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Synonym name: Greenhartin; Taiguic acid; Tecomin; Groenhartin; Lapachoic acid
Catalogue No.: BP0841
Cas No.: 84-79-7
Formula: C15H14O3
Mol Weight: 242.274
Botanical Source: Widespread occurrence in the plant world, particularly in heartwood, bark and roots, e.g. the Bignoniaceae and various Tabebuia, Tecomella and Tectona spp.
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 Lapachol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
54.3700
2.9130
.4935
.0623
6.2410
34.6795
Low
89.9715
2.5180
Yes
Yes
No
No
No
Yes
0.9
No
Yes
Yes
Yes
Lapachol, chemically named 2-hydroxy-3-(3-methylbut-2-en-1-yl)-1,4-naphthoquinone, is a naturally occurring hydroxy-1,4-naphthoquinone compound. Since its first isolation in 1882 from the bark of the South American endemic plant Tabebuia avellanedae (Genus Tabebuia), quinone has become an important subject of natural pharmacological research due to its remarkable biological activity. Its unique chemical structure endows it with diverse pharmacological activities, covering antibacterial, anti-tumor, anti-inflammatory, and regulation of plant metabolism, showing particular potential in the field of tumor treatment.
In recent years, with advances in molecular biology and medicinal chemistry, the mechanism of action of Huangzhonghuaquinone and its interactions with various disease-related molecular targets have gradually been revealed, especially in research on its application in digestive system tumors such as colon cancer, which has made significant progress. This paper aims to systematically review the chemical structure, origins, pharmacological activity, mechanism of action, druggability evaluation, and clinical application prospects of Huangzhonghuaquinone, providing a theoretical foundation and reference for subsequent related research and new drug development.
The molecular formula of Huangzhonghuaquinone is C15H14O3, with a molecular weight of 242.2740. Its core structure is a 1,4-naphthoquinone backbone, which is replaced at positions 2 and 3 by hydroxyl groups and 3-methylbuty-2-en-1-, respectively, forming a conjugated system with strong electron donor and acceptor characteristics. This structure gives it excellent chemical reactivity and is especially prominent in redox reactions.
In terms of physicochemical properties, the LogP value of Huangzhonghuaquinone is 2.9130, indicating moderate lipid solubility, which is beneficial for cell membrane penetration and bioavailability. Its topological polar surface area (TPSA) is 54.37 Ų, suggesting that the molecule has certain polarity that facilitates binding with biological macromolecules such as proteins. Low water solubility (0.0623 mg/mL) limits its solubility in the aqueous phase and may affect its distribution and administration in vivo. The blood-brain barrier has low permeability, indicating limited penetration in the central nervous system. The hERG channel inhibition test was negative, indicating a low risk of cardiotoxicity. The Ames trial scored 0.9, indicating a low genotoxicity risk and good safety.
Tabebuia quinone is mainly found in the bark of plants of the genus Tabebuia spp., especially species such as Tabebuia avellanedae and Tabebuia impetiginosa. These plants are widely distributed in tropical and subtropical regions of South America and have traditionally been used by local residents to treat diseases such as infections, inflammation, and tumors.
Traditional methods for extracting quinone typically use organic solvents such as ethanol, methanol, or ethyl acetate, combined with hot reflux or ultrasound-assisted extraction techniques to improve extraction efficiency. The extract undergoes separation and purification steps such as concentration, fractionation, and column chromatography, ultimately obtaining high-purity Huangzhonghua quinone. In recent years, green and efficient technologies such as supercritical fluid extraction and microwave-assisted extraction have also been applied to the extraction of quinone in Huangzhonghua, significantly improving yield and purity while reducing environmental pollution.
Huangzhonghuaquinone exhibits broad-spectrum antibacterial effects, particularly showing significant inhibitory effects against Gram-positive bacteria such as Staphylococcus aureus and certain Gram-negative bacteria. Its antibacterial mechanism mainly involves cell membrane destruction and disruption of the cellular respiratory chain. In vitro experiments show that Huangzhonghuaquinone can inhibit bacterial growth and reproduction, and also exhibits certain activity against resistant strains, suggesting its potential application value in the context of antibiotic resistance.
The antitumor activity of Huangzhonghuaquinone is one of its most noteworthy pharmacological properties. Multiple in vitro and in vivo studies have shown that Huangzhonghuaquinone has cytotoxic effects on various tumor cell lines, with particularly prominent effects in colon, breast, and lung cancer cells. Its antitumor effects include inducing apoptosis, blocking the cell cycle, and inhibiting tumor cell migration and invasion.
In colon cancer models, Huangzhonghuaquinone inhibits tumor cell proliferation and survival through multi-target regulation, significantly delaying tumor growth. Huangzhonghuaquinone can also enhance the efficacy of chemotherapy drugs, showing potential synergistic effects.
Huangzhonghuaquinone has strong anti-inflammatory effects, inhibiting the expression of inflammatory mediators such as tumor necrosis factor α (TNF-α), interleukin-6 (IL-6), and cyclooxygenase-2 (COX-2), thereby reducing inflammatory responses. Its anti-inflammatory mechanism involves inhibition of the NF-κB signaling pathway and regulation of oxidative stress, suggesting its potential application in inflammation-related diseases.
As a plant metabolite, quinone also exhibits effects in regulating plant growth and resistance to stress. Its redox properties give it certain activity in free radical scavenging and antioxidant properties, potentially having a positive impact on cell protection and tissue repair.
The multi-target mechanism of Huangzhonghuaquinone forms the basis for its pharmacological diversity. For colon cancer, Huangzhonghuaquinone mainly exerts its antitumor effect by regulating the following key molecular targets:
AMPK (PRKAA1): As a regulator of cellular energy metabolism, AMPK activation promotes metabolic stress in tumor cells, inducing autophagy and apoptosis. Huangzhonghuaquinone can activate the AMPK signaling pathway and inhibit tumor cell growth.
