Griseochelin
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| Category | Antibiotics |
| Catalog number | BBF-01805 |
| CAS | 91920-88-6 |
| Molecular Weight | 568.83 |
| Molecular Formula | C33H60O7 |
| Purity | ≥98% |
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Description
It is produced by the strain of Streptomyces griseus ZIMET 43681. It has anti-gram-negative bacterial activity, and its ammonium salt and sodium salt have inhibitory effect on coccidioides.
Specification
| Synonyms | Antibiotic M144255; Zincophorin; 2H-Pyran-2-acetic acid, tetrahydro-alpha,5-dimethyl-6-(2,4,6,12-tetrahydroxy-1,3,5,11,13,15-hexamethyl-9,13-octadecadienyl)-; Tetrahydro-α,5-dimethyl-6-(2,4,6,12-tetrahydroxy-1,3,5,11,13,15-hexamethyl-9,13-octadecadienyl)-2H-pyran-2-acetic acid |
| IUPAC Name | 2-[5-methyl-6-[(10E,14E)-3,5,7,13-tetrahydroxy-4,6,12,14,16-pentamethylnonadeca-10,14-dien-2-yl]oxan-2-yl]propanoic acid |
| Canonical SMILES | CCCC(C)C=C(C)C(C(C)C=CCCC(C(C)C(C(C)C(C(C)C1C(CCC(O1)C(C)C(=O)O)C)O)O)O)O |
| InChI | InChI=1S/C33H60O7/c1-10-13-19(2)18-22(5)29(35)20(3)14-11-12-15-27(34)23(6)30(36)25(8)31(37)26(9)32-21(4)16-17-28(40-32)24(7)33(38)39/h11,14,18-21,23-32,34-37H,10,12-13,15-17H2,1-9H3,(H,38,39)/b14-11+,22-18+ |
| InChI Key | XMCIULDTDFJACK-YADMGGFDSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 712.6±55.0 °C (Predicted) |
| Melting Point | 72-74 °C |
| Density | 1.047±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform |
Reference Reading
1. Metabolic profiling and biological potential of the marine sponge associated Nocardiopsis sp. UR67 along with docking studies
Alyaa Hatem Ibrahim, Eman Zekry Attia, Heba A Hofny, Faisal Alsenani, Ahmed Zayed, Mostafa E Rateb, Usama Ramadan Abdelmohsen, Samar Yehia Desoukey, Mostafa Ahmed Fouad, Mohamed Salah Kamel Nat Prod Res. 2022 Jun 6;1-7. doi: 10.1080/14786419.2022.2084396. Online ahead of print.
This work was performed to dig into the phytochemical composition and bioactivities of Nocardiopsis sp. UR67 associated with the marine sponge Callyspongia sp. It was fermented in suspension and immobilised in calcium alginate bead cultures. The ethyl acetate extracts, afforded from the broth in each case named EG-49 and J-48g, respectively, revealed 16 chemical principles mostly belonging to polyketides, macrolides, and peptides. EG-49 and J-48g displayed anti-Candida albicans activity with IC50 values of 8.1 and 8.3 µg/mL, and a substantial cytotoxic effect against lung adenocarcinoma H1650 at IC50 12.6 and 13.7 µg/mL, respectively. However, only EG-49 exhibited a noteworthy anti-trypanosomal activity at 7.5 µg/mL. Molecular docking of the characterised compounds against Trypanosoma brucei trypanothione reductase demonstrated the highest binding models of griseochelin-methyl ester (9) and filipin-II (11), which drew considerable significance of the metabolites derived from Nocardiopsis sp. UR67 developing potential T. brucei trypanothione reductase inhibitors.
2. Evolution of an Efficient and Scalable Nine-Step (Longest Linear Sequence) Synthesis of Zincophorin Methyl Ester
Liang-An Chen, Melissa A Ashley, James L Leighton J Am Chem Soc. 2017 Mar 29;139(12):4568-4573. doi: 10.1021/jacs.7b01590. Epub 2017 Mar 15.
