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Demethoxysudachitin

CAS# 4323-80-2

Demethoxysudachitin

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Chemical structure

Demethoxysudachitin

3D structure

Chemical Properties of Demethoxysudachitin

Cas No. 4323-80-2 SDF Download SDF
PubChem ID 3083845 Appearance Yellow powder
Formula C17H14O7 M.Wt 330.29
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 5,7-dihydroxy-2-(4-hydroxyphenyl)-6,8-dimethoxychromen-4-one
SMILES COC1=C(C(=C2C(=C1O)C(=O)C=C(O2)C3=CC=C(C=C3)O)OC)O
Standard InChIKey SYGUVOLSUJYPPS-UHFFFAOYSA-N
Standard InChI InChI=1S/C17H14O7/c1-22-16-13(20)12-10(19)7-11(8-3-5-9(18)6-4-8)24-15(12)17(23-2)14(16)21/h3-7,18,20-21H,1-2H3
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.

Demethoxysudachitin Dilution Calculator

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Demethoxysudachitin Molarity Calculator

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Preparing Stock Solutions of Demethoxysudachitin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0276 mL 15.1382 mL 30.2764 mL 60.5528 mL 75.6911 mL
5 mM 0.6055 mL 3.0276 mL 6.0553 mL 12.1106 mL 15.1382 mL
10 mM 0.3028 mL 1.5138 mL 3.0276 mL 6.0553 mL 7.5691 mL
50 mM 0.0606 mL 0.3028 mL 0.6055 mL 1.2111 mL 1.5138 mL
100 mM 0.0303 mL 0.1514 mL 0.3028 mL 0.6055 mL 0.7569 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.

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References on Demethoxysudachitin

Endothelium-Independent Vasorelaxant Effects of Sudachitin and Demethoxysudachitin, Polymethoxyflavone from the Peel of Citrus sudachi on Isolated Rat Aorta.[Pubmed:37914361]

Biol Pharm Bull. 2023;46(11):1583-1591.

Although polymethoxyflavones have been reported to exhibit various pharmacological actions, the effects of polymethoxyflavones sudachitin and Demethoxysudachitin from the peel of Citrus sudachi on the cardiovascular system have not been clarified. This study investigated the mechanisms of vasorelaxation induced by sudachitin and Demethoxysudachitin in rat aorta. Both compounds inhibited phenylephrine-induced contractions in a concentration-dependent manner. This was also observed in the case of potassium chloride (KCl)-induced contractions although the inhibitory effect was weak. In both contraction types, no differences were found in the inhibitory effects of sudachitin and Demethoxysudachitin between endothelium-intact and -denuded aorta. The relaxant effects of sudachitin in endothelium-intact aortas were not affected by the nitric oxide synthase inhibitor N-nitro-L-arginine methyl ester hydrochloride (L-NAME) or the cyclooxygenase inhibitor indomethacin. In endothelium-denuded aorta, propranolol did not affect the relaxant effect of sudachitin. Both the adenylate cyclase activator forskolin- and soluble guanylate cyclase activator sodium nitroprusside-induced relaxant effects were potentiated by preincubation of sudachitin. Furthermore, the relaxant effect of sudachitin was not affected by the adenylate and guanylate cyclase inhibitors SQ22536 and or 1H-[1,2,4]Oxadiazolo[4,3-a]quinoxaline-1-one (ODQ), respectively. Finally, we examined the effect of phosphodiesterase inhibition. Phosphodiesterase inhibitors (3-isobutyl-1-methylxanthine, cilostamide or sildenafil) alone, sudachitin alone, and a combination of phosphodiesterase inhibitors with sudachitin exhibited relaxant effects, while the lack of any interaction between each phosphodiesterase inhibitor and sudachitin indicated an additive effect between the two substance categories. These results suggest that sudachitin and Demethoxysudachitin cause endothelial-independent relaxation, and that the mechanism of vasorelaxation by sudachitin is associated with the enhancement of cAMP- and guanosine 3',5'-cyclic monophosphate (cGMP)-dependent pathways.

Effects of polymethoxyflavonoids on T helper 17 cell differentiation in vitro and in vivo.[Pubmed:37164715]

J Med Invest. 2023;70(1.2):166-170.

We examined the effects of polymethoxyflavonoids (PMFs) on T helper (Th) 17 cell differentiation in vitro and in vivo. Five different PMFs including nobiletin (NOB), sudachitin (SUD), Demethoxysudachitin, heptamethoxyflavone and natsudaidain were used for the in vitro study, and effects of those flavonoids on Th17 responses were investigated. NOB and heptamethoxyflavone significantly suppressed the proliferation response, but SUD, Demethoxysudachitin and natsudaidain did not suppress the proliferation response. All of the five flavonoids decreased IL-17A production. Mice with experimentally induced autoimmune encephalomyelitis were used as an in vivo Th17 differentiation model. We focused on two flavonoids, NOB and SUD, and examined the effects of those flavonoids. NOB significantly suppressed Th17 cell proliferation and cytokine responses, but SUD only decreased proliferation responses. The results suggest that the suppressive effect of NOB on Th17 response in vivo is stronger than that of SUD. J. Med. Invest. 70 : 166-170, February, 2023.

