Chlorophyllin
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Basic Info
| Common Name | Chlorophyllin(F04140) |
| 2D Structure | |
| Description | Chlorophyllin is a sodium/copper derivative of chlorophyll. It is used as a food coloring agent and it some pharmaceutical products for treatment and odor control of wounds, injuries, and other skin conditions. Copper is a chemical element with the symbol Cu and atomic number 29. Copper is an essential elements in plants and animals as it is required for the normal functioning of more than 30 enzymes. It occurs naturally throughout the environment in rocks, soil, water, and air. (L277, L278, L285) |
| FRCD ID | F04140 |
| CAS Number | 11006-34-1 |
| PubChem CID | 123798 |
| Formula | C34H34MgN4O6 |
| IUPAC Name | magnesium;3-[20-(carboxylatomethyl)-18-(dioxidomethylidene)-8-ethenyl-13-ethyl-3,7,12,17-tetramethyl-2,3-dihydroporphyrin-23-id-2-yl]propanoate;hydron |
| InChI Key | UVOXKYYHMDAWNK-UHFFFAOYSA-L |
| InChI | InChI=1S/C34H36N4O6.Mg/c1-7-19-15(3)23-12-25-17(5)21(9-10-29(39)40)32(37-25)22(11-30(41)42)33-31(34(43)44)18(6)26(38-33)14-28-20(8-2)16(4)24(36-28)13-27(19)35-23;/h7,12-14,17,21H,1,8-11H2,2-6H3,(H5,35,36,37,38,39,40,41,42,43,44);/q;+2/p-2 |
| Canonical SMILES | [H+].[H+].[H+].CCC1=C(C2=CC3=NC(=CC4=NC(=C(C5=NC(=C(C5=C([O-])[O-])C)C=C1[N-]2)CC(=O)[O-])C(C4C)CCC(=O)[O-])C(=C3C=C)C)C.[Mg+2] |
| Isomeric SMILES | [H+].[H+].[H+].CCC1=C(C2=CC3=NC(=CC4=NC(=C(C5=NC(=C(C5=C([O-])[O-])C)C=C1[N-]2)CC(=O)[O-])C(C4C)CCC(=O)[O-])C(=C3C=C)C)C.[Mg+2] |
| Synonyms |
Magnesate(3-), ((7S,8S)-3-carboxy-5-(carboxymethyl)-13-ethenyl-18-ethyl-7,8-dihydro-2,8,12,17-tetramethyl-21H,23H-porphine-7-propanoato(5-)-kappa,N21,kappaN22,kappaN23,kappaN24)-, trihydrogen, (SP-4-2)-
Chlorophyllin A
15611-43-5
Magnesate(3-), (18-carboxy-20-(carboxymethyl)-8-ethenyl-13-ethyl-2,3-dihydro-3,7,12,17-tetramethyl-21H,23H-porphine-2-propanoato(5-)-N(21),N(22),N(23),N(24))-, trihydrogen, (SP-4-2-(2S-trans))-
CCRIS 8573
AC1L3XBA
LS-88577
11006-34-1 (hydrochloride-copper complex)
11006-92-1
37348-48-4
|
| Classifies |
Predicted: Plant Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Tetrapyrroles and derivatives |
| Subclass | Metallotetrapyrroles |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Metallotetrapyrroles |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Metallotetrapyrrole skeleton - Dicarboxylic acid or derivatives - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Pyrroline - Carboxylic acid salt - Ketene acetal or derivatives - Ketimine - Carboxylic acid derivative - Carboxylic acid - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Imine - Organic oxygen compound - Organic salt - Organic nitrogen compound - Organic zwitterion - Carbonyl group - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 618.973 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 10 |
| Rotatable Bond Count | 5 |
| Complexity | 1750 |
| Monoisotopic Mass | 618.233 |
| Exact Mass | 618.233 |
| Formal Charge | 0 |
| Heavy Atom Count | 45 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 5 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Pathological and biochemical evaluation of coumarin and chlorophyllin against aflatoxicosis in rat. | Exp Toxicol Pathol | 2017 Jun 14 | 28190563 |
| Chlorophylls and their Derivatives Used in Food Industry and Medicine. | Mini Rev Med Chem | 2017 | 27719668 |
| Toxicity of Chlorophyllin against Lymnaea acuminata at Different Wavelengths of Visible Light. | Trop Life Sci Res | 2016 Aug | 27688849 |
| Effective photosensitization-based inactivation of Gram (-) food pathogens andmolds using the chlorophyllin-chitosan complex: towards photoactive ediblecoatings to preserve strawberries. | Photochem Photobiol Sci | 2016 Apr | 26947225 |
| Experimental application of Lactobacillus fermentum CCM 7421 in combination with chlorophyllin in dogs. | Appl Microbiol Biotechnol | 2015 Oct | 26062536 |
