117405-49-9

Upstream product

• 7400-08-0 p-Coumaric Acid 
• 133-89-1 diphosphoric acid 1''-β-D-[1'']glucopyranosyl ester 2-(uridin-5'-yl)ester 
• 153-18-4 rutin 
• 117405-48-8 4-O-β-D-glucopyranosyl-Z-4-hydroxycinnamic acid 
• 66642-77-1 methyl 4-[(2',3',4',6'-tetra-O-acetyl)-β-D-glucopyranosyl]coumarate 
• 80396-57-2 protoplumericin 
• 134955-57-0 4-O-(6''-O-p-coumaroyl-β-D-glucopyranosyl)-p-coumaric acid 

Downstream Products

• 2280-44-6 D-Glucose 
• 7400-08-0 p-Coumaric Acid 
• 50-99-7 D-glucose 
• 501-98-4 (Z)-p-coumaric acid 
• 554-87-0 methyl glucosyl-p-coumaroate 

Relevant academic research and scientific papers

Rapid biosynthesis of phenolic glycosides and their derivatives from biomass-derived hydroxycinnamates

Biomass-derived hydroxycinnamates (mainly includingp-coumaric acid and ferulic acid), which are natural sources of aromatic compounds, are highly underutilized resources. There is a need to upgrade them to make them economically feasible. Value-added phenolic glycosides and their derivatives, both belonging to a class of plant aromatic natural products, are widely used in the nutraceutical, pharmaceutical, and cosmetic industries. However, their complex aromatic structures make their efficient biosynthesis a challenging process. To overcome this issue, we created three novel synthetic cascades for the biosynthesis of phenolic glycosides (gastrodin, arbutin, and salidroside) and their derivatives (hydroquinone, tyrosol, hydroxytyrosol, and homovanillyl alcohol) fromp-coumaric acid and ferulic acid. Moreover, because the biomass-derived hydroxycinnamates directly provided aromatic units, the cascades enabled efficient biosynthesis. We achieved substantially high production rates (up to or above 100-fold enhancement) relative to the glucose-based biosynthesis. Given the ubiquity of the aromatic structure in natural products, the use of biomass-derived aromatics should facilitate the rapid biosynthesis of numerous aromatic natural products.

Glycosidase-Catalyzed Synthesis of Glycosyl Esters and Phenolic Glycosides of Aromatic Acids

Phenolic glycosides occur naturally in many plants and as such are often present in the human diet. Their isolation from natural sources is usually laborious due to their presence in complex matrices. Their chemical and enzymatic syntheses have been found complex, time-consuming, and costly, yielding only small amounts of glycosylated products. In quest of a convenient biocatalytic route to structurally complex phenolic glycosides, we discovered that the rutinosidase from Aspergillus niger not only efficiently converts hydroxylated aromatic acids (e. g. coumaric and ferulic acids) into the respective phenolic rutinosides, but surprisingly also catalyzes the formation of the respective glycosyl esters. We report here the results of a systematic study presenting the unique synthesis of naturally occurring glycosyl esters and phenolic glycosides accomplished by glycosidase catalysis. A panel of aromatic acids was tested as glycosyl acceptors and the crucial structural features required for the formation of glycosyl esters were identified. In the light of the present structure-activity relationship study, a plausible reaction mechanism was proposed. All the products were fully structurally characterized by NMR and MS. (Figure presented.).

Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia)

Phenolic compounds of sainfoin (Onobrychis viciifolia) variety Cotswold Common are assumed to contribute to its nutritive value and bioactive properties. A purified acetone/water extract was separated by Sephadex LH-20 gel chromatography. Sixty-three phen

Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation

This work describes the chemical synthesis of O-aryl-β-D-glucosides and 1-O-β-D-glucosyl esters of hydroxycinnamic acids. In particular, O-aryl-β-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-β-D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl-β-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the π-stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.

Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.

The glycosylated pyrrolizidine alkaloid, thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemic

UDPG: p-COUMARATE GLUCOSYLTRANSFERASE ACTIVITY IN ENZYME EXTRACTS FROM HIGHER PLANTS

Leaves of Coleus, Pilea, Cistus and Cestrum, and ripe tomatoes were all able to convert trans-cinnamic acid- into glucose esters of cinnamic acids.The pool sizes of these esters were measured by the radioisotopic dilution method, and they were found to be of the order of a few μg/g fresh plant material. 1-O-Caffeoyl-β-D-glucose in Cestrum leaves amounted to 70 μg/g fresh plant material.Enzyme extracts from Cestrum leaves were able to convert trans-p-coumaric acid- to 1-O-p-coumaroyl-β-D-glucose, using UDPG as a source of glucose.This enzyme activity could be measured only by trapping techniques, due to the presence of considerable hydrolase activity in crude enzyme extracts.Key Word Index- Coleus; Labiatae; Cestrum; Lycopersicon; Solanaceae; UDPG; p-coumarate glucosyltransferase; hydroxycinnamic acids; biosynthesis.