27740-01-8

Usage

Uses

Used in Cardio-cerebrovascular Applications:
Scutellarin is used as a microcirculation promoter for the treatment of cardio-cerebrovascular diseases. It helps improve blood flow and circulation in the heart and brain, which can be beneficial for patients with these conditions.
Used in Anticancer Applications:
Scutellarin is used as an anticancer agent, particularly for non-small cell lung cancer (NSCLC). It has been shown to inhibit the proliferation of cancer cells in a concentration-dependent manner and enhance apoptosis of tumor cells. Scutellarin has the potential to be a promising pharmaceutical candidate for cancer treatment.
Used in Lipid-Lowering Applications:
Scutellarin is used as a lipid-lowering agent in a high-fat diet-induced mouse model of non-alcoholic fatty liver disease (NAFLD). It decreases serum total cholesterol and LDL-cholesterol while increasing HDL-cholesterol, which can help improve overall lipid profile and reduce the risk of cardiovascular diseases.
Used in Antioxidative Applications:
Scutellarin is used as an antioxidant, reducing hepatic malondialdehyde (MDA) levels and increasing the activity of catalase (CAT) and total antioxidative capacity (T-AOC). This helps protect the liver from oxidative stress and damage.
Used in Neurocognitive Applications:
Scutellarin is used to prevent deficits in spatial and novel object memory in rats, as demonstrated in the Y maze and novel object recognition test. This suggests that Scutellarin may have potential applications in improving cognitive function and treating neurocognitive disorders.

InChI:InChI=1/C21H18O12/c22-8-3-1-7(2-4-8)10-5-9(23)13-11(31-10)6-12(14(24)15(13)25)32-21-18(28)16(26)17(27)19(33-21)20(29)30/h1-6,16-19,21-22,24-28H,(H,29,30)/t16-,17-,18+,19-,21+/m0/s1

Synthetic route

scutellarein 7-O-β-D-glucuronopyranoside methyl ester (119262-68-9) → scutellarin (27740-01-8)

Conditions	Yield
Stage #1: scutellarein 7-O-β-D-glucuronopyranoside methyl ester With water; sodium hydroxide In acetone at 0℃; for 0.2h; Inert atmosphere; Stage #2: With hydrogenchloride In water; acetone for 1h; pH=2-3; Reagent/catalyst; Temperature; Time; Concentration;	89%

scutellarein (529-53-3) + UDP-glucuronic acid (2616-64-0) → scutellarin (27740-01-8)

Conditions	Yield
With Tris-HCl buffer; UDP-glucuronate: baicalein 7-O-glucuronosyltransferase In water at 37℃; pH=7.5; Enzyme kinetics; Esterification; Enzymatic reaction;
With Veronica persica UDP-dependent glycosyl transferase 88D8 In potassium phosphate buffer at 30℃; pH=7.5;

Upstream product

• 529-53-3 scutellarein 
• 119262-68-9 scutellarein 7-O-β-D-glucuronopyranoside methyl ester 
• 54917-66-7 5,6,4'-triacetoxy-7-hydroxyflavon-7-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosiduronsauremethyl ester) 
• 1180-46-7 4,5,6,7-tetra-O-acetylflavone 
• 1432474-30-0 C₂₇H₂₅NO₁₇ 
• 1432474-29-7 C₂₈H₂₇NO₁₇ 
• 1432474-28-6 C₃₂H₂₉NO₁₅ 
• 1432474-27-5 C₂₈H₂₉NO₁₅ 
• 1432474-26-4 C₂₆H₂₅NO₁₅ 
• 2616-64-0 UDP-glucuronic acid 

Downstream Products

• 1401320-18-0 C₂₁H₂₀O₁₁ 
• 1180-46-7 4,5,6,7-tetra-O-acetylflavone 
• 33507-92-5 7-(benzyloxy)-5,6-diacetoxy-2-(4-acetoxyphenyl)-4H-chromen-4-one 
• 33507-93-6 7-hydroxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 
• 1447-88-7 hispidulin 
• 1258506-19-2 5,6-dihydroxy-7-(methoxymethoxy)-2-(4-(methoxymethoxy)phenyl)-4H-chromen-4-one 
• 1402607-44-6 5,6-dihydroxy-2-(4-hydroxyphenyl)-7-(methoxymethoxy)-4H-chromen-4-one 
• 1105056-24-3 9-hydroxy-6-(4-hydroxyphenyl)-2,2-diphenyl-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 
• 1402607-40-2 9-hydroxy-2,2-diphenyl-6-[4-(phenylmethoxy)phenyl]-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 
• 1351585-69-7 5,6,7-trihydroxy-2-[4-(phenylmethoxy)phenyl]-4H-1-benzopyran-4-one 
• 62252-32-8 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one 
• 28736-83-6 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one 
• 119262-68-9 scutellarein 7-O-β-D-glucuronopyranoside methyl ester 

