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The growing perspective of running out of crude oil followed by increasing prices for all crude oil-based materials, e.g., crude oil-based polymers, which have a huge number of practical applications but are usually neither biodegradable nor environmentally friendly, has resulted in searching for their substitutes—namely, bio-based polymers. Currently, both these types of polymers are used in practice worldwide. Owing to the advantages and disadvantages occurring among plastics with different origin, in this current review data on selected popular crude oil-based and bio-based polymers has been collected in order to compare their practical applications resulting from their composition, chemical structure, and related physical and chemical properties. The main goal is to compare polymers in pairs, which have the same or similar practical applications, regardless of different origin and composition. It has been proven that many crude oil-based polymers can be effectively replaced by bio-based polymers without significant loss of properties that ensure practical applications. Additionally, biopolymers have higher potential than crude oil-based polymers in many modern applications. It is concluded that the future of polymers will belong to bio-based rather than crude oil-based polymers.

The review aims to summarize the current knowledge on the possibility of using non-conventional yeast species Yarrowia lipolytica in the treatment and upgradation of industry wastes. Importantly Y. lipolytica yeast is argued as generally recognized as safe species, what indicates the high application potential of the reviewed technologies. Special emphasis in the paper was given on microbial processing of the food industry wastes, including fish and animals’ wastes utilization. Yarrowia-based processing of waste cooking oil or oil-bearing plants wastewaters, such as palm oil mill effluents or olive mill wastewater was reviewed. Recent advances in biosynthesis of valuable metabolites (e.g. lipases or microbial oil) with simultaneous wastes utilization by Y. lipolytica are additionally discussed. The broad implications of the present paper are a part of sustainable development policy. Graphic Abstract

Dihydrocaffeic acid (DHCA) is a phenolic acid bearing a catechol ring and three-carbon side chain. Despite its being found in minor amounts in numerous plants and fungi of different origins, it has attracted the interest of various research groups in many fields of science, from food to biomedical applications. The review article presented herein aims to show a wider audience the health benefits and therapeutic, industrial, and nutritional potential of dihydrocaffeic acid, by sheddinglight on its occurrence, biosynthesis, bioavailability, and metabolism. The scientific literature describes at least 70 different derivatives of dihydrocaffeic acid, both those occurring naturally and those obtained via chemical and enzymatic methods. Among the most frequently used enzymes that were applied for the modification of the parent DHCA structure, there are lipases that allow for obtaining esters and phenolidips, tyrosinases used for the formation of the catechol ring, and laccases to functionalize this phenolic acid. In many studies, both in vitro and in vivo, the protective effect of DHCA and its derivatives on cells subjected to oxidative stress and inflammation were acknowledged.

Two biocatalysts with high lipolytic activity were obtained – freeze-dried supernatant and freeze-dried biomass of Yarrowia lipolytica KKP 379. The biocatalysts were compared with Candida antarctic...

Due to the increase in the consumption of highly processed food in developed countries, as well as, a growing number of foodborne diseases, exploration of new food additives is an issue focusing on scientific attention and industrial interest. Functional compounds with lipophilic properties are remarkably desirable due to the high susceptibility to the deterioration of lipid-rich food products. This paper in a comprehensive manner provides the current knowledge about the enzymatic synthesis of lipophilic components that could act as multifunctional food additives. The main goal of enzymatic lipophilization of compounds intentionally added to food is to make these substances soluble in lipids and/or to obtain environmentally friendly surfactants. Moreover, lipase-catalyzed syntheses could result in changes in the antioxidant and antimicrobial activities of phenolic compounds, carbohydrates, amino acids (oligopeptides), and carboxylic acids. The review describes also the implementation of a new trend in green chemistry, where apart from simple and uncomplicated chemical compounds, the modifications of multi-compound mixtures, such as phenolic extracts or essential oils have been carried out. Supplementary Information The online version contains supplementary material available at 10.1007/s11274-021-03200-5.

