Constipatic acid

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Constipatic acid
Constipatic acid.svg
Names
IUPAC name
2-(14'-hydroxypentadecyl)-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C21H36O5/c1-16(22)14-12-10-8-6-4-3-5-7-9-11-13-15-18-19(20(23)24)17(2)21(25)26-18/h16,18,22H,3-15H2,1-2H3,(H,23,24)
    Key: RJNPNSFGRBJXHX-UHFFFAOYSA-N
  • CC(O)CCCCCCCCCCCCCC1OC(=O)C(=C1C(O)=O)C
Properties
C21H36O5
Molar mass 368.514 g·mol−1
Appearancewhite flakes
Melting point 108–109°
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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 (after which the compound is named), which was collected on schist boulders west of Springton, South Australia. The related compounds protoconstipatic acid and dehydroconstipatic acid were also reported concurrently. [1] 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. [2]

After conversion of constipatic acid to methyl constipatate, a mass spectra of the compound revealed four diagnostic peaks at the mass-to-charge ratio (m/e) of 367, 338, 279 and 169. The peaks correspond to the cleavage of a methyl group, the 1-hydroxyethyl moiety, the methoxycarbonyl group (i.e. CH3-O-CO-) and 1-cleavage of the side chain. Additional analysis with proton nuclear magnetic resonance corroborated these results and confirmed the linear nature of the aliphatic chain. [1]

In addition to Xanthoparmelia constipata, constipatic acid has been isolated from several other Xanthoparmelia species, including X. perezdepazii , [3] X. filarskyana , X. flavecentireagens , X. lineola , and X. metaclystoides . [4] It has been isolated from lichens in other genera as well. Examples include Parmelia xanthosorediata , Heterodermia appendiculata , Heterodermia japonica , [5] Protoparmelia nebulosa , [6] Hertelidea wankaensis , [7] Lepraria coriensis , [8] Punctelia negata , [9] and Rhizoplaca melanophthalma . [10]

Some sources consider the molecule to have an unusual or humorous name due to its similarity to the word "constipation". [11] [12]

See also

Related Research Articles

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<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.

<i>Lepraria</i> Genus of lichens

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Syo Kurokawa was a noted Japanese lichenologist and 1994 recipient of the Acharius Medal. He studied under Mason Hale and Yasuhiko Asahina.

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

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Parmotrema acrotrychum is a species of lichen in the family Parmeliaceae. First discovered in Papua New Guinea, it was originally described in 1979 by Japanese lichenologist Syo Kurokawa as a species of Parmelia. Heinar Streimann transferred it to the genus Parmotrema in 1986. The lichen has also been found in Queensland (Australia) and Malaysia. It has been shown to contain a variety of secondary chemicals, including atranorin, fumarprotocetraric acid, succinprotocetraric acid, chloroatranorin, protocetraric acid, protolichesterinic acid, and lichesterinic acid.

Nipponoparmelia is a genus of five species of lichen belonging to the family Parmeliaceae. Nipponoparmelia was originally conceived by Syo Kurokawa as a subgenus of the genus Parmelia in 1994. It was raised to generic status in 2010. Four east Asian species were originally placed in the genus; Nipponoparmelia perplicata, found in South Korea and Russia, was added in 2014.

<i>Hertelidea</i> Genus of lichens in the family Stereocaulaceae

Hertelidea is a genus of crustose lichens in the family Stereocaulaceae. Characteristics of the genus include carbon-black ring or outer margin (exciple) around the fruit body disc (apothecium), eight-spored, Micarea-type asci and mostly simple, hyaline ascospores that lack a transparent outer layer. Hertelidea species mostly grow on wood, although less frequently they are found on bark or soil. While the type species, Hertelidea botryosa, has a widespread distribution, most of the other species are found only in Australia.

