Consalazinic acid

Consalazinic acid
Names
	IUPAC name 5,13,17-trihydroxy-4,12-bis(hydroxymethyl)-7-methyl-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
	Other names 1,4,10-Trihydroxy-5,11-bis(hydroxymethyl)-8-methyl-7H-isobenzofuro[4,5-b][1,4]benzodioxepin-3,7(1H)-dione
Identifiers
CAS Number	77292-23-0;
3D model (JSmol)	Interactive image;
PubChem CID	162888949;
	InChI InChI=1S/C18H14O10/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/h2,18-22,25H,3-4H2,1H3 Key: VHKZGPSNCSPDGX-UHFFFAOYSA-N;
	SMILES CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C4=C(C(=C3CO)O)C(=O)OC4O)CO)O;
Properties
Chemical formula	C18H14O10
Molar mass	390.300 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

Consalazinic acid is a chemical compound with the molecular formula C₁₈H₁₄O₁₀. It is classified as a depsidone and is a secondary metabolite produced by a variety of lichens.

Consalazinic acid was first isolated from Parmotrema subisidiosum and described in 1980.^[1]^[2] It has since been identified in many other lichens.^[3]^[4]^[5]^[6]^[7]^[8]^[9]

References

↑ 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.
↑ 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.
↑ Skult, Henrik (1984). "The Parmelia omphalodes (Ascomycetes) complex in Eastern Fennoscandia. Chemical and morphological variation". Annales Botanici Fennici. 21 (2): 117–142.
↑ Huneck, S.; Kalb, K. (1990). "Chemistry of South African lichens". Pharmazie. 45 (4): 297.{{cite journal}}: CS1 maint: multiple names: authors list (link)
↑ Feige, G.B.; Lumbsch, H.T.; Huneck, S.; Elix, J.A. (1993). "Identification of lichen substances by a standardized high-performance liquid chromatographic method". Journal of Chromatography A. 646 (2): 417–427. doi:10.1016/0021-9673(93)83356-W.
↑ Narui, Takao; Culberson, Chicita F.; Culberson, William Louis; Johnson, Anita; Shibata, Shoji (1996). "A Contribution to the Chemistry of the Lichen Family Umbilicariaceae (Ascomycotina)". The Bryologist. 99 (2): 199–211. doi:10.2307/3244550. JSTOR 3244550.
↑ Stocker-Wörgötter, Elfie; Elix, John A.; Grube, Martin (2004). "Secondary Chemistry of Lichen-forming Fungi: Chemosyndromic Variation and DNA-analyses of Cultures and Chemotypes in the Ramalina farinacea Complex". The Bryologist. 107 (2): 152. doi:10.1639/0007-2745(2004)107[0152:SCOLFC]2.0.CO;2. ISSN 0007-2745.
↑ Torres-Benítez, Alfredo; Rivera-Montalvo, María; Sepúlveda, Beatriz; Castro, Olivio; Nagles, Edgar; Simirgiotis, Mario; García-Beltrán, Olimpo; Areche, Carlos (2017). "Metabolomic Analysis of Two Parmotrema Lichens: P. Robustum (Degel.) Hale and P. Andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS". Molecules. 22 (11): 1861. doi:10.3390/molecules22111861. PMC 6150355. PMID 29084151.
↑ Kumar, K.; Siva, Bandi; Sarma, V.U.M.; Mohabe, Satish; Reddy, A. Madhusudana; Boustie, Joel; Tiwari, Ashok K.; Rao, N. Rama; Babu, K. Suresh (2018). "UPLC–MS/MS quantitative analysis and structural fragmentation study of five Parmotrema lichens from the Eastern Ghats" (PDF). Journal of Pharmaceutical and Biomedical Analysis. 156: 45–57. doi:10.1016/j.jpba.2018.04.017. PMID 29689468.

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[1] 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.

[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.

[3] Skult, Henrik (1984). "The Parmelia omphalodes (Ascomycetes) complex in Eastern Fennoscandia. Chemical and morphological variation". Annales Botanici Fennici. 21 (2): 117–142.

[4] Huneck, S.; Kalb, K. (1990). "Chemistry of South African lichens". Pharmazie. 45 (4): 297.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[5] Feige, G.B.; Lumbsch, H.T.; Huneck, S.; Elix, J.A. (1993). "Identification of lichen substances by a standardized high-performance liquid chromatographic method". Journal of Chromatography A. 646 (2): 417–427. doi:10.1016/0021-9673(93)83356-W.

[6] Narui, Takao; Culberson, Chicita F.; Culberson, William Louis; Johnson, Anita; Shibata, Shoji (1996). "A Contribution to the Chemistry of the Lichen Family Umbilicariaceae (Ascomycotina)". The Bryologist. 99 (2): 199–211. doi:10.2307/3244550. JSTOR 3244550.

[7] Stocker-Wörgötter, Elfie; Elix, John A.; Grube, Martin (2004). "Secondary Chemistry of Lichen-forming Fungi: Chemosyndromic Variation and DNA-analyses of Cultures and Chemotypes in the Ramalina farinacea Complex". The Bryologist. 107 (2): 152. doi:10.1639/0007-2745(2004)107[0152:SCOLFC]2.0.CO;2. ISSN 0007-2745.

[8] Torres-Benítez, Alfredo; Rivera-Montalvo, María; Sepúlveda, Beatriz; Castro, Olivio; Nagles, Edgar; Simirgiotis, Mario; García-Beltrán, Olimpo; Areche, Carlos (2017). "Metabolomic Analysis of Two Parmotrema Lichens: P. Robustum (Degel.) Hale and P. Andinum (Mull. Arg.) Hale Using UHPLC-ESI-OT-MS-MS". Molecules. 22 (11): 1861. doi:10.3390/molecules22111861. PMC 6150355. PMID 29084151.

[9] Kumar, K.; Siva, Bandi; Sarma, V.U.M.; Mohabe, Satish; Reddy, A. Madhusudana; Boustie, Joel; Tiwari, Ashok K.; Rao, N. Rama; Babu, K. Suresh (2018). "UPLC–MS/MS quantitative analysis and structural fragmentation study of five Parmotrema lichens from the Eastern Ghats" (PDF). Journal of Pharmaceutical and Biomedical Analysis. 156: 45–57. doi:10.1016/j.jpba.2018.04.017. PMID 29689468.

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References