Product name: 1,8-Dihydroxyanthraquinone
Synonym name: Chrysazin; Dantron; Danthron; Istizin; Danivac; Dorbane
Catalogue No.: BP0008
Cas No.: 117-10-2
Formula: C₁₄H₈O₄
Mol Weight: 240.214
Botanical Source:
Physical Description:
Type of Compound: Anthraquinones

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
Inquire for bulk scale.




Chengdu Biopurify Phytochemicals Ltd. is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，TCM), Natural Active Pharmaceutical Ingredients worldwide.
The main services:
A. Supply active ingredients and reference standards of TCM, from mgs to kgs scale
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR(contract research), CM(contract manufacture) and PD(process development) services from lab scale, pilot scale to commercial scale(GMP is also available)
E. TCM compounds library for drug screen,more than 3000 compounds available, many of them are rare and unique.

HPLC of 1,8-Dihydroxyanthraquinone

NMR of 1,8-Dihydroxyanthraquinone

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

Introduction/Overview

1,8-Dihydroxyanthraquinone (CAS No. 117-10-2), as an important natural product, is a dihydroxyl derivative among anthraquinone compounds. Anthraquinone compounds have long attracted attention in pharmacology, natural product chemistry, and drug development due to their diverse bioactivities and unique chemical structures. 1,8-Dihydroxyanthraquinone is a derivative formed when anthrax-9,10-dione is replaced by hydroxyl groups at positions 1 and 8. It has a significant apoptosis-inducing effect and is widely present as a plant metabolite in various plants.

In recent years, with the deepening of research into tumor molecular mechanisms, 1,8-dihydroxyanthraquinone has shown potential application value in the anti-tumor field, especially in studies on the treatment of Hodgkin lymphoma (HL), demonstrating regulatory ability targeting multiple key molecular targets. This paper provides a systematic review of the chemical structure and physicochemical properties, plant origin and extraction methods, pharmacological activity, mechanism of action and molecular targets, druggability evaluation, and pharmacokinetic characteristics of 1,8-dihydroxyanthraquinone, and explores its clinical application prospects and future research directions, aiming to provide theoretical basis and research reference for drug development of this natural product.

Chemical structure and physicochemical properties

The molecular formula of 1,8-dihydroxyanthraquinone is C14H8O4, with a molecular weight of 240.21. Its structure is based on the anthrase-9,10-dione skeleton, introducing hydroxyl groups at positions 1 and 8 respectively, forming two adjacent hydroxyl substituents. This structure imparts unique chemical properties and biological activity. The molecule contains two carbonyl groups and two hydroxyl groups, which can form hydrogen bonds and enhance their ability to bind with biological macromolecules.

In terms of physicochemical properties, the LogP value of 1,8-dihydroxyanthraquinone is about 3.0, indicating moderate lipid solubility that facilitates cell membrane penetration. The polar surface area (TPSA) is 74.6 Ų, indicating certain water-soluble and polar characteristics in living organisms. The molecule contains four hydrogen bond receptors, increasing its binding potential to target proteins. The blood-brain barrier has a low penetration capacity, indicating limited distribution in the central nervous system.

Additionally, 1,8-dihydroxyanthraquinone exhibits good chemical tolerance, but its structure may change under light exposure and oxidation conditions, so attention should be paid during storage and application. A positive Ames test suggests a certain genotoxicity risk, and its safety should be prioritized during drug development.

Plant Origins and Extraction Methods

1,8-Dihydroxyanthraquinone is widely found in various plants, especially in the roots, stems, and leaves of certain traditional medicinal plants. Typical plant sources include Rheum spp., polygonum multiflorum, and plants from the Polygonaceae family, which are used in traditional Chinese medicine to treat inflammation, tumors, and liver diseases.

The extraction method mainly uses organic solvent extraction combined with chromatography separation technology. Common extraction solvents include ethanol, methanol, ethyl acetate, etc., which can effectively dissolve anthraquinone compounds. The extraction process generally includes the following steps:

1. Drying and crushing of plant materials;
2. Organic solvent extraction with extraction at room temperature or under reflux conditions for several hours;
3. Filter and concentrate the extract;
4. Separation and purification are performed by silica gel column chromatography or high-performance liquid chromatography (HPLC);
5. Pure products are identified for structure through methods such as mass spectrometry and nuclear magnetic resonance (NMR).

In recent years, the application of ultrasound-assisted extraction and microwave-assisted extraction technologies has improved extraction efficiency and purity, reduced solvent usage and extraction time, and promoted the industrialization of 1,8-dihydroxyanthraquinone.

Pharmacological activity research

The pharmacological activity of 1,8-dihydroxyanthraquinone is mainly reflected in its antitumor, anti-inflammatory, and antioxidant properties. Numerous in vitro cell experiments and some animal model studies have shown that this compound can effectively induce tumor cell apoptosis, inhibit cell proliferation, and exhibits selective toxicity against various tumor types.

Antitumor activity

In Hodgkin lymphoma cell lines, 1,8-dihydroxyanthraquinone significantly inhibits tumor cell growth by regulating cyclins and apoptosis-related proteins. Its mechanism of action involves multiple signaling pathways, including inhibition of the STAT3 signaling pathway and downregulation of the anti-apoptotic protein MCL1. Additionally, this compound can induce loss of mitochondrial membrane potential, activate the caspase family, and promote apoptosis.

Anti-inflammatory and antioxidant effects

1,8-Dihydroxyanthraquinone demonstrates the ability to inhibit the release of inflammatory factors in inflammation models, reduce oxygen free radical production, and protect cells from oxidative stress damage. These effects lay the foundation for its potential applications in chronic inflammation-related diseases.

