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Deacetylpseudolaric acid A

CAS# 82508-37-0

Deacetylpseudolaric acid A

2D Structure

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Quality Control of Deacetylpseudolaric acid A

3D structure

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Deacetylpseudolaric acid A

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Chemical Properties of Deacetylpseudolaric acid A

Cas No. 82508-37-0 SDF Download SDF
PubChem ID 11977243 Appearance Powder
Formula C20H26O5 M.Wt 346.4
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2E,4E)-5-[(1R,7S,8R,9R)-7-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
SMILES CC1=CCC23CCC(C2(CC1)O)C(OC3=O)(C)C=CC=C(C)C(=O)O
Standard InChIKey MQOMHFMKUJFDBH-SWRVIOJRSA-N
Standard InChI InChI=1S/C20H26O5/c1-13-6-10-19-11-8-15(20(19,24)12-7-13)18(3,25-17(19)23)9-4-5-14(2)16(21)22/h4-6,9,15,24H,7-8,10-12H2,1-3H3,(H,21,22)/b9-4+,14-5+/t15-,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 Deacetylpseudolaric acid A

The root bark of Pseudolarix amabilis

Biological Activity of Deacetylpseudolaric acid A

DescriptionDeacetylpseudolaric acid A is a natural product from Pseudolarix amabilis.
In vivo

Metabolic pathway and metabolites of total diterpene acid isolated from Pseudolarix kaempferi.[Pubmed: 25322560 ]

Yao Xue Xue Bao. 2014 Aug;49(8):1169-74.

The preliminary metabolic profile of total diterpene acid (TDA) isolated from Pseudolarix kaempferi was investigated by using in vivo and in vitro tests.
METHODS AND RESULTS:
Pseudolaric acid C2 (PC2) was identified as the predominant metabolite in plasma, urine, bile and feces after both oral and intravenous administrations to rats using HPLC-UV and HPLC-ESI/MS(n), and demethoxydeacetoxypseudolaric acid B (DDPB), a metabolite proposed to be the glucoside of PC2 (PC2G), as well as pseudolaric acid C (PC), pseudolaric acid A (PA), pseudolaric acid A O-beta-D glucopyranoside (PAG), pseudolaric acid B O-beta-D glucopyranoside (PBG) and Deacetylpseudolaric acid A (DPA) originated from TDA could also be detected. It was demonstrated by tests that the metabolism of TDA is independent of intestinal microflora, and neither of pepsin and trypsin is in charge of metabolism of TDA, TDA is also stable in both pH environments of gastric tract and intestinal tract. The metabolites of TDA in whole blood in vitro incubation were found to be PC2, DDPB and PC2G, which demonstrated that the metabolic reaction of TDA in vivo is mainly occurred in blood and contributed to be the hydrolysis of plasma esterase to ester bond, as well as the glucosylation reaction.
CONCLUSIONS:
These results clarified the metabolic pathway of TDA for the first time, which is of great significance to the in vivo active form and acting mechanism research of P. kaempferi.

Protocol of Deacetylpseudolaric acid A

Structure Identification
J Chromatogr A. 2012 Apr 27;1235:34-8.

Application of step-wise gradient high-performance counter-current chromatography for rapid preparative separation and purification of diterpene components from Pseudolarix kaempferi Gordon.[Pubmed: 22424731]

In general, simultaneously separation and purification of components with a broad polarity range from traditional Chinese medicine (TCM) is a challenge by an ordinary high-speed counter-current chromatography (HSCCC) method.
METHODS AND RESULTS:
In this paper, we describes a rapid and efficient separation method of combining three-step gradient elution and two-step flow-rate gradient elution using high-performance counter-current chromatography (HPCCC) to separate 8 diterpene compounds simultaneously within 80 min in a single run from the alcohol extract of Pseudolarix kaempferi Gordon. This separation process produced 166 mg pseudolaric acid B O-β-d-glucopyranoside (PABGly), 152 mg pseudolaric acid C (PAC), 8 mg Deacetylpseudolaric acid A (deacetylPAA), 5 mg pseudolaric acid A O-β-d-glucopyranoside (PAAGly), 484 mg pseudolaric acid B (PAB), 33 mg pseudolaric acid B methyl ester (PAB methyl ester), 10mg pseudolaric acid A (PAA) and 18 mg pseudolaric acid H (PAH) from 1.0 g crude sample with purities of 98.6%, 99.6%, 92.3%, 92.2%, 99.2%, 99.4%, 98.3%, 91.0%, respectively.
CONCLUSIONS:
Our study indicates that the suitable combination of step-wise gradient elution and flow-rate gradient elution using HPCCC is an effective strategy to separate complex components from natural products.

