Girolline
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| Category | Bioactive by-products |
| Catalog number | BBF-01794 |
| CAS | 110883-46-0 |
| Molecular Weight | 190.63 |
| Molecular Formula | C6H11ClN4O |
| Purity | 95% |
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Description
It is produced by the strain of Pseudaxinyssa cantharella. It can inhibit protein biosynthesis and has anti-tumor effect.
Specification
| Synonyms | Giracodazole; Girodazole; Giracodazolum; (alphaS)-2-Amino-alpha-((1S)-2-amino-1-chloroethyl)imidazole-4-methanol; (1S,2S)-1-(2-Amino-5-imidazolyl)-2-chloro-3-amino-1-propanol |
| IUPAC Name | (1S,2S)-3-amino-1-(2-amino-1H-imidazol-5-yl)-2-chloropropan-1-ol |
| Canonical SMILES | C1=C(NC(=N1)N)C(C(CN)Cl)O |
| InChI | InChI=1S/C6H11ClN4O/c7-3(1-8)5(12)4-2-10-6(9)11-4/h2-3,5,12H,1,8H2,(H3,9,10,11)/t3-,5+/m0/s1 |
| InChI Key | YILCGOCHVFQMTC-WVZVXSGGSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Neoplastics (Tumor) |
| Boiling Point | 510.7±60.0 °C (Predicted) |
| Density | 1.509±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Antimalarial natural products of marine and freshwater origin
Karl Gademann, Joanna Kobylinska Chem Rec. 2009;9(3):187-98. doi: 10.1002/tcr.200900001.
This review highlights recently discovered antimalarial natural products from marine and freshwater sources described in the literature from 2006 to 2008. The structures as well as bioactivities of compounds against the malaria parasites such as Plasmodium falciparum are discussed, including, for example, agelasine, xestoquinone, alisiaquinone, crambescidin, venturamide, dragomabin, gragonamide, viridamide, salinosporamide, chaetoxanthone, nodulisporacid, tumonoic acid, girolline, oroidin, nostocarboline, aerucyclamide, and microcylamide 7806 and its revised structure. Synthetic derivatives of natural products are presented including plakortin, isoaaptamine, curcuphenol, pseudopyronine, manzamine, and nostocarboline. Consequences of these discoveries for the development of novel natural product agents against malaria are discussed.
2. [Study on natural products for drug development]
Sachiko Tsukamoto Yakugaku Zasshi. 2010 Oct;130(10):1273-81. doi: 10.1248/yakushi.130.1273.
The ubiquitin-proteasome system (UPS) plays a major role in selective protein degradation and regulates various cellular events. Approval of bortezomib for the treatment of multiple myeloma validated the proteasome as an anticancer target. In order to find drug candidates targeting the ubiquitin-dependent protein degradation, we paid an attention to inhibitors against three enzymes, ubiquitin-activating enzyme (E1), ubiquitin-conjugating enzyme (E2), and ubiquitin-protein ligase (E3), which are required for polyubiquitination of proteins and prerequisite to proteasome-mediated protein degradation. We succeeded in isolating various compounds with three distinct inhibitory activities against an E1 enzyme reaction, Ubc13 (E2)-Uev1A interaction, and p53-HDM2 (E3) interaction as well as the proteasome inhibitors. We also isolated new alkaloids, notoamides, from a marine-derived Aspergillus sp. Among them, notoamide B and stephacidin A contain a bicyclo[2.2.2]diazaoctane ring in their structures. We proposed this ring is constructed from notoamide E by the intramolecular Diels-Alder (IMDA) reaction. Recently, the isolation of the antipodes of notoamides from the terrestrial Aspergillus has been reported. We propose that each enantiomer is generated by a distinct face-selective IMDA.
3. Unbiased screening of marine sponge extracts for anti-inflammatory agents combined with chemical genomics identifies girolline as an inhibitor of protein synthesis
Shan-Yu Fung, Vladimir Sofiyev, Julia Schneiderman, Aaron F Hirschfeld, Rachel E Victor, Kate Woods, Jeff S Piotrowski, Raamesh Deshpande, Sheena C Li, Nicole J de Voogd, Chad L Myers, Charlie Boone, Raymond J Andersen, Stuart E Turvey ACS Chem Biol. 2014 Jan 17;9(1):247-57. doi: 10.1021/cb400740c. Epub 2013 Oct 29.
Toll-like receptors (TLRs) play a critical role in innate immunity, but activation of TLR signaling pathways is also associated with many harmful inflammatory diseases. Identification of novel anti-inflammatory molecules targeting TLR signaling pathways is central to the development of new treatment approaches for acute and chronic inflammation. We performed high-throughput screening from crude marine sponge extracts on TLR5 signaling and identified girolline. We demonstrated that girolline inhibits signaling through both MyD88-dependent and -independent TLRs (i.e., TLR2, 3, 4, 5, and 7) and reduces cytokine (IL-6 and IL-8) production in human peripheral blood mononuclear cells and macrophages. Using a chemical genomics approach, we identified Elongation Factor 2 as the molecular target of girolline, which inhibits protein synthesis at the elongation step. Together these data identify the sponge natural product girolline as a potential anti-inflammatory agent acting through inhibition of protein synthesis.
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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 ╳
