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480-19-3 Usage

Description

Isorhamnetin is a flavonoid, which occurs naturally in plants and it is also a metabolite of quercetin. Isorhamnetin has anti-inflammatory effect as it can reduce the formation of large amounts of nitric oxide by the inhibition the activation of nuclear factor-κB (NF-κB), which is a significant transcription factor for inducible nitric oxide synthase.? Isorhamnetin is also reported to have effect in inducing the expression of neurofilaments, and it potentiated the NGF-induced neurite outgrowth and neurofilament expression, which could be a new direction in searching potential candidates as new drugs or food supplements for neurodegenerative diseases.

References

[1] Mari H?m?l?inen, Riina Nieminen, Pia Vuorela, Marina Heinonen and Eeva Moilanen, Anti-Inflammatory Effects of Flavonoids: Genistein, Kaempferol, Quercetin, and Daidzein Inhibit STAT-1 and NF-κB Activations, Whereas Flavone, Isorhamnetin, Naringenin, and Pelargonidin Inhibit only NF-κB Activation along with Their Inhibitory Effect on iNOS Expression and NO Production in Activated Macrophages, Mediators of Inflammation, 2007, vol. 2007, Article ID 45673 [2] Sherry L. Xu, Roy C. Y. Choi, Kevin Y. Zhu, Ka-Wing Leung, Ava J. Y. Guo, Dan Bi, Hong Xu, David T. W. Lau, Tina T. X. Dong and Karl W. K. Tsim, Isorhamnetin, A Flavonol Aglycone from Ginkgo biloba L., Induces Neuronal Differentiation of Cultured PC12 Cells: Potentiating the Effect of Nerve Growth Factor, Evidence-Based Complementary and Alternative Medicine, 2012, vol. 2012, Article ID 278273

Chemical Properties

Beige to lighet yellow powder

Uses

Different sources of media describe the Uses of 480-19-3 differently. You can refer to the following data:
1. A metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways.
2. Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 μM). Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 μM), which has an important role in the excretion of xenobiotics at the kidney and liver. It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects.
3. Reference Standard in the analysis of herbal medicinal products

Definition

ChEBI: Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3' is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It derives from a quercetin. It is a conjugate acid of an isorhamnetin(1-).

General Description

Isorhamnetin is one of the important flavanols found in G.biloba leaf extracts. Isorhamnetin is also found in parsley, and thereby it is a common dietary flavonoid as the metabolite of quercetin.Generally, it is well known as antagonist of peroxisome proliferator-activated receptor Y (PPARy), which inhibits adipocyte differentiation induced by the PPARy agonist rosiglitazone. Isorhamnetin is a naturally occurring compound in fruits and vegetables; recent study showed that isorhamnetin could significantly inhibit the invasion of MDA-MB-231 cells by downregulating matrix metalloproteinases(MMP-2 and MMP-9) through inhibiting p38 MAPK and STAT3. Similar results were also obtained in another study, which showed that isorhamnetin inhibited cell proliferation and led to apoptosis. In addition, isorhamnetin was found effective on Akt/mTOR/MAPKs signaling axis. It was established that isorhamnetin-induced autophagy can be reversed by the co-treatment of 3-methyl-adenine in lung cancer cells. The results indicated that isorhamnetin exerts antitumor effect in breast cancer through targeting multiple molecular targets.

Biochem/physiol Actions

Isorhamnetin inhibits adipogenesis by interfering with differentiation of adipose stem cells, by a mechanism involving stabilization of β-catenin and up-regulating the Wnt signaling pathway.

Check Digit Verification of cas no

The CAS Registry Mumber 480-19-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 0 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 480-19:
(5*4)+(4*8)+(3*0)+(2*1)+(1*9)=63
63 % 10 = 3
So 480-19-3 is a valid CAS Registry Number.
InChI:InChI=1/C16H12O7/c1-22-11-4-7(2-3-9(11)18)16-15(21)14(20)13-10(19)5-8(17)6-12(13)23-16/h2-6,17-19,21H,1H3

480-19-3 Well-known Company Product Price

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  • Sigma-Aldrich

  • (38907)  Isorhamnetin  analytical standard

  • 480-19-3

  • 38907-10MG

  • 4,661.28CNY

  • Detail
  • USP

  • (1351800)  Isorhamnetin  United States Pharmacopeia (USP) Reference Standard

  • 480-19-3

  • 1351800-15MG

  • 5,103.54CNY

  • Detail
  • Sigma-Aldrich

  • (04290585)  Isorhamnetin  primary pharmaceutical reference standard

  • 480-19-3

  • 04290585-10MG

  • 6,745.05CNY

  • Detail

480-19-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name isorhamnetin

1.2 Other means of identification

Product number -
Other names 3'-O-Methyl Quercetin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:480-19-3 SDS

