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Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules

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A special issue of Symmetry (ISSN 2073-8994). This special issue belongs to the section "Chemistry: Symmetry/Asymmetry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 19437

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Special Issue Editor

Dr. Yutaka Itabashi

E-Mail Website1 Website2
Guest Editor

Japan Association for Inspection and Investigation of Foods including Fats and Oils, Tokyo, Japan
Interests: lipid chemistry; analytical chemistry; stereochemistry of lipids; analysis of lipids and fatty acids; chromatography; mass spectrometry

Special Issue Information

Dear Colleagues,

Biomolecules, also called biological molecules are the substances produced by living organisms that play important roles in chemical and biological processes. They include large molecules such as proteins, carbohydrates, lipids, and nucleic acids, as well as small molecules such as primary and secondary metabolites, and natural products. Many biomolecules are complex mixtures of different types of isomers that contain enantiomers and regioisomers. Although the analytical technologies and methodologies have advanced rapidly in recent years, there are still many biomolecules for which detection and separation are difficult to achieve and in which physiological significance and biological activities remain unknown. This would encourage new discoveries in both basic and applied research on isomeric biomolecules.

In this Special Issue, we cordially invite and welcome review, expository, and original research articles dealing with recent advances in the subjects of analysis, distribution, and functions of isomeric biomolecules, including enzyme regio- and enantio-specificities.

Dr. Yutaka Itabashi
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Symmetry is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2400 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

Biomolecules, natural products, and metabolites
Fatty acids, amino acids and sugars
Enantiomers and diastereomers
Regioisomers (positional isomers)
Chirality of biomolecules
Analysis, distribution, and function of isomeric biomolecules
Enzyme specificity and selectivity
Chromatography and spectrometry

Published Papers (7 papers)

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Research

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6 pages, 1048 KiB

Open AccessCommunication

Isolation and Structure Elucidation of a Novel Symmetrical Macrocyclic Phthalate Hexaester

by Michiya Kamio, Weina Jiang, Hiroki Osada, Masayuki Fukuoka, Hajime Uchida, Ryuichi Watanabe, Toshiyuki Suzuki and Hiroshi Nagai

Symmetry 2021, 13(2), 361; https://0-doi-org.brum.beds.ac.uk/10.3390/sym13020361 - 23 Feb 2021

Cited by 1 | Viewed by 1908

Abstract

A novel symmetrical macrocyclic phthalate hexaester (1) and a known macrocyclic phthalate tetraester (2) were isolated during a natural product-exploring program on the cyanobacterium Moorea producens. Their structures were elucidated based on spectroscopic data, including nuclear magnetic resonance [...] Read more.

(This article belongs to the Special Issue Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules)

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7 pages, 632 KiB

Open AccessArticle

Simultaneous Quantification of Mixed-Acid Triacylglycerol Positional Isomers and Enantiomers in Palm Oil and Lard by Chiral High-Performance Liquid Chromatography Coupled with Mass Spectrometry

by Toshiharu Nagai, Tetsuaki Kinoshita, Erika Kasamatsu, Kazuaki Yoshinaga, Hoyo Mizobe, Akihiko Yoshida, Yutaka Itabashi and Naohiro Gotoh

Symmetry 2020, 12(9), 1385; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12091385 - 19 Aug 2020

Cited by 8 | Viewed by 2479

Abstract

Palm oil and lard are edible fats which are rich in palmitic (P) and oleic acids (O). In this study, triacylglycerol (TAG) positional isomers (symmetric and asymmetric isomers) and enantiomers (asymmetric isomers) in palm oil and lard were quantified simultaneously by using liquid chromatography/mass spectrometry. The CHIRALPAK IF-3 column used in our previous study recognized the difference of TAG isomers consisting of P and O in palm oil and lard, separated sn-OPP/sn-PPO/sn-POP and sn-OPO/sn-OOP/sn-POO into each isomer peak, and enabled the quantification of these TAG isomers with good recovery (95–120%). Although sn-POP and sn-OPO were the major TAGs in palm oil and lard, a comparison of the abundance ratios of TAG enantiomers such as sn-PPO/sn-OPP and sn-OOP/sn-POO revealed that there were slightly more TAG enantiomers with O at the sn-1 position and P at the sn-3 position in palm oil and P at the sn-1 position and O at the sn-3 position in lard. These results were consistent with previous reports for the positional distribution of fatty acids of palm oil and lard. This is the first study that has enabled all TAG isomers consisting of P and O in natural oils and fats to be individually quantified by mass spectrometry. Full article

(This article belongs to the Special Issue Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules)

