Salazinic acid

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Salazinic acid
Salazinic acid.svg
Names
IUPAC name
1,3-Dihydro-1,4,10-trihydroxy-5-(hydroxymethyl)-8-methyl-3,7-dioxo-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-11-carboxaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.558 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 208-312-0
PubChem CID
  • InChI=1S/C18H12O10/c1-5-2-8(21)6(3-19)13-9(5)16(23)27-14-7(4-20)12(22)10-11(15(14)26-13)18(25)28-17(10)24/h2-3,18,20-22,25H,4H2,1H3
    Key: QQTKVXCQLZIJPP-UHFFFAOYSA-N
  • CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3CO)O)C(=O)OC4O)C=O)O
Properties
C18H12O10
Molar mass 388.284 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Contents

History

In 1897, Friedrich Wilhelm Zopf named the chemical he originally isolated from the African species Stereocaulon salazinum as salazinic acid. [1] Later studies showed that the compound he named was actually norstictic acid. [2]

In 1933, Yasuhiko Asahina and J. Asano studied salazinic acid they had isolated from Parmelia cetrata , and found a unique ring system with seven members containing two phenolic components. The fundamental structure was named depsidone, that is, a seven-membered ring with an oxygen bridge binding two aromatic rings. [3] Japanese chemists demonstrated in the late 1960s that the isolated mycobiont of the lichen Ramalina crassa could produce salazinic acid when grown in laboratory culture. [4] Subsequent studies tried to determine the influence of environmental factors on the production of salazinic acid in culture. For example, two studies in the late 1980s showed that only 4-O-demethylbarbatic acid (a precursor of salazinic acid) was produced by the isolated mycobiont of Ramalina siliquosa when grown in malt yeast extract medium supplemented with low amounts of sucrose. [5] [6] When extra sucrose was added to the growth medium, the production of salazinic acid was observed; the increased osmolality enhances the reaction from 4-O-demethylbarbatic acid to salazinic acid. [7]

Properties

Salazinic acid has a molecular formula of C18H12O10, and a molecular mass of 388.3 grams/mole. In its purified form, it exists as colourless needles with a melting point range between 260–268 °C (500–514 °F) that undergo a colour change to brown at about 240 °C (464 °F). Its solubility in water is about 27 milligrams per litre. [8]

The compound has been shown in in vitro studies to have antimicrobial properties, [9] [10] but it did not have any substantive antimycobacterial effects when tested against Mycobacterium aurum . [11] [12] Recent (2021) research indicates that salazinic acid is a potent modulator of Nrf2, NF-κB and STAT3 signaling pathways in colorectal cancer cells. [13]

The complete 1H and 13C NMR spectral assignments for salazinic acid were reported in 2000. [14]

Occurrence

Parmotrema stuppeum - Flickr - pellaea.jpg
Parmotrema subisidiosum (4504575802).jpg
Parmotrema stuppeum (left) and Parmotrema subisidiosum (right) are two foliose lichens that contain salazinic acid. [15]

Salazinic acid is derived via the acetyl polymalonyl pathway, a metabolic pathway that uses acetyl-CoA and malonyl-CoA (derivatives of coenzyme A). The compound is common in the large lichen genus Parmotrema , and plays an important role in the chemotaxonomy and systematics of that genus. A 2020 revision included 66 salazinic acid-containing species. [15] The presence or absence of the compound is also important in the classification of genus Bulbothrix . [16] [17]

In nature, salazinic acid serves as an antioxidant as well as a photoprotectant, helping the lichen to survive in conditions of both abiotic and biotic stress. A study of three foliose lichen species showed higher quantities of salazinic acid correlating with increases in altitude. [18] An earlier study demonstrated other possible effects of environmental conditions on salazinic acid content. It was shown that the salazinic acid content of Ramalina siliquosa is higher where the annual mean temperature is higher, and the content of the lichens growing on the dark-coloured rock or on the southern rock face is higher than that of the lichens growing on the light-coloured rock or on the northern rock face. [19]

