Aloe emodin

Last updated
Aloe emodin
Aloe emodin.svg
Clinical data
Other namesRhabarberone
Routes of
administration
Oral
ATC code
  • None
Identifiers
  • 1,8-Dihydroxy-3-(hydroxymethyl)-9,10-anthracenedione
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.884 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C15H10O5
Molar mass 270.240 g·mol−1
3D model (JSmol)
Melting point 223 to 224 °C (433 to 435 °F) Sublimes in CO2 stream
  • O=C2c1cccc(O)c1C(=O)c3c2cc(cc3O)CO
  • InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)15(20)12-8(14(9)19)2-1-3-10(12)17/h1-5,16-18H,6H2 Yes check.svgY
  • Key:YDQWDHRMZQUTBA-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Aloe emodin (1,8-dihydroxy-3-(hydroxymethyl)anthraquinone) is an anthraquinone and an isomer of emodin present in aloe latex, an exudate from the aloe plant. It has a strong stimulant-laxative action. [1] Aloe emodin is not carcinogenic when applied to the skin, although it may increase the carcinogenicity of some kinds of radiation. [2] [3]

Aloe emodin is found in the gel, sap or leaves of aloe vera, the socotrine aloe, Barbados aloe, and Zanzibar aloes, the bark of Frangula ( Rhamnus frangula ) and cascara sagrada ( Rhamnus purshiana ), the leaves of Senna ( Cassia angustifolia ), and the rhizome of rhubarb ( Rheum rhaponticum ).[ citation needed ] Aloe-emodin has not been found in Natal aloes.[ citation needed ]

Related Research Articles

<i>Aloe</i> Genus of succulent flowering plants

Aloe is a genus containing over 650 species of flowering succulent plants. The most widely known species is Aloe vera, or "true aloe". It is called this because it is cultivated as the standard source for assorted pharmaceutical purposes. Other species, such as Aloe ferox, are also cultivated or harvested from the wild for similar applications.

<span class="mw-page-title-main">Carcinogen</span> Substance, radionuclide, or radiation directly involved in causing cancer

A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substances are considered carcinogens, but their carcinogenic activity is attributed to the radiation, for example gamma rays and alpha particles, which they emit. Common examples of non-radioactive carcinogens are inhaled asbestos, certain dioxins, and tobacco smoke. Although the public generally associates carcinogenicity with synthetic chemicals, it is equally likely to arise from both natural and synthetic substances. Carcinogens are not necessarily immediately toxic; thus, their effect can be insidious.

<span class="mw-page-title-main">Mutagen</span> Physical or chemical agent that increases the rate of genetic mutation

In genetics, a mutagen is a physical or chemical agent that permanently changes genetic material, usually DNA, in an organism and thus increases the frequency of mutations above the natural background level. As many mutations can cause cancer in animals, such mutagens can therefore be carcinogens, although not all necessarily are. All mutagens have characteristic mutational signatures with some chemicals becoming mutagenic through cellular processes.

Benzo(<i>a</i>)pyrene Carcinogenic compound found in smoke and soot

Benzo[a]pyrene (BaP or B[a]P) is a polycyclic aromatic hydrocarbon and the result of incomplete combustion of organic matter at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F). The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats. The substance with the formula C20H12 is one of the benzopyrenes, formed by a benzene ring fused to pyrene. Its diol epoxide metabolites (more commonly known as BPDE) react with and bind to DNA, resulting in mutations and eventually cancer. It is listed as a Group 1 carcinogen by the IARC. In the 18th century a scrotal cancer of chimney sweepers, the chimney sweeps' carcinoma, was already known to be connected to soot.

<i>Aloe vera</i> Species of plant

Aloe vera is a succulent plant species of the genus Aloe. It is widely distributed, and is considered an invasive species in many world regions.

<i>Frangula californica</i> Species of tree

Frangula californica is a species of flowering plant in the buckthorn family native to western North America. It produces edible fruits and seeds. It is commonly known as California coffeeberry and California buckthorn.

<span class="mw-page-title-main">Anthrone</span> Chemical compound

Anthrone is a tricyclic aromatic ketone. It is used for a common cellulose assay and in the colorimetric determination of carbohydrates.

