Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals

Siedlecka, Joanna; Kania, Magdalena; Masnyk, Marek; Cmoch, Piotr; Łozińska, Iwona; Czarnocki, Zbigniew; Skorupińska-Tudek, Karolina; Danikiewicz, Witold; Świeżewska, Ewa

doi:10.1007/s11745-015-4104-y

Cited by 12 publications

(8 citation statements)

References 52 publications

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“…Furthermore, a study showed that short-and long-chain polyisoprenoid alcohols are prone to thermo-oxidation, and it has been speculated that oxidized isoprenoids might be formed in the cells because of chemical processes driven by oxidative agents (e.g., reactive oxygen species) [54]. This hypothesis has recently been substantiated by experimental data indicating the susceptibility of polyisoprenoid alcohols to various oxidizing agents for the first time [55]. Yet, the full mechanisms of dolichol oxidation have to be clarified further.…”

Section: Discussionmentioning

confidence: 97%

Dolichol: A Component of the Cellular Antioxidant Machinery

Cavallini

Sgarbossa

Parentini

et al. 2016

Lipids

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Dolichol, an end product of the mevalonate pathway, has been proposed as a biomarker of aging, but its biological role, not to mention its catabolism, has not been fully understood. UV-B radiation was used to induce oxidative stress in isolated rat hepatocytes by the collagenase method. Effects on dolichol, phospholipid-bound polyunsaturated fatty acids (PL-PUFA) and known lipid soluble antioxidants [coenzyme Q (CoQ) and α-tocopherol] were studied. The increase in oxidative stress was detected by a probe sensitive to reactive oxygen species (ROS). Peroxidation of lipids was assessed by measuring the release of thiobarbituric acid reactive substances (TBARS). Dolichol, CoQ, and α-tocopherol were assessed by high-pressure liquid chromatography (HPLC), PL-PUFA by gas-liquid chromatography (GC). UV-B radiation caused an immediate increase in ROS as well as lipid peroxidation and a simultaneous decrease in the levels of dolichol and lipid soluble antioxidants. Decrease in dolichol paralleled changes in CoQ levels and was smaller to that in α-tocopherol. The addition of mevinolin, a competitive inhibitor of the enzyme 3-hydroxy-3-methylglutaryl CoA reductase (HMG-CoAR), magnified the loss of dolichol and was associated with an increase in TBARS production. Changes in PL-PUFA were minor. These findings highlight that oxidative stress has very early and similar effects on dolichol and lipid soluble antioxidants. Lower levels of dolichol are associated with enhanced peroxidation of lipids, which suggest that dolichol may have a protective role in the antioxidant machinery of cell membranes and perhaps be a key to understanding some adverse effects of statin therapy.

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Section: Discussionmentioning

confidence: 97%

Dolichol: A Component of the Cellular Antioxidant Machinery

Cavallini

Sgarbossa

Parentini

et al. 2016

Lipids

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“…Several terpenic compounds had been previously reported in blueberry fruits, namely linalool, linalool oxide, and α-terpineol, were identified (Beaulieu, Stein-Chisholm, & Boykin, 2014; Du & TA B L E 3 Concentration of major volatile compounds (C) detected and quantified by GC-FID in blueberry wines after alcoholic fermentation by the yeast strain Saccharomyces cerevisiae QA23 in laboratory-scale fermentations (LabSFs) and midscale fermentations (MSFs) or after 16 months in bottle Rouseff, 2014; Farneti et al, 2017). Among these compounds, β-citronellol concentration decreased significantly during aging and is believed to be correlated with the degradation of this compound because it is prone to oxidation by light or hydrogen peroxide (Komaszylo née Siedlecka et al, 2016). The linalool concentration decreased significantly during aging, probably due to chemical phenomena, especially oxidation reactions.…”

Section: Minor Volatilesmentioning

confidence: 99%

“…Additional terpenic compounds such as transcarveol, β-citronellol, and p-1-menthen-9-ol were found in blueberry wines, but these compounds can also originate from the fruit due to its terpenoid composition. Among these compounds, β-citronellol concentration decreased significantly during aging and is believed to be correlated with the degradation of this compound because it is prone to oxidation by light or hydrogen peroxide (Komaszylo née Siedlecka et al, 2016).…”

Section: Minor Volatilesmentioning

confidence: 99%

Production of blueberry wine and volatile characterization of young and bottle‐aging beverages

