Artemisinic acid | CAS:80286-58-4 | Manufacturer ChemFaces

Artemisinic acid

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Description:

Artemisinic acid, is the immediate precursor of the semi-synthesis artemisinin, could be a cost-effective, environmentally friendly, high-quality and reliable source of artemisinin. Artemisinic acid has a variety of pharmacological activity, such as antimalarial, anti-tumor, antipyretic, antibacterial, allelopathy and anti-adipogenesis effects. Artemisinic acid is a regulator of adipocyte differentiation and C/EBP δ expression, it inhibits adipogenic differentiation of hAMSCs through reduced expression of C/EBP δ; it inhibits melanogenesis through downregulation of C/EBP α-dependent expression of HMG-CoA reductase gene.

Targets:

In vitro:

J Cell Biochem. 2012 Jul;113(7):2488-99.

Artemisinic acid is a regulator of adipocyte differentiation and C/EBP δ expression.[Pubmed: 22396222]

Adipocyte dysfunction is associated with the development of obesity. In this study, Artemisinic acid, which was isolated from Artemisia annua L., inhibited adipogenic differentiation of human adipose tissue-derived mesenchymal stem cells (hAMSCs) and its mechanism of action was determined.
METHODS AND RESULTS:
The mRNA levels of peroxidase proliferation-activated receptor (PPAR) γ and CCAAT/enhancer binding protein (C/EBP) α, late adipogenic factors, were reduced by Artemisinic acid. Moreover, the mRNA levels of the PPAR γ target genes lipoprotein lipase, CD36, adipocyte protein, and liver X receptor were down-regulated by Artemisinic acid. Artemisinic acid reduced expression of the C/EBP δ gene without impacting C/EBP β. In addition, attempts to elucidate a possible mechanism underlying the Artemisinic acid-mediated effects revealed that reduced expression of the C/EBP δ gene was mediated by inhibiting Jun N-terminal kinase (JNK). Additionally, Artemisinic acid also reduced the expression of the adipogenesis-associated genes glucose transporter-4 and vascular endothelial growth factor. In addition to the interference of Artemisinic acid with adipogenesis, Artemisinic acid significantly attenuated tumor necrosis factor-α-induced secretion of interleukin-6 by undifferentiated hAMSCs, thus influencing insulin resistance and the inflammatory state characterizing obesity.
CONCLUSIONS:
Taken together, these findings indicate that inhibiting adipogenic differentiation of hAMSCs by Artemisinic acid occurs primarily through reduced expression of C/EBP δ, which is mediated by the inhibition of JNK and suggest that aremisinic acid may be used as a complementary treatment option for obesity associated with metabolic syndrome.

Current Science, 2000 , 78 (6) :709-713.

Antimicrobial activity of artemisinin and its precursors.[Reference: WebLink]

Artemisinic acid and Arteannuin B are biogenetic precursors of Artemisinin, an important antimalarial produced by the herb Artemisia annua. These compounds have been screened for antimicrobial activity against a range of organisms.
CONCLUSIONS:
All the three compounds are active against different bacteria and certain fungal species

Artemisinic acid Description

Source:	The herbs of Artemisia annua L.
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:

Food Chem Toxicol. 2013 Jan;51:225-30.

Artemisinic acid inhibits melanogenesis through downregulation of C/EBP α-dependent expression of HMG-CoA reductase gene.[Pubmed: 23063590]

Cholesterol is associated with the regulation of melanogenesis which is the major physiological defense against solar irradiation. The present study was designed to determine the effects of Artemisinic acid on melanogenesis and its mechanisms of action in human epidermal melanocytes.
METHODS AND RESULTS:
In this study, we found that Artemisinic acid inhibited melanin content. The mRNA levels of microphthalmia-associated transcription factor (MITF) and its downstream genes tyrosinase, tyrosinase-related protein (TRP)-1, and TRP-2 were reduced by Artemisinic acid treatment. Additionally, the mRNA levels of melanogenesis-related genes (c-KIT, stem cell factor (SCF), and macrophage migration inhibitory factor (MIF)) were down-regulated by Artemisinic acid. Furthermore, cAMP production and protein kinase A (PKA) activity were suppressed by Artemisinic acid. Moreover, attempts to elucidate a possible mechanism underlying the Artemisinic acid-mediated effects revealed that Artemisinic acid regulated melanogenesis by inhibiting cholesterol synthesis through downregulation of the hydroxymethylglutaryl CoA (HMG CoA) reductase gene, which was mediated through reduced expression of the CCAAT/enhancer-binding protein (C/EBP) α gene.
CONCLUSIONS:
Taken together, these findings indicate that the inhibition of melanogenesis by Artemisinic acid occurs through reduced expression of the HMG CoA reductase gene, which is mediated by C/EBP α inhibition and suggest that Artemisinic acid may be useful as a hyperpigmentation inhibitor.

Structure Identification:

Nature. 2006 Apr 13;440(7086):940-3.

