Artemisinic Acid
(Synonyms: 青蒿酸; Qing Hao acid; Artemisinic acid; Arteannuic acid) 目录号 : GC41610
A sesquiterpene
Cas No.:80286-58-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Artemisinic acid is a sesquiterpene that has been isolated from A. annua. It has been used in the synthesis of the antimalarial agent artemisinin . Artemisinic acid (50-400 µM) decreases triglyceride levels and glycerol-3-phosphate dehydrogenase (GPDH) activity in human adipose tissue-derived mesenchymal stem cells (hAMSCs) in a dose-dependent manner and inhibits adipocyte differentiation when used at a concentration of 200 µM. It reduces mRNA expression and protein levels of C/EBPα, C/EBPδ, and PPARγ as well as the ratio of phosphorylated JNK to JNK in hAMSCs. Artemisinic acid also decreases C/EBPα and HMG-CoA reductase mRNA expression and inhibits cholesterol synthesis and melanogenesis in human epidermal melanocytes.
| Cas No. | 80286-58-4 | SDF | |
| 别名 | 青蒿酸; Qing Hao acid; Artemisinic acid; Arteannuic acid | ||
| Canonical SMILES | CC1=C[C@@]2([H])[C@](CC1)([H])[C@H](C)CC[C@H]2C(C(O)=O)=C | ||
| 分子式 | C15H22O2 | 分子量 | 234.3 |
| 溶解度 | DMF: 20 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 10 mg/ml,Ethanol: 16 mg/ml | 储存条件 | Store at -20°C, stored under nitrogen |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.268 mL | 21.3402 mL | 42.6803 mL |
| 5 mM | 0.8536 mL | 4.268 mL | 8.5361 mL |
| 10 mM | 0.4268 mL | 2.134 mL | 4.268 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Production of the antimalarial drug precursor Artemisinic Acid in engineered yeast
Nature 2006 Apr 13;440(7086):940-3.PMID:16612385DOI:10.1038/nature04640.
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. 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. 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.
Heterologous biosynthesis of Artemisinic Acid in Saccharomyces cerevisiae
J Appl Microbiol 2016 Jun;120(6):1466-78.PMID:26743771DOI:10.1111/jam.13044.
Artemisinic Acid is a precursor of antimalarial compound artemisinin. The titre of biosynthesis of Artemisinic Acid using Saccharomyces cerevisiae platform has been achieved up to 25 g l(-1) ; however, the performance of platform cells is still industrial unsatisfied. Many strategies have been proposed to improve the titre of Artemisinic Acid. The traditional strategies mainly focused on partial target sites, simple up-regulation key genes or repression competing pathways in the total synthesis route. However, this may result in unbalance of carbon fluxes and dysfunction of metabolism. In this review, the recent advances on the promising methods in silico and in vivo for biosynthesis of Artemisinic Acid have been discussed. The bioinformatics and omics techniques have brought a great prospect for improving production of artemisinin and other pharmacal compounds in heterologous platform.
Artemisinic Acid attenuated symptoms of substance P-induced chronic urticaria in a mice model and mast cell degranulation via Lyn/PLC-p38 signal pathway
Int Immunopharmacol 2022 Dec;113(Pt B):109437.PMID:36403523DOI:10.1016/j.intimp.2022.109437.
Background: Chronic urticaria (CU) is a common skin disease that affects about 1% of the world's population of all ages and seriously affects patients' quality of life. Therefore, further safe and effective treatments are urgently needed. Therefore, Artemisinic Acid was investigated in the present study due to its pharmacologic effect on inhibiting mast cell degranulation and chronic urticaria in a mouse model. Results: 4Artemisinic acid decreased the symptoms of substance P-induced chronic urticaria in the mouse model and alleviated secretagogue-induced local cutaneous and systemic anaphylaxis through the Lyn-PLC-p38-NF-κB signaling pathway. Artemisinic Acid inhibited mast cell degranulation and pro-inflammatory cytokine production in vitro. Mechanism analysis demonstrated that it could arrest mast cell activation through the Lyn-PLC-p38/ERK1/2/AKT-NF-κB signaling pathway. Based on the results of in vitro kinase assay of Lyn and PLC, Artemisinic Acid was a potential small molecule inhibitor of Lyn. Artemisinic Acid displayed good structural affinity (KD = 2.64 × 10-6) with Lyn SPR results. Conclusion: Artemisinic Acid can attenuate substance P/MRGPRX2-mediated chronic urticaria and mast cell activation. Artemisinic Acid is an antagonist of Lyn kinase and can be developed as a drug candidate to treat allergic diseases.