Food byproduct streams can potentially be transformed into value-added products such as microbial lipids in bioprocesses based on the non-conventional Yarrowia yeast. The effect of culture conditions of Y. lipolytica KKP 379 wild strain in waste media on the efficiency of lipid accumulation, fatty acid composition, presence of selected sterols, yield and elemental composition of biomass has been studied. Batch and fed-batch bioreactor cultures were carried out in media with molasses hydrolysate (MH) and post-frying rapeseed oil. It was determined that biomass grown in MH contained more minerals than in medium with rapeseed post-frying oil. Considering the PDSC study, the Tmax of oxidation induction ranged from 10.04–26.36 min for the analyzed samples. The biomass from fed-batch cultures with MH had the highest total sterol content (68.40 mg/goil), dominated by ergosterol at 60.16 mg/g. Feeding with post-frying rapeseed oil with new doses of mineral medium promoted maintaining the cellular lipid content at a high level (30.75–31.73%) for 50 h, with maximum yield at 37.50%. The results of the experiment showed that the cellular lipid accumulation efficiency of Y. lipolytica yeast and the content of sterols in the cell membrane can be manipulated by selecting waste substrates and culture mode.

Different plant extracts have the potential to be important sources of phenolic compounds. Their antibacterial, antifungal and antioxidant properties are of interest to researchers due to various possibilities for use in the pharmacy, cosmetic and food industries. Unfortunately, the direct application of phenolics in food is limited because of their hydrophilic nature and low solubility. The review is devoted to the recent advances in the methods of lipophilization of phenolic extracts along with the use of enzymes. The concept of extract modification instead of single compound modification is based on the expected synergistic effect of many phenolic compounds. The main focus is on the phenolic compounds found in fruits, flowers and leaves of different common and underutilized as well as medicinal, folk-medicinal or endemic plants. The compiled papers point to the great interest in the modification of anthocyanins, highly active but often unstable phenolics. Some examples of other flavonoids are also outlined. The possible applications of the lipophilized plant extracts are presented for improving the stability of edible oils, decreasing the content of acrylamide, exhibiting higher color stability in thermal processing and increasing the nutritional value.

The aim of the study was to compare the effect of the substituent and its position in the aromatic ring on the antioxidant activity of hexanoic acid esters obtained in reactions catalyzed by immobilized lipase B from Candida antarctica. 4-Hydroxybenzyl hexanoate, 2-hydroxybenzyl hexanoate, 4-methoxybenzyl hexanoate, and vanillyl hexanoate were obtained with conversion yields of 50 to 80%. The antioxidant activity of synthesized esters, their alcohol precursors and BHT (Butylated HydroxyToluene) was compared with DPPH (2,2-diphenyl-1-picrylhydrazyl), CUPRAC (cupric ion reducing antioxidant capacity), and CBA (crocin bleaching assay) methods. Furthermore, it was investigated whether the presence of vanillyl hexanoate in a concentration of 0.01 and 0.1% affected the oxidative stability of sunflower and rapeseed oils in the Rancimat test. It was observed that the antioxidant activity of hexanoic acid esters depends on the presence and position of the hydroxyl group in the aromatic ring. The highest activities were found for vanillyl alcohol, vanillyl hexanoate, and BHT. The addition of the ester and BHT significantly extended the induction times of the tested oils, and these compounds exhibited similar activity. Vanillyl hexanoate increased the induction time from 4.49 to 5.28 h and from 2.73 to 3.12 h in the case of rapeseed and sunflower oils, respectively.

The aim of the study was to evaluate the possibility to utilize a fish waste oil issued from the industrial smoking process in nitrogen-limited Yarrowia lipolytica yeast batch cultures. The waste carbon source was utilized by the yeast and stimulated the single cell oil production via an ex novo pathway. The yeast biomass contained lipids up to 0.227 g/gd.m.. Independently from culture conditions, high contents of very long chain fatty acids were quantified in yeast biomass including docosahexaenoic (DHA), eicosapentaenoic acid (EPA), eicosenic and erucic acids. The pH regulation did not influence the cellular lipids yield (0.234 g/gd.m.). Meanwhile, the intensification of the oxygenation of medium by changing the mixing speed (maximum concentration of lipids produced 4.64 g/dm3) and decreasing the amount of inoculum had a positive effect on the culture parameters in waste fish oil medium. Further work on upgradation of the original waste is advisable, especially because the oil indicated high content of polyphenols and lower susceptibility to oxidation than microbial oil derived from control olive oil medium.

