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Home > Products >  Benzoylmesaconine

Benzoylmesaconine CAS NO.63238-67-5

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Keywords

  • Benzoylmesaconine
  • 63238-67-5
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Quick Details

  • ProName: Benzoylmesaconine
  • CasNo: 63238-67-5
  • Molecular Formula: C31H43NO10
  • Appearance: detailed see specifications
  • Application: analysis,activity test,Botanical Refer...
  • DeliveryTime: 1-3?working?days?after?confirming?the?...
  • PackAge: According to the clients requirement.
  • Port: China main port
  • ProductionCapacity: 1 Metric Ton/Day
  • Purity: ≥98%
  • Storage: Store at 2~8°C
  • Transportation: by air or by ocean shipping
  • LimitNum: 10 Milligram
  • Plant of Origin: Chinese herbal medicine
  • Testing Method: NMR/MS/HPLC
  • Product Ecification: 1mg-1kg
  • Heavy Metal: <10ppm
  • Voluntary Standards: company standard
  • Storage: Store in dry, dark and ventilated plac...
  • PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers. 
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.
 
Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library
 

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of Byakangelicol

Cas No. 26091-79-2    
PubChem ID 3055167 Appearance White powder
Formula C17H16O6 M.Wt 316.31
Type of Compound Coumarins Storage Desiccate at -20°C
Synonyms Biacangelicol
Solubility Soluble in chloroform, methanol and pyridine
Chemical Name 9-[[(2R)-3,3-dimethyloxiran-2-yl]methoxy]-4-methoxyfuro[3,2-g]chromen-7-one
SMILES CC1(C(O1)COC2=C3C(=C(C4=C2OC(=O)C=C4)OC)C=CO3)C
Standard InChIKey ORBITTMJKIGFNH-LLVKDONJSA-N
Standard InChI InChI=1S/C17H16O6/c1-17(2)11(23-17)8-21-16-14-10(6-7-20-14)13(19-3)9-4-5-12(18)22-15(9)16/h4-7,11H,8H2,1-3H3/t11-/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 Byakangelicol

1 Citrus sp. 2 Heracleum sp. 3 Murraya sp. 4 Peucedanum sp. 5 Stauranthus sp.

Biological Activity of Byakangelicol

Description Byakangelicol exhibits hepatoprotective activities on tacrine-induced cytotoxicity in Hep G2 cells, with EC(50) values of 112.7 +/- 5.35 microM. Byakangelicol may have therapeutic potential as an anti-inflammatory drug on airway inflammation, it can inhibit IL-1beta-induced PGE2 release in A549 cells; this inhibition may be mediated by suppression of COX-2 expression and the activity of COX-2 enzyme, it also can inhibit P-gp expressed. Byakangelicol shows a significant inhibition on the proliferation of cultured human tumor cells.
Targets COX | PGE | IL Receptor | MAPK | p65 | P-gp | NF-kB
In vitro

Byakangelicol, isolated from Angelica dahurica, inhibits both the activity and induction of cyclooxygenase-2 in human pulmonary epithelial cells.[Pubmed: 12356282]

J Pharm Pharmacol. 2002 Sep;54(9):1271-8.

