Browse
Submit Data
Databases
API
Help

Dataset Information

6 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Phytol derived from chlorophyll hydrolysis in plants is metabolized via phytenal.

ABSTRACT: Phytol is the isoprenoid alcohol bound in ester linkage to chlorophyll, the most abundant photosynthetic pigment in plants. During leaf senescence, large amounts of phytol are released by chlorophyll degradation. However, the pathway of phytol catabolism in plants is unknown. We hypothesized that phytol degradation in plants might involve its oxidation into the long-chain aldehyde phytenal. Using GC-MS for aldehyde quantification after derivatization with methylhydroxylamine, phytenal was identified in leaves, whereas other long-chain aldehydes (phytanal and pristanal) were barely detectable. We found that phytenal accumulates during chlorotic stresses, for example, salt stress, dark-induced senescence, and nitrogen deprivation. The increase in the phytenal content is mediated at least in part independently of enzyme activities, and it is independent of light. Characterization of phytenal accumulation in the pao1 mutant affected in chlorophyll degradation revealed that phytenal is an authentic phytol metabolite derived from chlorophyll breakdown. The increase in phytenal was even stronger in mutants affected in the production of other phytol metabolites including vte5-2 (tocopherol deficient) and pes1 pes2 (fatty acid phytyl ester deficient). Therefore, phytenal accumulation is controlled by competing, alternative pathways of phosphorylation (leading to tocopherol production) or esterification (fatty acid phytyl ester production). As a consequence, the content of phytenal is maintained at low levels, presumably to minimize its toxic effects caused by its highly reactive aldehyde group that can form covalent bonds with and inactivate the amino groups of proteins.

SUBMITTER: Gutbrod P

PROVIDER: S-EPMC8054155 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Catalytic and structural properties of pheophytinase, the phytol esterase involved in chlorophyll breakdown.

Project description:During leaf senescence and fruit ripening, chlorophyll is degraded in a multistep pathway into linear tetrapyrroles called phyllobilins. A key feature of chlorophyll breakdown is the removal of the hydrophobic phytol chain that renders phyllobilins water soluble, an important prerequisite for their ultimate storage in the vacuole of senescent cells. Chlorophyllases had been considered for more than a century to catalyze dephytylation in vivo; however, this was recently refuted. Instead, pheophytinase was discovered as a genuine in vivo phytol hydrolase. While chlorophyllase acts rather unspecifically towards different porphyrin substrates, pheophytinase was shown to specifically dephytylate pheophytin, namely Mg-free chlorophyll. The aim of this work was to elucidate in detail the biochemical and structural properties of pheophytinase. By testing different porphyrin substrates with recombinant pheophytinase from Arabidopsis thaliana we show that pheophytinase has high specificity for the acid moiety of the ester bond, namely the porphyrin ring, while the nature of the alcohol, namely the phytol chain in pheophytin, is irrelevant. In silico modelling of the 3-dimensional structure of pheophytinase and subsequent analysis of site-directed pheophytinase mutant forms allowed the identification of the serine, histidine, and aspartic acid residues that compose the catalytic triad, a classical feature of serine-type hydrolases to which both pheophytinase and chlorophyllase belong. Based on substantial structural differences in the models of Arabidopsis pheophytinase and chlorophyllase 1, we discuss potential differences in the catalytic properties of these two phytol hydrolases.

| S-EPMC5853334 | biostudies-literature

Phytol, a diterpene alcohol from chlorophyll, as a drug against neglected tropical disease Schistosomiasis mansoni.

Project description:BackgroundSchistosomiasis is a major endemic disease that affects hundreds of millions worldwide. Since the treatment and control of this parasitic disease rely on a single drug, praziquantel, it is imperative that new effective drugs are developed. Here, we report that phytol, a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties in vitro and in a mouse model of schistosomiasis mansoni.Methods and findingsIn vitro, phytol reduced the motor activity of worms, caused their death and confocal laser scanning microscopy analysis showed extensive tegumental alterations in a concentration-dependent manner (50 to 100 µg/mL). Additionally, phytol at sublethal doses (25 µg/mL) reduced the number of Schistosoma mansoni eggs. In vivo, a single dose of phytol (40 mg/kg) administered orally to mice infected with adult S. mansoni resulted in total and female worm burden reductions of 51.2% and 70.3%, respectively. Moreover, phytol reduced the number of eggs in faeces (76.6%) and the frequency of immature eggs (oogram pattern) was significantly reduced. The oogram also showed increases in the proportion of dead eggs. Confocal microcopy studies revealed tegumental damage in adult S. mansoni recovered from mice, especially in female worms.ConclusionsThe significant reduction in parasite burden by this chlorophyll molecule validates phytol as a promising drug and offers the potential of a new direction for chemotherapy of human schistosomiasis. Phytol is a common food additive and nonmutagenic, with satisfactory safety. Thus, phytol has potential as a safe and cost-effective addition to antischistosomal therapy.

| S-EPMC3879229 | biostudies-literature

Chlorophyll-Derived Yellow Phyllobilins of Higher Plants as Medium-Responsive Chiral Photoswitches.