| In vitro genotoxicity of mycotoxins ochratoxin A and fumonisin B(1) could be prevented by sodium copper chlorophyllin--implication to their genotoxic mechanism. | Food Chem | 2015 Mar 1 | 25306371 |
| The development of chlorophyll-based markers in poultry diets to aid detection offluorescent fecal contamination. | Poult Sci | 2013 Dec | 24235236 |
| Anticarcinogenic effect of probiotic fermented milk and chlorophyllin on aflatoxin-B₁-induced liver carcinogenesis in rats. | Br J Nutr | 2012 Apr | 21816119 |
| Present and future directions of translational research on aflatoxin and hepatocellular carcinoma. A review. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2012 | 21623489 |
| Effect of probiotic fermented milk and chlorophyllin on gene expressions and genotoxicity during AFB₁-induced hepatocellular carcinoma. | Gene | 2011 Dec 15 | 21963996 |
| Structural requirements for mutation formation from polycyclic aromatic hydrocarbon dihydrodiol epoxides in their interaction with food chemopreventive compounds. | Food Chem Toxicol | 2011 Apr | 21172398 |
| Natural faecal fluorophores and the potential of chlorophyll based markers tooptimise fluorescence as a real-time solution for the detection of faecalcontamination on carcasses. | Meat Sci | 2010 Dec | 20813464 |
| Applicability of an in vitro digestion model in assessing the bioaccessibility of mycotoxins from food. | Food Chem Toxicol | 2005 Jan | 15582193 |
| Method development and HPLC analysis of retail foods and beverages for copperchlorophyll (E141[i]) and chlorophyllin (E141[ii]) food colouring materials. | Food Addit Contam | 2005 Dec | 16356879 |
| Chemoprevention of hepatocellular carcinoma in aflatoxin endemic areas. | Gastroenterology | 2004 Nov | 15508099 |
| DNA adducts with chlorophyll and chlorophyllin as antimutagenic agents:synthesis, stability, and structural features. | Methods Mol Biol | 2004 | 15187278 |
| Chemoprevention with chlorophyllin in individuals exposed to dietary aflatoxin. | Mutat Res | 2003 Feb-Mar | 12628519 |
| Preventive effects of anthraquinone food pigments on the DNA damage induced bycarcinogens in Drosophila. | Mutat Res | 2001 Sep 1 | 11506807 |
| Chlorophyllin intervention reduces aflatoxin-DNA adducts in individuals at high risk for liver cancer. | Proc Natl Acad Sci U S A | 2001 Dec 4 | 11724948 |
| Mechanisms of chlorophyllin anticarcinogenesis: dose-responsive inhibition of aflatoxin uptake and biodistribution following oral co-administration in rainbow trout. | Toxicol Appl Pharmacol | 1999 Jul 15 | 10406928 |
Targets
- General Function:
- Nadp binding
- Specific Function:
- Maintains high levels of reduced glutathione in the cytosol.
- Gene Name:
- GSR
- Uniprot ID:
- P00390
- Molecular Weight:
- 56256.565 Da
- Mechanism of Action:
- Excess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia.
References
- Brewer GJ: A brand new mechanism for copper toxicity. J Hepatol. 2007 Oct;47(4):621-2. Epub 2007 Jul 23. [17697726 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
- Gene Name:
- PON1
- Uniprot ID:
- P27169
- Molecular Weight:
- 39730.99 Da
- Mechanism of Action:
- Excess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia.
References
- Brewer GJ: A brand new mechanism for copper toxicity. J Hepatol. 2007 Oct;47(4):621-2. Epub 2007 Jul 23. [17697726 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
- Gene Name:
- PON3
- Uniprot ID:
- Q15166
- Molecular Weight:
- 39607.185 Da
- Mechanism of Action:
- Excess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia.
References
- Brewer GJ: A brand new mechanism for copper toxicity. J Hepatol. 2007 Oct;47(4):621-2. Epub 2007 Jul 23. [17697726 ]
- Gene Name:
- SNCA
- Uniprot ID:
- P37840
- Molecular Weight:
- 14460.155 Da
- Mechanism of Action:
- Copper binds to alpha-synuclein, initiating protein aggregation and likely contributing to the development of the neurodegenerative disorders Parkinson's disease and Alzheimer's disease.
