Anziaic acid

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Anziaic acid
Anziaic acid.svg
Names
IUPAC name
4-(2,4-Dihydroxy-6-pentylbenzoyl)oxy-2-hydroxy-6-pentylbenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C24H30O7/c1-3-5-7-9-15-11-17(25)13-19(26)22(15)24(30)31-18-12-16(10-8-6-4-2)21(23(28)29)20(27)14-18/h11-14,25-27H,3-10H2,1-2H3,(H,28,29)
    Key: BEFYPHLCGVCBFF-UHFFFAOYSA-N
  • CCCCCC1=C(C(=CC(=C1)O)O)C(=O)OC2=CC(=C(C(=C2)O)C(=O)O)CCCCC
Properties
C24H30O7
Molar mass 430.5 g/mol
Melting point 122 °C (252 °F; 395 K) dec
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Anziaic acid is a depside found in lichens. It gives a red reaction in the C test. The two phenolic rings have a pentyl side chain. It is an ester dimer of olivetolic acid. [1]

Contents

Anziaic acid works as an antibacterial compound by inhibiting topoisomerase. [2] [3]

Production

Anziaic acid has been artificially produced from olivetolic acid by benzylation of the O-phenol positions, and then condensing with trifluoroacetic anhydride. [1]

Properties

Anziaic acid is colourless. It can be dissolved in ethanol, ethanol-water mixture, or cyclohexane-benzene mixture. [1]

Perlatolic acid, dihydropicrolichenic acid, 2'-O-methylanziaic acid, 2-O-methylperlatolic acid, 2'-O-methylperlatolic and planaic acid are derivatives of anziaic acid, where a methyl group replaces a hydrogen in some of the hydroxy positions on the rings. [1]

Occurrence

Anziaic acid is found in Parmeliaceae including Hypotrachyna , [2] Stereocaulon , [4] and Cetrelia , [5]

Related Research Articles

<span class="mw-page-title-main">Parmeliaceae</span> Family of lichens

The Parmeliaceae is a large and diverse family of Lecanoromycetes. With over 2700 species in 71 genera, it is the largest family of lichen-forming fungi. The most speciose genera in the family are the well-known groups: Xanthoparmelia, Usnea, Parmotrema, and Hypotrachyna.

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

The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidized, and the hydrogen peroxide is reduced.

<span class="mw-page-title-main">11β-Hydroxysteroid dehydrogenase type 1</span> Mammalian protein found in Homo sapiens

11β-Hydroxysteroid dehydrogenase type 1, also known as cortisone reductase, is an NADPH-dependent enzyme highly expressed in key metabolic tissues including liver, adipose tissue, and the central nervous system. In these tissues, HSD11B1 reduces cortisone to the active hormone cortisol that activates glucocorticoid receptors. It belongs to the family of short-chain dehydrogenases. It is encoded by the HSD11B1 gene.

Topoisomerase inhibitors are chemical compounds that block the action of topoisomerases, which are broken into two broad subtypes: type I topoisomerases (TopI) and type II topoisomerases (TopII). Topoisomerase plays important roles in cellular reproduction and DNA organization, as they mediate the cleavage of single and double stranded DNA to relax supercoils, untangle catenanes, and condense chromosomes in eukaryotic cells. Topoisomerase inhibitors influence these essential cellular processes. Some topoisomerase inhibitors prevent topoisomerases from performing DNA strand breaks while others, deemed topoisomerase poisons, associate with topoisomerase-DNA complexes and prevent the re-ligation step of the topoisomerase mechanism. These topoisomerase-DNA-inhibitor complexes are cytotoxic agents, as the un-repaired single- and double stranded DNA breaks they cause can lead to apoptosis and cell death. Because of this ability to induce apoptosis, topoisomerase inhibitors have gained interest as therapeutics against infectious and cancerous cells.