Flavonoid compounds isolated from Tibetan herbs, binding to GABA(A) receptor with anxiolytic property.[Pubmed:33246118]

J Ethnopharmacol. 2021 Mar 1;267:113630.

ETHNOPHARMACOLOGICAL RELEVANCE: Previously, the phytochemical constituents of Biebersteinia heterostemon Maxim (BHM) and Arenaria kansuensis Maxim (AKM) were studied and the evaluation of anxiolytic effect based on their extracts was also investigated. The two traditional Tibetan herbs, BHM and AKM, have been widely used in Qinghai-Tibet Plateau for cardiopulmonary disorders and neuropsychiatric diseases. The anxiolytic activities of a number of agents mediated by alpha2/3-containing GABA(A) receptors (GABA(A)Rs) have been demonstrated through the genetic and pharmacological studies. Flavonoids, such as flavones and flavanols, are a class of ligands that act at GABA(A)Rs and exhibit anxiolytic effects in vivo. Here, the flavonoids are the predominant constituents isolated from BHM and AKM. And our purpose is to investigate structure-activity relationships of the flavonoid compounds with binding to BZ-S of GABA(A)R complexes, and to search for anxiolytic constituents that lack undesirable-effects such as sedation and myorelaxation. MATERIALS AND METHODS: The flavonoid constituents were separated and purified through the repeatedly silica gel or/and C18 column chromatography. The affinities of the compounds for BZ-S of GABA(A)Rs were detected by the radioreceptor binding assay with bovine cerebellum membranes, in which the different recombinant subunits-containing GABA(A)Rs were expressed in HEK 293T cells. The behavior tests, including elevated plus maze, locomotor activity, holeboard, rotarod and horizontal wire, were used to determine and evaluate the anxiolytic, sedative, and myorelaxant effects of these flavonoids. RESULTS: Eleven total flavonoid compounds were obtained from the Tibetan herbs (BHM and AKM). The flavones with 6-and/or 8-OMe possessed the most potent binding affinity to GABA(A)Rs, which were based on the result of structure-activity relationships analysis. Demethoxysudachitin (DMS, K(i) = 0.59 muM), a flavone that binds to recombinant alpha1-3/5 subunit-containing GABA(A)Rs, was isolated from BHM, and exhibited high anxiolytic activity, without inducing sedation and myorelaxation. Moreover, the anxiolytic effect of DMS was antagonized by flumazenil, suggesting that a mode of action was mediated via the BZ-S of GABA(A)Rs. CONCLUSIONS: This present study indicated that the flavones, especially DMS, are novel GABA(A)R ligands and therapeutic potential candidates for anxiety.

Citrus peel polymethoxyflavones, sudachitin and nobiletin, induce distinct cellular responses in human keratinocyte HaCaT cells.[Pubmed:30185129]

Biosci Biotechnol Biochem. 2018 Dec;82(12):2064-2071.

A variety of polyphenols have been isolated from plants, and their biological activities have been examined. Sudachitin (5,7,4'-trihydroxy-6,8,3'-trimethoxyflavone) is a polymethoxyflavone that is isolated from the peel of Citrus sudachi. Although we previously reported that sudachitin possesses an anti-inflammatory activity, its other biological activities are not yet understood. In this study, we report a novel biological activity of sudachitin, which selectively induced apoptosis in human keratinocyte HaCaT cells. Another polymethoxyflavone, nobiletin (5,6,7,8,3',4'-hexamethoxyflavone), promoted autophagy but not apoptosis in HaCaT cells. On the other hand, 3'-Demethoxysudachitin (5,7,4'-trihydroxy-6,8-dimethoxyflavone) failed to induce apoptosis and autophagy. These results show that three polymethoxyflavones have different effects on apoptosis and autophagy in HaCaT cells. Understanding the structure and biological activity of polymethoxyflavones may lead to the discovery of potential candidates for cancer drug development without significant toxic side effects. Abbreviations: ROS: reactive oxygen species; DMSO: dimethyl sulfoxide; MTT: 3-(4, 5-dimethylthiazol-2yl)-2, 5-diphenyltetrazolium bromide; GAPDH: glyceraldehyde-3-phosphate dehydrogenase; PARP: poly(ADP-ribose) polymerase; PI: propidium iodide; MAPK: mitogen-activated protein kinase.

Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones.[Pubmed:18053332]

J Pharm Pharmacol. 2007 Dec;59(12):1697-701.

Flavonoids are constituents of the human diet (they are present in many beverages and food), and in organisms they are responsible for several biological functions, including that of antioxidant. Because of the increasing interest in these molecules, methods for their synthesis and structural modification are of great importance; studies on the biological activities of many of these compounds are insufficient because of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available and inexpensive flavanones, using a bromination-methoxylation procedure. A series of flavonoids that are not otherwise accessible can be prepared using this method. As an example, 3'-Demethoxysudachitin, a limited flavone possessing antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori and acting as a 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenger, was prepared in fairly satisfactory yield.

Chemical constituents from the peels of Citrus sudachi.[Pubmed:16933871]

J Nat Prod. 2006 Aug;69(8):1177-9.

A methanol extract of the peels of Citrus sudachi gave five new compounds (1-5) and 27 known compounds. The structures were elucidated on the basis of spectroscopic evidence. Several of these compounds were assayed for antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori, and sudachitin (6) and 3'-Demethoxysudachitin (7) were the most active.

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