<i>Frangula purshiana</i> Species of buckhorn shrub

Frangula purshiana is a species of plant in the family Rhamnaceae. It is native to western North America from southern British Columbia south to central California, and eastward to northwestern Montana.

<span class="mw-page-title-main">Anthraquinones</span>

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

<span class="mw-page-title-main">Benzethonium chloride</span> Chemical compound

Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties, and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.

<span class="mw-page-title-main">Emodin</span> Chemical compound

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. Emodin is particularly abundant in the roots of the Chinese rhubarb, knotweed and knotgrass as well as Hawaii ‘au‘auko‘i cassia seeds or coffee weed. It is specifically isolated from Rheum palmatum L. It is also produced by many species of fungi, including members of the genera Aspergillus, Pyrenochaeta, and Pestalotiopsis, inter alia. The common name is derived from Rheum emodi, a taxonomic synonym of Rheum australe, and synonyms include emodol, frangula emodin, rheum emodin, 3-methyl-1,6,8-trihydroxyanthraquinone, Schüttgelb (Schuttgelb), and Persian Berry Lake.

<i>Rhamnus cathartica</i> Species of flowering plant in the buckthorn family Rhamnaceae

Rhamnus cathartica, the European buckthorn, common buckthorn, purging buckthorn, or just buckthorn, is a species of small tree in the flowering plant family Rhamnaceae. It is native to Europe, northwest Africa and western Asia, from the central British Isles south to Morocco, and east to Kyrgyzstan. It was introduced to North America as an ornamental shrub in the early 19th century or perhaps before, and is now naturalized in the northern half of the continent, and is classified as an invasive plant in several US states and in Ontario, Canada.

<i>Frangula alnus</i> Species of flowering plant in the family Rhamnaceae

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, northernmost Africa, and western Asia, from Ireland and Great Britain north to the 68th parallel in Scandinavia, east to central Siberia and Xinjiang in western China, and south to northern Morocco, Turkey, and the Alborz in Iran and the Caucasus Mountains; in the northwest of its range, it is rare and scattered. It is also introduced and naturalised in eastern North America.

<span class="mw-page-title-main">Aloin</span> Chemical compound

Aloin, also known as barbaloin, is a bitter, yellow-brown colored compound noted in the exudate of at least 68 Aloe species at levels from 0.1 to 6.6% of leaf dry weight, and in another 17 species at indeterminate levels [Reynolds, 1995b]. It is used as a stimulant-laxative, treating constipation by inducing bowel movements. The compound is present in what is commonly referred to as the aloe latex that exudes from cells adjacent to the vascular bundles, found under the rind of the leaf and in between it and the gel. When dried, it has been used as a bittering agent in commerce [21 CFR 172.510. Scientific names given include Aloe perryi, A. barbadensis, A. ferox, and hybrids of A. ferox with A. africana and A. spicata.]. Aloe is listed in federal regulations as a natural substance that may be "safely used in food" when used "in the minimum quantity required to produce their intended physical or technical effect and in accordance with all the principles of good manufacturing practice." This food application is generally limited to use in quite small quantities as a flavoring in alcoholic beverages and may usually be identified only as a "natural flavor."

<span class="mw-page-title-main">Formaldehyde releaser</span> Chemical compound used as a preservative that slowly releases formaldehyde.

A formaldehyde releaser, formaldehyde donor or formaldehyde-releasing preservative is a chemical compound that slowly releases formaldehyde. Formaldehyde-releasers are added to prevent microbial growth and extend shelf life. The intent of these compounds is that they release formaldehyde at levels that suppress microbial growth but sufficiently low to not threaten humans. The use of these chemicals in cosmetics has elicited controversy.

<span class="mw-page-title-main">Sunburn</span> Burning of the skin by the suns radiation

Sunburn is a form of radiation burn that affects living tissue, such as skin, that results from an overexposure to ultraviolet (UV) radiation, usually from the sun. Common symptoms in humans and other animals include red or reddish skin that is hot to the touch or painful, general fatigue, and mild dizziness. Other symptoms include blistering, peeling skin, swelling, itching, and nausea. Excessive UV radiation is the leading cause of (primarily) non-malignant skin tumors, which in extreme cases can be life-threatening. Sunburn is an inflammatory response in the tissue triggered by direct DNA damage by UV radiation. When the cells' DNA is overly damaged by UV radiation, type I cell-death is triggered and the tissue is replaced.

