18003-33-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Hydroxyluteolin is used as a therapeutic agent for enhancing the uptake of magnetic nanoparticles (MNPs) with an associated therapeutic agent to target sites, such as tumors. This property makes it a promising candidate for drug delivery and cancer treatment.
Used in Herbal Medicine Analysis:
6-Hydroxyluteolin is used in the analysis of Oroxylum indicum, a popular Chinese herbal medicine used for treating conditions like hyperactivity and sore throat. Its presence in the plant helps to determine the quality and efficacy of the herbal medicine.

InChI:InChI=1/C15H10O7/c16-7-2-1-6(3-8(7)17)11-4-9(18)13-12(22-11)5-10(19)14(20)15(13)21/h1-5,16-17,19-21H

Upstream product

• 6962-57-8 3,6-dihydroxy-2,4-dimethoxyacetophenone 
• 24824-54-2 3,4-dimethoxybenzoic anhydride 
• 71847-58-0 5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 2306-27-6 sinensetin 
• 18085-97-7 jaceosidin 
• 520-11-6 eupafolin 
• 36810-81-8 5,7-dihydroxy-8,3',4'-trimethoxyflavone 
• 13003-74-2 5-hydroxy-3’,4’,7,8-tetramethoxyflavone 
• 27696-41-9 3′,4′,5,7,8-pentahydroxyflavone 
• 25782-21-2 6-hydroxyluteolin 5,7,3'-trimethyl ether 
• 25782-20-1 6-hydroxyluteolin 5,7,4'-trimethyl ether 
• 25782-29-0 Acetic acid 2-(4-acetoxy-3-methoxy-phenyl)-5,7-dimethoxy-4-oxo-4H-chromen-6-yl ester 
• 25782-28-9 Acetic acid 2-(3-acetoxy-4-methoxy-phenyl)-5,7-dimethoxy-4-oxo-4H-chromen-6-yl ester 
• 10034-85-2 hydrogen iodide 

Downstream Products

• 27302-42-7 5,6,7,3',4'-pentaacetoxyflavone 
• 2306-27-6 sinensetin 
• 21763-80-4 5-desmethylsinensetin 
• 137231-91-5 (2R,3R)-7-(3,4-Dihydroxy-phenyl)-10-hydroxy-3-(4-hydroxy-3-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-1,4,8-trioxa-phenanthren-5-one 
• 137231-88-0 Scutellaprostin F 
• 30987-78-1 6,8-(dipiperidinomethyl)quercetin 
• 30987-77-0 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-(morpholinomethyl)-4H-chromen-4-one 
• 39777-72-5 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((4-methylpiperazin-1-yl)methyl)-4H-chromen-4-one 
• 30987-76-9 2-(3,4-dihydroxy-phenyl)-8-dimethylaminomethyl-3,5,7-trihydroxy-chromen-4-one 
• 478-01-3 nobiletin 
• 683278-67-3 5,8-dihydroxy-6,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 2192-25-8 5-hydroxy-3',4',6,7,8-pentamethoxyflavone 

Relevant academic research and scientific papers

FLAVONE GLYCOSIDES OF SALVIA TRILOBA

From Salvia triloba, 13 flavonids were isolated and identified.The 7-glucosides and 7-glucoronides of apigenin, luteolin, 6-methoxyapigenin and 6-methoxyluteolin and chrysoeriol 7-glucuronide were identified.Also present were 6,8-di-C-glucosylapigenin, luteolin 7-diglucoside, luteolin 7-glucuronide-3'-glucoside and 6-hydroxy-luteolin 6,3'-dimethyl ether.Key Word Index-Salvia triloba; Labiatae; 6-methoxyflavones; flavone glucosides; chemosystematics.

New Flavonoids and Turkesterone-2-O-Cinnamate from Leaves of Rhaponticum uniflorum

Leaves of Rhaponticum uniflorum (L.) DC. (Asteraceae) afforded 46 compounds including seven new flavonoids that were identified using UV, IR, and NMR spectroscopy and mass spectrometry as 6-hydroxyluteolin-7-O-(2′-O-caffeoyl)-β-D-glucopyranoside (rhaunoside A, 1), 6-hydroxyluteolin-7-O-(6″-O-cinnamoyl)-β-D-glucopyranoside (rhaunoside B, 2), 6-hydroxyluteolin-4′-O-β-D-glucopyranoside (rhaunoside C, 3), nepetin-7-O-(6″-O-caffeoyl)-β-D-glucopyranoside (rhaunoside D, 4), nepetin-7-O-(6″-O-cinnamoyl)-β-D-glucopyranoside (rhaunoside E, 5), nepetin-3′-O-β-D-glucopyranoside (rhaunoside F, 6), and luteolin-7-O-(2″-O-caffeoyl)-β-D-glucopyranoside (rhaunoside G, 7) and the new ecdysteroid turkesterone-2-O-cinnamate (8).

