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Synonym name: Arteannuin; Qinghaosu; Qing Hau Sau
Catalogue No.: BP0197
Cas No.: 63968-64-9
Formula: C15H22O5
Mol Weight: 282.336
Botanical Source: Artemisia annua (Qinghaosu)
Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle
Can be supplied from milligrams to grams.
For Reference Standard and R&D, Not for Human Use Directly.
Inquire for bulk scale.
HPLC of Artemisinin
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
63.6000
2.2000
2.2000
High
No
Negative
No
Negative
Artemisininin, CAS number 63968-64-9, is a species derived from Artemisia annua L.) is a natural peroxide product within the sesquiterpene extracted from L. Since its discovery in the 1970s by the Chinese scientist Tu Youyou's team, artemisinin has become a milestone in global antimalarial drug research and clinical application due to its remarkable antimalarial activity, especially its effectiveness against multidrug-resistant malaria malaria strains. Artemisinin not only demonstrates outstanding efficacy in the antimalarial field but also exhibits broad biological activities, including antibacterial, antifungal, antitumor, and neuroprotective effects, gradually becoming a hot topic in pharmacological research of natural products.
In recent years, with deeper analysis of the mechanism of action of artemisinin, its potential therapeutic value in metabolic diseases such as steatohepatitis has gradually emerged. This paper systematically reviews the chemical structure and physicochemical properties of artemisinin, plant origin and extraction process, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics, with a focus on exploring its prospects and challenges in clinical application, aiming to provide theoretical support and research direction for further development of artemisinin and its derivatives.
Artemisinin is a typical sesquiterpene peroxide, with a molecular formula of C15H22O5 and a molecular weight of 282.33. Its core structure is connected to the sesquiterpene framework by a unique internal peroxybridge ring (1,2,4-trioxane ring), forming an important basis for its biological activity. This peroxide bridge is a key group for artemisinin's antimalarial activity, capable of generating free radicals in the presence of iron ions and destroying the biomacromolecules of malaria parasite cells.
Artemisinin exhibits moderate lipophilicity and a LogP of about 2.2, indicating good cell membrane permeability. With a polar surface area (TPSA) of 63.6 Ų and 5 hydrogen bond acceptors, it supports its potential to bind to various biological macromolecules. Additionally, artemisinin has high blood-brain barrier permeability, suggesting its potential application value in neurological diseases. Its half-life is about 1 hour, indicating a relatively fast metabolic rate in the body. Toxicological evaluation showed that artemisinin had no significant hepatotoxicity, cardiotoxicity, or hERG channel inhibition; Ames-induced mutagenic test results were negative, indicating relatively high safety.
Artemisia annua mainly comes from the above-ground parts of Artemisia annua L., with higher levels in leaves and tender stems during flowering. Artemisia yellow is a plant of the Asteraceae family, widely distributed in China and other temperate and subtropical regions. Its artemisinin content is significantly influenced by variety, cultivation conditions, harvest time, and processing technology.
Traditional extraction methods include organic solvent extraction, such as ethanol, ethyl acetate, or n-hexane, combined with ultrasonic-assisted extraction or reflux extraction techniques to improve yield. Modern processes are gradually adopting supercritical CO2 extraction, microwave-assisted extraction, and membrane separation technologies, aiming to improve extraction efficiency, reduce harmful solvent residues, and lower production costs. The crude extract after extraction undergoes purification steps such as silica gel column chromatography and reversed-phase high-performance liquid chromatography (RP-HPLC) to obtain high-purity artemisinin.
Moreover, with the development of synthetic biology, the technology of genetically engineered microorganisms fermenting artemisinin precursors (such as artemisinic acid) and converting them into artemisinin through chemical semi-synthesis has gradually matured, providing new avenues for industrial production.
Artemisinin is best known for its pharmacological effect for its potent antimalarial activity. Its target is the hemoglobin metabolic pathway of Plasmodium. The internal peroxy bridge of artemisinin is cleaved by iron ions to produce free radicals that attack proteins and membrane lipids inside malaria parasite cells, leading to cell death. Artemisinin showed significant killing effects against multidrug-resistant strains of Plasmodium falciparum and acted quickly, making it a first-line antimalarial drug recommended by the World Health Organization.
In addition to its antimalarial effects, artemisinin also exhibits certain inhibitory activity against various bacteria and fungi. Research shows that artemisinin can inhibit the growth of Gram-positive and Gram-negative bacteria, and also has inhibitory effects on certain fungi such as the genus Candida. These activities may be related to their induction of oxidative stress and disruption of microbial cell membrane structures.
Artemisinin exhibits inhibitory effects on proliferation, migration, and invasion across various tumor cell lines. Its mechanisms involve inducing apoptosis, blocking the cell cycle, inhibiting angiogenesis, and regulating the tumor microenvironment. Artemisinin can dose-dependently lower pAKT levels, inhibit the PI3K/AKT signaling pathway, and reduce tumor cell viability and metastasis. Additionally, artemisinin can inhibit the proliferation of vascular smooth muscle cells induced by tumor necrosis factor (TNF), demonstrating its potential in anti-tumor and anti-inflammatory effects.
