Implications of Fagopyrin Formation In Vitro by UV Spectroscopic Analysis

Kosyan, Anatolij; Sytar, Oksana

doi:10.3390/molecules26072013

Cited by 9 publications

(8 citation statements)

References 37 publications

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“…The shape of the orbitals involved in UV-VIS transitions for fagopyrin F conformers except the presented in the text (Figure 12) is shown in Supplementary Materials. A comparison of calculated fagopyrin F and experimental spectra [19] for the plant material suggests that in the plant material, many fagopyrin structures may be present. It is not clear which version of fagopyrin in the experimental spectra was registered; how- A comparison of calculated fagopyrin F and experimental spectra [19] for the plant material suggests that in the plant material, many fagopyrin structures may be present.…”

Section: Uv-vis Spectra Of Fagopyrin Conformersmentioning

confidence: 99%

“…A comparison of calculated fagopyrin F and experimental spectra [19] for the plant material suggests that in the plant material, many fagopyrin structures may be present. It is not clear which version of fagopyrin in the experimental spectra was registered; how- A comparison of calculated fagopyrin F and experimental spectra [19] for the plant material suggests that in the plant material, many fagopyrin structures may be present. It is not clear which version of fagopyrin in the experimental spectra was registered; however, in the experimental spectra, the most intensive theoretically calculated bands are visible.…”

Section: Uv-vis Spectra Of Fagopyrin Conformersmentioning

confidence: 99%

“…The interest in fagopyrins is mainly due to their spectroscopic properties. They exhibit absorption of electromagnetic radiation in the wavelength range of the light around λ max 550 and 590 nm [15,19,20]. Upon excitation, they are able to transfer energy to the oxygen molecule, thereby producing reactive oxygen species (ROS) [21].…”

Section: Introductionmentioning

confidence: 99%

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Theoretical Studies on the Structure and Intramolecular Interactions of Fagopyrins—Natural Photosensitizers of Fagopyrum

Szymański

Majerz

2022

Molecules

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Compounds characterized by a double-anthrone moiety are found in many plant species. One of them are fagopyrins—naturally occurring photosensitizers of Fagopyrum. The photosensitizing properties of fagopyrins are related to the selective absorption of light, which is a direct result of their spatial and electronic structure and many intramolecular interactions. The nature of the interactions varies in different parts of the molecule. The aim of this study is to determine the structure and intramolecular interactions of fagopyrin molecules. For this purpose, in silico calculations were used to perform geometry optimization in the gas phase. QTAIM and NCI analysis suggest the formation of the possible conformers in the fagopyrin molecules. The presence of a strong OHO hydrogen bond was shown in the anthrone moiety of fagopyrin. The minimum energy difference for selected conformers of fagopyrins was 1.1 kcal∙mol−1, which suggested that the fagopyrin structure may exist in a different conformation in plant material. Similar interactions were observed in previously studied structures of hypericin and sennidin; however, only fagopyrin showed the possibility of brake the strong OHO hydrogen bond in favor of forming a new OHN hydrogen bond.

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Section: Uv-vis Spectra Of Fagopyrin Conformersmentioning

confidence: 99%

Section: Uv-vis Spectra Of Fagopyrin Conformersmentioning

confidence: 99%

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Theoretical Studies on the Structure and Intramolecular Interactions of Fagopyrins—Natural Photosensitizers of Fagopyrum

Szymański

Majerz

2022

Molecules

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“…Cultures in suspensions with identical initial density (OD600) were allowed to grow for 3 h (doubling time 1.5 h) after addition of photosensitizers: ( a ) Effect of fagopyrin (C40H34N2O8); ( b ) Effect of hypericin (C30H16O8). Of note, the similarity and the differences of the two structures: both compounds contain a naphthodianthrone skeleton, but fagopyrin has two piperidines, which are not present in hypericin [ 29 ].…”

Section: Figurementioning

confidence: 99%

The Effects of Photosensitizing Dyes Fagopyrin and Hypericin on Planktonic Growth and Multicellular Life in Budding Yeast

et al. 2021

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Naphthodianthrones such as fagopyrin and hypericin found mainly in buckwheat (Fagopyrum spp.) and St. John’s wort (SJW) (Hypericum perforatum L.) are natural photosensitizers inside the cell. The effect of photosensitizers was studied under dark conditions on growth, morphogenesis and induction of death in Saccharomyces cerevisiae. Fagopyrin and hypericin induced a biphasic and triphasic dose response in cellular growth, respectively, over a 10-fold concentration change. In fagopyrin-treated cells, disruptions in the normal cell cycle progression were evident by microscopy. DAPI staining revealed several cells that underwent premature mitosis without budding, a striking morphological abnormality. Flow Cytometric (FC) analysis using a concentration of 100 µM showed reduced cell viability by 41% in fagopyrin-treated cells and by 15% in hypericin-treated cells. FC revealed the development of a secondary population of G1 cells in photosensitizer-treated cultures characterized by small size and dense structures. Further, we show that fagopyrin and the closely related hypericin altered the shape and the associated fluorescence of biofilm-like structures. Colonies grown on solid medium containing photosensitizer had restricted growth, while cell-to-cell adherence within the colony was also affected. In conclusion, the photosensitizers under dark conditions affected culture growth, caused toxicity, and disrupted multicellular growth, albeit with different efficiencies.

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“…The novel method of identification for the specific secondary metabolite nathodianthrone fagopyrin is presented [ 13 ], together with a study on the role of nathodyanthrones fagopyrin and hypericin on planktonic growth and multicellular life in budding yeast [ 14 ]. The present data show that fagopyrin and hypericin uptake by the S. cerevisiae cells interfered with their biology both in planktonic and biofilm-like growth and accumulated in organelles and near the nucleus.…”

mentioning

confidence: 99%