Microbial oils, also called single-cell oils, are lipids synthesized by microorganisms exceeding 20% of the dry weight of the cell. The aim of this work was to investigate the possibility of applying a rapeseed post-frying oil from fish fillets as a carbon source in growth medium for Yarrowia lipolytica oleaginous yeast species in order to synthesize a microbial oil. The key contribution of this work is that the solution provides a sustainable method for valorization of post-frying waste oil. Shaken batch cultures were provided and the influence of triacylglyceride hydrolysis on yeast growth was evaluated. In conclusion, post-frying rapeseed oil seems to be an easily utilizable carbon source by yeast. Regardless of the method of lipid substrate pretreatment, the yeast strain preferentially accumulated oleic acid (C18: 1) from 52.07% to 66.62% and linoleic acid (C18: 2) from 12.98% to 24.10%. To the best of our knowledge, this is the first report of using the oxygen nanobubbles as an unconventional method of aerating the culture medium containing lipid carbon sources. The use of water oxygenated with nano-sized bubbles to prepare culture media resulted in obtaining a higher yield of biomass compared to the biomass yield in distilled water-based medium.

Listeria monocytogenes—A Gram-positive intracellular bacteria is one of the most virulent foodborne pathogens. A common strategy used to control the growth of bacteria in food is using food additives. However, many bacterial species are resistant to food preservatives, and bacterial resistance can be natural or acquired. Therefore, there is a constant need to search for new compounds with antimicrobial properties. The purpose of the present study was to evaluate the efficiency of five (ethyl, butyl, hexyl, octyl, and decyl) esters of 4-hydroxyphenylpropanoic acid against L. monocytogenes PCM 2191. Esters were obtained in reactions catalyzed by Candida antarctica lipase B. Purified esters with structures confirmed by 1H NMR were applied to determine minimal inhibitory concentrations (MIC) using the microdilution broth method. MIC values ranged 0.0625–16 mM. The results of this study have demonstrated the potential application of 4-hydroxyphenylpropanoic acid alkyl esters in inhibiting the growth of L. monocytogenes. Octyl 4-hydroxyphenylpropanoate proved to be the best antimicrobial agent and was used in a time-kill assay with different concentrations of 1 × MIC, 4 × MIC, and 16 × MIC. Three to nine log reduction of cell number were observed compared to control medium without any antimicrobial compound after 24 h, and the possibility of using octyl 4-hydroxyphenylpropanoate in food applications is worth further investigation.

Increase in energy demand and limited sources of fossil fuels force the world’s population to seek new energy sources Biodiesel obtained by transesterification of oils with an alcohol in the presence of catalysts is an example of renewable fuel. The aim of the study was to assess the best conditions for enzymatic biodiesel synthesis by direct transesterification of rapeseed cake using Taguchi method. The influence of alcohol (methanol, ethanol, propanol, and butanol), temperature (30–60 °C), C. antarctica lipase B concentration (0.5–2 %), time (6–48 h) and rapeseed cake to alcohol ratio (1:2–1:5) was examined in the synthesis of fatty acid alkyl esters. Optimum conditions for direct enzymatic transesterification of rapeseed cake are: 30 °C, 12 h, 0.5 % of lipase and ethanol in 4:1 ratio to rapeseed cake.

