Aszonalenin

Aszonalenin

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Category Antibiotics
Catalog number BBF-00126
CAS 81797-27-5
Molecular Weight 373.45
Molecular Formula C23H23N3O2

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Description

Aszonalenin is a nitrogen-containing heterocyclic antibiotic produced by Aspergillus zonatus. It can cause abnormal second division of sea urchin embryo.

Specification

IUPAC Name 10-(2-methylbut-3-en-2-yl)-1,3,14-triazapentacyclo[10.9.0.02,10.04,9.015,20]henicosa-4,6,8,15,17,19-hexaene-13,21-dione
Canonical SMILES CC(C)(C=C)C12CC3C(=O)NC4=CC=CC=C4C(=O)N3C1NC5=CC=CC=C25
InChI InChI=1S/C23H23N3O2/c1-4-22(2,3)23-13-18-19(27)24-16-11-7-5-9-14(16)20(28)26(18)21(23)25-17-12-8-6-10-15(17)23/h4-12,18,21,25H,1,13H2,2-3H3,(H,24,27)
InChI Key AVLMMDWEIUEKEK-UHFFFAOYSA-N

Properties

Appearance Colorless needle Crystal
Melting Point 244-247°C

Reference Reading

1. Anti-prostate cancer metabolites from the soil-derived Aspergillus neoniveus
Menna Fayek, Hassan Y Ebrahim, Heba E Elsayed, Mohamed S Abdel-Aziz, Benson M Kariuki, Fatma A Moharram Front Pharmacol. 2022 Oct 14;13:1006062. doi: 10.3389/fphar.2022.1006062. eCollection 2022.
Prostate cancer (PCa) ranks as one of the most commonly diagnosed malignancies worldwide. Toxicity, lack of clinical efficacy, and development of resistance phenotypes are the main challenges in the control of prostate malignancies. Notably, castration-resistance prostate cancer (CRPCa) is a highly aggressive and metastatic phenotype of the disease with a poor prognosis and very limited therapeutic options. Herein, we report the isolation and genotypic identification of a soil-derived fungus Aspergillus neoniveus using the PCR-based internal transcribed spacer (ITS) region amplification approach. HPLC/MS investigation of the metabolic profile of the ethyl acetate extract from the fungal biomass revealed tentative identification of forty-five compounds belonging to various chemical classes including γ-butyrolactones, alkaloids, phenolics, and quinoids. Furthermore, the chromatographic purification of microbial extract enabled the identification of nervonic acid methyl ester (1) for the first time from endophytic fungi, as well as acetyl aszonalenin (2), and butyrolactone II (3) for the first time from A. neoniveus. The chemical frameworks of the isolated compounds were identified via extensive spectral analysis including 1 and 2D NMR and MS. The X-ray crystal structure and absolute configuration of acetyl aszonalenin (2) were also determined. Additionally, screening of in vitro anticancer activity of the fungal extract revealed its potential antiproliferative and anti-migratory activities against five different prostate cancer cells (PC3, PC-3M, DU-145, CWR-R1ca, and 22Rv1), including different cells with the castration-resistance phenotype. Moreover, the isolated metabolites significantly inhibited the proliferation, migration, and colonization of human prostate cancer cells at low micromolar levels, thus providing credence for future investigation of these metabolites in relevant anti-prostate cancer animal models. Furthermore, computational target prediction tools identified the cannabinoid G-protein coupled receptors type 1 (CB1) as a potential biological target mediating, at least in part, the anticancer effects of acetylaszonalenin (2). Moreover, molecular modeling and docking studies revealed a favorable binding pose at the CB1 receptor orthosteric ligand pocket aided by multiple polar and hydrophobic interactions with critical amino acids. In conclusion, the Aspergillus neoniveus-derived prenylated indole alkaloid acetylaszonalenin has promising anticancer activity and is amenable to further hit-to-lead optimization for the control of prostate malignancies via modulating CB1 receptors.
2. Mechanism of two alkaloids isolated from coral endophytic fungus for suppressing angiogenesis in atherosclerotic plaque in HUVEC
