Epoxycytochalasin H
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| Category | Others |
| Catalog number | BBF-02004 |
| CAS | 96639-05-3 |
| Molecular Weight | 493.63 |
| Molecular Formula | C30H39NO5 |
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Description
Epoxycytochalasin H is a metabolite of Phomopsis sojae. It has a plant growth inhibitory effect.
Specification
| IUPAC Name | [(1R,2R,3E,5R,7S,9E,11R,12S,14R,15S,16R,17S)-17-benzyl-5-hydroxy-5,7,14,15-tetramethyl-19-oxo-13-oxa-18-azatetracyclo[9.8.0.01,16.012,14]nonadeca-3,9-dien-2-yl] acetate |
| Canonical SMILES | CC1CC=CC2C3C(O3)(C(C4C2(C(C=CC(C1)(C)O)OC(=O)C)C(=O)NC4CC5=CC=CC=C5)C)C |
| InChI | InChI=1S/C30H39NO5/c1-18-10-9-13-22-26-29(5,36-26)19(2)25-23(16-21-11-7-6-8-12-21)31-27(33)30(22,25)24(35-20(3)32)14-15-28(4,34)17-18/h6-9,11-15,18-19,22-26,34H,10,16-17H2,1-5H3,(H,31,33)/b13-9+,15-14+/t18-,19-,22-,23-,24+,25-,26-,28-,29+,30+/m0/s1 |
| InChI Key | QHZKOXCMCJMHJE-UPDPWUGUSA-N |
Properties
| Boiling Point | 647.9±55.0°C at 760 mmHg |
| Melting Point | 128-130°C |
| Density | 1.2±0.1 g/cm3 |
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. Epoxycytochalasin H: An Endophytic Phomopsis Compound Induces Apoptosis in A2780 Cells Through Mitochondrial Damage and Endoplasmic Reticulum Stress
Jiabin Wang, Zhonghang Xu, Xiaoqing Hu, Yimeng Yang, Jing Su, Yanan Liu, Li Zhou, Jianchun Qin, Dawei Zhang, Huimei Yu Onco Targets Ther. 2020 Jun 3;13:4987-4997. doi: 10.2147/OTT.S253716. eCollection 2020.
Background: Natural compounds extracted from plants have been reported to have antitumor activity. A fungal metabolite from Phomopsis, identified as epoxycytochalasin H and isolated from the flowering plant Polygonatum sibiricum, was found to have significant antitumor activity. In this study, we report the antitumor effects and mechanism of action of epoxycytochalasin H in the ovarian cancer cell line A2780. Our data suggest that epoxycytochalasin H markedly reduces cell proliferation and induces apoptosis in ovarian cancer cells. Materials and methods: The viability, apoptosis and colony formation of A2780 cells, treated with epoxycytochalasin H, were detected by MTT assay, nuclear staining, flow cytometry, and clone formation assay. MitoROS and mitochondrial membrane potentials were detected by MitoSOX staining and flow cytometry. The expression of proteins associated with apoptosis, autophagy, and endoplasmic reticulum stress, in A2780 cells treated with epoxycytochalasin H, was detected by Western blot. Effects of mitophagy were detected in Parkin-overexpressing 293T cells. Results: Our data suggested that epoxycytochalasin H could strongly reduce cell proliferation and induce apoptosis in ovarian cancer cell line A2780. Epoxycytochalasin H induced apoptosis through mitochondrial injury, mitophagy, and endoplasmic reticulum stress. Specifically, epoxycytochalasin H increased ROS level in cells, and in mitochondria, it decreased mitochondrial membrane potential, caused mitochondrial injury, activated macroautophagy and mitophagy, and subsequently induced apoptosis via the mitochondrial pathway. Additionally, it was discovered that epoxycytochalasin H could induce apoptosis more significantly in 293T cells overexpressing Parkin than in the parental cells. Thus, the mitophagy activated by epoxycytochalasin H could promote apoptosis. In addition, epoxycytochalasin H mediated endoplasmic reticulum stress-related apoptosis. Conclusion: Epoxycytochalasin H could promote apoptosis of human ovarian cancer A2780 cells by activating mitochondrial and endoplasmic reticulum stress-related apoptotic pathways.
3. LC-PDA-MS/MS-Based Dereplication Guided Isolation of a New Optical Isomer of 19,20-Epoxycytochalasin-N and Its Cytotoxic Activity
Manoj Kushwaha, Arem Qayum, Nisha Sharma, Vidushi Abrol, Poonam Choudhary, Mohd Murtaza, Shashank K Singh, Ram A Vishwakarma, Umesh Goutam, Shreyans K Jain, Sundeep Jaglan ACS Omega. 2022 Aug 10;7(33):29135-29141. doi: 10.1021/acsomega.2c03037. eCollection 2022 Aug 23.
The Rosellinia sanctae-cruciana extract was subjected to detailed liquid chromatography tandem mass spectrometry studies. A total of 38 peaks were annotated to m/z 508.26, m/z 510.28, m/z 524.26, m/z 526.28, m/z 540.26, m/z 542.27, and m/z 584.28 [M + H]+. The accurate mass, mutually supported UV/vis spectra, and database search identified these compounds as cytochalasins. Systematic dereplication helped identify a peak at m/z 540.26 [M + H]+ as the new compound. Further, the identified compound was purified by high-performance liquid chromatography and characterized by 2D NMR to be 19,20-epoxycytochalasin N1, a new optical isomer of 19,20-epoxycytochalasin-N. It exhibited substantial cytotoxicity with IC50 values ranging from 1.34 to 19.02 μM. This study shows a fast approach for dereplicating and identifying novel cytochalasin metabolites in crude extracts.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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