| Catalog No | Package | Original Price | Price | Inventory | Quantity | Operating |
|---|---|---|---|---|---|---|
| BP1488-5mg | 5mg | $420.00 | Sign in |
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Synonym name: Dihydroechinofuran
Catalogue No.: BP1488
Cas No.: 85022-66-8
Formula: C18H20O5
Mol Weight: 316.353
Botanical Source: Lithospermum erythrorhizon roots
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. Inquire for bulk scale.
For Reference Standard and R&D, Not for Human Use Directly.
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
79.9000
3.7790
3.7736
.1411
3.0056
6.8351
Low
89.8515
3.4103
No
Yes
No
No
No
Yes
0.0
Yes
Yes
Yes
Yes
Natural products, as an important source of drug discovery, play an irreplaceable role in the history of human disease treatment. Among them, purple grass（Lithospermum erythrorhizon Sieb. et Zucc., as a traditional medicinal plant, has long been used in the traditional medical systems of Asia, especially in China, Japan, and South Korea, to treat diseases such as inflammation, burns, eczema, and skin infections. Its significant pharmacological activity is mainly attributed to a series of naphthoquinone pigments rich in the roots, such as purpurin and its derivatives. In recent years, with the advancement of separation and identification technology, novel structures and unique activities of compounds have been continuously discovered from purple grass, providing rich chemical entities for modern drug development. Shikonofuran A is one of the natural naphthoquinones with a unique furan ring structure, and its CAS number is 85022-66-8. Preliminary studies have shown that the compound exhibits potential activities in anti-inflammatory and anti proliferative aspects, especially in the target network related to chronic inflammatory skin diseases such as psoriasis, showing the possibility of multi-target effects. Psoriasis is a common skin disease characterized by excessive proliferation, abnormal differentiation, and immune inflammatory infiltration of keratinocytes. Its pathogenesis is complex and involves multiple signaling pathways. Although there are many clinical treatment drugs currently available, long-term use often accompanies side effects or insufficient efficacy. Therefore, the development of new, efficient, and multi-target therapeutic drugs is of great clinical significance. This article aims to systematically review the chemical structure, plant origin, pharmacological activity, mechanism of action, pharmacological properties, and application prospects of purple grass furan A in diseases such as psoriasis, in order to provide comprehensive scientific references for the in-depth research and development of this compound.
Zicao furan A is a natural naphthoquinone derived from purple grass roots. Its chemical structure is based on the 1,4-naphthoquinone parent nucleus and is connected to a characteristic furan ring structural unit on the side chain. This structural feature distinguishes it from common linear alkyl side chain shikonin derivatives (such as acetyl shikonin, β, β - dimethylacryloyl shikonin, etc.), endowing it with unique spatial conformation and physicochemical properties.
According to its pharmacological parameters, the molecular weight of purple grass furan A is 316.3530 g/mol, belonging to the category of small molecule compounds. The calculated lipid water partition coefficient (LogP) is 3.7790, indicating that the compound has moderate lipophilic properties, which is consistent with the hydrophobicity of its naphthoquinone parent nucleus and furan ring. A moderate LogP value usually indicates good membrane permeability, which is beneficial for the absorption of compounds and cellular uptake. The topologically polar surface area (TPSA) is 79.9000 Å ², which is relatively moderate and reflects the presence of a certain number of hydrogen bond acceptors (such as quinone oxygen and furan epoxy atoms) in the molecule, but has not reached a level that severely impedes membrane permeability. The predicted water solubility value is relatively low, about 0.1411 mg/mL, which is consistent with its lipophilic characteristics, suggesting that solubilization strategies may need to be considered in formulation development, such as using cyclodextrin inclusion, nano formulations, or prodrug modifications.
In the preliminary safety screening of the drug, purple grass furan A showed low blood-brain barrier (BBB) permeability, which means it is not easily able to enter the central nervous system. For drugs that mainly act on the peripheral system (such as the skin), this may help reduce the potential risk of central nervous system side effects. In addition, the key cardiac safety indicator - hERG potassium channel inhibition predicted as' no ', indicating a lower risk of inducing QT interval prolongation in the heart. The Ames test predicted a value of 0.0, indicating that it may not have a direct genetic toxicity risk in this model system. These preliminary in vitro prediction data provide a favorable safety starting point for the further development of purple grass furan A, but further confirmation through subsequent experiments is still needed.