Waste management solutions including the valorization of waste materials in biotechnological processes is an important issue needing to be explored. A significant amount of waste is being generated by the food industry. In this study, an attempt was made to utilize two fish industry wastes simultaneously—waste brine and post-frying oil from frying fish fillets in Yarrowia lipolytica culture with high single cell oil synthesis yield. Oxygenation in the culture medium had a positive effect on the biosynthesis efficiency of microbial oil, resulting in the highest content of lipids in yeast cells at the level of 0.431 g/g d.m (dry mass). Y. lipolytica yeast preferentially accumulated oleic acid and linoleic acid, and the high content of linolenic acid, valuable from a nutritional point of view, was also found in microbial oil. This study proved that the use of post-frying rapeseed oil gives a chance to obtain valuable storage lipids in Y. lipolytica yeast cells via ex novo biosynthesis pathway. Furthermore, the wastewater stream could be limited using a waste brine as a solvent in medium preparation, but the brine share should not exceed 30% so as not to inhibit yeast cell growth.

Yarrowia lipolytica yeast is a model species of the group of oleaginous microorganisms capable of intracellular lipids accumulation in an amount exceeding 20% of the dry mass. Single cell oil biosynthesis can follow one of two biochemical pathways—de novo accumulation of cellular lipids in medium containing non-lipid carbon sources (including saccharides, glycerol) and ex novo microbial oil synthesis which involves fatty acids uptake from the environment. The mRNA expression of selected genes of de novo and ex novo lipid synthesis pathways was analyzed and correlated with the phenotypically observed features. It was proved that the accumulation yield of storage lipids via ex novo pathway was to some extent dependent on the limitation of the nitrogen source in the medium. It was also proposed that the synthesis of intracellular lipids in lipid-rich medium proceeded mainly via ex novo pathway, although the activity of genes encoding the enzymes of the de novo pathway were not completely inhibited at the stage of transcription by fatty acids present in the medium (e.g., ATP-citrate lyase). Molecular markers of two biosynthesis routes has been outlined and a hypothetical connection point between de novo and ex novo route were indicated.

Celem niniejszej pracy była charakterystyka mięsa ryb oraz odpadów przemysłu rybnego jako źródła cennych składników odżywczych oraz surowca dla przemysłu energetycznego. Mięso ryb i przetwory rybne są ważnym elementem zróżnicowanej diety. Ryby i odpady rybne mogą być źródłem wielonienasyconych kwasów tłuszczowych omega-3 – kwasu dokozaheksaenowego (DHA) i eikozapentaenowego (EPA), czyli związków wywierających pozytywny wpływ na organizm człowieka. W technologii żywności stosuje się dodatki funkcjonalne pochodzące z ryb, w tym żelatynę rybną różniącą się właściwościami fizykochemicznymi od żelatyny wieprzowej, a także witaminy rozpuszczalne w tłuszczach oraz barwniki karotenoidowe o działaniu przeciwutleniającym. Z ryb mogą być także izolowane peptydy wykazujące przeciwdrobnoustrojowe oddziaływanie na różne gatunki bakterii Gram-dodatnich i Gram-ujemnych. W pracy wskazano również na możliwość wykorzystania poprodukcyjnych odpadów rybnych do pozyskiwania składników cennych pod względem żywieniowym. Oprócz wykorzystania odpadów rybnych do produkcji pasz i mączek rybnych, olejów oraz kiszonek, jak również hydrolizatów białkowych jako przypraw w kuchni azjatyckiej, możliwe jest ich wykorzystanie w przemyśle energetycznym, m.in. do produkcji paliwa ciekłego typu biodiesel lub do produkcji biogazu. W pracy omówiono także aspekt bezpieczeństwa spożywania mięsa ryb, które mogą zawierać szkodliwe lipofilowe związki organiczne oraz metale ciężkie kumulowane przez te zwierzęta w środowisku bytowania, czyli w zanieczyszczonych słodkich i słonych wodach.

