Physodalic acid
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Others |
| Catalog number | BBF-05641 |
| CAS | 90689-60-4 |
| Molecular Weight | 416.33 |
| Molecular Formula | C20H16O10 |
Online Inquiry
Description
It is a lichen depsidone isolated from Hypogymnia physodes.
Specification
| Synonyms | 4-(acetyloxymethyl)-10-formyl-3,9-dihydroxy-1,7-dimethyl-6-oxobenzo[b][1,4]benzodioxepine-2-carboxylic acid; CCRIS 5525; 11H-Dibenzo[b,e][1,4]dioxepin-7-carboxylic acid, 9-[(acetyloxy)methyl]-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo- |
| IUPAC Name | 9-(acetoxymethyl)-4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepine-7-carboxylic acid |
| Canonical SMILES | CC1=CC(=C(C2=C1C(=O)OC3=C(O2)C(=C(C(=C3COC(=O)C)O)C(=O)O)C)C=O)O |
| InChI | InChI=1S/C20H16O10/c1-7-4-12(23)10(5-21)17-13(7)20(27)30-18-11(6-28-9(3)22)15(24)14(19(25)26)8(2)16(18)29-17/h4-5,23-24H,6H2,1-3H3,(H,25,26) |
| InChI Key | SKXNIRUDASOCCN-UHFFFAOYSA-N |
Properties
| Boiling Point | 684.0±55.0°C at 760 mmHg |
| Density | 1.548 g/cm3 |
Reference Reading
1. Lichen Depsidones with Biological Interest
Isabel Ureña-Vacas, Elena González-Burgos, Pradeep Kumar Divakar, M Pilar Gómez-Serranillos Planta Med. 2022 Sep;88(11):855-880. doi: 10.1055/a-1482-6381. Epub 2021 May 25.
Depsidones are some of the most abundant secondary metabolites produced by lichens. These compounds have aroused great pharmacological interest due to their activities as antioxidants, antimicrobial, and cytotoxic agents. Hence, this paper aims to provide up-to-date knowledge including an overview of the potential biological interest of lichen depsidones. So far, the most studied depsidones are fumarprotocetraric acid, lobaric acid, norstictic acid, physodic acid, salazinic acid, and stictic acid. Their pharmacological activities have been mainly investigated in in vitro studies and, to a lesser extent, in in vivo studies. No clinical trials have been performed yet. Depsidones are promising cytotoxic agents that act against different cell lines of animal and human origin. Moreover, these compounds have shown antimicrobial activity against both Gram-positive and Gram-negative bacteria and fungi, mainly Candida spp. Furthermore, depsidones have antioxidant properties as revealed in oxidative stress in vitro and in vivo models. Future research should be focused on further investigating the mechanism of action of depsidones and in evaluating new potential actions as well as other depsidones that have not been studied yet from a pharmacological perspective. Likewise, more in vivo studies are prerequisite, and clinical trials for the most promising depsidones are encouraged.
2. Physodic acid sensitizes LNCaP prostate cancer cells to TRAIL-induced apoptosis
Venera Cardile, Adriana C E Graziano, Rosanna Avola, Alejandro Madrid, Alessandra Russo Toxicol In Vitro. 2022 Oct;84:105432. doi: 10.1016/j.tiv.2022.105432. Epub 2022 Jul 7.
In spite of the extensive research for developing new therapies, prostate cancer is still one of the major human diseases with poor prognosis and high mortality. Therefore, with the aim of identifying novel agents with antigrowth and pro-apoptotic activity on prostate cancer cells, in the present study, we evaluated the effect of lichen secondary metabolite physodic acid on cell growth in human prostate cancer cells. In addition, we tested the apoptotic activity of physodic acid on TRAIL-resistant LNCaP cells in combination with TRAIL. The cell viability was measured using MTT assay. LDH release, a marker of membrane breakdown, was also measured. For the detection of apoptosis, the evaluation of DNA fragmentation and caspase-3 activity assay were employed. The expression of proteins was detected by Western blot analysis. It was observed that physodic acid showed a dose-response relationship in the range of 12.5-50 μM concentrations in LNCaP and DU-145 cells, activating an apoptotic process. In addition, physodic acid sensitizes LNCaP cells to TRAIL-induced apoptosis. The combination of physodic acid with other anti-prostate cancer therapies could be considered a promising strategy that warrants further investigations.
3. Biological Effects of Gyrophoric Acid and Other Lichen Derived Metabolites, on Cell Proliferation, Apoptosis and Cell Signaling pathways
Mahshid Mohammadi, Leila Bagheri, Amr Badreldin, Pedram Fatehi, Leila Pakzad, Zacharias Suntres, Andre J van Wijnen Chem Biol Interact. 2022 Jan 5;351:109768. doi: 10.1016/j.cbi.2021.109768. Epub 2021 Dec 3.
Secondary metabolites from fungi, algae and lichens have remarkable biological activities as antibiotics, fungicides, antiviral drugs, and cancer therapeutics. This review focuses on the lichen-derived metabolite gyrophoric acid and other select secondary metabolites (e.g., usnic acid, salazinic acid, physodic acid, vulpinic acid ceratinalone, flavicansone, ramalin, physciosporin, tumidulin, atranorin, parmosidone) that modulate a number of cellular pathways relevant to several biomedical diseases and disorders, including cancer, diabetes and cardiovascular disease. We discuss the chemical structure and biochemical activities of gyrophoric acid and other compounds relative to the molecular mechanisms and cellular processes that these metabolites target in a distinct human and rodent cell types. The therapeutic promise of gyrophoric acid and similar lichen derived metabolites is associated with the chemical versatility of these compounds as polyaromatic depsides with functional carboxyl and hydroxyl side-groups that may permit selective interactions with distinct enzymatic active sites. Gyrophoric acid has been examined in a series of studies as an effective anticancer drug because it impinges on topoisomerase 1 activity, as well as causes cell cycle arrest, comprises cell survival, and promotes apoptosis. Because gyrophoric acid has cytostatic properties, its biological roles and possible medicinal utility may extend beyond effects on cancer cells and be relevant to any process that is controlled by cell growth and differentiation.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
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 ╳