Zicao furan A is specifically derived from the Zicao family plant Zicao（Lithospermum erythrorhizon Dry roots of Sieb. et Zucc. Zicao is mainly distributed in China, Japan, South Korea and other places, and its roots are famous for being rich in purple red naphthoquinone pigments. These pigment components are the material basis for the pharmacological activity of purple grass, and their biosynthetic pathways involve phenylpropane metabolism and the construction of naphthoquinone rings.
The extraction and separation of purple grass furan A from plant materials usually follow the conventional process of natural product chemistry. Firstly, grind the dried purple grass roots and extract them using organic solvents. Common extraction solvents include methanol, ethanol, ethyl acetate, or mixed solvents of different proportions, which can effectively dissolve lipophilic naphthoquinone components. Ultrasound assisted extraction or heat reflux extraction are often used to improve extraction efficiency.
After obtaining the crude extract, it needs to undergo a series of chromatographic separation steps for purification. Preliminary separation is often carried out using silica gel column chromatography, with gradient elution systems such as petroleum ether ethyl acetate or chloroform methanol, and grouping based on the polarity of the compounds. Due to the high structural similarity of purple grass furan A and its analogues, further purification often requires more sophisticated chromatographic techniques, such as reverse phase high performance liquid chromatography (RP-HPLC, using C18 column with methanol water or acetonitrile water as mobile phase), preparative thin layer chromatography (PTLC), or medium pressure liquid chromatography (MPLC). By using spectroscopic techniques such as nuclear magnetic resonance (NMR, including 1H NMR, 13C NMR, 2D NMR), mass spectrometry (MS), and ultraviolet visible spectroscopy (UV Vis), and comparing with literature data, the chemical structure of purple grass furan A was finally determined. It is worth noting that the content of purple grass furan A in plants is usually low and belongs to trace components, so its isolation and purification process is somewhat challenging, and the yield is a factor limiting its large-scale acquisition for in-depth biological research. Modern biotechnology, such as plant cell culture, may provide alternative pathways for sustainable and large-scale production of such high-value naphthoquinone compounds.
Although there are relatively limited direct and systematic pharmacological research reports on purple grass furan A, extensive studies on its structural parent nucleus (naphthoquinone) and extracts and similar compounds from purple grass plants can infer and preliminarily summarize its potential pharmacological activity directions. Existing data suggests that the core pharmacological activities of purple grass furan A may focus on anti-inflammatory and anti proliferative aspects, which are highly correlated with the pathological processes of inflammatory and proliferative diseases such as psoriasis.
anti-inflammatory activity Naphthoquinone compounds generally have significant anti-inflammatory effects. Shikonin and its derivatives have been shown to inhibit the production of nitric oxide (NO), prostaglandin E2 (PGE2), and various pro-inflammatory cytokines (such as TNF - α, IL-1 β, IL-6) in macrophages induced by lipopolysaccharide (LPS). Zicao furan A, as a structurally similar derivative, is likely to exert anti-inflammatory effects through similar mechanisms. Overactivation of pro-inflammatory factors (such as TNF - α) and inflammatory signaling pathways (such as NF - κ B, STAT3) is a key feature in psoriatic lesions. Therefore, the anti-inflammatory potential of purple grass furan A is an important basis for its treatment of inflammatory diseases such as psoriasis.
Anti proliferative and pro differentiation activity One of the core pathological changes in psoriasis is the excessive proliferation and incomplete differentiation of epidermal keratinocytes. Multiple studies have shown that purpurin can inhibit the proliferation of various tumor cells and keratinocytes, and induce their differentiation or apoptosis. Zicao furan A may inherit this characteristic by interfering with cell cycle progression or inducing cell cycle arrest, thereby inhibiting abnormal proliferation of keratinocytes. This has direct therapeutic significance for alleviating the thickening of psoriasis plaques (spinous thickening).
antioxidant activity The structure of naphthoquinone itself has redox properties, and many derivatives of purple grass exhibit the ability to scavenge free radicals and resist oxidative stress. Oxidative stress also plays a role in promoting the pathogenesis of psoriasis. Therefore, the potential antioxidant activity of purple grass furan A may help alleviate oxidative damage to skin tissue, assist in anti-inflammatory and anti proliferative effects.