Relevant academic research and scientific papers

Total synthesis of scutellarin and apigenin 7-O-β-d-glucuronide

A general protocol for direct glucuronic linkages formation featuring Au(I)-catalyzed appropriately protected glucuronyl o-alkynylbenzoate-involved glycosylation reaction, as well as a concise approach for easy access of scutellarein prominent for the mild and efficient hydroxyl group installation via borylation-oxidation sequence from flavanone derivative, has been established, based on which a novel route for scutellarin derivatives preparation has been devised. The developed strategies, among which the stepwise deprotection process was also included, guarantee the high whole synthetic efficiency, and definitely will find broad application in diversity-oriented synthesis of bioactive flavonoid glycosides.

METHOD FOR PREPARING 5,6,4'-TRIHYDROXYFLAVONE-7-0-D-GLUCURONIC ACID

The present invention relates to the field of drug synthesis. Disclosed is a method for preparing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid. The method for preparing 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid of the present invention uses 5,6,7,4'-tetrahydroxyflavone as a raw material and adopts a new synthetic route to obtain high-purity 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid through an acylation reaction, a glycosylation reaction, and two-step hydrolysis. The preparing method of the present invention has a short synthetic route, low cost, and high reaction yield, the product is easy for purification, and the method is applicable to industrial production of 5,6,4'-trihydroxyflavone-7-O-D-glucuronic acid.

Synthesis and physiochemical property evaluation of carbamate derivatives of scutellarin methyl ester

A series of carbamate prodrugs of scutellarin methyl ester (4a-4e) were prepared in the presence of bis(trichloromethyl) carbonate (BTC) with scutellarin methyl esters and l-amino acid tert-butyl ester hydrochloride as starting materials. In vitro stability and aqueous solubility of target compounds were evaluated. The results indicated that compounds 4d and 4e have higher solubility and in vitro stability than scutellarin respectively.

Co-pigmentation and flavonoid glycosyltransferases in blue Veronica persica flowers

Glycosylation is one of the key modification steps for plants to produce a broad spectrum of flavonoids with various structures and colors. A survey of flavonoids in the blue flowers of Veronica persica Poiret (Lamiales, Scrophulariaceae), which is native of Eurasia and now widespread worldwide, led to the identification of highly glycosylated flavonoids, namely delphinidin 3-O-(2-O-(6-O-p-coumaroyl-glucosyl)-6-O-p-coumaroyl-glucoside)-5-O-glucoside (1) and apigenin 7-O-(2-O-glucuronosyl)-glucuronide (2), as two of its main flavonoids. Interestingly, the latter flavone glucuronide (2) caused a bathochromic shift on the anthocyanin (1) toward a blue hue in a dose-dependent manner, showing an intermolecular co-pigment effect. In order to understand the molecular basis for the biosynthesis of this glucuronide, we isolated a cDNA encoding a UDP-dependent glycosyltransferase (UGT88D8), based on the structural similarity to flavonoid 7-O-glucuronosyltransferases (F7GAT) from Lamiales plants. Enzyme assays showed that the recombinant UGT88D8 protein catalyzes the 7-O-glucuronosylation of apigenin and its related flavonoids with preference to UDP-glucuronic acid as a sugar donor. Furthermore, we identified and functionally characterized a cDNA encoding another UGT, UGT94F1, as the anthocyanin 3-O-glucoside-2″-O-glucosyltransferase (A3Glc2″GlcT), according to the structural similarity to sugar-sugar glycosyltransferases classified to the cluster IV of flavonoid UGTs. Preferential expression of UGT88D8 and UGT94F1 genes in the petals supports the idea that these UGTs play an important role in the biosynthesis of key flavonoids responsible for the development of the blue color of V. persica flowers.

Purification and characterization of UDP-glucuronate: Baicalein 7-O- glucuronosyltransferase from Scutellaria baicalensis Georgi. cell suspension cultures

UDP-glucuronate: baicalein 7-O-glucuronosyltransferase (UBGAT) catalyzes the transfer of glucuronic acid from UDP-glucuronic acid to the 7-OH of baicalein. UBGAT was purified from cultured cells of Scutellaria baicalensis Georgi (Lamiaceae). It was purified 95-fold using various chromatography and chromatofocusing procedures to apparent homogeneity. The M(r) was estimated to be 110 kDa by gel filtration chromatography with a 52 kDa subunit by SDS- PAGE. The isoelectric point was pH 4.8. UBGAT was specific to UDP-glucuronic acid as a sugar donor and flavones with substitution ortho- to the 7-OH group such as baicalein (6-OH), scutellarein (6-OH) and wogonin (8-OMe). (C) 2000 Elsevier Science Ltd.