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Synonym name: "2',4,4'-Trihydroxy-6'-methoxy-3'-prenylchalcone";569-83-5
Catalogue No.: BP1458
Cas No.: 6754-58-1
Formula: C21H22O5
Mol Weight: 354.402
Physical Description: Orange powder
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.
HPLC of Xanthohumol
HNMR of Xanthohumol
Storage conditions：Short-term storage at 2~8℃, long-term storage at -20 ~ -80℃
86.9900
4.3428
4.2499
.0615
4.2140
9.4444
Low
91.6776
2.6074
Yes
No
Yes
No
Yes
No
0.0
No
Yes
Yes
Yes
Xanthohumol (CAS No.: 6754-58-1) is a natural flavonoid compound isolated from hops (Humulus lupulus L.). As a unique polyphenol component in hops, xanthium has attracted widespread attention in the field of natural product pharmacology in recent years due to its diverse biological activities and potential medicinal value. Huanghumol not only exhibits significant antitumor and anti-angiogenic activity, but also has inhibitory effects against various viruses, including bovine viral diarrheal virus (BVDV), rhinovirus, herpes simplex virus types 1 and 2 (HSV-1, HSV-2), and cytomegalovirus (CMV). Additionally, yellow humus phenol demonstrates good anti-inflammatory and metabolic regulatory potential by inhibiting key enzymes such as diacylglyceryltransferase (DGAT), cyclooxygenase-1 (COX-1), and cyclooxygenase-2 (COX-2).
This paper will systematically review the chemical structure and physicochemical properties, plant origins, and extraction methods of huanghumol, analyze its pharmacological activity and mechanism of action in detail, explore its molecular basis for antitumor and antiviral properties by combining molecular targets, evaluate its druggability and pharmacokinetic characteristics, and look ahead to its potential and challenges for future clinical applications, aiming to provide theoretical basis and reference for further research and development of huanghumol.
Huanghumol belongs to the flavonoid class, specifically an isoflavone derivative. Its molecular formula is C21H22O5, and its molecular weight is 354.4020. The molecular structure of xanthol contains multiple phenolic hydroxyl and methoxy groups, giving it strong antioxidant capacity. Its chemical structure features include a flavonoid backbone bonded to a side chain, which contains a α,β-unsaturated ketone structure, which is of great significance for its biological activity.
In terms of physicochemical properties, the LogP value of anthamic phenol is 4.3428, indicating high lipid solubility, which facilitates penetration of cell membranes but may limit its water solubility. Its topological pole surface area (TPSA) is 86.9900, indicating it has certain polar groups, which helps bind to biomacromolecules. It has relatively low water solubility (0.0615 mg/mL), which poses certain challenges for its bioavailability. Huanghumin has low blood-brain barrier permeability, indicating limited distribution in the central nervous system. Importantly, xanthamol does not exhibit hERG channel inhibitory activity, and the Ames-induced mutagenic test results are negative, indicating high safety and low potential arrhythmogenic risk.
Oxanthumol is mainly found in the female flowers of hops, especially in the pollen sacs and pollen glands, with higher levels. As an important raw material for beer production, hops have a complex chemical composition. Humus phenol is a flavonoid polyphenol with abundant content and significant biological activity.
Traditional methods for extracting yellow humus mainly use organic solvent extraction methods, such as ethanol, methanol, or ethyl acetate, combined with modern technologies like ultrasound-assisted extraction (UAE) and microwave-assisted extraction (MAE) to improve extraction efficiency and purity. After liquid-liquid separation, column chromatography, and high-performance liquid chromatography (HPLC) purification, high-purity yellow humus phenol can be obtained. In recent years, supercritical carbon dioxide extraction (SFE-CO2) technology has also been applied to extract yellow humus phenol from hops, offering advantages of being environmentally friendly and highly selective.
Optimizing the extraction process not only affects the yield of anthamphenol but also relates to the stability of its bioactive components and the feasibility of subsequent pharmaceutical development. Research shows that extraction conditions such as solvent polarity, temperature, time, and hop variety all significantly affect the content of xanthul.
Huanghumol exhibits significant cell proliferation inhibition and pro-apoptosis effects across various tumor cell lines. Its anti-tumor activity covers various solid tumors including breast, prostate, colorectal, and liver cancers. In vitro studies show that oxahumol can regulate multiple signaling pathways to inhibit tumor cell proliferation, migration, and invasion, inducing cell cycle arrest and apoptosis.