Synthesis of Artemisinic Acid derived glycoconjugates and their anticancer studies
Org Biomol Chem 2020 Mar 25;18(12):2252-2263.PMID:32149317DOI:10.1039/d0ob00216j.
Glycoconjugates, due to their diverse functions, are widely regarded as biologically important molecules. Artemisinic Acid 1 occurs naturally in the plant Artemisia annua and is considered to be the biogenetic precursor of the antimalarial drug, artemisinin 2. We report herein the design and synthesis of diverse Artemisinic Acid derived glycoconjugates. We have synthesized 12-O-artemisinic acid-glycoconjugates (7a-k) and 12-N-artemisinic acid-glycoconjugates (8a-k) by utilizing Cu(i)-catalyzed azide-alkyne cycloaddition reactions (Click chemistry) with various synthesized sugar azides (6a-k) in good to excellent yields along with two fluorescently labeled compounds, 12-O-artemisinic acid-glycoconjugate 11 and 12-N-artemisinic acid-glycoconjugate 12, to investigate the mode of action of these compounds in biological systems. All the synthesized Artemisinic Acid glycoconjugates were assayed for their efficacy against the MCF7 cell line. Our anticancer studies indicated that all the synthesized compounds inhibited the growth of MCF7 cells in a dose dependent manner, barring compounds 4 and 7d. However, these compounds exhibit moderate cytotoxicity, as is evident from their IC50 values.
[URA3 affects Artemisinic Acid production by an engineered Saccharomyces cerevisiae in pilot-scale fermentation]
Sheng Wu Gong Cheng Xue Bao 2022 Feb 25;38(2):737-748.PMID:35234394DOI:10.13345/j.cjb.210297.
CRISPR/Cas9 has been widely used in engineering Saccharomyces cerevisiae for gene insertion, replacement and deletion due to its simplicity and high efficiency. The selectable markers of CRISPR/Cas9 systems are particularly useful for genome editing and Cas9-plasmids removing in yeast. In our previous research, GAL80 gene has been deleted by the plasmid pML104-mediated CRISPR/Cas9 system in an engineered yeast, in order to eliminate the requirement of galactose supplementation for induction. The maximum Artemisinic Acid production by engineered S. cerevisiae 1211-2 (740 mg/L) was comparable to that of the parental strain 1211 without galactose induction. Unfortunately, S. cerevisiae 1211-2 was inefficient in the utilization of the carbon source ethanol in the subsequent 50 L pilot fermentation experiment. The Artemisinic Acid yield in the engineered S. cerevisiae 1211-2 was only 20%-25% compared with that of S. cerevisiae 1211. The mutation of the selection marker URA3 was supposed to affect the growth and Artemisinic Acid production. A ura3 mutant was successfully restored by a recombinant plasmid pML104-KanMx4-u along with a 90 bp donor DNA, resulting in S. cerevisiae 1211-3. This mutant could grow normally in a fed-batch fermentor with mixed glucose and ethanol feeding, and the final Artemisinic Acid yield (> 20 g/L) was comparable to that of the parental strain S. cerevisiae 1211. In this study, an engineered yeast strain producing Artemisinic Acid without galactose induction was obtained. More importantly, it was the first report showing that the auxotrophic marker URA3 significantly affected Artemisinic Acid production in a pilot-scale fermentation with ethanol feeding, which provides a reference for the production of other natural products in yeast chassis.