Constictic acid

Last updated
Constictic acid
Constictic acid.svg
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C19H14O10/c1-6-3-9(26-2)7(4-20)14-10(6)17(23)28-15-8(5-21)13(22)11-12(16(15)27-14)19(25)29-18(11)24/h3-4,19,21-22,25H,5H2,1-2H3
    Key: FYPCEUKJORJHDL-UHFFFAOYSA-N
  • CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3CO)O)C(=O)OC4O)C=O)OC
Properties
C19H14O10
Molar mass 402.311 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Constictic acid is a chemical compound of the depsidone class. It was first isolated in 1968 from lichen of the genus Usnea . [1] It has since been found in many other lichen genera including Menegazzia , [2] Crespoa , [3] and Xanthoparmelia . [4]

Related Research Articles

<i>Xanthoparmelia</i> Genus of fungi

Xanthoparmelia is a genus of foliose lichen in the family Parmeliaceae. Xanthoparmelia is synonymous with Almbornia, Neofuscelia, Chondropsis, Namakwa, Paraparmelia, and Xanthomaculina. This genus of lichen is commonly found in the United States, as well as Australia, New Zealand and Ecuador.

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

Lecanoric acid is a chemical produced by several species of lichen. Lecanoric acid is classified as a polyphenol and a didepside and it functions as an antioxidant. The acid is named after the lichen Lecanora. The acid has also been isolated from Usnea subvacata, Parmotrema stuppuem, Parmotrema tinctorum,Parmotrema grayana, Xanthoparmelia arida and Xanthoparmelia lecanorica. A related compound, 5-chlorolecanoric acid, is found in some species of Punctelia.

<i>Crespoa</i> Genus of fungi

Crespoa is a genus of five species of lichen in the family Parmeliaceae. Species in this genus are characterized by having an upper thallus surface that is wrinkled and reticulately ridged to coarsely foveolate.

John Alan (Jack) Elix emeritus professor in chemistry at the Australian National University, is an organic chemist who has contributed in many fields: lichenology, lichen chemotaxonomy, plant physiology and biodiversity and natural product chemistry. He has authored 2282 species names, and 67 genera in the field of mycology.

<span class="mw-page-title-main">Constipatic acid</span> 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.

Menegazzia fortuita is a species of foliose lichen in the family Parmeliaceae. Found in Australia, it was described as a new species in 2017 by lichenologists John Elix and Patrick McCarthy. The type specimen was collected in Morton National Park where it was found in an open rocky ridge growing on sandstone. The specific epithet fortuita refers to its discovery: "an unplanned field-stop that led to the discovery of the most recent collection which, fortuitously, helped to resolve the identity of several older, unnamed specimens". The lichen is known to occur only in a few locations in Morton National Park where it grows on sandstone in open Eucalyptus woodland. The expected results for standard chemical spot tests are cortex K+ (yellow); medulla K+ (yellow), C−, KC−; P+ (yellow-orange). Menegazzia fortuita contains several secondary chemicals: stictic acid as a major component, atranorin and constictic acid as minor components, and trace amounts of peristictic acid, cryptostictic acid, and menegazziaic acid.

<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.

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.

Ramboldia blastidiata is a species of saxicolous (rock-dwelling) and crustose lichen in the family Lecanoraceae. Found in Australia, it was formally described as a new species in 2007 by lichenologists Gintaras Kantvilas and John Elix. The type specimen was collected by the first author from the western slopes of Strzelecki Peaks on Flinders Island (Tasmania) at an altitude of 150 m (490 ft); here, in dry sclerophyll forest, it was found growing on a granite boulder. The lichen forms pale grey-green, olive-green to dull olive-brown crust-like patches up to 30 cm (12 in) wide. The authors suggest that it is widespread in temperate Australia and Tasmania, but not commonly collected. Others saxicolous lichens that it usually grows with include Ramboldia petraeoides, Lecanora farinacea, Xanthoparmelia mougeotina, and species from the genera Buellia and Rhizocarpon. The specific epithet blastidiata refers to the presence of blastidia, which are vegetative propagules that contain mycobiont and photobiont and are produced by yeast-like budding.

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.

Xanthoparmelia bainskloofensis is a species of saxicolous (rock-dwelling), foliose lichen in the family Parmeliaceae. It was formally described as a new species in 2002 by lichenologists John Elix and Thomas Hawkes Nash III. The type specimen was collected by Nash from Bainskloof Pass at an altitude of 600 m (2,000 ft), where it was found growing on acidic rock. The species epithet refers to the type locality, the only place the lichen is known to occur. It contains usnic acid as a major lichen product, and minor amounts of echinocarpic acid, conechinocarpic acid, and hypothamnolic acid.

Xanthoparmelia boyeri is a species of foliose lichen in the family Parmeliaceae. Found in Kenya, it was formally described as a new species in 2002 by Australian lichenologist John Elix. The type specimen was collected from the Lewis Glacier on Mount Kenya, where it was found growing on volcanic rock. The species epithet refers to M. Boyer, one of the collectors of the type. The lichen contains salazinic acid as a major lichen product, minor amounts of usnic acid and norstictic acid, and trace amounts of consalazinic acid.

Xanthoparmelia dubitella 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 Cape of Good Hope Nature Reserve, where it was found growing as small, somewhat crustose rosettes on rocks and boulders. It is only known from the type collection. The lichen contains norlobaridone as a major product, minor amounts of usnic acid and connorlobaridone, and trace amounts of loxodin. The species epithet refers to its resemblance to Xanthoparmelia dubitata, which is distinguished by its larger thalli, broader lobes, and a lower surface that is pale tan to brown in colour.

Xanthoparmelia kleinswartbergensis 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 Klein Swartberg, where it was found growing on large boulders in a gorge. It contains protocetraric acid as a major lichen product, minor amounts of usnic acid and anhydrofusarubin lactol, and trace amounts of anhydrofusarubin lactol methyl ketal. The species epithet refers to the type locality, the only place the lichen is known to occur.

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.

Xanthoparmelia perezdepazii is a species of saxicolous (rock-dwelling), foliose lichen in the family Parmeliaceae. It is found in the Canary Islands.

References

  1. Yosioka, Itiro; Morita, Yutaka; Ebihara, Kikuko (1970). "The Structure of Constictic Acid". Chemical and Pharmaceutical Bulletin. 18 (11): 2364–2366. doi:10.1248/cpb.18.2364.
  2. McCarthy, P.M.; Elix, John A. (2018). "New species and records of lichens from the Cook Islands" (PDF). Australian Lichenology. 82: 1.
  3. Hawksworth, David L. (2011). "Parmotrema subgen. Crespoa subgen. nov. for the Canoparmelia crozalsiana clade". Lichenologist. 43 (6): 647–648. doi:10.1017/S0024282911000399. S2CID   86356671.
  4. Blanco, Oscar; Crespo, Ana; Elix, John A. (2005). "Two new species of Xanthoparmelia (Ascomycota: Parmeliaceae) from Spain". Lichenologist. 37 (2): 97–100. doi:10.1017/S0024282905014829. S2CID   86778304.