Microbial lipids called a sustainable alternative to traditional vegetable oils invariably capture the attention of researchers. In this study, the effect of limiting inorganic phosphorus (KH2PO4) and nitrogen ((NH4)2SO4) sources in lipid-rich culture medium on the efficiency of cellular lipid biosynthesis by Y. lipolytica yeast has been investigated. In batch cultures, the carbon source was rapeseed waste post-frying oil (50 g/dm3). A significant relationship between the concentration of KH2PO4 and the amount of lipids accumulated has been revealed. In the shake-flask cultures, storage lipid yield was correlated with lower doses of phosphorus source in the medium. In bioreactor culture in mineral medium with (g/dm3) 3.0 KH2PO4 and 3.0 (NH4)2SO4, the cellular lipid yield was 47.5% (w/w). Simultaneous limitation of both phosphorus and nitrogen sources promoted lipid accumulation in cells, but at the same time created unfavorable conditions for biomass growth (0.78 gd.m./dm3). Increased phosphorus availability with limited cellular access to nitrogen resulted in higher biomass yields (7.45 gd.m./dm3) than phosphorus limitation in a nitrogen-rich medium (4.56 gd.m./dm3), with comparable lipid yields (30% and 32%). Regardless of the medium composition, the yeast preferentially accumulated oleic and linoleic acids as well as linolenic acid up to 8.89%. Further, it is crucial to determine the correlation between N/P molar ratios, biomass growth and efficient lipid accumulation. In particular, considering the contribution of phosphorus as a component of coenzymes in many metabolic pathways, including lipid biosynthesis and respiration processes, its importance as a factor in the cultivation of the oleaginous microorganisms was highlighted.

Drożdże Yarrowia lipolytica to modelowy gatunek mikroorganizmów olejogennych, zdolny do kumulacji lipidów wewnątrz komórki w ilości powyżej 20 % suchej masy. Oprócz prac nad zwiększaniem wydajności biosyntezy oleju mikrobiologicznego ważnym zagadnieniem jest także dobór warunków ekstrakcji tłuszczu z biomasy drożdży. Celem pracy była ocena wpływu wybranych parametrów (rodzaju rozpuszczalnika, sposobu przygotowania próbki oraz czasu trwania procesu) na wydajność ekstrakcji tłuszczu zawartego w komórkach dzikiego szczepu drożdży Y. lipolytica KKP 379, prowadzonej w aparacie Soxhleta oraz na skład kwasów tłuszczowych w uzyskanym oleju. Hodowle okresowe drożdży prowadzono w bioreaktorze laboratoryjnym w bogatym podłożu YPO oraz w podłożach mineralnych z limitowaną zawartością azotu, co umożliwiło otrzymanie biomasy komórkowej o zróżnicowanej zawartości oleju mikrobiologicznego. W badaniach zastosowano plany kwadratów łacińskich, co pozwoliło na odmaskowanie efektu wpływu sposobu przygotowania próbki na zmienną zależną, jaką była zawartość tłuszczu w biomasie drożdży. Najlepsze rezultaty osiągnięto po przygotowaniu biomasy metodą lityczną z wykorzystaniem komercyjnego preparatu Y-PER. Zastosowany czas ekstrakcji oraz rodzaj rozpuszczalnika (eter naftowy lub heksan) nie wpłynęły istotnie na wydajność procesu. Rodzaj rozpuszczalnika miał z kolei wpływ na zawartość trzech kwasów tłuszczowych spośród czternastu zidentyfikowanych w lipidach ekstrahowanych z biomasy drożdży, tj. kwasu palmitooleinowego, eikozapentaenowego i dokozatetraenowego. Większą zawartość wymienionych kwasów oznaczono w próbkach ekstrahowanych heksanem.

Multidrug efflux pumps play an important role in antibiotic resistance in bacteria. In Pseudomonas aeruginosa, the MexXY pump provides intrinsic resistance to many antimicrobials, including aminoglycosides. The expression of the mexXY operon is negatively regulated by the MexZ repressor. This repression is alleviated in response to antibiotic-induced ribosome stress, which results in increased synthesis of the antirepressor ArmZ, interacting with MexZ. The molecular mechanism of MexZ inactivation by ArmZ is not known. Here, we show that the N-terminal part of MexZ, encompassing the DNA-binding domain, is required for the interaction with ArmZ. Using bacterial two-hybrid system-based mutant screening and pulldown analyses, we identified substitutions in MexZ that diminished (R3S, K6E, and R13H) or completely impaired (K53E) the interaction with ArmZ without blocking MexZ activity as a transcriptional repressor. The introduction of the corresponding mexZ missense mutations into the P. aeruginosa PAO1161 chromosome impaired (mexZK6E and mexZR13H) or blocked (mexZK53E) tetracycline-mediated induction of mexY expression. Concomitantly, the PAO1161 mexZK53E strain was more susceptible to aminoglycosides. The identified residues are highly conserved in MexZ-like transcriptional regulators found in bacterial genomes encoding both MexX/MexY/MexZ and ArmZ/PA5470 orthologs, suggesting that a similar mechanism may contribute to the induction of efflux-mediated resistance in other bacterial species. Overall, our data shed light on the molecular mechanism of ArmZ-mediated induction of intrinsic antimicrobial resistance in P. aeruginosa.

