Tripdiolide

CAS# 38647-10-8

Tripdiolide

Catalog No. BCN5985----Order now to get a substantial discount!

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Quality Control of Tripdiolide

Number of papers citing our products

Chemical structure

Tripdiolide

3D structure

Chemical Properties of Tripdiolide

Cas No. 38647-10-8 SDF Download SDF
PubChem ID 294491 Appearance White cryst.
Formula C20H24O7 M.Wt 376.40
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC(C)C12C(O1)C3C4(O3)C5(CC(C6=C(C5CC7C4(C2O)O7)COC6=O)O)C
Standard InChIKey PUJWFVBVNFXCHZ-SQEQANQOSA-N
Standard InChI InChI=1S/C20H24O7/c1-7(2)18-13(26-18)14-20(27-14)17(3)5-10(21)12-8(6-24-15(12)22)9(17)4-11-19(20,25-11)16(18)23/h7,9-11,13-14,16,21,23H,4-6H2,1-3H3/t9-,10-,11-,13-,14-,16+,17-,18-,19+,20+/m0/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 Tripdiolide

The herb of Tripterygium wilfordii Hook.f.

Biological Activity of Tripdiolide

DescriptionTripdiolide has cytotoxic, and anti-rheumatic activities, it suppresses pro-inflammatory gene expression, may be effective therapy for lupus nephritis.
TargetsTNF-α | IL Receptor
In vivo

Effective therapy for nephritis in (NZB x NZW)F1 mice with triptolide and tripdiolide, the principal active components of the Chinese herbal remedy Tripterygium wilfordii Hook F.[Pubmed: 18512813 ]

Arthritis Rheum. 2008 Jun;58(6):1774-83.

Triptolide and Tripdiolide are thought to be active components of the Chinese antirheumatic herbal remedy Tripterygium wilfordii Hook F, which has been shown to be effective in treating murine lupus nephritis. This study was undertaken to examine the therapeutic effect of triptolide and Tripdiolide on established lupus nephritis in (NZB x NZW)F1 mice.The mean level of anti-dsDNA antibody in mice treated with Tripdiolide was lower than that in the vehicle-treated mice upon completion of the treatment course. Production of tumor necrosis factor, interleukin-6, and monocyte chemoattractant protein 1 by spleen cells was also decreased after diterpenoid therapy.Therapy with triptolide or Tripdiolide significantly ameliorated lupus nephritis in (NZB x NZW)F1 mice, reduced cytokine and chemokine production, and prolonged survival.

Protocol of Tripdiolide

Structure Identification
Phytochem Anal. 2008 Jul-Aug;19(4):348-52.

Determination of tripdiolide in root extracts of Tripterygium wilfordii by solid-phase extraction and reversed-phase high-performance liquid chromatography.[Pubmed: 18288676]

Extracts of Tripterygium wilfordii Hook F. have been widely used in China to treat a variety of autoimmune and inflammatory diseases. The diterpenoids triptolide and Tripdiolide are two major active components in the T. wilfordii ethyl acetate extract. An efficient solid-phase extraction and high-performance liquid chromatography (SPE-HPLC) method to measure triptolide content in the extract has been previously reported. However, a suitable means of Tripdiolide quantification is not available because of interfering compounds in the extract that co-elute with Tripdiolide. Therefore, this paper describes a method wherein Tripdiolide content can be measured from a small amount of the extract.
METHODS AND RESULTS:
The extract solution (600 microL) was applied into an aminopropyl SPE tube. Triptolide was eluted with dichloromethane:methanol (1 mL, 49:1 v/v), followed by Tripdiolide elution with dichloromethane:methanol (3 mL, 17:3 v/v). The Tripdiolide eluate was analysed by HPLC using an isocratic solvent system and was quantified by measuring the peak area at 219 nm. The contents of triptolide and Tripdiolide in the extract were determined to be 807.32 +/- 51.94 and 366.13 +/- 17.21 microg/g of extract, respectively. Since Tripdiolide is biologically active and makes up a considerable portion of the extract, for extract quality control and standardisation purposes, it should be measured along with triptolide using the proposed SPE-HPLC method.

Phytochemistry. 2007 Apr;68(8):1172-8.

Anti-inflammatory and immunosuppressive compounds from Tripterygium wilfordii.[Pubmed: 17399748]

The extract of Tripterygium wilfordii Hook F. (TwHF), which showed anti-inflammatory and immunosuppressive activities in human clinical trials for rheumatoid arthritis, was subjected to the activity-guided fractionation and spectroscopic characterization of bioactives.
METHODS AND RESULTS:
A tetrahydrofuran lignan, tripterygiol (1), and eight known compounds, all capable of suppressing pro-inflammatory gene expression were identified. Most of the pharmacological activity of the extract can be attributed to triptolide, its most abundant and active component, with some contribution from Tripdiolide.

Can. J.Chem., 1981, 59(17):2677-83.

Cytotoxic diterpenes triptolide, tripdiolide, and cytotoxic triterpenes from tissue cultures of Tripterygium wilfordii[Reference: WebLink]


METHODS AND RESULTS:
Plant tissue cultures of Tripterygium wilfordii Hook F produced the cytotoxic diterpene triepoxides Tripdiolide (1) and triptolide (2) in yields that were 16 and 3 times greater, respectively, than those observed in the plant itself. Other diterpenes, dehydroabietic acid (3) and 15-hydroxy-18-norabieta-3,8,11,13-tetraene-3-oic acid methyl ester (4) were also isolated. Co-occuring in these cultures were the cytotoxic quinone-methides, celastrol (5), compound 6, and compound 7. Other triterpenes produced were oleanolic acid (8) and polpunonic acid (9). β-Sitosterol (17) was also isolated. The proposed structure of 4 was confirmed by synthesis starting from compound 3.
CONCLUSIONS:
Cytotoxic data are reported, and a possible biosynthetic relationship among dehydroabietic acid, compound 4, and Tripdiolide (1) is presented.