We examined the inhibitory mechanism of Byakangelicol, isolated from Angelica dahurica, on interleukin-1beta (IL-1beta)-induced cyclooxygenase-2 (COX-2) expression and prostaglandin E2 (PGE2) release in human pulmonary epithelial cell line (A549).
METHODS AND RESULTS:
Byakangelicol (10-50 microM) concentration-dependently attenuated IL-1beta-induced COX-2 expression and PGE2 release. The selective COX-2 inhibitor, NS-398 (0.01-1 microM), and Byakangelicol (10-50 microM) both concentration-dependently inhibited the activity of the COX-2 enzyme. Byakangelicol, at a concentration up to 200 microM, did not affect the activity and expression of COX-1 enzyme. IL-1beta-induced p44/42 mitogen-activated protein kinase (MAPK) activation was inhibited by the MAPK/extracellular signal-regulated protein kinase (MEK) inhibitor, PD 98059 (30 microM), while Byakangelicol (50 microM) had no effect. Treatment of cells with Byakangelicol (50 microM) or pyrrolidine dithiocarbamate (PDTC; 50 microM) partially inhibited IL-1beta-induced degradation of IkappaB-alpha in the cytosol, translocation of p65 NF-kappaB from the cytosol to the nucleus and the NF-kappaB-specific DNA-protein complex formation.
CONCLUSIONS:
Taken together, we have demonstrated that Byakangelicol inhibits IL-1beta-induced PGE2 release in A549 cells; this inhibition may be mediated by suppression of COX-2 expression and the activity of COX-2 enzyme. The inhibitory mechanism of Byakangelicol on IL-1beta-induced COX-2 expression may be, at least in part, through suppression of NF-kappaB activity. Therefore, Byakangelicol may have therapeutic potential as an anti-inflammatory drug on airway inflammation.

Antiproliferative effect of furanocoumarins from the root of Angelica dahurica on cultured human tumor cell lines.[Pubmed: 17143927 ]

Phytother Res. 2007 Mar;21(3):288-90.

A bioassay-guided fractionation of the root extract of Angelica dahurica (Umbelliferae) led to the isolation of six furanocoumarins as active ingredients responsible for the antitumoral property.
METHODS AND RESULTS:
The hexane soluble part of the extract demonstrated a significant inhibition on the proliferation of cultured human tumor cells such as A549 (non small cell lung), SK-OV-3 (ovary), SK-MEL-2 (melanoma), XF498 (central nervous system) and HCT-15 (colon) in vitro, whereas the remaining water soluble part exhibited poor inhibition.
CONCLUSIONS:
Intensive investigation of the hexane soluble part of the extract yielded six furanocoumarins, i.e. isoimperatorin, cnidicin, imperatorin, oxypeucedanin, Byakangelicol, oxypeucedanin hydrate, all of which exhibited a significant inhibition on cell proliferation in a dose-dependent manner.

Protocol of Byakangelicol

Kinase Assay

Inhibitory effects of furanocoumarin derivatives in Kampo extract medicines on P-glycoprotein at the blood-brain barrier.[Pubmed: 21804213]

Biol Pharm Bull. 2011;34(8):1246-51.

Furanocoumarin derivatives, known as components of grapefruit juice, showing inhibitory effects against P-glycoprotein (P-gp) in the intestine are also contained in the plants of rutaceae and umbelliferae families, which are used as components of Kampo extract medicines. In this study, we investigated the inhibitory effects of Byakangelicol and rivulobirin A, known as furanocoumarins showing P-gp inhibitory effect using Caco-2 monolayer, against P-gp at the blood-brain barrier (BBB) under both in vitro and in vivo conditions.
METHODS AND RESULTS:
First we studied the membrane permeability of furanocoumarins to clarify whether they can be absorbed from the intestine. Both furanocoumarins showed high permeability through the Caco-2 monolayer, suggesting that they can easily reach the systemic circulation after oral administration. Then, we evaluated the effect of these furanocoumarins on the uptake of calcein acetoxymethyl ester (calcein-AM), a P-gp substrate, into bovine brain microvascular endothelial cells (BBMEC). Both furanocoumarins significantly increased the uptake amount of calcein-AM into BBMEC by the inhibition of P-gp at the BBB in vitro. Next we also investigated the P-gp inhibitory effect of these furanocoumarins at the rat BBB in vivo using verapamil as a P-gp substrate. Both furanocoumarins increased the B/P ratio of verapamil compared to the control, even under in vivo conditions; however, the extent of the inhibitory effect was much lower than in vitro condition.
CONCLUSIONS:
In conclusion, Byakangelicol and rivulobirin A may inhibit P-gp expressed at the BBB even under in vivo conditions. Further studies using Kampo extract medicines under in vivo condition are necessary for safe drug therapy.

Cell Research

Furocoumarins from Angelica dahurica with hepatoprotective activity on tacrine-induced cytotoxicity in Hep G2 cells.[Pubmed: 12058329 ]

Planta Med. 2002 May;68(5):463-4.

