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Toddalolactone

CAS# 483-90-9

Toddalolactone

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Quality Control of Toddalolactone

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Chemical structure

Toddalolactone

3D structure

Chemical Properties of Toddalolactone

Cas No. 483-90-9 SDF Download SDF
PubChem ID 160485 Appearance White powder
Formula C16H20O6 M.Wt 308.33
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility Soluble in DMSO and methan
Chemical Name 6-[(2R)-2,3-dihydroxy-3-methylbutyl]-5,7-dimethoxychromen-2-one
SMILES CC(C)(C(CC1=C(C=C2C(=C1OC)C=CC(=O)O2)OC)O)O
Standard InChIKey GLWPLQBQHWYKRK-CYBMUJFWSA-N
Standard InChI InChI=1S/C16H20O6/c1-16(2,19)13(17)7-10-11(20-3)8-12-9(15(10)21-4)5-6-14(18)22-12/h5-6,8,13,17,19H,7H2,1-4H3/t13-/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 Toddalolactone

1 Zanthoxylum sp.

Biological Activity of Toddalolactone

DescriptionToddalolactone, a natural coumarin, inhibits the activity of recombinant human Plasminogen activator inhibitor-1 (PAI-1) in a dose-dependent manner, yielding an IC50 value of 37.31 ± 3.23 μM.
TargetsPAI-1
In vitro

Spasmolytic activity of Toddalia asiatica Var. floribunda.[Pubmed: 12164278 ]

Phytother Res. 2002 May;16(3):281-2.

The spasmolytic activity of the aerial parts of Toddalia asiatica var. floribunda (family Rutaceae) was evaluated.
METHODS AND RESULTS:
The ethanol extract exhibited significant spasmolytic activity and was then partitioned into five fractions. The activity was found to be concentrated only in the hexane and chloroform fractions.
CONCLUSIONS:
This activity was shown not to be due to the coumarins, Toddalolactone and toddanone, as was previously thought.

Inhibition of PAI-1 Activity by Toddalolactone as a Mechanism for Promoting Blood Circulation and Removing Stasis by Chinese Herb Zanthoxylum nitidum var. tomentosum.[Pubmed: 28785222 ]

Front Pharmacol. 2017 Jul 21;8:489.

Traditional Chinese medicine has been used to treat a variety of human diseases for many centuries. Zanthoxylum nitidum var. tomentosum is used as an adjuvant to promote blood circulation and remove stasis. However, the mechanisms of improving circulation and other biological activities of Z. nitidum var. tomentosum are still unclear. Plasminogen activator inhibitor-1 (PAI-1) regulates the plasminogen activation system through inhibition of tissue-type and urokinase-type plasminogen activators (tPA and uPA). PAI-1 has been linked to fibrin deposition that evolves into organ fibrosis and atherosclerosis.
METHODS AND RESULTS:
In the present study, we showed that ethanol extract prepared from Z. nitidum var. tomentosum exhibited PAI-1 inhibitory activity, and identified Toddalolactone as the main active component that inhibited the activity of recombinant human PAI-1 with IC50 value of 37.31 ± 3.23 μM, as determined by chromogenic assay, and the effect was further confirmed by clot lysis assay. In vitro study showed that Toddalolactone inhibited the binding between PAI-1 and uPA, and therefore prevented the formation of the PAI-1/uPA complex. Intraperitoneal injection of Toddalolactone in mice significantly prolonged tail bleeding and reduced arterial thrombus weight in a FeCl3-induced thrombosis model. In addition, the hydroxyproline level in the plasma and the degree of liver fibrosis in mice were decreased after intraperitoneal injection of Toddalolactone in CCl4-induced mouse liver fibrosis model.
CONCLUSIONS:
Taken together, PAI-1 inhibition exerted by Toddalolactone may represent a novel molecular mechanism by which Z. nitidum var. tomentosum manifests its effect in the treatment of thrombosis and fibrosis.

Protocol of Toddalolactone

Structure Identification
Yakugaku Zasshi. 1991 Jul;111(7):376-85.

