''For the parent molecule 9,10-anthraquinone, see

anthraquinone Anthraquinone, also called anthracenedione or dioxoanthracene, is an aromatic organic compound with formula . Isomers include various quinone derivatives. The term anthraquinone however refers to the isomer, 9,10-anthraquinone (IUPAC: 9,10-dioxoan ...

Anthraquinones (also known as anthraquinonoids) are a class of naturally occurring phenolic compounds based on the 9,10-anthraquinone skeleton. They are widely used industrially and occur naturally.

Occurrence in plants

: Natural

pigment A pigment is a colored material that is completely or nearly insoluble in water. In contrast, dyes are typically soluble, at least at some stage in their use. Generally dyes are often organic compounds whereas pigments are often inorganic compou ...

s that are derivatives of anthraquinone are found, inter alia, in aloe latex, senna,

rhubarb Rhubarb is the fleshy, edible stalks ( petioles) of species and hybrids (culinary rhubarb) of '' Rheum'' in the family Polygonaceae, which are cooked and used for food. The whole plant – a herbaceous perennial growing from short, thick rhi ...

, and cascara buckthorn,

fungi A fungus ( : fungi or funguses) is any member of the group of eukaryotic organisms that includes microorganisms such as yeasts and molds, as well as the more familiar mushrooms. These organisms are classified as a kingdom, separately fr ...

lichen A lichen ( , ) is a composite organism that arises from algae or cyanobacteria living among filaments of multiple fungi species in a mutualistic relationship.insect Insects (from Latin ') are pancrustacean hexapod invertebrates of the class Insecta. They are the largest group within the arthropod phylum. Insects have a chitinous exoskeleton, a three-part body ( head, thorax and abdomen), three pa ...

s. A type II polyketide synthase is responsible for anthraquinone biosynthesis in the bacterium ''

Photorhabdus luminescens ''Photorhabdus luminescens'' (previously called ''Xenorhabdus luminescens'') is a Gammaproteobacterium of the family Morganellaceae, and is a lethal pathogen of insects. It lives in the gut of an entomopathogenic nematode of the family Hetero ...

''.

Chorismate Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for: * The aromatic amino acids phenylalanine, tryptophan, and tyrosine * Indole, indole ...

, formed by

isochorismate synthase Isochorismate synthase) is an isomerase enzyme that catalyzes the first step in the biosynthesis of vitamin K2 (menaquinone) in ''Escherichia coli''. Reaction Isochorismate synthase, belongs to the isomerase enzyme family. More specifically it ...

in the shikimate pathway, is a precursor of anthraquinones in ''

Morinda citrifolia ''Morinda citrifolia'' is a fruit-bearing tree in the coffee family, Rubiaceae. Its native range extends across Southeast Asia and Australasia, and was spread across the Pacific by Polynesian sailors. The species is now cultivated throughout ...

''. Tests for anthraquinones in natural extracts have been established. * Senna glycosides from the senna. *Frangulin in

Frangula alnus ''Frangula alnus'', commonly known as alder buckthorn, glossy buckthorn, or breaking buckthorn, is a tall deciduous shrub in the family Rhamnaceae. Unlike other "buckthorns", alder buckthorn does not have thorns. It is native to Europe, northern ...

. * Aloe-emodin in

aloe ''Aloe'' (; also written ''Aloë'') is a genus containing over 650 species of flowering succulent plants.WFO (2022): Aloe L. Published on the Internet;http://www.worldfloraonline.org/taxon/wfo-4000001341. Accessed on: 06 Nov 2022 The most wi ...

resin. *

Carmine Carmine ()also called cochineal (when it is extracted from the cochineal insect), cochineal extract, crimson lake, or carmine lake is a pigment of a bright-red color obtained from the aluminium complex derived from carminic acid. Specific code ...

, a bright-red pigment derived from insects. *

Hypericin Hypericin is a naphthodianthrone, an anthraquinone derivative which, together with hyperforin, is one of the principal active constituents of '' Hypericum'' ( Saint John's wort). Hypericin is believed to act as an antibiotic, antiviral and non- ...

and fagopyrin are naphthodianthrones, anthraquinone-derivatives.

Applications

In the production of hydrogen peroxide

A large industrial application of anthraquinones is for the production of

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscous than water. It is used as an oxidizer, bleaching agent, and antiseptic, usually as a dilute solution (3 ...

. 2-Ethyl-9,10-anthraquinone or a related alkyl derivative is used, rather than anthraquinone itself. Riedl-Pfleiderer process

Millions of tons of hydrogen peroxide are manufactured by the

anthraquinone process The anthraquinone process is a process for the production of hydrogen peroxide, which was developed by BASF. The industrial production of hydrogen peroxide is based on the reduction of oxygen, as in the direct synthesis from the elements. Instead ...

Pulping

Sodium 2-anthraquinonesulfonate Sodium 2-anthraquinonesulfonate (AMS) is a water-soluble anthraquinone derivative. In the laboratory it could be prepared by sulfonation of anthraquinone. Digester additive in papermaking AMS is used as a catalyst in production of alkaline pulpi ...

(AMS) is a water-soluble anthraquinone derivative that was the first anthraquinone derivative discovered to have a catalytic effect in the alkaline pulping processes.

Dyestuff precursor

The 9,10-anthraquinone skeleton occurs in many dyes, such as

alizarin Alizarin (also known as 1,2-dihydroxyanthraquinone, Mordant Red 11, C.I. 58000, and Turkey Red) is an organic compound with formula that has been used throughout history as a prominent red dye, principally for dyeing textile fabrics. Historic ...

. Important derivatives of 9,10-anthraquinone are 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and the dinitroanthraquinone.

