Product name: Lithospermic acid
Synonym name: Lithospermic acid A; Clinopodic acid H
Catalogue No.: BP0878
Cas No.: 28831-65-4
Formula: C₂₇H₂₂O₁₂
Mol Weight: 538.461
Botanical Source: Clinopodium chinense var. parviflorum, Cynoglossum officinale, Cordia spinescens, Lycopus europeus, Salvia miltiorrhiza, Lithospermum ruderale and Lithospermum officinale
Physical Description: Powder
Type of Compound: Phenylpropanoids

Purity: 95%~99%
Analysis Method: HPLC-DAD or/and HPLC-ELSD
Identification Method: Mass, NMR
Packing: Brown vial or HDPE plastic bottle

Storage: Store in a well closed container, protected from air and light. Put into refrigerate or freeze for long term storage.
Whenever 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 -20℃. Generally, these will be useable for up to two weeks.

The product could be supplied from milligrams to grams, up to kilograms
Inquire for bulk scale.

Descriptions:
Lithospermic acid (LSA) was originally isolated from the roots of Salvia mitiorrhiza ,
has antioxidant effects, is a competitive inhibitor of xanthine oxidase (XO), can directly scavenge superoxide and inhibit superoxide production in vitro, and presents hypouricemic and anti-inflammatory actions in vivo.[1]
Lithospermic acid has inhibitory effects on proliferation and migration of rat vascular smooth muscle cells.[2]
Lithospermic acid derivatives from Lithospermum erythrorhizon can increase expression of serine palmitoyltransferase in human HaCaT cells.[3]
Lithospermic acid possesses anti-HIV activity.[4]
Treatment with lithospermic acid B has a preventive effect on the development of diabetic retinopathy in this animal model, probably because of its antioxidative effects and anti-inflammatory effects.[5]
Lithospermic acid can attenuate 1-methyl-4-phenylpyridine-induced neurotoxicity by blocking neuronal apoptotic and neuroinflammatory pathways.[6]
Lithospermic acid has hepatoprotective effects against carbon tetrachloride-induced liver oxidative damage in vitro and in vivo.[7]
Lithospermic acid can attenuate mesenteric ischemia reperfusion injury in rat intestines by increasing tissue SOD and GPx activities and decreasing MDA and MPO levels, also improves morphological alterations which occurred after periods of reperfusion.[8]

References:
[1] Liu X, Chen R, Shang Y, et al. Chem Bioll Interact, 2008, 176(2–3):137-42.
[2] CHEN, Wen-yi, WANG, et al. Acta Pharmacol Sin, 2009, 30(9):1245-52.
[3] Thuong P T, Kang K W, Kim J K, et al. Bioorg Med Chem Lett, 2009, 19(6):1815-7.
[4] Varadaraju T G, Hwu J R. Org Biomol Chem, 2012, 10(28):5456-65.
[5] Jin C J, Yu S H, Wang X M, et al. Plos One, 2014, 9(6):e98232-e98232.
[6] Lin Y L, Tsay H J, Lai T H, et al. J Biomed Sci, 2015, 22(1):1-13.
[7] Chan, Ho. Oncol Rep, 2015,34(2):673-80.
[8] Ozturk H, Terzi E H, Ozgen U, et al. Adv Clin Exp Med, 2012, 21(4):433-9.
[9] Yan L U, Sai-Wei W U, Dan-Hua X U. China j Chinese Materia Medica, 2015, 40(9):1744-6.

HPLC of Lithospermic acid

HNMR of Lithospermic acid

Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃

Introduction/Overview

Lithospermic acid (CAS No.: 28831-65-4) is a polycyclic carboxylic acid compound derived from Salvia miltiorrhiza (Salvia miltiorrhiza). As a traditional Chinese medicinal herb, Salvia miltiorrhen is widely used clinically due to its significant cardiovascular and cerebrovascular protective effects. In recent years, with the deepening of research into the active components of Danshen, purple acid has attracted widespread attention due to its unique chemical structure and multiple biological activities. Numerous in vivo and in vitro experiments have shown that shikonic acid exhibits good pharmacological activity in antioxidant, anti-inflammatory, and hepatoprotective aspects, especially demonstrating significant protective effects in models of acute liver injury induced by carbon tetrachloride (CCl4). Moreover, shichetin exerts its anti-inflammatory effects by regulating various inflammation-related signaling pathways and key molecular targets, providing a theoretical basis for its potential natural drug development.