480-19-3Synthetic route

4.2'.4'.6'-tetrahydroxy-3-methoxy-trans-chalcone
25515-47-3

4.2'.4'.6'-tetrahydroxy-3-methoxy-trans-chalcone

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With potassium hydrogensulfate; sodium hydrogencarbonate; sodium carbonate In dichloromethane; water; acetone at 20℃; for 42h; pH=9;96.7%
3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxy-4H-chromen-4-one

3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxy-4H-chromen-4-one

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 4h;92%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 25℃; for 8h;90%
With palladium 10% on activated carbon; hydrogen In ethanol at 25℃;90%
With hydrogen; palladium dihydroxide In tetrahydrofuran; ethanol for 6h;85%
7-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)- 3,5-dihydroxy-4H-chromen-4-one
78386-02-4

7-(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)- 3,5-dihydroxy-4H-chromen-4-one

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With 20% palladium hydroxide-activated charcoal In ethanol; cyclohexene for 1h; Inert atmosphere; Reflux;92%
With 10% palladium on activated carbon; hydrogen In ethanol at 20℃; for 5h;90%
isorhamnetin-3-O-glucoside
6743-92-6, 50306-07-5, 5041-82-7

isorhamnetin-3-O-glucoside

A

D-Glucose
2280-44-6

D-Glucose

B

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogen cationA n/a
B 63%
With acid hydrolysis
2,3-dihydroisorhamnetin

2,3-dihydroisorhamnetin

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With potassium pyrosulfite In ethanol at 100℃; for 5h;55%
Conditions
ConditionsYield
With sulfuric acid; water In ethanolA n/a
B n/a
C 42%
With hydrogenchloride In water at 100℃;
With hydrogenchloride; water at 100℃; for 2h;
2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone
65490-09-7

2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone

vanillin
121-33-5

vanillin

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
Stage #1: 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone; vanillin With pyrrolidine; oxygen In water under 760.051 Torr;
Stage #2: With hydrogenchloride In methanol; water
41%
Conditions
ConditionsYield
With sodium azide; T133M and Y326R mutant of isoeugenol phenylpropanoid O-methyltransferase from Clarkia breweri In aq. buffer at 30℃; for 240h; pH=7.5; Reagent/catalyst; Enzymatic reaction; regioselective reaction;6.8%
With DL-dithiothreitol; recombinant Plagiochasma appendiculatum flavone 6-O-methyltransferase; magnesium chloride In aq. buffer at 37℃; for 0.5h; pH=7.5; Enzymatic reaction;
With Citrus reticulata O-methyltransferase gene-pET32a recombinant In aq. buffer at 37℃; for 2h; pH=8; Kinetics; Enzymatic reaction;
2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone
65982-77-6

2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

4-acetoxy-3-methoxy-benzoic acid-anhydride

4-acetoxy-3-methoxy-benzoic acid-anhydride

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With triethylamine at 160℃; Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge;
3,5,7,4′-tetrahydroxy-8,3′-dimethoxyflavone-3-O-β-D-glucopyranoside
103839-19-6, 38836-51-0

3,5,7,4′-tetrahydroxy-8,3′-dimethoxyflavone-3-O-β-D-glucopyranoside

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogen cation In water
Quercetin-7-O-monoglucoside
6743-96-0, 128331-43-1

Quercetin-7-O-monoglucoside

A

D-Glucose
2280-44-6

D-Glucose

B

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogenchloride for 4h;
quercetol
117-39-5

quercetol

A

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on
1486-70-0

2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-3-methoxy-chromen-4-on

B

tamarixetin
603-61-2

tamarixetin

C

5-O-methylquercetin
529-51-1

5-O-methylquercetin

D

isorhamnetin
480-19-3

isorhamnetin

E

rhamnetin
90-19-7

rhamnetin

Conditions
ConditionsYield
With O-methyl transferase from cell-free extract of Citrus mitis; <(14)CH3>-S-adenosyl-L-methionine; 2-hydroxyethanethiol In water; dimethyl sulfoxide at 35℃; for 0.5h; Product distribution; pH 7.5 buffer;
quercetin 3'-O-methyl ether 3-O-α-L-rhamnopyranosyl-(1'''→6
604-80-8, 3520-85-2, 24905-37-1, 53584-69-3, 62249-59-6, 145264-20-6, 107740-46-5

quercetin 3'-O-methyl ether 3-O-α-L-rhamnopyranosyl-(1'''→6")-β-D-galactopyranoside