Tripdiolide Dilution Calculator

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Tripdiolide Molarity Calculator

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Preparing Stock Solutions of Tripdiolide

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.6567 mL 13.2837 mL 26.5675 mL 53.135 mL 66.4187 mL
5 mM 0.5313 mL 2.6567 mL 5.3135 mL 10.627 mL 13.2837 mL
10 mM 0.2657 mL 1.3284 mL 2.6567 mL 5.3135 mL 6.6419 mL
50 mM 0.0531 mL 0.2657 mL 0.5313 mL 1.0627 mL 1.3284 mL
100 mM 0.0266 mL 0.1328 mL 0.2657 mL 0.5313 mL 0.6642 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 Tripdiolide

Determination of tripdiolide in root extracts of Tripterygium wilfordii by solid-phase extraction and reversed-phase high-performance liquid chromatography.[Pubmed:18288676]

Phytochem Anal. 2008 Jul-Aug;19(4):348-52.

Extracts of Tripterygium wilfordii Hook F. have been widely used in China to treat a variety of autoimmune and inflammatory diseases. The diterpenoids triptolide and Tripdiolide are two major active components in the T. wilfordii ethyl acetate extract. An efficient solid-phase extraction and high-performance liquid chromatography (SPE-HPLC) method to measure triptolide content in the extract has been previously reported. However, a suitable means of Tripdiolide quantification is not available because of interfering compounds in the extract that co-elute with Tripdiolide. Therefore, this paper describes a method wherein Tripdiolide content can be measured from a small amount of the extract. The extract solution (600 microL) was applied into an aminopropyl SPE tube. Triptolide was eluted with dichloromethane:methanol (1 mL, 49:1 v/v), followed by Tripdiolide elution with dichloromethane:methanol (3 mL, 17:3 v/v). The Tripdiolide eluate was analysed by HPLC using an isocratic solvent system and was quantified by measuring the peak area at 219 nm. The contents of triptolide and Tripdiolide in the extract were determined to be 807.32 +/- 51.94 and 366.13 +/- 17.21 microg/g of extract, respectively. Since Tripdiolide is biologically active and makes up a considerable portion of the extract, for extract quality control and standardisation purposes, it should be measured along with triptolide using the proposed SPE-HPLC method.

Effective therapy for nephritis in (NZB x NZW)F1 mice with triptolide and tripdiolide, the principal active components of the Chinese herbal remedy Tripterygium wilfordii Hook F.[Pubmed:18512813]

Arthritis Rheum. 2008 Jun;58(6):1774-83.

OBJECTIVE: Triptolide and Tripdiolide are thought to be active components of the Chinese antirheumatic herbal remedy Tripterygium wilfordii Hook F, which has been shown to be effective in treating murine lupus nephritis. This study was undertaken to examine the therapeutic effect of triptolide and Tripdiolide on established lupus nephritis in (NZB x NZW)F1 mice. METHODS: (NZB x NZW)F1 mice were treated with vehicle, triptolide, or Tripdiolide for 15 weeks beginning at the age of 29 weeks (after the development of lupus nephritis). Body weight, proteinuria, and anti-double-stranded DNA (anti-dsDNA) antibodies were monitored, and the kidney and spleen were assessed histologically. Culture supernatants of spleen mononuclear cells were assayed for cytokines. RESULTS: By 28 weeks, most (NZB x NZW)F1 mice had developed lupus nephritis. Vehicle-treated mice exhibited progressive proteinuria, hypoalbuminemia, elevated blood urea nitrogen (BUN) levels, and evidence of severe nephritis. In contrast, proteinuria and BUN levels were significantly reduced in mice treated with either triptolide or Tripdiolide as compared with those treated with vehicle. There was no hypoalbuminemia or apparent evidence of lupus nephritis in mice treated with either of the 2 diterpenoids. At 44 weeks of age, the survival rate in mice treated with vehicle (35.7%) was markedly lower than that in mice treated with either triptolide (87.5%) or Tripdiolide (88.2%). The mean level of anti-dsDNA antibody in mice treated with Tripdiolide was lower than that in the vehicle-treated mice upon completion of the treatment course. Production of tumor necrosis factor, interleukin-6, and monocyte chemoattractant protein 1 by spleen cells was also decreased after diterpenoid therapy. CONCLUSION: Therapy with triptolide or Tripdiolide significantly ameliorated lupus nephritis in (NZB x NZW)F1 mice, reduced cytokine and chemokine production, and prolonged survival.

Anti-inflammatory and immunosuppressive compounds from Tripterygium wilfordii.[Pubmed:17399748]

Phytochemistry. 2007 Apr;68(8):1172-8.

The extract of Tripterygium wilfordii Hook F. (TwHF), which showed anti-inflammatory and immunosuppressive activities in human clinical trials for rheumatoid arthritis, was subjected to the activity-guided fractionation and spectroscopic characterization of bioactives. A tetrahydrofuran lignan, tripterygiol (1), and eight known compounds, all capable of suppressing pro-inflammatory gene expression were identified. Most of the pharmacological activity of the extract can be attributed to triptolide, its most abundant and active component, with some contribution from Tripdiolide.

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