Production of the antimalarial drug precursor artemisinic acid in engineered yeast.[Pubmed: 16612385 ]

Malaria is a global health problem that threatens 300-500 million people and kills more than one million people annually. Disease control is hampered by the occurrence of multi-drug-resistant strains of the malaria parasite Plasmodium falciparum. Synthetic antimalarial drugs and malarial vaccines are currently being developed, but their efficacy against malaria awaits rigorous clinical testing. Artemisinin, a sesquiterpene lactone endoperoxide extracted from Artemisia annua L (family Asteraceae; commonly known as sweet wormwood), is highly effective against multi-drug-resistant Plasmodium spp., but is in short supply and unaffordable to most malaria sufferers. Although total synthesis of artemisinin is difficult and costly, the semi-synthesis of artemisinin or any derivative from microbially sourced Artemisinic acid, its immediate precursor, could be a cost-effective, environmentally friendly, high-quality and reliable source of artemisinin.
METHODS AND RESULTS:
Here we report the engineering of Saccharomyces cerevisiae to produce high titres (up to 100 mg l(-1)) of Artemisinic acid using an engineered mevalonate pathway, amorphadiene synthase, and a novel cytochrome P450 monooxygenase (CYP71AV1) from A. annua that performs a three-step oxidation of amorpha-4,11-diene to Artemisinic acid. The synthesized Artemisinic acid is transported out and retained on the outside of the engineered yeast, meaning that a simple and inexpensive purification process can be used to obtain the desired product.
CONCLUSIONS:
Although the engineered yeast is already capable of producing Artemisinic acid at a significantly higher specific productivity than A. annua, yield optimization and industrial scale-up will be required to raise Artemisinic acid production to a level high enough to reduce artemisinin combination therapies to significantly below their current prices.

CAS No.	80286-58-4	Price	$80 / 20mg
Catalog No.	CFN97276	Purity	>=98%
Molecular Weight	234.3	Type of Compound	Sesquiterpenoids
Formula	C₁₅H₂₂O₂	Physical Description	Powder
Download	Manual COA MSDS SDF	Similar structural	Comparison (Web) (SDF)

Product Name	Artemisinic acid
CAS No.:	80286-58-4
Catalog No.:	CFN97276
Molecular Formula:	C₁₅H₂₂O₂
Molecular Weight:	234.3 g/mol
Purity:	>=98%
Type of Compound:	Sesquiterpenoids
Physical Desc.:	Powder
Targets:	Tyrosinase \| cAMP \| PKA \| HMG-CoA Reductase \| PPAR \| JNK \| VEGFR \| P450 (e.g. CYP17) \| Antifection \| C/EBP 未
Source:	The herbs of Artemisia annua L.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price:	$80 / 20mg

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Antimalaric Compound Library Sesquiterpenoids Compound Library VEGFR Inhibitor Library Tyrosinase Inhibitor Library PPAR Inhibitor Library PKA Inhibitor Library P450 (e.g. CYP17) Inhibitor Library JNK Inhibitor Library HMG-CoA Reductase Inhibitor Library cAMP Inhibitor Library Antifection Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	4.268 mL	21.3402 mL	42.6803 mL	85.3606 mL	106.7008 mL
5 mM	0.8536 mL	4.268 mL	8.5361 mL	17.0721 mL	21.3402 mL
10 mM	0.4268 mL	2.134 mL	4.268 mL	8.5361 mL	10.6701 mL
50 mM	0.0854 mL	0.4268 mL	0.8536 mL	1.7072 mL	2.134 mL
100 mM	0.0427 mL	0.2134 mL	0.4268 mL	0.8536 mL	1.067 mL

CFN97486	4,5-Epoxyartemisinic acid	92466-31-4	250.3	C₁₅H₂₂O₃
CFN98613	alpha-Epoxydihydroartemisinic acid	380487-65-0	252.4	C₁₅H₂₄O₃
CFN96782	Alpiniaterpene A	1448667-05-7	278.34	C₁₆H₂₂O₄
CFN99430	4,5-Dioxo-4,5-seco-11(13)-cadinen-12-oic acid	137288-61-0	266.3	C₁₅H₂₂O₄
CFN97308	Arteannuin A	82442-48-6	206.3	C₁₃H₁₈O₂
CFN98044	Arteannuin M	207446-90-0	268.4	C₁₅H₂₄O₄
CFN98043	Arteannuin L	207446-89-7	250.3	C₁₅H₂₂O₃
CFN98807	Arteannuin B	50906-56-4	248.3	C₁₅H₂₀O₃
CFN89154	8alpha-Methacryloyloxy-13-ethoxyvernojalcanolide	142891-14-3	510.53	C₂₅H₃₄O₁₁
CFN89143	10beta-Hydroxycadina-4,11(13)-dien-12,8beta-olide	35001-23-1	248.32	C₁₅H₂₀O₃