Perlatolic acid
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| Category | Others |
| Catalog number | BBF-05434 |
| CAS | 529-47-5 |
| Molecular Weight | 444.52 |
| Molecular Formula | C25H32O7 |
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Specification
| Synonyms | Perlatolinic acid; NSC 646002; beta-Resorcylic acid, 6-pentyl-, 4-(2-hydroxy-6-pentyl-p-anisate); 2-Hydroxy-4-methoxy-6-pentylbenzoic acid, 3-hydroxy-4-carboxy-5-pentylphenyl ester; 4-(2-Hydroxy-4-methoxy-6-pentylbenzoyloxy)-6-pentylsalicylic acid; 4-(2-Pentyl-4-methoxy-6-hydroxybenzoyloxy)-2-hydroxy-6-pentylbenzoic acid; Benzoic acid, 2-hydroxy-4-[(2-hydroxy-4-methoxy-6-pentylbenzoyl)oxy]-6-pentyl- |
| IUPAC Name | 2-hydroxy-4-(2-hydroxy-4-methoxy-6-pentylbenzoyl)oxy-6-pentylbenzoic acid |
| Canonical SMILES | CCCCCC1=C(C(=CC(=C1)OC)O)C(=O)OC2=CC(=C(C(=C2)O)C(=O)O)CCCCC |
| InChI | InChI=1S/C25H32O7/c1-4-6-8-10-16-13-19(15-20(26)22(16)24(28)29)32-25(30)23-17(11-9-7-5-2)12-18(31-3)14-21(23)27/h12-15,26-27H,4-11H2,1-3H3,(H,28,29) |
| InChI Key | UTAQXQVSEKIWBB-UHFFFAOYSA-N |
Properties
| Boiling Point | 613°C at 760 mmHg |
| Density | 1.198 g/cm3 |
Reference Reading
1. New Species and New Records of Buellia (Lichenized Ascomycetes) from Jeju Province, South Korea
Xin Yu Wang, Dong Liu, László Lőkös, Sergey Y Kondratyuk, Soon-Ok Oh, Jung Shin Park, Jae-Seoun Hur Mycobiology. 2016 Mar;44(1):14-20. doi: 10.5941/MYCO.2016.44.1.14. Epub 2016 Mar 31.
A new species and 2 new records of lichen genus Buellia were discovered from Chuja-do Island in Jeju Province during a recent floristic survey: B. chujana X. Y. Wang, S. Y. Kondr., L. Lőkös & J.-S. Hur sp. nov., B. halonia (Ach.) Tuck., and B. mamillana (Tuck.) W. A. Weber. The new species is characterized by a brown, areolate thallus, the presence of perlatolic acid, and a saxicolous habitat. Together with previously recorded species, 10 Buellia species were confirmed from Jeju-do Island. Among these species, 3 growing in the exposed rocky area contained xanthone (yellowish lichen thallus, UV + orange), indicating that production of xanthone in this genus might be a defense strategy against the harm of UV light. Although the genus Buellia has been thoroughly studied in Korea before, novel species have been discovered continuously, and large species diversity has been found in this crustose genus, even from a small rocky island. This study indicates that the coastal area harbors a vast number of crustose lichen species, and there is great potential to discover unknown lichens in the coastal rocky area in Korea.
2. Interaction between lichen secondary metabolites and antibiotics against clinical isolates methicillin-resistant Staphylococcus aureus strains
Pierangelo Bellio, Bernardetta Segatore, Alisia Mancini, Letizia Di Pietro, Carlo Bottoni, Alessia Sabatini, Fabrizia Brisdelli, Marisa Piovano, Marcello Nicoletti, Gianfranco Amicosante, Mariagrazia Perilli, Giuseppe Celenza Phytomedicine. 2015 Feb 15;22(2):223-30. doi: 10.1016/j.phymed.2014.12.005. Epub 2014 Dec 19.
The in vitro antimicrobial activities of five compounds isolated from lichens, collected in several Southern regions of Chile (including the Chilean Antarctic Territory), were evaluated alone and in combination with five therapeutically available antibiotics, using checkerboard microdilution assay against methicillin-resistant clinical isolates strains of Staphylococcus aureus. MIC90, MIC50, as well as MBC90 and MBC50, for the lichen compounds were evaluated. The MIC90 was ranging from 32 µg/ml for perlatolic acid to 128 µg/ml for α-collatolic acid. MBC90 was ranging from onefold up to twofold the MIC90 for each compound. A synergistic action was observed in combination with gentamicin, whilst antagonism was observed for some lichen compounds in combination with levofloxacin. All combinations with erythromycin were indifferent, whilst variability was observed for clindamycin and oxacillin combinations. Data from checkerboard assay were analysed and interpreted using the fractional inhibitory concentration index and the response surface approach using the ΔE model. Discrepancies were found between both methods for some combinations. These could mainly be explained by the failure of FIC approach, being too much subjective and sensitive to experimental errors. These findings suggest, however, that the natural compounds from lichens are good candidates for the individuation of novel templates for the development of new antimicrobial agents or combinations of drugs for chemotherapy.
3. Lichen-derived compounds show potential for central nervous system therapeutics
R Gajendra Reddy, Lenin Veeraval, Swati Maitra, Marylène Chollet-Krugler, Sophie Tomasi, Françoise Lohézic-Le Dévéhat, Joël Boustie, Sumana Chakravarty Phytomedicine. 2016 Nov 15;23(12):1527-1534. doi: 10.1016/j.phymed.2016.08.010. Epub 2016 Aug 31.
Background: Natural products from lichens are widely investigated for their biological properties, yet their potential as central nervous system (CNS) therapeutic agents is less explored. Purpose: The present study investigated the neuroactive properties of selected lichen compounds (atranorin, perlatolic acid, physodic acid and usnic acid), for their neurotrophic, neurogenic and acetylcholine esterase (AChE) activities. Methods: Neurotrophic activity (neurite outgrowth) was determined using murine neuroblastoma Neuro2A cells. A MTT assay was performed to assess the cytotoxicity of compounds at optimum neurotrophic activity. Neuro2A cells treated with neurotrophic lichen compounds were used for RT-PCR to evaluate the induction of genes that code for the neurotrophic markers BDNF and NGF. Immunoblotting was used to assess acetyl H3 and H4 levels, the epigenetic markers associated with neurotrophic and/or neurogenic activity. The neurogenic property of the compounds was determined using murine hippocampal primary cultures. AChE inhibition activity was performed using a modified Ellman's esterase method. Results: Lichen compounds atranorin, perlatolic acid, physodic acid and (+)-usnic acid showed neurotrophic activity in a preliminary cell-based screening based on Neuro2A neurite outgrowth. Except for usnic acid, no cytotoxic effects were observed for the two depsides (atranorin and perlatolic acid) and the alkyl depsidone (physodic acid). Perlatolic acid appears to be promising, as it also exhibited AChE inhibition activity and potent proneurogenic activity. The neurotrophic lichen compounds (atranorin, perlatolic acid, physodic acid) modulated the gene expression of BDNF and NGF. In addition, perlatolic acid showed increased protein levels of acetyl H3 and H4 in Neuro2A cells. Conclusion: These lichen depsides and depsidones showed neuroactive properties in vitro (Neuro2A cells) and ex vivo (primary neural stem or progenitor cells), suggesting their potential to treat CNS disorders.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
