Anacardic acids: Difference between revisions

[[:Anacardic acid general.svg|thumb|General structure of anacardic acids. R is an [[alkyl]] chain of variable length, which may be [[ |saturated or unsaturated.]]

'''Anacardic acids''' are [[phenolic lipid]]s, chemical compounds found in the shell of the cashew nut (''[[Anacardium occidentale]]''). An acid form of [[urushiol]], they also cause an allergic [[skin]] rash on contact,<ref name = "Rosen">{{cite journal | vauthors = Rosen T, Fordice DB | title = Cashew nut dermatitis | journal = Southern Medical Journal | volume = 87 | issue = 4 | pages = 543–546 | date = April 1994 | pmid = 8153790 | doi = 10.1097/00007611-199404000-00026 }}</ref> known as [[urushiol-induced contact dermatitis]]. Anacardic acid is a yellow liquid. It is partially miscible with ethanol and ether, but nearly immiscible with water. Chemically, anacardic acid is a mixture of several closely related [[organic compound]]s. Each consists of a [[salicylic acid]] substituted with an [[alkyl]] chain that has 15 or 17 carbon atoms. The alkyl group may be [[Saturated and unsaturated compounds|saturated or unsaturated]]; anacardic acid is a mixture of saturated and unsaturated molecules. The exact mixture depends on the species of the plant.<ref>{{cite journal | journal = Nature | volume = 174 | pages = 604 | year = 1954 | doi = 10.1038/174604a0 | title = Olefinic Nature of Anacardic Acid from Indian Cashew-nut Shell Liquid | vauthors = Paul VJ, Yeddanapalli LM | s2cid = 4249027 | issue = 4430 | bibcode = 1954Natur.174..604P | doi-access = free }}</ref> The 15-carbon unsaturated side chain compound found in the cashew plant is lethal to [[Gram-positive bacteria]].{{cn|date=September 2023}}

for [[tooth abscess]]es, it is also active against [[acne]], some insects, [[tuberculosis]], and [[MRSA]]. It is primarily found in foods such as [[cashew]] nuts, cashew apples, and [[cashew nutshell liquid|cashew nutshell oil]], but also in [[mango]]s and ''[[Pelargonium]]'' geraniums.<ref name=Romeo2006>{{Cite book | = Romeo | year = 2006 | title = Integrative plant biochemistry | pages = 132 | isbn = | publisher = Elsevier | location = Amsterdam }}</ref>

==Experimental antibacterial properties==

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|=Anacardic acid C153

| ImageFile=Anacardic acid C15-3.svg

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|=2--6-[(8''Z'',11''Z'')-pentadeca-8,11,14-trienyl]benzoic acid

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| CASNo=11034-77-8

| PubChem=9875131

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| ChEMBL = 455368

| SMILES=C=CCC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)C(=O)O

| MeSHName=anacardic+acid

|Section2={{Chembox Properties

| Formula=C₂₂H₃₀O₃

| MolarMass=342.4718 g/mol

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|Section3={{Chembox Hazards

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The side chain with three unsaturated bonds was the most active against ''[[Streptococcus mutans]]'', the tooth decay bacterium, in test tube experiments. The number of unsaturated bonds was not material against ''[[ acnes]]'', the acne bacterium.<ref> Kubo I, Muroi H, Himejima M 1993 Structure - Antibacterial activity relationships of anacardic acids Journal of Agricultural 41 .</ref> Eichbaum claims that one part to 200,000 to as as 2,000,000 is lethal to Grampositive bacteria in 15 minutes ''in vitro''. Somewhat higher ratios killed tubercle bacteria of [[tuberculosis]] in 30 minutes.<ref> Eichbaum FW 1946 Biological properties of anacardic acid (O- pentadeca dienylsalicylic acid) and related compounds. General discussion-bactericidal action. do Instituto 19 </ref> Heating these anacardic acids converts them to the alcohols ([[cardanol]]s), activity<ref>Himejima M Kubo I 1991 Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nutshell oil Journal of Agricultural Food .<ref> Patel NM Patel MS 1936 Cashew-nut shell oil and a study of the changes produced in the oil by the action of heat. Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences, Medicine 5 </ref> It is said that the people of the [[Gold Coast (region)|Gold Coast]] use cashew leaves and bark for a toothache.<ref>http://www.hort.purdue.edu/newcrop/duke_energy/Anacardium_occidentale.html#Folk%20Medicine Cashew plants in folk medicine.</ref>

Anacardic acid is the main component of [[cashew nutshell liquid]] (CNSL), and finds use in the chemical industry for the production of [[cardanol]], which is used for resins, coatings, and frictional materials. Cardanol is used to make [[phenalkamine]]s, which are used as curing agents for the durable epoxy coatings used on concrete floors.<ref name=cen>{{cite journal|title=A Nutty Chemical |date=September 8, 2008 |volume=86 |issue=36 |pages=26–27 | Tullo |journal=[[Chemical and Engineering News]]}}</ref>

The first chemical analysis of the oil of the cashew nut shell from the ''Anacardium occidentale'' was published in 1847.<ref>{{cite journal

Anacardic acid is synergistic with [[anethole]] from the seed of [[anise]] ([[Umbelliferae]]) and [[linalool]] from green tea ''[[in vitro]]'' [Muroi & Kubo, p1782]. The [[totarol]] in the bark of [[Podocarpus]] trees is synergistic with anacardic acid in its bactericidal effects.<ref>doi10.1021/np50088a008</ref>

There is also a suspicion that inhibiting anacardic acids may arrest the growth of cancer tumors such as [[breast cancer]]. [Kubo et al., 1993] Inhibition of [[Lysine N-acetyltransferase|lysine acetyltransferase]] by anacardic acid was shown to make cancer cells using [[Alternative Lengthening of Telomeres|alternative lengthening of telomeres]] more sensitive to [[Radiation therapy|radiation]].<ref>{{cite journal | vauthors = Bakhos-Douaihy D, Desmaze C, Jeitany M, Gauthier LR, Biard D, Junier MP, Chneiweiss H, Boussin FD | display-authors = 6 | title = ALT cancer cells are specifically sensitive to lysine acetyl transferase inhibition | journal = Oncotarget | volume = 10 | issue = 7 | pages = 773–784 | date = January 2019 | pmid = 30774779 | pmc = 6366824 | doi = 10.18632/oncotarget.26616 }}</ref>

Anacardic acid (2-hydroxy-6-alkylbenzoic acid) provides resistance to small pest insects ([[aphids]] and [[spider mites]]).<ref> Bioactivity of against (Leptinotarsa decemlineata) </ref>

Anacardic acid kills [[]] cells more rapidly than [[totarol]].<ref> , Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus</ref>

==List of anacardic acids==

* [[6-pentadecyl salicylic acid]] (6-PDSA), a potent HAT inhibitor from [[cashew nut]] shell liquid, and sensitizer of cancer cells to [[ionizing radiation]].<ref name="dietaryncbi">{{cite journal | vauthors = Rajendran P, Ho E, Williams DE, Dashwood RH | title = Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells | journal = Clinical Epigenetics | volume = 3 | issue = 1 | pages = 4 | year = 2011 | pmid = 22247744 | pmc = 3255482 | doi = 10.1186/1868-7083-3-4 | doi-access = free }}</ref>

==See also==

==References==

{{reflist|}}

[[Category:Phenolic lipids]]

[[Category:Histone Acetyltransferase Inhibitor]]

[[Category:Plant toxins]]