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

Camptothecin (CPT) is a topoisomerase inhibitor. It was discovered in 1966 by M. E. Wall and M. C. Wani in systematic screening of natural products for anticancer drugs. It was isolated from the bark and stem of Camptotheca acuminata, a tree native to China used in traditional Chinese medicine. It has been used clinically more recently in China for the treatment of gastrointestinal tumors. CPT showed anticancer activity in preliminary clinical trials, especially against breast, ovarian, colon, lung, and stomach cancers. However, it has low solubility and adverse effects have been reported when used therapeutically, so synthetic and medicinal chemists have developed numerous syntheses of camptothecin and various derivatives to increase the benefits of the chemical, with good results. Four CPT analogues have been approved and are used in cancer chemotherapy today, topotecan, irinotecan, belotecan, and trastuzumab deruxtecan. Camptothecin has also been found in other plants including Chonemorpha fragrans.

<span class="mw-page-title-main">TOP1</span> DNA topoisomerase enzyme

DNA topoisomerase 1 is an enzyme that in humans is encoded by the TOP1 gene. It is a DNA topoisomerase, an enzyme that catalyzes the transient breaking and rejoining of a single strand of DNA.

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

A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, Lamiaceae, Papaveraceae and Myrtaceae.

<i>Punctelia</i> Genus of lichen

Punctelia is a genus of foliose lichens belonging to the large family Parmeliaceae. The genus, which contains about 50 species, was segregated from genus Parmelia in 1982. Characteristics that define Punctelia include the presence of hook-like to thread-like conidia, simple rhizines, and point-like pseudocyphellae. It is this last feature that is alluded to in the vernacular names speckled shield lichens or speckleback lichens.

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

Olivetol, also known as 5-pentylresorcinol or 5-pentyl-1,3-benzenediol, is an organic compound found in certain species of lichen; it is also a precursor in various syntheses of tetrahydrocannabinol.

<span class="mw-page-title-main">Naturally occurring phenols</span> Group of chemical compounds

In biochemistry, naturally occurring phenols are natural products containing at least one phenol functional group. Phenolic compounds are produced by plants and microorganisms. Organisms sometimes synthesize phenolic compounds in response to ecological pressures such as pathogen and insect attack, UV radiation and wounding. As they are present in food consumed in human diets and in plants used in traditional medicine of several cultures, their role in human health and disease is a subject of research. Some phenols are germicidal and are used in formulating disinfectants.

A spot test in lichenology is a spot analysis used to help identify lichens. It is performed by placing a drop of a chemical on different parts of the lichen and noting the colour change associated with application of the chemical. The tests are routinely encountered in dichotomous keys for lichen species, and they take advantage of the wide array of lichen products produced by lichens and their uniqueness among taxa. As such, spot tests reveal the presence or absence of chemicals in various parts of a lichen. They were first proposed by the botanist William Nylander in 1866.

Remototrachyna is a genus of foliose lichens in the large family Parmeliaceae. It was separated from the genus Hypotrachyna based on the structure of the excipulum and genetic differences.

<span class="mw-page-title-main">Isolichenan</span> An α-glucan occurring in certain species of lichens

Isolichenan, also known as isolichenin, is a cold-water-soluble α-glucan occurring in certain species of lichens. This lichen product was first isolated as a component of an extract of Iceland moss in 1813, along with lichenin. After further analysis and characterization of the individual components of the extract, isolichenan was named in 1881. It is the first α-glucan to be described from lichens. The presence of isolichenan in the cell walls is a defining characteristic in several genera of the lichen family Parmeliaceae. Although most prevalent in that family, it has also been isolated from members of the families Ramalinaceae, Stereocaulaceae, Roccellaceae, and Cladoniaceae. Experimental studies have shown that isolichenan is produced only when the two lichen components – fungus and alga – are growing together, not when grown separately. The biological function of isolichenan in the lichen thallus is unknown.

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

Olivetolic acid is an organic compound that is an intermediate in the biosynthetic pathway of the cannabinoids in Cannabis sativa.

