Predominant Isomer Research Articles

One-pot synthesis of stable vitamin C analogue using trans-glycosylating enzyme from Aspergillus carbonarius BTCF 5

Biocatalysis using transglycosidases for one-pot glycosylation of small molecules is a greener alternative to chemical glycosylation. The transglycosylation potential of the crude culture filtrate of Aspergillus carbonarius BTCF 5 was evaluated based on the biotransformation of the target molecule, ascorbic acid (Vitamin-C), to its more stable glycosylated analogue -2-O-α-D-glucopyranosyl ascorbic acid (AA2G), using maltose as the glycosyl donor. Media engineering increased the transglycosylation yield by 64%, whereas the use of concentrated culture filtrate increased the transglycosylation yield by 70%. Protein purification studies identified the candidate transglycosylating enzyme to be a GH 31 family CAZyme (α-transglucosidase). A minimally purified enzyme could enhance the transglycosylation yield by 77% with a total AA2G yield of 91.5 mM (10.32 g/L) and improved the overall conversion rate of ascorbic acid and maltose in the reaction by 16% and 6.3% respectively from the base level. A two-step column chromatography helped in product purification with 46% recovery. The structural characterization of purified AA2G provided a detailed insight into the regioselectivity of the enzyme to glycosylate C2 of ascorbic acid and its ability to form AA2G as the predominant isomer, which is also the most preferred one for end applications.

Reaction of Isatin and 2-Chloropyridinium Salt: An Efficient and Diastereoselective Synthesis of α,β-Unsaturated Oxindoles.

A new, mild, and diastereoselective method has been developed for the synthesis of β-pyridone-α,β-unsaturated oxindoles by the reaction of isatins and 2-chloropyridinium salts in EtOH at room temperature for 5 min. This method operates under mild reaction conditions, providing the product with a good yield and diastereoselectivity, and it exhibits excellent tolerance toward various functional groups. The predominant isomer is the Z isomer, which can convert to the E isomer in the presence of NaN3.

Chemically Separable Co(II) Spin-State Isomers.

The phenomenon of spin crossover involves coordination complexes with switchable spin states. This spin state change is accompanied by significant geometric changes such that low and high spin forms of a complex are distinct isomers that exist in equilibrium with one another. Typically, spin-state isomers interconvert rapidly and are similar enough in polarity to prevent their independent separation and isolation. We report here the first example, to our knowledge, of cobalt(II) spin-state isomers that can be physically separated. The reaction of Mo2(dpa)4 (dpa = 2,2'-dipyridylamide) with CoBr2 produces a mixture of two heterometallic compounds with a linear, metal-metal-bonded Mo[Formula: see text]Mo-Co chain. The complexes, SC-[BrMo2(dpa)4Co]Br (SC-2) and HS-[BrMo2(dpa)4CoBr] (HS-2), have identical compositions (Mo2Co(dpa)4Br2) but different ground spin states and coordination geometries of the Co(II) ion. In the solid state, SC-2 undergoes incomplete spin crossover from an S = 1/2 state to an S = 3/2 state, and HS-2 has a high spin, S = 3/2, ground state, as confirmed by SQUID magnetometry and EPR spectroscopy. Crystallographic analyses of SC-2 and HS-2 show that SC-2 has an elongated Co-Br distance relative to HS-2 and is best described as the salt [BrMo2(dpa)4Co]Br. This limits SC-2's solubility in nonpolar solvents and allows for the physical separation of the two isomers. Solution studies of SC-2 and HS-2 indicate that SC-2 and HS-2 interconvert slowly relative to the NMR time scale. Additional solution-state EPR and UV-vis absorption measurements demonstrate that the choice of solvent polarity determines the predominant isomer present in solution.