Mendes‐Ferreira

Coelho

Barbosa

et al. 2019

Food Science & Nutrition

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The aim of this study was the production of blueberry wine and the characterization of the volatile compounds of fermented and aging in bottle products. Multivariate data analysis indicated similarity of volatile compounds released when fermentations were conducted at laboratory‐scale and midscale, with the exception of one replicate creating a distinctive group characterized by low concentrations of acetaldehyde, methanol, 1‐hexanol, and ethyl hexanoate, and the production of polyalcohols such as 2,3‐butanediols. This experiment was the only one where no adjustments of YAN were performed. Some of the major volatile compounds (acetaldehyde, ethyl acetate, 2‐methyl‐1‐butanol, 3‐methyl‐1‐butanol, and 2‐phenylethanol) were found above their perception thresholds. Esters and terpenic compounds were the groups of volatiles expressed the most in blueberry wines, followed by volatile fatty acids, alcohols, and norisoprenoids (3‐hydroxy‐7,8‐dihydro‐β‐ionone, 3‐oxo‐α‐ionol, and 3‐hydroxy‐7,8‐dihydro‐β‐ionol). The wines that experienced bottle‐aging are characterized by high concentrations of ethyl esters, diethyl succinate, ethyl lactate, and diethyl malonate. The results contribute for deeper knowledge of the technological procedure, analytical characteristics, and volatile compounds of blueberry wines, reinforcing the interest in this beverage and opening perspectives for further studies on the production of new blueberry‐based products with differential characteristics that value its nutraceutical and functional properties.

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“…Recently, cis-polyisoprenoids gained special attention due to several breakthroughs in the field including improvements in the analytical techniques for their analysis 17,18 , partial identification of their enzymatic machinery 19 , and the discovery of new biological functions beyond glycosylation 20,21 . Among some of these biological functions are the regulation of the membrane fluidity 21 , stimulation of spore wall formation in yeast 20 , and scavenging free radicals in cell membranes [22][23][24] . Interestingly, in cancer cells 25 and P. falciparum 26 , protein dolichylation occurs as a post-translational event, but functions of such derivatives and enzymes involved in this posttranslational protein lipid modification remain unknown.…”

mentioning

confidence: 99%

Metabolomics profiling reveals new aspects of dolichol biosynthesis inPlasmodium falciparum

Zimbres¹,

Valenciano²,

Merino³

et al. 2019

Preprint

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The cis-polyisoprenoid lipids namely polyprenols, dolichols and their derivatives are linear polymers of several isoprene units. In eukaryotes, polyprenols and dolichols are synthesized as a mixture of four or more homologues of different length with one or two predominant species with sizes varying among organisms. Polyprenols have been hardly detectable in eukaryotic cells under normal conditions with the exception of plants and sporulating yeast. Our metabolomics studies revealed that cis-polyisoprenoids are more prevalent and diverse in the parasite Plasmodium falciparum than previously postulated as we uncovered active de novo biosynthesis and substantial levels of accumulation of polyprenols and dolichols of 15 to 19 isoprene units. A distinctive polyprenol and dolichol profile both within the intraerythrocytic asexual cycle and between asexual and gametocyte stages was also observed suggesting that cis-polyisoprenoid biosynthesis changes throughout parasite's development. In addition, we confirmed the presence of an active cisprenyltransferase (PfCPT) and that dolichol biosynthesis occurs via reduction of the polyprenol to dolichol by an active polyprenol reductase (PfPPRD) in the malaria parasite. Isotopic labeling and metabolomic analyses of a conditional mutant of PfCPT or PfPPRD suggest that polyprenols may be able to substitute dolichols in their biological functions when dolichol synthesis is impaired in Plasmodium.Malaria is caused by protozoan parasites of the genus Plasmodium and most cases of lifethreatening malaria are attributable to infection with Plasmodium falciparum. The parasite has a complex life cycle that involves the human host and its vector, the Anopheles mosquitoes. All clinical features are caused during the asexual intraerythrocytic life cycle due to the repeated invasion of human red blood cells (RBCs). The asexual intraerythrocytic developmental cycle of P. falciparum lasts around 48 h, during which the parasite progresses through four morphologically different stages: ring, trophozoite, and schizont stages, ending with rupture of the erythrocyte and release of merozoites that will invade new erythrocytes. Transmission of the malaria parasite requires development of male and female gametocytes (gametocytogenesis), which are ingested by female mosquitoes during a blood meal and undergo sexual reproduction in the mosquito's midgut. Nondividing P. falciparum gametocytes take between 10 and 12 2 days to fully mature and progress through five morphologically distinct forms (stages I to V), which are different from other Plasmodium species.During their complex life cycle malaria parasites encounter different nutritional environments within and between hosts. The presence of de novo and salvage pathways gives parasites a great metabolic flexibility to cope with those changes 1,2 . For example, mature RBCs are capable of only a few metabolic functions since transcription and translation is not present in these cells. However, a wide variety of metabolites are available to the parasite i...

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Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals

Cited by 12 publications

References 52 publications

Dolichol: A Component of the Cellular Antioxidant Machinery

Dolichol: A Component of the Cellular Antioxidant Machinery

Production of blueberry wine and volatile characterization of young and bottle‐aging beverages

Metabolomics profiling reveals new aspects of dolichol biosynthesis inPlasmodium falciparum

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