A

D-Galactose
10257-28-0

D-Galactose

B

L-rhamnose
73-34-7

L-rhamnose

C

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With oxonium Product distribution;
3-<6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl>oxy-5-hydroxy-7-<β-L-mannopyranosyl>oxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzo-pyran-4-one
107603-09-8, 119945-81-2, 142784-28-9

3-<6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl>oxy-5-hydroxy-7-<β-L-mannopyranosyl>oxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzo-pyran-4-one

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With sulfuric acid at 90℃; for 0.5h;11 mg
isorhamnetin 3-O-rutinoside-4'-O-rhamnoside

isorhamnetin 3-O-rutinoside-4'-O-rhamnoside

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogenchloride In methanol
2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone
65982-77-6

2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

anhydride of/the/ O-benzoyl-vanillic acid

anhydride of/the/ O-benzoyl-vanillic acid

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With sodium-<4-benzoyloxy-3-methoxy benzoate> at 180 - 185℃; Kochen des Reaktionsprodukts mit waessrig-alkoholischer Kalilauge;
persicarin

persicarin

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogenchloride
isorhamnetin 3-O-(6''-E-p-coumaroyl-β-D-glucopyranoside)-7-O-β-D-glucopyranoside

isorhamnetin 3-O-(6''-E-p-coumaroyl-β-D-glucopyranoside)-7-O-β-D-glucopyranoside

A

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

B

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogenchloride at 100℃; for 1h;
isorhamnetin 3,7-O-di-β-D-glucopyranoside
6758-51-6

isorhamnetin 3,7-O-di-β-D-glucopyranoside

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With sulfuric acid In methanol for 3h; Heating;220 mg
isorhamnetin-3-O-glucoside
6743-92-6, 50306-07-5, 5041-82-7

isorhamnetin-3-O-glucoside

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
Acid hydrolysis;
Conditions
ConditionsYield
Acid hydrolysis;
With hydrogenchloride at 100℃; for 1h;
Conditions
ConditionsYield
With McIlvaine buffer; flavonol-3-O-β-heterodisaccharide glycosidase at 30℃; for 0.25h; pH=5.0; Enzyme kinetics;
quercetol
117-39-5

quercetol

AdoMet

AdoMet

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With DL-dithiothreitol; HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.5; Enzyme kinetics; Enzymatic reaction;
With DL-dithiothreitol; HCl buffer; 2-amino-2-hydroxymethyl-1,3-propanediol at 37℃; for 1h; pH=7.5; Enzymatic reaction;
3,7-bis(benzyloxy)-2-[4-(benzyloxy)-3-hydroxyphenyl]-5-hydroxy-4H-1-benzopyran-4-one
40554-92-5

3,7-bis(benzyloxy)-2-[4-(benzyloxy)-3-hydroxyphenyl]-5-hydroxy-4H-1-benzopyran-4-one

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / K2CO3 / dimethylformamide
2: 85 percent / H2 / 10 percent Pd(OH)2 / ethanol; tetrahydrofuran / 6 h
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 25 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; ethanol / 8 h / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 25 °C
2: palladium 10% on activated carbon; hydrogen / ethanol / 25 °C
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 0.08 h / 0 °C / Inert atmosphere
1.2: 15 h / 20 °C / Inert atmosphere
2.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 4 h / 20 °C
View Scheme
3-methoxy-4-acetoxybenzoyl chloride
56681-66-4

3-methoxy-4-acetoxybenzoyl chloride

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine; H2O
2: triethylamine / 160 °C / Erwaermen des Reaktionsprodukts mit wss.-aethanol. Kalilauge
View Scheme
3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; hydrogen chloride / Kochen des Reaktionsprodukts mit Alkohol
2: sodium salt of/the/ O-benzoyl-vanillic acid / 180 - 185 °C / Kochen des Reaktionsprodukts mit waessrig-alkoholischer Kalilauge
View Scheme
isorhamnetin 3-O-[-α-L-rhamnopyranosyl-(1->3)]-β-D-glucopyranoside

isorhamnetin 3-O-[-α-L-rhamnopyranosyl-(1->3)]-β-D-glucopyranoside

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With hydrogenchloride; water In methanol for 4h; Reflux;
isorhamnetin 7-O-β-D-glucopyranoside
128331-43-1, 6743-96-0

isorhamnetin 7-O-β-D-glucopyranoside

A

D-glucose
50-99-7

D-glucose

B

isorhamnetin
480-19-3

isorhamnetin

Conditions
ConditionsYield
With water Acidic conditions;
uridine 5'-diphospho-D-galactose
2956-16-3