Antimicrobial properties of triazolato terpyridine Pd(II) and Pt(II) complexes formed by [3+2] cycloaddition coupling reaction

Modern classes of antimicrobials are crucial because most drugs in development today are basically antibiotic derivatives. Even though a large number of metal-based compounds have been studied as antimicrobial agents, relatively few studies have examined the antimicrobial properties of Pd(II) and Pt(II) compounds. The [3+2] cycloaddition reactions of [M(N3)L]PF6 (M = Pd(II) and Pt(II); L = 4′-(2-pyridyl)-2,2′:6′,2″-terpyridine) with 4,4,4-trifluoro-2-butynoic acid ethyl ester gave the corresponding triazolate complexes. The reaction products were fully characterized with a variety of analytical and spectroscopic tools including X-ray crystallographic analysis. The crystal structure of [Pd(triazolatoCF3,COOCH2CH3)L]PF6 provided cut-off evidence that the kinetically formed N1-triazolato isomer favoured the isomerization to the thermodynamically stable N2-analogue. The experimental work was complemented with computational work to get an insight into the nature of the predominant triazolate isomer. The lysozyme binding affinity of the triazolate complexes was examined by mass spectrometry. An analysis of the lysozyme Pd(II) adducts suggests a coordinative covalent mode of binding via the loss of the triazolato ligand. The free ligand and its triazolate complexes displayed selective toxicity against Candida albicans and Cryptococcus neoformans, while no cytotoxicity was observed against the normal human embryonic kidney cell line.

Reversible Restrain and Release of the Dynamic Valence Isomerization in a Shape-shifting Bullvalene by Complex Formation.

In search for structural features that enable the control of the valence isomerization of the fluxional bullvalene, a bullvalene-bis(harmane) conjugate is identified that acts as chelating ligand in complexes with metal ions. Spectrometric titrations show that this ligand forms 1 : 1 complexes with Ag+, Cu+, Cu2+, and Zn2+. Most importantly, detailed NMR-spectroscopic analysis at different temperatures reveals that the complexation with Ag+ strongly affects the dynamic isomerization of the bullvalene unit of the ligand such that only one predominant valence isomer is formed, even at 5 °C. Detailed 1H-NMR-spectroscopic studies disclose an increased barrier (~11 kJ mol-1) of the Cope rearrangement. Furthermore, the addition of hexacyclene displaces the Ag+ from the complex, so that the valence isomerization is accelerated and an equilibrium with two predominant isomers is formed. In turn, repeated addition of Ag+ regains the complex with the restrained isomerization of the bullvalene unit. This method to control the valence isomerism by straightforward chemical stimuli may be used to simplify structural analysis at elevated temperatures, i. e. a feature not available so far with bullvalenes, and it may be employed as functional element in dynamic supramolecular assemblies.

Distribution of gasification products and emission of heavy metals and dioxins from municipal solid waste at the low temperature pyrolysis stage.

Gasification is widely regarded as one of the most practical, economical, and environmentally friendly waste disposal technologies for municipal solid waste (MSW). The pyrolysis stage (300-500°C) is crucial for weight loss during MSW gasification, as a considerable amount of organic matter breaks down, producing high-value synthesis gas. This study investigated the product distribution and pollutant emission characteristics within this temperature range and its influencing factors during MSW gasification using a self-designed MSW gasification device. Results indicated that MSW underwent approximately 70% weight loss within this temperature range, yielding low amounts of inorganic and short-chain organic products, with mainly long-chain organic compounds of C16-C34. The atmosphere variation had minimal effect on the elemental composition and content of solid phase products. X-ray fluorescence spectrometry (XRF) and inductively coupled plasma mass spectrometry (ICP-MS) analyses showed that Mn and Zn were the primary components of heavy metal leaching toxicity in solid phase products, with their contents increasing as temperature increased. Synthesis gas showed the highest content of heavy metal As element, reaching a peak at 400°C. Higher gasification temperature and lower oxygen flow rate significantly reduced the dioxin content and I-TEQ values, with highly chlorinated isomers being the predominant dioxin isomers. Nonetheless, low-chlorinated dioxins accounted for more than 50% of the I-TEQ. This study improves our understanding of the gasification process of MSW.

