Ferroverdin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00922 |
| CAS | |
| Molecular Weight | 907.61 |
| Molecular Formula | C46H33FeN3O14 |
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Description
Ferroverdin C is a cholesteryl ester transfer protein (CETP) inhibitor produced by Streptomyces sp. WK-5344. It inhibits human CETP with an IC50 of 2.2 μg/ml.
Specification
| IUPAC Name | (4-ethenylphenyl) 4-hydroxy-3-nitrosobenzoate;(Z)-3-[4-(4-hydroxy-3-nitrosobenzoyl)oxyphenyl]prop-2-enoic acid;iron(2+) |
| Canonical SMILES | C=CC1=CC=C(C=C1)OC(=O)C2=CC(=C(C=C2)O)N=O.C=CC1=CC=C(C=C1)OC(=O)C2=CC(=C(C=C2)O)N=O.C1=CC(=CC=C1C=CC(=O)O)OC(=O)C2=CC(=C(C=C2)O)N=O.[Fe+2] |
| InChI | InChI=1S/C16H11NO6.2C15H11NO4.Fe/c18-14-7-4-11(9-13(14)17-22)16(21)23-12-5-1-10(2-6-12)3-8-15(19)20;2*1-2-10-3-6-12(7-4-10)20-15(18)11-5-8-14(17)13(9-11)16-19;/h1-9,18H,(H,19,20);2*2-9,17H,1H2;/q;;;+2/b8-3-;;; |
| InChI Key | HQZNHTMRMVPRCO-XYAGXRERSA-N |
Properties
| Appearance | Green Powder |
Reference Reading
1. Structure of New Ferroverdins Recruiting Unconventional Ferrous Iron Chelating Agents
Loïc Martinet, Dominique Baiwir, Gabriel Mazzucchelli, Sébastien Rigali Biomolecules. 2022 May 26;12(6):752. doi: 10.3390/biom12060752.
Ferroverdins are ferrous iron (Fe2+)-nitrosophenolato complexes produced by a few Streptomyces species as a response to iron overload. Previously, three ferroverdins were identified: ferroverdin A, in which three molecules of p-vinylphenyl-3-nitroso-4-hydroxybenzoate (p-vinylphenyl-3,4-NHBA) are recruited to bind Fe2+, and Ferroverdin B and Ferroverdin C, in which one molecule of p-vinylphenyl-3,4-NHBA is substituted by hydroxy-p-vinylphenyl-3,4-NHBA, and by carboxy-p-vinylphenyl-3,4-NHBA, respectively. These molecules, especially ferroverdin B, are potent inhibitors of the human cholesteryl ester transfer protein (CETP) and therefore candidate hits for the development of drugs that increase the serum concentration of high-density lipoprotein cholesterol, thereby diminishing the risk of atherosclerotic cardiovascular disease. In this work, we used high-resolution mass spectrometry combined with tandem mass spectrometry to identify 43 novel ferroverdins from the cytosol of two Streptomyces lunaelactis species. For 13 of them (designated ferroverdins C2, C3, D, D2, D3, E, F, G, H, CD, DE, DF, and DG), we could elucidate their structure, and for the other 17 new ferroverdins, ambiguity remains for one of the three ligands. p-formylphenyl-3,4-NHBA, p-benzoic acid-3,4-NHBA, 3,4-NHBA, p-phenylpropionate-3,4-NHBA, and p-phenyacetate-3,4-NHBA were identified as new alternative chelators for Fe2+-binding, and two compounds (C3 and D3) are the first reported ferroverdins that do not recruit p-vinylphenyl-3,4-NHBA. Our work thus uncovered putative novel CETP inhibitors or ferroverdins with novel bioactivities.
2. Ferroverdins, inhibitors of cholesteryl ester transfer protein produced by Streptomyces sp. WK-5344. II. Structure elucidation
N Tabata, H Tomoda, S Omura J Antibiot (Tokyo). 1999 Dec;52(12):1108-13. doi: 10.7164/antibiotics.52.1108.
The structures of ferroverdins B and C, novel inhibitors of cholesteryl ester transfer protein, were elucidated by spectroscopic studies including various NMR measurements. They are the complex between one Fe2+ and three ligands, that is, two common p-vinylphenyl-3-nitroso-4-hydroxybenzoates and one hydroxy p-vinylphenyl-3-nitroso-4-hydroxybenzoate for ferroverdin B and one carboxylic acid p-vinylphenyl-3-nitroso-4-hydroxybenzoate for ferroverdin C.
3. Ferroverdins, inhibitors of cholesteryl ester transfer protein produced by Streptomyces sp. WK-5344. I. Production, isolation and biological properties
H Tomoda, N Tabata, M Shinose, Y Takahashi, H B Woodruff, S Omura J Antibiot (Tokyo). 1999 Dec;52(12):1101-7. doi: 10.7164/antibiotics.52.1101.
Streptomyces sp. WK-5344, a soil isolate, was found to produce structurally related inhibitors of cholesteryl ester transfer protein (CETP). New active compounds, designated ferroverdins B and C, were isolated along with known ferroverdin A from the fermentation broth by solvent extraction, ODS column chromatography and silica gel column chromatography. All ferroverdins showed a dose-dependent inhibitory activity against human CETP. The IC50 values were 21, 0.62 and 2.2 microM for ferroverdins A, B and C, respectively, indicating that ferroverdin B is one of the most potent CETP inhibitors of microbial origin.
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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 ╳