The depsidones chalybaeizanic acid and quaesitic acid, isolated from the lichens Xanthoparmelia amphixanthoides and Hypotrachyna quaesita , respectively, are structurally similar to salazinic acid. [20] In consalazinic acid, the aldehyde group of salazinic acid is replaced with a benzyl alcohol functional group. [21]

8'-O-Methylsalazinic acid was isolated from Parmotrema dilatatum . [22] Several new synthesised derivatives of salazinic acid were reported in 2021 using bromination, nucleophilic addition, Friedel-Crafts alkylation, and esterification. [23]

Eponyms

Several authors have explicitly named salazinic acid in the specific epithets of their published lichen species, thereby acknowledging the presence of this compound as an important taxonomic characteristic. These eponyms are listed here, followed by their taxonomic authority and year of publication:

Related Research Articles

<i>Ramalina</i> Genus of lichenised fungi in the family Ramalinaceae

Ramalina is a genus of greenish fruticose lichens that grow in the form of flattened, strap-like branches. Members of the genus are commonly called strap lichens or cartilage lichens. Apothecia are lecanorine.

<i>Acanthothecis</i> Genus of lichen

Acanthothecis is a genus of lichen-forming fungi in the family Graphidaceae. The genus was circumscribed by Frederick Edward Clements in 1909.

<i>Parmotrema</i> Genus of fungi

Parmotrema is a genus of lichen belonging to the family Parmeliaceae. It is a large genus, containing an estimated 300 species, with a centre of diversity in subtropical regions of South America and the Pacific Islands.

Psiloparmelia is a genus of lichen belonging to the family Parmeliaceae. It contains 13 Southern Hemisphere species, most of which are found growing on rocks at high elevations in South America. There are several characteristic features of the genus that are used to distinguish it from the morphologically similar genera, such as Arctoparmelia, Flavoparmelia, and Xanthoparmelia. These include a dark, velvety lower thallus surface that usually lacks rhizines, a negative test for lichenan, and a high concentration of usnic acid and atranorin in the cortex.

<i>Niebla</i> (lichen) Genus of lichen

Niebla is a genus of yellow-green fruticose lichens that grow on rocks, trees, and shrubs within the fog zone of coastal North America, or more narrowly defined to occur on rocks and soil along the Pacific Coast from Mendocino County in California south to Baja California Sur.

André Aptroot is a Dutch mycologist and lichenologist.

Bulbothrix meizospora is a species of foliose lichen in the family Parmeliaceae. It is found in Africa, Asia, and South America, where it grows on tree bark.

Helge Thorsten Lumbsch is a German-born lichenologist living in the United States. His research interests include the phylogeny, taxonomy, and phylogeography of lichen-forming fungi; lichen diversity; lichen chemistry and chemotaxonomy. He is the Associate Curator and Head of Cryptogams and Chair of the Department of Botany at the Field Museum of Natural History.

Constipatic acid Chemical compound

Constipatic acid is a fatty acid found in several lichen species. It was isolated, identified, and named by Douglas Chester and John Alan Elix in a 1979 publication. The compound was extracted from the Australian leafy lichen called Xanthoparmelia constipata, which was collected on schist boulders west of Springton, South Australia. The related compounds protoconstipatic acid and dehydroconstipatic acid were also reported concurrently. Syo Kurokawa and Rex Filson had previously detected the compounds using thin-layer chromatography when they formally described the lichen as a new species in 1975, but had not characterised them chemically.

Acanthothecis salazinica is a species of script lichen in the family Graphidaceae. Found in Panama, it was described as a new species in 2013 by Pieter van den Boom and Harrie J. Sipman. The type specimen was collected near Paraíso, Panamá Province, close to the botanical garden in the Summit Park. Here it was growing on the bark of a cultivated Parmentiera cereifera tree. The lichen contains the secondary chemical salazinic acid, for which it is named. Acanthothecis subclavulifera is quite similar in morphology, but it contains protocetraric acid rather than salazinic acid and it has a different ascospore structure.

