Two independent biochemical pathways for isopentenyl diphosphate and isoprenoid biosynthesis in higher plants

In the early times of isoprenoid research, a single pathway was found for the formation of the C₅ monomer, isopentenyl diphosphate (IPP), and this acetate/mevalonate pathway was supposed to occur ubiquitously in all living organisms. Now, 40 years later, a totally different IPP biosynthesis route has been detected in eubacteria, green algae and higher plants. In this new pathway glyceraldehyde 3-phosphate (GAP) and pyruvate are precursors of isopentenyl diphosphate, but not acetyl-CoA and mevalonic acid. In green tissues of three higher plants it was shown that all chloroplastbound isoprenoids (β-carotene, phytyl chains of chlorophylls and nona-prenyl chain of plastoquinone-9) are formed via the GAP/pyruvate pathway, whereas the cytoplasmic sterols are formed via the acetate/mevalonate pathway. Also, isoprene, emitted by various plants at high light conditions by action of the plastid-bound isoprene synthase, is formed via the new GAP/pyruvate pathway. Thus, in higher plants, there exist two separate and biochemically different IPP biosynthesis pathways: (1) the novel alternative GAP/pyruvate pathway apparently bound to the plastidic compartment and (2) the classical cytoplasmic acetate/mevalonate pathway. This new GAP/pyruvate pathway for IPP formation allows a reasonable interpretation of previous odd results concerning the biosynthesis of chloroplast isoprenoids, which, so far, had mainly been interpreted assuming compartmentation differences. The novel GAP/pyruvate pathway for IPP formation in plastids appears as a heritage of their prokaryotic, endosymbiotic ancestors.     

A PHYTOL-SUBSTITUTED CHLOROPHYLL C FROM EMILIANIA HUXLEYI (PRYMNESIOPHYCEAE)1

A nonpolar chlorophyll c-like pigment was isolated by semi-preparative high performance liquid chromatography from the coccolithophorid Emiliania huxleyi (Lohm.) Hay and Mohler. The visible absorption spectrum of this pigment was similar to that of chlorophyll c₂. However, its nonpolar chromatographic properties were quite different from those of the relatively polar chlorophylls c₂ and c₃ in E. huxleyi and similar to those of chlorophyll a. Analyses by gas chromatography and gas chromatography-mass spectrometry showed that the nonpolar character of this new chlorophyll c was due to the presence of phytol, most likely on the acid side chain of the porphyrin macro-cycle. This is the first example of a phytol-substituted chlorophyll c-like pigment.     

Changes in the Pools of Carotenoids and Protochlorophyll(ide) in Etiolated Cucumber (Cucumis Sativus) Cotyledons Treated with Norflurazon and KC 6361

Changes in the pools of carotenoids and protochlorophyll(ide) were investigated in etiolated cucumber cotyledons treated with norflurazon (NF) and an experimental herbicide KC 6361 (KC). Both the NF- and the KC-treated tissues considerably accumulated the colourless carotenes phytoene and phytofluene with a concomitant depletion of the coloured carotenoids lutein and β-carotene in darkness. However, the profiles of changes in chlorophylls (Chls) and carotenoids were different for the two herbicides. The plants were also influenced by the photosynthetic photon flux densities (PPFD's), with a more pronounced decline of Chl under high PPFD than under low PPFD. The ratios of protochlorophyll (PChl)/protochlorophyllide (PChlide) were greatly altered due to a decrease and an increase of PChl in the NF- and the KC-treated etiolated tissues, respectively, whereas the PChlide content was not significantly influenced by the inhibitors. Large increase of PChls in the KC-treated tissues seems to derive from the binding of accumulated geranylgeraniol (GG) equivalents, through carotenogenic inhibition, to PChlide. Therefore, the alterations of PChl and PChlide occurring under disturbed carotenogenesis may suggest an interaction between the biosynthetic pathways of Chls and carotenoids. In addition, the great proportion of PChl GG and PChl dihydro-GG in the KC-treated tissues implies that PChl formation is regulated at the level of hydrogenation. This revised version was published online in June 2006 with corrections to the Cover Date.     

