Anemoside B4

CAS# 129741-57-7

Anemoside B4

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Quality Control of Anemoside B4

Number of papers citing our products

Chemical structure

Anemoside B4

3D structure

Chemical Properties of Anemoside B4

Cas No. 129741-57-7 SDF Download SDF
PubChem ID 71307558 Appearance Powder
Formula C59H96O26 M.Wt 1221.38
Type of Compound Triterpenoids Storage Desiccate at -20°C
Synonyms Anemoside B4
Solubility DMSO : 125 mg/mL (102.34 mM; Need ultrasonic)
Chemical Name [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] (1R,3aS,5aR,5bR,7aR,8R,9S,11aR,11bR,13aR,13bS)-9-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-8-(hydroxymethyl)-5a,5b,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
SMILES CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OCC3C(C(C(C(O3)OC(=O)C45CCC(C4C6CCC7C8(CCC(C(C8CCC7(C6(CC5)C)C)(C)CO)OC9C(C(C(CO9)O)O)OC1C(C(C(C(O1)C)O)O)O)C)C(=C)C)O)O)O)CO)O)O)O
Standard InChIKey OUHBKBTZUPLIIA-QEEGUAPESA-N
Standard InChI InChI=1S/C59H96O26/c1-23(2)26-11-16-59(54(75)85-52-45(73)41(69)38(66)30(81-52)21-77-49-46(74)42(70)47(29(19-60)80-49)83-50-43(71)39(67)35(63)24(3)78-50)18-17-57(7)27(34(26)59)9-10-32-55(5)14-13-33(56(6,22-61)31(55)12-15-58(32,57)8)82-53-48(37(65)28(62)20-76-53)84-51-44(72)40(68)36(64)25(4)79-51/h24-53,60-74H,1,9-22H2,2-8H3/t24-,25-,26-,27+,28-,29+,30+,31+,32+,33-,34-,35-,36-,37-,38+,39+,40+,41-,42+,43+,44+,45+,46+,47+,48+,49+,50-,51-,52-,53-,55-,56-,57+,58+,59-/m0/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 Anemoside B4

The herb of Pulsatilla chinensis (Bge.) Regel

Biological Activity of Anemoside B4

Description1. Anemoside B4(AB4) and tetrandrine(Tet) have some reversal effect on resistant to L-OHP in Lo Vo/L-OHP cells, the molecular mechanism of the resistance reverse effect was related to down-regulation of P-gp for AB4 and down-regulation of z DHHC9 for Tet. 2. Anemoside B4 can inhibit the production of IL-6,secretion of IL-8, downregulate E-selectin expression, and decrease the content of TXB(2), it reduces inflammatory response, thus relieving intestinal dysfunction via multiple pathways. 3. Anemoside B4 may potentially have a capacity to regulate immune responses in vivo via changes in production of these select cytokines by infected endothelial cells.
TargetsP-gp | IL Receptor | Bcl-2/Bax
In vitro

Chinese herbal medicinal ingredients inhibit secretion of IL-6, IL-8, E-selectin and TXB2 in LPS-induced rat intestinal microvascular endothelial cells.[Pubmed: 19874221 ]

Immunopharmacol Immunotoxicol. 2009;31(4):550-5.


METHODS AND RESULTS:
The aim of the research was to investigate the anti-inflammatory mechanism of Pulsatillae Decoction (PD), the levels of interleukin (IL)-6, IL-8, E-selectin, and thromboxane B(2) (TXB(2)) secreted by cultured rat intestinal microvascular endothelial cells (RIMECs) were determined after treatment with its active ingredients, namely Anemoside B4, anemonin, berberine, jatrorrhizine, palmatine, aesculin, and esculetin. RIMECs were challenged with 1 microg/mL lipopolysaccharide (LPS) for 3 h, and then treated with each of the seven ingredients at three concentrations (1, 5 and 10 microg/mL) for 24 h. The results revealed that anemonin, aesculin and esculetin inhibited the production of IL-6, aesculin and esculetin inhibited the secretion of IL-8, Anemoside B4, berberine and jatrorrhizine downregulated E-selectin expression, anemonin, berberine, jatrorrhizine and palmatine decreased the content of TXB(2). All these changes were significant.
CONCLUSIONS:
Taken together, the data suggest that all seven active ingredients of PD can effectively reduce inflammatory response, thus relieving intestinal dysfunction via multiple pathways.

