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Diacetylpiptocarphol

CAS# 103476-99-9

Diacetylpiptocarphol

Catalog No. BCN4737----Order now to get a substantial discount!

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Quality Control of Diacetylpiptocarphol

Number of papers citing our products

Chemical structure

Diacetylpiptocarphol

3D structure

Chemical Properties of Diacetylpiptocarphol

Cas No. 103476-99-9 SDF Download SDF
PubChem ID 102004563 Appearance Powder
Formula C19H24O9 M.Wt 396.39
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Synonyms 101628-29-9
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name [(1S,2E,8R,10R,11R)-8-acetyloxy-10,11-dihydroxy-1,10-dimethyl-5-oxo-4,14-dioxatricyclo[9.2.1.03,7]tetradeca-2,6-dien-6-yl]methyl acetate
SMILES CC(=O)OCC1=C2C(CC(C3(CCC(O3)(C=C2OC1=O)C)O)(C)O)OC(=O)C
Standard InChIKey GSADBENAXUTZTK-RRRPBPPSSA-N
Standard InChI InChI=1S/C19H24O9/c1-10(20)25-9-12-15-13(27-16(12)22)7-17(3)5-6-19(24,28-17)18(4,23)8-14(15)26-11(2)21/h7,14,23-24H,5-6,8-9H2,1-4H3/b13-7+/t14-,17+,18-,19-/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 Diacetylpiptocarphol

The herbs of Vernonia volkameriifolia

Biological Activity of Diacetylpiptocarphol

Description1. Diacetylpiptocarphol shows antileishmanial activity against three stages of Leishmania infantum.
TargetsAntifection

Diacetylpiptocarphol Dilution Calculator

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Diacetylpiptocarphol Molarity Calculator

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Preparing Stock Solutions of Diacetylpiptocarphol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.5228 mL 12.6138 mL 25.2277 mL 50.4554 mL 63.0692 mL
5 mM 0.5046 mL 2.5228 mL 5.0455 mL 10.0911 mL 12.6138 mL
10 mM 0.2523 mL 1.2614 mL 2.5228 mL 5.0455 mL 6.3069 mL
50 mM 0.0505 mL 0.2523 mL 0.5046 mL 1.0091 mL 1.2614 mL
100 mM 0.0252 mL 0.1261 mL 0.2523 mL 0.5046 mL 0.6307 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 Diacetylpiptocarphol

Evaluation of antiplasmodial and antileishmanial activities of herbal medicine Pseudelephantopus spiralis (Less.) Cronquist and isolated hirsutinolide-type sesquiterpenoids.[Pubmed:25980423]

J Ethnopharmacol. 2015 Jul 21;170:167-74.

ETHNOPHARMACOLOGICAL RELEVANCE: Pseudelephantopus spiralis (Less.) Cronquist is distributed in the Caribbean, Mesoamerica and Latin America. Preparations of the plant are traditionally used in Latin America for the treatment of various diseases including fever, malaria, and spleen or liver inflammations. MATERIALS AND METHODS: Aerial parts of P. spiralis were extracted with either ethanol or distilled water. Seven hirsutinolide-type sesquiterpenoids were isolated: 8-acetyl-13-ethoxypiptocarphol (1), Diacetylpiptocarphol (2), piptocarphins A (3), F (4) and D (5), (1S(*),4R(*),8S(*),10R(*))-1,4-epoxy-13-ethoxy-1,8,10-trihydroxygermacra-5E,7(11) -dien-6,12-olide (6), and piptocarphol (7). Extracts and isolated compounds (2, 3, 5-7) were screened for their in vitro antiplasmodial activity against the chloroquine-resistant Plasmodium falciparum strain FcM29-Cameroon and antileishmanial activity against three stages of Leishmania infantum. Their cytotoxicities were also evaluated against healthy VERO cell lines and J774A.1 macrophages, the host cells of the Leishmania parasites in humans. RESULTS: Aqueous extracts showed a greater inhibitory effect than alcoholic extracts, with IC50 on P. falciparum of 3.0microg/mL versus 21.1microg/mL, and on L. infantum of 13.4microg/mL versus >50microg/mL. Both extracts were found to be cytotoxic to VERO cells (CC50<3microg/mL). Sesquiterpene lactones 2 and 3 showed the best activity against both parasites but failed in selectivity. Carbon 8 hydroxylated hirsutinolides 5-7 presented the particularity of exhibiting two conformers observed in solution during extensive NMR analyses in CD3OD and UHPLC-MS. The presence of a hydroxyl function at C-8 decreased the activity of 5-7 on the two parasites and also on VERO cells. CONCLUSION: The antiplasmodial activity displayed by the aqueous extract explains the traditional use of P. spiralis in the treatment of malaria. This activity seems to be attributable to the presence of sesquiterpene lactones 2 and 3, the most active against P. falciparum. Aqueous extract and compounds 2, 3 and 6 were also active against L. infantum but lacked in selectivity due to their cytotoxicity towards macrophages. Exploring the safety and antiplasmodial efficacy of this traditional remedy will require further toxicological and in vivo studies in the light of the cytotoxicity towards healthy cell lines displayed by the aqueous extract and compounds 2 and 3.

Sesquiterpene lactones from Vernonia scorpioides and their in vitro cytotoxicity.[Pubmed:20599237]

Phytochemistry. 2010 Sep;71(13):1539-44.

Fresh leaves of Vernonia scorpioides are widely used in Brazil to treat a variety of skin disorders. Previous in vivo studies with extracts of this species had also demonstrated a high antitumor potential. This paper reports isolation of four sesquiterpene lactones (hirsutinolides and glaucolides), together with Diacetylpiptocarphol, 8-acetyl-13-etoxypiptocarphol, luteolin, apigenin, and ethyl caffeate from fresh leaves and flowers of Vernonia scorpioides. The hypothesis that hirsutinolide 3 is formed during extraction was verified theoretically using Density Functional Theory. The effects of isolated compounds on in vitro tumor cells were investigated, as well as their genotoxicity by means of an in vitro comet assay. The results indicate that glaucolide 2 and hirsutinolide 4 are toxic to HeLa cells. These compounds were genotoxic in vitro, a property that appears to be related to the presence of their epoxy groups, which has been a more reliable indication of toxicity than substitution on C-13 or the presence of alpha,beta-unsaturated keto-groups. These results need to be replicated in vivo in order to ascertain their toxicity.

Description

Diacetylpiptocarphol has antiplasmodial activity

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