uridine 5'-diphospho-D-galactose

isorhamnetin
480-19-3

isorhamnetin

isorhamnetin 3-β-D-galactopyranoside
5041-82-7, 6743-92-6, 50306-07-5

isorhamnetin 3-β-D-galactopyranoside

Conditions
ConditionsYield
With 3-O-glycosyltransferase from Scutellaria baicalensis In dimethyl sulfoxide at 45℃; for 4h; pH=9; Enzymatic reaction; regiospecific reaction;83%
isorhamnetin
480-19-3

isorhamnetin

isorhamnetin 3-O-N-acetylglucosamine

isorhamnetin 3-O-N-acetylglucosamine

Conditions
ConditionsYield
With 3-O-glycosyltransferase from Scutellaria baicalensis In dimethyl sulfoxide at 45℃; for 4h; pH=9; Enzymatic reaction; regiospecific reaction;75%
isorhamnetin
480-19-3

isorhamnetin

C16H9(2)H3O7

C16H9(2)H3O7

Conditions
ConditionsYield
Stage #1: isorhamnetin With [D]-sodium hydroxide; platinum on activated charcoal; water-d2 at 130℃; for 9h; Inert atmosphere;
Stage #2: With formic acid at 130℃; for 1h; Inert atmosphere;
75%
3-methoxy-4-hydroxybenzoic acid
121-34-6

3-methoxy-4-hydroxybenzoic acid

isorhamnetin
480-19-3

isorhamnetin

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

UDP-glucose
133-89-1

UDP-glucose

isorhamnetin
480-19-3

isorhamnetin

isorhamnetin-3-O-glucoside
6743-92-6, 50306-07-5, 5041-82-7

isorhamnetin-3-O-glucoside

Conditions
ConditionsYield
With UDP glucose:flavonol glucosyltransferase enzyme preparation from Norway spruce needles In water for 0.75h; pH 8.0 bicine buffer;
With Populus deltoids Marsh PGT-3 at 37℃; for 0.5h; pH=7.5; Kinetics; Reagent/catalyst; aq. phosphate buffer; Enzymatic reaction; regioselective reaction;
isorhamnetin
480-19-3

isorhamnetin

potash

potash

A

3,5-dihydroxyphenol
108-73-6

3,5-dihydroxyphenol

B

3,4-Dihydroxybenzoic acid
99-50-3

3,4-Dihydroxybenzoic acid

Conditions
ConditionsYield
beim Schmelzen;
hydrogen iodide
10034-85-2

hydrogen iodide

isorhamnetin
480-19-3

isorhamnetin

quercetol
117-39-5

quercetol

isorhamnetin
480-19-3

isorhamnetin

quercetin-3'-methyl ether-3.5.7.4'-tetraacetate

quercetin-3'-methyl ether-3.5.7.4'-tetraacetate

Conditions
ConditionsYield
Acetylieren;
methanol
67-56-1

methanol

isorhamnetin
480-19-3

isorhamnetin

methyl iodide
74-88-4

methyl iodide

quercetin-3.7.3'.4'-tetramethyl ether

quercetin-3.7.3'.4'-tetramethyl ether

480-19-3Relevant articles and documents

Flavonoid glycosides from seeds of Hippophae rhamnoides subsp. Sinensis with α-glucosidase inhibition activity

Li, Rui,Wang, Qing,Zhao, Menghao,Yang, Peiming,Hu, Xiao,Ouyang, Danwei

, (2019)

Hippophae rhamnoides subsp. Sinensis is a famous traditional medicinal plant in Tibet and Mongolia of China. Three novel flavonoid glycosides and ten known analogues were obtained from the seeds of H. rhamnoides. The structures of new compounds were elucidated by spectroscopics, chemical methods as well as literature data. In vitro assay, compounds 5–9, kaempferol and 70% ethanolic elution fraction showed prominent α-glucosidase inhibitory activities with IC50 values ranging from 8.30 to 112.11 μM, better than that of the positive control, acarbose, whose IC50 value was 1727.07 μM.

-

Tsepkova et al.

, (1972)

-

Two new flavonol glycosides and biological activities of Diplotaxis harra (Forssk.) Boiss.

Kassem, Mona E.S.,Afifi, Manal S.,Marzouk, Mona M.,Mostafa, Manal A.

