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Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 14442

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Prof. Dr. Attila Agócs

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Department of Biochemistry and Medical Chemistry, University of Pécs Medical School, Pécs, Hungary
Interests: carotenoid chemistry; synthesis; isolation; antioxidant activity; biochemical activity

Prof. Dr. Sangho Koo

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Guest Editor

Department of Chemistry; Department of Energy Science and Technology, Myongji University, Yongin, Korea
Interests: organic synthesis; carotenoids; terpenoids; carbocycles; heterocycles; antioxidants; organic molecular wires; biomass conversion

Special Issue Information

Dear Colleagues,

Carotenoids are colourful pigments that are prevalent in nature. Carotenoids play important roles as antioxidants in health promotion and disease prevention and also participate in many other activities, such as energy production and vision.

Carotenoid research at present focuses not only on isolation and structure elucidation from natural sources but also on the synthesis and semi-synthesis of carotenoid-like poly-isoprenoids. To better understand the function or structure–activity relationships of natural or non-natural carotenoids, various physical and chemical properties can be measured, such as electronic properties, membrane penetration properties, antioxidant activity, and changes in spectroscopic properties.

We invite you to submit original research papers or review articles focusing on all issues related to carotenoid chemistry in a wider sense.

Prof. Dr. Attila Agócs
Prof. Dr. Sangho Koo
Guest Editors

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Keywords

carotenoids
isolation
synthesis
structure elucidation
analysis
biochemical function
physico-chemical properties
all other topics related to carotenoid chemistry

Published Papers (6 papers)

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Research

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20 pages, 5511 KiB

Open AccessArticle

Excited-State Dynamics of All the Mono-cis and the Major Di-cis Isomers of β-Apo-8′-Carotenal as Revealed by Femtosecond Time-Resolved Transient Absorption Spectroscopy

by Kota Horiuchi, Chiasa Uragami, Ruohan Tao, Daisuke Kosumi, Richard J. Cogdell and Hideki Hashimoto

Molecules 2023, 28(11), 4424; https://doi.org/10.3390/molecules28114424 - 29 May 2023

Cited by 1 | Viewed by 1799

Abstract

Cis isomers of carotenoids play important roles in light harvesting and photoprotection in photosynthetic bacteria, such as the reaction center in purple bacteria and the photosynthetic apparatus in cyanobacteria. Carotenoids containing carbonyl groups are involved in efficient energy transfer to chlorophyll in light-harvesting complexes, and their intramolecular charge–transfer (ICT) excited states are known to be important for this process. Previous studies, using ultrafast laser spectroscopy, have focused on the central-cis isomer of carbonyl-containing carotenoids, revealing that the ICT excited state is stabilized in polar environments. However, the relationship between the cis isomer structure and the ICT excited state has remained unresolved. In this study, we performed steady-state absorption and femtosecond time-resolved absorption spectroscopy on nine geometric isomers (7-cis, 9-cis, 13-cis, 15-cis, 13′-cis, 9,13′-cis, 9,13-cis, 13,13′-cis, and all-trans) of β-apo-8′-carotenal, whose structures are well-defined, and discovered correlations between the decay rate constant of the S₁ excited state and the S₀−S₁ energy gap, as well as between the position of the cis-bend and the degree of stabilization of the ICT excited state. Our results demonstrate that the ICT excited state is stabilized in polar environments in cis isomers of carbonyl-containing carotenoids and suggest that the position of the cis-bend plays an important role in the stabilization of the excited state. Full article

(This article belongs to the Special Issue Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function)

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14 pages, 4732 KiB

Open AccessArticle

Photoinduced Dynamics of 13,13′-Diphenylpropyl-β-carotene

by Sangho Koo, Yeong Hun Kim, Oliver Flender, Mirko Scholz, Kawon Oum and Thomas Lenzer

Molecules 2023, 28(8), 3505; https://doi.org/10.3390/molecules28083505 - 16 Apr 2023