Yi Liu, Yanmei Li, Minqi Chen, Yayue Liu, Jinyue Liang, Yi Zhang, Zhong-Ji Qian Int Immunopharmacol. 2022 Aug;109:108931. doi: 10.1016/j.intimp.2022.108931. Epub 2022 Jun 12.
Atherosclerosis is a significant cause of many cardiovascular diseases. Oxidized low-density lipoproteins (ox-LDL) are crucial in developing atherosclerosis. In this study, we researched the effects of two alkaloids epi-aszonalenin A (EAA) and aszonalenin (AZN) of an endophytic fungus Aspergillus terreus C23-3 from coral Pavona, on ox-LDL-induced inflammation, apoptosis and angiogenesis in HUVEC, and evaluated related factors and mechanism. The results reveal that EAA and AZN inhibit HUVEC migration, invasion, angiogenesis and reactive oxygen species (ROS) accumulation on a non-cytotoxic basis. Then, EAA and AZN suppressed the ox-LDL-induced of LOX-1, VEGF protein expression, MAPK and PI3K/AKT pathways phosphorylation. Furthermore, AZN suppressed the ox-LDL-induced inflammatory factors (IL-6, IL-1β, and TNF-α), intercellular adhesion molecule-1 (ICAM-1), vascular cell adhesion molecule-1 (VCAM-1) and VEGF receptor VEGFR-2 and platelet-derived growth factor PDGF. In addition, it inhibited ox-LDL-induced atherosclerosis by blocking inflammation and apoptosis through nuclear factor κB (NF-κB), cleaved-caspase-3 and Bax/Bcl-2 pathways. Molecular docking results confirm that the effect of AZN on atherosclerosis inhibitory activity may be attributed to hydrogen bonds formed into LOX-1 and VEGFR-2. These data indicate that EAA and AZN can effectively prevent ox-LDL-induced HUVEC damage and angiogenesis by inhibiting inflammation and apoptosis. Therefore, EAA and AZN may have potential beneficial effects in regulating atherosclerosis and plaque angiogenesis.
3. epi-Aszonalenin B from Aspergillus novofumigatus inhibits NF-κB activity induced by ZFTA-RELA fusion protein that drives ependymoma
Kazuki Ishikawa, Masaki Ishii, Takashi Yaguchi, Toshiaki Katada, Koji Ichinose, Shinya Ohata Biochem Biophys Res Commun. 2022 Mar 12;596:104-110. doi: 10.1016/j.bbrc.2022.01.076. Epub 2022 Jan 22.
Nuclear factor-kappa B (NF-κB) signaling is an intracellular signaling pathway involved in inflammatory responses and the pathogenesis of various cancers, including ependymoma, which is a rare and chemotherapy-resistant glioma. Several isoforms of fusion proteins that consist of a nuclear protein, zinc finger translocation associated (ZFTA), and RELA (ZFTA-RELA), an NF-κB-signaling effector transcription factor, cause excessive activation of the NF-κB signaling pathway and result in supratentorial ependymomas (ST-EPN-RELA). As inhibitors of NF-κB activity induced by ZFTA-RELA are expected to be therapeutic agents for ST-EPN-RELA, we established an NF-κB responsive luciferase reporter cell line that expresses the most common isoform of ZFTA-RELA in a doxycycline-dependent manner. Using this reporter cell line, we screened fungus extracts for compounds that inhibit the NF-κB activity induced by ZFTA-RELA expression and identified aszonalenin, an alkaloid from Aspergillus novofumigatus. We also purified analogs of aszonalenin, namely acetylaszonalenin and epi-aszonalenin B and C. In a luciferase assay using cells constitutively expressing luciferase (counter assay), acetylaszonalenin and epi-aszonalenin C showed non-specific inhibition of the luciferase activity. Aszonalenin and epi-aszonalenin B inhibited the NF-κB responsive luciferase activity by expressing ZFTA-RELA more strongly than the luciferase activity in the counter assay. The upregulation of endogenous NF-κB responsive genes, such as CCND1, ICAM1, and L1CAM, by ZFTA-RELA expression was inhibited by epi-aszonalenin B, but not by aszonalenin. This study suggests that epi-aszonalenin B may be a lead compound for the therapeutic development of ST-EPN-RELA.

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