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Cepharadione A

CAS# 55610-01-0

Cepharadione A

Catalog No. BCN3950----Order now to get a substantial discount!

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Cepharadione A: 5mg $903 In Stock
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Quality Control of Cepharadione A

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Chemical structure

Cepharadione A

3D structure

Chemical Properties of Cepharadione A

Cas No. 55610-01-0 SDF Download SDF
PubChem ID 94577 Appearance Yellow powder
Formula C18H11NO4 M.Wt 305.3
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CN1C2=CC3=CC=CC=C3C4=C2C(=CC5=C4OCO5)C(=O)C1=O
Standard InChIKey RZIGKFTVXWUUCX-UHFFFAOYSA-N
Standard InChI InChI=1S/C18H11NO4/c1-19-12-6-9-4-2-3-5-10(9)15-14(12)11(16(20)18(19)21)7-13-17(15)23-8-22-13/h2-7H,8H2,1H3
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 Cepharadione A

The herbs of Piper longum

Biological Activity of Cepharadione A

Description1. Cepharadione A, a naturally occurring DNA damaging agent.

Cepharadione A Dilution Calculator

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Cepharadione A Molarity Calculator

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Preparing Stock Solutions of Cepharadione A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.2755 mL 16.3773 mL 32.7547 mL 65.5093 mL 81.8867 mL
5 mM 0.6551 mL 3.2755 mL 6.5509 mL 13.1019 mL 16.3773 mL
10 mM 0.3275 mL 1.6377 mL 3.2755 mL 6.5509 mL 8.1887 mL
50 mM 0.0655 mL 0.3275 mL 0.6551 mL 1.3102 mL 1.6377 mL
100 mM 0.0328 mL 0.1638 mL 0.3275 mL 0.6551 mL 0.8189 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 Cepharadione A

Phenanthrene derivatives from roots and rhizomes of Asarum heterotropoides var. mandshuricum.[Pubmed:28126415]

Fitoterapia. 2017 Mar;117:101-108.

Five new phenanthrene derivatives: 9-ethoxy-7-methoxy-aristololactam IV (1), norCepharadione A N-beta-d-glucopyranoside (2), aristololactamoside I (3), aristololactamoside II (4) and aristothiolactoside (5) together with eleven known phenanthrene derivatives (6-16) were isolated from the ethanol extract of the roots and rhizomes of Asarum heterotropoides var. mandshuricum. The aristololactams with substitution of ethoxy at C-9 position (1, 9, and 10) and the sulfur-containing phenanthrene derivative (5) were reported in the genus Asarum for the first time. Furthermore, six phenanthrene glucoside derivatives (2-5, 13 and 14) were also found in this genus for the first time and compounds 7 and 9-15 were isolated from the genus Asarum for the first time. Six of them (1, 2, 9, 10, 13 and 14) were submitted to cytotoxicity test against human renal proximal tubular epithelial cell lines (HK-2) using MTT and LDH assays. Compounds 1 and 10 showed significant cytotoxic activity against HK-2 cell lines with IC50 values of 18.18 and 20.44mumol/L in MTT assay and 84.36 and 35.06mumol/L in LDH assay, respectively. Compound 9 showed moderate cytotoxicity in MTT assay with IC50 values of 95.60mumol/L, but no cytotoxicity in LDH assay. Compounds 2, 13 and 14 showed cytotoxic effect in neither MTT assay nor LDH assay. Considering the other nephrotoxic phenanthrene derivatives (6, 8, 12, 15 and 16) previously tested, the results implied the potency of renal toxicity of this herb used as a medicine.

Is aristolochic acid nephropathy a widespread problem in developing countries? A case study of Aristolochia indica L. in Bangladesh using an ethnobotanical-phytochemical approach.[Pubmed:23806867]

J Ethnopharmacol. 2013 Aug 26;149(1):235-44.

