Pheophorbide
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| IUPAC name
(3S,4S)-9-Ethenyl-14-ethyl-21-(methoxycarbonyl)-4,8,13,18-tetramethyl-20-oxo-3-phorbinepropanoic acid | |
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3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.036.110 |
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PubChem CID |
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CompTox Dashboard (EPA) |
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| Properties | |
| C35H36N4O5 | |
| Molar mass | 592.68 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pheophorbide or phaeophorbide is a product of chlorophyll breakdown and a derivative of pheophytin where both the central magnesium has been removed and the phytol tail has been hydrolyzed. It is used as a photosensitizer in photodynamic therapy.[1]
Pheophorbide may be generated by digestion of ingested plant matter. Both worm (Caenorhabditis elegans) and mouse mitochondria are able to use the molecule in a form of ad hoc photoheterotrophy.[2]
In chlorophyll a metabolism
[edit]Pheophorbide is a product of chlorophyll breakdown and a derivative of pheophytin where both the central magnesium ion has been removed and the phytol tail has been hydrolyzed as plants senesce.[1][3]
Further reactions within the enzymes pheophorbide a oxygenase and red chlorophyll catabolite reductase convert pheophorbide via a red catabolite into a fluorescent final product.[4] The oxygenase is a Rieske protein containing an iron–sulfur cluster that requires reduced ferredoxin to function.[5] The reductase also requires ferredoxin.[6][7]
chlorophyll catabolite
The fluorescent product can exist in two diastereomeric forms. All plants in a given genera produce a single isomer.[4][8]
References
[edit]- 1 2 Chen, Kuan; Preuß, Annegret; Hackbarth, Steffen; Wacker, Matthias; Langer, Klaus; Röder, Beate (2009). "Novel photosensitizer-protein nanoparticles for Photodynamic therapy: Photophysical characterization and in vitro investigations". Journal of Photochemistry and Photobiology B: Biology. 96 (1): 66–74. doi:10.1016/j.jphotobiol.2009.04.006. PMID 19442534.
- ↑ Xu, Chen; Zhang, Junhua; Mihai, Doina M.; Washington, Ilyas (2014-01-15). "Light-harvesting chlorophyll pigments enable mammalian mitochondria to capture photonic energy and produce ATP". Journal of Cell Science. 127 (2): 388–399. doi:10.1242/jcs.134262. ISSN 0021-9533. PMC 6518289. PMID 24198392.
- ↑ Ougham, H.; Hörtensteiner, S.; Armstead, I.; Donnison, I.; King, I.; Thomas, H.; Mur, L. (2008). "The control of chlorophyll catabolism and the status of yellowing as a biomarker of leaf senescence". Plant Biology. 10: 4–14. doi:10.1111/j.1438-8677.2008.00081.x. PMID 18721307.
- 1 2 Pružinská, Adriana; Anders, Iwona; Aubry, Sylvain; Schenk, Nicole; Tapernoux-Lüthi, Esther; Müller, Thomas; Kräutler, Bernhard; Hörtensteiner, Stefan (2007). "In Vivo Participation of Red Chlorophyll Catabolite Reductase in Chlorophyll Breakdown". The Plant Cell. 19 (1): 369–387. doi:10.1105/tpc.106.044404. PMC 1820978. PMID 17237353.
- ↑ Pružinská, Adriana; Tanner, Gaby; Anders, Iwona; Roca, Maria; Hörtensteiner, Stefan (2003). "Chlorophyll breakdown: Pheophorbide a oxygenase is a Rieske-type iron–sulfur protein, encoded by the accelerated cell death 1 gene". Proceedings of the National Academy of Sciences. 100 (25): 15259–15264. doi:10.1073/pnas.2036571100. PMC 299977. PMID 14657372.
- ↑ Enzyme 1.3.7.12 at KEGG Pathway Database.
- ↑ Wüthrich, Karin L.; Bovet, Lucien; Hunziker, Peter E.; Donnison, Iain S.; Hörtensteiner, Stefan (2000). "Molecular cloning, functional expression and characterisation of RCC reductase involved in chlorophyll catabolism". The Plant Journal. 21 (2): 189–198. doi:10.1046/j.1365-313x.2000.00667.x. PMID 10743659.
- ↑ Hörtensteiner, S. (2006). "Chlorophyll Degradation During Senescence". Annual Review of Plant Biology. 57: 55–77. doi:10.1146/annurev.arplant.57.032905.105212. PMID 16669755.