Tuberosin

CAS# 41347-45-9

Tuberosin

2D Structure

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3D structure

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Tuberosin

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Chemical Properties of Tuberosin

Cas No. 41347-45-9 SDF Download SDF
PubChem ID 5318770 Appearance Powder
Formula C20H18O5 M.Wt 338.4
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (1~{R},13~{R})-7,7-dimethyl-8,12,20-trioxapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{14,19}]henicosa-2(11),3,5,9,14(19),15,17-heptaene-1,17-diol
SMILES CC1(C=CC2=CC3=C(C=C2O1)OC4C3(COC5=C4C=CC(=C5)O)O)C
Standard InChIKey ZBTYHECJEINCMD-QUCCMNQESA-N
Standard InChI InChI=1S/C20H18O5/c1-19(2)6-5-11-7-14-17(9-15(11)25-19)24-18-13-4-3-12(21)8-16(13)23-10-20(14,18)22/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/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 Tuberosin

The herbs of Pueraria tuberose

Biological Activity of Tuberosin

DescriptionTuberosin shows anti-inflammatory and antioxidant activities.It demonstrated a significantly potent inhibition on yeast α-glucosidase in a dose dependent manner.
Targetsα-glucosidase | NO | NOS
In vitro

Pueraria tuberosa: a review on its phytochemical and therapeutic potential.[Pubmed: 24980468 ]

Nat Prod Res. 2014;28(23):2111-27.

Pueraria tuberosa (Willd.) DC is a perennial herb commonly known as 'vidarikanda', distributed throughout south east Asia.
METHODS AND RESULTS:
The plant's tuber is widely used in ethanomedicine as well as in traditional systems of medicine, particularly in ayurveda. It has been used in various ayurvedic formulations as restorative tonic, antiaging, spermatogenic and immune booster and has been recommended for the treatment of cardiovascular diseases, hepatosplenomegaly, fertility disorders, menopausal syndrome, sexual debility and spermatorrhoea. Numerous bioactive phytochemicals, mostly isoflavonoids such as puerarin, genistein, daidzein, Tuberosin and so on have been identified in the tuber. In vivo and in vitro studies have provided the support against traditional demands of the tuber as spermatogenic, immune booster, aphrodisiac, anti-inflammatory, cardiotonic and brain tonic. However, further studies are required to define the active phytochemical compositions and to validate its clinical utilisation in the herbal formulations for human uses.
CONCLUSIONS:
This review provides an overview of traditional applications, current knowledge on the phytochemistry, pharmacology and toxicology of P. tuberosa. This review also provides plausible hypotheses about how various isoflavones particularly puerarin, genistein and daidzein, individually or collectively, may be responsible for the therapeutic potential against a wide range of ailments.

Antioxidant activity of tuberosin isolated from Pueraria tuberose Linn.[Pubmed: 20836891]

J Inflamm (Lond). 2010 Sep 14;7:47.

Antioxidant activity of Pueraria tuberose DC, (PT) Leguminosae (Fabaceae) has already been reported by us and here an active compound has been isolated and its action on expression of iNOS protein has been explored by using LPS induced changes in attached rat peritoneal macrophage cell culture.
METHODS AND RESULTS:
The pure compound was isolated by column chromatography and its structure was characterized by spectral studies, which was identified as Tuberosin (5 hydroxy 3,4,7,3',4' pentamethoxy flavone). Its antioxidant capacity was determined and compared with alcoholic extract as EC50 value for scavenging potential towards pre-generated monocation ABTS* radical, superoxide radicals, hydroxyl radicals, metal chelation property and on lipid peroxidation. Further, rat peritoneal macrophages were isolated, cultured and the attached macrophages were exposed to lipopolysaccharide (LPS) with different concentrations of Tuberosin (pretreatment for 30 min). After 17 h the released NO content, in culture supernatant, was indirectly estimated as accumulated nitrite by Griess reagent. To understand the mechanism of action, the extent of expression of inducible nitric oxide synthase genes, the iNOS protein was assessed in macrophage lysate by using its antibody on western blot analysis. Tuberosin significantly scavenged all the species of FRs, described above and it also inhibited the LPS induced release of NO and amount of iNOS protein in macrophages. All the changes were significant and concentration dependent.
CONCLUSIONS:
Thus it could be suggested that Tuberosin, is one of the active principles of Pueraria tuberose, which directly scavenges various species of Free radicals (FRs) and also inhibits LPS induced inflammatory changes in macrophages.