Myelochroa salazinica is a species of foliose lichen in the family Parmeliaceae. Found in China, it was described as a new species in 2001 by Sheng-Lan Wang, Jian-Bin Chen, and John Alan Elix.

Pertusaria salazinica is a species of crustose lichen in the family Pertusariaceae. Found in Australia, it was described as a new species in 2017 by lichenologists Alan Archer and John Alan Elix. The type specimen was collected in Tully Gorge National Park (Queensland) at an altitude of 885 m (2,904 ft). Here, in a montane rainforest, it was found growing on a rotting log. The specific epithet refers to the presence of salazinic acid, a major secondary compound in the lichen. It also contains norstictic acid as a major metabolite, and connorstictic acid as a minor metabolite. Pertusaria salazinica is only known from the type specimen.

Phaeographis salazinica is a species of script lichen in the family Graphidaceae. Found in the Solomon Islands, the lichen was first described as a new species in 2003 by Australian lichenologist Alan W. Archer. He named it Phaeographis salazinica, with the specific epithet referring to the presence of the compound salazinic acid as its major secondary compound. The lichen also contains trace amounts of consalazinic acid, connorstictic acid, norstictic acid, subnorstictic acid, protocetraric acid, and methyl norstictate. The type specimen was collected near Tatamba on Tanabuli Island. The main morphological characteristics of Phaeographis salazinica are the conspicuous lirellae, and the large brown muriform ascospores. Archer transferred the taxon to the genus Phaeographis in 2007.

Xanthoparmelia salazinica is a species of lichen in the family Parmeliaceae. Found in South Africa, it was described as a new species in 1989 by American lichenologist Mason Hale. He classified it in Karoowia, a genus that has since been placed in synonymy with Xanthoparmelia following molecular phylogenetic analysis published in 2010.

Carbacanthographis salazinica is a species of script lichen in the family Graphidaceae. Found in Australia, it was described as a new species in 2001 by lichenologist Alan Archer. The type specimen was collected by Archer in Conglomerate State Forest. Here the lichen was found growing on the bark of a palm tree. Its thallus is thin and grayish-green, with conspicuous white lirellae measuring 1–4 mm long. The specific epithet refers to salazinic acid, the presence of which is a distinguishing characteristic of this species. The lichen also has trace amounts of other secondary chemicals, including consalazinic acid, norstictic acid, and protocetraric acid. In 2005 Archer transferred the taxon to genus Carbacanthographis.

Parmotrema lichexanthonicum is a species of foliose lichen in the family Parmeliaceae. Found in Brazil, it was formally described as a new species in 1997 by Sionara Eliasaro and Mónica Adler. The type specimen was collected by the first author from the Serra do Cipó ; here the lichen was found growing on a rock. The specific epithet lichexanthonicum refers to the presence of the secondary compound lichexanthone in the medulla of the lichen. Other compounds in the lichen are the depsidone salazinic acid, and the depside atranorin. A close relative to this species is Parmotrema ultralucens, which contains the same cortical and medullary metabolites.

Sekikaic acid Chemical compound found in some lichens

Sekikaic acid is an organic compound in the structural class of chemicals known as depsides. It is found in some lichens. First isolated from Ramalina sekika, it is a fairly common lichen product in the genera Ramalina and Cladonia. The species epithet of the powdery lichen Lepraria sekikaica refers to the presence of this substance—a rarity in genus Lepraria.

Henricus (Harrie) Johannes Maria Sipman is a Dutch lichenologist. He specialises in tropical and subtropical lichens, and has authored or co-authored more than 250 scientific publications. He was the curator of the lichen herbarium at the Berlin Botanical Garden and Botanical Museum from 1983 until his retirement in 2010.