Antibacterial and immune regulatory activity Zicao is traditionally used to treat infectious skin diseases, and its extracts have inhibitory effects on various bacteria and fungi. Although the antibacterial spectrum of purple grass furan A remains to be clarified, this characteristic may be beneficial for preventing or treating secondary infections in psoriasis lesions. In addition, its regulatory effect on the function of immune cells (such as T cells and dendritic cells) is also worth exploring, as psoriasis is essentially a T cell-mediated autoimmune inflammatory disease.
Based on the provided target information related to psoriasis (AMPK, RARA/RARG, STAT3, PRKCA, TRPV1, RELA, TOP2A, MAPK1, TNF), a potential multi-target action network hypothesis of purple grass furan A can be constructed. These targets are widely involved in processes such as inflammatory response, cell proliferation, differentiation, apoptosis, and immune regulation.
Regulating inflammatory signaling pathways：
Regulating cellular metabolism and energy homeostasis：
Affects nuclear receptors and transcriptional regulation：
Intervention of ion channels and kinases：
Targeting key inflammatory factors：
In summary, purple grass furan A may form a synergistic network pharmacology effect by simultaneously acting on multiple key targets such as AMPK, STAT3, NF - κ B, RAR, etc., intervening in the complex pathological process of psoriasis from multiple aspects such as inhibiting inflammation, regulating immunity, blocking cell cycle, inducing normal differentiation, and relieving itching. This multi-target characteristic may be its therapeutic advantage, but it also requires verification and in-depth research through biochemical and cellular biology methods such as molecular docking, surface plasmon resonance (SPR), reporter gene experiments, kinase activity assays, etc.
Based on the physical and chemical properties and preliminary predicted data mentioned earlier, Zicao Furan A shows certain potential as a drug, but there are also challenges that need to be optimized.
Advantage aspects Moderate molecular weight, meeting the basic requirements of the Rule of Five, conducive to oral absorption. Moderate LogP and TPSA values suggest good membrane permeability, which is beneficial for cross cellular transport and bioavailability. The preliminary safety warning (hERG inhibition negative, Ames test negative) provides a relatively positive signal for its subsequent development. Low blood-brain barrier permeability may reduce the risk of central nervous system side effects for drugs primarily used to treat peripheral diseases such as skin.
Challenges and areas to be researched：
1. Solubility and permeability Low water solubility (0.1411 mg/mL) is the main obstacle to its oral administration, which may lead to limited absorption rate and poor bioavailability. Improvements need to be made through pharmaceutical methods.
2. Pharmacokinetic (PK) characteristics unknown At present, there is a lack of systematic PK data on purple grass furan A in vivo, including:
* absorb The degree and rate of absorption in the gastrointestinal tract after oral administration.
* distribution The distribution characteristics of tissues in the body, especially whether they can be effectively delivered to target skin tissues.
* Metabolism The naphthoquinone and furan structures may be susceptible to metabolism by the liver cytochrome P450 (CYP) enzyme system, and it is necessary to clarify their main metabolic enzymes, metabolites, and activities.
* excretion Main excretion pathways (bile, urine) and half-life.
3. Stability Naphthoquinone compounds may be sensitive to light, heat, and oxygen, and stability issues need to be considered during the production and storage of formulations.
4. Potential toxicity Although Ames predicted negative, naphthoquinone compounds may cause cellular or organ toxicity due to the production of reactive oxygen species (ROS) in the redox cycle at high concentrations or long-term use, requiring systematic preclinical toxicological evaluation.
Improvement strategy：
* Formulation strategy Develop new delivery systems such as nanocrystals, liposomes, microemulsions, solid dispersions, or cyclodextrin inclusion complexes to significantly improve their solubility and dissolution rate. For psoriasis, local topical preparations (such as cream, gel, nano lipid carrier) are direct and safe routes of administration, which can bypass the first pass effect and increase the local drug concentration.
