Arteannuin B

CAS# 50906-56-4

Arteannuin B

Catalog No. BCN5623----Order now to get a substantial discount!

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Quality Control of Arteannuin B

Number of papers citing our products

Chemical structure

Arteannuin B

3D structure

Chemical Properties of Arteannuin B

Cas No. 50906-56-4 SDF Download SDF
PubChem ID 162096 Appearance Powder
Formula C15H20O3 M.Wt 248.3
Type of Compound Sesquiterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC1CCC2C(=C)C(=O)OC23C1CCC4(C3O4)C
Standard InChIKey QWQSMEDUZQDVLA-USPGQWGOSA-N
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 Arteannuin B

The herbs of Artemisia annua

Biological Activity of Arteannuin B

DescriptionArteannuin B and artemisinic acid are biogenetic precursors of artemisinin, an important antimalarial produced by the herb Artemisia annua, they are active against different bacteria and certain fungal species. Arteannuin B has potential antimalarialand antitumor activity.
TargetsAntifection
In vitro

Derivatives of arteannuin B with antileukemia activity[Pubmed: 1442049]

Yao Xue Xue Bao. 1992;27(4):317-20.


METHODS AND RESULTS:
Arteannuin B (I) was converted to hydroxy lactones (VII, VIII) by a mixture of formic acid and sulfuric acid. Compound VI and Compound VII both showed activity against leukemia P 388 cell in vitro. The rate of growth inhibition were 97.5% and 11.8% for (VI) and 80% and 52.6% for (VII) at the concentration of 10 and 1 micrograms/ml respectively.
CONCLUSIONS:
It seems that the antileukemia activity of 6-membered lactone is higher than that of 5-membered and the methylene group is necessary for the antileukemia activity.

Antimicrobial activity of artemisinin and its precursors.[Reference: WebLink]

Current Science, 2000 , 78 (6) :709-713.

Artemisinic acid and Arteannuin B are biogenetic precursors of artemisinin, an important antimalarial produced by the herb Artemisia annua. These compounds have been screened for antimicrobial activity against a range of organisms.
CONCLUSIONS:
All the three compounds are active against different bacteria and certain fungal species.

Protocol of Arteannuin B

Structure Identification
J Sep Sci. 2005 Nov;28(17):2288-92.

Simultaneous densitometric determination of artemisinin, artemisinic acid and arteannuin-B in Artemisia annua using reversed-phase thin layer chromatography.[Pubmed: 16342793]


METHODS AND RESULTS:
A rapid and simple RP-TLC method for simultaneous quantification of pharmacologically important sesquiterpene artemisinin (AM) together with its precursors Arteannuin B (AB) and artemisinic acid (AA) in the inflorescence part of Artemisia annua plant has been developed. The RP-TLC of sesquiterpenes was performed on RP-18 F254 S thin-layer chromatographic plates by developing in mobile phase, containing 0.2% TFA in water/ACN (35:65, v/v). The densitometric determination of AM, AB and AA was carried out after derivatization with anisaldehyde reagent at 426 nm in absorption-reflectance mode.

J Nat Prod. 1993 Sep;56(9):1559-66.

Bioconversion of arteannuin B to artemisinin.[Pubmed: 8254350]

Arteannuin B, which co-occurs with artemisinin, the potent antimalarial principle of the Chinese medicinal herb Artemisia annua (Asteraceae), has been converted to the latter using crude and semi-purified cell-free extracts of the leaf homogenates of the plant. Detection procedures to quantitate this bioconversion, including one that is novel which uses gcms, are detailed.

8. IUPAC symposium on organometallic chemistry directed towards organic synthesis, Santa Barbara, CA (United States), 6-10 Aug 1995.

Samarium(II) induced asymmetric reductive cyclizations: The total synthesis of (-)-C{sub 10} desmethyl arteannuin B[Reference: WebLink]

Arteannuin B is a member of the qinghaosu family, a novel class of sesquiterpenes that exhibit powerful antimalarial activity even against chloroquinine resistant strains. It is readily convertible to qinghaosu in several high yielding steps and has potential antitumor activity. Several approaches to the construction of the cis-decalin backbone have involved the use of electrochemical and metal promoted reductions as well as alkylations.
METHODS AND RESULTS:
We report a short convenient total synthesis of (-)-C{sub 10} desmethyl Arteannuin B utilizing an asymmetric reductive cyclization with samarium (II) iodide which selectively forms the cis-decalin ring structure while setting the trans relationship between the subunits of the {gamma}-hydroxy ester.

Arteannuin B Dilution Calculator

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Arteannuin B Molarity Calculator

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Preparing Stock Solutions of Arteannuin B

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.0274 mL 20.1369 mL 40.2739 mL 80.5477 mL 100.6847 mL
5 mM 0.8055 mL 4.0274 mL 8.0548 mL 16.1095 mL 20.1369 mL
10 mM 0.4027 mL 2.0137 mL 4.0274 mL 8.0548 mL 10.0685 mL
50 mM 0.0805 mL 0.4027 mL 0.8055 mL 1.611 mL 2.0137 mL
100 mM 0.0403 mL 0.2014 mL 0.4027 mL 0.8055 mL 1.0068 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 Arteannuin B

Simultaneous densitometric determination of artemisinin, artemisinic acid and arteannuin-B in Artemisia annua using reversed-phase thin layer chromatography.[Pubmed:16342793]

J Sep Sci. 2005 Nov;28(17):2288-92.

A rapid and simple RP-TLC method for simultaneous quantification of pharmacologically important sesquiterpene artemisinin (AM) together with its precursors arteannuin-B (AB) and artemisinic acid (AA) in the inflorescence part of Artemisia annua plant has been developed. The RP-TLC of sesquiterpenes was performed on RP-18 F254 S thin-layer chromatographic plates by developing in mobile phase, containing 0.2% TFA in water/ACN (35:65, v/v). The densitometric determination of AM, AB and AA was carried out after derivatization with anisaldehyde reagent at 426 nm in absorption-reflectance mode.

[Derivatives of arteannuin B with antileukemia activity].[Pubmed:1442049]

Yao Xue Xue Bao. 1992;27(4):317-20.

Arteannuin B (I) was converted to hydroxy lactones (VII, VIII) by a mixture of formic acid and sulfuric acid. Compound VI and Compound VII both showed activity against leukemia P 388 cell in vitro. The rate of growth inhibition were 97.5% and 11.8% for (VI) and 80% and 52.6% for (VII) at the concentration of 10 and 1 micrograms/ml respectively. It seems that the antileukemia activity of 6-membered lactone is higher than that of 5-membered and the methylene group is necessary for the antileukemia activity.

Bioconversion of arteannuin B to artemisinin.[Pubmed:8254350]

J Nat Prod. 1993 Sep;56(9):1559-66.

Arteannuin B, which co-occurs with artemisinin, the potent antimalarial principle of the Chinese medicinal herb Artemisia annua (Asteraceae), has been converted to the latter using crude and semi-purified cell-free extracts of the leaf homogenates of the plant. Detection procedures to quantitate this bioconversion, including one that is novel which uses gcms, are detailed.

Description

Arteannuin B co-occurs with artemisinin, which is the potent antimalarial principle of the Chinese medicinal herb Artemisia annua (Asteraceae).

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