Isorhamnetin-3-O-beta-D-Glucoside

Details:

Chemical Properties of Isorhamnetin-3-O-beta-D-Glucoside

Cas No.	5041-82-7
PubChem ID	5318645	Appearance	Yellow powder
Formula	C22H22O12	M.Wt	478.40
Type of Compound	Flavonoids	Storage	Desiccate at -20°C
Solubility	DMSO : 250 mg/mL (522.58 mM; Need ultrasonic)
Chemical Name	5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES	COC1=C(C=CC(=C1)C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey	CQLRUIIRRZYHHS-LFXZADKFSA-N
Standard InChI	InChI=1S/C22H22O12/c1-31-12-4-8(2-3-10(12)25)20-21(17(28)15-11(26)5-9(24)6-13(15)32-20)34-22-19(30)18(29)16(27)14(7-23)33-22/h2-6,14,16,18-19,22-27,29-30H,7H2,1H3/t14-,16-,18+,19-,22+/m1/s1
General tips	For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging	1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment.
Shipping Condition	Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Isorhamnetin-3-O-beta-D-Glucoside

The herbs of Typha orientalis Presl.

Biological Activity of Isorhamnetin-3-O-beta-D-Glucoside

Description	Isorhamnetine-3-O-rutinoside inhibits the activity of alpha-glucosidase from rat intestine; it exhibits a potent rat lens aldose reductase (RLAR) inhibition in vitro, its IC(50) being 1.4 microM and has inhibitory effects of sorbitol accumulation, suggests that it is a leading compound for further study as a new drug for the prevention and/or treatment of diabetes and its complications.
Targets	IL Receptor
In vitro	Inhibitory effects of isorhamnetin-3-O-beta-D-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues.[Pubmed: 15863906] Biol Pharm Bull. 2005 May;28(5):916-8. The inhibitory effects of compounds from Salicornia herbacea (Chenopodiaceae) on rat lens aldose reductase (RLAR) and sorbitol accumulation in streptozotocin-induced diabetic rat tissues were investigated. METHODS AND RESULTS: The various fractions from the MeOH extract of S. herbacea were tested for their effects on RLAR in vitro. Among them, the EtOAc fraction was found to exhibit a potent RLAR inhibition (IC(50)=0.75 microg/ml), from which an active principle as a potent AR inhibitor was isolated and its chemical structure was elucidated as Isorhamnetin-3-O-beta-D-Glucoside (1) by spectral analysis. Compound 1 exhibited a potent RLAR inhibition in vitro, its IC(50) being 1.4 microM. Compound 1, when administered orally at 25 mg/kg in streptozotocin (STZ)-induced diabetic rats, caused not only a significant inhibition of serum glucose concentration but also sorbitol accumulation in the lenses, red blood cells (RBC), and sciatic nerves. CONCLUSIONS: These results indicate that compound 1 from S. herbacea is a leading compound for further study as a new drug for the prevention and/or treatment of diabetes and its complications. A review of chemistry and biological activities of the genus Aerva--a desert plant.[Pubmed: 22568031] Acta Pol Pharm. 2012 Mar-Apr;69(2):171-7. There are approximately 28 species of Aerva genus, but only a few species are medicinal of which A. persica, A. lanata and A. javanica are of great value. METHODS AND RESULTS: A number of flavonol glycosides (e.g., aervanone, kaempferol-3-galactoside, Isorhamnetin-3-O-beta-D-Glucoside) have been reported from Aerva persica as major phytoconstituents and the minor constituents are β-cyanins (glycine betaine and trigonelline), sterols and carbohydrates. This plant is used as medicinal herb in several traditional systems of medicine all over the world, like diuretic, demulcent, purgative, emetic and tinder. Aerva plants are used to cure ulcer, lithiasis, dropsical affections, eye affection, toothache, headache, in disorders of abdomen and inflammation of internal organs. CONCLUSIONS: Roots and flowers are reported to possess hypoglycemic, antioxidant, anthelmintic, analgesic, antimalarial, antivenin activities and medicinal properties against rheumatism and kidney troubles. Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity.[Pubmed: 18409066 ] J Nat Med. 2008 Jul;62(3):349-53. The dayflower, Commelina communis L., contains 1-deoxynojirimycin (DNJ) and (2R,3R,4R,5R)2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine (DMDP), potent alpha-glucosidase inhibitors. The extracts and powder of this herb are important food materials for prophylaxis against type 2 diabetes. METHODS AND RESULTS: Eleven flavonoid glycosides as antioxidants, isoquercitrin, isorhamnetin-3-O-rutinoside, Isorhamnetin-3-O-beta-D-Glucoside, glucoluteolin, chrysoriol-7-O-beta-D-glucoside, orientin, vitexin, isoorientin, isovitexin, swertisin, and flavocommelin, were identified from the aerial parts of C. communis. Their antioxidant activities were measured using in vitro assays employing the 1,1-diphenyl-2-picrylhydrazyl radical- and superoxide radical-scavenging assays. CONCLUSIONS: The results showed that glucoluteolin, orientin, isoorientin, and isoquercitrin are the predominant antioxidants in this herb. Moreover, isoquercitrin, isorhamnetine-3-O-rutinoside, vitexin, and swertisin inhibited the activity of alpha-glucosidase from rat intestine.

