Zygosporin E
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Category | Antibiotics |
Catalog number | BBF-02983 |
CAS | 26399-27-9 |
Molecular Weight | 491.62 |
Molecular Formula | C30H37NO5 |
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Description
Zygosporin E is produced by the strain of Zygosporium masonii MFC-612 and Zygosporium mycophylum MFC-702. It is cytotoxic to HeLa cells with ED50 of 0.4 μg/mL. It has anti-tumor and anti-inflammatory properties.
Specification
Related CAS | 114651-74-0 ((±)-Zygosporin E) |
Synonyms | (7S,13E,16S,18S,19E,21R)-21-Acetoxy-7-hydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,19-triene-1,17-dione; 1H-Cycloundec[d]isoindole-1,11(2H)-dione, 15-(acetyloxy)-3,3a,4,5,6,6a,9,10,12,15-decahydro-6-hydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12S,13E,15R,15aR)-; Z-Val-Lys-Met 7-amido-4-methylcoumarin; Z-Val-Lys-Met-MCA |
IUPAC Name | (3S,3aR,4S,6S,6aR,7E,10S,12S,13E,15R,15aR)-3-benzyl-6-hydroxy-4,10,12-trimethyl-5-methylene-1,11-dioxo-2,3,3a,4,5,6,6a,9,10,11,12,15-dodecahydro-1H-cycloundeca[d]isoindol-15-yl acetate |
Canonical SMILES | CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1=O)C)OC(=O)C)C(=O)NC3CC4=CC=CC=C4)C)O |
InChI | InChI=1S/C30H37NO5/c1-17-10-9-13-23-28(34)20(4)19(3)26-24(16-22-11-7-6-8-12-22)31-29(35)30(23,26)25(36-21(5)32)15-14-18(2)27(17)33/h6-9,11-15,17-19,23-26,28,34H,4,10,16H2,1-3,5H3,(H,31,35)/b13-9+,15-14+/t17-,18+,19-,23?,24+,25-,26?,28-,30?/m1/s1 |
InChI Key | YOSIWRQXBHJIKL-KJRGTWELSA-N |
Properties
Appearance | Colorless Acicular Crystal |
Antibiotic Activity Spectrum | Neoplastics (Tumor) |
Boiling Point | 678.3±55.0°C at 760 mmHg |
Melting Point | 218-223.5°C |
Density | 1.19±0.1 g/cm3 |
Solubility | Soluble in Dioxane, Methanol, Chloroform |
Reference Reading
1. Metabolomic-guided discovery of cyclic nonribosomal peptides from Xylaria ellisii sp. nov., a leaf and stem endophyte of Vaccinium angustifolium
Ashraf Ibrahim, Joey B Tanney, Fan Fei, Keith A Seifert, G Christopher Cutler, Alfredo Capretta, J David Miller, Mark W Sumarah Sci Rep. 2020 Mar 12;10(1):4599. doi: 10.1038/s41598-020-61088-x.
Fungal endophytes are sources of novel bioactive compounds but relatively few agriculturally important fruiting plants harboring endophytes have been carefully studied. Previously, we identified a griseofulvin-producing Xylaria species isolated from Vaccinium angustifolium, V. corymbosum, and Pinus strobus. Morphological and genomic analysis determined that it was a new species, described here as Xylaria ellisii. Untargeted high-resolution LC-MS metabolomic analysis of the extracted filtrates and mycelium from 15 blueberry isolates of this endophyte revealed differences in their metabolite profiles. Toxicity screening of the extracts showed that bioactivity was not linked to production of griseofulvin, indicating this species was making additional bioactive compounds. Multivariate statistical analysis of LC-MS data was used to identify key outlier features in the spectra. This allowed potentially new compounds to be targeted for isolation and characterization. This approach resulted in the discovery of eight new proline-containing cyclic nonribosomal peptides, which we have given the trivial names ellisiiamides A-H. Three of these peptides were purified and their structures elucidated by one and two-dimensional nuclear magnetic resonance spectroscopy (1D and 2D NMR) and high-resolution tandem mass spectrometry (HRMS/MS) analysis. The remaining five new compounds were identified and annotated by high-resolution mass spectrometry. Ellisiiamide A demonstrated Gram-negative activity against Escherichia coli BW25113, which is the first reported for this scaffold. Additionally, several known natural products including griseofulvin, dechlorogriseofulvin, epoxy/cytochalasin D, zygosporin E, hirsutatin A, cyclic pentapeptides #1-2 and xylariotide A were also characterized from this species.
2. Zygosporin D and two new cytochalasins produced by the fungus Metarrhizium anisopliae
Y Fujii, H Tani, M Ichinoe, H Nakajima J Nat Prod. 2000 Jan;63(1):132-5. doi: 10.1021/np990331t.
Zygosporin D (3) and two new cytochalasins (4 and 5) were isolated from the culture filtrate of the fungus Metarrhizium anisopliae and characterized on the basis of their spectral data and chemical conversions. The new cytochalasins, 4 and 5, were determined to be deacetylcytochalasin C and (6R,16S,18R,21R)-18,21-dihydroxy-16, 18-dimethyl-10-phenyl[11]cytochalasa-13(E),19(E)-diene-1,7,17-trio ne, respectively. Of these three cytochalasins, only zygosporin D is an effective inhibitor of shoot elongation of rice seedlings.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