A Review of Distribution and Profiles of HBCD in Different Environmental Media of China.

Hexabromocyclododecane (HBCD) is the most important flame retardant that has been used in Expanded Polystyrene foam and Extruded Polystyrene foam in the past forty years across the world. China was the major producer and user of HBCD, and the total HBCD production was about 0.3 million tons. Although HBCD was completely banned in China in 2021 because of its long-range transport, bioaccumulation and toxicity, there is still a lot of residue in the environment. Therefore, we reviewed multiple studies concerning the distribution of HBCD in diverse environmental matrices, such as in the air, dust, soil, water, sediment, and biota. Results revealed that HBCD levels in different environments in China present geographical variation and were at a high level compared with other countries. In all environmental media, relatively high HBCD concentrations have been found in industrial and urban areas. Industrialization and urbanization are two important factors that influence the concentration and distribution of HBCD in the environment. In terms of isomer, γ-HBCD was the dominant isomer in soil, water, and sediment, while in the biota α-HBCD was the predominant isomer.

Occurrences, Possible Sources, and Risk Impacts of Organochlorine Pesticides in Soil of Changchun Central Urban Area, Northeast China

Eighteen organochlorine pesticides (OCPs) in soil samples from the Changchun central urban area, Northeast China were analyzed using accelerated solvent extraction combined with gas chromatography/mass spectrometry (ASE-GC/MS) for the purpose of elucidating their contamination status, distribution characteristics, influencing factors, and feasible dangers in this city region. The complete concentrations of OCPs ranged from 15.63 to 92.79 ng/g, with a geomean of 36.46 ng/g. Hexachlorocyclohexane(HCHs), dichlorodiphenyltrichoroethane (DDTs), and chlordanes were the most dominant OCPs, with γ-HCH and p,p′-DDT being the predominant isomers. Higher concentrations of OCPs often centered to the northeast and southwest of the Changchun metropolis, and these artificial influences contributed to the destiny of OCPs in the soils. The residues of OCPs were derived from the historic utility of the technological DDT, dicofol, and lindane. A Pearson’s correlation evaluation indicated that TOC was once a key factor controlling OCP accumulation. The ecological risk evaluation based on the soil quality guidelines (SQGs) advises that the presence of DDTs, lindane, and heptachlor may additionally pose a poisonous ecological danger to soil organisms. The contrast outcomes of the incremental lifetime cancer risk (ILCR) confirmed that the highest cancer risk of OCPs to the posed populace was once low, whilst some unique areas with excessive OCP residues ought to be given attention. The research results provide basic information for evaluating the extent of OCP pollution in the soil of major cities in Northeast China and can help authorities establish environmental protection regulations and soil remediation techniques.

Phthalate metabolites in breast milk from mothers in Southern China: Occurrence, temporal trends, daily intake, and risk assessment

The extensive production and use of phthalates means that these compounds are now ubiquitous in the environment and various biota, which raises concerns about potential harmful health effects. In this study, phthalate metabolites (mPAEs) were measured in breast milk (n = 100) collected from mothers of southern China between 2014 − 2022. Of the nine target mPAEs, five were detected in all of the samples, including mono-methyl phthalate (MMP), mono-ethyl phthalate (MEP), mono-isobutyl phthalate (MiBP), mono-n-butyl phthalate (MnBP), and mono-(2-ethylhexyl) phthalate (MEHP). The total levels of mPAEs in breast milk ranged from 4.76 to 51.6 ng/mL, with MiBP and MnBP being the predominant isomers (MiBP + MnBP > 48.3%). Increasing trends were observed in MMP (5.7%/year) and MEHP (7.1%/year) levels during the study period, while a decreasing trend were observed in MiBP (−6.6%/year); no clear temporal trends were found for the other metabolites and total mPAE levels. The results indicate that exposure to phthalates is still prevalent in southern China. Breastfeeding was found to contribute to estimated daily phthalate intakes of 0.383–6.95 μg/kg-bw/day, suggesting insignificant health risks to infants based on dietary exposure. However, the increasing exposure to MMP and MEHP calls for more research into the possible sources and potential risks.