Cytotoxicity of the compounds isolated from Pulsatilla chinensis saponins and apoptosis induced by 23-hydroxybetulinic acid.[Pubmed: 25026337]

Pharm Biol. 2015 Jan;53(1):1-9.

The rizoma of Pulsatilla chinensis (Bunge) Regel has been used as a traditional Chinese medicinal herb for thousands of years. Total saponins from P. chinensis can induce the apoptosis of solid cancer cells; however, their activity on chronic myeloid leukemia and the mechanisms remains unknown. To study the activity of total saponins and the main active fractions from P. chinensis saponins on chronic myeloid leukemia, and to illustrate the mechanisms underlying the anticancer activities.
METHODS AND RESULTS:
The cytotoxic activity were assayed by MTT; cell cycle arrest and apoptosis were tested by flow cytometry system; changes in the mitochondrial membrane potential were determined using JC-1; and the apoptosis signaling pathway was determined by western blotting. We demonstrated that total P. chinensis saponin displayed cytotoxic activity against K562 cell line. In addition, we identified 23-hydroxybetulinic acid (HBA), pulchinenoside A (PA), and Anemoside B4 (AB4) from the total saponins, with the most cytotoxic compound HBA. Glycosylation at C3 and C28 of HBA significantly reduces its cytotoxicity. HBA could promote cell cycle arrest at S phase and induce apoptosis via intrinsic pathway. HBA disrupts mitochondrial membrane potential significantly (p < 0.01) and selectively downregulates the levels of Bcl-2, survivin and upregulates Bax, cytochrome C, cleaved caspase-9 and -3.
CONCLUSIONS:
Total saponins from P. chinensis may be effective natural products against human chronic myelogenous leukemia; HBA is one of the bioactive components responsible for its anticancer activity, and could be further investigated as an alternative therapeutic drug for leukemia.

Protocol of Anemoside B4

Cell Research

Resistance reverse effect of anemoside B4 and tetrandrine on oxaliplatin-resistant human colon cancer cells and the mechanism[Reference: WebLink]

Role of Chinese herbal medicinal ingredients in secretion of cytokines by PCV2-induced endothelial cells.[Pubmed: 25721049]

J Immunotoxicol. 2016;13(2):141-7.

While T-lymphocytes are the major cell type responsible for host responses to a virus (including induction of inflammatory responses to aid in ultimate removal of virus), other cells, including macrophages, epithelial and dendritic cells also have key roles. Endothelial cells also play important roles in physiologic/pathologic processes, like inflammation, during viral infections. As endothelial cells can be activated to release various endogenous compounds, including some cytokines, ex vivo measures of cytokine formation by the cells can be used to indirectly assess any potential endothelial dysfunction in situ. The research presented here sought to investigate potential immunolomodulatory effects of five saponins on endothelial cells: Saikosaponins A (SSA) and D (SSD), Panax Notoginseng Saponin (PNS) and Notoginsenoside R1 (SR1) and Anemoside B4 (AB4).
METHODS AND RESULTS:
For this, cells (porcine iliac artery endothelial line) were challenged with a virus isolate PCV2-AH for 24 h and then treated with the test saponin (at 1, 5 or 10 μg/ml) for an additional 24 h at 37 °C. The culture supernatants were then collected and analyzed for interleukin (IL)-2, -4 and -10, as well as interferon (IFN)-γ by ELISA. The results revealed that PNS and SR1 inhibited the production of IL-4; PNS, SR1 and AB4 inhibited the secretion of IL-10; SSA, SSD and PNS up-regulated IL-2 expression; SSA and SSD increased the level of IFNγ. All these changes were significant.
CONCLUSIONS:
Taken together, the data suggested these saponins might potentially have a capacity to regulate immune responses in vivo via changes in production of these select cytokines by infected endothelial cells. Nevertheless, the impact of these agents on other key cell types involved in anti-viral responses, including T-lymphocytes, remains to be determined.

China Oncology, 2015(1):38-44.