<i>Ramalina americana</i> Species of lichen

Ramalina americana, commonly known as the sinewed ramalina, is a pale green fruticose lichen that is found across the Northern US Midwest, extending into Southern Canada and the Eastern Seaboard. It is characterized morphologically by the presence of pseudocyphellae, straight spores, and its unique chemical diversity.

References

  1. ↑ Zopf, Wilhelm (1897). "Zur Kenntniss der Flechtenstoffe". Justus Liebigs Annalen der Chemie (in German). 297 (2): 222–256. doi:10.1002/jlac.18972950209.
  2. ↑ Asahina, Yasuhiko; Shibata, Shoji (1954). Chemistry of Lichen Substances. Tokyo: Japan Society for the Promotion of Science. pp. 130–134. ISBN   978-0-598-82060-0.
  3. ↑ Shibata, Shoji (2000). "Yasuhiko Asahina (1880–1975) and his studies on lichenology and chemistry of lichen metabolites". The Bryologist. 103 (4): 710–719. doi:10.1639/0007-2745(2000)103[0710:yaahso]2.0.co;2. S2CID   86351217.
  4. ↑ Komiya, Takeya; Shibata, Shoji (1969). "Formation of lichen substances by mycobionts of lichens. Isolation of (+) usnic acid and salazinic acid from mycobionts of Ramalina spp". Chemical and Pharmaceutical Bulletin. 17 (6): 1305–1306. doi:10.1248/cpb.17.1305.
  5. ↑ Hamada, Nobuo; Ueno, Tamio (1987). "Depside from an isolated lichen mycobiont". Agricultural and Biological Chemistry. 51 (6): 1705–1706. doi:10.1080/00021369.1987.10868233.
  6. ↑ Hamada, Nobuo (1989). "The effect of various culture conditions on depside production by an isolated lichen mycobiont". The Bryologist. 92 (3): 310–313. doi:10.2307/3243399. JSTOR   3243399.
  7. ↑ Hamada, Nobuo; Miyagawa, Hisashi (1995). "Secondary metabolites from isolated lichen mycobionts cultured under different osmotic conditions". The Lichenologist. 27 (3): 201–205. doi:10.1016/s0024-2829(95)80018-2. S2CID   84545779.
  8. ↑ Iskandar, I.K.; Syers, J.K. (1971). "Solubility of lichen compounds in water: pedogenetic implications". The Lichenologist. 5 (1–2): 45–50. doi:10.1017/s0024282971000082. S2CID   86701324.
  9. ↑ Candan, Mehmet; Yılmaz, Meral; Tay, Turgay; Erdem, Murat; Türk, Ayşen Özdemir (2007). "Antimicrobial activity of extracts of the lichen Parmelia sulcata and its salazinic acid constituent". Zeitschrift für Naturforschung C. 62 (7–8): 619–621. doi:10.1515/znc-2007-7-827. PMID   17913083. S2CID   20709081.
  10. ↑ Manojlovića, Nedeljko; Ranković, Branislav; Kosanić, Marijana; Vasiljević, Perica; Stanojković, Tatjana (2012). "Chemical composition of three Parmelia lichens and antioxidant, antimicrobial and cytotoxic activities of some their major metabolites". Phytomedicine. 19 (13): 1166–1172. doi:10.1016/j.phymed.2012.07.012. PMID   22921748.
  11. ↑ Ingólfsdóttir, Kristı́n; Chung, Gavin A.C.; Skúlason, Vilhjálmur G.; Gissurarson, Stefán R.; Vilhelmsdóttir, Margrét (1998). "Antimycobacterial activity of lichen metabolites in vitro". European Journal of Pharmaceutical Sciences. 6 (2): 141–144. doi:10.1016/s0928-0987(97)00078-x. PMID   9795033.
