Pinselin
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| Category | Antibiotics |
| Catalog number | BBF-02419 |
| CAS | 476-53-9 |
| Molecular Weight | 300.26 |
| Molecular Formula | C16H12O6 |
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Description
It is produced by the strain of Penicillium sp., Pen. amarum. It is a nitrogen-containing heterocyclic antibiotic. It has anti-yeast activity.
Specification
| Synonyms | Pincelin; 9H-Xanthene-1-carboxylic acid, 2,8-dihydroxy-6-methyl-9-oxo-, methyl ester; Cassiollin; 1,7-Dihydroxy-8-methoxycarbonyl-3-methylxanthon |
| IUPAC Name | methyl 2,8-dihydroxy-6-methyl-9-oxoxanthene-1-carboxylate |
| Canonical SMILES | CC1=CC(=C2C(=C1)OC3=C(C2=O)C(=C(C=C3)O)C(=O)OC)O |
| InChI | InChI=1S/C16H12O6/c1-7-5-9(18)12-11(6-7)22-10-4-3-8(17)13(16(20)21-2)14(10)15(12)19/h3-6,17-18H,1-2H3 |
| InChI Key | TWQNCGDOHUNFFU-UHFFFAOYSA-N |
Properties
| Appearance | Golden Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Yeast |
| Boiling Point | 545.6°C at 760 mmHg |
| Melting Point | 225°C |
| Density | 1.467 g/cm3 |
| Solubility | Soluble in Ethyl Acetate |
Reference Reading
1. One new xanthenone from the marine-derived fungus Aspergillus versicolor MF160003
Zhijun Song, Jieyu Gao, Jiansen Hu, Hongtao He, Pei Huang, Lixin Zhang, Fuhang Song Nat Prod Res. 2020 Oct;34(20):2907-2912. doi: 10.1080/14786419.2019.1597355. Epub 2019 Apr 22.
A new xanthenone derivative, 3-hydroxy pinselin (1), together with five known analogues (2-6) were isolated from the marine-derived fungus Aspergillus versicolor MF160003. Their structures were identified by extensive 1D- and 2D-NMR, and high-resolution mass spectrometry data. Compounds 5 and 6 showed moderate bioactivities against BCG with MIC values of 40 and 20 μg/mL, respectively.
2. Isolation and Bioactivity of Secondary Metabolites from Solid Culture of the Fungus, Alternaria sonchi
Anna Dalinova, Leonid Chisty, Dmitry Kochura, Varvara Garnyuk, Maria Petrova, Darya Prokofieva, Anton Yurchenko, Vsevolod Dubovik, Alexander Ivanov, Sergey Smirnov, Andrey Zolotarev, Alexander Berestetskiy Biomolecules. 2020 Jan 4;10(1):81. doi: 10.3390/biom10010081.
The fungus, Alternaria sonchi is considered to be a potential agent for the biocontrol of perennial sowthistle (Sonchus arvensis). A new chlorinated xanthone, methyl 8-hydroxy-3-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (1) and a new benzophenone derivative, 5-chloromoniliphenone (2), were isolated together with eleven structurally related compounds (3-13) from the solid culture of the fungus, which is used for the production of bioherbicidal inoculum of A. sonchi. Their structures were determined by spectroscopic (mostly by NMR and MS) methods. Alternethanoxins A and B, which were reported in A. sonchi earlier, were re-identified as moniliphenone and pinselin, respectively. The isolated compounds were tested for phytotoxic, antimicrobial, insecticidal, cytotoxic and esterase-inhibition activities. They did not demonstrate high phytotoxicity (lesions up to 2.5 mm in diameter/length at a concentration of 2 mg/mL) when tested on leaf disks/segments of perennial sowthistle (Sonchus arvensis) and couch grass (Elytrigia repens). They did not possess acute toxicity to Paramecium caudatum, and showed moderate to low cytotoxicity (IC50 > 25 µg/mL) for U937 and K562 tumor cell lines. However, chloromonilicin and methyl 3,8-dihydroxy-6-methyl-4-chloro-9-oxo-9H-xanthene-1-carboxylate (4) were shown to have antimicrobial properties with MIC 0.5-5 µg/disc. Compound 4 and chloromonilinic acid B were found to have contact insecticidal activity to wheat aphid (Schizaphis graminum) at 1 mg/mL. Compounds 2 and methyl 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate displayed selective carboxylesterase inhibition activity at concentration of 100 µg/mL. Therefore, the waste solid substrate for production of A. sonchi spores can be re-utilized for the isolation of a number of valuable natural products.
3. Saccharobisindole, Neoasterric Methyl Ester, and 7-Chloro-4(1H)-quinolone: Three New Compounds Isolated from the Marine Bacterium Saccharomonospora sp
Sohee Kim, Tu Cam Le, Sang-Ah Han, Prima F Hillman, Ahreum Hong, Sunghoon Hwang, Young Eun Du, Hiyoung Kim, Dong-Chan Oh, Sun-Shin Cha, Jihye Lee, Sang-Jip Nam, William Fenical Mar Drugs. 2021 Dec 29;20(1):35. doi: 10.3390/md20010035.
Analysis of the chemical components from the culture broth of the marine bacterium Saccharomonospora sp. CNQ-490 has yielded three novel compounds: saccharobisindole (1), neoasterric methyl ester (2), and 7-chloro-4(1H)-quinolone (3), in addition to acremonidine E (4), pinselin (5), penicitrinon A (6), and penicitrinon E (7). The chemical structures of the three novel compounds were elucidated by the interpretation of 1D, 2D nuclear magnetic resonance (NMR), and high-resolution mass spectrometry (HRMS) data. Compound 2 generated weak inhibition activity against Bacillus subtilis KCTC2441 and Staphylococcus aureus KCTC1927 at concentrations of 32 μg/mL and 64 μg/mL, respectively, whereas compounds 1 and 3 did not have any observable effects. In addition, compound 2 displayed weak anti-quorum sensing (QS) effects against S. aureus KCTC1927 and Micrococcus luteus SCO560.
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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 ╳