, p. 2272 - 2280 (2013)

Two new flavonol glycosides, isorhamnetin 3-O-β-glucopyranoside- 4′-O-β-xylopyranoside (1) and kaempferol 3-O-β-glucopyranoside -4′-O-β-xylopyranoside (2), were isolated from the defatted aqueous methanol extract of the whole plant Diplotaxis harra along with 12 known flavonols (3-14). They were characterised by chemical and spectral methods. The 70% aqueous methanol, chloroform and defatted aqueous methanol plant extracts exhibited significant antioxidant effects (nitroblue tetrazolium reduction method). Their cytotoxic activity was carried out against 11 tumour cell lines (sulphorhodamine B assay). The three extracts expressed the greatest antiproliferative activity against colon 38, P388 and MKN-28 with GI50 (0.45, 0.4, 0.07 g/mL) and against P388 [3-(4,5-dimethylthiazol-2yl)-2,5- diphenyltetrazolium bromide assay] with IC50 (0.26, 0.24, 0.25 g/mL), respectively. The chloroform extract showed the highest activity as eukaryotic DNA topoisomerase II inhibitors of P388 with IC50 0.24 g/mL. Antiviral screening of the extracts and the pure compounds against foot-and-mouth disease virus types A and O revealed a prominent inhibition of its cytopathic effect. 2013

FLAVONOL GLYCOSIDES FROM SEDUM ACRE

Wolbis, Maria,Krolikowska, Maria

, p. 3941 - 3944 (1988)

Three new flavonol glycosides, isohamnetin 3-(2''-acetyl) glucoside, limocitrin 7-glucoside, and limocitrin 3,7-diglucoside were isolated from the aerial parts of Sedum acre.The known compounds quercetin, isohamnetin and their 3- and 3,7-di-glucosides, isohamnetin-7-glucoside an d limocitrin and its 3-glucoside were also identified.The structure of the compounds was determined by means of spectroscopic and chemical methods.

Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids

Tang, Qingyun,Vianney, Yoanes M.,Weisz, Klaus,Grathwol, Christoph W.,Link, Andreas,Bornscheuer, Uwe T.,Pavlidis, Ioannis V.

, p. 3721 - 3727 (2020/06/02)

Methylation of free hydroxyl groups is an important modification for flavonoids. It not only greatly increases absorption and oral bioavailability of flavonoids, but also brings new biological activities. Flavonoid methylation is usually achieved by a specific group of plant O-methyltransferases (OMTs) which typically exhibit high substrate specificity. Here we investigated the effect of several residues in the binding pocket of the Clarkia breweri isoeugenol OMT on the substrate scope and regioselectivity against flavonoids. The mutation T133M, identified as reported in our previous publication, increased the activity of the enzyme against several flavonoids, namely eriodictyol, naringenin, luteolin, quercetin and even the isoflavonoid genistein, while a reduced set of amino acids at positions 322 and 326 affected both, the activity and the regioselectivity of the methyltranferase. On the basis of this work, methylated flavonoids that are rare in nature were produced in high purity.

Chemical composition and biological activity of salicornia fruticosa L.

Abdel Elatif,Shabana,Ibrahim,Mansour,Awad,Sharaf

, p. 1713 - 1721 (2020/09/01)

Plants have been used as a source of traditional medicine to treat many diseases and conditions for many years. They considered as excellent source of phytochemicals which showed antioxidant and anticancer activities. The aim of the present study is to investigate the chemical composition and to determine the anticancer activity of Salicornia fruticosa (Chenopodiaceae) methanolic extract. S. fruticosa proved to be a source of isorhamnetin and its glycosides and showed anticancer activities. Seven major flavonoids were isolated and identified from the cytotoxic methanolic extract. The isolated compounds were identified, as quercetin 3',4'-dimethyl ether (1), isorhamnetin (2), isorhamnetin 3-O-rhamnoside (3), isorhamnetin 3-O-glucoside (4), isorhamnetin 3-O-rutinoside (5), isorhamnetin 3-O-neohesperidoside (6), isorhamnetin 3-O-rhamnosyl(1-2)arabinoside (7), by chromatographic analysis, chemical and spectroscopic tools (acid hydrolysis, UV, 1H and 13C NMR). Compounds 1 and 3-7 were isolated for the first time from the plant under investigation. The evaluation of cytotoxic activity of the methanolic extract against HCT-116, HepG2, A549 and MCF-7 human cancer cells, by MTT assay, revealed the higher potency of S. Fruticosa extract with IC50 [2.6. 10.9, 37.9, 5.4 (mg/ml)] respectively, comparable to that of doxorubicin. The obtained results suggested that the investigated plant could be used for future development of naturally occurring anticancer agent. Subclinical and clinical trials on polar fractions of S. fruticosa are mandatory to pave the way for its use in treatment of cancer diseases (HCT-116, HepG2, A549 and MCF-7).

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