Connorstictic acid

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Connorstictic acid
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)
  • 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 checkY
    Key: JGHRZZSLOGDYOO-UHFFFAOYSA-N checkY
  • 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.

History[edit]

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[edit]

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[edit]

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]

References[edit]

  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. ^ a b 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. ^ a b 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.
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