Viridicatol
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04357 |
| CAS | 14484-44-7 |
| Molecular Weight | 253.25 |
| Molecular Formula | C15H11NO3 |
| Purity | ≥95% |
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Description
Viridicatol is a fungal metabolite found in various Penicillium species as well as Phoma. It suppresses the expression of COX-2 and inducible nitric oxide synthase (iNOS) and inhibits production of nitric oxide and prostaglandin E2 (PGE2) in LPS-stimulated RAW 264.7 and BV2 cells.
Specification
| Synonyms | 2(1H)-Quinolinone, 3-hydroxy-4-(3-hydroxyphenyl)-; Carbostyril, 3-hydroxy-4-(m-hydroxyphenyl)-; 3-hydroxy-4-(3-hydroxyphenyl)carbostyril; 4-(3-Hydroxyphenyl)-2,3-quinolinediol |
| Storage | Store at -20°C |
| IUPAC Name | 3-hydroxy-4-(3-hydroxyphenyl)-1H-quinolin-2-one |
| Canonical SMILES | C1=CC=C2C(=C1)C(=C(C(=O)N2)O)C3=CC(=CC=C3)O |
| InChI | InChI=1S/C15H11NO3/c17-10-5-3-4-9(8-10)13-11-6-1-2-7-12(11)16-15(19)14(13)18/h1-8,17-18H,(H,16,19) |
| InChI Key | QIJIOTTYIGBOQA-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Boiling Point | 553.4±50.0°C at 760 mmHg |
| Melting Point | 280°C |
| Density | 1.4±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. Secondary metabolites isolated from Penicillium christenseniae SD.84 and their antimicrobial resistance effects
Yang Pan, Haiyan Chen, Qingzhou Meng, Peipei Zhao, Xin Yin, Xinzhu Wang, Huanqin Dai, Lixin Zhang, Xuekui Xia Nat Prod Res . 2022 Nov 6;1-9. doi: 10.1080/14786419.2022.2140150.
A pair of new quinolone alkaloid enantiomers, (Ra)-(-)-viridicatol (1) and (Sa)-(+)-viridicatol (4), and seven known compounds, namely,2,3and5-9, were isolated fromPenicillium christenseniaeSD.84. The structures of1and4were determined using NMR and HRESIMS data. Theoretical calculations through CD and ECD confirmed1and4as a pair of enantiomers. The MIC values of4againstStaphylococcus aureusand methicillin-resistantS. aureuswere 12.4 and 24.7 μM, respectively, compound1had no inhibitory activity. Antimicrobial assays of2,3, and5-7showed a moderate activity againstS. aureusand methicillin-resistantS. aureus. This study demonstrated the remarkable potential ofPenicilliumsp. to produce new drug-resistant leading compounds, thereby advancing the mining for new sources of antimicrobial agents.
2. 3-Hy-droxy-4-(3-hy-droxy-phen-yl)-2-quinolone monohydrate
Yi-Wen Tao, Yun Wang Acta Crystallogr Sect E Struct Rep Online . 2011 Aug 1;67(Pt 8):o2195-6. doi: 10.1107/S160053681102945X.
In the title compound, also known as viridicatol monohydrate, C(15)H(11)NO(3)·H(2)O, the dihedral angle between the benzene ring and quinoline ring system is 64.76 (5)°. An intra-molecular O-H⋯O hydrogen bond occurs. The crystal structure is stabilized by classical inter-molecular N-H⋯O and O-H⋯O hydrogen bonds and weak π-π inter-actions with a centroid-centroid distance of 3.8158 (10) Å.
3. Chemical Constituents of the Deep-Sea-Derived Penicillium solitum
Man-Yi Hu, Zhi-Hui He, Jia Wu, Xian-Wen Yang, Ming-Ming Xie, Zong-Ze Shao, You-Jia Hao, Shu-Jin Li, Lin Xu Mar Drugs . 2021 Oct 17;19(10):580. doi: 10.3390/md19100580.
A systematic chemical investigation of the deep-sea-derived fungusPenicillium solitumMCCC 3A00215 resulted in the isolation of one novel polyketide (1), two new alkaloids (2and3), and 22 known (4-25) compounds. The structures of the new compounds were established mainly on the basis of exhaustive analysis of 1D and 2D NMR data. Viridicatol (13) displayed moderate anti-tumor activities against PANC-1, Hela, and A549 cells with IC50values of around 20 μM. Moreover,13displayed potent in vitro anti-food allergic activity with an IC50value of 13 μM, compared to that of 92 μM for the positive control, loratadine, while indole-3-acetic acid methyl ester (9) and penicopeptide A (10) showed moderate effects (IC50= 50 and 58 μM, respectively).
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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 ╳