Viewed by 975

Abstract

Carotenoids are ubiquitous pigment systems in nature which are relevant to a range of processes, such as photosynthesis, but the detailed influence of substitutions at the polyene backbone on their photophysics is still underexplored. Here, we present a detailed experimental and theoretical investigation of the carotenoid 13,13′-diphenylpropyl-β-carotene using ultrafast transient absorption spectroscopy and steady-state absorption experiments in n-hexane and n-hexadecane, complemented by DFT/TDDFT calculations. In spite of their bulkiness and their potential capability to “fold back” onto the polyene system, which could result in π-stacking effects, the phenylpropyl residues have only a minor impact on the photophysical properties compared with the parent compound β-carotene. Ultrafast spectroscopy finds lifetimes of 200–300 fs for the S₂ state and 8.3–9.5 ps for the S₁ state. Intramolecular vibrational redistribution with time constants in the range 0.6–1.4 ps is observed in terms of a spectral narrowing of the S₁ spectrum over time. We also find clear indications of the presence of vibrationally hot molecules in the ground electronic state (S₀*). The DFT/TDDFT calculations confirm that the propyl spacer electronically decouples the phenyl and polyene π-systems and that the substituents in the 13 and 13′ positions point away from the polyene system. Full article

(This article belongs to the Special Issue Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function)

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15 pages, 1589 KiB

Open AccessArticle

β-Cryptoxanthin Attenuates Cigarette-Smoke-Induced Lung Lesions in the Absence of Carotenoid Cleavage Enzymes (BCO1/BCO2) in Mice

by Rachel A. Chiaverelli, Kang-Quan Hu, Chun Liu, Ji Ye Lim, Michael S. Daniels, Hui Xia, Jonathan Mein, Johannes von Lintig and Xiang-Dong Wang

Molecules 2023, 28(3), 1383; https://doi.org/10.3390/molecules28031383 - 01 Feb 2023

Cited by 3 | Viewed by 1582

Abstract

High dietary intake of β-cryptoxanthin (BCX, an oxygenated provitamin A carotenoid) is associated with a lower risk of lung disease in smokers. BCX can be cleaved by β-carotene-15,15′-oxygenase (BCO1) and β-carotene-9′,10′-oxygenase (BCO2) to produce retinol and apo-10′-carotenoids. We investigated whether BCX has protective effects against cigarette smoke (CS)-induced lung injury, dependent or independent of BCO1/BCO2 and their metabolites. Both BCO1^−/−/BCO2^−/− double knockout mice (DKO) and wild type (WT) littermates were supplemented with BCX 14 days and then exposed to CS for an additional 14 days. CS exposure significantly induced macrophage and neutrophil infiltration in the lung tissues of mice, regardless of genotypes, compared to the non-exposed littermates. BCX treatment significantly inhibited CS-induced inflammatory cell infiltration, hyperplasia in the bronchial epithelium, and enlarged alveolar airspaces in both WT and DKO mice, regardless of sex. The protective effects of BCX were associated with lower expression of IL-6, TNF-α, and matrix metalloproteinases-2 and -9. BCX treatment led to a significant increase in hepatic BCX levels in DKO mice, but not in WT mice, which had significant increase in hepatic retinol concentration. No apo-10′-carotenoids were detected in any of the groups. In vitro BCX, at comparable doses of 3-OH-β-apo-10′-carotenal, was effective at inhibiting the lipopolysaccharide-induced inflammatory response in a human bronchial epithelial cell line. These data indicate that BCX can serve as an effective protective agent against CS-induced lung lesions in the absence of carotenoid cleavage enzymes. Full article

(This article belongs to the Special Issue Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function)

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20 pages, 6030 KiB

Open AccessArticle

A Computer Simulation Insight into the Formation of Apocarotenoids: Study of the Carotenoid Oxygenases BCO1 and BCO2 and Their Interaction with Putative Substrates

by Anabela Martínez, Jorge Cantero, Antonio J. Meléndez-Martínez and Margot Paulino

Molecules 2022, 27(22), 7813; https://doi.org/10.3390/molecules27227813 - 13 Nov 2022