A co-carcinogen is a chemical that promotes the effects of a carcinogen in the production of cancer. Usually, the term is used to refer to chemicals that are not carcinogenic on their own, such that an equivalent amount of the chemical is insufficient to initiate carcinogenesis. A chemical can be co-carcinogenic with other chemicals or with nonchemical carcinogens, such as UV radiation.

<i>Frangula caroliniana</i> Species of flowering plant in the buckthorn family Rhamnaceae

Frangula caroliniana, commonly called the Carolina buckthorn, is a deciduous upright shrub or small tree native to the southeastern, south-central, and mid-western parts of the United States, from Texas east to Florida and north as far as Maryland, Ohio, Missouri, and Oklahoma. There is also an isolated population in the State of Nuevo León in northeastern Mexico. It is found in a wide variety of habitats, including barrens, forests, and limestone bluffs.

<span class="mw-page-title-main">Health effects of sunlight exposure</span>

Exposing skin to the ultraviolet radiation in sunlight has both positive and negative health effects. On the positive side, exposure allows for the synthesis of vitamin D3. Vitamin D has been suggested as having a wide range of positive health effects, which include strengthening bones and possibly inhibiting the growth of some cancers. A dietary supplement can also supply vitamin D, but there are also benefits to exposure not obtainable through Vitamin D supplementation. Long-term sun exposure is associated with reduced all-cause mortality and reduced mortality risk from cardiovascular disease (CVD), some forms of cancer, and non-CVD/noncancer related disease, with indications in these studies that Vitamin D is not the mediator. Supplementation offers limited bioavailability and no synthesis of subdermal nitric oxide. UV exposure also has positive effects for endorphin levels, and possibly for protection against multiple sclerosis. Abundant visible light to the eyes gives health benefits through its association with the timing of melatonin synthesis, maintenance of normal and robust circadian rhythms, and reduced risk of seasonal affective disorder.

<span class="mw-page-title-main">Aloeae</span> Tribe of succulent plants

Aloeae is a tribe of succulent plants in the subfamily Asphodeloideae of the family Asphodelaceae, consisting of the aloes and their close relatives. The taxon may also be treated as the subfamily Alooideae by those botanists who retain the narrower circumscription of Asphodelaceae adopted prior to the APG III system. Typically, plants have rosettes of more or less succulent leaves, with or without a distinct stem. Their flowers are arranged in racemes and tend to be either small and pale, pollinated by insects, or larger and more brightly coloured, pollinated by birds. As of 2017, 11 genera are recognized, most created since 2010 by splitting off another five genera from Aloe and another two from Haworthia. Only two genera, Aloe and Aloidendron, are native outside southern Africa, extending northwards to the Arabian Peninsula. Seven genera are restricted to South Africa, some with small ranges. Members of the Aloeae are cultivated by succulent plant enthusiasts; Aloe species especially are used in temperate climates as ornamental garden plants. Some species are used in traditional medicine. Aloe vera and Aloe ferox are cultivated for their extracts, whose uses include moisturizers and emollients in cosmetics.

References

  1. The Merck Index (12th ed.). p. 313.
  2. Badgwell DB, Walker CM, Baker WT, Strickland FM (March 2004). "Ethanol and aloe emodin alter the p53 mutational spectrum in ultraviolet radiation-induced murine skin tumors". Molecular Carcinogenesis. 39 (3): 127–38. doi:10.1002/mc.10170. PMID   14991742. S2CID   24146785.
  3. National Toxicology Program (September 2010). "Photocarcinogenesis study of aloe vera [CAS NO. 481-72-1(Aloe-emodin)] in SKH-1 mice (simulated solar light and topical application study)". National Toxicology Program Technical Report Series (553): 7–33, 35–97, 99-103 passim. PMID   21031007.

See also