chlorophyll-a and chlorophyllide-a

Chlorophyllides can be found in photosynthetic organisms. Generally, chlorophyllides have

Topics: Anti-Infective Agents; Antineoplastic Agents, Phytogenic; Antiviral Agents; Biosensing Techniques; Chemistry, Pharmaceutical; Chlorophyll; Chlorophyllides; Electrochemical Techniques; Food Additives; Humans; Light; Molecular Structure; Photosynthesis; Plants; Protochlorophyllide

Chlorophyll a (Chla) and chlorophyllyde a (Chlida) - a derivative of Chla, have been incorporated in the lipid bilayers of two types of liposomes, small unilamellar vesicles (SUV) and multilamelar vesicles (MLV). The objective of the present work was to compare the spectral behaviour of Chla and Chlida incorporated in the lipid bilayers and their sensing behaviour at molecular level. The VIS absorption and fluorescence emission presented differences depending on the type of liposomes and inserted pigment, reflecting the different localization of porphyrin macrocycle in the lipid moieties. The temperature dependence of emission anisotropy and fluorescence intensity, for both Chla and Chlida incorporated in DPPC SUV, revealed the presence of different lipid phases. The degree of incorporation of quercetin (QCT) in liposome membrane was studied by using Chla and Chlida as molecular sensors. The fluorescence polarisation data and the fluorescence quenching process provided arguments for the insertion of the QCT at the interface lipid/water, in the vicinity of lipid polar heads and porphyrin macrocycle. The phytyl chain of Chla penetrating in the hydrophobic core of the lipid bilayers is responsible for the observed differences among Chla and Chlida in sensing the lipid phase transition and the fluorescence quenching process induced by QCT.

Topics: Absorption; Chlorophyll; Chlorophyll A; Chlorophyllides; Lipid Bilayers; Liposomes; Porphyrins; Spectrometry, Fluorescence; Unilamellar Liposomes

Pheophytinization of chlorophyll (Chl) c1, which was isolated from the diatom Chaetoceros gracilis, was kinetically analyzed under weakly acidic conditions, and was compared with that of protochlorophyllide (PChlide) a and chlorophyllide (Chlide) a. Chl c1 possessing a trans-acrylic acid residue at the 17-position exhibited slower pheophytinization kinetics than PChlide a and Chlide a, both of which possessed a propionic acid residue at the same position. The difference in pheophytinization properties between Chl c1 and (P)Chlide a was ascribable to the electronegativity of the 17-substituent in Chl c1 larger than that of (P)Chlide a due to the C17(1)-C17(2) double bond with the conjugated 17(2)-carboxy group in Chl c1. Demetalation kinetics of PChlide a was slower than that of Chlide a, which originated from the effect of the π-macrocyclic structures.

Topics: Acrylates; Chlorophyll; Chlorophyllides; Diatoms; Isomerism; Kinetics; Protochlorophyllide

The inhibitory effects of four chlorophyll derivatives (chlorophyllide [Chlide] a and b and pheophorbide [Pho] a and b) on aflatoxin B1 (AFB1)-DNA adduct formation, and on the modulation of hepatic glutathione S-transferase (GST) were evaluated in murine hepatoma (Hepa-1) cells. Enzyme-linked immunosorbent assay showed that pretreatment with Chlide or Pho significantly reduced the formation of AFB1-DNA adducts, and that Pho was the most potent inhibitor. However, wash-out prior to adding AFB1 totally eliminated inhibition by Childe and partially eliminated inhibition by Pho, indicating that the inhibitory effect of Chlide, and to some extent Pho, was mediated through direct trapping of AFB1. Furthermore, spectrophotometric analysis showed that Pho treatment could increase GST activity in Hepa-1 cells. These observations indicate that the chlorophyll derivatives studied may attenuate AFB1-induced DNA damage in the Hepa-1 cell by direct trapping of AFB1. Pho provided additional protection not only by direct trapping, but also by increasing GST activity against hepatic AFB1 metabolites.

