Zygosporin D

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Zygosporin D
Category Antibiotics
Catalog number BBF-02982
CAS 25374-67-8
Molecular Weight 465.58
Molecular Formula C28H35NO5

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Description

Zygosporin D 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

Synonyms Desacetylcytochalasin D; Deactylzygosporin A; (7S,13E,16S,18R,19E,21R)-7,18,21-Trihydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13,19-triene-1,17-dione; 1H-Cycloundec[d]isoindole-1,11(2H)-dione, 3,3a,4,5,6,6a,9,10,12,15-decahydro-6,12,15-trihydroxy-4,10,12-trimethyl-5-methylene-3-(phenylmethyl)-, (3S,3aR,4S,6S,6aR,7E,10S,12R,13E,15R,15aR)-
IUPAC Name (1R,2R,3E,5R,7S,9E,11R,12S,14S,15R,16S)-16-benzyl-2,5,12-trihydroxy-5,7,14-trimethyl-13-methylidene-17-azatricyclo[9.7.0.01,15]octadeca-3,9-diene-6,18-dione
Canonical SMILES CC1CC=CC2C(C(=C)C(C3C2(C(C=CC(C1=O)(C)O)O)C(=O)NC3CC4=CC=CC=C4)C)O
InChI InChI=1S/C28H35NO5/c1-16-9-8-12-20-24(31)18(3)17(2)23-21(15-19-10-6-5-7-11-19)29-26(33)28(20,23)22(30)13-14-27(4,34)25(16)32/h5-8,10-14,16-17,20-24,30-31,34H,3,9,15H2,1-2,4H3,(H,29,33)/b12-8+,14-13+/t16-,17+,20-,21-,22+,23-,24+,27+,28+/m0/s1
InChI Key DMUBZPWTFAPROZ-CEAYGSLDSA-N

Properties

Appearance Colorless Flaky Crystal
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 718.5±60.0°C (Predicted)
Melting Point 180-190°C
Density 1.25±0.1 g/cm3 (Predicted)
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. Cytotoxic cytochalasans from fungus Xylaria longipes
Wen-Xuan Wang, Zheng-Hui Li, Juan He, Tao Feng, Jing Li, Ji-Kai Liu Fitoterapia. 2019 Sep;137:104278. doi: 10.1016/j.fitote.2019.104278. Epub 2019 Jul 25.
Five new cytochalasans (1-5) were isolated from the rice fermentation of fungus Xylaria longipes, along with seven known compounds cytochalasin P (6), cytochalasin D (7), zygosporin D (8), 7-O-acetylcytochalasin D (9), cytochalasin C (10), 6,7-dihydro-7-oxo-cytochalasin C (11), and 6,7-dihydro-7-oxo-deacetylcytochalasin C (12). Their structures and absolute configurations were determined by extensive experimental spectroscopic methods as well as ECD calculation and GIAO 13C NMR calculation. The cytotoxicity of obtained compounds (1-12) was evaluated against human cancer cell lines HL-60, A549, SMMC-7721, MCF-7, and SW480. Compounds 6-8, 11, and 12 showed cytotoxicity with IC50 value ranging from 4.17-37.18 μM.
3. [Antitumor Chemical Entities of Cordyceps taii Mycelia Powder from Guizhou]
Xiao-gang Li, Wei-dong Pan, Xiao-jie Zhang, Jian-hui Xiao Zhong Yao Cai. 2015 Oct;38(10):2083-6.
Objective: To seperate and identify the chemicals from the antitumor fraction of Cordyceps taii mycelia powder. Methods: The mycelia of Cordyceps taii were prepared by the submerged fermentation technique. Chemical entities in the antitumor fraction of Cordyceps taii were isolated and purified by using different column chromatographies (silica gel, Sephadex LH-20 and MCI), and semi-preparative HPLC method. Theirs chemical structures were then identified by different spectrum techniques such as EI, ESI and 1D/2D-NMR, etc. The cytotoxic activity was investigated by the Sulforhodamine B (SRB) assay. Results: Six compounds, such as 5α,8α-epidioxyergosta-6,22-dien-3β-ol (1), ergosterol (2), adenine nucleoside (3), helvolic acid (4), deacetylcytochalasin C (5) and zygosporin D (6), were identified. The IC50 value of compound 2 against human gastric cancer cell line SGC-7901 was 5.99 μmol/L, which was less than the half value of cisplatin, and had lower cytotoxicity to normal cells in comparison with cisplatin. Conclusion: Six compounds have been isolated from the antitumor fraction of Cordyceps taii mycelia powder,of which compounds 1, 5 and 6 are isolated from Cordyceps taii for the first time. Compounds 1, 2 and 4 have cytotoxic activities against cancer cells, and should be the main antitumor compounds of Cordyceps taii.

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