Cetrelia sayanensis is a species of foliose lichen in the family Parmeliaceae. Found in Europe, it was formally described as a new species in 2009 by lichenologists Tatyana Otnyukova, Nikolay Stepanov, and John Alan Elix. The type was collected along the Kulumys ridge on the West Sayan Mountains of southern Siberia. Here it was found growing on the bark of an old stem of Sorbus sibirica, at an altitude of 800 m (2,600 ft). It has also been collected in several neighbouring areas, all at altitudes between 400–930 m (1,310–3,050 ft), with the bark of Abies, Betula, Salix, and Sorbus as the typical substrates. In 2019, the lichen was recorded from Austria, its first reported occurrence in middle Europe.

Punctelia subflava is a species of foliose lichen in the family Parmeliaceae that occurs in Australia.

<span class="mw-page-title-main">Salazinic acid</span> Chemical compound found in some lichens

Salazinic acid is a depsidone with a lactone ring. It is found in some lichens, and is especially prevalent in Parmotrema and Bulbothrix, where its presence or absence is often used to help classify species in those genera.

<span class="mw-page-title-main">Lichexanthone</span> Chemical compound found in some lichens

Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese chemists from a species of leafy lichen in the 1940s. The compound is known to occur in many lichens, and it is important in the taxonomy of species in several genera, such as Pertusaria and Pyxine. More than a dozen lichen species have a variation of the word lichexanthone incorporated as part of their binomial name. The presence of lichexanthone in lichens causes them to fluoresce a greenish-yellow colour under long-wavelength UV light; this feature is used to help identify some species. Lichexanthone is also found in several plants, and some species of fungi that do not form lichens.

<i>Hypotrachyna osseoalba</i> Species of lichen

Hypotrachyna osseoalba, commonly known as the grainy loop lichen, is a species of foliose lichen in the family Parmeliaceae. It is widely distributed in subtropical and temperate areas of the world. Characteristic features of the lichen include the pustules in its cortex, the somewhat linear shape of the lobes comprising the thallus, and the branched rhizines.

<span class="mw-page-title-main">Barbatic acid</span> Chemical compound found in some lichens

Barbatic acid is an organic compound that is made by some lichens. It is in the structural class known as depsides. It is particularly common in the genera Usnea and Cladonia.

References

  1. 1 2 3 4 Elix, J. A. (1974). "Synthesis of para-olivetol depsides". Australian Journal of Chemistry. 27 (8): 1767. doi:10.1071/CH9741767.
  2. 1 2 Cheng, Bokun; Cao, Shugeng; Vasquez, Victor; Annamalai, Thirunavukkarasu; Tamayo-Castillo, Giselle; Clardy, Jon; Tse-Dinh, Yuk-Ching (8 April 2013). "Identification of Anziaic Acid, a Lichen Depside from Hypotrachyna sp., as a New Topoisomerase Poison Inhibitor". PLOS ONE. 8 (4): e60770. Bibcode:2013PLoSO...860770C. doi: 10.1371/journal.pone.0060770 . PMC   3620467 . PMID   23593306.
  3. Kekuda, T.R Prashith; Lavanya, D .; Pooja, Rao (March 2019). "Lichens as promising resources of enzyme inhibitors: A review". Journal of Drug Delivery and Therapeutics. 9 (2S). doi:10.22270/jddt.v9i2-s.2546 (inactive 31 December 2022).{{cite journal}}: CS1 maint: DOI inactive as of December 2022 (link)
  4. Ramaut, J. L.; Serusiaux, E.; Brouers, M.; Corvisier, M. (1978). "Lichen Acids of the Stereocaulon ramulosum Group in Central East Africa". The Bryologist. 81 (3): 415. doi:10.2307/3242244. JSTOR   3242244.
  5. Mark, Kristiina; Randlane, Tiina; Thor, Göran; Hur, Jae-Seoun; Obermayer, Walter; Saag, Andres (2019). "Lichen chemistry is concordant with multilocus gene genealogy in the genus Cetrelia (Parmeliaceae, Ascomycota)". Fungal Biology. 123 (2): 125–139. doi:10.1016/j.funbio.2018.11.013. PMID   30709518. S2CID   73439650.