Protocol of Isorhamnetin-3-O-beta-D-Glucoside

Cell Research

Isolation of new cytotoxic metabolites from Cleome droserifolia growing in Egypt.[Pubmed: 22888531] Z Naturforsch C. 2012 May-Jun;67(5-6):266-74. The sulforhodamine B (SRB) assay was used to assess the cytotoxicity of the aqueous (AqEx) and ethanolic (AlEx) extracts, respectively, of the aerial parts of Cleome droserifolia (Forssk.) Del. against two human cancer cell lines, breast (MCF7) and colon (HCT116) adenocarcinoma. METHODS AND RESULTS: AqEx exhibited higher cytotoxic activity, thus its four subfractions, namely n-hexane (HxFr), chloroform (ClFr), ethyl acetate (EtFr), and n-butanol (BuFr) fractions, were also tested. Purification of the more active ClFr and EtFr yielded nine compounds. Six terpenoids, guai-7(11),8-diene (C1), 1-hydroxy-guai-3,10(14)-diene (C2), 18-hydroxydollabela-8(17)-ene (C3), (24E)-stigmasta-5,8-dien-3beta-ol (C4), teucladiol [1alpha,5beta-guai-10(14)-ene-4beta,6beta-diol] (C5), and buchariol (4,10-epoxy-6a-hydroxyguaiane) (C6), were isolated from ClFr and three flavonol glycosides, Isorhamnetin-3-O-beta-D-Glucoside (F1), quercetin-3'-methoxy-3-O-(4"-acetylrhamnoside)-7-O-alpha-rhamnoside (F2), and kaempferol-4'-methoxy-3,7-O-dirhamnoside (F3), were isolated from EtFr. Compounds C3 and F2 are new in nature. The isolated compounds were identified using various spectroscopic methods (UV, IR, 1H NMR, 13C NMR, HMQC, HMBC, and COSY). CONCLUSIONS: Compounds C1, C3, F2, and F3 showed significant cytotoxic activities against the two tested cell lines comparable to those of the anticancer drug doxorubicin. The new compound C3 was the most active as it had the lowest IC50 values, (1.9 +/- 0.08) and (1.6 +/- 0.09) microg/ml corresponding to 6.5 and 5.4 microM, against MCF7 and HCT116 cells, respectively.

Structure Identification

Molecules. 2012 Apr 17;17(4):4595-603. A new isorhamnetin glycoside and other phenolic compounds from Callianthemum taipaicum.[Pubmed: 22510608] A new flavonol glycoside together with five known phenolic compounds were isolated from the whole herb of Callianthemum taipaicum. METHODS AND RESULTS: The compounds were identified as isorhamnetin-3-O-α-L-arabinoside-7-O-β-D-glucoside (1), Isorhamnetin-3-O-beta-D-Glucoside(2), dibutyl phthalate (3), (+)-1-hydroxylpinoresinol-4'-β-D-glucoside (4), pinoresinol-4'-O-β-D-glucoside (5) and 2-phenylethyl-β-primeveroside (6). Compound 1 was identified as a new flavonol glycoside. The compound 6 was isolated for the first time as natural product. All compounds were isolated for the first time from the Callianthemum genus. Furthermore, the 2D-NMR data of the four known compounds 2-5 are given for the first time in this paper. CONCLUSIONS: All the structures were identified on the basis of detailed spectral analysis. The compounds 1 and 4 exhibited certain antifungal activity.