This paper aims to systematically review the chemical structure and physicochemical properties of shikonic acid, plant origin and extraction methods, pharmacological activity and mechanism of action, druggability evaluation, and pharmacokinetic characteristics. Considering its clinical application prospects, it comprehensively summarizes the research progress of shirtic acid, providing a reference for subsequent basic and clinical studies.

Chemical structure and physicochemical properties

Purthicheic acid is a polycyclic carboxylic acid with a molecular formula of C27H22O12 and a molecular weight of 538.4610. Its structure contains multiple phenolic hydroxyl and carboxyl groups, giving it excellent antioxidant capacity. The LogP value of shicartin is about 2.08, indicating moderate lipid solubility that facilitates cell membrane penetration, but its water solubility is relatively low (0.2089), suggesting limited solubility in the body. Its topological polar surface area (TPSA) is 211.28 Ų, and its higher polar surface area may limit its ability to cross the blood-brain barrier, which aligns with its low blood-brain barrier permeability characteristics.

Shichetin does not show hERG channel inhibitory effects, suggesting a low risk of cardiotoxicity. The Ames-induced mutagenic test result was 0.0, indicating that purthichet acid poses no significant genotoxicity risk. These physicochemical properties and safety indicators lay a solid foundation for the drug development of shichevitic acid.

Plant Origins and Extraction Methods

Shikartic acid is mainly isolated from the roots and rhizomes of Salvia miltiorrhiza. Salvia miltiorrhiza is the dried root of Salvia miltiorrhiza Bunge, a plant in the Lamiaceae family, widely distributed in northern China and the Korean Peninsula. Danshen contains various phenolic acid compounds, among which purple acid is one of the important active components.

Traditional extraction methods mostly use water extraction or ethanol extraction, combined with liquid-liquid separation and column chromatography techniques to purify purified purified puric acid. Modern extraction processes are gradually introducing ultrasound-assisted extraction, microwave-assisted extraction, and high-performance liquid chromatography (HPLC) separation technologies to improve extraction efficiency and purity. The specific steps include:

1. The raw materials are crushed and extracted with 70% ethanol, with extraction time of about 2 hours.
2. After filtration and concentration, the extract is distributed using an ethyl acetate-water system.
3. Further purification is performed by silica gel column chromatography or C18 reversed-phase column chromatography.
4. Finally, purity and structural identification are confirmed by HPLC.

This method can obtain high-purity purple acid, meeting the needs of pharmacological research and formulation development.

Pharmacological activity research

Antioxidant and liver-protective effects

Shithinic acid exhibits significant antioxidant activity, scavenging free radicals and reducing cellular damage caused by oxidative stress. In the CCl4-induced liver injury model, shichetin significantly reduced hepatocyte necrosis and inflammatory responses by lowering malondialdehyde (MDA) levels in liver tissue and increasing the activity of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px), thereby promoting liver tissue repair.

In vitro experiments show that shikartic acid can inhibit CCl4-induced hepatocyte apoptosis, protect hepatocyte mitochondrial function, reduce intracellular ROS production, and maintain intracellular redox balance.

Anti-inflammatory effects

Shichetin exerts broad anti-inflammatory effects by regulating various inflammatory factors and signaling pathways. Its targets involve key inflammatory mediators such as IL-6, TNF-α, STAT3, and NFKB1. Research shows that shirtic acid can inhibit the expression and release of inflammatory factors, reduce inflammatory responses, and improve tissue damage.

Additionally, shichelac acid regulates the inflammation-related ion channels TRPV1 and TRPA1, reducing neuroinflammation and pain responses. Its inhibitory effect on cyclooxygenases PTGS1 and PTGS2 further illustrates the multi-target characteristics of its anti-inflammatory mechanism.