Composition and Bioactivity of Chlorogenic Acids in Vegetable and Conventional Sweet Potato Vine Tips.

Sweet potato vine tips are abundant in chlorogenic acid (CGA). In this study, CGA was extracted from vegetable and conventional sweet potato vine tips using ethanol, followed by subsequent purification of the extract through a series of sequential steps. Over 4 g of the purified product was obtained from 100 g of sweet potato vine tip powder, producing more than 85% of purified CGA. The LC-MS analysis of all samples indicated that 4-CQA was the predominant isomer in both sweet potato cultivars. Significant variations of p-coumaroyl quinic acids, feruloyl quinic acids, dicaffeoyl quinic acids, and tricaffeoyl quinic acid were identified, whereas the mono-caffeoyl quinic acids did not vary when the two sweet potato varieties were compared. Compared to conventional sweet potatoes, vegetable sweet potatoes exhibit a high negative correlation between 4-CQA and 5-pCoQA, while showing a high positive correlation between 3,5-CQA and 3-pCoQA. A series of principal component analyses (PCA) using CGA isomers enables a clear differentiation between vine tips derived from vegetable and conventional sweet potatoes. The model of linear discriminant analysis, based on the characteristic CGA, achieved a 100% accuracy rate in distinguishing between vegetable and conventional sweet potatoes. The high purity of sweet potato CGA (SCGA) exhibited potent anti-breast cancer activity. The results demonstrated that SCGA significantly suppressed the clonogenicity of MB231 and MCF7 cells, and impeded the migratory, invasive, and lung metastatic potential of MB231 cells.

Separation of D-Limonene and Other Oxygenated Compounds from Orange Essential Oil by Molecular Distillation and Fractional Distillation with a Wiped Film Evaporator

Orange essential oil (OEO) is mainly composed of D-Limonene and other oxygenated compounds that contribute to the orange flavor and aroma. However, D-Limonene is unstable in the presence of heat, light, and water, affecting the quality of the OEO. Therefore, the objective of this study was to fractionate OEO by distillation, both molecular and fractionated (hybrid), producing a D-Limonene-rich fraction. The OEO was characterized by physicochemical tests and gas chromatography combined with mass spectrometry (GC–MS). The fractionation of the OEO was carried out by molecular distillation and fractional distillation following, in both cases, a factorial design (23) with central points, considering the D-Limonene percentage in the distillate and the residue as a response variable. According to the physicochemical characterization, the predominant optical isomer was dextrorotatory, where D-Limonene is the main component of OEO (92.584%). For molecular distillation, the D-Limonene content was reduced to 47.964% in the residue or deterpenated fraction, while for fractional distillation, it was 86.779%. For this study, molecular distillation was considered a non-thermal process (use of low temperatures) that promoted the efficient recovery of oxygenated compounds. In contrast, fractional distillation favored the recovery of D-Limonene in the light fraction.

Reactivity of azido terpyridine Pd(ii) and Pt(ii) complexes towards 4,4,4-trifluoro-2-butynoic acid: structural insight into the triazolato coordination mode.

The mono- and binuclear azido terpyridine square-planar complexes of ionic formulas, [Pd2(N3)2L]2+ and [Pt(N3)L]+ (L = 1,4-bis(2,2':6',2''-terpyridin-4'yl)benzene), underwent the catalyst-free [3 + 2] cycloaddition coupling with 4,4,4-trifluoro-2-butynoic acid at ambient temperature affording the corresponding triazolate complexes. A mixture of triazolate isomers was generated by these inorganic click reactions. An increase in the solubility of the compounds was achieved by replacing the azido ligand with a triazolato ligand. By calculating the vibrational modes and comparing the total electronic and zero-point energy values, the local minimum structures of the complexes and the nature of the predominant triazolate isomer were verified. The theoretical work was complemented with natural bond analysis to get an insight into the natural charge and electronic arrangement of the metal ion, the hybridization of M-L bonds and strength of M-N bonds.

