23627-87-4

Usage

Uses

Used in Pharmaceutical Industry:
Kaempferol-3-O-galactoside is used as a bioactive compound for its potential therapeutic properties. It exhibits antioxidant, anti-inflammatory, and anti-cancer activities, making it a promising candidate for the development of novel drugs and supplements.
Used in Cosmetic Industry:
In the cosmetic industry, kaempferol-3-O-galactoside is used as an ingredient in skincare products for its antioxidant and anti-inflammatory properties. It helps protect the skin from environmental stressors and supports skin health by reducing inflammation and promoting collagen synthesis.
Used in Functional Foods:
Kaempferol-3-O-galactoside is used as an additive in the functional food industry due to its health-promoting properties. It can be incorporated into various food products to enhance their nutritional value and provide additional health benefits, such as improved immune function and reduced risk of chronic diseases.
Used in Nutraceutical Industry:
As a nutraceutical, kaempferol-3-O-galactoside is used to develop dietary supplements and fortified foods that offer specific health benefits. Its antioxidant and anti-inflammatory properties make it an attractive option for products targeting immune support, cardiovascular health, and overall well-being.
Used in Agricultural Industry:
In agriculture, kaempferol-3-O-galactoside can be used as a natural additive to enhance the nutritional value of animal feed, promoting better health and productivity in livestock. Additionally, it may be employed in the development of plant protection products, leveraging its antioxidant properties to protect crops from various stressors and diseases.

InChI:InChI=1/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17+,18-,21?/m1/s1

Upstream product

• 133-89-1 UDP-glucose 
• 520-18-3 kaempferol 
• 2956-16-3 uridine 5'-diphospho-D-galactose 

Downstream Products

• 11055-94-0 hepta-O-acetyltrifolin 
• 520-18-3 kaempferol 
• 1030269-14-7 heptamethyltrifolin 
• 59-23-4 D-Galactose 
• 99-96-7 4-hydroxy-benzoic acid 
• 10257-28-0 D-Galactose 

Relevant academic research and scientific papers

Highly Promiscuous Flavonoid 3- O-Glycosyltransferase from Scutellaria baicalensis

A highly regio-specific and donor-promiscuous 3-O-glycosyltransferase, Sb3GT1 (UGT78B4), was discovered from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3-O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could be a promising catalyst to increase structural diversity of flavonoid 3-O-glycosides.

Ep7GT, a glycosyltransferase with sugar donor flexibility from: Epimedium pseudowushanense, catalyzes the 7- O -glycosylation of baohuoside

Icariin (1a), a 7-O-glycosylated flavonoid glycoside, is recognized as the major pharmacologically active ingredient of Epimedium plants, which have been used in traditional Chinese medicine for thousands of years. However, no glycosyltransferase (GT) responsible for the 7-O-glycosylation of flavonoids has been identified from Epimedium plants to date. Herein, a GT, Ep7GT, was identified from E. pseudowushanense B. L. Guo, which can regiospecifically transfer a glucose moiety to baohuoside (1) at 7-OH to form icariin (1a). Ep7GT showed a rare broad donor substrate spectrum, including UDP-glucose, UDP-xylose, UDP-N-acetylglucosamine, UDP-rhamnose, UDP-galactose, UDP-glucuronic acid and TDP-glucose. Moreover, two new derivatives of icariin (1a), 7-O-β-d-[2-(acetylamino)-2-deoxy-glucopyranosyl]-baohuoside (1b) and 7-O-β-d-xylosyl-baohuoside (1c), were biosynthesized by using Ep7GT in vitro. Engineered Escherichia coli harbouring Ep7GT was constructed, and 10.1 μg mL-1 icariin (1a) was yielded by whole-cell biotransformation with baohuoside (1) as the substrate. The present work not only characterizes the GT responsible for the 7-O-glycosylation in the biosynthesis of icariin in Epimedium plants, but also indicates the significant potential of an enzymatic approach for the production of glycosylated baohuoside derivatives with different sugar moieties. What's more, these findings also provide a promising alternative for producing natural/unnatural bioactive flavonoid glycosides by metabolic engineering.

Kaempferol and its glycosides from Equisetum silvaticum L. from the khanty-mansi autonomous area

Three flavonoids were isolated from the aerial part of the wood horsetail (Equisetum silvaticum L.); two of them were found for the first time. The compounds were identified as kaempferol, kaempferol 3-O-β-D-galactopyranosyl-7-O-α-L-rhamnopyranoside and kaempferol 3-O-rutinosyl-7-O-L-rhamnopyranoside on the basis of the chemical transformations and IR, UV, 1H-NMR and mass spectra.

Functional characterization of a UDP-glucose:flavonoid 3-O- glucosyltransferase from the seed coat of black soybean (Glycine max (L.) Merr.)

The seed coats of black soybean (Glycine max (L.) Merr.) accumulate red (cyanidin-), blue (delphinidin-), purple (petunidin-), and orange (pelargonidin-based) anthocyanins almost exclusively as 3-O-glucosides; however, the responsible enzyme has not been identified. In this study, the full-length cDNA which encodes the enzyme that catalyzes the final step in anthocyanin biosynthesis, namely UDP-glucose:flavonoid 3-O-glucosyltransferase (UGT78K1), was isolated from the seed coat tissue of black soybean using rapid amplification of cDNA ends (RACE). Of the 28 flavonoid substrates tested, the purified recombinant protein glucosylated only anthocyanidins and flavonols, and demonstrated strict 3-OH regiospecificity. Galactose could also be transferred with relatively low activity to the 3-position of cyanidin or delphinidin in vitro. These findings are consistent with previous reports of mainly 3-O-glucosylated and minor amounts of 3-O-galactosylated anthocyanins in the seed coat of black soybean. The recombinant enzyme exhibited pronounced substrate inhibition by cyanidin at 100 μM acceptor concentration. Transfer of UGT78K1 into the Arabidopsis T-DNA mutant (ugt78d2) deficient in anthocyanidin and flavonol 3-O-glucosyltransferase activity, restored the accumulation of anthocyanins and flavonols, suggesting the in vivo function of the enzyme as a flavonoid 3-O-glucosyltransferase. Genomic and phylogenetic analyses suggest the existence of three additional soybean sequences with high similarity to UGT78K1. RT-PCR confirmed the co-expression of one of these genes (Glyma08g07130) with UGT78K1 in the seed coat of black soybean, suggesting possible functional redundancies in anthocyanin biosynthesis in this tissue.

Isolation and antioxidant activity of galloyl flavonol glycosides from the seashore plant, Pemphis acidula.

Four kinds of galloyl flavonol glycosides were found in the leaf extract of Pemphis acidula, a plant growing on the subtropical seashore. Their chemical structures were elucidated to be quercetin or kaempferol 6 -O-galloyl-beta-D-glycosides by using spectroscopic and chemical analyses. One of the flavonols, kaempferol-3-O-(6-O-galloyl-beta-D-galactopyranoside), was newly isolated from natural sources and its structure was completely determined in this investigation. The antioxidant-related activities of the galloyl flavonoids were examined by the DPPH antiradical activity, inhibition of methyl linoleate oxidation, and inhibition of oxidative cell death. These results were compared with those of the corresponding non-galloylated flavonol glycosides and their aglycones. The galloyl flavonoids showed more efficient activity than that of the corresponding flavonol glycosides, but not more than that of the corresponding aglycones in the three assays applied.