Polyalthic acid
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| Category | Others |
| Catalog number | BBF-04917 |
| CAS | 1235-76-3 |
| Molecular Weight | 316.43 |
| Molecular Formula | C20H28O3 |
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Description
Polyalthic acid is a naturally occurring diterpene found in copaiba oil and is reported to have anti-tumor activity.
Specification
| IUPAC Name | (1S,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid |
| Canonical SMILES | CC12CCCC(C1CCC(=C)C2CCC3=COC=C3)(C)C(=O)O |
| InChI | InChI=1S/C20H28O3/c1-14-5-8-17-19(2,10-4-11-20(17,3)18(21)22)16(14)7-6-15-9-12-23-13-15/h9,12-13,16-17H,1,4-8,10-11H2,2-3H3,(H,21,22)/t16-,17+,19+,20+/m1/s1 |
| InChI Key | ZQHJXKYYELWEOK-UMGGQSCQSA-N |
Properties
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
Reference Reading
1. Evaluation of the Antinociceptive, Antiallodynic, Antihyperalgesic and Anti-Inflammatory Effect of Polyalthic Acid
Juan Rodríguez-Silverio, María Elena Sánchez-Mendoza, Héctor Isaac Rocha-González, Juan Gerardo Reyes-García, Francisco Javier Flores-Murrieta, Yaraset López-Lorenzo, Geovanna Nallely Quiñonez-Bastidas, Jesús Arrieta Molecules. 2021 May 14;26(10):2921. doi: 10.3390/molecules26102921.
Nonsteroidal anti-inflammatory drugs (NSAIDs) are very commonly used, but their adverse effects warrant investigating new therapeutic alternatives. Polyalthic acid, a labdane-type diterpenoid, is known to produce gastroprotection, tracheal smooth muscle relaxation, and antitumoral, antiparasitic and antibacterial activity. This study aimed to evaluate the antinociceptive, antiallodynic, antihyperalgesic and anti-inflammatory effect of polyalthic acid on rats. Moreover, the effectiveness of treating hyperalgesia with a combination of polyalthic acid and naproxen was analyzed, as well as the type of drug-drug interaction involved. Nociception was examined by injecting 1% formalin into the right hind paw and thermal hyperalgesia and inflammation by injecting a 1% carrageenan solution into the left hind paw of rats. Allodynia was assessed on an L5/L6 spinal nerve ligation model. Polyalthic acid generated significant antinociceptive (56-320 mg/kg), antiallodynic (100-562 mg/kg), and antihyperalgesic and anti-inflammatory (10-178 mg/kg) effects. Antinociception mechanisms were explored by pretreating the rats with naltrexone, ODQ and methiothepin, finding the effect blocked by the former two compounds, which indicates the participation of opioid receptors and guanylate cyclase. An isobolographic analysis suggests synergism between polyalthic acid and naproxen in the combined treatment of hyperalgesia.
2. New antifungal ent-labdane diterpenes against Candida glabrata produced by microbial transformation of ent-polyalthic acid
Ingrid Pontes de Sousa, Antônio Gilberto Ferreira, Antônio Eduardo Miller Crotti, Raquel Alves Dos Santos, Josef Kiermaier, Birgit Kraus, Jörg Heilmann, Niege Araçari Jacometti Cardoso Furtado Bioorg Chem. 2020 Jan;95:103560. doi: 10.1016/j.bioorg.2019.103560. Epub 2019 Dec 28.
Candida glabrata, the most common non-albicans Candida species and one of the primary causes of candidemia, exhibits decreased susceptibility to azoles and more recently to echinocandins. Polyalthic acid 1, a furan diterpene, has been shown promising biological potential and in this study ent-polyalthic acid derivatives with antifungal activity against Candida glabrata were produced by microbial transformation. Incubation of 1 with Aspergillus brasiliensis afforded two known (compounds 5 and 10) and eight new derivatives (compounds 2-4, 6-9 and 11). The most common reaction was hydroxylation, but isomerization of the double bond and acetylation were also detected. None of the tested compounds showed cytotoxicity against HeLa, MCF-7 and MCF-10A cell lines showing IC50 values ranging from 62.6 µM to > 500 µM. Compounds 1, 5, 6, 8 and 11 showed fungistatic effects (ranging from 34.1 µM to 39.5 µM) on C. glabrata at lower concentrations than fluconazole (163.2 µM). Compounds 1, 6 and 8 were more potent fungicides (ranging from 79.0 to 143.6 µM) than fluconazole, which showed fungicidal effect at concentrations higher than 163.2 µM. These results suggest that ent-polyalthic acid and some of its derivatives could be used as lead compounds to develop new antifungal agents.
3. Detailed 1 H and 13 C NMR structural assignment of ent-polyalthic acid, a biologically active labdane diterpene
Pedro Y Kovatch, Alexsandro E Ferreira, Guilherme M L Ghizonni, Sérgio R Ambrósio, Antônio E M Crotti, Vladimir C G Heleno Magn Reson Chem. 2022 Feb;60(2):255-260. doi: 10.1002/mrc.5217. Epub 2021 Sep 20.
In this paper, a complete 1 H and 13 C NMR data assignment of ent-polyalthic acid, a biologically active labdane-type diterpene, is presented. The assignments were carried on the basis of spectroscopic data from 1 H NMR, 13 C{1 H} NMR, gCOSY, gHMQC, and gHMBC experiments. Furthermore, a software-assisted methodology, using FOMSC3_rm_NB and NMR_MultSim programs, supported the detailed and unequivocal assignment of 1 H and 13 C signals, allowing all hydrogen coupling constants to be determined and thus clarifying all hydrogen signal multiplicities.
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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 ╳