Fractionation of the MeOH extract of Angelica dahurica Benth et Hook resulted in the isolation of six furocoumarins, imperatorin (1), isoimperatorin (2), (+/-)-Byakangelicol (3), (+)-oxypeucedanin (4), (+)-byakangelicin (5), and (+)-aviprin (6).
METHODS AND RESULTS:
Among these, compounds 1 and 5 exhibited strong hepatoprotective activities, displaying EC(50) values of 36.6 +/- 0.98 and 47.9 +/- 4.6 microM, respectively. Compounds 3 and 4 showed moderate activities with EC(50) values of 112.7 +/- 5.35 and 286.7 +/- 6.36 microM, respectively. Silybin as a positive control showed the EC(50) value with 69.0 +/- 3.4 microM.
CONCLUSIONS:
Comparison of hepatoprotective activities for six furocoumarins 1 - 6 suggested that oxy-substitution at the C-9 position increased the hepatoprotective activity.

Preparing Stock Solutions of Byakangelicol

  1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1615 mL 15.8073 mL 31.6146 mL 63.2291 mL 79.0364 mL
5 mM 0.6323 mL 3.1615 mL 6.3229 mL 12.6458 mL 15.8073 mL
10 mM 0.3161 mL 1.5807 mL 3.1615 mL 6.3229 mL 7.9036 mL
50 mM 0.0632 mL 0.3161 mL 0.6323 mL 1.2646 mL 1.5807 mL
100 mM 0.0316 mL 0.1581 mL 0.3161 mL 0.6323 mL 0.7904 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.

References on Benzoylmesaconine

Therapeutic effects of IL-12 combined with benzoylmesaconine, a non-toxic aconitine-hydrolysate, against herpes simplex virus type 1 infection in mice following thermal injury.[Pubmed:12543043]

Burns. 2003 Feb;29(1):37-42.

IL-12 is an inducer of type 1 T cell responses, which are essential in host defense against herpes simplex virus type 1 (HSV-1) infection. However, type 1 T cell responses are not elicited by IL-12 in thermally injured mice (TI-mice) that routinely have a predominance of burn-associated type 2 T cell responses. In our previous studies, Benzoylmesaconine (BEN, an aconitine derivative extracted from heated-Aconiti tuber) induced the generation of CD4+ T cells antagonistic to type 2 T cells (BEN-CD4+ T cells). In the present study, the effects of a combination therapy using IL-12 and BEN to treat severe HSV-1 infection in TI-mice were investigated. When TI-mice were treated with either IL-12 (500 U per mouse) or BEN (1 microg/kg) alone, they did not resist HSV-1 infection. However, 60-80% of TI-mice exposed to HSV-1 survived after they received IL-12 and BEN or BEN-CD4+ T cells in combination. After stimulation with anti-CD3 mAb in vitro, IFN- was not produced in cultures of splenic T cells from TI-mice exposed to HSV-1 and treated with either IL-12, BEN or BEN-CD4+ T cell alone. However, IFN- production was induced by the mAb stimulation in the cultures of T cells from infected mice treated with IL-12 and BEN or BEN-CD4+ T cells in combination. These results suggest that the combination therapy of IL-12 (an inducer of type 1 T cell responses) and BEN (an inhibitor of type 2 T cell responses) may protect TI-mice from severe HSV-1 infection.

The regulation of burn-associated infections with herpes simplex virus type 1 or Candida albicans by a non-toxic aconitine-hydrolysate, benzoylmesaconine. Part 1: Antiviral and anti-fungal activities in thermally injured mice.[Pubmed:9682963]

Immunol Cell Biol. 1998 Jun;76(3):202-8.

