anthraquinones

:Image:Caloplaca thallincola.jpg (here Variospora thallincola), is due to the presence of anthraquinones.{{cite journal |last1=Llewellyn |first1=Theo |last2=Nowell |first2=Reuben W. |last3=Aptroot |first3=Andre | last4=Temina |first4=Marina |last5=Prescott |first5=Thomas A.K. |last6=Barraclough |first6=Timothy G. |last7=Gaya |first7=Ester |title=Metagenomics shines light on the evolution of "sunscreen" pigment metabolism in the Teloschistales (lichen-forming Ascomycota) |journal=Genome Biology and Evolution |volume=15 |issue=2 |year=2023 |doi=10.1093/gbe/evad002 |page=evad002 |pmid=36634008 |pmc=9907504}}]]

Natural pigments that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna, rhubarb, and cascara buckthorn, fungi, lichens, and some insects. A type II polyketide synthase is responsible for anthraquinone biosynthesis in the bacterium Photorhabdus luminescens.{{Cite journal|pmid=17722122|year=2007|last1=Brachmann|first1=AO|last2=Joyce|first2=SA|last3=Jenke-Kodama|first3=H|last4=Schwär|first4=G|last5=Clarke|first5=DJ|last6=Bode|first6=HB|title=A type II polyketide synthase is responsible for anthraquinone biosynthesis in Photorhabdus luminescens|volume=8|issue=14|pages=1721–8|doi=10.1002/cbic.200700300|journal=ChemBioChem}} Chorismate, formed by isochorismate synthase in the shikimate pathway, is a precursor of anthraquinones in Morinda citrifolia.{{Cite journal|pmid=12872482|year=2003|last1=Stalman|first1=M|last2=Koskamp|first2=AM|last3=Luderer|first3=R|last4=Vernooy|first4=JH|last5=Wind|first5=JC|last6=Wullems|first6=GJ|last7=Croes|first7=AF|title=Regulation of anthraquinone biosynthesis in cell cultures of Morinda citrifolia|volume=160|issue=6|pages=607–14|doi=10.1078/0176-1617-00773|journal=Journal of Plant Physiology}}

Tests for anthraquinones in natural extracts have been established.{{Cite journal|title=Antibacterial activity of leave extracts of Nymphaea lotus (Nymphaeaceae) on Methicillin resistant Staphylococcus aureus (MRSA) and Vancomycin resistant Staphylococcus aureus (VRSA) isolated from clinical samples|vauthors=Akinjogunla OJ, Yah CS, Eghafona NO, Ogbemudia FO |journal= Annals of Biological Research|year= 2010|volume= 1 |issue=2| pages= 174–184}}

• Senna glycosides from the senna.
• Frangulin in Frangula alnus.
• Aloe-emodin in aloe resin.
• Carmine, a bright-red pigment derived from insects.{{cite journal |last1=Dapson |first1=R. W. |last2=Frank |first2=M. |last3=Penney |first3=D. P. |last4=Kiernan |first4=J. A. |title=Revised procedures for the certification of carmine (C.I. 75470, Natural red 4) as a biological stain |journal=Biotechnic & Histochemistry |volume=82 |issue=1 |pages=13–15 |year=2007 |pmid=17510809 |doi=10.1080/10520290701207364 }}
• Hypericin and fagopyrin are naphthodianthrones, anthraquinone-derivatives.

{{Main|Anthraquinone process}}

A large industrial application of anthraquinones is for the production of hydrogen peroxide. 2-Ethyl-9,10-anthraquinone or a related alkyl derivative is used, rather than anthraquinone itself.{{ cite encyclopedia |author1= Goor, G. |author2=Glenneberg, J. |author3=Jacobi, S. | chapter = Hydrogen Peroxide | encyclopedia = Ullmann's Encyclopedia of Industrial Chemistry | year = 2007 | publisher = Wiley-VCH | location = Weinheim | doi = 10.1002/14356007.a13_443.pub2 |isbn=978-3527306732 }}

File:Riedl-Pfleiderer process.svg for the anthraquinone process to produce hydrogen peroxide.]]

