Palitantin
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| Category | Antibiotics |
| Catalog number | BBF-02666 |
| CAS | 15265-28-8 |
| Molecular Weight | 254.32 |
| Molecular Formula | C14H22O4 |
| Purity | ≥95% |
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Description
It is produced by the strain of Pen. palitans. It is an antibiotic with antifungal and antiprotozoal properties.
Specification
| Synonyms | NSC-246119; Cyclohexanone, 3-(1E,3E)-1,3-heptadien-1-yl-5,6-dihydroxy-2-(hydroxymethyl)-, (2R,3S,5R,6R)-; rel-(2R,3S,5R,6R)-3-(1E,3E)-1,3-Heptadien-1-yl-5,6-dihydroxy-2-(hydroxymethyl)cyclohexanone; (±)-Palitantin; [2α,3β(1E,3E),5α,6α]-3-(1,3-Heptadienyl)-5,6-dihydroxy-2-(hydroxymethyl)-cyclohexanone |
| IUPAC Name | (2R,3S,5R,6R)-5-[(1E,3E)-hepta-1,3-dienyl]-2,3-dihydroxy-6-(hydroxymethyl)cyclohexan-1-one |
| Canonical SMILES | CCCC=CC=CC1CC(C(C(=O)C1CO)O)O |
| InChI | InChI=1S/C14H22O4/c1-2-3-4-5-6-7-10-8-12(16)14(18)13(17)11(10)9-15/h4-7,10-12,14-16,18H,2-3,8-9H2,1H3/b5-4+,7-6+/t10-,11+,12-,14-/m1/s1 |
| InChI Key | MPOXQBRZHHNMER-XZQMCIKJSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | Fungi; Parasites |
| Boiling Point | 429.1°C at 760 mmHg |
| Melting Point | 163-169°C |
| Density | 1.205 g/cm3 |
| Solubility | Soluble in Chloroform, Ethanol |
Reference Reading
1. Cyclohexanone derivatives with cytotoxicity from the fungus Penicillium commune
Xing-zhong Liu, Jin-shan Tang, Yong-sheng Che, Xin-sheng Yao, Fang-zhi Liu, Jin-wei Ren Fitoterapia . 2013 Jun;87:78-83. doi: 10.1016/j.fitote.2013.03.022.
Four new cyclohexanone derivatives (2-5) and one known analog, (-)-Palitantin (1) were isolated from the EtOAc extract of Penicillium commune, a fungal strain of low-temperature habitats. The structures of 2-5 were determined on the basis of extensive spectroscopic analysis. Furthermore, the absolute configuration of 2 was assigned by electronic circular dichroism (ECD) calculations, whereas that 3-5 were deduced via the CD data. Cytotoxicities of 2-5 against five human carcinoma cell lines (Hela, A549, MCF7, HCT116, T24) were evaluated.
2. Palitantin derivatives from the Antarctic fungus Geomyces sp. 3-1
Ying He, Yun-Hai Li, Xiao-Yu Liu, Hao-Bing Yu, Jie Kong, Bing-Hua Jiao, Bo Hu, Xiao-Ling Lu J Asian Nat Prod Res . 2022 Mar;24(3):252-258. doi: 10.1080/10286020.2021.1915995.
Two new polyketides, palitantins B and C (1and2), along with one known related compound (+)-palitantin (3) were obtained from the culture of the Antarctic fungusGeomycessp. 3-1. The structures of the new compounds were elucidated by detailed analysis of HRESIMS, NMR, CD, and ECD data. Compound3showed potent PTP1B inhibitory activity with an IC50value of 7.9μM (ursolic acid as positive control, IC50= 8.3μM).
3. Antimicrobial and Antioxidant Polyketides from a Deep-Sea-Derived Fungus Aspergillus versicolor SH0105
Chang-Yun Wang, Lu-Jia Yang, Xin Li, Xiao-Yue Peng, Ya-Hui Zhang, Chang-Lun Shao, Zhuang Han, Yu-Cheng Gu, Zhi-Qing Liu Mar Drugs . 2020 Dec 11;18(12):636. doi: 10.3390/md18120636.
Fifteen polyketides, including four new compounds, isoversiol F (1), decumbenone D (2), palitantin B (7), and 1,3-di-O-methyl-norsolorinic acid (8), along with 11 known compounds (3-6and9-15), were isolated from the deep-sea-derived fungusAspergillus versicolorSH0105. Their structures and absolute configurations were determined by comprehensive spectroscopic data, including 1D and 2D NMR, HRESIMS, and ECD calculations, and it is the first time to determine the absolute configuration of known decumbenone A (6). All of these compounds were evaluated for their antimicrobial activities against four human pathogenic microbes and five fouling bacterial strains. The results indicated that 3,7-dihydroxy-1,9-dimethyldibenzofuran (14) displayed obvious inhibitory activity againstStaphylococcus aureus(ATCC 27154) with the MIC value of 13.7 μM. In addition, the antioxidant assays of the isolated compounds revealed that aspermutarubrol/violaceol-I (15) exhibited significant 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity with the IC50value of 34.1 μM, and displayed strong reduction of Fe3+with the ferric reducing antioxidant power (FRAP) value of 9.0 mM under the concentration of 3.1 μg/mL, which were more potent than ascorbic acid.
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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 ╳
