Suberosin

CAS# 581-31-7

Suberosin

Catalog No. BCN5791----Order now to get a substantial discount!

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Quality Control of Suberosin

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Chemical structure

Suberosin

3D structure

Chemical Properties of Suberosin

Cas No. 581-31-7 SDF Download SDF
PubChem ID 68486 Appearance Cryst.
Formula C15H16O3 M.Wt 244.3
Type of Compound Coumarins Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 7-methoxy-6-(3-methylbut-2-enyl)chromen-2-one
SMILES CC(=CCC1=C(C=C2C(=C1)C=CC(=O)O2)OC)C
Standard InChIKey RSZDAYHEZSRVHS-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H16O3/c1-10(2)4-5-11-8-12-6-7-15(16)18-14(12)9-13(11)17-3/h4,6-9H,5H2,1-3H3
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 Suberosin

The roots of Angelica pubescens

Biological Activity of Suberosin

DescriptionSuberosin exhibits anti-inflammatory, and anticoagulant activities, it also shows biting deterrent activity against Aedes aegypti, it may be useful for use as mosquito larvicidal agent. Suberosin inhibits PHA-induced PBMC proliferation, at least in part, through reduction of [Ca2+]i, ERK, NF-AT, and NF-kappaB activation, and early gene expression in PBMC including cyclins and cytokines, and arrest of cell cycle progression in the cells.
TargetsIFN-γ | IL Receptor | NF-kB | Calcium Channel | ERK
In vitro

Suberosin inhibits proliferation of human peripheral blood mononuclear cells through the modulation of the transcription factors NF-AT and NF-kappaB.[Pubmed: 17179947]

Br J Pharmacol. 2007 Feb;150(3):298-312.

Extracts of Plumbago zeylanica containing Suberosin exhibit anti-inflammatory activity. We purified Suberosin from such extracts and studied its effects on a set of key regulatory events in the proliferation of human peripheral blood mononuclear cells (PBMC) stimulated by phytohemagglutinin (PHA).
METHODS AND RESULTS:
Proliferation of PBMC in culture was measured by uptake of 3H-thymidine; production of cytokines and cyclins by Western blotting and RT-PCR. Transcription factors NF-AT and NF-kappaB were assayed by immunocytochemistry and EMSA. Suberosin suppressed PHA-induced PBMC proliferation and arrested cell cycle progression from the G1 transition to the S phase. Suberosin suppressed, in activated PBMC, transcripts of interleukin-2 (IL-2), interferon-gamma (IFN-gamma), and cyclins D3, E, A, and B. DNA binding activity and nuclear translocation of NF-AT and NF-kappaB induced by PHA were blocked by Suberosin. Suberosin decreased the rise in intracellular Ca2+ concentration ([Ca2+]i) in PBMC stimulated with PHA. Suberosin did not affect phosphorylation of p38 and JNK but did reduce activation of ERK in PHA-treated PBMC. Pharmacological inhibitors of NF-kappaB, NF-AT, and ERK decreased expression of mRNA for the cyclins, IL-2, and IFN-gamma and cell proliferation in PBMC activated by PHA.
CONCLUSIONS:
The inhibitory effects of Suberosin on PHA-induced PBMC proliferation, were mediated, at least in part, through reduction of [Ca2+]i, ERK, NF-AT, and NF-kappaB activation, and early gene expression in PBMC including cyclins and cytokines, and arrest of cell cycle progression in the cells. Our observations provide an explanation for the anti-inflammatory activity of P. zeylanica.

Structure and in vitro antiparasitic activity of constituents of Citropsis articulata root bark.[Pubmed: 21985060]

J Nat Prod. 2011 Oct 28;74(10):2286-9.

From the results of an ethnomedicinal investigation of plants from Uganda with antimalarial activity, Citropsis articulata was selected because of the antiplasmodial effect of an ethyl acetate extract of its root bark.
METHODS AND RESULTS:
Thus, from the cyclohexane, ethyl acetate, and methanol extracts, two new heterocyclic compounds, omubioside (1) and katimborine (2), were isolated in addition to five known coumarins (rutarin (3), seselin (4), Suberosin (5), demethylSuberosin (6), and haploperoside (7)), two known alkaloids (5-hydroxynoracronycine (8) and 1,5-dihydroxy-2,3-dimethoxy-10-methyl-9-acridone (9)), trigonelline (10), and the limonoid 7α-obacunyl acetate (11). The best growth inhibitors of Plasmodium falciparum were alkaloids 8 and 9, with IC50 values of 0.9 and 3.0 μg/mL.