Lipases are a group of enzymes of considerable significance in organic synthesis, among which Candida antarctica lipase B (CALB) is one of the most widely studied enzymes. The activity of the biocatalyst has been intensively characterized in many organic media, but this paper aimed to compare the effect of 20 different solvents on the activity of CALB in the hydrolysis of p-nitrophenyl laurate. Nonpolar, polar aprotic, and polar protic solvents were used for enzyme pretreatment and then entered the composition of mixed solvents reaction medium. An impact of solvents on solvation processes affecting the catalysis steps, protein denaturation, and changes of its conformation was discussed. Moreover the hydrolytic activity of CALB with partition coefficient (logP) of the solvent used was correlated. It was emphasized that the substrate solubility plays an important role in solvent selection. In the presence of hydrophobic solvents, hydration layer becomes more hydrophobic facilitating the substrate access to the enzyme surface. In turn, polar compounds are good solvents for organic substrates facilitating the penetration of the aqueous layer that surrounds the surface of the enzyme. Two variants proved to be favorable for ester hydrolysis reaction: isooctane or polar solvent such as acetone, tert -butyl methyl ether, tert-butanol or acetonitrile.

Single cell oil (SCO) is the lipid accumulated in the cells of oleaginous microorganisms. Cellular lipids can be synthesized in two different pathways: de novo by metabolizing hydrophilic substrates and ex novo by fermenting hydrophobic substrates. The aim of the study was to evaluate the effect of carbon source (glucose and olive oil) in the culture medium on the course of microbial oil accumulation in Y. lipolytica cells. The level of selected gene expression by real time quantitative PCR method was investigated. The significant increase in expression of the POX2 gene encoding acyl-CoA oxidase II, which preferentially oxidizes long-chain acyl-CoAs formed from substrate fatty acids incorporated inside the microbial cell, was observed in medium with olive oil in relation to glucose containing medium. Noteworthily, the presence of lipid carbon substrate did not inhibit the level of ACL gene transcription coding for ATP-citrate lyase, the key enzyme of the lipid de novo accumulation process. The present study indicated that de novo lipid biosynthesis could occur despite the presence of fatty acids in the medium, and the synthesis of storage lipids in the presence of lipid carbon substrates could be carried out with the use of both pathways (de novo and ex novo).

Phenolic acids are secondary plant metabolites belonging to polyphenol classes, widely spread throughout the plant kingdom. The name "phenolic acids", in general, describes phenols that possess one carboxylic acid functionality and they could be divided into three major subclasses: hydroxybenzoic, hydroxycinnamic and hydroxyphenylacetic acids. The great interest in phenolic acids is associated with their high potential for food preservation (antioxidant and antimicrobial activity) and, last but not least, high therapeutic potential. The aim of this review is to summarise the current knowledge concerning phenolic acids and the topics discussed include natural sources of phenolic acids, biosynthesis and metabolism, health benefits of phenolic acids (first of all the antioxidant activity of dietary phenolics and also anticarcinogenic and anti-inflammatory effect), their antimicrobial activity for selected groups of bacteria and fungi (yeasts) and structural modifications of the molecule especially those increasing lipophilicity and improving solubility in lipids. Recent advances in the methods of enzymatic synthesis of phenolic acid derivatives are described and some conclusions referring to Structure-Property-Activity Relationships of phenolic acids, particularly important from the point of view of their pharmaceutical and nutritional applications, are discussed.