Artepillin C | CAS:72944-19-5 | Manufacturer ChemFaces

Artepillin C

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Description:

Artepillin C shows antioxidant, anti-angiogenesis, and anti-tumor activities; it also shows anti-inflammatory effects mediated, at least in part, by prostaglandin E2 and nitric oxide inhibition through NF-κB modulation. Artepillin C activates the immune system, and possesses direct antitumor activity. Artepillin C can suppress alloreactive CD4 T cell responses in vitro, so it could be used as a potential immunosuppressant, either solely or as adjunct agent in treating graft versus host disease. Artepillin C promotes adipocyte differentiation and glucose uptake in part by direct binding to PPARγ, which could be the basis of the pharmacological benefits of green propolis intake in reducing the risk of type 2 diabetes.

Targets:

In vitro:

Cancer detection and prevention, 1998,22(6):506-515.

Apoptosis and suppression of tumor growth by artepillin C extracted from Brazilian propolis.[Reference: WebLink]

METHODS AND RESULTS:
Artepillin C was extracted from Brazilian propolis. Artepillin C (3,5-diprenyl-4-hydroxycinnamic acid) has a molecular weight of 300.40 and possesses antibacterial activity. When Artepillin C was applied to human and murine malignant tumor cells in vitro and in vivo, Artepillin C exhibited a cytotoxic effect and the growth of tumor cells was clearly inhibited. The Artepillin C was found to cause significant damage to solid tumor and leukemic cells by the MTT assay, DNA synthesis assay, and morphological observation in vitro. When xenografts of human tumor cells were transplanted into nude mice, the cytotoxic effects of Artepillin C were most noticeable in carcinoma and malignant melanoma. Apoptosis, abortive mitosis, and massive necrosis combined were identified by histological observation after intratumor injection of 500 microg of Artepillin C three times a week. In addition to suppression of tumor growth, there was an increase in the ratio of CD4/CD8 T cells, and in the total number of helper T cells.
CONCLUSIONS:
These findings indicate that Artepillin C activates the immune system, and possesses direct antitumor activity.

Journal of Ethnopharmacology,2011,138(2): 463-471.

Brazilian green propolis and its constituent, Artepillin C inhibits allogeneic activated human CD4 T cells expansion and activation.[Reference: WebLink]

Propolis has long been used as a popular folk medicine by various ethnic groups due to its wide spectrum of alleged biological and pharmaceutical properties including anti-microbial, anti-cancer and anti-inflammatory functions. All these can be linked to the modulation of immune function. Therefore, it will be relevant for us to find out whether there is any novel compound that can account for such action and the mechanism involved. We investigated the immune modulating effect of Brazilian green propolis (PBrazil) and its constituent Artepillin C (Art-C) by using mixed leukocytes reaction.
METHODS AND RESULTS:
The cytotoxic effect of Art-C on non-tumorigenic human liver cell line miHA and non-tumorigenic human kidney cell line HK-2 as well as human peripheral blood mononuclear cells (PBMCs) were measured by XTT cell proliferation assay. The effect of PBrazil and Art-C on T cell proliferation and activation were determined by using carboxyfluorescein succinimidyl ester (CFSE) and by CD25 expression, respectively. Cytokines including tumor necrosis factor-α (TNF-α), interferon-gamma (IFN-γ), interleukins such as IL-2, IL-17 were measured by intracellular cytokine staining and IL-10 was measured by ELISA. The effect of PBrazil and Art-C on regulatory T cells (Treg) induction was determined by the Foxp3 expression. The apoptotic effect of these compounds on CFSE labeled alloreactive T cells was measured by using Annexin V. Using mixed leukocytes reaction we demonstrated for the first time that both Art-C and PBrazil significantly inhibited the alloreactive CD4 T cell proliferation, activation, and suppressed the expressions of IL-2, IFN-γ and IL-17 in these alloreactive CD4 T cells. The inhibitions of Art-C and PBrazil on CD4 T cells were not due to direct cytotoxic effect on PBMC or inducing regulatory T cells differentiation. Both Art-C and PBrazil were found to selectively induce apoptosis in proliferating T cells. The anti-proliferative effect of Art-C and PBrazil were reversible and were also applied to the activated T cells.
CONCLUSIONS:
In conclusion, our results indicated that Art-C and PBrazil can suppress alloreactive CD4 T cell responses in vitro, suggesting that Art-C could be used as a potential immunosuppressant, either solely or as adjunct agent in treating graft versus host disease.

Artepillin C Description

Source:	From Brazilian propolis
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Phytotherapy Research, 2009, 23(3):423-427.

Artepillin C (ARC) in Brazilian green propolis selectively blocks oncogenic PAK1 signaling and suppresses the growth of NF tumors in mice.[Reference: WebLink]

METHODS AND RESULTS:
There are mainly three types of propolis whose major anticancer ingredients are entirely different: (1) CAPE (caffeic acid phenethyl ester)-based propolis in Europe, Far East and New Zealand, (2) Artepillin C (ARC)-based Brazilian green propolis and (3) Brazilian red propolis. It was shown previously that NF (neurofibromatosis)-associated tumors require the kinase PAK1 for their growth, and CAPE-based propolis extracts such as Bio 30 suppress completely the growth of NF tumors in vivo by blocking PAK1 signaling. Also it was demonstrated that ARC suppresses angiogenesis, suggesting the possibility that ARC also blocks oncogenic PAK1 signaling. Here it is shown for the first time that both ARC and green propolis extract (GPE) indeed block the PAK1 signaling selectively, without affecting another kinase known as AKT. Furthermore, it was confirmed that ARC as well as GPE suppress almost completely the growth of human NF tumor xenografts in mice, as does Bio 30.
CONCLUSIONS:
These results suggest that both CAPE-based and ARC-based propolis extracts are natural anti-PAK1 remedies and could be among the first effective NF therapeutics available on the market. Since more than 70% of human cancers such as breast and prostate cancers require the kinase PAK1 for their growth, it is quite possible that GPE could be potentially useful for the treatment of these cancers, as is Bio 30.

