Monorden C
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| Category | Others |
| Catalog number | BBF-02562 |
| CAS | 544712-80-3 |
| Molecular Weight | 366.79 |
| Molecular Formula | C18H19ClO6 |
| Purity | >98% |
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Description
Monorden C 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 A; 2H-Oxireno[e][2]benzoxacyclotetradecin-6,12(3H,7H)-dione, 8-chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-, (1aR,14S,15aR)- |
| IUPAC Name | (4S,6R,8R,11E)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),11,16,18-tetraene-2,13-dione |
| Canonical SMILES | CC1CC2C(O2)CCC=CC(=O)CC3=C(C(=CC(=C3Cl)O)O)C(=O)O1 |
| InChI | InChI=1S/C18H19ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2,4,8-9,14-15,21-22H,3,5-7H2,1H3/b4-2+/t9-,14+,15+/m0/s1 |
| InChI Key | WUSYBKJSCTYKMV-UUEMPHROSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 642.4±55.0°C at 760 mmHg |
| Melting Point | 158°C |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. The effects of space flight on the production of monorden by Humicola fuscoatra WC5157 in solid-state fermentation
D M Klaus, P B Fernandes, E J Pack, K S Lam, S Forenza, S W Mamber Appl Microbiol Biotechnol . 1998 May;49(5):579-83. doi: 10.1007/s002530051216.
The effect of space flight on the production of the antibiotic monorden on two types of agar media, T8 and PG, by Humicola fuscoatra WC5157 was examined on board the US Space Shuttle mission STS-77 in May 1996. Paired space-flight and ground control samples were prepared using identical hardware, protocol, media, and inoculum. Inoculation occurred simultaneously for both groups 2.5 after launch. The flight and ground samples were allowed to grow for the entire 10-day mission in a dark, thermally controlled (22 degrees C) environment. Post-flight HPLC analysis of the flight and ground sample extracts indicated that the production of monorden by H. fuscoatra WC5157 in the flight samples was higher than in the ground samples in both agar media. In the T8 medium, the production of monorden in the flight and ground samples was 11.6 +/- 3.5 micrograms and 8.9 +/- 1.1 micrograms respectively (30% increase). In the PG medium, the production of monorden in the flight and ground samples was 23.8 +/- 3.3 micrograms and 8.2 +/- 2.2 micrograms respectively (190% increase). The production of monorden in the flight and ground control samples was confirmed by HPLC-MS analysis.
2. Solution- and solid-phase synthesis of radicicol (monorden) and pochonin C
Emilie Moulin, Sofia Barluenga, Nicolas Winssinger, Pilar Lopez Chemistry . 2005 Aug 19;11(17):4935-52. doi: 10.1002/chem.200500160.
A modular synthesis for pochonin C and radicicol is reported. The two natural products were prepared in seven and eight steps, respectively, from three readily available fragments. Alternative syntheses of these compounds were achieved using a combination of polymer-bound reagents and solid phase reactions. The conformation of the two natural products was studied and compared by using 2D NMR spectroscopy.
3. Transcriptomics-Based Screening Identifies Pharmacological Inhibition of Hsp90 as a Means to Defer Aging
Alan Kavšek, Renée I Seinstra, Ellen A A Nollen, Ilke Sen, Nicholas Stroustrup, Georges E Janssens, Christian G Riedel, Lluís Millan-Ariño, Xin-Xuan Lin Cell Rep . 2019 Apr 9;27(2):467-480.e6. doi: 10.1016/j.celrep.2019.03.044.
Aging strongly influences human morbidity and mortality. Thus, aging-preventive compounds could greatly improve our health and lifespan. Here we screened for such compounds, known as geroprotectors, employing the power of transcriptomics to predict biological age. Using age-stratified human tissue transcriptomes and machine learning, we generated age classifiers and applied these to transcriptomic changes induced by 1,309 different compounds in human cells, ranking these compounds by their ability to induce a "youthful" transcriptional state. Testing the top candidates in C. elegans, we identified two Hsp90 inhibitors, monorden and tanespimycin, which extended the animals' lifespan and improved their health. Hsp90 inhibition induces expression of heat shock proteins known to improve protein homeostasis. Consistently, monorden treatment improved the survival of C. elegans under proteotoxic stress, and its benefits depended on the cytosolic unfolded protein response-inducing transcription factor HSF-1. Taken together, our method represents an innovative geroprotector screening approach and was able to identify a class that acts by improving protein homeostasis.
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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 ╳