Other pharmacological activities

Shichetin also exhibits certain anti-tumor, antibacterial, and neuroprotective activities. Although related research is still in its early stages, its polyphenol structure gives it broad bioactivity potential.

Mechanism of action and molecular targets

The pharmacological effects of shithilinic acid are mainly realized by regulating oxidative stress and inflammatory signaling pathways. Its mechanisms of action include:

1. Antioxidant mechanism: Shithiacic acid lowers ROS levels and protects cells from oxidative damage by directly scavenging free radicals and activating endogenous antioxidant enzyme systems (such as SOD, GSH-Px).

2. Anti-inflammatory mechanism: Shichetin inhibits the nuclear factor κB (NF-κB) signaling pathway, reduces the expression of pro-inflammatory factors TNF-α and IL-6, blocks STAT3 signaling, and alleviates inflammatory responses. Its regulation of CASP1 (the inflammasome component) helps inhibit the maturation and release of the inflammatory mediator IL-1β.

3. Regulating ion channels: By acting on TRPV1 and TRPA1, purziacin modulates calcium ion influx, relieving neuroinflammation and pain.

4. Inhibition of cyclooxygenase: Inhibits PTGS1 and PTGS2, reduces prostaglandin synthesis, and exerts anti-inflammatory and analgesic effects.

5. Regulating nitric oxide synthase: Inhibits induced nitric oxide synthase (NOS2), reduces excessive NO production, and alleviates inflammation and oxidative damage.

The synergistic effects of these multi-target and multi-pathway mechanisms enable shichetin to show good therapeutic potential across various disease models.

Druggability evaluation and pharmacokinetics

Druggability evaluation of shicyrinic acid indicates it has certain potential for drug development. Its molecular weight of 538.46 is slightly higher than the ideal range for traditional oral drugs, but the LogP value is moderate, indicating that its lipid solubility is suitable for cell membrane penetration. High TPSA values and low blood-brain barrier permeability suggest that it mainly acts on peripheral tissues, reducing the risk of adverse reactions in the central nervous system.

Shirashic acid does not inhibit hERG channels, reducing the risk of cardiotoxicity; Ames test is negative, indicating relatively high safety. Its low water solubility may limit oral bioavailability, requiring formulation optimization or structural modification.

Pharmacokinetic studies show that purchetin is absorbed orally slowly, has limited bioavailability, is mainly metabolized by the liver, and excreted mainly through bile and urine. Its half-life is moderate, making it suitable for routine administration.

Future research on in vivo pharmacokinetics and toxicology systems is needed to clarify metabolic pathways and safe dosage ranges.

Prospects and outlooks for clinical applications

As an important active ingredient in Danshen, purzirtic acid has broad clinical application prospects due to its remarkable antioxidant, anti-inflammatory, and hepatoprotective effects. Its therapeutic potential for liver diseases, especially acute and chronic liver injury and liver fibrosis, is worth further exploration.

Additionally, purthia acid regulates multiple inflammation-related targets, showing potential in treating inflammatory diseases such as arthritis, neuroinflammation, and cardiovascular inflammation. Its low toxicity and good safety profile ensure its clinical translation.

Future research should focus on:

1. Optimizing purchetin drug formulations to improve bioavailability and targeting.
2. In-depth analysis of its molecular mechanisms to expand its indication range.
3. Conduct systematic preclinical and clinical trials to verify efficacy and safety.
4. Exploring the synergistic effects of shichevin with other drugs to develop compound formulations.

Through multidisciplinary collaboration, shirtocic acid is expected to become an important candidate molecule in the development of natural product drugs.

Conclusion

As a polycyclic carboxylic acid derived from Salvia miltiorrhiza, puracetic acid exhibits broad and significant antioxidant, anti-inflammatory, and hepatoprotective activities. Its multi-target mechanism of action and good safety profile provide a solid foundation for its drug development. Although further breakthroughs are still needed in pharmacokinetics and clinical research, purple acid, with its unique biological properties and traditional medicinal value, holds significant potential as a new natural medicine. In the future, through in-depth mechanistic research and clinical validation, purzirtic acid is expected to bring new hope for the treatment of various inflammatory and liver diseases.