Oenin/Syringic Acid Copigmentation: Insights From a Theoretical Study

Li, Yunkui; Prejanò, Mario; Toscano, Marirosa; Russo, Nino

doi:10.3389/fchem.2019.00579

Cited by 13 publications

(3 citation statements)

References 58 publications

(132 reference statements)

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“…These observations need further targeted studies for a better understanding of the co-pigmentation of these compounds in pitaya fruit. An early understanding could be generated by computational models based on the dispersion-corrected density functional theory [ 50 ].…”

Section: Discussionmentioning

confidence: 99%

Combined Transcriptome and Metabolome analysis of Pitaya fruit unveiled the mechanisms underlying Peel and pulp color formation

et al. 2020

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Background Elucidating the candidate genes and key metabolites responsible for pulp and peel coloration is essential for breeding pitaya fruit with new and improved appeal and high nutritional value. Here, we used transcriptome (RNA-Seq) and metabolome analysis (UPLC-MS/MS) to identify structural and regulatory genes and key metabolites associated with peel and pulp colors in three pitaya fruit types belonging to two different Hylocereus species. Result Our combined transcriptome and metabolome analyses suggest that the main strategy for obtaining red color is to increase tyrosine content for downstream steps in the betalain pathway. The upregulation of CYP76ADs is proposed as the color-breaking step leading to red or colorless pulp under the regulation by WRKY44 transcription factor. Supported by the differential accumulation of anthocyanin metabolites in red pulped pitaya fruit, our results showed the regulation of anthocyanin biosynthesis pathway in addition to betalain biosynthesis. However, no color-breaking step for the development of anthocyanins in red pulp was observed and no biosynthesis of anthocyanins in white pulp was found. Together, we propose that red pitaya pulp color is under the strict regulation of CYP76ADs by WRKYs and the anthocyanin coexistence with betalains is unneglectable. We ruled out the possibility of yellow peel color formation due to anthocyanins because of no differential regulation of chalcone synthase genes between yellow and green and no detection of naringenin chalcone in the metabolome. Similarly, the no differential regulation of key genes in the carotenoid pathway controlling yellow pigments proposed that the carotenoid pathway is not involved in yellow peel color formation. Conclusions Together, our results propose several candidate genes and metabolites controlling a single horticultural attribute i.e. color formation for further functional characterization. This study presents useful genomic resources and information for breeding pitaya fruit with commercially attractive peel and pulp colors. These findings will greatly complement the existing knowledge on the biosynthesis of natural pigments for their applications in food and health industry.

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Section: Discussionmentioning

confidence: 99%

Combined Transcriptome and Metabolome analysis of Pitaya fruit unveiled the mechanisms underlying Peel and pulp color formation

et al. 2020

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“…All QM calculations were performed using Gaussian 09 and UltraEdit 26 software, and the procedure was based on the following strategy to analyze the optimal geometries and single-site energy of terpenes. , This strategy used the hybrid exchange–correlation functional B3LYP and the Grimme dispersion correction with the 6-31+G(d) basis set to obtain the optimal geometries and vibrational frequencies of the terpenes, thus confirming the potential surface minima and obtaining a corrected value for the thermodynamic calculation. Integral equation formalism of the polarizable continuum model was used to account for the solvent effect.…”

Section: Methodsmentioning

confidence: 99%

Molecular Rearrangement of Four Typical Grape Free Terpenes in the Wine Environment

Frank

Wei

et al. 2023

J. Agric. Food Chem.

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In order to analyze the molecular rearrangement of terpenes in wine during aging, the changes in linalool, α-terpineol, nerol, and geraniol in model wine were investigated in the dark at low temperature for 90 days. Headspace-gas chromatograph−mass spectrometer/olfactometry was used for qualitative and relative quantitation of terpenes. Quantum mechanical calculation was used to analyze the Gibbs free energy. The results showed that nerol was converted into D-limonene, terpinolene, linalool, and α-terpineol. Geraniol was converted into β-ocimene, terpinolene, and linalool. Linalool was converted into terpinolene. The conversion rate of nerol to terpinolene was the highest with 5.94%. α-Terpineol was not converted spontaneously into other terpenes due to its lowest Gibbs free energy, indicating that the cyclization and isomerization could occur spontaneously through an exotherm reaction. However, the dehydroxylation of linalool, nerol, and geraniol required an energy source.

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“…The SOCs values, defined as

, were computed by using the atomic-mean field approximation [ 60 ] as implemented in the DALTON code [ 61 ] at the B3LYP/cc-pVDZ level of theory on the previously optimized structures. The accuracy of the chosen protocol was previously adopted to investigate the photophysical properties of several other organic photosensitizers [ 62 , 63 , 64 , 65 , 66 ].…”

Section: Computational Detailsmentioning

confidence: 99%

Sulphur- and Selenium-for-Oxygen Replacement as a Strategy to Obtain Dual Type I/Type II Photosensitizers for Photodynamic Therapy

et al. 2023

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The effect on the photophysical properties of sulfur- and selenium-for-oxygen replacement in the skeleton of the oxo-4-dimethylaminonaphthalimide molecule (DMNP) has been explored at the density functional (DFT) level of theory. Structural parameters, excitation energies, singlet–triplet energy gaps (ΔES-T), and spin–orbit coupling constants (SOC) have been computed. The determined SOCs indicate an enhanced probability of intersystem crossing (ISC) in both the thio- and seleno-derivatives (SDMNP and SeDMNP, respectively) and, consequently, an enhancement of the singlet oxygen quantum yields. Inspection of Type I reactions reveals that the electron transfer mechanisms leading to the generation of superoxide is feasible for all the compounds, suggesting a dual Type I/Type II activity.

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Oenin/Syringic Acid Copigmentation: Insights From a Theoretical Study

Cited by 13 publications

References 58 publications

Combined Transcriptome and Metabolome analysis of Pitaya fruit unveiled the mechanisms underlying Peel and pulp color formation

Combined Transcriptome and Metabolome analysis of Pitaya fruit unveiled the mechanisms underlying Peel and pulp color formation

Molecular Rearrangement of Four Typical Grape Free Terpenes in the Wine Environment

Sulphur- and Selenium-for-Oxygen Replacement as a Strategy to Obtain Dual Type I/Type II Photosensitizers for Photodynamic Therapy

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