  12. ↑ Honda, N.K.; Pavan, F.R.; Coelho, R.G.; de Andrade Leite, S.R.; Micheletti, A.C.; Lopes, T.I.B.; Misutsu, M.Y.; Beatriz, A.; Brum, R.L.; Leite, C.Q.F. (2010). "Antimycobacterial activity of lichen substances". Phytomedicine. 17 (5): 328–332. doi:10.1016/j.phymed.2009.07.018. PMID   19683421.
  13. ↑ Papierska, Katarzyna; Krajka-Kuźniak, Violetta; Paluszczak, Jarosław; Kleszcz, Robert; Skalski, Marcin; Studzińska-Sroka, Elżbieta; Baer-Dubowska, Wanda (2021). "Lichen-derived depsides and depsidones modulate the Nrf2, NF-κB and STAT3 signaling pathways in colorectal cancer cells". Molecules. 26 (16): 4787. doi: 10.3390/molecules26164787 . PMC   8400444 . PMID   34443375.
  14. ↑ Eifler-Lima, V. L.; Sperry, A.; Sinbandhit, S.; Boustie, J.; Tomasi, S.; Schenkel, E. (2000). "NMR spectral data of salazinic acid isolated from some species of Parmotrema". Magnetic Resonance in Chemistry. 38 (6): 472–474. doi:10.1002/1097-458X(200006)38:6<472::AID-MRC658>3.0.CO;2-P. S2CID   96531766.
  15. 1 2 Spielmann, Adriano Afonso; Marcelli, Marcelo Pinto (2020). "Type studies on Parmotrema (Parmeliaceae, Ascomycota) with salazinic acid". Plant and Fungal Systematics. 65 (2): 403–508. doi: 10.35535/pfsyst-2020-0028 .
  16. ↑ Benatti, M.N. (2012). "A review of the genus Bulbothrix Hale: the isidiate, sorediate, and pustulate species with medullary salazinic acid". Mycosphere. 4 (1): 1–30. doi:10.5943/mycosphere/4/1/1.
  17. ↑ Benatti, Michel (2012). "A review of the genus Bulbothrix Hale: the species with medullary salazinic acid lacking vegetative propagules". MycoKeys. 5: 1–30. doi:10.3897/mycokeys.5.3342.
  18. ↑ Shukla, Vertika; Patel, D.K.; Bajpai, Rajesh; Semwal, Manoj; Upreti, D.K. (2015). "Ecological implication of variation in the secondary metabolites in Parmelioid lichens with respect to altitude". Environmental Science and Pollution Research. 23 (2): 1391–1397. doi:10.1007/s11356-015-5311-z. PMID   26370809. S2CID   207276246.
  19. ↑ Hamada, N. (1982). "The effect of temperature on the content of the medullary depsidone salazinic acid in Ramalina siliquosa (lichens)". Canadian Journal of Botany. 60 (4): 383–385. doi:10.1139/b82-053.
  20. ↑ Elix, John A.; Wardlaw, Judith H. (1999). "The structure of chalybaeizanic acid and quaesitic acid, two new lichen depsidones related to salazinic acid". Australian Journal of Chemistry. 52 (7): 713–716. doi:10.1071/CH99056.
  21. ↑ O'Donovan, Donal G.; Roberts, George; Keogh, Myles F. (1980). "Structure of the β-orcinol depsidones, connorstictic and consalazinic acids". Phytochemistry. 19 (11): 2497–2499. doi:10.1016/s0031-9422(00)91070-7. S2CID   85350700.