Protocol of Tuberosin

Kinase Assay

Yeast α-glucosidase inhibition by isoflavones from plants of Leguminosae as an in vitro alternative to acarbose.[Pubmed: 20734984 ]

J Agric Food Chem. 2010 Sep 22;58(18):9988-93.


METHODS AND RESULTS:
In the course of searching for new classes of α-glucosidase inhibitors originated from natural resources, 11 kinds of isoflavones, i.e., medicarpin (1), formononetin (2), mucronulatol (3), (3R)-calussequinone (5), (3R)-5'-methoxyvestitol (6), tectorigenin (7), biochanin A (8), Tuberosin (9), calycosin (10), daidzein (11), and genistein (12), as well as a flavone, liquritigenin (4), were isolated as active principles responsible for the yeast α-glucosidase inhibitory activity from two leguminous plant extracts, i.e., the heartwood extract of Dalbergia odorifera and the roots extract of Pueraria thunbergiana.
CONCLUSIONS:
Each components (1-12) demonstrated a significantly potent inhibition on yeast α-glucosidase in a dose dependent manner when the p-nitrophenyl-α-D-glucopyranoside was used as a substrate in vitro. The concentration required for 50% enzyme inhibition (IC50) were calculated as 2.93 mM (1), 0.51 mM (2), 3.52 mM (7) 0.35 mM (8), 3.52 mM (9), 0.85 mM (11), and 0.15 mM (12) when that of reference drug acarbose was evaluated as 9.11 mM, in vitro. However, isoflavone glycosides, i.e., puerarin (13), daidzin (14), formononetin-7-O-β-glucopyranoside (15), and genistin (16), exhibited a relatively poor inhibitory activity on yeast α-glucosidase as compared with the corresponding isoflavone (2, 11, 12), respectively.

Tuberosin Dilution Calculator

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Preparing Stock Solutions of Tuberosin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9551 mL 14.7754 mL 29.5508 mL 59.1017 mL 73.8771 mL
5 mM 0.591 mL 2.9551 mL 5.9102 mL 11.8203 mL 14.7754 mL
10 mM 0.2955 mL 1.4775 mL 2.9551 mL 5.9102 mL 7.3877 mL
50 mM 0.0591 mL 0.2955 mL 0.591 mL 1.182 mL 1.4775 mL
100 mM 0.0296 mL 0.1478 mL 0.2955 mL 0.591 mL 0.7388 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 Tuberosin

Antioxidant activity of tuberosin isolated from Pueraria tuberose Linn.[Pubmed:20836891]

J Inflamm (Lond). 2010 Sep 14;7:47.

Antioxidant activity of Pueraria tuberose DC, (PT) Leguminosae (Fabaceae) has already been reported by us and here an active compound has been isolated and its action on expression of iNOS protein has been explored by using LPS induced changes in attached rat peritoneal macrophage cell culture. The pure compound was isolated by column chromatography and its structure was characterized by spectral studies, which was identified as Tuberosin (5 hydroxy 3,4,7,3',4' pentamethoxy flavone). Its antioxidant capacity was determined and compared with alcoholic extract as EC50 value for scavenging potential towards pre-generated monocation ABTS* radical, superoxide radicals, hydroxyl radicals, metal chelation property and on lipid peroxidation. Further, rat peritoneal macrophages were isolated, cultured and the attached macrophages were exposed to lipopolysaccharide (LPS) with different concentrations of Tuberosin (pretreatment for 30 min). After 17 h the released NO content, in culture supernatant, was indirectly estimated as accumulated nitrite by Griess reagent. To understand the mechanism of action, the extent of expression of inducible nitric oxide synthase genes, the iNOS protein was assessed in macrophage lysate by using its antibody on western blot analysis. Tuberosin significantly scavenged all the species of FRs, described above and it also inhibited the LPS induced release of NO and amount of iNOS protein in macrophages. All the changes were significant and concentration dependent. Thus it could be suggested that Tuberosin, is one of the active principles of Pueraria tuberose, which directly scavenges various species of Free radicals (FRs) and also inhibits LPS induced inflammatory changes in macrophages.

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