As compared with normal unburned mice, thermally injured mice have been shown to be 50-100 times more susceptible to HSV type 1 (HSV-1) or Candida albicans infection. Benzoylmesaconine (BEN) improved the resistance of thermally injured mice against infection with HSV-1 or C. albicans to the level observed in normal mice. Mortality rates of normal mice exposed to lethal amounts of these pathogens were not affected by the BEN treatment, while significant survival effects were produced in these mice after treatment with acyclovir (against HSV-1) or amphotericin B (against C. albicans). Benzoylmesaconine did not inhibit the growth of these pathogens in vitro and did not directly reduce the viability of the pathogens. However, burned mice inoculated with CD4+ T cells from BEN-treated mice resisted infections from these pathogens. These results suggested that, through the generation of CD4+ T cells, BEN recovered the impaired resistance of thermally injured mice to infection by HSV-1 or C. albicans.

The regulation of burn-associated infections with herpes simplex virus type 1 or Candida albicans by a non-toxic aconitine-hydrolysate, benzoylmesaconine. Part 2: Mechanism of the antiviral action.[Pubmed:9682964]

Immunol Cell Biol. 1998 Jun;76(3):209-16.

In the accompanying paper, the resistance to infections with HSV type 1 (HSV-1) and Candida albicans was improved in thermally injured mice treated with Benzoylmesaconine (BEN), an aconitine-hydrolysate isolated from heated Aconiti tuber, or inoculated with splenic CD4+ T cells from BEN-treated mice (BEN T cells). In this paper, therefore, the antiviral mechanism of BEN T cells (or BEN) on the improved resistance of burned mice to the HSV-1 infection was studied. Burn-associated CD + CD11b+ TCRgamma/delta+ type-2 T cells have been shown to be a key on the increased susceptibility of thermally injured mice to infection with HSV-1 or C. albicans. The susceptibility of T6S-mice, mice inoculated with 1 x 10(6) cells/mouse of T6S cells (a clone of burn-associated type-2 T cells), to HSV-1 infection was similar to that of thermally injured mice. The adoptive transfer of BEN T cells to T6S-mice restores their impaired resistance to HSV-1 infection. The type-2 cytokine levels in sera of T6S-mice were decreased after inoculation of BEN T cells. BEN T cells inhibited the type-2 cytokine production by T6S cells when they were cocultured in vitro. BEN T cells, characterized as CD4+ CD28+ TCRalpha/beta+ Vicia villosa (VV) lectin-adherent T cells, showed non-specific ability to inhibit the cytokine production by various type-2 T cells. From the results of the cytokine-producing profile, BEN T cells were shown to be a different subset of CD4+ T cells from Th1 and Th2 cells, although these three CD4+ T cells had similar properties phenotypically. BEN T cells were induced in normal mice 1-4 days after the oral treatment of BEN (1 microg/kg or more). These results suggest that, through the induction of antagonistic CD4+ T cells against burn-associated type-2 T cells, BEN may improve the resistance of T6S-mice (or thermally injured mice) to the infection of HSV-1.

[Analgesic effect of benzoylmesaconine].[Pubmed:8282271]

Nihon Yakurigaku Zasshi. 1993 Dec;102(6):399-404.

"Tsumura Shuchi-Bushi Powder for Ethical Dispensing" (TJ-3021) is an herbal drug of processed Aconiti tuber that attenuates its toxicity. A greater part of mesaconitine which is regarded as a main analgesic component in processed Aconiti tuber is hydrolyzed into benzoylmesconine (BM) by its processing. In this study, the analgesic effect of BM was examined in comparison with that of TJ-3021 in mice and rats. BM (10 mg/kg, p.o.) depressed the acetic acid-induced writhing significantly. Its analgesic activity was almost similar in magnitude to that of TJ-3021 (300 mg/kg, p.o.). BM (30 mg/kg, p.o.) significantly increased the pain threshold ratio of paw pressure in repeated cold stress (RCS) rats, and its analgesic potency appeared to be equivalent to that of TJ-3021 (1000 mg/kg, p.o.). These results suggest that the analgesic activity of BM is strong enough for explanation of the analgesic effect of TJ-3021, and it might contribute to that of TJ-3021.

Description

Benzoylmesaconine is the most abundant component of Wutou decoction, which is widely used in China because of its therapeutic effect on rheumatoid arthritis.

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