Protocetraric acid
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| Category | Bioactive by-products |
| Catalog number | BBF-05408 |
| CAS | 489-51-0 |
| Molecular Weight | 374.30 |
| Molecular Formula | C18H14O9 |
| Purity | ≥98% |
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Description
Protocetraric acid has strong antioxidant, antibacterial and anticancer effects.
Specification
| Synonyms | 11H-Dibenzo(b,e)(1,4)dioxepin-7-carboxylic acid, 4-formyl-3,8-dihydroxy-9-(hydroxymethyl)-1,6-dimethyl-11-oxo-; 10-formyl-3,9-dihydroxy-4-(hydroxymethyl)-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid; Protocetrarsaeure |
| Storage | Store at -20°C |
| IUPAC Name | 4-Formyl-3,8-dihydroxy-9-(hydroxymethyl)-1,6-dimethyl-11-oxo-11H-dibenzo(b,e)(1,4)dioxepin-7-carboxylic acid |
| Canonical SMILES | CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C(=C(C(=C3CO)O)C(=O)O)C)C=O)O |
| InChI | InChI=1S/C18H14O9/c1-6-3-10(21)8(4-19)15-11(6)18(25)27-16-9(5-20)13(22)12(17(23)24)7(2)14(16)26-15/h3-4,20-22H,5H2,1-2H3,(H,23,24) |
| InChI Key | VOXMONAUSQZPTP-UHFFFAOYSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Bacteria |
| Boiling Point | 670.8°C at 760 mmHg |
| Density | 1.628 g/cm3 |
| Solubility | Soluble in Acetone, Chloroform, Dichloromethane, DMSO, Ethyl Acetate |
Reference Reading
1. α-Glucosidase inhibitory derivatives of protocetraric acid
Huu-Hung Nguyen, Thuc-Huy Duong, Tran-Van-Anh Nguyen, Thanh-Hung Do, Duc-Dung Pham, Ngoc-Hong Nguyen, Huy Truong Nguyen Nat Prod Res. 2022 Aug 13;1-12. doi: 10.1080/14786419.2022.2110093. Online ahead of print.
Lichen-derived depsidones have been a successful source for alpha-glucosidase inhibitory agents with numerous advantages. In this article, derivatives of protocetraric acids were designed and synthesised. Diels-Alder reaction, esterification, and Friedel-Crafts alkylation of protocetraric acid with different reagents under Lewis acid were performed. Eleven products were prepared, including 10 new compounds and parmosidone A. Among them, compounds 2-4 and 6 had the novel skeletons. The newly synthetic products were evaluated for alpha-glucosidase inhibition. Among tested compounds, 9 showed the strongest activity, with an IC50 value of 5.9 µM. The molecular docking model indicated the consistency between in vitro and in silico data of alpha-glucosidase inhibition.
2. Quantum chemical calculation studies toward microscopic understanding of retention mechanism of Cs radioisotopes and other alkali metals in lichens
Hiroya Suno, Masahiko Machida, Terumi Dohi, Yoshihito Ohmura Sci Rep. 2021 Apr 15;11(1):8228. doi: 10.1038/s41598-021-87617-w.
We evaluate stability of cesium (Cs) and other alkali-metal cation complexes of lichen metabolites in both gas and aqueous phases to discuss why lichens can retain radioactive Cs in the thalli over several years. We focus on oxalic acid, (+)-usnic acid, atranorin, lecanoric acid, and protocetraric acid, which are common metabolite substances in various lichens including, e.g., Flavoparmelia caperata and Parmotrema tinctorum retaining Cs in Fukushima, Japan. By performing quantum chemical calculations, their gas-phase complexation energies and aqueous-solution complexation free energies with alkali-metal cations are computed for their neutral and deprotonated cases. Consequently, all the molecules are found to energetically favor cation complexations and the preference order is Li[Formula: see text]Na[Formula: see text]K[Formula: see text]Rb[Formula: see text]Cs[Formula: see text] for all conditions, indicating no specific Cs selectivity but strong binding with all alkali cations. Comparing complexation stabilities among these metabolites, lecanoric and protocetraric acids seen in medullary layer are found to keep higher affinity in their neutral case, while (+)-usnic acid and atranorin in upper cortex exhibit rather strong affinity only in deprotonated cases through forming stable six atoms' ring containing alkali cation chelated by two oxygens. These results suggest that the medullary layer can catch all alkali cations in a wide pH range around the physiological one, while the upper cortex can effectively block penetration of metal ions when the metal stress grows. Such insights highlight a physiological role of metabolites like blocking of metal-cation migrations into intracellular tissues, and explain long-term retention of alkali cations including Cs in lichens containing enough such metabolites to bind them.
3. Paresordin A, a new diphenyl cyclic peroxide from the lichen Parmotrema praesorediosum
Bui Linh Chi Huynh, Nguyen Kim Tuyen Pham, Tan Phat Nguyen J Asian Nat Prod Res. 2022 Feb;24(2):190-195. doi: 10.1080/10286020.2021.1908271. Epub 2021 Apr 1.
From the lichen Parmotrema praesorediosum, one new diphenyl peroxide, named praesordin A (1), together with four depsidones, including virensic acid (2), protocetraric acid (3), 8'-O-methylprotocetraric acid (4), and furfuric acid (5) were purified. Their structures were chacracterized using extensive HR-ESI-MS and NMR spectroscopic methods. The isolated compounds (2-5) possessed stronger α-glucosidase inhibitory activity (IC50 = 43.7-110.1 μM) than the standard drug acarbose (IC50 = 214.5 μM).
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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 ╳