The identification of suberosin from prangos pabularia essential oil and its mosquito activity against aedes aegypti[Reference: WebLink]

Rec. Nat. Prod. 10:3 (2016) 311-325.

A detailed analysis of Prangos pabularia Lindl. (Apiaceae) fruit oil was performed by gas chromatography (GC-FID) and gas chromatography-mass spectrometry (GC-MS).
METHODS AND RESULTS:
Bicyclogermacrene (21%), (Z)--ocimene (19%), -humulene (8%), -pinene (8%) and spathulenol (6%) were the main constituents of the oil. One compound with 1.8% at RI 3420 remained unidentified or tentatively identified as Suberosin from the Wiley GC-MS Library. The assumed compound, Suberosin was synthesized in two steps and its structure was confirmed by 1D NMR and GC-MS analyses. As part of our continued research to discover new chemicals for use in mosquito control agents as repellents and larvicides, Suberosin and its parent compound coumarin were investigated for the mosquito biting deterrent and larvicidal activity against Aedes aegypti. Both Suberosin and coumarin showed biting deterrent activity but the activity was lower than the positive control, DEET (N,Ndiethyl-3-methylbenzamide). In larval bioassays, Suberosin with LC50 value of 8.1 ppm was significantly more toxic than coumarin (LC50 = 49.6 ppm) at 24-h post treatment.
CONCLUSIONS:
These results indicate that Suberosin may be useful for use as mosquito larvicidal agent.

Protocol of Suberosin

Animal Research

Anticoagulant activity of isolated coumarins (suberosin and suberenol) and toxicity evaluation of Ferulago carduchorum in rats.[Pubmed: 25017518 ]

Pharm Biol. 2014 Oct;52(10):1335-40

Ferulago carduchorum Boiss. & Hausskn. (Apiaceae) is known as Chavil in Persian which grows in west of Iran. Local people add Chavil to dairy and oil ghee as a natural preservative to extend the expiration date. The goal of this survey is the safety evaluation of the total extract of F. carduchorum in rats by determining both oral acute and subchronic toxicities; furthermore, the anticoagulant activity of isolated coumarins was evaluated.
METHODS AND RESULTS:
The aerial parts of F. carduchorum were extracted by the percolation method. The anticoagulant activity of isolated coumarins was evaluated and the total extract was used to investigate acute and subchronic toxicity in rats. In the subchronic toxicity model, doses of 250, 500, and 1000 mg/kg of the extract were administered to treated groups for 30 consecutive days by gavage. According to the results of acute toxicity, the LD50 of Chavil extract was more than 2000 mg/kg. The subchronic study showed no significant difference (p > 0.05) between the groups treated with extract and control groups in hematological (erythrocyte, total and differential leukocyte, hematocrit, hemoglobin, platelet count) and biochemical parameter (glucose, albumin, cholesterol, triglycerides, aspartate aminotransferase, alanine aminotransferase, and alkaline phosphatase) evaluations. The isolated coumarins (Suberosin and suberenol) prolonged the prothrombin time (PT) at doses of 3 and 6 mg/kg compared with control (p < 0.05). The longest PT was for Suberosin at 6 mg/kg (17.4 s).
CONCLUSIONS:
In conclusion, oral administration of the Chavil extract did not cause either acute or subchronic toxicities although the coumarins showed anticoagulant effect in rats.

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Preparing Stock Solutions of Suberosin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.0933 mL 20.4666 mL 40.9333 mL 81.8666 mL 102.3332 mL
5 mM 0.8187 mL 4.0933 mL 8.1867 mL 16.3733 mL 20.4666 mL
10 mM 0.4093 mL 2.0467 mL 4.0933 mL 8.1867 mL 10.2333 mL
50 mM 0.0819 mL 0.4093 mL 0.8187 mL 1.6373 mL 2.0467 mL
100 mM 0.0409 mL 0.2047 mL 0.4093 mL 0.8187 mL 1.0233 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 Suberosin

Suberosin inhibits proliferation of human peripheral blood mononuclear cells through the modulation of the transcription factors NF-AT and NF-kappaB.[Pubmed:17179947]

Br J Pharmacol. 2007 Feb;150(3):298-312.