  22. ↑ Asshaima Paramita Devi, Thuc-Huy Duong, Solenn Ferron, Mehdi A Beniddir, Minh-Hiep Dinh, Van-Kieu Nguyen, Nguyen-Kim-Tuyen Pham, Dinh-Hung Mac, Joël Boustie, Warinthorn Chavasiri, Pierre Le Pogam (2020). "Salazinic acid-derived depsidones and diphenylethers with α-glucosidase inhibitory activity from the lichen Parmotrema dilatatum". Planta Medica. 86 (16): 1216–1224. doi:10.1055/a-1203-0623. PMID   32819010. S2CID   221221650.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  23. ↑ Pham, Nguyen-Kim-Tuyen; Tran, Nguyen-Minh-An; Truong Nguyen, Huy; Pham, Duc-Dung; Nguyen, Thi-Quynh-Trang; Nguyen, Thi-Hong-Anh; Nguyen, Huu-Tri; Do, Thanh-Hung; Nguyen, Ngoc-Hong; Duong, Thuc-Huy (2022). "Design, modification, and bio-evaluation of salazinic acid derivatives". Arabian Journal of Chemistry. 15 (1): 103535. doi: 10.1016/j.arabjc.2021.103535 .
  24. ↑ van den Boom, Pieter P.G.; Sipman, Harrie J.M. (2013). "Sixty-two species of lirelliform Graphidaceae (Ascomycota) new to Panama, with four species newly described to science". Herzogia. 26: 9–20. doi:10.13158/heia.26.1.2013.9. S2CID   84432921.
  25. ↑ Brodo, Irwin M.; Hawksworth, David L. (1977). Alectoria and allied genera in North America. Opera Botanica. Vol. 42. Stockholm: Lund Botanical Society. p. 130. ISBN   978-9154602117.
  26. ↑ Archer, A.W. (2001). "The lichen genus Graphina (Graphidaceae) in Australia: new reports and new species". Mycotaxon. 77: 176.
  27. ↑ Hale, M.E. (1989). "A monograph of the lichen genus Karoowia Hale". Mycotaxon. 35 (1): 189.
  28. ↑ Tønsberg, T. (2007). "Notes on the lichen genus Lepraria in Great Smoky Mountains National Park; southeastern North America: Lepraria lanata and L. salazinica spp. nov". Opuscula Philolichenum. 4: 51–54.
  29. ↑ Wang, S.L.; Chen, J.B.; Elix, J.A. (2001). "Two new species of the lichen genus Myelochroa (Parmeliaceae, Ascomycota) from China". Mycotaxon. 77: 25–30.
  30. ↑ Papong, Khwanruan Butsatorn; Mangold, Armin; Lücking, Robert; Lumbsch, H. Thorsten (2014). "New species and new records of thelotremoid Graphidaceae (Ascomycota: Ostropales) from Thailand". Phytotaxa. 189 (1): 238. doi:10.11646/phytotaxa.189.1.16.
  31. ↑ Archer, A.W.; Elix, J.A. (2017). "Seven new species and a new record in the lichen genus Pertusaria (Pertusariales, lichenized Ascomycota) from eastern Australia" (PDF). Australasian Lichenology. 80: 6.
  32. ↑ Archer, A.W. (2003). "New species in the lichen family Graphidaceae (Ascomycota) from Australia and the Solomon Islands". Mycotaxon. 88: 143–147.
  33. ↑ Elix, John A.; Nash, Thomas H. (1992). "A synopsis of the lichen genus Psiloparmelia (Ascomycotina, Parmeliaceae)". The Bryologist. 95 (4): 388. doi:10.2307/3243562. JSTOR   3243562.
  34. ↑ Sutjaritturakan, Jutarat; Saipunkaew, Wanaruk; Boonpragob, Kansri; Kalb, Kalb (2014). "New species of Graphidaceae (Ostropales) Lecanoromycetes) from southern Thailand". Phytotaxa. 189 (1): 312–324. doi:10.11646/PHYTOTAXA.189.1.22.
  35. ↑ Esslinger, Theodore L. (1989). Systematics of Oropogon (Alectoriaceae) in the New World. Systematic Botany Monographs. Vol. 28. American Society of Plant Taxonomists. p. 109. ISBN   978-0-912861-28-9.
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