Tenuiorin
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| Category | Others |
| Catalog number | BBF-05464 |
| CAS | 570-07-0 |
| Molecular Weight | 496.46 |
| Molecular Formula | C26H24O10 |
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Specification
| Synonyms | 2-Hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]-6-methylbenzoic acid 3-hydroxy-4-methoxycarbonyl-5-methylphenyl ester; Peltigerin; Methyl 2-hydroxy-4-({2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]-6-methylbenzoyl}oxy)-6-methylbenzoate; Benzoic acid, 2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]-6-methyl-, 3-hydroxy-4-(methoxycarbonyl)-5-methylphenyl ester |
| IUPAC Name | [3-hydroxy-4-(3-hydroxy-4-methoxycarbonyl-5-methylphenoxy)carbonyl-5-methylphenyl] 2-hydroxy-4-methoxy-6-methylbenzoate |
| Canonical SMILES | CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)OC3=CC(=C(C(=C3)C)C(=O)OC)O)O)O)OC |
| InChI | InChI=1S/C26H24O10/c1-12-6-15(33-4)9-18(27)22(12)25(31)36-17-8-14(3)23(20(29)11-17)26(32)35-16-7-13(2)21(19(28)10-16)24(30)34-5/h6-11,27-29H,1-5H3 |
| InChI Key | HTOPMCGBOADATG-UHFFFAOYSA-N |
Properties
| Boiling Point | 642.2±55.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Chemical profile and biological activities of Peltigera horizontalis (Hudson) Baumg. thallus and apothecia extracts
Gordana Stojanović, Ivana Zrnzević, Ivana Zlatanović, Miroslava Stanković, Vesna Stankov Jovanović, Violeta Mitić, Aleksandra Đorđević Nat Prod Res. 2020 Feb;34(4):549-552. doi: 10.1080/14786419.2018.1489386. Epub 2018 Nov 16.
The aim of this study was to determine, for the first time, the chemical composition of Peltigera horizontalis thallus and apothecia extracts (ether, ethyl acetate, dichloromethane and acetone) by HPLC-UV and GC-MS, and evaluate activity of genotoxic, anticholinesterase, antioxidant and antibacterial potential of acetone extracts. Major constituents of thallus extracts were gyrophoric acid, and methyl gyrophorate while dominant component of apothecia extracts was tenuiorin. The predominant volatile compounds in extracts were methyl orsellinate, dodecyl acrylate, orcinol and orcinol monomethyl ether. The thallus acetone extract at concentration of 2.0 µg mL-1 gave the greatest decrease in the micronuclei frequency (22.4%) of all tested extracts. Apothecia extract showed stronger antioxidant activity as compared to thallus extract. Tested extracts at concentration of 10 mg mL-1 exhibited inhibitory effect (16.5% for thallus and 12.8% for apothecia) on pooled human serum cholinesterase. P. horizontalis acetone extracts had no activity against the tested five bacteria strains.
2. Mass Spectrometry Imaging of Specialized Metabolites for Predicting Lichen Fitness and Snail Foraging
Alice Gadea, Mathieu Fanuel, Anne-Cécile Le Lamer, Joël Boustie, Hélène Rogniaux, Maryvonne Charrier, Françoise Lohézic-Le Devehat Plants (Basel). 2020 Jan 6;9(1):70. doi: 10.3390/plants9010070.
Lichens are slow-growing organisms supposed to synthetize specialized metabolites to protect themselves against diverse grazers. As predicted by the optimal defense theory (ODT), lichens are expected to invest specialized metabolites in higher levels in reproductive tissues compared to thallus. We investigated whether Laser Desorption Ionization coupled to Mass Spectrometry Imaging (LDI-MSI) could be a relevant tool for chemical ecology issues such as ODT. In the present study, this method was applied to cross-sections of thalli and reproductive tissues of the lichen Pseudocyphellaria crocata. Spatial mapping revealed phenolic families of metabolites. A quantification of these metabolites was carried out in addition to spatial imaging. By this method, accumulation of specialized metabolites was observed in both reproductive parts (apothecia and soralia) of P. crocata, but their nature depended on the lichen organs: apothecia concentrated norstictic acid, tenuiorin, and pulvinic acid derivatives, whereas soralia mainly contained tenuiorin and pulvinic acid. Stictic acid, tenuiorin and calycin, tested in no-choices feeding experiments, were deterrent for N. hookeri while entire thalli were consumed by the snail. To improve better knowledge in relationships between grazed and grazing organisms, LDI-MSI appears to be a complementary tool in ecological studies.
3. Continental and Antarctic Lichens: isolation, identification and molecular modeling of the depside tenuiorin from the Antarctic lichen Umbilicaria antarctica as tau protein inhibitor
Francisco Salgado, Julio Caballero, Reinaldo Vargas, Alberto Cornejo, Carlos Areche Nat Prod Res. 2020 Mar;34(5):646-650. doi: 10.1080/14786419.2018.1492576. Epub 2018 Nov 2.
Alzheimer's disease (AD) is the most common form of dementia involving Aβ and tau protein. So far, AD cure remains elusive, but considering that AD progresses throughout tau pathology, which turns tau protein an appropriate target, besides tau is also included in other neurodegenerative disorders named as tauopathies. Here, we have isolated seventeen compounds belonging to six lichens species. Due to scarce of spectroscopic data of the compound 5,7-dihydroxy-6-methylphthalide, we explained their structural elucidation based on NMR data. In this study, we show that only tenuiorin from Umbilicaria antarctica inhibited 50% of tau 4R at 100 µM. Then, we shown that molecular interactions of tenuiorin with the steric zipper model of the hexapeptide 306VQIVYK311 were studied by docking calculations and the results suggested that tenuiorin forms both hydrogen bonds with lysine and glutamine side chains and forms several hydrophobic interactions with valine and lysine from 306VQIVYK311 motif.
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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
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
