Connorstictic acid

Last updated
Connorstictic acid
Connorstictic acid.svg
Names
IUPAC name
5,13,17-Trihydroxy-4-(hydroxymethyl)-7,12-dimethyl-2,10,16-trioxatetracyclo[9.7.0.03,8.014,18]octadeca-1(11),3(8),4,6,12,14(18)-hexaene-9,15-dione
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C18H14O9/c1-5-3-8(20)7(4-19)14-9(5)16(22)26-13-6(2)12(21)10-11(15(13)25-14)18(24)27-17(10)23/h3,18-21,24H,4H2,1-2H3 Yes check.svgY
    Key: JGHRZZSLOGDYOO-UHFFFAOYSA-N Yes check.svgY
  • Cc1cc(O)c(CO)c2c1C(=O)Oc1c(C)c(O)c3c(c1O2)C(O)OC3=O
Properties
C18H14O9
Molar mass 374.301 g·mol−1
Melting point 280–300 °C (536–572 °F; 553–573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Connorstictic acid is an organic compound in the structural class of chemicals known as depsidones. It occurs as a secondary metabolite in many lichen species in several genera.

Contents

History

Connorstictic acid was first identified and named in 1971 by Chicita Culberson and William Culberson, from chemical analysis of Diploschistes lichens. They described it as "probably a β-orcinol depsidone", and noted that it commonly co-occurred in lichens with norstictic acid. [1] Its structure was published in 1980 following spectral and elemental analysis of the compound purified from the lichen Pertusaria pseudocorallina . [2] The following year, John Elix and Labunmi Lajide corroborated the structure by synthesising it in several steps from the precursor norstictic acid. They also showed that connorstictic acid could be obtained by the direct reduction of norstictic acid by the addition of sodium triacetoxyborohydride, or by catalytic reduction. [3] In 1981, Chicita Culberson and colleagues reported on the difficulties of isolating connorstictic acid using standard thin-layer chromatography protocols, due to its co-eluting with related substances such as constictic acid and cryptostictic acid, depending on the solvent system used. They suggested that connorstictic acid could be a common or even constant satellite compound in chemistries with stictic and norstictic acids, and that many prior reports of connorstictic acid may have been misidentifications with cryptostictic acid. [4]

Properties

Connorstictic acid is a member of the class of chemical compounds called depsidones. Its IUPAC name is 5,13,17-trihydroxy-4-(hydroxymethyl)-7,12-dimethyl-2,10,16-trioxatetracyclo[9.7.0.03,8.014,18]octadeca-1(11),3(8),4,6,12,14(18)-hexaene-9,15-dione. The absorbance maxima (λmax) in the infrared spectrum occur at 1250, 1292, 1445, 1610, 1710, 1745, and 3400 cm-1. Connorstictic acid's molecular formula is C19H14O9; it has a molecular mass of 374.29  grams per mole. In its purified crystalline form, its predicted melting point is 280–300 °C (536–572 °F). [5]

Occurrence

Lichen genera from which connorstictic acid has been isolated include Bryoria , [6] Buellia , [7] Cladonia , [8] Cratiria , [9] Diorygma , [10] Graphis , [11] Paraparmelia , [12] Parmotrema , [4] Pertusaria , [2] Usnea , [13] and Xanthoparmelia . [14]

Related Research Articles

<i>Cetrelia</i> Genus of lichens in the family Parmeliaceae

Cetrelia is a genus of leafy lichens in the large family Parmeliaceae. They are commonly known as sea-storm lichens, alluding to the wavy appearance of their lobes. The name of the genus, circumscribed in 1968 by the husband and wife lichenologists William and Chicita Culberson, alludes to the former placement of these species in the genera Cetraria and Parmelia.

<i>Xanthoparmelia</i> Genus of fungi

Xanthoparmelia is a genus of foliose lichens in the family Parmeliaceae. This genus of lichen is commonly found in the United States, South America, southern Africa, Europe, Australia, and New Zealand.

<i>Menegazzia terebrata</i> Species of lichen

Menegazzia terebrata is a species of foliose lichen found scattered across many continents, including North America, South America, Europe, Africa, and Asia.

A spot test in lichenology is a spot analysis used to help identify lichens. It is performed by placing a drop of a chemical reagent 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 as a method to help identify species by the Finnish lichenologist William Nylander in 1866.

<i>Graphis crebra</i> Species of lichen in the family Graphidaceae

Graphis crebra is a species of corticolous lichen in the family Graphidaceae. It has a pantropical distribution. Like other script lichens, it grows on bark and resembles calligraphy. It can be distinguished from several other similar species by the white pruina (powder) on its apothecial discs.