Interactions of chlorophyll a and terpenoid alcohols with chloroplast acyl lipids in monomolecular films

Surface pressure-area measurements of purified chlorophyll a and monogalactosyl diacylglycerol in mixed monolayers were performed at 20°C with an automatic recording surface film balance at a constant compression rate. In addition structural parts of the chlorophyll and the monogalactosyl diacylglycerol as phytol and geranylgeraniol on one hand and different fatty acids on the other were studied pure and in mixed films. All components studied formed stable monomolecular films. Chlorophyll a and monogalactosyl diacylglycerol showed miscibility. Phytol was immiscible with synthetized monogalactosyl diacylglycerol containing only stearic acid. Mixed monolayers of phytol and monogalactosyl diacylglycerol isolated from barley containing 83 mol % a-linolenic acid showed a strong interaction. An increased miscibility and association were found between phytol and fatty acids with increasing unsaturation. The results are discussed as a model for the localization of part of chlorophyll a in the thylakoid membrane.     

Characterization of protochlorophyllide and protochlorophyllide esters in roots of dark-grown plants

The protochlorophyll pools of roots of dark-grown wheat ( Triticum aestivum L. cv. Walde), maize ( Zea mays L. cv. Goldcrest) and wrinkledseeded pea ( Pisum sativum L. ssp. sativurh cv. Kelvedon Wonder) were investigated by high performance liquid chromatography (HPLC) and low temperature fluorescence spectroscopy. All roots contained protochlorophyllide and esterified protochlorophyllides (protochlorophylls) but with considerably larger relative amounts of the latter compared with etiolated leaves. The alcohol moieties of the 4 detected protochlorophylls were geranylgeraniol (GG), dihydrogeranylgeraniol (DHGG), tetrahydrogeranylgeraniol (THGG) and phytol. The relative amounts of the different protochlorophylls varied between the species. Protochlorophyllide and the 4 protochlorophylls all contained monovinyl forms. The divinyl forms could not be detected by our instruments. Wrinkledseeded pea contained in addition chlorophyll a , some unidentified chlorophylls and negligible amounts of chlorophyllide. Small amounts of carotenoids were found in roots of all investigated species. The carotenoids were the same as those found in green or etiolated leaves, but present in different relative amounts.     

Chemical Profile and Phytotoxic Action of Hibiscus trionum Essential Oil

The chemical profile and phytotoxic action of Hibiscus trionum essential oil (EO) was studied. In total 17 compounds were identified via GC/MS, representing 94.18 % of the entire oil, with phytol (40.37 %) being the dominant constituent. Bioassay revealed that the EO inhibited root elongation of Medicago sativa and Amaranthus retroflexus by 32.66 % and 61.86 % at 5 mg/mL, respectively; meanwhile, the major component phytol also exhibited significant phytotoxic activity, suppressing radical elongation of Pennisetum alopecuroides, M. sativa and A. retroflexus by 26.08 %, 27.55 % and 43.96 % at 1 mg/mL, respectively. The fact that the EO showed weaker activity than phytol implied that some constituents might trigger antagonistic action to decrease the oil's activity. Our study is the first on the chemical profile and phytotoxic effect of H. trionum EO.     

Proximate effects of maternal oviposition preferences on defence efficacy and larval survival in a diet‐specialised tortoise beetle. Who knows best: mothers or their progeny?

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Phytol as one of the determinants of chlorophyll interactions in solution

Optical absorption and fluorescence parameters of chlorophyll a and the phytol-free chlorophyllide a, as well as of their Mg-depleted derivatives, were compared in a series of organic solvents. In contrast to prevailing opinion, the spectral properties of chlorophyll are not indifferent to the removal of phytol. The electronic absorption spectra of chlorophyll a and chlorophyllide a differ and display a different dependence on the nature of the solvent, which cannot be explained solely by the location of a charged carboxylic group in the proximity of the π– electron system. In fact, measurements in media of varying basicity show that deprotonation of the free carboxylic group in chlorophyllide, i.e., the presence of a negative point charge near the macrocycle, has no effect on pigment absorption spectra. Analysis of the solvent effect on the Q_Y energies in terms of solvent polarity reveals that the phytyl moiety perturbs the spectral features of chlorophyll, mainly due to its interactions with the pigment solvation shell. The phytyl residue might also be thus partly involved in controlling the central metal ligation in chlorophylls. This influence of phytol on the spectral features of chlorophyll should be taken into account when comparing the spectra in solution with various spectral forms of chlorophyll in vivo. This revised version was published online in August 2006 with corrections to the Cover Date.