Medicine

Derivatives of 9,10-anthraquinone include many important drugs including the anthracenediones and the

anthracycline Anthracyclines are a class of drugs used in cancer chemotherapy that are extracted from ''Streptomyces'' bacterium. These compounds are used to treat many cancers, including leukemias, lymphomas, breast, stomach, uterine, ovarian, bladder canc ...

family of

chemotherapy Chemotherapy (often abbreviated to chemo and sometimes CTX or CTx) is a type of cancer treatment that uses one or more anti-cancer drugs (chemotherapeutic agents or alkylating agents) as part of a standardized chemotherapy regimen. Chemother ...

drugs. The latter drugs are derived from the bacterium ''

Streptomyces peucetius ''Streptomyces peucetius'' is a bacterium species in the genus ''Streptomyces''. ''S. peucetius'' produces the anthracycline antitumor antibiotics daunorubicin and doxorubicin Doxorubicin, sold under the brand name Adriamycin among others, ...

'', discovered in Italy a soil sample near the

Adriatic sea The Adriatic Sea () is a body of water separating the Italian Peninsula from the Balkan Peninsula. The Adriatic is the northernmost arm of the Mediterranean Sea, extending from the Strait of Otranto (where it connects to the Ionian Sea) to th ...

. Drugs in the anthraquinone family include the prototypical

daunorubicin Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically it is used for acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. I ...

doxorubicin Doxorubicin, sold under the brand name Adriamycin among others, is a chemotherapy medication used to treat cancer. This includes breast cancer, bladder cancer, Kaposi's sarcoma, lymphoma, and acute lymphocytic leukemia. It is often used toge ...

mitoxantrone Mitoxantrone (INN, BAN, USAN; also known as Mitozantrone in Australia; trade name Novantrone) is an anthracenedione antineoplastic agent. Uses Mitoxantrone is used to treat certain types of cancer, mostly acute myeloid leukemia. It improves th ...

, losoxantrone, and pixantrone. Most of these drugs, with the notable exception of pixantrone, are extremely cardiotoxic, causing irreversible

cardiomyopathy Cardiomyopathy is a group of diseases that affect the heart muscle. Early on there may be few or no symptoms. As the disease worsens, shortness of breath, feeling tired, and swelling of the legs may occur, due to the onset of heart failure. ...

, which can limit their practical usefulness in

cancer Cancer is a group of diseases involving abnormal cell growth with the potential to invade or spread to other parts of the body. These contrast with benign tumors, which do not spread. Possible signs and symptoms include a lump, abnormal b ...

treatment. The anthracenediones also include *

Antimalarial Antimalarial medications or simply antimalarials are a type of antiparasitic chemical agent, often naturally derived, that can be used to treat or to prevent malaria, in the latter case, most often aiming at two susceptible target groups, young ...

s such as

rufigallol Rufigallol or 1,2,3,5,6,7-hexahydroxy-9,10-anthraquinone is an organic compound with formula , which can be viewed as a derivative of anthraquinone through the replacement of six hydrogen atoms (H) by hydroxyl groups (OH). The compound is sol ...

*DNA dyes / nuclear counterstains such as DRAQ5, DRAQ7 and CyTRAK Orange for

flow cytometry Flow cytometry (FC) is a technique used to detect and measure physical and chemical characteristics of a population of cells or particles. In this process, a sample containing cells or particles is suspended in a fluid and injected into the flow ...

and

fluorescence microscopy A fluorescence microscope is an optical microscope that uses fluorescence instead of, or in addition to, scattering, reflection, and attenuation or absorption, to study the properties of organic or inorganic substances. "Fluorescence microscop ...

. *Anthraquinone derivatives:

rhein Rhein may refer to: Places * Rhine, a major river in Europe (german: Rhein, link=no) * Rhein, a village in the municipality of Morsbach in North Rhine-Westphalia, Germany * Rhein (Ostpreussen), a former name of the town Ryn in Poland Ships * SM ...

, emodin, aloe emodin, parietin (physcion), and

chrysophanol Chrysophanol, also known as chrysophanic acid, is a fungal isolate and a natural anthraquinone. It is a C-3 methyl substituted chrysazin of the trihydroxyanthraquinone family. Chrysophanol (other names; 1,8-dihydroxy-3-methyl-anthraquinone and c ...

extracted from '' Cassia occidentalis'' are toxic and known to cause hepatomyoencephalopathy in children. Aloe emodin

: Daunorubicin Mitoxantrone skeletal

Dantron,

emodin Emodin (6-methyl-1,3,8-trihydroxyanthraquinone) is a chemical compound, of the anthraquinone family, that can be isolated from rhubarb, buckthorn, and Japanese knotweed ('' Reynoutria japonica'' syn. ''Polygonum cuspidatum''). Emodin is particula ...

, and aloe emodin, and some of the

senna glycosides Senna glycoside, also known as sennoside or senna, is a medication used to treat constipation and empty the large intestine before surgery. The medication is taken by mouth or via the rectum. It typically begins working in around 30 minutes whe ...

have

laxative Laxatives, purgatives, or aperients are substances that loosen stools and increase bowel movements. They are used to treat and prevent constipation. Laxatives vary as to how they work and the side effects they may have. Certain stimulant, lubri ...

effects. Prolonged use and

abuse Abuse is the improper usage or treatment of a thing, often to unfairly or improperly gain benefit. Abuse can come in many forms, such as: physical or verbal maltreatment, injury, assault, violation, rape, unjust practices, crimes, or other t ...

leads to melanosis coli. 5 anthraquinones have been shown to inhibit the formation of Tau aggregates and dissolve paired helical filaments thought to be critical to Alzheimer's disease progression in both mouse models and in vitro testing but have not been investigated as a therapeutic agent.

References

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