Barbatic acid
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| Category | Others |
| Catalog number | BBF-05003 |
| CAS | 17636-16-7 |
| Molecular Weight | 360.36 |
| Molecular Formula | C19H20O7 |
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Description
Barbatic acid is a substance obtained from Cladia aggregata (lichen), which exhibits schistosomiasis effect on adult Schistosoma mansoni.
Specification
| IUPAC Name | 2-hydroxy-4-(2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy-3,6-dimethylbenzoic acid |
| Canonical SMILES | CC1=CC(=C(C(=C1C(=O)OC2=C(C(=C(C(=C2)C)C(=O)O)O)C)O)C)OC |
| InChI | InChI=1S/C19H20O7/c1-8-7-13(11(4)16(20)14(8)18(22)23)26-19(24)15-9(2)6-12(25-5)10(3)17(15)21/h6-7,20-21H,1-5H3,(H,22,23) |
| InChI Key | NMKBRSYSHBPUPY-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | parasites |
Reference Reading
1. Schistosomicidal effect of divaricatic acid from Canoparmelia texana (Lichen): In vitro evaluation and ultrastructural analysis against adult worms of Schistosoma mansoni
Hianna A M F Silva, André L Aires, Caroline L R Soares, Williams N Siqueira, Maíra V Lima, Mônica C B Martins, Mônica C P A Albuquerque, Teresinha G Silva, Fábio A Brayner, Luiz C Alves, Ana M M A Melo, Nicácio H Silva Acta Trop. 2021 Oct;222:106044. doi: 10.1016/j.actatropica.2021.106044. Epub 2021 Jul 15.
In this study we evaluated the in vitro effect of divaricatic acid against coupled worms of Schistosoma mansoni. The schistosomicidal effect was evaluated through the bioassay of motility and mortality, cellular viability of the worms and ultrastructural analysis through Scanning Electron Microscopy. To evaluate the cytotoxicity of divaricatic acid, a cell viability assay was performed with human peripheral blood mononuclear cells. Divaricatic acid proved effect against S. mansoni after 3 hours of exposure. At the end of 24 h the concentrations of 100 - 200 μM presented lethality to the worms. Motility changes were observed at sublethal concentrations. The IC50 obtained by the cell viability assay for S. mansoni was 100.6 μM (96.24 - 105.2 μM). Extensive damage to the worm's tegument was observed such as peeling, erosion, bubbles, edema, damage and loss of tubercles and spines, fissures and tissue ruptures. No cytotoxicity was observed in human peripheral blood mononuclear cells. This report provides data showing the schistosomicidal effect of divaricatic acid on S. mansoni, causing death, motile changes and ultrastructural damage to worms. In addition, divaricatic acid was shown to be non-toxic to human peripheral blood mononuclear cells at concentrations effective on S. mansoni.
2. Synthesis of barbacic acid
Xiang Yu, Yin-Kai Xi, Guo-Yong Luo, Yi Long, Wu-De Yang J Asian Nat Prod Res. 2022 Dec;24(12):1150-1156. doi: 10.1080/10286020.2021.2023506. Epub 2022 Jan 3.
A new approach for the synthesis of the active barbatic acid has been achieved in eight steps with 22.3% total yield by using commercially available methyl atratate as starting material. This synthesis provides access to multi-gram quantities of barbatic acid with good purity for reference supplies and further analytical and toxicology investigations.
3. Parmosidone K, a new meta-depsidone from the lichen Parmotrema tsavoense
Thi-Hoai-Thu Nguyen, Thi-My-Nhung Nguyen, Thanh-Trung Nguyen, Huu-Hung Nguyen, Ngoc-Hong Nguyen, Dinh-Tri Mai, Bui-Linh-Chi Huynh, Cong-Luan Tran, Thuc-Huy Duong Nat Prod Res. 2022 Apr;36(8):2037-2042. doi: 10.1080/14786419.2020.1844697. Epub 2020 Nov 20.
Further phytochemical investigation on P. tsavoense led to one new meta-depsidone, parmosidone K together with one known compound, barbatic acid. Their structures were determined by 1D and 2D NMR analysis, high resolution mass spectroscopy, and comparison their NMR data with those reported in literatures. Parmosidone K was evaluated for α-glucosidase inhibition and revealed the powerful activity with IC50 value of 3.12 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 ╳