Supplementation with Sunflower/Fish Oil-Containing Concentrates in a Grass-Based Beef Production System: Influence on Fatty Acid Composition, Gene Expression, Lipid and Colour Stability and Sensory Characteristics of Longissimus Muscle.

Beef contains an array of conjugated linoleic acid (CLA) isomers for which positive effects have been reported in animal models of human disease. The objectives were to develop a CLA-enriched beef production system and to assess its quality. Sixty Spring-born heifers were housed in Autumn and offered unwilted grass silage and a barley/soyabean concentrate or wilted grass silage and a concentrate containing sunflower oil and fish oil. In May, both groups were offered either pasture for 22 weeks, restricted pasture and sunflower oil and fish oil for 22 weeks, or pasture for 11 weeks and restricted pasture and sunflower oil and fish oil for the final 11 weeks. The predominant CLA isomer in beef was cis9, trans11 representing on average, 80% total CLA. The modified winter diet followed by supplementation for 22 weeks resulted in beef that had a CLA concentration that was higher, at a comparable intramuscular fatty acid concentration, than previously reported. The lipid and colour stability (over 10 days in modified atmosphere packaging) and sensory characteristics were generally not negatively affected. There were minor effects on the expression of candidate genes involved in lipid metabolism. Consumption of this beef would make a substantial contribution to the quantity of CLA suggested to have a positive effect on consumer health.

Differential expression of AMPK subunit isoforms in subcutaneous adipose tissue of post-mortem subjects with BMI>25kg/m2

AMP-activated protein kinase (AMPK) is a heterotrimeric complex that is made up of α-, β- and γ- subunits isoforms making up various isomers. AMPK has been shown to improve catabolic ATP-generating pathways, making it a promising therapeutic target. Studies have shown that different AMPK isomers are predominant in different tissues. However, determination of the predominant isomer in adipose tissue remains obscure. The goal of this study is to identify the AMPK isomers present in human subcutaneous adipose tissues comparing between lean and overweight/obese subjects. Total RNA from post-mortem subcutaneous adipose tissue was extracted and its quantity and integrity were evaluated using a bioanalyzer before being reverse transcribed to cDNA. Then, by using SYBR-green as a fluorophore detection, quantitative real-time PCR was performed. The relative expression of each target gene was calculated using the comparative 2-∆∆Ct method, and the expression levels of target genes were normalized to that of GAPDH, RPLP0, and HPRT1. Mean differences of AMPK subunits mRNA level for both lean and overweight/obese subjects were determined by Mann-Whitney for two-sample comparisons using SPSS 26.0 (SPSS Inc., USA). This study revealed that in overweight/obese subjects, the gene expression of α1-AMPK was upregulated (2.5-fold) whilst α2-AMPK was downregulated (0.5-fold) when compared to lean controls (p=0.044). There were no differences observed between the β and γ subunits in both lean and overweight/obese subjects. Findings from this study suggests that α1- and α2-AMPK gene expression plays an important role in overweight/obese subjects. Future studies to explore the AMPK gene expressions in visceral adipose tissue and among underweight subjects would further close this knowledge gap.

A highly regio- and stereoselective Pd-catalyzed electrocarboxylation of Baylis-Hillman acetates: An interesting switchable regioselectivity based on electrode material

We developed a novel regio- and stereoselective palladium catalyzed electrocarboxylation of Baylis-Hillman acetates. We found an interesting unprecedented electrode material-controlled switchable regioselectivity. When Platinum was taken as cathode, benzylic carboxylation products were found to be the predominant regioisomers (condition A). Under similar reaction conditions when Nickel was taken as cathode, a complete reversal in regioselectivity was observed providing cinnamyl carboxylation products as the predominant regio isomers with exclusively (E)-stereochemistry (condition B). We proposed plausible mechanisms to explain the switch in regioselectivity which were further supported by TEMPO experiments.

