Pinastric acid
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| Category | Others |
| Catalog number | BBF-05406 |
| CAS | 481-64-1 |
| Molecular Weight | 352.34 |
| Molecular Formula | C20H16O6 |
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Description
It is a derivative of pulvinic acid and isolated from a terrestrial lichen. It displays antitumour, antiviral and antimicrobial (both antibacterial and antifungal) activities.
Specification
| Synonyms | 4'-Methoxyvulpinic acid; Pianstric acid; (αE)-α-Phenyl-3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylideneacetic acid methyl ester; 2-Phenyl-2-[(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid methyl ester; Phenyl[(2E)-3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylidene]acetic acid methyl ester; α-[(2E)-3-Hydroxy-4-(4-methoxyphenyl)-5-oxo-2,5-dihydrofuran-2-ylidene]benzeneacetic acid methyl ester; Benzeneacetic acid, α-[3-hydroxy-4-(4-methoxyphenyl)-5-oxo-2(5H)-furanylidene]-, methyl ester, (αE)-; methyl (E)-2-(3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2(5H)-ylidene)-2-phenylacetate; δ2(5H),α-Furanacetic acid, 3-hydroxy-4-(p-methoxyphenyl)-5-oxo-α-phenyl-, methyl ester |
| IUPAC Name | methyl (2E)-2-[3-hydroxy-4-(4-methoxyphenyl)-5-oxofuran-2-ylidene]-2-phenylacetate |
| Canonical SMILES | COC1=CC=C(C=C1)C2=C(C(=C(C3=CC=CC=C3)C(=O)OC)OC2=O)O |
| InChI | InChI=1S/C20H16O6/c1-24-14-10-8-13(9-11-14)15-17(21)18(26-20(15)23)16(19(22)25-2)12-6-4-3-5-7-12/h3-11,21H,1-2H3/b18-16+ |
| InChI Key | KXQKSBAGVQMQSN-FBMGVBCBSA-N |
Properties
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Bacteria; Viruses; Fungi |
| Boiling Point | 549.2±50.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Lichen Extracts from Cetrarioid Clade Provide Neuroprotection against Hydrogen Peroxide-Induced Oxidative Stress
Isabel Ureña-Vacas, Elena González-Burgos, Pradeep Kumar Divakar, María Pilar Gómez-Serranillos Molecules. 2022 Oct 2;27(19):6520. doi: 10.3390/molecules27196520.
Oxidative stress is involved in the pathophysiology of many neurodegenerative diseases. Lichens have antioxidant properties attributed to their own secondary metabolites with phenol groups. Very few studies delve into the protective capacity of lichens based on their antioxidant properties and their action mechanism. The present study evaluates the neuroprotective role of Dactylina arctica, Nephromopsis stracheyi, Tuckermannopsis americana and Vulpicida pinastri methanol extracts in a hydrogen peroxide (H2O2) oxidative stress model in neuroblastoma cell line "SH-SY5Y cells". Cells were pretreated with different concentrations of lichen extracts (24 h) before H2O2 (250 µM, 1 h). Our results showed that D. arctica (10 µg/mL), N. stracheyi (25 µg/mL), T. americana (50 µg/mL) and V. pinastri (5 µg/mL) prevented cell death and morphological changes. Moreover, these lichens significantly inhibited reactive oxygen species (ROS) production and lipid peroxidation and increased superoxide dismutase (SOD) and catalase (CAT) activities and glutathione (GSH) levels. Furthermore, they attenuated mitochondrial membrane potential decline and calcium homeostasis disruption. Finally, high-performance liquid chromatography (HPLC) analysis revealed that the secondary metabolites were gyrophoric acid and lecanoric acid in D. artica, usnic acid, pinastric acid and vulpinic acid in V. pinastri, and alectoronic acid in T. americana. In conclusion, D. arctica and V. pinastri are the most promising lichens to prevent and to treat oxidative stress-related neurodegenerative diseases.
2. Catalytic Undirected Intermolecular C-H Functionalization of Arenes with 3-Diazofuran-2,4-dione: Synthesis of 3-Aryl Tetronic Acids, Vulpinic Acid, Pinastric Acid, and Methyl Isoxerocomate
Amarender Manchoju, Sunil V Pansare Org Lett. 2016 Nov 18;18(22):5952-5955. doi: 10.1021/acs.orglett.6b03087. Epub 2016 Nov 8.
A variety of 3-aryl tetronic acids have been synthesized by an undirected, intermolecular C-H functionalization of arenes with 3-diazofuran-2,4-dione. This methodology featured as a key step in the synthesis of a series of naturally occurring 3-aryl-5-arylidene tetronic acids (pulvinates) from commercially available tetronic acid. Salient features of the pulvinic acid synthesis include a one-step, stereoselective synthesis of the C5 arylidene group and a single step introduction of the C3 aryl substituent.
3. Specialized Metabolites of the Lichen Vulpicida pinastri Act as Photoprotective Agents
Béatrice Legouin, Françoise Lohézic-Le Dévéhat, Solenn Ferron, Isabelle Rouaud, Pierre Le Pogam, Laurence Cornevin, Michel Bertrand, Joël Boustie Molecules. 2017 Jul 12;22(7):1162. doi: 10.3390/molecules22071162.
The extreme resiliency of lichens to UV radiations makes them an interesting model to find new photoprotective agents acting as UV-blockers and antioxidant. In this research, using a new in vitro method designed to overcome the shortage of material associated to many studies dealing with natural products, we show that the three major compounds isolated from the lichen Vulpicida pinastri, vulpinic acid, pinastric acid and usnic acid, were UV blocker agents. Antioxidant assays evidenced superoxide anion scavenging activity. Combination of the most promising compounds against UVB and UVB radiations, usnic acid, vulpinic acid and pinastric acid, increased the photoprotective activity. At the same time, they were found not cytotoxic on keratinocyte cell lines and photostable in the UVA and UVB ranges. Thus, lichens represent an attractive source to find good candidate ingredients as photoprotective agents. Additionally, the uncommon scalemic usnic acid mixture in this Vulpicida species was proven through electronic circular dichroism calculation.
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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 ╳
