Khasianine

CAS# 32449-98-2

Khasianine

Catalog No. BCN2530----Order now to get a substantial discount!

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Quality Control of Khasianine

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Chemical structure

Khasianine

3D structure

Chemical Properties of Khasianine

Cas No. 32449-98-2 SDF Download SDF
PubChem ID 73606 Appearance White powder
Formula C39H63NO11 M.Wt 721.93
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms β2-Solamargine
Solubility Soluble in ethanol, ethyl acetate and methanol; insoluble in water
SMILES CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)C)O)O)O)O)O)C)C)C)NC1
Standard InChIKey KRQDMAXNTWLTDZ-FXQMNGNYSA-N
Standard InChI InChI=1S/C39H63NO11/c1-18-8-13-39(40-16-18)19(2)28-26(51-39)15-25-23-7-6-21-14-22(9-11-37(21,4)24(23)10-12-38(25,28)5)48-36-33(46)31(44)34(27(17-41)49-36)50-35-32(45)30(43)29(42)20(3)47-35/h6,18-20,22-36,40-46H,7-17H2,1-5H3/t18-,19+,20-,22+,23-,24+,25+,26+,27+,28+,29-,30+,31+,32-,33-,34+,35+,36-,37+,38+,39?/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 Khasianine

The herbs of Solanum nigrum L.

Biological Activity of Khasianine

DescriptionKhasianine exhibits strong activity against liver damage induced by CCl4.
In vitro

The rhamnose moiety of solamargine plays a crucial role in triggering cell death by apoptosis.[Pubmed: 9439603]

Biochem Biophys Res Commun. 1998 Jan 6;242(1):21-5.

Solamargine, solasodine and Khasianine steroidal alkaloids are utilized to determine the role of carbohydrate moiety in the mechanism of apoptosis.
METHODS AND RESULTS:
The C3 side chain of solamargine, Khasianine and solasodine contains 4'Rha-Glc-Rha2', 4'Rha-Glc and H, respectively. Solamargine possessed potent cytotoxicity to human hepatoma cells, while the cytotoxicity of Khasianine was greatly diminished. Nevertheless, only solamargine could induced "sub-G1" of apoptotic feature in flowcytometry. Thus, the 2'Rha moiety of solamargine may play a crucial role in triggering cell death by apoptosis. In addition, the molecular modeling of solamargine indicated that the 2'Rha moiety was adjacent to the rigid steroid structure, and drastically changed the dihedral angle of the glycosidic bond.
CONCLUSIONS:
The regulations of TNFR I and II expression by different carbohydrate moieties were also distinct. It implied that the carbohydrate moieties of steroidal alkaloids might alter the binding specificity to steroid receptors and consequently regulate the gene expression in different manners.

Cytotoxic principles and their derivatives of Formosan Solanum plants.[Pubmed: 8450317]

J Nat Prod. 1993 Jan;56(1):15-21.


METHODS AND RESULTS:
The new steroidal alkaloid capsimine-3-O-beta-D-glucoside [1] was isolated from the root bark of Solanum capsicastrum, and carpesterol [2], 3 beta-(p-hydroxy)-benzoyloxy-22 alpha-hydroxy-4 alpha-methyl-5 alpha-stigmast-7-en-6-one [3], and a new steroidal glycoside named indioside A [4] were isolated from the fruit of Solanum indicum. Indioside A was characterized as 3 beta-O-[alpha-L-rhamnopyranosyl-(1-->2), beta-D-glucopyranosyl-(1-->4), beta-D-glucopyranosyl-(1-->3)-]alpha-L-rhamnopyranosyl-(-->2)]-beta-D- glucopyranosyl]-diosgenin. Khasianine, dihydrosolasodine, capsimine, and capsimine-3-O-beta-D-glucoside exhibited strong activity against liver damage induced by CCl4.
CONCLUSIONS:
Capsimine and narigenin exhibited significant cytotoxic effect against human PLC/PRF/5 and KB cells in vitro, and capsicastrine and etioline exhibited significant cytotoxicity against human PLC/PRF/5 cells in vitro.

Khasianine Dilution Calculator

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Khasianine Molarity Calculator

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Preparing Stock Solutions of Khasianine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.3852 mL 6.9259 mL 13.8518 mL 27.7035 mL 34.6294 mL
5 mM 0.277 mL 1.3852 mL 2.7704 mL 5.5407 mL 6.9259 mL
10 mM 0.1385 mL 0.6926 mL 1.3852 mL 2.7704 mL 3.4629 mL
50 mM 0.0277 mL 0.1385 mL 0.277 mL 0.5541 mL 0.6926 mL
100 mM 0.0139 mL 0.0693 mL 0.1385 mL 0.277 mL 0.3463 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 Khasianine

The rhamnose moiety of solamargine plays a crucial role in triggering cell death by apoptosis.[Pubmed:9439603]

Biochem Biophys Res Commun. 1998 Jan 6;242(1):21-5.

Solamargine, solasodine and Khasianine steroidal alkaloids are utilized to determine the role of carbohydrate moiety in the mechanism of apoptosis. The C3 side chain of solamargine, Khasianine and solasodine contains 4'Rha-Glc-Rha2', 4'Rha-Glc and H, respectively. Solamargine possessed potent cytotoxicity to human hepatoma cells, while the cytotoxicity of Khasianine was greatly diminished. Nevertheless, only solamargine could induced "sub-G1" of apoptotic feature in flowcytometry. Thus, the 2'Rha moiety of solamargine may play a crucial role in triggering cell death by apoptosis. In addition, the molecular modeling of solamargine indicated that the 2'Rha moiety was adjacent to the rigid steroid structure, and drastically changed the dihedral angle of the glycosidic bond. The regulations of TNFR I and II expression by different carbohydrate moieties were also distinct. It implied that the carbohydrate moieties of steroidal alkaloids might alter the binding specificity to steroid receptors and consequently regulate the gene expression in different manners.

Cytotoxic principles and their derivatives of Formosan Solanum plants.[Pubmed:8450317]

J Nat Prod. 1993 Jan;56(1):15-21.

The new steroidal alkaloid capsimine-3-O-beta-D-glucoside [1] was isolated from the root bark of Solanum capsicastrum, and carpesterol [2], 3 beta-(p-hydroxy)-benzoyloxy-22 alpha-hydroxy-4 alpha-methyl-5 alpha-stigmast-7-en-6-one [3], and a new steroidal glycoside named indioside A [4] were isolated from the fruit of Solanum indicum. Indioside A was characterized as 3 beta-O-[alpha-L-rhamnopyranosyl-(1-->2), beta-D-glucopyranosyl-(1-->4), beta-D-glucopyranosyl-(1-->3)-]alpha-L-rhamnopyranosyl-(-->2)]-beta-D- glucopyranosyl]-diosgenin. Khasianine, dihydrosolasodine, capsimine, and capsimine-3-O-beta-D-glucoside exhibited strong activity against liver damage induced by CCl4. Capsimine and narigenin exhibited significant cytotoxic effect against human PLC/PRF/5 and KB cells in vitro, and capsicastrine and etioline exhibited significant cytotoxicity against human PLC/PRF/5 cells in vitro.

Description

Khasianine is a steroidal glycoalkaloid which is obtained from black nightshade (Solanum Nigrum L.), which displays antitumor activity.

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