# Salazinic acid

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Chemical compound found in some lichens

Salazinic acid 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 CAS Number 521-39-1 3D model (JSmol) Interactive image ChEMBL ChEMBL172439 ChemSpider 4478508 ECHA InfoCard 100.007.558 EC Number 208-312-0 PubChem CID 5320418 CompTox Dashboard (EPA) DTXSID001317270 InChI 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 SMILES CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3CO)O)C(=O)OC4O)C=O)O Properties Chemical formula 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). Infobox references

Chemical compound

**Salazinic acid** is a [depsidone](/source/Depsidone) with a [lactone](/source/Lactone) ring. It is found in some [lichens](/source/Lichen), and is especially prevalent in *[Parmotrema](/source/Parmotrema)* and *[Bulbothrix](/source/Bulbothrix)*, where its presence or absence is often used to help [classify](/source/Classification_(biology)) species in those [genera](/source/Genus).

## History

In 1897, [Friedrich Wilhelm Zopf](/source/Friedrich_Wilhelm_Zopf) named the chemical he originally isolated from the African species *[Stereocaulon salazinum](https://en.wikipedia.org/w/index.php?title=Stereocaulon_salazinum&action=edit&redlink=1)* as salazinic acid.[1] Later studies showed that the compound he named was actually [norstictic acid](/source/Norstictic_acid).[2]

In 1933, [Yasuhiko Asahina](/source/Yasuhiko_Asahina) and J. Asano studied salazinic acid they had isolated from *[Parmelia cetrata](https://en.wikipedia.org/w/index.php?title=Parmelia_cetrata&action=edit&redlink=1)*, and found a unique [ring system](/source/Ring_(chemistry)) with seven members containing two [phenolic](/source/Phenols) components. The fundamental structure was named [depsidone](/source/Depsidone), that is, a seven-membered ring with an oxygen bridge binding two [aromatic](/source/Aromaticity) rings.[3] Japanese chemists demonstrated in the late 1960s that the isolated [mycobiont](/source/Mycobiont) of the lichen *[Ramalina crassa](https://en.wikipedia.org/w/index.php?title=Ramalina_crassa&action=edit&redlink=1)* could produce salazinic acid when grown in [laboratory culture](/source/Microbiological_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](/source/Ramalina_siliquosa)* when grown in malt [yeast extract](/source/Yeast_extract) medium supplemented with low amounts of [sucrose](/source/Sucrose).[5][6] When extra sucrose was added to the growth medium, the production of salazinic acid was observed; the increased [osmolality](/source/Osmotic_concentration) enhances the reaction from 4-*O*-demethylbarbatic acid to salazinic acid.[7]

## Properties

Salazinic acid has a [molecular formula](/source/Molecular_formula) of C18H12O10, and a [molecular mass](/source/Molecular_mass) of 388.3 grams/[mole](/source/Mole_(unit)). In its purified form, it exists as colourless needles with a [melting point](/source/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](/source/Solubility) in water is about 27 milligrams per litre.[8]

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

The complete [1H](/source/Proton_NMR) and [13C NMR](/source/Carbon-13_nuclear_magnetic_resonance) spectral assignments for salazinic acid were reported in 2000.[14]

## Occurrence

*[Parmotrema stuppeum](https://en.wikipedia.org/w/index.php?title=Parmotrema_stuppeum&action=edit&redlink=1)* (left) and *[Parmotrema subisidiosum](https://en.wikipedia.org/w/index.php?title=Parmotrema_subisidiosum&action=edit&redlink=1)* (right) are two [foliose lichens](/source/Foliose_lichen) that contain salazinic acid.[15]

Salazinic acid is derived via the [acetyl polymalonyl pathway](https://en.wikipedia.org/w/index.php?title=Acetyl_polymalonyl_pathway&action=edit&redlink=1), a [metabolic pathway](/source/Metabolic_pathway) that uses [acetyl-CoA](/source/Acetyl-CoA) and [malonyl-CoA](/source/Malonyl-CoA) (derivatives of [coenzyme A](/source/Coenzyme_A)). The compound is common in the large lichen genus *[Parmotrema](/source/Parmotrema)*, and plays an important role in the [chemotaxonomy](/source/Chemotaxonomy) and [systematics](/source/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](/source/Bulbothrix)*.[16][17]

In nature, salazinic acid serves as an [antioxidant](/source/Antioxidant) as well as a [photoprotectant](/source/Photoprotection), helping the lichen to survive in conditions of both [abiotic](/source/Abiotic_stress) and [biotic stress](/source/Biotic_stress). A study of three [foliose lichen](/source/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](/source/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]

## Related compounds

The depsidones [chalybaeizanic acid](https://en.wikipedia.org/w/index.php?title=Chalybaeizanic_acid&action=edit&redlink=1) and [quaesitic acid](https://en.wikipedia.org/w/index.php?title=Quaesitic_acid&action=edit&redlink=1), isolated from the lichens *[Xanthoparmelia amphixanthoides](https://en.wikipedia.org/w/index.php?title=Xanthoparmelia_amphixanthoides&action=edit&redlink=1)* and *[Hypotrachyna quaesita](https://en.wikipedia.org/w/index.php?title=Hypotrachyna_quaesita&action=edit&redlink=1)*, respectively, are [structurally](/source/Chemical_structure) similar to salazinic acid.[20] In consalazinic acid, the [aldehyde](/source/Aldehyde) group of salazinic acid is replaced with a [benzyl alcohol](/source/Benzyl_alcohol) functional group.[21]