ETHNOPHARMACOLOGICAL RELEVANCE: Species of Aristolochia are associated with aristolochic acid nephropathy (AAN), a renal interstitial fibrosis and upper urinary tract cancer (UUC). Aristolochic acid nephropathy has been reported in ten countries but its true incidence is unknown and most likely underestimated. By combining an ethnobotanical and phytochemical approach we provide evidence for the risk of AAN occurring in Bangladesh. More specifically, we assess the intra-specific variation of aristolochic acid analogues in medicinally used Aristolochia indica samples from Bangladesh. MATERIALS AND METHODS: Ethnobotanical information was collected from 16 kavirajes (traditional healers) in different study locations in Bangladesh. Plant samples were obtained from native habitats, botanical gardens, herbal markets and pharmaceutical companies. The samples were extracted using 70% methanol and were analysed using LC-DAD-MS and (1)H-NMR. RESULTS: Roots as well as leaves are commonly used for symptoms such as snake bites and sexual problems. Among the informants knowledge about toxicity or side effects is very limited and Aristolochia indica is often administered in very high doses. Replacement of Aristolochia indica with other medicinal plants such as Rauvolfia serpentina (L.) Benth. ex Kurz was common. Aristolochia indica samples contained a variety of aristolochic acid analogues such as aristolochic acid I, aristolochic acid II, Cepharadione A and related compounds. CONCLUSIONS: AAN cases are likely to occur in Bangladesh and more awareness needs to be raised about the health risks associated with the use of Aristolochia indica and other species of Aristolochia as herbal medicines.

A new hydroxychavicol dimer from the roots of Piper betle.[Pubmed:23442932]

Molecules. 2013 Feb 26;18(3):2563-70.

A new hydroxychavicol dimer, 2-(g'-hydroxychavicol)-hydroxychavicol (1), was isolated from the roots of Piper betle Linn. along with five known compounds, hydroxychavicol (2), aristololactam A II (3), aristololactam B II (4), piperolactam A (5) and Cepharadione A (6). The structures of these isolated compounds were elucidated by spectroscopic methods. Compounds 1 and 2 exhibited inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

Alkaloids from Piper sarmentosum and Piper nigrum.[Pubmed:19809914]

Nat Prod Res. 2009;23(15):1416-23.

Detailed chemical studies on the roots of Piper sarmentosum and Piper nigrum have resulted in several alkaloids. The roots of P. sarmentosum gave a new aromatic compound, 1-nitrosoimino-2,4,5-trimethoxybenzene (1). Piper nigrum roots gave pellitorine (2), (E)-1-[3',4'-(methylenedioxy)cinnamoyl]piperidine (3), 2,4-tetradecadienoic acid isobutyl amide (4), piperine (5), sylvamide (6), Cepharadione A (7), piperolactam D (8) and paprazine (9). Structural elucidation of these compounds was achieved through NMR and MS techniques. Cytotoxic activity screening of the plant extracts indicated some activity.

Synthesis and biological evaluation of cepharadiones A and B and related dioxoaporphines.[Pubmed:17624787]

Bioorg Med Chem. 2007 Sep 15;15(18):6119-25.

Described herein is the first total synthesis and structural confirmation of Cepharadione A, a naturally occurring DNA damaging agent. Also reported is the synthesis of cepharadione B, a closely related natural product, as well as the biological evaluation of both natural products. Finally, the preparation and biological evaluation of novel dioxoaporphine analogues is described.

A DNA-damaging oxoaporphine alkaloid from Piper caninum.[Pubmed:15270572]

J Nat Prod. 2004 Jul;67(7):1162-4.

Bioassay-guided fractionation of an active organic extract of Piper caninum, using a sensitive yeast assay to monitor putative double-strand DNA-damaging activity, resulted in the isolation of the 4,5-dioxoaporphine alkaloid Cepharadione A (1). Compound 1 exhibited potent inhibitory activity in a yeast cytotoxicity assay with IC(50) values of 50.2 nM toward RS321NpRAD52 grown on glucose versus 293 nM toward the same yeast strain grown on galactose.

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