A nationwide survey of 20 legacy brominated flame retardants in indoor dust from China: continuing occurrence, national distribution, and implication for human exposure.

Despite the restrictions on polybrominated diphenyl ethers (PBDEs) and hexabromocyclododecanes (HBCDDs), these chemicals are still ubiquitous environmental pollutants. In this study, we measured the concentrations and profiles of 17 PBDE congeners and 3 HBCDD isomers in indoor dust samples collected from 23 provinces and cities across China. The summed concentrations of PBDEs (Σ17PBDEs) ranged from 4.19 to 817ng/g, with an average of 171 ± 184ng/g. BDE-209 was the most abundant congener. The concentrations of HBCDDs ranged from 6.65 to 1335ng/g, with an average of 236 ± 324ng/g. Unlike commercial HBCDD formulations, α-HBCDD was the predominant isomer in the indoor dust samples analyzed. Geographical distributions showed that the concentrations of PBDEs and HBCDDs varied significantly among different regions. Higher PBDE and HBCDD levels were observed in samples from eastern coastal and economically developed regions. Further, we estimated the daily intakes of PBDEs and HBCDDs through the routes of dust ingestion and dust dermal absorption for different age groups. Dust dermal absorption is an unneglectable exposure pathway to PBDEs and HBCDs for the Chinese population. Among the age groups, infants had the highest exposure via dust dermal absorption, and toddlers had the highest exposure via dust ingestion. Compared with the threshold values, the exposure doses of PBDEs and HBCDDs are unlikely to pose significant health concerns for both infants and adults in China. This is the first national survey of PBDEs and HBCDDs in indoor dust samples across China after the restriction.

Toxicological Analysis of Fluorofentanyl Isomers in Postmortem Blood.

The opioid epidemic continues to evolve in the USA, with fentanyl the most prevalent synthetic opioid in fatal drug overdoses. Following the scheduling of fentanyl's core structure in 2018, there was a notable decline in the prevalence of fentanyl analogs in decedents; however, fluorofentanyl began being reported in casework in the winter of 2020. Fluorofentanyl has three positional isomers (para-fluorofentanyl (p-FF), ortho-fluorofentanyl (o-FF) and meta-fluorofentanyl (m-FF)), with the most predominant isomer that has recently emerged in the USA being p-FF. The goal of this study was to identify p-FF in postmortem cases between October 2020 and April 2021. Urine and blood were extracted using UCT Clean Screen® extraction columns and then screened using an Agilent 1290 Infinity liquid chromatograph (LC) coupled to an Agilent 6545 accurate mass time-of-flight mass spectrometer (TOF-MS) and quantified using an Agilent 6890N GC system coupled with an Agilent 5973 MS. The limit of quantitation (LOQ) for fentanyl, acetyl fentanyl, butyryl fentanyl, p-FF, o-FF and m-FF was 2.5 ng/mL. The screening method could not differentiate the three positional isomers of fluorofentanyl. Suspected overdose cases (n = 370) received from October 2020 through April 2021 from four Medical Examiner Districts in the state of Florida were analyzed for the presence of fluorofentanyl. The LC-QTOF-MS screen yielded 27 decedents positive for fluorofentanyl, with a majority being Caucasian (93%) and male (70%) with ages ranging from 27 to 63 years. Analysis of the blood and urine by GC-MS yielded 14 decedents positive for p-FF, nine of which were positive in the blood. The blood concentrations (n = 9) for p-FF ranged from <LOQ to 30 ng/mL, with an average and median of 9.9 ng/mL and 5.5 ng/mL, respectively. p-FF was identified in the blood of 33% of the cases, and the concentration of p-FF was generally higher than previously reported.

Tocochromanol Profiles in Chlorella sorokiniana, Nannochloropsis limnetica and Tetraselmis suecica Confirm the Presence of 11'-α-Tocomonoenol in Cultured Microalgae Independently of Species and Origin.

