chrysophanol

chrysophanol
Vortioxetine · Public domain · source
Name	Chrysophanol
Other names	1,8-dihydroxy-3-methylanthraquinone
CAS number	481-74-3
Formula	C15H10O4
Molar mass	254.24 g·mol−1
Appearance	orange crystalline solid
Melting point	198–201 °C
Solubility	sparingly soluble in water; soluble in organic solvents

chrysophanol

Chrysophanol is an anthraquinone compound found in multiple China-linked traditional medicine herbs and diverse plant, fungal, and lichen species. It has been studied across fields connecting Traditional Chinese medicine, pharmacology, organic chemistry, toxicology, and analytical chemistry for its spectral properties, biosynthetic origins, bioactivities, and synthetic modifications. Research on chrysophanol appears in literature involving collaborations among institutions like University of Tokyo, Peking University, Harvard University, and Max Planck Society.

Chemistry and physical properties

Chrysophanol is an anthraquinone derivative with the systematic name 1,8-dihydroxy-3-methylanthraquinone. Structural characterization links it to the broader families investigated at Royal Society of Chemistry venues and presented at conferences such as the American Chemical Society meetings and the International Conference on Organic Synthesis. The molecule shows typical UV–visible absorption bands used in spectroscopic studies at facilities like Stanford University and ETH Zurich, and its NMR spectra are reported in journals associated with Wiley-VCH and Elsevier. Crystallographic studies of anthraquinones often cite methodologies from International Union of Crystallography, and chrysophanol crystals display monoclinic symmetry similar to related compounds discussed in papers from Cambridge University Press.

Natural sources and biosynthesis

Chrysophanol occurs in plants such as species within Rheum (rhubarb) and Cassia, and in fungi like Penicillium and Aspergillus, and in lichens studied by researchers at Smithsonian Institution and Natural History Museum, London. Ethnopharmacological surveys connecting Traditional Chinese medicine and Kampo formulations document its presence in preparations alongside herbs cataloged at institutions like Kew Gardens and Royal Botanic Gardens Edinburgh. Biosynthetic pathways involve polyketide synthase systems analogous to those characterized at Max Planck Institute for Chemical Ecology and biochemistry groups at University of California, Berkeley and ETH Zurich, with acetyl-CoA/malonyl-CoA condensations leading to anthraquinone scaffolds commonly referenced in reviews in Journal of Biological Chemistry and Nature Chemical Biology.

Pharmacology and biological activities

Biological investigations report chrysophanol exhibits activities including anti-inflammatory, antimicrobial, and potential anticancer effects in models used at National Institutes of Health labs and oncology centers such as MD Anderson Cancer Center. Studies often appear in journals affiliated with American Association for Cancer Research and Springer Nature. Mechanistic work implicates pathways involving apoptosis regulators studied at Cold Spring Harbor Laboratory and signaling cascades investigated at Broad Institute. Antimicrobial assays reference standards from Centers for Disease Control and Prevention and collaborate with microbiology groups at Pasteur Institute and Wellcome Trust–funded labs. Neuroprotective and hepatoprotective effects are evaluated in animal models used by researchers at Johns Hopkins University and Osaka University.

Toxicology and safety

Toxicity assessments reporting hepatotoxicity and nephrotoxicity have been conducted in toxicology units at Food and Drug Administration and academic toxicology departments at University of Cambridge and Seoul National University. Genotoxicity and mutagenicity evaluations reference protocols from Organisation for Economic Co-operation and Development and are published in outlets associated with European Medicines Agency and Environmental Protection Agency. Safety profile discussions appear alongside regulatory considerations from World Health Organization monographs and pharmacopeial entries curated by United States Pharmacopeia and British Pharmacopoeia committees.

Analytical methods and detection

Detection and quantification of chrysophanol use chromatographic techniques such as HPLC and UHPLC methods developed in laboratories at University of California, San Francisco and Imperial College London, often coupled with mass spectrometry platforms made by companies like Thermo Fisher Scientific and Agilent Technologies. LC–MS/MS and GC–MS methods appear in analytical reports in journals published by ACS Publications and Elsevier, and NMR-based metabolomics studies are conducted using spectrometers housed at Max Planck Institute for Biophysical Chemistry and Riken. Sample preparation workflows are described in methodological papers from National Institute of Standards and Technology and collaborative consortia including Human Metabolome Database contributors.

Synthetic routes and derivatives

Synthetic strategies for chrysophanol and analogs have been developed in academic groups at Massachusetts Institute of Technology, University of Oxford, and Tsinghua University, employing Friedel–Crafts, oxidative cyclization, and polyketide-mimetic routes discussed at Gordon Research Conferences and in publications by Royal Society of Chemistry. Semisynthetic modification and derivatization to produce sulfonated, glycosylated, and halogenated derivatives are explored with relevance to medicinal chemistry programs at Novartis and Pfizer research centers. Structure–activity relationship studies and patent literature are connected to filings with offices like the European Patent Office and the United States Patent and Trademark Office.

Category:Anthraquinones Category:Natural products