyl-rutin (6), were isolated from the MeOH extract of N. peltata roots. The chemical structure of the new compound (6) was determined by analyzing 1D and 2D NMR spectra and high-resolution (HR) electrospray ionization mass spectroscopy (ESIMS), along with a chemical reaction. The wound-healing activities of the isolated compounds (1-6) were evaluated using a HaCaT cell scratch test. Among the isolates, isoquercetin (3), quercetin-3-O-vicianoside (4), and 3‴-O-foliamenthoyl-rutin (6) promoted HaCaT cell migration over scratch wounds, with compound 4 being the most effective. Our findings provide experimental data supporting the potential of quercetin-3-O-vicianoside (4) as a wound-healing agent.

SUBMITTER: Kim TY

PROVIDER: S-EPMC10748241 | biostudies-literature | 2023 Dec

REPOSITORIES: biostudies-literature

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3‴-O-Foliamenthoyl-Rutin, a New Flavonoid Glycoside from the Roots of Nymphoides peltata.

Kim Tae-Young TY Lee Bum Soo BS Jo Beom-Geun BG Heo Seong Pil SP Keem Min-Ji MJ Kwon Taek-Hwan TH Kim Su-Nam SN Kim Ki Hyun KH Yang Min Hye MH

Plants (Basel, Switzerland) 20231206 24

Nymphoides peltata (Menyanthaceae) has been used as a medicinal herb in traditional medicines to treat conditions such as strangury, polyuria, swelling, and as a diuretic and antipyretic. In our ongoing research to discover novel structural and/or biological natural products in natural resources, five flavonoids, quercetin (1), quercitrin (2), isoquercetin (3), quercetin-3-O-vicianoside (4), and rutin (5), as well as a new flavonoid glycoside, 3‴- ...[more]

PMID: 38140410

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Project description:BackgroundNymphaeid macrophytes, rooting in the sediment of water bodies and characterized by floating leaves, play an important role in wetland ecosystems. The present research deals with the effects of limited space, limited nutrient availability, water temperature and an unexpected inundation on the production, turnover and plasticity of floating leaves of the globally widespread species Nymphoides peltata (Fringed waterlily).MethodsThe effects of these environmental conditions were studied in two plots in outdoor concrete tanks (CT1, CT2, mesocosms simulating occurrence in small ponds) and in two plots in the floodplain oxbow lake Bemmelse Strang (BS1, BS2). Plot CT1 was situated in a stand coexisting with helophytes, plot CT2 in a monospecific stand, plot BS1 in the center and plot BS2 at the open water border of a monospecific stand. All floating leaf blades within the plots were marked at appearance at the water surface and subsequently length, width and damage of each leaf and maximum and minimum water temperatures were measured bi-weekly. Area and biomass of leaf blades were calculated based on leaf length and width and were used to calculate turnover rates and production.ResultsThe growth period started in May and ended mid-October with continuous production of floating leaves during nearly the whole vegetation period. In the tanks the water level was very stable, but the lake underwent an inundation by river water, causing a sudden loss of existing leaves. Considering environmental conditions and based on the assumed ranking from low to high nutrient availability, the ranking of the plots was CT1, CT2, BS1, BS2. This order was found for maximum leaf life span and maximum leaf length, and the reverse order was found for number of leaves, new leaves per day and duration of the vegetation period. Turnover rates appeared to be relatively similar for plots CT1, CT2 and BS1, but for the deeper border plot BS2 lower ratios were found. These results indicate that increased enclosure with expected nutrient limitation causes (1) the production of high numbers of small leaves with larger totals for leaf area and biomass, (2) a shift towards increased sexual reproduction by the production of more flowering stem leaves.

Project description:BackgroundFlavonoid glycosides extracted from roots of Scutellaria baicalensis exhibit strong pharmaceutical antitumor, antioxidative, anti-inflammatory, and antiviral activities. UDP glycosyltransferase (UGT) family members are responsible for the transfer of a glycosyl moiety from UDP sugars to a wide range of acceptor flavonoids. Baicalin is the major flavonoid glycoside found in S. baicalensis roots, and its aglycone baicalein is synthesized from a specially evolved pathway that has been elucidated. However, it is necessary to carry out a genome-wide study of genes involved in 7-O-glucuronidation, the final biosynthesis step of baicalin, which might elucidate the relationship between the enzymes and the metabolic accumulation patterns in this medicinal plant.ResultsWe reported the phylogenetic analysis, tissue-specific expression, biochemical characterization and evolutionary analysis of glucosyltransferases (SbUGTs) and glucuronosyltransferases (SbUGATs) genes based on the recently released genome of S. baicalensis. A total of 124 UGTs were identified, and over one third of them were highly expressed in roots. In vitro enzyme assays showed that 6 SbUGTs could use UDP-glucose as a sugar donor and convert baicalein to oroxin A (baicalein 7-O-glucoside), while 4 SbUGATs used only UDP-glucuronic acid as the sugar donor and catalyzed baicalein to baicalin. SbUGAT4 and SbUGT2 are the most highly expressed SbUGAT and SbUGT genes in root tissues, respectively. Kinetic measurements revealed that SbUGAT4 had a lower Km value and higher Vmax/Km ratio to baicalein than those of SbUGT2. Furthermore, tandem duplication events were detected in SbUGTs and SbUGATs.ConclusionsThis study demonstrated that glucosylation and glucuronidation are two major glycosylated decorations in the roots of S. baicalensis. Higher expression level and affinity to substrate of SbUGAT4, and expansion of this gene family contribute high accumulation of baicalin in the root of S. baicalensis.

Dataset Information

3‴-O-Foliamenthoyl-Rutin, a New Flavonoid Glycoside from the Roots of Nymphoides peltata.

Publications

3‴-<i>O</i>-Foliamenthoyl-Rutin, a New Flavonoid Glycoside from the Roots of <i>Nymphoides peltata</i>.

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