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10 pages, 824 KiB

Open AccessArticle

Direct Separation of the Diastereomers of Cholesterol Ester Hydroperoxide Using LC-MS/MS to Evaluate Enzymatic Lipid Oxidation

by Junya Ito, Naoki Shimizu, Shunji Kato, Yusuke Ogura and Kiyotaka Nakagawa

Symmetry 2020, 12(7), 1127; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12071127 - 07 Jul 2020

Cited by 6 | Viewed by 3051

Abstract

Cholesterol ester hydroperoxide (CEOOH) is one of the main lipid oxidation products contained in oxidized low-density lipoprotein (LDL). Previous studies suggest that CEOOH in oxidized LDL is closely related to several diseases. Of the oxidation mechanisms of cholesterol ester (CE) in vivo, it has been suggested that enzymatic oxidation induced by lipoxygenase (LOX) plays an important role. Thus, we attempted to develop a method that can evaluate the enzymatic oxidation of CE via the diastereoselective separation of CEOOH bearing 13RS-9Z,11E-hydroperoxy-octadecadienoic acid (13(RS)-HPODE CE). Firstly, we synthesized the standard of 13(RS)-HPODE CE. Using this standard, the screening of analytical conditions (i.e., column, mobile phase, and column temperature) was conducted, and separation of the diastereomers of 13(RS)-HPODE CE was achieved. The diastereoselective separation of 13(RS)-HPODE CE was also confirmed by LC-MS/MS. The developed method (column, CHIRALPAK IB N-3; mobile phase, hexane:ethanol (100:1, v/v); column temperature, 0 °C) can distinguish between enzymatic oxidation and other oxidation mechanisms of CE. Thus, the method can be expected to provide a greater understanding of the biochemical oxidation mechanisms in vivo. Such information will be essential to further elucidate the involvement of CEOOH in various diseases. Full article

(This article belongs to the Special Issue Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules)

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13 pages, 4446 KiB

Open AccessFeature PaperArticle

Possibility of Using Astaxanthin-Rich Dried Cell Powder from Paracoccus carotinifaciens to Improve Egg Yolk Pigmentation of Laying Hens

by Masaki Honda, Yuki Kawashima, Kazuaki Hirasawa, Takeshi Uemura, Sun Jinkun and Yoshiaki Hayashi

Symmetry 2020, 12(6), 923; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12060923 - 02 Jun 2020

Cited by 17 | Viewed by 3179

Abstract

The study investigated egg quality aspects such as astaxanthin concentration, E/Z-isomer ratio, and yolk color in laying hens fed with astaxanthin-containing diets. Dried Paracoccus carotinifaciens cell powder (Panaferd-AX) and fine cell powder (Panaferd-P) were used as sources of astaxanthin, with average particle diameters of approximately 100 μm and 10 μm, respectively. Paracoccus carotinifaciens contains valuable rare carotenoids such as adonirubin and adonixanthin, and thus the concentrations of these carotenoids in egg yolk were also evaluated. The E/Z-isomer ratios of the egg yolk carotenoids were determined by normal-phase high-performance liquid chromatography (HPLC) with an improved solvent system. Feeding diets containing P. carotinifaciens resulted in increased concentrations of astaxanthin, adonirubin, and adonixanthin in egg yolk, as well as a marked increase in the yolk color fan score; values associated with the Panaferd-P-containing diet were higher than those associated with the Panaferd-AX-containing diet. For example, the astaxanthin concentration in egg yolks of hens fed with the Panaferd-AX- and Panaferd-P-containing diets for 21 days were 1.21 μg/g and 1.85 μg/g, respectively. This indicates that the pulverization treatment of the P. carotinifaciens powder increased the efficiency of carotenoid accumulation in the egg yolk. Moreover, more than 95% of astaxanthin in P. carotinifaciens was present as the all-E-isomer. However, approximately 25% of astaxanthin in egg yolk was present as the Z-isomers. In recent years, astaxanthin Z-isomers have attracted substantial attention as they exhibit a greater bioavailability and bioactivity than the all-E-isomer. These data are important not only for understanding egg yolk pigmentation but also for improving the nutritional value of hens’ egg yolk through the addition of P. carotinifaciens to their diet. Full article

(This article belongs to the Special Issue Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules)

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14 pages, 977 KiB

Open AccessFeature PaperArticle

Simultaneous Analysis of d,l-Amino Acids in Human Urine Using a Chirality-Switchable Biaryl Axial Tag and Liquid Chromatography Electrospray Ionization Tandem Mass Spectrometry

by Masashi Harada, Sachise Karakawa, Hiroshi Miyano and Kazutaka Shimbo

Symmetry 2020, 12(6), 913; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12060913 - 02 Jun 2020