8'-*O*-Methylsalazinic acid was isolated from *[Parmotrema dilatatum](https://en.wikipedia.org/w/index.php?title=Parmotrema_dilatatum&action=edit&redlink=1)*.[22] Several new synthesised derivatives of salazinic acid were reported in 2021 using [bromination](/source/Bromination), [nucleophilic addition](/source/Nucleophilic_addition), [Friedel-Crafts alkylation](/source/Friedel-Crafts_alkylation), and [esterification](/source/Esterification).[23]

## Eponyms

Several authors have explicitly named salazinic acid in the [specific epithets](/source/Botanical_name) of their published lichen species, thereby acknowledging the presence of this compound as an important [taxonomic](/source/Taxonomy_(biology)) characteristic. These [eponyms](/source/Eponym) are listed here, followed by their [taxonomic authority](/source/Author_citation_(botany)) and year of publication:

- *[Acanthothecis salazinica](/source/Acanthothecis_salazinica)* van den Boom & Sipman (2013)[24]

- *[Bryoria salazinica](https://en.wikipedia.org/w/index.php?title=Bryoria_salazinica&action=edit&redlink=1)* [Brodo](/source/Irwin_Brodo) & [D.Hawksw.](/source/D.Hawksw.) (1977)[25]

- *[Graphina salazinica](/source/Graphina_salazinica)* [A.W.Archer](/source/A.W.Archer) (2001)[26]

- *[Karoowia salazinica](/source/Karoowia_salazinica)* [Hale](/source/Mason_Hale) (1989)[27]

- *[Lepraria salazinica](/source/Lepraria_salazinica)* Tønsberg (2007)[28]

- *[Myelochroa salazinica](/source/Myelochroa_salazinica)* Sheng L.Wang, J.B.Chen & [Elix](/source/John_Alan_Elix) (2001)[29]

- *[Ocellularia salazinica](https://en.wikipedia.org/w/index.php?title=Ocellularia_salazinica&action=edit&redlink=1)* Papong, Mangold & Lücking (2014)[30]

- *[Pertusaria salazinica](/source/Pertusaria_salazinica)* A.W.Archer & Elix (2017)[31]

- *[Phaeographina salazinica](/source/Phaeographina_salazinica)* A.W.Archer (2003)[32]

- *[Psiloparmelia salazinica](/source/Psiloparmelia_salazinica)* Elix & [T.H.Nash](/source/T.H.Nash) (1992)[33]

- *[Diorygma salazinicum](/source/Diorygma_salazinicum)* Sutjar. & [Kalb](/source/Klaus_Kalb) (2014)[34]

- *[Oropogon salazinicus](/source/Oropogon_salazinicus)* Essl. (1989)[35]

## References

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1. **[^](#cite_ref-Hale_1989_27-0)** Hale, M.E. (1989). ["A monograph of the lichen genus *Karoowia* Hale"](http://www.cybertruffle.org.uk/cyberliber/59575/0035/001/0189.htm). *Mycotaxon*. **35** (1): 189.

1. **[^](#cite_ref-Tønsberg_2007_28-0)** 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.

1. **[^](#cite_ref-Wang_et_al._2001_29-0)** Wang, S.L.; Chen, J.B.; Elix, J.A. (2001). ["Two new species of the lichen genus *Myelochroa* (Parmeliaceae, Ascomycota) from China"](http://www.cybertruffle.org.uk/cyberliber/59575/0077/0025.htm). *Mycotaxon*. **77**: 25–30.

1. **[^](#cite_ref-Papong_et_al._2014_30-0)** 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](/source/Doi_(identifier)):[10.11646/phytotaxa.189.1.16](https://doi.org/10.11646%2Fphytotaxa.189.1.16).

1. **[^](#cite_ref-Archer_&_Elix_2017_31-0)** 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"](https://www.anbg.gov.au/abrs/lichenlist/AL80.pdf) (PDF). *Australasian Lichenology*. **80**: 6.

1. **[^](#cite_ref-Archer_2003_32-0)** Archer, A.W. (2003). ["New species in the lichen family Graphidaceae (Ascomycota) from Australia and the Solomon Islands"](http://www.cybertruffle.org.uk/cyberliber/59575/0088/0147.htm). *Mycotaxon*. **88**: 143–147.

1. **[^](#cite_ref-Elix_&_Nash_1992_33-0)** [Elix, John A.](/source/John_Alan_Elix); Nash, Thomas H. (1992). "A synopsis of the lichen genus *Psiloparmelia* (Ascomycotina, Parmeliaceae)". *The Bryologist*. **95** (4): 388. [doi](/source/Doi_(identifier)):[10.2307/3243562](https://doi.org/10.2307%2F3243562). [JSTOR](/source/JSTOR_(identifier)) [3243562](https://www.jstor.org/stable/3243562).

1. **[^](#cite_ref-Sutjaritturakan_et_al._2014_34-0)** Sutjaritturakan, Jutarat; Saipunkaew, Wanaruk; Boonpragob, Kansri; Kalb, Kalb (2014). "New species of Graphidaceae (Ostropales) Lecanoromycetes) from southern Thailand". *Phytotaxa*. **189** (1): 312–324. [doi](/source/Doi_(identifier)):[10.11646/PHYTOTAXA.189.1.22](https://doi.org/10.11646%2FPHYTOTAXA.189.1.22).

1. **[^](#cite_ref-Esslinger_1989_35-0)** 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](/source/ISBN_(identifier)) [978-0-912861-28-9](https://en.wikipedia.org/wiki/Special:BookSources/978-0-912861-28-9).

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