Topics: Aflatoxin B1; Animals; Anticarcinogenic Agents; Cell Line, Tumor; Chlorophyll; Chlorophyllides; DNA Adducts; Glutathione Transferase; Liver Neoplasms, Experimental; Mice

Type C stay-green mutants are defined as being defective in the pathway of chlorophyll breakdown, which involves pheophorbide a oxygenase (PAO), required for loss of green color. By analyzing senescence parameters, such as protein degradation, expression of senescence-associated genes and loss of photosynthetic capacity, we demonstrate that JI2775, the green cotyledon (i) pea line used by Gregor Mendel to establish the law of genetics, is a true type C stay-green mutant. STAY-GREEN (SGR) had earlier been shown to map to the I locus. The defect in JI2775 is due to both reduced expression of SGR and loss of SGR protein function. Regulation of PAO through SGR had been proposed. By determining PAO protein abundance and activity, we show that PAO is unaffected in JI2775. Furthermore we show that pheophorbide a accumulation in the mutant is independent of PAO. When silencing SGR expression in Arabidopsis pao1 mutant, both pheophorbide a accumulation and cell death phenotype, typical features of pao1, are lost. These results confirm that SGR function within the chlorophyll catabolic pathway is independent and upstream of PAO.

Topics: Carbon Dioxide; Cellular Senescence; Chlorophyll; Chlorophyllides; Cloning, Molecular; Cotyledon; DNA Primers; Oxygenases; Pisum sativum; Plant Leaves; Plant Proteins

Chlorophylls (Chl's) are the most abundant natural plant pigments. Four chlorophyll-related compounds (CRCs), including chlorophyllide a and b (Chlide a and b) and pheophorbide a and b (Pho a and b), were investigated for their antioxidative capacities to protect human lymphocyte DNA from hydrogen peroxide (H(2)O(2)) induced strand breaks and oxidative damage ex vivo. Lymphocytes exposed to H(2)O(2) at concentrations of 10 and 50 microM revealed an increased frequency of DNA single-strand breaks (ssb's; as measured by the comet assay) and also an increased level of oxidized nucleoside (as measured by 8-hydroxydeoxyguanosine, 8-OHdG). All Chl's reduced the level of DNA ssb's and 8-OHdG within human lymphocytes following exposure to 10 microM H(2)O(2). Only Pho a and b were able to decrease DNA ssb's and 8-OHdG following treatment of lymphocytes with 50 microM H(2)O(2), in a concentration-dependent fashion. It was demonstrated herein that Pho a and b were more antioxidative than others. We applied DPPH free-radical scavenge assays in vitro, and got similar results. Pho a and b had higher ability in scavenging capacities than others. We conclude that water-extract Chl's are able to enhance the ability of human lymphocytes to resist H(2)O(2)-induced oxidative damage, especially for Pho a and b.

Topics: Antioxidants; Chlorophyll; Chlorophyllides; DNA Damage; Humans; Hydrogen Peroxide; Lymphocytes

The use of HPLC methods to determine and quantify phytoplankton population composition, is sometimes less time-consuming than microscopic identification. However, its general application poses problems since high discrepancies between chlorophyll a calculated using chemotaxonomic methods and direct measurements were noticed. For instance, chemotaxonomic protocols generally employed can lead to a poor estimation of total and relative abundance when high amounts of chlorophyll a breakdown products are present. Therefore, we propose a new approach to calculate relative abundance of algal groups in a phytoplankton population, based on integration of these degradation products in the chemotaxonomic assessment in lentic and shallow freshwater ecosystems.

Topics: Chlorophyll; Chlorophyll A; Chlorophyllides; Chromatography, High Pressure Liquid; Classification; Ecosystem; Eukaryota; France; Fresh Water; Phytoplankton; Seasons

The chemical identification of chlorophyllide (E458F674) (Belanger, F. C., and Rebeiz, C. A. (1980) Plant Sci. Lett. 18, 343-350) has been confirmed by chemical derivatization coupled to spectrofluorometric, spectrophotometric, and chromatographic analysis. Chlorophyllide (E458F674) and its demetallated analog were converted by catalytic hydrogenation into mesochlorophyllide a and mesopheophorbide a. Furthermore, methyl chlorophyllide (E458F674) was converted by partial hydrogenation into a mixture of monovinyl chlorophyllide a isomers and the latter into mesochlorophyllide a by further hydrogenation. On the other hand, chemical oxidation of methyl chlorophyllide (E458F674) converted it into methyl divinyl protochlorophyllide. Chlorophyllide (E458F674) was detected in several plant species and is proposed to be an important intermediate of the chlorophyll a biosynthetic pathway.

Topics: Chemical Phenomena; Chemistry; Chlorophyll; Chlorophyllides; Chloroplasts; Plant Physiological Phenomena; Spectrometry, Fluorescence; Spectrophotometry; Structure-Activity Relationship