Project description:The fall colors are signs of chlorophyll breakdown, the biological process in plants that generates phyllobilins. Most of the abundant natural phyllobilins are colorless, but yellow phyllobilins (phylloxanthobilins) also occur in fall leaves. As shown here, phylloxanthobilins are unique four-stage photoswitches. Which switching mode is turned on is controlled by the molecular environment. In polar media, phylloxanthobilins are monomeric and undergo photoreversible Z/E isomerization, similar to that observed for bilirubin. Unlike bilirubin, however, the phylloxanthobilin Z isomers photodimerize in apolar solvents by regio- and stereospecific thermoreversible [2+2] cycloadditions from self-assembled hydrogen-bonded dimers. X-ray analysis revealed the first stereostructure of a phylloxanthobilin and its hydrogen-bonded self-templating architecture, helping to rationalize its exceptional photoswitch features. The chemical behavior of phylloxanthobilins will play a seminal role in identifying biological roles of phyllobilins.

| S-EPMC5248603 | biostudies-literature

Dynamics and correlations of chlorophyll and phytol content with silage bacterial of different growth heights <i>Pennisetum sinese</i>.

Project description:The dynamics and correlations of chlorophyll and phytol content with silage bacterial of different growth heights Pennisetum sinese were investigated. The results demonstrated that the chlorophyll and phytol content of P. sinese before and after ensiled decreased with the increase of growth height. Ensiling significantly reduced pigment content but had no significant effect on phytol. In addition, P. sinese pigment yield before and after ensiled increased with growth heights increasing, and the yield at 150 or 180 cm was obviously higher. Moreover, the higher silage quality V-Score were at 150 or 180 cm growth heights. Furthermore, the silage microbial diversity were varied by growth heights, and some specific undesirable microorganisms (Acinetobacter, Cellvibrio, Sphingobacterium, etc.) were negatively correlated with pigment and phytol content. Therefore, with comprehensive consideration of pigment, phytol yield, and silage quality, the optimum harvest growth height of P. sinese was 150 cm. Furthermore, precise reduction of particular undesirable microorganisms maybe helps to preserve pigments and phytol.

| S-EPMC9608139 | biostudies-literature

HCAR Is a Limitation Factor for Chlorophyll Cycle and Chlorophyll b Degradation in Chlorophyll-b-Overproducing Plants.

Project description:The chlorophyll (Chl) cycle is the metabolic pathway for Chl a and Chl b inter-conversion. In this pathway, Chl b is synthesized from Chl a by the catalyzing action of chlorophyllide a oxygenase (CAO). In contrast, Chl b is firstly reduced to produce 7-hydroxymethyl Chl (HMChl) a, which is catalyzed by two isozymes of Chl b reductase (CBR), non-yellow coloring 1 (NYC1) and NYC1-like (NOL). Subsequently, HMChl a is reduced to Chl a by HMChl a reductase (HCAR). CAO plays a pivotal role in Chl a/b ratio regulation and plants over-accumulate Chl b in CAO-overexpressing plants. NYC1 is more accumulated in Chl-b-overproducing plants, while HCAR is not changed. To investigate the role of HCAR in Chl cycle regulation, the Chl metabolites of Chl-b-overproducing plants were analyzed. The results showed that HMChl a accumulated in these plants, and it decreased and the Chl a/b ratio increased by overexpressing HCAR, implying HCAR is insufficient for Chl cycle in Chl-b-overproducing plants. Furthermore, during dark-induced senescence, the non-programmed cell death symptoms (leaves dehydrated with green color retained) of Chl-b-overproducing plants were obviously alleviated, and the content of HM pheophorbide (HMPheide) a and Pheide b were sharply decreased by overexpressing HCAR. These results imply that HCAR is also insufficient for Chl degradation in Chl-b-overproducing plants during senescence, thus causing the accumulation of Chl metabolites and non-programmed cell death of leaves. With these results taken together, we conclude that HCAR is not well regulated and it is a limiting factor for Chl cycle and Chl b degradation in Chl-b-overproducing plants.

| S-EPMC7762049 | biostudies-literature

hydrolysis

Project description:hydrolysis Genome sequencing

| PRJNA626402 | ENA

Plants with less chlorophyll: A global change perspective.