11′-α-Tocomonoenol (11′-αT1) is structurally related to vitamin E and has been quantified in the microalgae Tetraselmis sp. and Nannochloropsis oceanica. However, it is not known whether 11′-αT1 is present in other microalgae independent of species and origin. The aim of this study was to analyze the tocochromanol profiles of Chlorella sorokiniana, Nannochloropsis limnetica, and Tetraselmis suecica and to determine if 11′-αT1 is present in these microalgae. Cultured microalgae were freeze-dried and the presence and identity of α-tocomonoenols were confirmed by LC-MSn (liquid chromatography coupled to mass spectroscopy) and GC-MS (gas chromatography coupled to mass spectroscopy). Tocochromanol profiles were determined by HPLC-FLD (liquid chromatography with fluorescence detection) and fatty acid profiles (as fatty acid methyl esters; FAME) by GC-MS. As confirmed by LC-MSn and GC-MS, 11′-αT1 was the dominant αT1 isomer in cultured microalgae instead of 12′-αT1, the isomer also known as marine-derived tocopherol. αT1 represented less than 1% of total tocochromanols in all analyzed samples and tended to be more abundant in microalgae with higher proportions of polyunsaturated fatty acids. In conclusion, our findings confirm that αT1 is not restricted to terrestrial photosynthetic organisms, but can also accumulate in microalgae of different species, with 11′-αT1—and not the marine-derived tocopherol (12′-αT1)—as the predominant αT1 isomer.

Simulation and analysis of the relaxation dynamics of a photochromic furylfulgide.

Furylfulgides, a class of photochromic organic compounds, show a complex system of photoinduced reactions. In the present study, the excited-state dynamics of the Eα and Eβ isomers of a representative furylfulgide is modelled with the use of nonadiabatic molecular dynamics simulations. Moreover, a pattern recognition algorithm is employed in order to automatically identify relaxation pathways, and to quantify the photoproduct distributions. The simulation results indicate that, despite differing only in the orientation of the furyl group, the two isomers show markedly different photochemical behaviour. The predominant Eα isomer undergoes photocyclisation with a quantum yield (QY) of 0.27 ± 0.10. For this isomer, the undesired E → Z photoisomerisation around the central double bond represents a minor side reaction, with a QY of 0.09 ± 0.07. In contrast, the minority Eβ isomer, which is incapable of photocyclisation, undergoes efficient E → Z photoisomerisation, with a QY as high as 0.56 ± 0.14. The relaxation kinetics and the photoproduct distributions are interpreted in the light of the available experimental data.

Application of E/Z-Isomerization Technology for Enhancing Processing Efficiency, Health-Promoting Effects, and Usability of Carotenoids: A Review and Future Perspectives.

Carotenoids are naturally occurring pigments whose presence in the diet is beneficial to human health. Moreover, they have a wide range of applications in the food, cosmetic, and animal feed industries. As carotenoids contain multiple conjugated double bonds in the molecule, a large number of geometric (E/Z, trans/cis) isomers are theoretically possible. In general, (all-E)-carotenoids are the most predominant geometric isomer in nature, and they have high crystallinity and low solubility in various mediums, resulting in their low processing efficiency and bioavailability. Technological developments for improving the processing efficiency and bioavailability of carotenoids utilizing the Z-isomerization have recently been gaining traction. Namely, Z-isomerization of carotenoids induces a significant change in their physicochemical properties (e.g., solubility and crystallinity), leading to improved processing efficiency and bioavailability as well as several biological activities. For the practical use of isomerization technology for carotenoids, the development of efficient isomerization methods and an acute understanding of the changes in biological activity are required. This review highlights the recent advancements in various conventional and unconventional methods for carotenoid isomerization, such as thermal treatment, light irradiation, microwave irradiation, and catalytic treatment, as well as environment-friendly isomerization methods. Current progress in the improvement of processing efficiency and biological activity utilizing isomerization technology and an application development of carotenoid Z-isomers for the feed industry are also described. In addition, future research challenges in the context of carotenoid isomerization have been elaborated upon.