Deacetylpseudolaric acid A Dilution Calculator

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Preparing Stock Solutions of Deacetylpseudolaric acid A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8868 mL 14.4342 mL 28.8684 mL 57.7367 mL 72.1709 mL
5 mM 0.5774 mL 2.8868 mL 5.7737 mL 11.5473 mL 14.4342 mL
10 mM 0.2887 mL 1.4434 mL 2.8868 mL 5.7737 mL 7.2171 mL
50 mM 0.0577 mL 0.2887 mL 0.5774 mL 1.1547 mL 1.4434 mL
100 mM 0.0289 mL 0.1443 mL 0.2887 mL 0.5774 mL 0.7217 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 Deacetylpseudolaric acid A

Application of step-wise gradient high-performance counter-current chromatography for rapid preparative separation and purification of diterpene components from Pseudolarix kaempferi Gordon.[Pubmed:22424731]

J Chromatogr A. 2012 Apr 27;1235:34-8.

In general, simultaneously separation and purification of components with a broad polarity range from traditional Chinese medicine (TCM) is a challenge by an ordinary high-speed counter-current chromatography (HSCCC) method. In this paper, we describes a rapid and efficient separation method of combining three-step gradient elution and two-step flow-rate gradient elution using high-performance counter-current chromatography (HPCCC) to separate 8 diterpene compounds simultaneously within 80 min in a single run from the alcohol extract of Pseudolarix kaempferi Gordon. This separation process produced 166 mg pseudolaric acid B O-beta-d-glucopyranoside (PABGly), 152 mg pseudolaric acid C (PAC), 8 mg Deacetylpseudolaric acid A (deacetylPAA), 5 mg pseudolaric acid A O-beta-d-glucopyranoside (PAAGly), 484 mg pseudolaric acid B (PAB), 33 mg pseudolaric acid B methyl ester (PAB methyl ester), 10mg pseudolaric acid A (PAA) and 18 mg pseudolaric acid H (PAH) from 1.0 g crude sample with purities of 98.6%, 99.6%, 92.3%, 92.2%, 99.2%, 99.4%, 98.3%, 91.0%, respectively. Our study indicates that the suitable combination of step-wise gradient elution and flow-rate gradient elution using HPCCC is an effective strategy to separate complex components from natural products.

[Metabolic pathway and metabolites of total diterpene acid isolated from Pseudolarix kaempferi].[Pubmed:25322560]

Yao Xue Xue Bao. 2014 Aug;49(8):1169-74.

The preliminary metabolic profile of total diterpene acid (TDA) isolated from Pseudolarix kaempferi was investigated by using in vivo and in vitro tests. Pseudolaric acid C2 (PC2) was identified as the predominant metabolite in plasma, urine, bile and feces after both oral and intravenous administrations to rats using HPLC-UV and HPLC-ESI/MS(n), and demethoxydeacetoxypseudolaric acid B (DDPB), a metabolite proposed to be the glucoside of PC2 (PC2G), as well as pseudolaric acid C (PC), pseudolaric acid A (PA), pseudolaric acid A O-beta-D glucopyranoside (PAG), pseudolaric acid B O-beta-D glucopyranoside (PBG) and Deacetylpseudolaric acid A (DPA) originated from TDA could also be detected. It was demonstrated by tests that the metabolism of TDA is independent of intestinal microflora, and neither of pepsin and trypsin is in charge of metabolism of TDA, TDA is also stable in both pH environments of gastric tract and intestinal tract. The metabolites of TDA in whole blood in vitro incubation were found to be PC2, DDPB and PC2G, which demonstrated that the metabolic reaction of TDA in vivo is mainly occurred in blood and contributed to be the hydrolysis of plasma esterase to ester bond, as well as the glucosylation reaction. These results clarified the metabolic pathway of TDA for the first time, which is of great significance to the in vivo active form and acting mechanism research of P. kaempferi.

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