Project description:The necessary reduction of greenhouse gas (GHG) emissions may lead in the future to an increase in solar irradiance (solar brightening). Anthropogenic aerosols (and their precursors) that cause solar dimming are in fact often co-emitted with GHGs. While the reduction of GHG emissions is expected to slow down the ongoing increase in the greenhouse effect, an increased surface irradiance due to reduced atmospheric aerosol load might occur in the most populated areas of the earth. Increased irradiance may lead to air warming, favour the occurrence of heatwaves and increase the evaporative demand of the atmosphere. This is why effective and sustainable solar radiation management strategies to reflect more light back to space should be designed, tested and implemented together with GHG emission mitigation. Here we propose that new plants (crops, orchards and forests) with low-chlorophyll (Chl) content may provide a realistic, sustainable and relatively simple solution to increase surface reflectance of large geographical areas via changes in surface albedo. This may finally offset all or part of the expected local solar brightening. While high-Chl content provides substantial competitive advantages to plants growing in their natural environment, new plants with low-Chl content may be successfully used in agriculture and silviculture and be as productive as the green wildtypes (or even more). The most appropriate strategies to obtain highly productive and highly reflective plants are discussed in this paper and their mitigation potential is examined together with the challenges associated with their introduction in agriculture.

| S-EPMC8246939 | biostudies-literature

Synthesis of novel phytol-derived γ-butyrolactones and evaluation of their biological activity.

Project description:The synthesis of phytol-derived γ-butyrolactones as well as their evaluation for deterrent activity towards peach-potato aphid Myzus persicae and antiproliferative activity against four selected cancer cell lines are reported. Products were obtained in good yields (19-96%) and their structures were fully characterized by spectroscopic data (NMR, HRMS). Four synthesized δ-halo-γ-lactones (4-7) are new and have not been previously described in the literature. In the choice test phytol (1) appeared deterrent to M. persicae, whereas modifications of its structure did not cause the avoidance of the treated leaves by the aphids. In contrast, aphids were attracted to the leaves treated with the new trans-δ-chloro-γ-lactone (6). Electrical Penetration Graph (EPG) technique applied to explore the aphid probing and feeding activity revealed that neither phytol nor lactone 6 affected aphid probing and the consumption of phloem sap, which means that both phytol and the lactone 6 might have acted as postingestive modifiers of aphid behavior. The results of in vitro antitumor assays showed that obtained phytol derivatives exhibit cytotoxic activity against studied cancer cell lines (leukemia, lung and colon carcinoma and its doxorubicin resistant subline). Halolactones 4-6 were identified as the compounds, which arrest cell cycle of leukemia cells mainly in G2/M and S phases.

| S-EPMC7896091 | biostudies-literature

Are bryophytes shade plants? Photosynthetic light responses and proportions of chlorophyll a, chlorophyll b and total carotenoids.

Project description:Background and aimsData are presented from 39 species of mosses and 16 liverworts for ratios of chlorophylls and total carotenoids, and light saturation of photosynthetic electron flow or photosynthetic CO2 uptake, in relation to the postulate that bryophyte cells in general show shade-plant characteristics.MethodsPigment concentrations were measured by spectrophotometer in 80 % acetone extracts. Light-saturation curves were constructed by (modulated) chlorophyll florescence and for some species by infra-red gas analysis.Key resultsThe pigment measurements were widely variable but broadly in line with the findings of previous authors. Median values (mosses/liverworts) were: total chlorophyll, 1.64/3.76 mg g(-1); chlorophyll a : b, 2.29/1.99; chlorophylls : carotenoids, 4.74/6.75). The PPFD values at 95 % saturation (estimated from fitted curves) also ranged widely, but were almost all <1000 micromol m(-2) s(-1); the median for mosses was 583 and for liverworts 214 micromol m(-2) s(-1). The two highest PPFD95% values were from Polytrichum species with lamella systems forming a ventilated photosynthetic tissue. Total chlorophyll, chlorophyll a : b and chlorophylls : carotenoids all correlated significantly with PPFD95%.ConclusionsBryophytes include but are not inherently shade plants. Light-saturation levels for species of open sun-exposed habitats are lower than for vascular sun plants and are probably limited by CO2 diffusion into unistratose leaves; this limit can only be exceeded by bryophytes with ventilated photosynthetic tissues which provide increased area for CO2 uptake.

| S-EPMC4242232 | biostudies-literature

Pyrrolic and Dipyrrolic Chlorophyll Degradation Products in Plants and Herbivores.

Project description:The degradation of chlorophyll, the omnipresent green pigment, has been investigated intensively over the last 30 years resulting in many elucidated tetrapyrrolic degradation products. With a comparison to the degradation of the structurally similar heme, we hereby propose a novel additional chlorophyll degradation mechanism to mono- and dipyrrolic products. This is the first proof of the occurrence of a family of mono- and dipyrrols in leaves that are previously only known as heme degradation products. This product family is also found in spit and feces of herbivores with specific metabolomic patterns reflecting the origin of the samples. Based on chromatographic and mass spectrometric evidence as well as on mechanistic considerations we also suggest several tentative new degradation products. One of them, dihydro BOX A, was fully confirmed as a novel natural product by synthesis and comparison of its spectroscopic data.

| S-EPMC7318184 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data