Oxaliplatin (L-OHP) is one of the most commonly used chemotherapy drugs in colorectal cancer and L-OHP-resistance is very common in colorectal cancer therapy. This research was to discuss the reversal effect in L-OHP-resistant human colon cancer cell line LoVo/L-OHP by Anemoside B4 (AB4) and tetrandrine (Tet) and to clarify their molecular mechanism.
METHODS AND RESULTS:
LoVo/L-OHP cells were treated for 48 h by AB4 and Tet at different concentrations to get non-toxic dose. Drug sensitivity was measured by MTT. After the treatment, the cell cycle and apoptosis of the cells were detected. Expression of P-gp mRNA, zDHHC9 mRNA and SMAD4 mRNA were detected by RT-PCR. Expression of P-gp, zDHHC9 and SMAD4 protein were detected by Western blot. The IC50 of LoVo/L-OHP for L-OHP was (112.5±23.6) μg/mL, and the IC50 decreased to (62.8±21.4) μg/mL (P<0.05) and (58.9±26.3) μg/mL (P<0.05) after the treatment with 0.71 μg/mL AB4 and 0.45 μg/mL Tet (non-toxic dose) separately. The cell cycle experiment showed that the cells in G1 stage decreased and in S stage increased but with no statistical significance (P>0.05). The cell apoptosis experiment showed that the apoptotic rate increased after the treatment with AB4 and Tet with non-toxic dose but with no statistical significance (P>0.05). The RT-PCR experiment showed that the expressions of P-gp mRNA and zDHHC9 mRNA were increased and SMAD4 mRNA was decreased in LoVo/L-OHP cells compared with in LoVo cells (P<0.05), while it was found that P-gp mRNA in LoVo/L-OHP cells was decreased after the treatment with AB4 at non-toxic dose (P<0.05). Western blot experiment showed the protein of P-gp in LoVo/L-OHP cells was decreased after treatment with AB4 (P<0.05), which was accordant to the PCR result. The expression of zDHHC9 protein in LoVo/L-OHP cells was decreased in LoVo/L-OHP cells after treatment with Tet (P<0.05).
CONCLUSIONS:
AB4 and Tet have some reversal effect on resistant to L-OHP in LoVo/L-OHP cells. The molecular mechanism of the resistance reverse effect was related to down-regulation of P-gp for AB4 and down-regulation of zDHHC9 for Tet.

Structure Identification
J Sep Sci. 2011 Feb;34(3):308-16.

Qualitative and quantitative determination of nine main active constituents in Pulsatilla cernua by high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry.[Pubmed: 21268254]


METHODS AND RESULTS:
A novel qualitative and quantitative method using high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) was developed for simultaneous determination of the nine major active constituents in Pulsatilla cernua (Thunb.) Bercht. et Opiz., namely anemoside A3 (1), Anemoside B4 (2), 23-hydroxybetulinic acid (3), cirenshenoside S (4), pulsatilloside B (5), pulsatilloside C (6), oleanolic acid (7), ajugasterone C (8) and β-ecdysterone (9), respectively. A Sapphire C18 column (250 mm × 4.6 mm, 5 μm) and gradient elution were used during the analysis. The identification and quantification of the analytes were achieved on a hybrid quadrupole linear ion trap mass spectrometer. Multiple-reaction monitoring (MRM) scanning was employed for quantification with switching electrospray ion source polarity between positive and negative modes in a single run. All calibration curves showed good linearity (r(2) > 0.9948) within the test ranges. The intra and interday variations for nine analytes were less than 3.95 and 3.78%, respectively. The developed method was successfully applied to determine the investigated compounds in 15 batches of natural and cultured samples of P. cernua.
CONCLUSIONS:
The results indicated that the method was simple, rapid, specific and reliable, which is helpful to comprehensive evaluation of quality of P. cernua.