Millions of tons of hydrogen peroxide are manufactured by the anthraquinone process.{{cite journal

| last1=Campos-Martin |first1=Jose M. |last2=Blanco-Brieva |first2=Gema |last3=Fierro |first3=Jose L. G.

| date= 2006

| title = Hydrogen Peroxide Synthesis: An Outlook beyond the Anthraquinone Process

| journal = Angewandte Chemie International Edition

| doi =10.1002/anie.200503779

| pmid = 17039551

| volume = 45

| issue =42

| pages = 6962–6984

}}

Sodium 2-anthraquinonesulfonate (AMS) is a water-soluble anthraquinone derivative that was the first anthraquinone derivative discovered to have a catalytic effect in the alkaline pulping processes.{{ cite web | url = http://smartech.gatech.edu/bitstream/1853/673/1/3370_001_071978.pdf | title = Anthraquinone / Alkali Pulping - A Literature Review | volume = Report 1 | work = Project 3370 | date = 1978-07-05 | publisher = The Institute of Paper Chemistry | location = Appleton, Wisconsin }}

{{Main|Anthraquinone dyes}}

The 9,10-anthraquinone skeleton occurs in many dyes, such as alizarin.{{ Ullmann | last1= Bien|first1=H.-S.| last2=Stawitz |first2=J.| last3= Wunderlich|first3=K. | title = Anthraquinone Dyes and Intermediates | doi = 10.1002/14356007.a02_355|year=2005 }} Important derivatives of 9,10-anthraquinone are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the dinitroanthraquinone.{{ Ullmann | author = Vogel, A. | title = Anthraquinone | doi = 10.1002/14356007.a02_347 }}

Image:AnthDyes.png. From the left: C.I.Acid Blue 43

an "acid dye" for wool (also called "Acilan Saphirol SE"), C.I. Vat Violet 1, which is applied by transfer printing using sublimation, a blue colorant commonly used in gasoline, and C.I. Disperse Red 60.]]

Derivatives of 9,10-anthraquinone include drugs such as the anthracenediones and the anthracycline family of chemotherapy drugs. The latter drugs are derived from the bacterium Streptomyces peucetius, discovered in a soil sample near the Adriatic Sea. Drugs in the anthraquinone family include the prototypical daunorubicin, doxorubicin, mitoxantrone, losoxantrone, and pixantrone. Most of these drugs, with the notable exception of pixantrone, are extremely cardiotoxic, causing irreversible cardiomyopathy, which can limit their practical usefulness in cancer treatment.

The anthracenediones also include

• Antimalarials such as rufigallol
• DNA dyes / nuclear counterstains such as DRAQ5, DRAQ7 and CyTRAK Orange for flow cytometry and fluorescence microscopy.
• Anthraquinone derivatives: rhein, emodin, aloe emodin, parietin (physcion), and chrysophanol extracted from Cassia occidentalis are toxic and known to cause hepatomyoencephalopathy in children.{{ cite journal |author1= Panigrahi, G.K. |author2=Suthar, M.K. |author3=Verma, N. |author4=Asthana, S. |author5=Tripathi, A. |author6=Gupta, S.K. |author7=Saxena, J. K. |author8=Raisuddin, S. |author9=Das, M. | title = Investigation of the interaction of anthraquinones of Cassia occidentalis seeds with bovine serum albumin by molecular docking and spectroscopic analysis: Correlation to their in vitro cytotoxic potential | journal = Food Research International |volume=77 |pages=368–377 | year = 2015 | doi = 10.1016/j.foodres.2015.08.022 }}

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File:Aloe emodin.svg

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:file:Daunorubicin2DACS.svg]]

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File:Mitoxantrone skeletal.svg

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File:Pixantrone.svg

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Dantron, emodin, and aloe emodin, and some of the senna glycosides have laxative effects. Prolonged use and abuse leads to melanosis coli.{{ cite journal | author = Müller-Lissner, S. A. | title = Adverse Effects of Laxatives: Fact and Fiction | journal = Pharmacology | volume = 47 | issue = Suppl 1 | pages = 138–145 | year = 1993 | pmid = 8234421 | doi = 10.1159/000139853 }}{{ cite journal |author1= Moriarty, K. J. |author2=Silk, D. B. | title = Laxative Abuse | journal = Digestive Diseases | volume = 6 | issue = 1 | pages = 15–29 | year= 1988 | pmid = 3280173 | doi = 10.1159/000171181 }}

Soluble anthraquinones such as 9,10-anthraquinone-2,7-disulfonic acid are used as reactants in redox flow batteries, which provide electrical energy storage.{{cite journal | last=Fontmorin | first=Jean-Marie | last2=Guiheneuf | first2=Solène | last3=Godet-Bar | first3=Thibault | last4=Floner | first4=Didier | last5=Geneste | first5=Florence | title=How anthraquinones can enable aqueous organic redox flow batteries to meet the needs of industrialization | journal=Current Opinion in Colloid & Interface Science | volume=61 | date=2022 | doi=10.1016/j.cocis.2022.101624 | page=101624}}

{{Reflist|30em}}

{{Natural phenol}}

{{Anthraquinone}}

{{Authority control}}

it:Antrachinoni