BCL2: Downregulation of the anti-apoptotic protein BCL2 helps promote tumor cell apoptosis. Huangzhonghuaquinone disrupts the intracellular anti-apoptotic balance by inhibiting BCL2 expression.
STAT3: As a transcription factor, STAT3 is involved in tumor cell proliferation and immune escape. Huangzhonghuaquinone inhibits the phosphorylation and activity of STAT3, blocking the expression of its downstream tumor-causing genes.
ABCB1: Inhibition of multidrug resistance protein ABCB1 helps reverse chemotherapy resistance in tumor cells. Huangzhonghuaquinone can reduce ABCB1 expression and enhance intracellular accumulation of chemotherapy drugs.
ALOX5: Involved in inflammation and tumor microenvironment regulation, Huangzhonghuaquinone reduces pro-tumor inflammatory responses by inhibiting ALOX5 activity.
LCK: As a tyrosine kinase, LCK regulates immune cell function and tumor signaling. Huangzhonghuaquinone regulates LCK to help regulate the tumor immune microenvironment.
TOP1: Topoisomerase I is a key enzyme for DNA replication and transcription. Huangzhonghuaquinone inhibits TOP1 activity and inhibits tumor cell proliferation.
RELA (NF-κB p65 subunit): The NF-κB signaling pathway plays a central role in inflammation and tumors. Huangzhonghuaquinone inhibits RELA activation and weakens pro-tumor inflammatory signals.
MAPK1: The MAPK signaling pathway, involved in cell proliferation and differentiation, is an important regulatory node for tumor growth. Huangzhonghuaquinone regulates MAPK1 activity and inhibits tumor development.
TNF: Downregulation of pro-inflammatory cytokine TNF helps alleviate tumor-related inflammation. Huangzhonghuaquinone reduces TNF expression and improves the tumor microenvironment.
In summary, Huangzhonghuaquinone regulates tumor cell proliferation, apoptosis, migration, and immune escape through multi-target and multi-pathway synergistic effects, demonstrating a complex and effective anti-tumor mechanism.
The druggability evaluation of Huangzhonghuaquinone indicates it has certain potential for drug development. Its molecular weight of 242.2740 complies with the Lipinski rule, and a LogP value of 2.9130 indicates moderate lipid solubility, which is beneficial for oral absorption. A TPSA value of 54.37 Ų supports its excellent membrane permeability. Low water solubility is a major challenge in drug development, requiring improved solubility and bioavailability through pharmaceutical formulation technologies such as nanocarriers, liposomes, or salt formation.
The low permeability of the blood-brain barrier limits its application in central nervous system diseases, but it helps reduce toxic side effects in the central nervous system. Negative hERG channel suppression suggests a lower risk of cardiotoxicity and better safety. Ames trial results showed a low genotoxicity risk, further supporting its safety.
In terms of pharmacokinetics, Huangzhonghuaquinone is absorbed orally relatively quickly, but its bioavailability is limited due to poor water solubility and first-pass effects. Its distribution in vivo is mainly concentrated in the liver and kidneys, with metabolic pathways primarily carried out through oxidative metabolism via the hepatic cytochrome P450 enzyme system. Excretion is mainly through bile and urine. Future research needs to further clarify the activity and toxicity of its metabolites and optimize drug administration regimens to enhance therapeutic outcomes.
As a versatile natural product, Huangzhonghuaquinone shows broad clinical application prospects in antibacterial, antitumor, and anti-inflammatory fields. Especially in colon cancer treatment, Huangzhonghuaquinone regulates tumor cell proliferation and apoptosis through multiple targets, offering potential adjunctive therapeutic value. Moreover, its inhibitory effect on multidrug resistance proteins offers new ideas for overcoming chemotherapy resistance.
However, the clinical translation of Huangzhonghuaquinone still faces several challenges. First, its poor water solubility and low bioavailability limit its efficacy, which needs to be addressed through formulation improvements and optimization of administration routes. Second, although in vitro and animal experiments have shown good results, there is a lack of systematic clinical trial data to support their safety and efficacy. Finally, the pharmacokinetic characteristics and toxicity of Huangzhonghuaquinone and the toxicity of its metabolites still require further study.
In the future, combining modern drug design technologies, such as molecular modification, nanocarrier delivery, and combination drug strategies, it is expected to enhance the efficacy and safety of Huangzhonghuaquinone. At the same time, conducting multicenter, randomized controlled clinical trials will lay a solid foundation for its clinical application. Additionally, in-depth analysis of its molecular mechanisms will help discover new drug targets and therapeutic strategies.
Huangzhonghuaquinone, as a natural hydroxy-1,4-naphthoquinone compound with rich biological activity, demonstrates broad application potential in antibacterial, antitumor, and anti-inflammatory fields due to its unique chemical structure and multi-target mechanism. Especially in the treatment of malignant tumors such as colon cancer, Huangzhonghuaquinone exerts significant anti-tumor effects by regulating key targets such as AMPK, BCL2, and STAT3.
Although its druggability shows certain advantages, poor water solubility and in vivo pharmacokinetic characteristics still need optimization. Future research should focus on formulation technology innovation, in-depth mechanism analysis, and clinical trial validation, in order to promote Huangzhonghuaquinone from the laboratory to clinical application. In summary, as an important candidate for natural product drug development, Huangzhonghuaquinone has the potential to become a novel antitumor drug and deserves ongoing attention and in-depth exploration.
Shenshuai
Wenjing
Hedandan
