Methyl haematommate
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| Category | Others |
| Catalog number | BBF-05146 |
| CAS | 34874-90-3 |
| Molecular Weight | 210.18 |
| Molecular Formula | C10H10O5 |
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Description
Methyl haematommate is an antifungal agent isolated from Stereocaulon ramulosum.
Specification
| Synonyms | Methyl 3-formylorsellinate; Isophthalaldehydic acid, 2,4-dihydroxy-6-methyl-, methyl ester (6CI,7CI) |
| IUPAC Name | methyl 3-formyl-2,4-dihydroxy-6-methylbenzoate |
| Canonical SMILES | CC1=CC(=C(C(=C1C(=O)OC)O)C=O)O |
| InChI | InChI=1S/C10H10O5/c1-5-3-7(12)6(4-11)9(13)8(5)10(14)15-2/h3-4,12-13H,1-2H3 |
| InChI Key | PXFMUVDLJWXOQM-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 298.8±40.0°C (Predicted) |
| Melting Point | 146°C |
| Density | 1.381±0.06 g/cm3 (Predicted) |
Reference Reading
1. Two new phenolic compounds from the lichen Parmotrema cristiferum growing in Vietnam
Nguyen-Kim-Tuyen Pham, Huy Truong Nguyen, Thi-Bich-Ngoc Dao, Kim Long Vu-Huynh, Thi-Quynh-Trang Nguyen, Bui-Linh-Chi Huynh, Tien-Dung Le, Ngoc-Hung Nguyen, Ngoc-Hong Nguyen, Thuc-Huy Duong Nat Prod Res. 2022 Aug;36(15):3865-3871. doi: 10.1080/14786419.2021.1892672. Epub 2021 Mar 3.
Two new phenolic compounds, cristiferides A-B (1-2) together with six known compounds, 2,4-dihydroxyphthalide (3), lecanoric acid (4), orsellinic acid (5), 5-chloroorsellinic acid (6), methyl haematommate (7), and methyl β-orsellinate (8) were isolated from the lichen Parmotrema cristiferum (Taylor) Hale (Parmeliaceae). The structures of isolated compounds were identified from its spectroscopic data and by comparison with the literatures. Compounds 1-3 and 6-8 were evaluated for alpha-glucosidase inhibition. Compounds 2 and 7 revealed potent activity with IC50 values of 72.66 μM and 48.73 μM, respectively.
2. Antioxidant activity and enzymatic of lichen substances: A study based on cyclic voltammetry and theoretical
Osvaldo Yañez, Manuel I Osorio, Edison Osorio, William Tiznado, Lina Ruíz, Camilo García, Orlando Nagles, Mario J Simirgiotis, Grover Castañeta, Carlos Areche, Olimpo García-Beltrán Chem Biol Interact. 2023 Feb 25;372:110357. doi: 10.1016/j.cbi.2023.110357. Epub 2023 Jan 21.
The antioxidant activity of nine lichen substances, including methylatrarate (1), methyl haematommate (2), lobaric acid (3), fumarprotocetraric acid (4), sphaerophorin (5), subsphaeric acid (6), diffractaic acid (7), barbatolic acid (8) and salazinic acid (9) has been determined through cyclic voltammetry. The compounds 1-4 presented slopes close to the Nernst constant of 0.059 V, indicating a 2H+/2e- relation between protons and electrons, as long as the compounds 5, 6, 7, 8, and 9 present slopes between 0.037 V and 0.032 V, indicating a 1H+/2e- relation between protons and electrons. These results show a high free radical scavenging activity by means of the release of H+, suggesting an important antioxidant capacity of these molecules. Theoretical calculations of hydrogen bond dissociation enthalpies (BDE), proton affinities (PA), and Proton Transfer (PT) mechanisms, at M06-2x/6-311+G(d,p) level complement the experimental results. Computations support that the best antioxidant activity is obtained for the molecules (3, 4, 5, 6, 7 and 8), that have a carboxylic acid group close to a phenolic hydroxyl group, through hydrogen atomic transfer (HAT) and sequential proton loss electron transfer (SPLET) mechanisms. Additional computations were performed for modelling binding affinity of the lichen substances with CYPs enzymes, mainly CYP1A2, CYP51, and CYP2C9*2 isoforms, showing strong affinity for all the compounds described in this study.
3. Evaluation of the anticancer potential of secondary metabolites from Pseudevernia furfuracea based on epidermal growth factor receptor inhibition
Rishu Kalra, Xavier A Conlan, Manish Gupta, Carlos Areche, Mamta Bhat, Mayurika Goel Nat Prod Res. 2022 Dec;36(24):6439-6442. doi: 10.1080/14786419.2022.2037587. Epub 2022 Feb 11.
UHPLC/ESI/MS/MS profiling followed by bioactivity guided isolation of Pseudevernia furfuracea (P. furfuracea) extract yielded two polyphenolic molecules, Methyl haematommate (PF-1) and Atraric acid (PF-2). These molecules were evaluated for bioactivity against five cancerous cell lines. The results revealed that atraric acid showed significant activity against ovarian cancer cell line (PA-1) having GI50 at 16.42 µg/mL and moderate activity against the breast cancer cell line (MCF-7), having GI50 at 64.35 µg/mL. The results were further supported by in silico molecular docking studies of atraric acid with the epidermal growth factor receptor (EGFR) tyrosine kinase protein. The study revealed that atraric acid has the capacity to act as a potential EGFR inhibitor via occupying the ATP binding pocket of EGFR and making favourable electrostatic interactions and van der Waals interaction with its key residues. Our results highlight P. furfuracea and its polyphenolic compound, atraric acid as a promising candidate for ovarian cancer management.
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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 ╳