Studies on the chemical constituents of rutaceous plants. LXVII. The chemical constituents of Toddalia asiatica (L.) Lam. (T. aculeata Pers). Examination of coumarins using supercritical fluid and soxhlet extraction. Is toddalolactone a genuine natural co[Pubmed: 1783986]

It is well known that Toddalolactone (1) is a main component of Toddalia asiatica (L.) Lam. (T. aculeata Pers.) (Rutaceae). However, supercritical fluid (SCF) extraction of the plant by using CO2 showed that a main component of the extract was not Toddalolactone, but aculeatin (2), a coumarin having an epoxy ring on the side chain. These facts strongly suggested that Toddalolactone, corresponding to the hydrate of 2, was an artefact derived from 2 during extraction.
METHODS AND RESULTS:
SCF extraction under various conditions was examined in detail by quantitative analyses of Toddalolactone and 2 by high performance liquid chromatography and the optimum condition extracting the both components was found to be at 40 degrees C and at 300 kg/cm2. The condition was applied to the plant treated with aqueous sodium hydrogen carbonate in order to remove any acidic substances and Toddalolactone was still detected in the extract.
CONCLUSIONS:
Thus, it is conclude that Toddalolactone should be a genuine natural coumarin but that previous isolation of Toddalolactone as a main component resulted in an isolation of an artefact derived from 2. SCF extraction was suggested to be a useful extraction method.

Toddalolactone Dilution Calculator

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Toddalolactone Molarity Calculator

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Preparing Stock Solutions of Toddalolactone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2433 mL 16.2164 mL 32.4328 mL 64.8656 mL 81.082 mL
5 mM 0.6487 mL 3.2433 mL 6.4866 mL 12.9731 mL 16.2164 mL
10 mM 0.3243 mL 1.6216 mL 3.2433 mL 6.4866 mL 8.1082 mL
50 mM 0.0649 mL 0.3243 mL 0.6487 mL 1.2973 mL 1.6216 mL
100 mM 0.0324 mL 0.1622 mL 0.3243 mL 0.6487 mL 0.8108 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 Toddalolactone

Spasmolytic activity of Toddalia asiatica Var. floribunda.[Pubmed:12164278]

Phytother Res. 2002 May;16(3):281-2.

The spasmolytic activity of the aerial parts of Toddalia asiatica var. floribunda (family Rutaceae) was evaluated. The ethanol extract exhibited significant spasmolytic activity and was then partitioned into five fractions. The activity was found to be concentrated only in the hexane and chloroform fractions. This activity was shown not to be due to the coumarins, Toddalolactone and toddanone, as was previously thought.

[Studies on the chemical constituents of rutaceous plants. LXVII. The chemical constituents of Toddalia asiatica (L.) Lam. (T. aculeata Pers). Examination of coumarins using supercritical fluid and soxhlet extraction. Is toddalolactone a genuine natural coumarin?].[Pubmed:1783986]

Yakugaku Zasshi. 1991 Jul;111(7):376-85.

It is well known that Toddalolactone (1) is a main component of Toddalia asiatica (L.) Lam. (T. aculeata Pers.) (Rutaceae). However, supercritical fluid (SCF) extraction of the plant by using CO2 showed that a main component of the extract was not 1, but aculeatin (2), a coumarin having an epoxy ring on the side chain. The same result was obtained from Soxhlet extraction by using aprotic solvents. On the other hand, Soxhlet extraction by using methanol yielded 13, corresponding to a methanol adduct of 2, as an additional component, which was able to be also produced in 50.2% yield only by heating pure 2 in methanol, indicating that the epoxy ring in 2 can be easily attacked by a weak nucleophile like methanol. These facts strongly suggested that 1, corresponding to the hydrate of 2, was an artefact derived from 2 during extraction. SCF extraction under various conditions was examined in detail by quantitative analyses of 1 and 2 by high performance liquid chromatography and the optimum condition extracting the both components was found to be at 40 degrees C and at 300 kg/cm2. The condition was applied to the plant treated with aqueous sodium hydrogen carbonate in order to remove any acidic substances and 1 was still detected in the extract. Thus, it is conclude that 1 should be a genuine natural coumarin but that previous isolation of 1 as a main component resulted in an isolation of an artefact derived from 2. SCF extraction was suggested to be a useful extraction method.

Description

Toddalolactone, a main component of Toddalia asiatica, inhibits the activity of recombinant human plasminogen activator inhibitor-1 (PAI-1), with an IC50 value of 37.31 μM.

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