Preparing Stock Solutions of Isorhamnetin-3-O-beta-D-Glucoside

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.0903 mL	10.4515 mL	20.903 mL	41.806 mL	52.2575 mL
5 mM	0.4181 mL	2.0903 mL	4.1806 mL	8.3612 mL	10.4515 mL
10 mM	0.209 mL	1.0452 mL	2.0903 mL	4.1806 mL	5.2258 mL
50 mM	0.0418 mL	0.209 mL	0.4181 mL	0.8361 mL	1.0452 mL
100 mM	0.0209 mL	0.1045 mL	0.209 mL	0.4181 mL	0.5226 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

 

References on Isorhamnetin-3-O-beta-D-Glucoside

A review of chemistry and biological activities of the genus Aerva--a desert plant.[Pubmed:22568031]

Acta Pol Pharm. 2012 Mar-Apr;69(2):171-7.

There are approximately 28 species of Aerva genus, but only a few species are medicinal of which A. persica, A. lanata and A. javanica are of great value. A number of flavonol glycosides (e.g., aervanone, kaempferol-3-galactoside, Isorhamnetin-3-O-beta-D-Glucoside) have been reported from Aerva persica as major phytoconstituents and the minor constituents are beta-cyanins (glycine betaine and trigonelline), sterols and carbohydrates. This plant is used as medicinal herb in several traditional systems of medicine all over the world, like diuretic, demulcent, purgative, emetic and tinder. Aerva plants are used to cure ulcer, lithiasis, dropsical affections, eye affection, toothache, headache, in disorders of abdomen and inflammation of internal organs. Roots and flowers are reported to possess hypoglycemic, antioxidant, anthelmintic, analgesic, antimalarial, antivenin activities and medicinal properties against rheumatism and kidney troubles.

Antioxidant constituents in the dayflower (Commelina communis L.) and their alpha-glucosidase-inhibitory activity.[Pubmed:18409066]

J Nat Med. 2008 Jul;62(3):349-53.

The dayflower, Commelina communis L., contains 1-deoxynojirimycin (DNJ) and (2R,3R,4R,5R)2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine (DMDP), potent alpha-glucosidase inhibitors. The extracts and powder of this herb are important food materials for prophylaxis against type 2 diabetes. Eleven flavonoid glycosides as antioxidants, isoquercitrin, isorhamnetin-3-O-rutinoside, Isorhamnetin-3-O-beta-D-Glucoside, glucoluteolin, chrysoriol-7-O-beta-D-glucoside, orientin, vitexin, isoorientin, isovitexin, swertisin, and flavocommelin, were identified from the aerial parts of C. communis. Their antioxidant activities were measured using in vitro assays employing the 1,1-diphenyl-2-picrylhydrazyl radical- and superoxide radical-scavenging assays. The results showed that glucoluteolin, orientin, isoorientin, and isoquercitrin are the predominant antioxidants in this herb. Moreover, isoquercitrin, isorhamnetine-3-O-rutinoside, vitexin, and swertisin inhibited the activity of alpha-glucosidase from rat intestine.

Inhibitory effects of isorhamnetin-3-O-beta-D-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues.[Pubmed:15863906]

Biol Pharm Bull. 2005 May;28(5):916-8.