Other pharmacological effects

Some studies suggest that 1,8-dihydroxyanthraquinone also has the potential to regulate neurotransmitter metabolism, possibly affecting nervous system function by regulating targets such as MAOA, but related research is still in its early stages.

Mechanism of action and molecular targets

The mechanism of action of 1,8-dihydroxyanthraquinone in the anti-Hodgkin lymphoma treatment involves several key molecular targets, as detailed below:

• BLM (Bloom syndrome protein): As a DNA helilase, BLM is involved in DNA repair and genome stability. 1,8-Dihydroxyanthraquinone may influence tumor cells' DNA repair ability by regulating BLM activity, increasing their sensitivity to DNA damage.

• MCL1 (Myeloid Cell Leukemia 1): An anti-apoptotic protein that regulates cell survival. This compound can downregulate MCL1 expression and promote apoptosis.

• CDC25A/CDC25B (cell division cyclin phosphatase): regulate the progression of the cell cycle. 1,8-Dihydroxyanthraquinone blocks the cell cycle and suppresses tumor cell proliferation by inhibiting the activities of CDC25A and CDC25B.

• PTPN1 (protein tyrosine phosphatase 1B): involved in signal transduction regulation. Its regulation helps regulate cellular metabolism and apoptosis pathways.

• STAT3 (Signal Transduction and Transcription Activator 3): A key transcription factor that promotes tumor growth and immune evasion. 1,8-Dihydroxyanthraquinone inhibits the phosphorylation and activation of STAT3, blocking its downstream tumor-causing signals.

• MAOA (Monoamine Oxidase A): Regulates neurotransmitter metabolism and may affect the tumor microenvironment.

• ESR2 (estrogen receptor β): Regulates cell proliferation and apoptosis; 1,8-dihydroxyanthraquinone may play a role by modulating ESR2-mediated signaling pathways.

• TOP1 (Topoisomerase I): Involved in DNA topology regulation, TOP1 inhibitors targeting TOP1 have been used in antitumor drug development.

Through multiple regulation of these targets, 1,8-dihydroxyanthraquinone achieves comprehensive inhibitory effects on tumor cells, demonstrating multi-target, multi-pathway anti-tumor potential.

Druggability evaluation and pharmacokinetics

Druggability evaluation is a key step in the development of natural product drugs. The molecular weight of 1,8-dihydroxyanthraquinone is 240.21, meeting the molecular weight requirements in the Lipinski rule; the LogP value is 3.0, indicating suitable lipophilic properties that facilitate oral drug absorption. TPSA was 74.6 Ų, indicating moderate polarity and favorable cell membrane penetration.

It has 4 hydrogen bond receptors, meeting the requirements for drug molecules to bind to target proteins. The low penetration capacity of the blood-brain barrier suggests its limited distribution in the central nervous system, which may reduce the risk of CNS toxicity but restricts its application in neurological diseases.

In terms of safety, the Ames test for 1,8-dihydroxyanthraquinone was positive, indicating potential genotoxicity, which requires further validation through in vivo toxicology tests and long-term safety evaluation. Key safety indicators such as hepatotoxicity, cardiotoxicity, and hERG suppression remain unclear, so future research requires focused attention.

Currently, relevant data on pharmacokinetics are relatively limited. Preliminary in vitro metabolic studies indicate that this compound may be metabolized via the hepatic cytochrome P450 enzyme system, exhibiting a certain first-pass effect. Its parameters such as bioavailability, volume of distribution, and clearance rate still require systematic research to guide clinical dosage design and administration regimen optimization.

Prospects and outlooks for clinical applications

1,8-Dihydroxyanthraquinone, as a natural compound with multi-target antitumor activity, has shown promising application potential in the treatment of Hodgkin lymphoma. By regulating tumor cell proliferation, apoptosis, and signaling pathways, it offers a new therapeutic strategy. Combined with existing chemotherapy regimens, 1,8-dihydroxyanthraquinone is expected to be used as an adjunct or combination therapy to improve treatment efficacy and reduce the incidence of drug resistance.

However, clinical translation still faces many challenges. First, genotoxicity risk must be reduced through systematic safety assessments and structural modifications; Second, the pharmacokinetic properties are imperfect, limiting the diversification of dosage form development and administration methods; Additionally, the lack of systematic preclinical animal models and clinical trial data limits its clinical extension.

Future research directions should include:

• Structural optimization and derivative design to enhance activity and safety;
• systematic pharmacokinetic and toxicological evaluation;
• In-depth analysis of multi-target mechanisms combined with systems biology methods;
• Preclinical animal model validation and early clinical trial implementation;
• Exploration of combination medication strategies and evaluation of synergistic effects.

Through multidisciplinary collaboration, 1,8-dihydroxyanthraquinone is expected to become an important candidate for next-generation natural anti-tumor drugs.

Conclusion

In summary, 1,8-dihydroxyanthraquinone, as a naturally occurring product with a unique structure and significant activity, shows broad application prospects in anti-tumor treatment, especially in the treatment of Hodgkin lymphoma. Its multi-target and multi-mechanism mode of action offers new ideas for tumor treatment. However, druggability and safety issues still require in-depth study, and the lack of pharmacokinetic data limits the clinical translation process. In the future, structural optimization, mechanism research, and preclinical evaluation should be strengthened to promote its advancement toward clinical application. The development of 1,8-dihydroxyanthraquinone not only enriches research in natural product pharmacology, but also provides new opportunities for innovation in tumor treatment drugs.