References
- Davies P, Fontaine SN, Moualla D, Wang X, Wright JA, Brown DR: Amyloidogenic metal-binding proteins: new investigative pathways. Biochem Soc Trans. 2008 Dec;36(Pt 6):1299-303. doi: 10.1042/BST0361299. [19021544 ]
- General Function:
- Transition metal ion binding
- Specific Function:
- Functions as a cell surface receptor and performs physiological functions on the surface of neurons relevant to neurite growth, neuronal adhesion and axonogenesis. Involved in cell mobility and transcription regulation through protein-protein interactions. Can promote transcription activation through binding to APBB1-KAT5 and inhibits Notch signaling through interaction with Numb. Couples to apoptosis-inducing pathways such as those mediated by G(O) and JIP. Inhibits G(o) alpha ATPase activity (By similarity). Acts as a kinesin I membrane receptor, mediating the axonal transport of beta-secretase and presenilin 1. Involved in copper homeostasis/oxidative stress through copper ion reduction. In vitro, copper-metallated APP induces neuronal death directly or is potentiated through Cu(2+)-mediated low-density lipoprotein oxidation. Can regulate neurite outgrowth through binding to components of the extracellular matrix such as heparin and collagen I and IV. The splice isoforms that contain the BPTI domain possess protease inhibitor activity. Induces a AGER-dependent pathway that involves activation of p38 MAPK, resulting in internalization of amyloid-beta peptide and leading to mitochondrial dysfunction in cultured cortical neurons. Provides Cu(2+) ions for GPC1 which are required for release of nitric oxide (NO) and subsequent degradation of the heparan sulfate chains on GPC1.Beta-amyloid peptides are lipophilic metal chelators with metal-reducing activity. Bind transient metals such as copper, zinc and iron. In vitro, can reduce Cu(2+) and Fe(3+) to Cu(+) and Fe(2+), respectively. Beta-amyloid 42 is a more effective reductant than beta-amyloid 40. Beta-amyloid peptides bind to lipoproteins and apolipoproteins E and J in the CSF and to HDL particles in plasma, inhibiting metal-catalyzed oxidation of lipoproteins. Beta-APP42 may activate mononuclear phagocytes in the brain and elicit inflammatory responses. Promotes both tau aggregation and TPK II-mediated phosphorylation. Interaction with overexpressed HADH2 leads to oxidative stress and neurotoxicity. Also binds GPC1 in lipid rafts.Appicans elicit adhesion of neural cells to the extracellular matrix and may regulate neurite outgrowth in the brain.The gamma-CTF peptides as well as the caspase-cleaved peptides, including C31, are potent enhancers of neuronal apoptosis.N-APP binds TNFRSF21 triggering caspase activation and degeneration of both neuronal cell bodies (via caspase-3) and axons (via caspase-6).
- Gene Name:
- APP
- Uniprot ID:
- P05067
- Molecular Weight:
- 86942.715 Da
- Mechanism of Action:
- Copper binds the N-terminal region of amyloid precursor protein, promoting the generation of _-amyloid from the protein. This is believed to contribute to the development of the neurodegenerative disorders Parkinson's disease and Alzheimer's disease.
References
- Davies P, Fontaine SN, Moualla D, Wang X, Wright JA, Brown DR: Amyloidogenic metal-binding proteins: new investigative pathways. Biochem Soc Trans. 2008 Dec;36(Pt 6):1299-303. doi: 10.1042/BST0361299. [19021544 ]
- General Function:
- Protein homodimerization activity
- Specific Function:
- Catalyzes the rate-limiting step of the oxidative pentose-phosphate pathway, which represents a route for the dissimilation of carbohydrates besides glycolysis. The main function of this enzyme is to provide reducing power (NADPH) and pentose phosphates for fatty acid and nucleic acid synthesis.
- Gene Name:
- G6PD
- Uniprot ID:
- P11413
- Molecular Weight:
- 59256.31 Da
- Mechanism of Action:
- Excess copper is sequestered within hepatocyte lysosomes, where it is complexed with metallothionein. Copper hepatotoxicity is believed to occur when the lysosomes become saturated and copper accumulates in the nucleus, causing nuclear damage. This damage is possibly a result of oxidative damage, including lipid peroxidation. Copper inhibits the sulfhydryl group enzymes such as glucose-6-phosphate 1-dehydrogenase, glutathione reductase, and paraoxonases, which protect the cell from free oxygen radicals. It also influences gene expression and is a co-factor for oxidative enzymes such as cytochrome C oxidase and lysyl oxidase. In addition, the oxidative stress induced by copper is thought to activate acid sphingomyelinase, which lead to the production of ceramide, an apoptotic signal, as well as cause hemolytic anemia.
References
- Brewer GJ: A brand new mechanism for copper toxicity. J Hepatol. 2007 Oct;47(4):621-2. Epub 2007 Jul 23. [17697726 ]