Cited by 14 | Viewed by 3031

Abstract

Although d,l-amino acids are symmetrical molecules, l-isomers are generally dominant in living organisms. However, it has been found that some d-amino acids also have biological functions. A new method for simultaneously analyzing d,l-amino acids in biological samples is required to allow unknown functions of d-amino acids to be investigated. d-Amino acids in urine are currently receiving increasing amounts of attention, particularly for screening for chronic kidney diseases. However, simultaneously analyzing d,l-amino acids in human urine is challenging because of interfering unknown compounds in urine. In this study, the axially chiral derivatizing agent (R)-4-nitrophenyl-N-[2-(diethylamino)-6,6-dimethyl-[1,1-biphenyl]-2-yl] carbamate hydrochloride was used to allow enantiomers of amino acids in human urine to be simultaneously determined by liquid chromatography electrospray ionization tandem mass spectrometry. The optimized method gave good linearities, precision results, and recoveries for 18 proteinogenic amino acids and their enantiomers and glycine. The chiral-switching method using (S)-4-nitrophenyl-N-[2-(diethylamino)-6, 6-dimethyl-[1,1-biphenyl]-2-yl]carbamate hydrochloride confirmed the expected concentrations of 32 of the 37 analytes. The method was successfully used to determine the concentrations of d-serine, d-alanine, d-asparagine, d-allothreonine, d-lysine, and the d-isomers of 10 other amino acids in five human volunteer urine samples. Full article

(This article belongs to the Special Issue Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules)

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10 pages, 2490 KiB

Open AccessArticle

One-Step Preparation of Z-Isomer-Rich β-Carotene Nanosuspensions Utilizing a Natural Catalyst, Allyl Isothiocyanate, via Supercritical CO₂

by Yelin Zhang, Masaki Honda, Tetsuya Fukaya, Wahyudiono, Hideki Kanda and Motonobu Goto

Symmetry 2020, 12(5), 777; https://0-doi-org.brum.beds.ac.uk/10.3390/sym12050777 - 07 May 2020

Cited by 8 | Viewed by 2317

Abstract

This study aims to improve the production efficiency of β-carotene suspensions using a naturally occurring Z-isomerization-accelerating catalyst, allyl isothiocyanate (AITC), via supercritical CO₂ (SC-CO₂). Namely, utilizing solubility improvement of β-carotene with the Z-isomerization by adding AITC in the SC-CO₂-used dispersion process, the encapsulation efficiency of β-carotene was enhanced. The dispersion of β-carotene was conducted by ultrasonic treatment, and there was no involvement of organic solvents in the whole process. When 100 mg of AITC was added in the dispersion process, the encapsulation efficiency (β-carotene content in resulting suspension) was approximately 3.5 times higher than that without addition of the catalyst. Moreover, the Z-isomer ratio of β-carotene in the suspensions significantly improved, that is, it was approximately 12 times higher than the raw β-carotene material. Since Z-isomers of β-carotene are known to have higher antiatherosclerotic and antiatherogenic activities compared to the all-E-isomer, this one-step method not only efficiently produces β-carotene suspensions without organic solvents but also enhances the bioactivities of them. Full article

(This article belongs to the Special Issue Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules)

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Review

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16 pages, 673 KiB

Open AccessReview

Regio- and Stereospecific Analysis of Triacylglycerols—A Brief Overview of the Challenges and the Achievements

by Svetlana Momchilova and Boryana Nikolova-Damyanova

Symmetry 2022, 14(2), 247; https://0-doi-org.brum.beds.ac.uk/10.3390/sym14020247 - 27 Jan 2022

Cited by 5 | Viewed by 2625

Abstract

The efforts to reveal, in detail, the molecular and intramolecular structures of one of the main lipid classes, namely, triacyl-sn-glycerols, which are now known to affect their specific and important role in all living organisms, are briefly overviewed. Some milestones of significance in the gradual but continuous development and improvement of the analytical methodology to identify the triacylglycerol regio- and stereoisomers in complex lipid samples are traced throughout the years: the use of chromatography based on different separation principles; the improvements in the chromatographic technique; the development and use of different detection techniques; the attempts to simplify and automatize the analysis without losing the accuracy of identification. The spectacular recent achievements of two- and multidimensional methods used as tools in lipidomics are presented. Full article

(This article belongs to the Special Issue Recent Advances in the Analysis, Distribution and Functions of Enantiomers and Regioisomers of Biomolecules)

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