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Hypothamnolic acid

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Hypothamnolic acid
Category Others
Catalog number BBF-05465
CAS 573-36-4
Molecular Weight 406.34
Molecular Formula C19H18O10

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Synonyms 1,3-Benzenedicarboxylic acid, 2-hydroxy-4-methoxy-6-methyl-, 1-(3-carboxy-4,6-dihydroxy-2,5-dimethylphenyl) ester; 3-((3-carboxy-2-hydroxy-4-methoxy-6-methylbenzoyl)oxy)-4,6-dihydroxy-2,5-dimethylbenzoic acid; Hypothamnolinsaeure; 2-hydroxy-4-methoxy-6-methyl-isophthalic acid-1-(3-carboxy-4,6-dihydroxy-2,5-dimethyl-phenyl ester)
IUPAC Name 5-(3-carboxy-2-hydroxy-4-methoxy-6-methylbenzoyl)oxy-2,4-dihydroxy-3,6-dimethylbenzoic acid
Canonical SMILES CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2C)C(=O)O)O)C)O)O)C(=O)O)OC
InChI InChI=1S/C19H18O10/c1-6-5-9(28-4)12(18(25)26)15(22)10(6)19(27)29-16-7(2)11(17(23)24)13(20)8(3)14(16)21/h5,20-22H,1-4H3,(H,23,24)(H,25,26)
InChI Key JAMFWYQGSFUDBI-UHFFFAOYSA-N
1. β-Orcinol-type depsides from the lichen Thamnolia vermicularis
Wen-Juan Xiang, Qi-Qi Wang, Lei Ma, Li-Hong Hu Nat Prod Res. 2013;27(9):804-8. doi: 10.1080/14786419.2012.704374. Epub 2012 Jul 16.
A phytochemical investigation of a herb tea made from Thamnolia vermicularis led to the isolation of three new β-orcinol-type depsides (1, 2 and 3), along with seven known compounds hypothamnolic acid (4), 3'-methylevenic acid (5), baeomycesic acid (6), squamatic acid (7), methyl 3'-methyllecanorate (8), barbatinic acid (9) and atranorin (10). The structures of the new compounds were determined on the basis of spectroscopic evidence, including 1-D and 2-D NMR and ESI-MS techniques.
2. Lichen Depsides and Tridepsides: Progress in Pharmacological Approaches
Isabel Ureña-Vacas, Elena González-Burgos, Pradeep Kumar Divakar, María Pilar Gómez-Serranillos J Fungi (Basel). 2023 Jan 14;9(1):116. doi: 10.3390/jof9010116.
Depsides and tridepsides are secondary metabolites found in lichens. In the last 10 years, there has been a growing interest in the pharmacological activity of these compounds. This review aims to discuss the research findings related to the biological effects and mechanisms of action of lichen depsides and tridepsides. The most studied compound is atranorin, followed by gyrophoric acid, diffractaic acid, and lecanoric acid. Antioxidant, cytotoxic, and antimicrobial activities are among the most investigated activities, mainly in in vitro studies, with occasional in silico and in vivo studies. Clinical trials have not been conducted using depsides and tridepsides. Therefore, future research should focus on conducting more in vivo work and clinical trials, as well as on evaluating the other activities. Moreover, despite the significant increase in research work on the pharmacology of depsides and tridepsides, there are many of these compounds which have yet to be investigated (e.g., hiascic acid, lassalic acid, ovoic acid, crustinic acid, and hypothamnolic acid).

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