Artemisinin has good blood-brain barrier permeability, and studies have found that it exhibits neuroprotective effects in models of neurodegenerative diseases. Its mechanism of action may involve antioxidant, anti-inflammatory, and regulatory neuronal apoptosis signaling pathways, demonstrating the potential application value of artemisinin in the treatment of neurological diseases.
Recent studies show that artemisinin has regulatory effects on metabolic diseases such as steatohepatitis. By modulating various targets such as PTPN1, NR1H4, ESR1, GPBAR1, TNF, CETP, HMGCR, NR3C1, and NR1H3, it participates in lipid metabolism, inflammatory responses, and insulin signaling pathways, thereby improving liver fat deposition and inflammation.
The biological activity of artemisinin mainly depends on its unique internal peroxy-bridge structure, which cleaves in the presence of iron ions to produce active free radicals, leading to oxidative damage to proteins, lipids, and DNA within target cells. Its mechanism of action can be summarized as follows:
Free radical-mediated cell damage
Artemisinin binds to intracellular free iron, cleaves the internal peroxy bridge to generate free radicals, attacks key biomolecules of malaria parasites and tumor cells, leading to cellular dysfunction and death.
Signal path regulation
Artemisinin can inhibit the PI3K/AKT signaling pathway, reduce pAKT levels, and suppress cell proliferation and migration. It also modulates inflammation-related signaling pathways such as NF-κB and MAPK, reducing inflammatory responses.
Targeting inflammatory factors
Artemisinin inhibits the expression of tumor necrosis factor (TNF) and other pro-inflammatory factors, reducing inflammation-mediated tissue damage, and plays an especially important role in metabolic diseases such as steatohepatitis.
Nuclear receptor regulation
Artemisinin affects various nuclear receptors such as NR1H4 (farnidate X receptor), ESR1 (estrogen receptor α), and NR1H3 (liver X receptor α), regulating lipid metabolism and energy homeostasis.
Immunomodulatory effects
By regulating immune cell function, artemisinin can enhance the body's immune response, promote pathogen clearance, and promote tumor immune surveillance.
The druggability parameters of artemisinin indicate that it has promising potential for drug development. With a molecular weight of 282.33, moderate lipophilicity (LogP 2.2) and polar surface area (TPSA 63.6) facilitate cell membrane penetration and oral absorption. It has 5 hydrogen bond receptors, which complies with Lipinski's rule and facilitates binding to target proteins.
Artemisinin has high blood-brain barrier permeability, supporting its application in central nervous system diseases. Its in vivo half-life is about 1 hour, indicating the need for formulation optimization or derivative modification to extend the duration of action. In terms of safety, artemisinin has no hepatotoxicity, cardiotoxicity, or hERG channel inhibition, and the Ames test is negative, indicating low toxicological risk.
Pharmacokinetic studies show that artemisinin is rapidly absorbed orally but its bioavailability is limited by its poor water solubility and hepatic first-pass effect. To improve its pharmacokinetic properties, researchers have developed various delivery systems, such as liposomes, nanoparticles, and solid dispersions, to enhance stability and bioavailability.
Artemisinin, as an antimalarial drug, has been widely used clinically, especially playing a key role in combating resistant malaria falciparum strains. Its rapid onset, low toxicity, and good tolerability make it the preferred drug recommended by the World Health Organization. In the future, as malaria prevention and control strategies continue to improve, artemisinin combination therapy will remain central to controlling malaria epidemics.
In the field of anti-tumors, artemisinin and its derivatives demonstrate broad anti-cancer potential, especially in solid tumors such as lung cancer, breast cancer, and colorectal cancer, which exhibit the ability to inhibit tumor growth and metastasis. Preclinical research is deepening and is expected to enter clinical trial stages in the future, becoming an important representative of natural anti-cancer drugs.
In addition, the potential applications of artemisinin in neuroprotective and metabolic diseases such as steatohepatitis have also attracted significant attention. Its multi-target and multi-mechanism pharmacological properties offer new ideas for treating complex diseases. Through structural modification and improvements in drug carrier technology, artemisinin's efficacy and safety are expected to be further enhanced.
However, the clinical promotion of artemisinin still faces some challenges, such as poor drug stability, low bioavailability, and risks of drug resistance. Future research should focus on optimizing the medicinal chemistry of artemisinin, deeply analyzing its mechanism of action, and validating new indications clinically to promote its multi-field clinical application.
Artemisinin, a unique natural product of peroxide within sesquiterpenes, has become a classic representative in the field of natural product pharmacology due to its outstanding antimalarial activity and diverse pharmacological effects. Its unique chemical structure endows it with rich biological activity, covering antimalarial, antibacterial, antitumor, neuroprotection, and metabolic regulation. Druggability evaluations indicate that artemisinin has good drug development potential and relatively high safety.
In the future, with continuous advances in modern drug development technology, artemisinin and its derivatives are expected to play important roles in more disease fields. In-depth analysis of its mechanism of action, optimization of pharmacokinetic properties, and systematic clinical research will lay a solid foundation for the widespread application of artemisinin. Artemisinin is not only a model of modernization in traditional Chinese medicine but also a valuable resource for innovation in natural product drugs, worthy of ongoing attention and in-depth development.
Shenshuai
Wenjing
Hedandan
