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)
ChEBI
ChEMBL
ChemSpider
MeSH anacardic+acid
PubChem CID
UNII
  • InChI=1S/C22H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(23)21(19)22(24)25/h2,4-5,7-8,15,17-18,23H,1,3,6,9-14,16H2,(H,24,25)/b5-4-,8-7-
    Key: QUVGEKPNSCFQIR-UTOQUPLUSA-N
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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

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

Cashew is the common name of a tropical evergreen tree Anacardium occidentale, in the family Anacardiaceae. It is native to South America and is the source of the cashew nut and the cashew apple, an 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 nut is edible and is eaten on its own as a snack, used in recipes, or processed into cashew cheese or cashew butter. The nut is often simply called a 'cashew'.

<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">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. It is an essential oil. The bark of cinnamon tree contains high concentrations of cinnamaldehyde.

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

4-Hydroxynonenal, or 4-hydroxy-2E-nonenal 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.

Autoxidation refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organic compounds in air at ambient temperatures. Many common phenomena can be attributed to autoxidation, such as food going rancid, the 'drying' of varnishes and paints, and the perishing of rubber. It is also an important concept in both industrial chemistry and biology. Autoxidation is therefore a fairly broad term and can encompass examples of photooxygenation and catalytic oxidation.

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

Diallyl disulfide is an organosulfur compound derived from garlic and a few other plants in the genus Allium. Along with diallyl trisulfide and diallyl tetrasulfide, it is one of the principal components of the distilled oil of garlic. It is a yellowish liquid which is insoluble in water and has a strong garlic odor. It is produced during the decomposition of allicin, which is released upon crushing garlic and other plants of the family Alliaceae. Diallyl disulfide has many of the health benefits of garlic, but it is also an allergen causing garlic allergy. Highly diluted, it is used as a flavoring in food. It decomposes in the human body into other compounds such as allyl methyl sulfide.

<span class="mw-page-title-main">Macadamia oil</span> Non-volatile oil expressed from the nut meat of the macadamia

Macadamia oil, also known as macadamia nut oil, is a non-volatile oil extracted from the nuts of the macadamia tree, indigenous to Australia. This oil is used in culinary applications as a frying or salad oil, and in cosmetics for its emollient properties and as a fragrance fixative.

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

Semecarpus anacardium, commonly known as the marking nut tree, Malacca bean tree, marany nut, oriental cashew, dhobi 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.

γ-Valerolactone Chemical compound

γ-Valerolactone (GVL) or gamma-valerolactone is an organic compound with the formula C5H8O2. This colourless liquid is one of the more common lactones. GVL is chiral but is usually used as the racemate. It is readily obtained from cellulosic biomass and is a potential fuel and green solvent.

<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.

The molecular formula C22H30O3 (molar mass : 342.47 g/mol) may refer to:

<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 wightianus, 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

  1. ↑ Rosen T, Fordice DB (April 1994). "Cashew nut dermatitis". Southern Medical Journal. 87 (4): 543–546. doi:10.1097/00007611-199404000-00026. PMID   8153790.
  2. ↑ Paul VJ, Yeddanapalli LM (1954). "Olefinic Nature of Anacardic Acid from Indian Cashew-nut Shell Liquid". Nature. 174 (4430): 604. Bibcode:1954Natur.174..604P. doi: 10.1038/174604a0 . S2CID   4249027.
  3. ↑ Romeo JT, ed. (2006). Integrative plant biochemistry. Amsterdam: Elsevier. p. 132. ISBN   978-0-08-045125-1.
  4. ↑ Kubo I, Muroi H, Himejima M (1993). "Structure - Antibacterial activity relationships of anacardic acids". Journal of Agricultural and Food Chemistry. 41 (6): 1016–1019 [1018]. doi:10.1021/jf00030a036.
  5. ↑ Eichbaum FW (1946). "Biological properties of anacardic acid (O- pentadeca dienylsalicylic acid) and related compounds. General discussion-bactericidal action". Memórias do Instituto Butantan. 19: 71–86.
  6. ↑ Himejima M, Kubo I (1991). "Antibacterial agents from the cashew Anacardium occidentale (Anacardiaceae) nutshell oil". Journal of Agricultural and Food Chemistry. 39 (2): 418–421 [419]. doi:10.1021/jf00002a039.
  7. ↑ 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 (pt 2): 114–131.
  8. ↑ Duke JA (1983). "Cashew plants in folk medicine". Handbook of Energy Crops. unpublished. Horticulture & Landscape Architecture, Purdue University.
  9. ↑ Tullo AH (September 8, 2008). "A Nutty Chemical". Chemical and Engineering News . 86 (36): 26–27. doi:10.1021/cen-v086n033.p026.
  10. ↑ Städeler J (1847). "Ueber die eigenthümlichen Bestandtheile der Anacardiumfrüchte". Annalen der Chemie und Pharmacie. 63 (2): 137–164. doi:10.1002/jlac.18470630202.
  11. ↑ Kubo I, Muroi H, Himejima M (October 1992). "Antibacterial activity of totarol and its potentiation". Journal of Natural Products. 55 (10): 1436–1440. doi:10.1021/np50088a008. PMID   1453180.
  12. ↑ Bakhos-Douaihy D, Desmaze C, Jeitany M, Gauthier LR, Biard D, Junier MP, et al. (January 2019). "ALT cancer cells are specifically sensitive to lysine acetyl transferase inhibition". Oncotarget. 10 (7): 773–784. doi:10.18632/oncotarget.26616. PMC   6366824 . PMID   30774779.
  13. ↑ Schultz DJ, Olsen C, Cobbs GA, Stolowich NJ, Parrott MM (October 2006). "Bioactivity of anacardic acid against colorado potato beetle (Leptinotarsa decemlineata) larvae". Journal of Agricultural and Food Chemistry. 54 (20): 7522–7529. doi:10.1021/jf061481u. PMID   17002417.
  14. ↑ Muroi H, Kubo I (April 1996). "Antibacterial activity of anacardic acid and totarol, alone and in combination with methicillin, against methicillin-resistant Staphylococcus aureus". The Journal of Applied Bacteriology. 80 (4): 387–394. doi:10.1111/j.1365-2672.1996.tb03233.x. PMID   8849640.
  15. ↑ Rajendran P, Ho E, Williams DE, Dashwood RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clinical Epigenetics. 3 (1): 4. doi: 10.1186/1868-7083-3-4 . PMC   3255482 . PMID   22247744.
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