Monorden D
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| Category | Others |
| Catalog number | BBF-02563 |
| CAS | 544712-82-5 |
| Molecular Weight | 350.79 |
| Molecular Formula | C18H19ClO5 |
| Purity | >98% |
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Description
Monorden D is a metabolite of Humicola sp. FO-2942. It has the effect of arresting the cell cycle of Jurket cells in G1 and G2/M phases. It has anti-Aspergillus niger activity.
Specification
| Synonyms | Pochonin D |
| Storage | 3 years -20oC powder, 6 months-80oC in solvent. |
| IUPAC Name | (4R,6E,10E)-15-chloro-16,18-dihydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,10,15,17-pentaene-2,12-dione |
| Canonical SMILES | CC1CC=CCCC=CC(=O)CC2=C(C(=CC(=C2Cl)O)O)C(=O)O1 |
| InChI | InChI=1S/C18H19ClO5/c1-11-7-5-3-2-4-6-8-12(20)9-13-16(18(23)24-11)14(21)10-15(22)17(13)19/h3,5-6,8,10-11,21-22H,2,4,7,9H2,1H3/b5-3+,8-6+/t11-/m1/s1 |
| InChI Key | FJVQHTGEXYKKBS-CJRGTMQESA-N |
Properties
| Appearance | Yellow Oil |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 609.6±55.0°C at 760 mmHg |
| Melting Point | 84°C |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Heat shock protein 90 inhibitors suppress pyroptosis in THP-1 cells
Mingui Fu, Yisong Qian, Cynthia Liu, Xiuzhen Li, Zhou Zhou, Xiaotian Huang Biochem J . 2020 Oct 30;477(20):3923-3934. doi: 10.1042/BCJ20200351.
Pyroptosis is a recently discovered inflammatory form of programmed cell death which is mostly triggered by infection with intracellular pathogens and critically contributes to inflammation. Mitigating pyroptosis may be a potential therapeutic target in inflammatory diseases. However, small chemicals to reduce pyroptosis is still elusive. In the present study, we screened 155 chemicals from a microbial natural product library and found Geldanamycin, an HSP90 inhibitor, profoundly rescued THP-1 cells from pyroptosis induced by LPS plus Nigericin treatment. Consistently, other HSP90 inhibitors, including Radicicol, 17-DMAG and 17-AAG, all ameliorated pyroptosis in THP-1 cells by suppressing the inflammasome/Caspase-1/GSDMD signal pathway in pyroptosis. HSP90 inhibition compromised the protein stability of NLRP3, a critical component of the inflammasome. Moreover, up-regulated HSP70 may also contribute to this effect. HSP90 inhibition may thus be a potential therapeutic strategy in the treatment of inflammatory diseases in which pyroptosis plays a role.
2. Pochonins A-F, new antiviral and antiparasitic resorcylic acid lactones from Pochonia chlamydosporia var. catenulata
Anke Mayer-Bartschmid, Gisela Greif, Hartwig Müller, Gerald Kleymann, Werner Zitzmann, Marc Stadler, Veronika Hellwig, Hans-Volker Tichy J Nat Prod . 2003 Jun;66(6):829-37. doi: 10.1021/np020556v.
Monorden (1) and the novel resorcylic acid lactones pochonins A (2), B (4), C (6), D (7), and E (8) as well as tetrahydromonorden (5) and pseurotin A (22) were isolated from cultures of the clavicipitaceous hyphomycete Pochonia chlamydosporia var. catenulata strain P 0297. Fermentation of P 0297 in bromide-containing culture media led to a shift in secondary metabolite production and yielded monocillins III (3) and II (9) as major metabolites besides monorden (1) as well as the novel compounds pochonin F (10) and a monocillin II glycoside (11) as minor metabolites. Most of these compounds showed moderate activities in a cellular replication assay against Herpes Simplex Virus 1 (HSV1) and against the parasitic protozoan Eimeria tenella. In contrast to the structurally related zearalenone derivatives none of the metabolites of strain P 0297 were found to be active in a fluorescence polarization assay for determination of modulatory activities on the human estrogenic receptor ERbeta. Beta-zearalenol (17), but not zearalenone (15) and alpha-zearalenol (16), showed antiherpetic effects. We report the production, isolation, and structure elucidation of compounds 1-11 and their biological characterization.
3. Study of marine natural products including resorcyclic acid lactones from Humicola fuscoatra that reactivate latent HIV-1 expression in an in vitro model of central memory CD4+ T cells
Kimberly N White, Romas Geleziunas, Nikos Pagratis, Yang Tian, Helen Yu, Eric J Mejia, Steven T Loveridge, Tiffany Barnes, Angela Tsai, Tomas Cihlar, George Stepan, Gregg S Jones, Karen Tenney, Phillip Crews, Marija Drašković, Manuel Tsiang J Nat Prod . 2014 Mar 28;77(3):618-24. doi: 10.1021/np400889x.
An extract of Humicola fuscoatra (UCSC strain no. 108111A) was shown to reactivate latent HIV-1 expression in an in vitro model of central memory CD4+ T cells. We report the bioassay-guided isolation and structure determination of several resorcyclic acid lactones, including four known compounds, radicicol (1, aka. monorden) and pochonins B (2), C (3), and N (4), and three new analogues, radicicols B-D (5-7). Compounds 1-3 and 5 showed moderate activities in the memory T cell model of HIV-1 latency. Radicicol (1) displayed lower potency in reactivating latent HIV-1 (EC50 = 9.1 μM) relative to the HDAC inhibitors apicidin (EC50 = 0.3 μM), romidepsin (EC50 = 0.003 μM), and SAHA (EC50 = 0.6 μM); however, it achieved equivalent maximum efficacy relative to the positive control compounds (98% of SAHA and romidepsin).
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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 ╳