Phytochemical Characterization of Low Molecular Weight Constituents from Marshmallow Roots (Althaea officinalis) and Inhibiting Effects of the Aqueous Extract on Human Hyaluronidase-1

Extract RE was obtained from the roots of Althaea officinalis in a yield of 8.1%, related to the dried plant material, by extraction with MeOH-H2O (1:1), followed by precipitation with EtOH to remove high molecular weight constituents. Phytochemical investigation of RE revealed the presence of N-phenylpropenoyl-l-amino acid amides 1-5, 8% glycine betaine 6, about 9% total amino acids with proline as the main compound, and about 61% mono- and oligomeric carbohydrates with sucrose as the main compound. Further fractionation revealed the presence of a hypolaetin diglycoside (12) and four hypolaetin glycosides (7-9 and 11) with O-sulfocarbohydrate moieties; additionally, 4′-O-methylisoscutellarein-8-O-β-d-(3-O-sulfo)glucuronopyranoside (10) and the diglycosylated coumarin haploperoside D (13) were identified. The hypolaetin-O-sulfoglycosides 7-10 are new natural products. RE inhibited the enzymatic activity of surface-displayed human hyaluronidase-1 on Escherichia coli F470 cells with an IC50 of 7.7 mg/mL. RE downregulated mRNA expression of hyal-1 in HaCaT keratinocytes at 125 and 250 μg/mL, respectively. These data contribute to a deeper phytochemical understanding of marshmallow root extracts and to the positive influence of extracts used for therapy of irritated and inflamed buccal tissue and cough.

On the difference in decomposition of taxifolin and luteolin vs. fisetin and quercetin in aqueous media

Abstract: The decomposition of flavonols quercetin and fisetin, flavone luteolin and flavanone taxifolin was studied in slightly alkaline solution under ambient conditions. The study was based on spectrophotometry and high-pressure liquid chromatography. Products formed by atmospheric oxygen oxidation and hydrolysis were identified by HPLC–DAD and HPLC–ESI-MS/MS. Only small differences in the chemical structure of flavonoids resulted in extremely variable oxidation pathways and products. Oxidation of flavonols led to the formation of both a benzofuranone derivative and several open structures. On the contrary, the benzofuranone derivative was not found as a product of taxifolin and luteolin oxidative decomposition. These compounds were oxidized to their hydroxylated derivatives and typical open structures. Quercetin was not identified as a possible oxidation product of taxifolin. Graphical Abstract: [Figure not available: see fulltext.]

Regioselective hydroxylation of diverse flavonoids by an aromatic peroxygenase

Aromatic peroxygenases are extracellular fungal biocatalysts that selectively oxidize a variety of organic compounds. We found that the peroxygenase of the fungus Agrocybe aegerita (AaeAPO) catalyzes the H 2O2-dependent hydroxylation of diverse flavonoids. The reactions proceeded rapidly and regioselectively yielding preferentially monohydroxylated products, e.g., from flavanone, apigenin, luteolin, flavone as well as daidzein, quercetin, kaempferol, and genistein. In addition to hydroxylation, O-demethylation of fully methoxylated tangeretin was catalyzed by AaeAPO. The enzyme was merely lacking activity on the quercetin glycoside rutin, maybe due to sterical hindrance by the bulky sugar substituents. Mechanistic studies indicated the presence of epoxide intermediates during hydroxylation and incorporation of H2O2-derived oxygen into the reaction products. Our results raise the possibility that fungal peroxygenases may be useful for versatile, cost-effective, and scalable syntheses of flavonoid metabolites.

Importance of the B ring and its substitution on the α-glucosidase inhibitory activity of baicalein, 5,6,7-trihydroxyflavone

Hydroxychroniones and B-ring-substituted 5,6,7-trihydroxyflavones were prepared to evaluate the contribution of the B ring of baicalein (5,6,7-trihydroxyflavone, 1) to its potent α-glucosidase inhibitory activity. Hydroxychromones, which lack 6-hydroxyl substitution, did not show any inhibitory activity, while 5,6,7-trihydroxy-2-methylchromone (5) showed high activity. Among the tested B-ring-substituted 5,6,7-trihydroxyflavones, the 4′-hydroxy-, 3′,4′-dihydroxy-, and 3′,4′,5′- trihydroxy-substituted derivatives were found to give more activity than that of 1. The methoxy-substituted derivatives, however, showed less activity than 1. The results suggest that the B ring of 1 was not essential, although advantageous to the activity; hydroxyl substitution on the B ring of 5,6,7-trihydroxyflavones was favorable to the activity, whereas methoxyl substitution was unfavorable; at least 4′-hydrosyl substitution of 5,6,7-trihydroxyflavones was required for enhanced activity, in which the number of hydroxyl groups did not take part.

Synthesis of sinensetin, a naturally occurring polymethoxyflavone

5, 6, 7, 3′, 4′-Pentamethoxyflavone (8) isolated from the leaves of Orthosiphon stamineus has been synthesized by following an unambiguous route. All the new products have been characterised on the basis of spectral data and microanalysis.

Syntheses of 6-Hydroxyluteolin and Sinensetin by Wessely - Moser Rearrangement

Syntheses of 6-hydroxyluteolin (1) and sinensetin (2) are described.The compounds 6 and 7 afford 1 on Wessely - Moser rearrangement.The synthetic samples 1 and 2 are identical (m.m.p. and co-ir) with the authentic samples.

TLC, UV AND ACIDIC TREATMENT IN THE DIFFERENTIATION OF 5,6- AND 5,8-DIHYDROXYFLAVONES, 3-METHOXYFLAVONES AND FLAVONOLS

UV and TLC techniques constitute easy procedures to distinguish between 5,6-dihydroxy-7,8-dimethoxy- and 5,8-dihydroxy-6,7-dimethoxyflavonoids, that are difficult to characterize by NMR and classical UV techniques.The acidic treatment of the original products to obtain Wessely-Moser isomers, useful for comparison purposes, yielded novel demethylated products.UV and MS data of 5,8,4' -trihydroxy-6,7,3'-trimethoxyflavone, 5,6,8,3',4'-pentahydroxy-7-methoxyflavone and 5,6,8,4'-tetrahydroxy-7,3'-dimethoxyflavone are presented for the first time.