The inhibitory effects of compounds from Salicornia herbacea (Chenopodiaceae) on rat lens aldose reductase (RLAR) and sorbitol accumulation in streptozotocin-induced diabetic rat tissues were investigated. The various fractions from the MeOH extract of S. herbacea were tested for their effects on RLAR in vitro. Among them, the EtOAc fraction was found to exhibit a potent RLAR inhibition (IC(50)=0.75 microg/ml), from which an active principle as a potent AR inhibitor was isolated and its chemical structure was elucidated as Isorhamnetin-3-O-beta-D-Glucoside (1) by spectral analysis. Compound 1 exhibited a potent RLAR inhibition in vitro, its IC(50) being 1.4 microM. Compound 1, when administered orally at 25 mg/kg in streptozotocin (STZ)-induced diabetic rats, caused not only a significant inhibition of serum glucose concentration but also sorbitol accumulation in the lenses, red blood cells (RBC), and sciatic nerves. These results indicate that compound 1 from S. herbacea is a leading compound for further study as a new drug for the prevention and/or treatment of diabetes and its complications.

Isolation of new cytotoxic metabolites from Cleome droserifolia growing in Egypt.[Pubmed:22888531]

Z Naturforsch C. 2012 May-Jun;67(5-6):266-74.

The sulforhodamine B (SRB) assay was used to assess the cytotoxicity of the aqueous (AqEx) and ethanolic (AlEx) extracts, respectively, of the aerial parts of Cleome droserifolia (Forssk.) Del. against two human cancer cell lines, breast (MCF7) and colon (HCT116) adenocarcinoma. AqEx exhibited higher cytotoxic activity, thus its four subfractions, namely n-hexane (HxFr), chloroform (ClFr), ethyl acetate (EtFr), and n-butanol (BuFr) fractions, were also tested. Purification of the more active ClFr and EtFr yielded nine compounds. Six terpenoids, guai-7(11),8-diene (C1), 1-hydroxy-guai-3,10(14)-diene (C2), 18-hydroxydollabela-8(17)-ene (C3), (24E)-stigmasta-5,8-dien-3beta-ol (C4), teucladiol [1alpha,5beta-guai-10(14)-ene-4beta,6beta-diol] (C5), and buchariol (4,10-epoxy-6a-hydroxyguaiane) (C6), were isolated from ClFr and three flavonol glycosides, Isorhamnetin-3-O-beta-D-Glucoside (F1), quercetin-3'-methoxy-3-O-(4"-acetylrhamnoside)-7-O-alpha-rhamnoside (F2), and kaempferol-4'-methoxy-3,7-O-dirhamnoside (F3), were isolated from EtFr. Compounds C3 and F2 are new in nature. The isolated compounds were identified using various spectroscopic methods (UV, IR, 1H NMR, 13C NMR, HMQC, HMBC, and COSY). Compounds C1, C3, F2, and F3 showed significant cytotoxic activities against the two tested cell lines comparable to those of the anticancer drug doxorubicin. The new compound C3 was the most active as it had the lowest IC50 values, (1.9 +/- 0.08) and (1.6 +/- 0.09) microg/ml corresponding to 6.5 and 5.4 microM, against MCF7 and HCT116 cells, respectively.

A new isorhamnetin glycoside and other phenolic compounds from Callianthemum taipaicum.[Pubmed:22510608]

Molecules. 2012 Apr 17;17(4):4595-603.

A new flavonol glycoside together with five known phenolic compounds were isolated from the whole herb of Callianthemum taipaicum. The compounds were identified as isorhamnetin-3-O-alpha-L-arabinoside-7-O-beta-D-glucoside (1), Isorhamnetin-3-O-beta-D-Glucoside (2), dibutyl phthalate (3), (+)-1-hydroxylpinoresinol-4'-beta-D-glucoside (4), pinoresinol-4'-O-beta-D-glucoside (5) and 2-phenylethyl-beta-primeveroside (6). Compound 1 was identified as a new flavonol glycoside. The compound 6 was isolated for the first time as natural product. All compounds were isolated for the first time from the Callianthemum genus. Furthermore, the 2D-NMR data of the four known compounds 2-5 are given for the first time in this paper. All the structures were identified on the basis of detailed spectral analysis. The compounds 1 and 4 exhibited certain antifungal activity.

Description

Isorhamnetin-3-O-glucoside, a natural compound widely contained in many vegetables and rice, could be metabolized in intestinal microbiota after digestion.

Keywords:

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