Anacardic acids

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

Anacardic acids are phenolic lipids, 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, [1] 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 compounds. Each consists of a salicylic acid substituted with an alkyl chain that has 15 or 17 carbon atoms. The alkyl group may be saturated or unsaturated; anacardic acid is a mixture of saturated and unsaturated molecules. The exact mixture depends on the species of the plant. [2] The 15-carbon unsaturated side chain compound found in the cashew plant is lethal to Gram-positive bacteria.[ citation needed ]

Contents

Folk use for tooth abscesses, 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 oil, but also in mangos and Pelargonium geraniums. [3]

Experimental antibacterial properties

Anacardic acid (C15:3, all-Z, major component)
Anacardic acid C15-3.svg
Names
Preferred IUPAC name
2-Hydroxy-6-[(8Z,11Z)-pentadeca-8,11,14-trienyl]benzoic acid
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.031.141 OOjs UI icon edit-ltr-progressive.svg
MeSH anacardic+acid
PubChem CID
  • C=CCC=CCC=CCCCCCCCC1=C(C(=CC=C1)O)C(=O)O
Properties
C22H30O3
Molar mass 342.4718 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 Cutibacterium acnes , the acne bacterium. [4] Eichbaum claims that a solution of one part anacardic acid to 200,000 parts water to as low as one part in 2,000,000 is lethal to Gram-positive bacteria in 15 minutes in vitro. Somewhat higher ratios killed tubercle bacteria of tuberculosis in 30 minutes. [5] Heating these anacardic acids converts them to the alcohols (cardanols) with reduced activity compared to the acids. Decarboxylation, such as through heating done in most commercial oil processing, results in compounds with significantly reduced activity. [6] [7] It is said that the people of the Gold Coast (now Ghana) use cashew leaves and bark for a toothache. [8]

Industrial uses

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 phenalkamines, which are used as curing agents for the durable epoxy coatings used on concrete floors. [9]

History

The first chemical analysis of the oil of the cashew nut shell from the Anacardium occidentale was published in 1847. [10] It was later found to be a mixture rather than one chemical, sometimes the plural anacardic acids is used.[ citation needed ]

Synergies

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. [11]

Other and potential uses

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 acetyltransferase by anacardic acid was shown to make cancer cells using alternative lengthening of telomeres more sensitive to radiation. [12]

Anacardic acid (2-hydroxy-6-alkylbenzoic acid) provides resistance to small pest insects (aphids and spider mites). [13]

Anacardic acid kills methicillin-resistant Staphylococcus aureus (MRSA) cells more rapidly than totarol. [14]

List of anacardic acids

See also

Related Research Articles

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<span class="mw-page-title-main">Cashew</span> Species of flowering plant in the family Anacardiaceae

The cashew tree is a tropical evergreen tree native to South America in the genus Anacardium that produces the cashew seed and the cashew apple accessory fruit. The tree can grow as tall as 14 metres, but the dwarf cultivars, growing up to 6 m (20 ft), prove more profitable, with earlier maturity and greater yields. The cashew seed is commonly considered a snack nut eaten on its own, used in recipes, or processed into cashew cheese or cashew butter. Like the tree, the nut is often simply called a cashew. Cashew allergies are triggered by the proteins found in tree nuts, and cooking often does not remove or change these proteins.

<i>Anacardium</i> Genus of flowering plants

Anacardium, the cashews, are a genus of flowering plants in the family Anacardiaceae, native to tropical regions of the Americas. The best known species is Anacardium occidentale, which is commercially cultivated for its cashew nuts and cashew apples.

<span class="mw-page-title-main">Accessory fruit</span> Botanical category of fruit

An accessory fruit is a fruit that contains tissue derived from plant parts other than the ovary. In other words, the flesh of the fruit develops not from the floral ovary, but from some adjacent tissue exterior to the carpel. As a general rule, the accessory fruit is a combination of several floral organs, including the ovary. In contrast, true fruit forms exclusively from the ovary of the flower.

<span class="mw-page-title-main">Nut (fruit)</span> In botany, type of dry indehiscent fruit

A nut is a fruit consisting of a hard or tough nutshell protecting a kernel which is usually edible. In general usage and in a culinary sense, a wide variety of dry seeds are called nuts, but in a botanical context "nut" implies that the shell does not open to release the seed (indehiscent).

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

Cinnamaldehyde is an organic compound with the formula or C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

<i>Cutibacterium acnes</i> Species of bacterium

Cutibacterium acnes is the relatively slow-growing, typically aerotolerant anaerobic, gram-positive bacterium (rod) linked to the skin condition of acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. Its genome has been sequenced and a study has shown several genes can generate enzymes for degrading skin and proteins that may be immunogenic.

<i>Nigella</i> Genus of annual plants

Nigella is a genus of 18 species of annual plants in the family Ranunculaceae, native to Southern Europe, North Africa, South Asia, Southwest Asia and Middle East. Common names applied to members of this genus are nigella, devil-in-a-bush or love-in-a-mist.