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<i>Punctelia borreri</i> Species of lichen

Punctelia borreri is a species of foliose lichen in the family Parmeliaceae. It is a common and widely distributed species, occurring in tropical, subtropical, and temperate regions of Africa, Asia, Europe, North America, Oceania, and South America. The lichen typically grows on bark of deciduous trees, and less commonly on rock. Some European countries have reported increases in the geographic range or regional frequency of the lichen in recent decades, attributed alternatively to a reduction of atmospheric sulphur dioxide levels or an increase in temperatures resulting from climate change.

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

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

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

References

  1. 1 2 Chester, Douglas O.; Elix, John A. (1979). "Three new aliphatic acids from lichens of genus Parmelia (Subgenus Xanthoparmelia)". Australian Journal of Chemistry. 32 (11): 2565–2569. doi:10.1071/CH9792565.
  2. ↑ Kurokawa, Syo; Filson, Rex (1975). "New species of Parmelia from South Australia". Bulletin of the National Science Museum (Tokyo). Series B (Botany). 1 (1): 35–47.
  3. ↑ Pérez-Vargas, Israel; Hernández-Padrón, Consuelo; Elix, John A. (2007). "A new species of Xanthoparmelia (Ascomycota: Parmeliaceae) from the Canary Islands". The Lichenologist. 39 (5): 445–449. doi:10.1017/S0024282907007189. S2CID   86682879.
  4. ↑ Stocker-Wörgötter, Elfie (2015). "Biochemical Diversity and Ecology of Lichen-Forming Fungi: Lichen Substances, Chemosyndromic Variation and Origin of Polyketide-Type Metabolites (Biosynthetic Pathways)". In Upreti, Dalip Kumar; Divakar, Pradeep K.; Shukla, Vertika; Bajpai, Rajesh (eds.). Recent Advances in Lichenology. Modern Methods and Approaches in Lichen Systematics and Culture Techniques. Vol. 2. New Delhi: Springer. pp. 161–179. doi:10.1007/978-81-322-2235-4_9. ISBN   978-81-322-2234-7.
  5. ↑ Din, Laily B.; Zakaria, Zuriati; Samsudin, Mohd Wahid; Elix, John A. (2010). "Chemical profile of compounds from lichens of Bukit Larut, Peninsular Malaysia" (PDF). Sains Malaysiana. 39 (6): 901–908.
  6. ↑ Elix, John A.; Kantvilas, Gintaras (2009). "A new species of Protoparmelia (lichenized Ascomycota) from Australia". Nova Hedwigia. 89 (3–4): 355–360. doi:10.1127/0029-5035/2009/0089-0355. hdl: 1885/57211 . S2CID   84989424.
  7. ↑ Kantvilas, Gintaras; Elix, John (2006). "Further notes on the genus Hertelidea, with a description of a new species". Australasian Lichenology. 59: 30–33.
  8. ↑ Joshi, Yogesh; Wang, Xin Yu; Koh, Young Jin; Hur, Jae-Seoun (2010). "The lichen genus Lepraria (Stereocaulaceae) in South Korea". Mycotaxon. 112 (1): 201–217. doi: 10.5248/112.201 .
  9. ↑ Canêz, Luciana S.; Spielmann, Adriano A.; Marcelli, Marcelo P.; Elix, John A. (2016). "An accurate circumscription of the poorly known Punctelia negata (Nyl.) Krog". Iheringia, Série Botânica. 71 (3): 257–260.
  10. ↑ Shrestha, Gajendra; Raphael, Jocelyn; Leavitt, Steven D.; St. Clair, Larry L. (2014). "In vitro evaluation of the antibacterial activity of extracts from 34 species of North American lichens". Pharmaceutical Biology. 52 (10): 1262–1266. doi:10.3109/13880209.2014.889175. PMID   24863278. S2CID   20528049.
  11. ↑ May, Paul (27 March 2019). "Molecules with Silly or Unusual Names". Bristol University. Retrieved 1 April 2021.
  12. ↑ Mestel, Rosie (24 June 2002). "When Scientists Get Silly, Chemical Names Do Too". Los Angeles Times . Retrieved 1 April 2021.
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