Tumor growth and metastasis depend on the formation of new blood vessels. Oxanthumol blocks tumor angiogenesis by inhibiting the proliferation of vascular endothelial cells and the formation of the lumen. Its mechanism involves downregulating vascular endothelial growth factor (VEGF) and its receptor expression, inhibiting related signaling pathways, and reducing angiogenesis activity in the tumor microenvironment.
Huanghumin exhibits broad-spectrum antiviral activity, especially against bovine viral diarrhea virus (BVDV), rhinovirus, herpes simplex virus types 1 and 2 (HSV-1, HSV-2), and cytomegalovirus (CMV). Its antiviral mechanisms may include disrupting the viral replication cycle, inhibiting viral protein synthesis, and blocking the binding of the virus to host cells.
As an inhibitor of COX-1 and COX-2, xanthamin has significant anti-inflammatory effects, reducing the production of inflammatory mediators and alleviating inflammatory responses. Additionally, by inhibiting DGAT activity, xanthamol participates in lipid metabolism regulation, showing potential therapeutic value for metabolic syndrome and fatty liver diseases.
The multi-target mechanism of xanthum is the foundation of its broad pharmacological activity. In response to antitumor effects, xanthamol regulates several key proteins and signaling pathways:
Additionally, xanthamol exerts anti-inflammatory and anti-angiogenesis effects by inhibiting COX-1 and COX-2, reducing prostaglandin synthesis. Its inhibitory effect on DGAT regulates lipid synthesis and affects energy metabolism.
In terms of antiviral effects, xanthamol may exert antiviral activity by blocking viruses from entering host cells, inhibiting viral gene expression, and inhibiting protein synthesis.
Drugability evaluation of xanthamol shows it has certain potential, but also faces challenges. Its high lipophilic solubility (LogP 4.34) favors cell membrane penetration, but its low water solubility (0.0615 mg/mL) limits its oral bioavailability. Low blood-brain barrier permeability means its application in central nervous system diseases is limited.
In terms of safety, xanthamol does not inhibit hERG channels, reducing the risk of arrhythmias, and the Ames test was negative, indicating a low risk of mutagenic behavior and good safety.
Pharmacokinetic studies show that xanthamol metabolizes rapidly in the body, mainly through hepatic metabolic enzyme systems, exhibiting a first-pass effect. The activity and toxicity of its metabolites require further research. To improve its pharmacokinetic properties, researchers have tried to use pharmacodynamic strategies such as nanocarriers, liposomes, and solid dispersions to enhance its solubility and bioavailability.
As a multifunctional natural product, xanthumin possesses broad pharmacological activity, showing great potential especially in anti-tumor and antiviral fields. The future clinical application prospects are mainly reflected in the following aspects:
Antitumor drug development: By combining the multi-target mechanism of xanthuminophenol, it can be developed as adjuvant or combination chemotherapy drugs, especially targeting hormone-dependent and drug-resistant tumors. Further preclinical and clinical studies will verify its efficacy and safety.
Antiviral therapy: For viral infections such as HSV and CMV, xanthine is expected to serve as a novel antiviral drug or adjunct therapy, especially in the context of increasingly prominent viral resistance.
Anti-inflammatory and metabolic diseases: The COX inhibition and lipid metabolism regulation effects of huanghumol provide new ideas for the treatment of inflammatory diseases and metabolic syndromes.
Drug formulation innovation: To address the issues of low water solubility and insufficient bioavailability of xanthium, the development of nanotechnology and novel delivery systems will be key to enhancing its clinical application value.
Although xanthamol shows good activity in vitro and animal models, its clinical translation still faces challenges in pharmacokinetics, dose optimization, long-term safety, and efficacy verification. In the future, multi-center, multi-stage clinical trial design should be strengthened, integrating modern medicinal chemistry and pharmaceutics techniques to promote xanthuminohum from the laboratory to clinical practice.
As an important natural flavonoid product in hops, xanthum demonstrates broad anti-tumor, antiviral, and anti-inflammatory potential due to its unique chemical structure and multi-target pharmacological activity. Its mechanism of action involves multiple key cellular signaling pathways and enzyme regulation, providing a rich molecular foundation for the development of novel natural drugs. Drug-friendly evaluations show that yellow humus has good safety, but pharmacokinetic characteristics such as water solubility and bioavailability still need optimization.
In the future, with advances in extraction and purification technologies, pharmaceutical formulation innovation, and clinical research, xanthumin is expected to become a star compound in the field of natural product pharmacology, driving the transformation of natural flavonoid drugs into clinical applications. Ongoing basic and applied research will open new avenues for the drug development and disease treatment of xanthagol.
Shenshuai
Wenjing
Hedandan