Anemoside B4 Dilution Calculator

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Preparing Stock Solutions of Anemoside B4

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.8187 mL 4.0937 mL 8.1875 mL 16.3749 mL 20.4687 mL
5 mM 0.1637 mL 0.8187 mL 1.6375 mL 3.275 mL 4.0937 mL
10 mM 0.0819 mL 0.4094 mL 0.8187 mL 1.6375 mL 2.0469 mL
50 mM 0.0164 mL 0.0819 mL 0.1637 mL 0.3275 mL 0.4094 mL
100 mM 0.0082 mL 0.0409 mL 0.0819 mL 0.1637 mL 0.2047 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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Background on Anemoside B4

Anemoside B4 is Pulsatilla koreana Nakai that have many numerous biological effects in vitro, including enhancing hypoglycemic, anti-tumor, neuroprotective and anti-angiogenic activity. AB4 can inhibit the secretion of IL-10; SSA, SSD and PNS up-regulated IL-2 expression.[1] AB4, with IC50 value more than 390 ug/mL. Anemoside B4 inhibits cell proliferation.[2] Anemoside B4 can significantly suppress the secretion of the inflammatory factor E-selectin by endothelial cells. [3]

References:
[1]. Hu Y et al. Role of Chinese herbal medicinal ingredients in secretion of cytokines by PCV2-induced endothelial cells. J Immunotoxicol. 2016;13(2):141-7. [2]. Liu M et al. Cytotoxicity of the compounds isolated from Pulsatilla chinensis saponins and apoptosis induced by 23-hydroxybetulinic acid. Pharm Biol. 2015 Jan;53(1):1-9. [3]. Hu Y et al. Chinese herbal medicinal ingredients inhibit secretion of IL-6, IL-8, E-selectin and TXB2 in LPS-induced rat intestinal microvascular endothelial cells. Immunopharmacol Immunotoxicol. 2009;31(4):550-5.

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References on Anemoside B4

Role of Chinese herbal medicinal ingredients in secretion of cytokines by PCV2-induced endothelial cells.[Pubmed:25721049]

J Immunotoxicol. 2016;13(2):141-7.

While T-lymphocytes are the major cell type responsible for host responses to a virus (including induction of inflammatory responses to aid in ultimate removal of virus), other cells, including macrophages, epithelial and dendritic cells also have key roles. Endothelial cells also play important roles in physiologic/pathologic processes, like inflammation, during viral infections. As endothelial cells can be activated to release various endogenous compounds, including some cytokines, ex vivo measures of cytokine formation by the cells can be used to indirectly assess any potential endothelial dysfunction in situ. The research presented here sought to investigate potential immunolomodulatory effects of five saponins on endothelial cells: Saikosaponins A (SSA) and D (SSD), Panax Notoginseng Saponin (PNS) and Notoginsenoside R1 (SR1) and Anemoside B4 (AB4). For this, cells (porcine iliac artery endothelial line) were challenged with a virus isolate PCV2-AH for 24 h and then treated with the test saponin (at 1, 5 or 10 mug/ml) for an additional 24 h at 37 degrees C. The culture supernatants were then collected and analyzed for interleukin (IL)-2, -4 and -10, as well as interferon (IFN)-gamma by ELISA. The results revealed that PNS and SR1 inhibited the production of IL-4; PNS, SR1 and AB4 inhibited the secretion of IL-10; SSA, SSD and PNS up-regulated IL-2 expression; SSA and SSD increased the level of IFNgamma. All these changes were significant. Taken together, the data suggested these saponins might potentially have a capacity to regulate immune responses in vivo via changes in production of these select cytokines by infected endothelial cells. Nevertheless, the impact of these agents on other key cell types involved in anti-viral responses, including T-lymphocytes, remains to be determined.

Chinese herbal medicinal ingredients inhibit secretion of IL-6, IL-8, E-selectin and TXB2 in LPS-induced rat intestinal microvascular endothelial cells.[Pubmed:19874221]

Immunopharmacol Immunotoxicol. 2009;31(4):550-5.