BACKGROUND AND PURPOSE: Extracts of Plumbago zeylanica containing Suberosin exhibit anti-inflammatory activity. We purified Suberosin from such extracts and studied its effects on a set of key regulatory events in the proliferation of human peripheral blood mononuclear cells (PBMC) stimulated by phytohemagglutinin (PHA). EXPERIMENTAL APPROACH: Proliferation of PBMC in culture was measured by uptake of 3H-thymidine; production of cytokines and cyclins by Western blotting and RT-PCR. Transcription factors NF-AT and NF-kappaB were assayed by immunocytochemistry and EMSA. KEY RESULTS: Suberosin suppressed PHA-induced PBMC proliferation and arrested cell cycle progression from the G1 transition to the S phase. Suberosin suppressed, in activated PBMC, transcripts of interleukin-2 (IL-2), interferon-gamma (IFN-gamma), and cyclins D3, E, A, and B. DNA binding activity and nuclear translocation of NF-AT and NF-kappaB induced by PHA were blocked by Suberosin. Suberosin decreased the rise in intracellular Ca2+ concentration ([Ca2+]i) in PBMC stimulated with PHA. Suberosin did not affect phosphorylation of p38 and JNK but did reduce activation of ERK in PHA-treated PBMC. Pharmacological inhibitors of NF-kappaB, NF-AT, and ERK decreased expression of mRNA for the cyclins, IL-2, and IFN-gamma and cell proliferation in PBMC activated by PHA. CONCLUSIONS AND IMPLICATIONS: The inhibitory effects of Suberosin on PHA-induced PBMC proliferation, were mediated, at least in part, through reduction of [Ca2+]i, ERK, NF-AT, and NF-kappaB activation, and early gene expression in PBMC including cyclins and cytokines, and arrest of cell cycle progression in the cells. Our observations provide an explanation for the anti-inflammatory activity of P. zeylanica.

Structure and in vitro antiparasitic activity of constituents of Citropsis articulata root bark.[Pubmed:21985060]

J Nat Prod. 2011 Oct 28;74(10):2286-9.

From the results of an ethnomedicinal investigation of plants from Uganda with antimalarial activity, Citropsis articulata was selected because of the antiplasmodial effect of an ethyl acetate extract of its root bark. Thus, from the cyclohexane, ethyl acetate, and methanol extracts, two new heterocyclic compounds, omubioside (1) and katimborine (2), were isolated in addition to five known coumarins (rutarin (3), seselin (4), Suberosin (5), demethylSuberosin (6), and haploperoside (7)), two known alkaloids (5-hydroxynoracronycine (8) and 1,5-dihydroxy-2,3-dimethoxy-10-methyl-9-acridone (9)), trigonelline (10), and the limonoid 7alpha-obacunyl acetate (11). The best growth inhibitors of Plasmodium falciparum were alkaloids 8 and 9, with IC50 values of 0.9 and 3.0 mug/mL.

Anticoagulant activity of isolated coumarins (suberosin and suberenol) and toxicity evaluation of Ferulago carduchorum in rats.[Pubmed:25017518]

Pharm Biol. 2014 Oct;52(10):1335-40.

CONTEXT: Ferulago carduchorum Boiss. & Hausskn. (Apiaceae) is known as Chavil in Persian which grows in west of Iran. Local people add Chavil to dairy and oil ghee as a natural preservative to extend the expiration date. OBJECTIVE: The goal of this survey is the safety evaluation of the total extract of F. carduchorum in rats by determining both oral acute and subchronic toxicities; furthermore, the anticoagulant activity of isolated coumarins was evaluated. MATERIALS AND METHODS: The aerial parts of F. carduchorum were extracted by the percolation method. The anticoagulant activity of isolated coumarins was evaluated and the total extract was used to investigate acute and subchronic toxicity in rats. In the subchronic toxicity model, doses of 250, 500, and 1000 mg/kg of the extract were administered to treated groups for 30 consecutive days by gavage. RESULTS: According to the results of acute toxicity, the LD50 of Chavil extract was more than 2000 mg/kg. The subchronic study showed no significant difference (p > 0.05) between the groups treated with extract and control groups in hematological (erythrocyte, total and differential leukocyte, hematocrit, hemoglobin, platelet count) and biochemical parameter (glucose, albumin, cholesterol, triglycerides, aspartate aminotransferase, alanine aminotransferase, and alkaline phosphatase) evaluations. The isolated coumarins (Suberosin and suberenol) prolonged the prothrombin time (PT) at doses of 3 and 6 mg/kg compared with control (p < 0.05). The longest PT was for Suberosin at 6 mg/kg (17.4 s). CONCLUSION: In conclusion, oral administration of the Chavil extract did not cause either acute or subchronic toxicities although the coumarins showed anticoagulant effect in rats.

Description

Suberosin, isolated from Plumbago zeylanica, exhibits anti-inflammatory and anticoagulant activity. Suberosin suppresses PHA-induced PBMC proliferation and arrested cell cycle progression from the G1 transition to the S phase through the modulation of the transcription factors NF-AT and NF-κB.

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