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Isochamaejasmine

CAS# 93859-63-3

Isochamaejasmine

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Chemical structure

Isochamaejasmine

3D structure

Chemical Properties of Isochamaejasmine

Cas No. 93859-63-3 SDF Download SDF
PubChem ID 390361 Appearance Powder
Formula C30H22O10 M.Wt 542.5
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S,3R)-3-[(2R,3S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
SMILES C1=CC(=CC=C1C2C(C(=O)C3=C(C=C(C=C3O2)O)O)C4C(OC5=CC(=CC(=C5C4=O)O)O)C6=CC=C(C=C6)O)O
Standard InChIKey RNQBLQALVMHBKH-SQYWJIFTSA-N
Standard InChI InChI=1S/C30H22O10/c31-15-5-1-13(2-6-15)29-25(27(37)23-19(35)9-17(33)11-21(23)39-29)26-28(38)24-20(36)10-18(34)12-22(24)40-30(26)14-3-7-16(32)8-4-14/h1-12,25-26,29-36H/t25-,26+,29+,30-
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 Isochamaejasmine

The roots of Stellera chamaejasme Linn.

Biological Activity of Isochamaejasmine

DescriptionIsochamaejasmine has inhibition of NF-kappaB activation, which could reverse the anti-apoptotic effect; it induces apoptosis in leukemia cells by inhibiting the activity of Bcl-2 family proteins, providing evidence for further studying the underlying anti-cancer mechanism of S. chamaejasme L. Isochamaejasmine shows antiplasmodial activity, with an IC(50) of 7.3+/-3.8 microM, but the selectivity was rather limited.
TargetsNF-kB | PKC | p38MAPK | ERK | Bcl-2/Bax | Caspase | PARP | Antifection
In vitro

Stereospecific induction of nuclear factor-kappaB activation by isochamaejasmin.[Pubmed: 16141313]

Mol Pharmacol. 2005 Dec;68(6):1534-42.

The root of Stellera chamaejasme L. is a traditional Chinese herb termed Rui Xiang Lang Du and has been used to treat solid tumors, tuberculosis and psoriasis. Exactly how S. chamaejasme L. regulates cellular responses remains unclear.
METHODS AND RESULTS:
We examined four biflavonoids isolated from S. chamaejasme L., including isochamaejasmin(Isochamaejasmine), two of its stereo-isomers and a methyl derivative, in functional assays originally designed to screen ligands for the G protein-coupled formyl peptide receptor-like 1 (FPRL1). Isochamaejasmin(Isochamaejasmine) was found to induce the expression of a nuclear factor (NF)-kappaB-directed reporter gene in transfected HeLa cells with an EC50 of 3.23 microM, independently of FPRL1. The isochamaejasmin-stimulated NF-kappaB reporter activity was accompanied by nuclear translocation of NF-kappaB proteins and was blocked by a dominant-negative construct of IkappaBalpha. Isochamaejasmin(Isochamaejasmine) also induced time-dependent phosphorylation of the mitogen-activated protein kinases extracellular signal-regulated kinase 1/2 and p38, and a novel protein kinase C (PKCdelta). Likewise, inhibition of these kinases with the respective pharmacological inhibitors significantly reduced the isochamaejasmin(Isochamaejasmine)-stimulated NF-kappaB activation. It is noteworthy that the two stereoisomers and the methyl derivative did not induce detectable activation of NF-kappaB and were more cytotoxic than isochamaejasmin, which could partially rescue cycloheximide-induced apoptosis. Inhibition of NF-kappaB activation reversed the anti-apoptotic effect of isochamaejasmin(Isochamaejasmine).
CONCLUSIONS:
These results provide the first evidence for a potential mechanism of action by S. chamaejasme L., and indicate that structurally similar compounds derived from S. chamaejasme L. may have different pharmacological properties.

Antiplasmodial activity of (I-3,II-3)-biflavonoids and other constituents from Ormocarpum kirkii.[Pubmed: 20189612 ]

Phytochemistry. 2010 May;71(7):785-91.