<span class="mw-page-title-main">4-Hydroxynonenal</span> Chemical compound

4-Hydroxynonenal, or 4-hydroxy-2-nonenal or 4-HNE or HNE,, is an α,β-unsaturated hydroxyalkenal that is produced by lipid peroxidation in cells. 4-HNE is the primary α,β-unsaturated hydroxyalkenal formed in this process. It is a colorless oil. It is found throughout animal tissues, and in higher quantities during oxidative stress due to the increase in the lipid peroxidation chain reaction, due to the increase in stress events. 4-HNE has been hypothesized to play a key role in cell signal transduction, in a variety of pathways from cell cycle events to cellular adhesion.

<span class="mw-page-title-main">Heterocyclic amine</span> Any heterocyclic compound having at least one nitrogen heteroatom

Heterocyclic amines, also sometimes referred to as HCAs, are chemical compounds containing at least one heterocyclic ring, which by definition has atoms of at least two different elements, as well as at least one amine (nitrogen-containing) group. Typically it is a nitrogen atom of an amine group that also makes the ring heterocyclic, though compounds exist in which this is not the case. The biological functions of heterocyclic amines vary, including vitamins and carcinogens. Carcinogenic heterocyclic amines are created by high temperature cooking of meat and smoking of plant matter like tobacco. Some well known heterocyclic amines are niacin, nicotine, and the nucleobases that encode genetic information in DNA.

<i>Semecarpus anacardium</i> Species of tree

Semecarpus anacardium, commonly known as the marking nut tree, Malacca bean tree, marany nut, oriental cashew, phobi nut tree and varnish tree, is a native of India, found in the outer Himalayas to the Coromandel Coast. It is closely related to the cashew.

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

Polygodial is chemical compound found in dorrigo pepper, mountain pepper, horopito, canelo, paracress, water-pepper, and Dendrodoris limbata.

<span class="mw-page-title-main">Cardanol</span> Phenolic lipid

Cardanol is a phenolic lipid obtained from anacardic acid, the main component of cashew nutshell liquid (CNSL), a byproduct of cashew nut processing. Cardanol finds use in the chemical industry in resins, coatings, frictional materials, and surfactants used as pigment dispersants for water-based inks. It is used to make phenalkamines, which are used as curing agents for the durable epoxy coatings used on concrete floors. The name of the substance is derived by contraction from the genus Anacardium, which includes the cashew tree, Anacardium occidentale. The name of the genus itself is based on the Greek word for heart.

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

Vulpinic acid is a natural product first found in and important in the symbiosis underlying the biology of lichens. It is a simple methyl ester derivative of its parent compound, pulvinic acid, and a close relative of pulvinone, both of which derive from aromatic amino acids such as phenylalanine via secondary metabolism. The roles of vulpinic acid are not fully established, but may include properties that make it an antifeedant for herbivores. The compound is relatively toxic to mammals.

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

Leucopelargonidin is a colorless chemical compound related to leucoanthocyanins. It can be found in Albizia lebbeck, in the fruit of Anacardium occidentale (Cashew), in the fruit of Areca catechu, in the fruit of Hydnocarpus wightiana, in the rhizome of Rumex hymenosepalus, in Zea mays (Corn) and in Ziziphus jujuba.

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

Totarol is a naturally produced diterpene that is bioactive as totarol. It was first isolated by McDowell and Easterfield from the heartwood of Podocarpus totara, a conifer tree found in New Zealand. Podocarpus totara was investigated for unique molecules due to the tree's increased resistance to rotting. Recent studies have confirmed totarol's unique antimicrobial and therapeutic properties. Consequently, totarol is a candidate for a new source of drugs and has been the goal of numerous syntheses.

In natura is a phrase to describe conditions present in a non-laboratory environment, to differentiate it from in vivo and ex vivo conditions.

Anacardium othonianum is a tree native from the tropical savanna (cerrado) region of Brazil, whose fruit is similar to that of the common cashew tree of the Brazilian Northeast. It is locally known by the Tupi-derived name cajuí, and by the Portuguese names caju-de-árvore-do-cerrado, caju-vermelho-de-goiás, cajuzinho-do-cerrado or just cajuzinho.

Adipostatin A is an alkylresorcinol, a type of phenolic lipids composed of long aliphatic chains and phenolic rings. Chemically, it is similar in structure to urushiol, the irritant found in poison ivy.

<span class="mw-page-title-main">1-Pentadecanol</span> 15-carbon alcohol

1-Pentadecanol is an organic chemical compound classified as an alcohol. At room temperature, it is a white, flaky solid. It is a saturated long-chain fatty alcohol consisting of a pentadecane chain with a hydroxy group as substituent on one end. It is an achiral molecule.

References

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