<i>Graphis plumierae</i> Species of lichen

Graphis plumierae is a species of script lichen in the family Graphidaceae. It was described as new to science in 1915 by Finnish mycologist Edvard Vainio. The type was collected in Gourbeyre, Guadeloupe. In 2016, G. plumierae was reported from Portugal, which was also a new occurrence for Europe.

<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.

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.

Xanthoparmelia isidiovagans is a species of foliose lichen in the family Parmeliaceae

Xanthoparmelia subverrucigera is a species of saxicolous (rock-dwelling), foliose lichen in the family Parmeliaceae. Found in Spain and Zimbabwe, it was formally described as a new species in 2005 by lichenologists Oscar Blanco, Ana Crespo, and John Elix. The type specimen was collected by the authors in Embid de la Ribera at an altitude of 510 m (1,670 ft); here, the lichen was found growing on siliceous rocks. It has also been collected from Rhodes Matopos National Park in Zimbabwe. The specific epithet subverrucigera alludes to its resemblance with X. verrucigera.

Lichen products, also known as lichen substances, are organic compounds produced by a lichen. Specifically, they are secondary metabolites. Lichen products are represented in several different chemical classes, including terpenoids, orcinol derivatives, chromones, xanthones, depsides, and depsidones. Over 800 lichen products of known chemical structure have been reported in the scientific literature, and most of these compounds are exclusively found in lichens. Examples of lichen products include usnic acid, atranorin, lichexanthone, salazinic acid, and isolichenan, an α-glucan. Many lichen products have biological activity, and research into these effects is ongoing.

Henricus (Harrie) Johannes Maria Sipman is a retired Dutch lichenologist who specialised in tropical and subtropical lichens and authored or co-authored over 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. Between 1990 and 1997 he edited and distributed the exsiccata Lichenotheca Latinoamericana a museo botanico Berolinensi edita.

Xanthoparmelia lobuliferella is a species of saxicolous (rock-dwelling), foliose lichen in the family Parmeliaceae. Found in South Africa, it was formally described as a new species in 2002 by Australian lichenologist John Elix. The type specimen was collected from the Jonaskop mountain at an altitude of 1,600 m (5,200 ft); there it was found growing on south-facing rocks. It contains several lichen products: major amounts of usnic acid and stictic acid, and minor amounts of constictic acid, norstictic acid, cryptostictic acid, lobaric acid, stenosporonic acid, lichesterinic acid, and protolichesterinic acid. The species epithet refers to its resemblance to Xanthoparmelia lobulifera.

Xanthoparmelia malawiensis is a species of saxicolous (rock-dwelling), foliose lichen in the family Parmeliaceae. Found in Malawi, it was formally described as a new species in 2002 by Australian lichenologist John Elix. The type specimen was collected in Nyika National Park at an altitude of 2,300 m (7,500 ft), where it was found growing on granite rocks. It is only known from the type locality. It contains usnic acid and stictic acid as major lichen products, and minor amounts of constictic acid, norstictic acid, cryptostictic acid, and lusitanic acid.

Xanthoparmelia micromaculata is a species of saxicolous (rock-dwelling), lichen in the family Parmeliaceae. Found in South Africa, it was formally described as a new species in 2002 by Australian lichenologist John Elix. The type specimen was collected from the summit of Waboomsberg mountain at an altitude of 1,220 m (4,000 ft). It is only known from the type locality. The lichen has a pale yellow-green, somewhat crustose thallus, reaching a diameter of up to 1 cm (0.4 in) wide. It contains several lichen products: stictic acid as a major metabolite, minor amounts of usnic acid, constictic acid, and hypostictic acid, and minor or trace amounts of norstictic acid, hyposalazinic acid, and cryptostictic acid. The species epithet refers to the prominent maculae on the thallus surface.

Xanthoparmelia waboomsbergensis is a species of foliose lichen in the family Parmeliaceae. It was formally described as a new species in 2002 by Australian lichenologist John Elix. The type specimen was collected from the summit of Waboomsberg mountain at an altitude of 1,220 m (4,000 ft). The species epithet refers to the type locality, the only place the lichen is known to occur.

Clandestinotrema carbonera is a species of corticolous (bark-dwelling), crustose lichen in the family Graphidaceae. Found in Venezuela, it was formally described as a new species in 2018 by Ian Medeiros. The species epithet refers to the type locality – El Bosque La Carbonera-San Eusebio in the Venezuelan Andes. The species had previously been mentioned by lichenologist Mason Hale in a 1978 publication, but he did not describe it formally. This was the first reported instance of hypostictic acid isolated from a lichen.