Preliminary screening of a series of medicinal plants, traditionally used in Tanzania, showed an IC(50) of 15.6-31.2 microg/ml for the crude extract of the root of Ormocarpum kirkii S. Moore (Papilionaceae) against Plasmodium falciparum. A bioguided isolation was performed in order to isolate the active constituents.
METHODS AND RESULTS:
Twelve constituents were obtained and identified using NMR and MS data, and optical rotation measurements. The compounds comprised seven (I-3,II-3)-biflavonoids, three (I-3,II-3)-bi-4-phenyldihydrocoumarins, an isoflavanone and a C-glucosylated flavone. Six compounds, liquiritigeninyl-(I-3,II-3)-naringenin, apigeninyl-(I-3,II-3)-naringenin, 7-O-beta-D-glucopyranosylchamaejasmin, (3R,4S,3''R,4''S)-5,5''-di-O-methyldiphysin, 7-O-beta-D-glucopyranosyldiphysin, and 4''-hydroxydiphysolone, were isolated in addition to six known components. The compounds were evaluated for antimicrobial activity in a broad screening panel, including P. falciparum. Seven of these showed antiplasmodial activity; isochamaejasmin(Isochamaejasmine) being the most active with an IC(50) of 7.3+/-3.8 microM, but the selectivity was rather limited.
CONCLUSIONS:
Thus, these constituents may contribute, at least in part, to the antimalarial use of O. kirkii in traditional medicine.

Protocol of Isochamaejasmine

Kinase Assay

Isochamaejasmin induces apoptosis in leukemia cells through inhibiting Bcl-2 family proteins.[Pubmed: 26412425]

Chinese Journal of Natural Medicines,2015,13(9):660-6.

The biflavonoid isochamaejasmin is mainly distributed in the root of Stellera chamaejasme L. (Thymelaeaceae) that is used in traditional Chinese medicine (TCM) to treat tumors, tuberculosis, and psoriasis.
METHODS AND RESULTS:
Herein, isochamaejasmin(Isochamaejasmine) was found to show similar bioactivity against Bcl-2 family proteins to the reference Bcl-2 ligand (-)-gossypol through 3D similarity search. It selectively bound to Bcl-xl and Mcl-1 with Ki values being 1.93 ± 0.13 μmol·L(-1) and 9.98 ± 0.21 μmol·L(-1), respectively. In addition, isochamaejasmin (Isochamaejasmine) showed slight growth inhibitory activity against HL-60 with IC50 value being 50.40 ± 1.21 μmol·L(-1) and moderate growth inhibitory activity against K562 cells with IC50 value being 24.51 ± 1.62 μmol·L(-1). Furthermore, isochamaejasmin(Isochamaejasmine) induced apoptosis of K562 cells by increasing the intracellular expression levels of proteins of the cleavage of caspase-9, caspase-3, and PARP which involved in the Bcl-2-induced apoptosis pathway.
CONCLUSIONS:
These results indicated that isochamaejasmin(Isochamaejasmine) induces apoptosis in leukemia cells by inhibiting the activity of Bcl-2 family proteins, providing evidence for further studying the underlying anti-cancer mechanism of S. chamaejasme L.

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Preparing Stock Solutions of Isochamaejasmine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.8433 mL 9.2166 mL 18.4332 mL 36.8664 mL 46.0829 mL
5 mM 0.3687 mL 1.8433 mL 3.6866 mL 7.3733 mL 9.2166 mL
10 mM 0.1843 mL 0.9217 mL 1.8433 mL 3.6866 mL 4.6083 mL
50 mM 0.0369 mL 0.1843 mL 0.3687 mL 0.7373 mL 0.9217 mL
100 mM 0.0184 mL 0.0922 mL 0.1843 mL 0.3687 mL 0.4608 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 Isochamaejasmine

Stereospecific induction of nuclear factor-kappaB activation by isochamaejasmin.[Pubmed:16141313]

Mol Pharmacol. 2005 Dec;68(6):1534-42.

