Divaricatic acid
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| Category | Bioactive by-products |
| Catalog number | BBF-05412 |
| CAS | 491-62-3 |
| Molecular Weight | 388.41 |
| Molecular Formula | C21H24O7 |
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Description
Divaricatic acid, a secondary metabolite produced by lichens of the genus Ramalina, has molluscicidal and antiparasitic activities.
Specification
| Related CAS | 129350-24-9 (Divaricatic acid) |
| Synonyms | Divaricatic acid (Evernia); NSC 646003; Benzoic acid, 2-hydroxy-4-((2-hydroxy-4-methoxy-6-propylbenzoyl)oxy)-6-propyl-; divericatic acid; Divaricatsaeure; p-Anisic acid, 2-hydroxy-6-propyl-, 4-ester with 6-propyl-β-resorcylic acid; β-resorcylic acid, 6-propyl-, 4-(2-hydroxy-6-propyl-p-Anisate) |
| IUPAC Name | 2-hydroxy-4-(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy-6-propylbenzoic acid |
| Canonical SMILES | CCCC1=C(C(=CC(=C1)OC)O)C(=O)OC2=CC(=C(C(=C2)O)C(=O)O)CCC |
| InChI | InChI=1S/C21H24O7/c1-4-6-12-9-15(11-16(22)18(12)20(24)25)28-21(26)19-13(7-5-2)8-14(27-3)10-17(19)23/h8-11,22-23H,4-7H2,1-3H3,(H,24,25) |
| InChI Key | FSRDIJIAQPSMMR-UHFFFAOYSA-N |
Properties
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 578.4°C at 760 mmHg |
| Density | 1.273 g/cm3 |
Reference Reading
1. Toxicological effects of Ramalina aspera (lichen) on Biomphalaria glabrata snails and Schistosoma mansoni cercariae
Hianna Arely Milca Fagundes Silva, José Luís Ferreira Sá, et al. Acta Trop. 2019 Aug;196:172-179. doi: 10.1016/j.actatropica.2019.05.010. Epub 2019 May 10.
In this study, the molluscicidal activities against Biomphalaria glabrata and cercaricidal activities against Schistosoma mansoni of the ether extract of Ramalina aspera were evaluated. Additionally, toxicity parameters were evaluated at sublethal doses in terms of the influence of the extract on the fertility and fecundity of snails, as well as morphological alterations and quantification of their immunological cells. A test with Artemia salina was also carried out, in order to verify the environmental toxicity of the compound. The ether extract of R. aspera, in which divaricatic acid was identified as the major compound, demonstrated molluscicidal activity at low concentrations against both embryos (LC90 of 22.78, 24.23, 16.63 and 16.03 μg mL-1 for the gastrula, blastula, trochophore and veliger, respectively) and against adult snails (LC90 of 8.66 μg mL-1), after 24 h of exposure. At the sublethal doses, it was possible to observe a decrease in fecundity and quantitative and morphological changes in the defense cells of the exposed snails. In addition, the extract of R. aspera showed a cercaricidal effect on S. mansoni from the concentration of 5.0 μg mL-1, while showing low toxicity to Artemia salina. The ether extract of R. aspera demonstrated effective molluscicidal activity on embryos and adult snails of the species B. glabrata, cercariae of S. mansoni, and presenting low toxicity on Artemia salina. In this way, it could be considered a promising compound in the development of future molluscicidal and cercaricidal agents, thus helping to combat schistosomiasis.
2. Specialized metabolites of the United States lichen Niebla homalea and their antiproliferative activities
Yan Zhang, Choon Yong Tan, Richard W Spjut, James R Fuchs, A Douglas Kinghorn, Liva Harinantenaina Rakatondraibe Phytochemistry. 2020 Dec;180:112521. doi: 10.1016/j.phytochem.2020.112521. Epub 2020 Oct 21.
Three undescribed stictanes, nieblastictanes A-C, two flavicanes, nieblaflavicanes A and B, together with three already reported stictanes, along with the known compounds (+)-usnic acid, sekikaic acid, divaricatic acid, and divaricatinic acid methyl ester were isolated from an ethyl acetate extract of the western North American lichen Niebla homalea. The structures of the new and known compounds were established by spectroscopic methods including nuclear magnetic resonance spectroscopy, mass spectrometry and electronic circular dichroism. Among the compounds isolated, usnic acid exhibited moderately potent antiproliferative activities against the A2780 ovarian (IC50 3.8 μM) and MCF-7 breast cancer (IC50 6.8 μM) cell lines. A plausible mode of formation of the chlorine-containing compound nieblastictane C is provided and the contribution of the isolated compounds to the chemotaxonomy of United States lichen species of the genus Niebla is also discussed.
3. 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.
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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 ╳