Viewed by 1192

Abstract

Carotenoids are isoprenoid pigments, and sources of vitamin A in humans. The first metabolic pathway for their synthesis is mediated by the enzymes β,β-carotene-15,15′-dioxygenase (BCO1) and β,β-carotene-9′,10′-dioxygenase (BCO2), which cleave carotenoids into smaller compounds, called apocarotenoids. The objective of this study is to gain insight into the interaction of BCO1 and BCO2 with carotenoids, adding structural diversity and importance in the agro-food and/or health sectors. Homology modeling of BCO1 and BCO2, and the molecular dynamics of complexes with all carotenoids were performed. Interaction energy and structures were analyzed. For both enzymes, the general structure is conserved with a seven beta-sheet structure, and the β-carotene is positioned at an optimal distance from the catalytic center. Fe²⁺ forms in an octahedral coordination sphere with four perfectly conserved histidine residues. BCO1 finds stability in a structure in which the β-carotene is positioned ready for enzymatic catalysis at the 15–15′ bond, and BCO2 in positioning the bond to be cleaved (C9–C10) close to the active site. In BCO1 the carotenoids interact with only seven residues with aromatic rings, while the interaction of BCO2 is much more varied in terms of the type of interaction, with more residues of different chemical natures. Full article

(This article belongs to the Special Issue Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function)

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19 pages, 3663 KiB

Open AccessArticle

Synthesis, Pharmacokinetic Characterization and Antioxidant Capacity of Carotenoid Succinates and Their Melatonin Conjugates

by Dalma Czett, Katalin Böddi, Veronika Nagy, Anikó Takátsy, József Deli, Paul Tone, György T. Balogh, Anna Vincze and Attila Agócs

Molecules 2022, 27(15), 4822; https://doi.org/10.3390/molecules27154822 - 28 Jul 2022

Cited by 1 | Viewed by 1257

Abstract

Carotenoid succinates were synthesized from hydroxy carotenoids and were coupled to a commercially available derivative of melatonin via amide bond for producing more powerful anti-oxidants and yet new hybrid lipophilic bifunctional molecules with additional therapeutic effects. The coupling reactions produced conjugates in acceptable to good yields. Succinylation increased the water solubility of the carotenoids, while the conjugation with melatonin resulted in more lipophilic derivatives. The conjugates showed self-assembly in aqueous medium and yielded relatively stable colloidal solutions in phosphate-buffered saline. Antioxidant behavior was measured with ABTS and the FRAP methods for the carotenoids, the carotenoid succinates, and the conjugates with melatonin. A strong dependence on the quality of the solvent was observed. TEAC values of the new derivatives in phosphate-buffered saline were found to be comparable to or higher than those of parent carotenoids, however, synergism was observed only in FRAP assays. Full article

(This article belongs to the Special Issue Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function)

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Review

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17 pages, 943 KiB

Open AccessReview

The Role of Astaxanthin as a Nutraceutical in Health and Age-Related Conditions

by Geir Bjørklund, Amin Gasmi, Larysa Lenchyk, Mariia Shanaida, Saba Zafar, Pavan Kumar Mujawdiya, Roman Lysiuk, Halyna Antonyak, Sadaf Noor, Muhammad Akram, Kateryna Smetanina, Salva Piscopo, Taras Upyr and Massimiliano Peana

Molecules 2022, 27(21), 7167; https://doi.org/10.3390/molecules27217167 - 23 Oct 2022

Cited by 15 | Viewed by 6873

Abstract

The current review provides an up-to-date analysis of scientific data on astaxanthin (ASX) sources and experimental studies on its health benefits as a potent antioxidant in the aging process. ASX is a liposoluble carotenoid nutrient and reddish-orange pigment, naturally synthesized by numerous microalgae, yeasts, and bacteria as secondary metabolites. Provides a reddish hue to redfish and shellfish flesh that feed on ASX-producing microorganisms. The microalga Haematococcus pluvialis is the most important source for its industrial bioproduction. Due to its strong antioxidant properties, numerous investigations reported that natural ASX is a more significant antioxidant agent than other antioxidants, such as vitamin C, vitamin E, and β-carotene. Furthermore, several data show that ASX possesses important nutraceutical applications and health benefits, especially in healthy aging processes. However, further studies are needed for a deeper understanding of the potential mechanisms through which ASX could lead to its effective role in the healthy aging process, such as supporting brain health and skin homeostasis. This review highlights the current investigations on the effective role of ASX in oxidative stress, aging mechanisms, skin physiology, and central nervous system functioning, and shows the potential clinical implications related to its consumption. Full article

(This article belongs to the Special Issue Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function)

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Novelties in Carotenoid Chemistry: From Isolation and Synthesis to Properties, Structural Elucidation and Function

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