The root of Stellera chamaejasme L. is a traditional Chinese herb termed Rui Xiang Lang Du and has been used to treat solid tumors, tuberculosis and psoriasis. Exactly how S. chamaejasme L. regulates cellular responses remains unclear. We examined four biflavonoids isolated from S. chamaejasme L., including isochamaejasmin, two of its stereo-isomers and a methyl derivative, in functional assays originally designed to screen ligands for the G protein-coupled formyl peptide receptor-like 1 (FPRL1). Isochamaejasmin was found to induce the expression of a nuclear factor (NF)-kappaB-directed reporter gene in transfected HeLa cells with an EC50 of 3.23 microM, independently of FPRL1. The isochamaejasmin-stimulated NF-kappaB reporter activity was accompanied by nuclear translocation of NF-kappaB proteins and was blocked by a dominant-negative construct of IkappaBalpha. Isochamaejasmin also induced time-dependent phosphorylation of the mitogen-activated protein kinases extracellular signal-regulated kinase 1/2 and p38, and a novel protein kinase C (PKCdelta). Likewise, inhibition of these kinases with the respective pharmacological inhibitors significantly reduced the isochamaejasmin-stimulated NF-kappaB activation. It is noteworthy that the two stereoisomers and the methyl derivative did not induce detectable activation of NF-kappaB and were more cytotoxic than isochamaejasmin, which could partially rescue cycloheximide-induced apoptosis. Inhibition of NF-kappaB activation reversed the anti-apoptotic effect of isochamaejasmin. These results provide the first evidence for a potential mechanism of action by S. chamaejasme L., and indicate that structurally similar compounds derived from S. chamaejasme L. may have different pharmacological properties.

Antiplasmodial activity of (I-3,II-3)-biflavonoids and other constituents from Ormocarpum kirkii.[Pubmed:20189612]

Phytochemistry. 2010 May;71(7):785-91.

Preliminary screening of a series of medicinal plants, traditionally used in Tanzania, showed an IC(50) of 15.6-31.2 microg/ml for the crude extract of the root of Ormocarpum kirkii S. Moore (Papilionaceae) against Plasmodium falciparum. A bioguided isolation was performed in order to isolate the active constituents. Twelve constituents were obtained and identified using NMR and MS data, and optical rotation measurements. The compounds comprised seven (I-3,II-3)-biflavonoids, three (I-3,II-3)-bi-4-phenyldihydrocoumarins, an isoflavanone and a C-glucosylated flavone. Six compounds, liquiritigeninyl-(I-3,II-3)-naringenin, apigeninyl-(I-3,II-3)-naringenin, 7-O-beta-D-glucopyranosylchamaejasmin, (3R,4S,3''R,4''S)-5,5''-di-O-methyldiphysin, 7-O-beta-D-glucopyranosyldiphysin, and 4''-hydroxydiphysolone, were isolated in addition to six known components. The compounds were evaluated for antimicrobial activity in a broad screening panel, including P. falciparum. Seven of these showed antiplasmodial activity; isochamaejasmin being the most active with an IC(50) of 7.3+/-3.8 microM, but the selectivity was rather limited. Thus, these constituents may contribute, at least in part, to the antimalarial use of O. kirkii in traditional medicine.

Isochamaejasmin induces apoptosis in leukemia cells through inhibiting Bcl-2 family proteins.[Pubmed:26412425]

Chin J Nat Med. 2015 Sep;13(9):660-6.

The biflavonoid isochamaejasmin is mainly distributed in the root of Stellera chamaejasme L. (Thymelaeaceae) that is used in traditional Chinese medicine (TCM) to treat tumors, tuberculosis, and psoriasis. Herein, isochamaejasmin was found to show similar bioactivity against Bcl-2 family proteins to the reference Bcl-2 ligand (-)-gossypol through 3D similarity search. It selectively bound to Bcl-xl and Mcl-1 with Ki values being 1.93 +/- 0.13 mumol.L(-1) and 9.98 +/- 0.21 mumol.L(-1), respectively. In addition, isochamaejasmin showed slight growth inhibitory activity against HL-60 with IC50 value being 50.40 +/- 1.21 mumol.L(-1) and moderate growth inhibitory activity against K562 cells with IC50 value being 24.51 +/- 1.62 mumol.L(-1). Furthermore, isochamaejasmin induced apoptosis of K562 cells by increasing the intracellular expression levels of proteins of the cleavage of caspase-9, caspase-3, and PARP which involved in the Bcl-2-induced apoptosis pathway. These results indicated that isochamaejasmin induces apoptosis in leukemia cells by inhibiting the activity of Bcl-2 family proteins, providing evidence for further studying the underlying anti-cancer mechanism of S. chamaejasme L.

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