* Structural modification By synthesizing derivatives and introducing hydrophilic or prodrug groups while retaining the pharmacophore, their water solubility and PK properties can be improved.
* Preclinical PK/PD study It is necessary to conduct systematic pharmacokinetic studies in animal models (such as mice and rats) as soon as possible, and establish a pharmacokinetic pharmacodynamic (PK-PD) correlation model to provide a basis for drug administration design.
As a natural small molecule with multi-target potential, the clinical application prospects of purple grass furan A mainly revolve around chronic inflammatory/proliferative skin diseases such as psoriasis, but may also be expanded to other related fields.
Treatment of psoriasis This is the most direct and clear application direction. Given its potential to simultaneously act on inflammation, proliferation, and immunity, purple grass furan A is expected to be developed as a novel therapeutic drug for psoriasis, especially for mild to moderate patients, and can be used as a topical medication; If the issue of oral bioavailability is resolved, it may also be used for moderate to severe systemic therapy. Compared with existing single target biologics, its multi-target characteristics may bring more comprehensive therapeutic effects and may delay or overcome the development of drug resistance. Combined use with corticosteroids or vitamin D3 analogs may produce synergistic effects, reducing their respective dosages and side effects.
Other inflammatory skin diseases Its anti-inflammatory and immune regulatory properties may be applicable for the treatment of diseases such as atopic dermatitis, eczema, and contact dermatitis. The targeting potential of TRPV1 is of great value in alleviating the severe itching associated with these diseases.
neoadjuvant therapy Its anti proliferative and apoptosis inducing activities, as well as potential effects on targets such as TOP2A, suggest that it may have value in the field of tumor therapy or serve as a sensitizer for chemotherapy. But special attention should be paid to its therapeutic window and selectivity to avoid toxicity to normal cells.
Metabolic diseases The activation of AMPK suggests its potential application in improving insulin resistance and regulating glucose and lipid metabolism, which may be related to the management of diabetes and its skin complications.
Future research prospects：
* Target validation and mechanism deepening The primary task is to use biophysical and cellular molecular biology techniques to confirm the direct interaction between purple grass furan A and the predicted targets mentioned above, and to elucidate its downstream signaling network.
* Disease model validation Systematically evaluate the efficacy and safety of local and systemic administration in animal models of psoriasis, such as the mouse model induced by imiquimod and the IL-23 transgenic mouse model.
* lead optimization A systematic structure-activity relationship (SAR) study and structural optimization were conducted using purple grass furan A as the parent nucleus, aiming to improve its activity, selectivity, solubility, and metabolic stability, and obtain candidate compounds with greater development potential.
* Development of a new delivery system Key research and development will focus on local and transdermal drug delivery systems, as well as formulation technologies to improve oral bioavailability.
* Exploration of combination therapy Explore its combination application with existing standard treatment drugs such as corticosteroids, calcipotriol, and methotrexate, evaluate synergistic effects, and provide new ideas for clinical treatment plans.
Zicao furan A is a structurally unique natural product of furan naphthoquinone isolated from the traditional Chinese medicine Zicao. Although independent and systematic research on it is still in its infancy, based on its chemical structural characteristics, extensive pharmacological activity of similar compounds, and multi-target network predicted by bioinformatics, it shows great potential for treating complex inflammatory and proliferative diseases such as psoriasis. It may intervene in disease progression from multiple dimensions, including inflammation inhibition, immune regulation, cell cycle arrest, differentiation promotion, and itch relief, by synergistically regulating multiple key targets such as AMPK, STAT3, NF - κ B, RAR, TRPV1, etc. In terms of drug properties, it has the basic advantages of small molecule drugs, but problems such as poor water solubility urgently need to be solved through formulation or chemical modification strategies. Future research should focus on the confirmation of target effects, efficacy evaluation in disease models, optimization of lead compounds, and development of novel delivery systems. With the deepening of research, purple grass furan A is expected to develop from a traditional phytochemical component into a candidate drug with clear modern scientific connotations and innovative therapeutic value. It not only provides new treatment options for psoriasis patients, but also further demonstrates the immortal vitality of natural products in the discovery of new drugs in the current era.
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