The aim of the research was to investigate the anti-inflammatory mechanism of Pulsatillae Decoction (PD), the levels of interleukin (IL)-6, IL-8, E-selectin, and thromboxane B(2) (TXB(2)) secreted by cultured rat intestinal microvascular endothelial cells (RIMECs) were determined after treatment with its active ingredients, namely Anemoside B4, anemonin, berberine, jatrorrhizine, palmatine, aesculin, and esculetin. RIMECs were challenged with 1 microg/mL lipopolysaccharide (LPS) for 3 h, and then treated with each of the seven ingredients at three concentrations (1, 5 and 10 microg/mL) for 24 h. The results revealed that anemonin, aesculin and esculetin inhibited the production of IL-6, aesculin and esculetin inhibited the secretion of IL-8, Anemoside B4, berberine and jatrorrhizine downregulated E-selectin expression, anemonin, berberine, jatrorrhizine and palmatine decreased the content of TXB(2). All these changes were significant. Taken together, the data suggest that all seven active ingredients of PD can effectively reduce inflammatory response, thus relieving intestinal dysfunction via multiple pathways.

Qualitative and quantitative determination of nine main active constituents in Pulsatilla cernua by high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry.[Pubmed:21268254]

J Sep Sci. 2011 Feb;34(3):308-16.

A novel qualitative and quantitative method using high-performance liquid chromatography coupled to electrospray ionization tandem mass spectrometry (HPLC-ESI-MS/MS) was developed for simultaneous determination of the nine major active constituents in Pulsatilla cernua (Thunb.) Bercht. et Opiz., namely anemoside A3 (1), Anemoside B4 (2), 23-hydroxybetulinic acid (3), cirenshenoside S (4), pulsatilloside B (5), pulsatilloside C (6), oleanolic acid (7), ajugasterone C (8) and beta-ecdysterone (9), respectively. A Sapphire C18 column (250 mm x 4.6 mm, 5 mum) and gradient elution were used during the analysis. The identification and quantification of the analytes were achieved on a hybrid quadrupole linear ion trap mass spectrometer. Multiple-reaction monitoring (MRM) scanning was employed for quantification with switching electrospray ion source polarity between positive and negative modes in a single run. All calibration curves showed good linearity (r(2) > 0.9948) within the test ranges. The intra and interday variations for nine analytes were less than 3.95 and 3.78%, respectively. The developed method was successfully applied to determine the investigated compounds in 15 batches of natural and cultured samples of P. cernua. The results indicated that the method was simple, rapid, specific and reliable, which is helpful to comprehensive evaluation of quality of P. cernua.

Cytotoxicity of the compounds isolated from Pulsatilla chinensis saponins and apoptosis induced by 23-hydroxybetulinic acid.[Pubmed:25026337]

Pharm Biol. 2015 Jan;53(1):1-9.

CONTEXT: The rizoma of Pulsatilla chinensis (Bunge) Regel has been used as a traditional Chinese medicinal herb for thousands of years. Total saponins from P. chinensis can induce the apoptosis of solid cancer cells; however, their activity on chronic myeloid leukemia and the mechanisms remains unknown. OBJECTIVE: To study the activity of total saponins and the main active fractions from P. chinensis saponins on chronic myeloid leukemia, and to illustrate the mechanisms underlying the anticancer activities. MATERIALS AND METHODS: The cytotoxic activity were assayed by MTT; cell cycle arrest and apoptosis were tested by flow cytometry system; changes in the mitochondrial membrane potential were determined using JC-1; and the apoptosis signaling pathway was determined by western blotting. RESULTS: We demonstrated that total P. chinensis saponin displayed cytotoxic activity against K562 cell line. In addition, we identified 23-hydroxybetulinic acid (HBA), pulchinenoside A (PA), and Anemoside B4 (AB4) from the total saponins, with the most cytotoxic compound HBA. Glycosylation at C3 and C28 of HBA significantly reduces its cytotoxicity. HBA could promote cell cycle arrest at S phase and induce apoptosis via intrinsic pathway. HBA disrupts mitochondrial membrane potential significantly (p < 0.01) and selectively downregulates the levels of Bcl-2, survivin and upregulates Bax, cytochrome C, cleaved caspase-9 and -3. DISCUSSION AND CONCLUSION: Total saponins from P. chinensis may be effective natural products against human chronic myelogenous leukemia; HBA is one of the bioactive components responsible for its anticancer activity, and could be further investigated as an alternative therapeutic drug for leukemia.

Description

Pulchinenoside C (Anemoside B4) is Pulsatilla koreana Nakai that have many numerous biological effects in vitro, including enhancing hypoglycemic, anti-tumor, neuroprotective and anti-angiogenic activity.

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