<i>Diorygma antillarum</i> Species of lichen

Diorygma antillarum is a species of corticolous (bark-dwelling), crustose lichen in the family Graphidaceae. It is common and widespread in the Neotropical realm, primarily found on trees in the shady understory and in slightly illuminated habitats of lowland to montane rainforests. It produces norstictic acid and salazinic acid.

References

  1. ↑ Culberson, Chicita F.; Culberson, William Louis (1971). "The chemistry of some species of the lichen genus Diploschistes". Mycologia. 63 (2): 422–426. doi:10.1080/00275514.1971.12019122. PMID   5576435.
  2. 1 2 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. Bibcode:1980PChem..19.2497O. doi:10.1016/S0031-9422(00)91070-7.
  3. ↑ Elix, J.A.; Lajide, L. (1981). "The structure of connorstictic acid. A depsidone from the lichen Lecidea aspidula". Australian Journal of Chemistry. 34 (3): 583–586. doi:10.1071/CH9810583.
  4. 1 2 Culberson, Chicita F.; Culberson, William Louis; Johnson, Anita (1981). "A standardized TLC analysis of β-orcinol depsidones". The Bryologist. 84 (1): 16–29. doi:10.2307/3242974. JSTOR   3242974.
  5. ↑ Huneck, Siegfried (1996). Identification of Lichen Substances. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 318–319. ISBN   978-3-642-85245-9. OCLC   851387266.
  6. ↑ Boluda, Carlos G.; Rico, Víctor J.; Crespo, Ana; Divakar, Pradeep K.; Hawksworth, David L. (2015). "Molecular sequence data from populations of Bryoria fuscescens s. lat. in the mountains of central Spain indicates a mismatch between haplotypes and chemotypes". The Lichenologist. 47 (5): 279–286. doi:10.1017/S0024282915000274. S2CID   91057990.
  7. ↑ Elix, John A. (2016). "New species and new records of buellioid lichens from islands of the South Pacific Ocean". Telopea. 19: 1–10. doi:10.7751/telopea9265.
  8. ↑ Sepúlveda, Beatriz; Cornejo, Alberto; Bárcenas-Pérez, Daniela; Cheel, José; Areche, Carlos (2022). "Two new fumarprotocetraric acid lactones identified and characterized by UHPLC-PDA/ESI/ORBITRAP/MS/MS from the Antarctic lichen Cladonia metacorallifera". Separations. 9 (2): e41. doi: 10.3390/separations9020041 .
  9. ↑ Elix, John A. (2014). "New species and new records of the lichen genus Cratiria (Physciaceae, Ascomycota) in Australia". Telopea. 16: 141–148. doi:10.7751/telopea20147894.
  10. ↑ Feuerstein, Shirley Cunha; Cunha-Dias, Iane Paula Rego; Aptroot, André; Eliasaro, Sionara; CáCeres, Marcela Eugenia da Silva (2014). "Three new Diorygma ( Graphidaceae ) species from Brazil, with a revised world key". The Lichenologist. 46 (6): 753–761. doi:10.1017/S002428291400036X. S2CID   86972939.
  11. ↑ Barcenas Peña, Alejandrina; LüCking, Robert; Miranda-GonzáLez, Ricardo; Herrera-Campos, María de los Angeles (2014). "Three new species of Graphis (Ascomycota:Ostropales:Graphidaceae) from Mexico, with updates to taxonomic key entries for 41 species described between 2009 and 2013". The Lichenologist. 46 (1): 69–82. doi:10.1017/S0024282913000637. S2CID   87350904.
  12. ↑ Elix, J.A.; Johnston, J. (1986). "New species of Paraparmelia (Lichenised Ascomycotina) from Australia and New Zealand". Brunonia. 9 (2): 139–153. doi:10.1071/BRU9860139.
  13. ↑ dela Cruz, Thomas Edison E.; Timbreza, Lawrence P.; Sangvichien, Ek; Notarte, Kin Israel R.; Santiago, Krystle Angelique A. (2023). "Comparative study on the antimicrobial activities and metabolic profiles of five Usnea species from the Philippines". Journal of Fungi. 9 (11): e1117. doi: 10.3390/jof9111117 . PMC   10672636 . PMID   37998922.
  14. ↑ Elix, J.A.; Armstrong, P.M. (1983). "Further new species of Parmelia subgen. Xanthoparmelia (lichens) from Australia and New Zealand". Australian Journal of Botany. 31 (5): 467–483. doi:10.1071/BT9830467.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.