Cell Research:

Archives of Biochemistry & Biophysics, 2004, 424(2):0-188.

Antioxidative bioavailability of artepillin C in Brazilian propolis.[Reference: WebLink]

Propolis has strong antioxidative activity.
METHODS AND RESULTS:
We investigated here whether this activity was available in intestinal Caco-2 and hepatic HepG2 cells. Phenolics in Brazilian propolis, extracted with ethyl acetate after the removal of resin and wax with 90% methanol, included Artepillin C at 21 mmol/100 g, p-coumaric acid and cinnamic acid relatives 24 mmol, kaempferol and its derivatives 9.4 mmol, naringenin 2.8 mmol, isosakuranetin 0.9 mmol, chrysin at 0.8 mmol/100 g, and several minor components. When the extract was added to the apical side of Caco-2 monolayers, Artepillin C was specifically incorporated into the cells and released to the basolateral side mostly without conjugation. Then, Artepillin C was added to HepG2 cells and exposed to reactive oxygens. Artepillin C prevented oxidative damage dose-dependently, and suppressed lipid peroxidation evaluated with thiobarbituric acid reactive substances by 16% and the formation of 8-hydroxy-2′-deoxyguanosine in DNA by 36% at a concentration of 20 μM.
CONCLUSIONS:
Artepillin C is a bioavailable antioxidant.

Animal Research:

European Journal of Pharmacology, 2008, 587(1-3):296-301.

Anti-inflammatory effects of a bioavailable compound, Artepillin C, in Brazilian propolis.[Reference: WebLink]

Artepillin C is the major compound in the Brazilian green propolis from Baccharis dracunculifolia. Our aim in this study was to investigate the anti-inflammatory effects, absorption, and bioavailability of Artepillin C in mice.
METHODS AND RESULTS:
The animals used were male Swiss mice subjected to: paw oedema by carrageenan (300 μg/paw), carrageenan-induced peritonitis, and prostaglandin E2 determination. We also measured in vitro nitric oxide production by RAW 264.7 cells and NF-κB activity in HEK 293 cells. Finally, we measured the absorption and bioavailability of Artepillin C in plasma from mice by means of GC-MS after a single oral dose (10 mg/kg). In vivo, Artepillin C produced a maximal inhibition of 38% after 360 min on paw oedema. Artepillin C also decreased the number of neutrophils during peritonitis (IC50: 0.9 (0.5–1.4) mg/kg). Treatment with Artepillin C decreased prostaglandin E2 by 29 ± 3% and 58 ± 5% at 1 and 10 mg/kg, respectively, with a mean ID50 of 8.5 (8.0–8.7)mg/kg). Similarly, in in vitro models, Artepillin C (3, 10, or 100 μM) decreased nitric oxide production by RAW 264.7 cells with a mean IC50 of 8.5 (7.8–9.2) μM. In HEK 293 cells, Artepillin C reduced NF-κB activity with a mean IC50 of 26 (22–30) μg/ml), suggesting anti-inflammatory activity, particularly during acute inflammation. Lastly, Artepillin C was absorbed after an oral dose (10 mg/kg) with maximal peaks found at 1 h (22 μg/ml).
CONCLUSIONS:
Collectively, Artepillin C showed anti-inflammatory effects mediated, at least in part, by prostaglandin E2 and nitric oxide inhibition through NF-κB modulation, and exhibited bioavailability by oral administration.

Product Name	Artepillin C
Price:
CAS No.:	72944-19-5
Catalog No.:	CFN70443
Molecular Formula:	C₁₉H₂₄O₃
Molecular Weight:	300.4 g/mol
Purity:	>=98%
Type of Compound:	Phenols
Physical Desc.:	Powder
Source:	From Brazilian propolis
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Phenols Compound Library TNF-α Inhibitor Library PAK Inhibitor Library IFN-γ Inhibitor Library Antifection Inhibitor Library Akt Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.3289 mL	16.6445 mL	33.2889 mL	66.5779 mL	83.2224 mL
5 mM	0.6658 mL	3.3289 mL	6.6578 mL	13.3156 mL	16.6445 mL
10 mM	0.3329 mL	1.6644 mL	3.3289 mL	6.6578 mL	8.3222 mL
50 mM	0.0666 mL	0.3329 mL	0.6658 mL	1.3316 mL	1.6644 mL
100 mM	0.0333 mL	0.1664 mL	0.3329 mL	0.6658 mL	0.8322 mL

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CFN99339	Meliasenin B	1221262-77-6	468.7	C₃₀H₄₄O₄
CFN98144	Peimisine	19773-24-1	427.62	C₂₇H₄₁NO₃
CFN92965	2,3-Dihydro-3-methoxywithaferin A	21902-96-5	502.64	C₂₉H₄₂O₇