Chlorophyll catabolites

In a few cases chlorophyll catabolites which had undergone ring cleavage between positions 20 and 1 were isolated as naturally occurring light-emitter substances from dinoflagcllates.47... 

RCC is very unstable and rapidly reduced to a primary fluorescent chlorophyll catabolite (pFCC) by red chlorophyll catabolite reductase (RCCR). In subsequent steps pFcc is converted to different fluorescent chlorophyll catabolites (FCCs). These chemically rather labile compounds are further converted into colorless nonfluorescing chlorophyll catabolites (NCCs) by a nonenzymatic deconjugation of the four... 

Prauinska, A. et ah. Chlorophyll breakdown in senescent Arabidopsis leaves Characterization of chlorophyll catabolites and of chlorophyll catabolic enzymes involved in the degreening reaction. Plant Physiol., 139, 52, 2005. 

Rodoni, S. et al.. Partial purification and characterization of red chlorophyll catabolite reductase, a stroma protein involved in chlorophyll breakdown. Plant Physiol, 115, 677, 1997. 

Oberhuber, M. and Krautler, B., Breakdown of chlorophyll electrochemical bilin reduction provides synthetic access to fluorescent chlorophyll catabolites, Chembio-chem, 3, 104, 2002. 

Oberhuber, M. et al.. Breakdown of chlorophyll A nonenzymatic reaction accounts for the formation of the colorless nonfluorescent chlorophyll catabolites, PNAS, 100, 6910, 2003. 

Losey, F.G. and Engel, N., Isolation and characterization of a urobilinogenoidic chlorophyll catabolite from Hordeum vulgare L., J. Biol. Chem., 276, 8643, 2001. 

Pruzinska, A. et ah. In vivo participation of red chlorophyll catabolite reducase in chlorophyll breakdown. The Plant Cell, 19, 369, 2007. 

FIGURE 4.1.1 Possible chlorophyll degradation pathways in plant tissues or in processed foods. Pheophorbide a monooxygenase is specific for pheophorbide a. RCC = red chlorophyll catabolite. FCC = fluorescent chlorophyll catabolite. NCC = non-fluorescent chlorophyll catabolite. 

The development and reports of methods for colorless chlorophyll derivative (RCCs, FCCs, and NCCs) analysis are relatively recent and the structures of the compounds are being elucidated by deduction from their chromatographic behaviors, spectral characteristics (UV-Vis absorbance spectra), mass spectrometry, and nuclear magnetic resonance analysis. The main obstacle is that these compounds do not accumulate in appreciable quantities in situ and, moreover, there are no standards for them. The determination of the enzymatic activities of red chlorophyll catabolite reductase (RCCR) and pheophorbide a monoxygenase (PAO) also helps to monitor the appearance of colorless derivatives since they are the key enzymes responsible for the loss of green color. ... 

Berghold, J. et al., Chlorophyll breakdown in tobacco on the structure of two non-fluorescent chlorophyll catabolites, Chemistry Biodiversity, 1, 657, 2004. 

Lu, Y.-P. et al., AtMRP2, an Arabidopsis ATP binding cassette transporter able to transport glutathione S-conjugates and chlorophyll catabolites functional comparisons with AtMRPl. Plant Cell, 10, 267, 1998. 

Krautler B, Hortensteiner S. Chlorophyll catabolites and the biochemistry of chlorophyll breakdown. In Chlorophylls and Bacteriochlorophylls Biochemistry, Biophysics, Functions and Applications. Grimm B, Porra R, Rudiger W, Scheer H, eds. 2006. Springer, Dordrecht, The Netherlands, pp. 237-260. 

Krautler B. Chlorophyll breakdown and chlorophyll catabolites. In The Porphyrin Handbook. Kadish KM, Smith KM, Guilard R, eds. 2002. Academic Press, Amsterdam, The Netherlands, pp. 183-210. 

An Enzyme-bound Red Chlorophyll Catabolite from Enzymatic... 

Fluorescent Chlorophyll Catabolites from Enzymatic Reduction... 

Transformation of Fluorescent Chlorophyll Catabolites to Non-fluorescent Colourless Chlorophyll Catabolites. 22... 

Chlorophyll Catabolites from the Green Alga Chlorella protothecoides... 30... 

This chapter reviews the occurrence, structure, and reactivity of chlorophyll catabolites from vascular plants and from some microorganisms. In parallel, synthetic means for obtaining such tetrapyrrolic compounds are recapitulated. The available structural information on chlorophyll catabolites (7) has provided a basis for deriving much of the current insights into the biochemical pathways of chlorophyll breakdown in plants and for complementary plant-biological work, as has been reviewed elsewhere recently (see Scheme 1) (2, 3, 4, 5, 6). 

Scheme 1. Overview of chlorophyll breakdown in senescent higher plants (2). The chlorophylls (Chi a, la (R = CH3) or Chi b, lb (R = CH=0) are degraded via pheophorbide a (Pheo a, 5a), red chlorophyll catabolite (RCC, 11), the primary fluorescent chlorophyll catabolites (pFCCs, 10) to non-fluorescent chlorophyll catabolites (NCCs), such as //v-NCC-1 (2, also called RP-14)...

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