Because of both their synthetically challenging and stereochemically complex structures and their wide range of often clinically relevant biological activities, nonaromatic polyketide natural products have for decades attracted an enormous amount of attention from synthetic chemists and played an important role in the development of modern asymmetric synthesis. Often, such compounds are not available in quantity from natural sources, rendering analogue synthesis and drug development efforts extremely resource-intensive and time-consuming. In this arena, the quest for ever more step-economical and efficient methods and strategies, useful and important goals in their own right, takes on added importance, and the most useful syntheses will combine high levels of step-economy with efficiency and scalability. The nonaromatic polyketide natural product zincophorin methyl ester has attracted significant attention from synthetic chemists due primarily to the historically synthetically challenging C(8)-C(12) all-anti stereopentad. While great progress has been made in the development of new methodologies to more directly address this problem and as a result in the development of more highly step-economical syntheses, a synthesis that combines high levels of step economy with high levels of efficiency and scalability has remained elusive. To address this problem, we have devised a new synthesis of zincophorin methyl ester that proceeds in just nine steps in the longest linear sequence and proceeds in 10% overall yield. Additionally, the scalability and practicability of the route have been demonstrated by performing all of the steps on a meaningful scale. This synthesis thus represents by a significant margin the most step-economical, efficient, and practicable synthesis of this stereochemically complex natural product reported to date, and is well suited to facilitate the synthesis of analogues and medicinal chemistry development efforts in a time- and resource-efficient manner.
3. Taxonomic Characterization and Secondary Metabolite Analysis of NEAU-wh3-1: An Embleya Strain with Antitumor and Antibacterial Activity
Han Wang, Tianyu Sun, Wenshuai Song, Xiaowei Guo, Peng Cao, Xi Xu, Yue Shen, Junwei Zhao Microorganisms. 2020 Mar 20;8(3):441. doi: 10.3390/microorganisms8030441.
Cancer is a serious threat to human health. With the increasing resistance to known drugs, it is still urgent to find new drugs or pro-drugs with anti-tumor effects. Natural products produced by microorganisms have played an important role in the history of drug discovery, particularly in the anticancer and anti-infective areas. The plant rhizosphere ecosystem is a rich resource for the discovery of actinomycetes with potential applications in pharmaceutical science, especially Streptomyces. We screened Streptomyces-like strains from the rhizosphere soil of wheat (Triticum aestivum L.) in Hebei province, China, and thirty-nine strains were obtained. Among them, the extracts of 14 isolates inhibited the growth of colon tumor cell line HCT-116. Strain NEAU-wh-3-1 exhibited better inhibitory activity, and its active ingredients were further studied. Then, 16S rRNA gene sequence similarity studies showed that strain NEAU-wh3-1 with high sequence similarities to Embleya scabrispora DSM 41855T (99.65%), Embleya hyalina MB891-A1T (99.45%), and Streptomyces lasii 5H-CA11T (98.62%). Moreover, multilocus sequence analysis based on the five other house-keeping genes (atpD, gyrB, rpoB, recA, and trpB) and polyphasic taxonomic approach comprising chemotaxonomic, phylogenetic, morphological, and physiological characterization indicated that the isolate should be assigned to the genus Embleya and was different from its closely related strains, therefore, it is proposed that strain NEAU-wh3-1 may be classified as representatives of a novel species of the genus Embleya. Furthermore, active substances in the fermentation broth of strain NEAU-wh-3-1 were isolated by bioassay-guided analysis and identified by nuclear magnetic resonance (NMR) and mass spectrometry (MS) analyses. Consequently, one new Zincophorin analogue together with seven known compounds was detected. The new compound showed highest antitumor activity against three human cell lines with the 50% inhibition (IC50) values of 8.8-11.6 μg/mL and good antibacterial activity against four pathogenic bacteria, the other known compounds also exhibit certain biological activity.
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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 ╳
