pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives

Nakagawa, Souichi; Tachrim, Zetryana Puteri; Kurokawa, Natsumi; Ohashi, Fumina; Sakihama, Yasuko; Suzuki, Takayoshi; Hashidoko, Yasuyuki; Hashimoto, Makoto

doi:10.3390/molecules23081943

Cited by 12 publications

(10 citation statements)

References 12 publications

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“…The proton in the dihydroindolic ring is the most acidic. The quaternary nitrogen of the indoline moiety has little influence on the antioxidant activity of this compound . The study also reports a descending order of deprotonation of betacyanins (based on betanin and betanidin) as C-17, C-15, and C-2.…”

Section: Results and Discussionmentioning

confidence: 77%

“…The quaternary nitrogen of the indoline moiety has little influence on the antioxidant activity of this compound. 65 The study also reports a descending order of deprotonation of betacyanins (based on betanin and betanidin) as C-17, C-15, and C-2. These properties were determined from theoretical models.…”

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 93%

“…This effort led to the narrowing of the temperature range to 65−75 °C, a significantly lower value compared to the typical 85 °C often utilized in recent experiments on betanin and gomphrenin degradation. 48,54 Figures 5 and S6 depict the influence of applying different gomphrenin concentrations (15, 30, and 60 μM) and temperatures (65,70, and 75 °C) on the generation of its decarboxylated derivatives 2, 4, and 5 in extract B2. For a convenient comparison and assessment of generation efficiency, the signals obtained for lower concentrations (15 and 30 μM) were multiplied by the factors of 4 and 2, respectively, in Figures 5 and S8A,B.…”

Section: Methods For Generation Of Decarboxylated Gomphrenins For Bio...mentioning

confidence: 99%

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Basella alba L. (Malabar Spinach) as an Abundant Source of Betacyanins: Identification, Stability, and Bioactivity Studies on Natural and Processed Fruit Pigments

Sutor-Świeży,

Górska,

Kumorkiewicz-Jamro

et al. 2024

J. Agric. Food Chem.

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The antioxidant and anti-inflammatory activities of acylated and decarboxylated gomphrenins, as well as Basella alba L. fruit extract, were investigated in relation to gomphrenin, known for its high biological potential. The most abundant natural acylated gomphrenins, namely, 6′-O-E-caffeoyl-gomphrenin (malabarin) and 6′-O-E-4-coumaroyl-gomphrenin (globosin), were isolated from B. alba extract for the studies. In addition, controlled thermal decarboxylation of gomphrenin in the purified B. alba extract at 65−75 °C resulted in the formation of the most prevalent decarboxylated products, including 17-decarboxy-gomphrenin and 2,17-bidecarboxy-gomphrenin, along with their isoforms. The structures of the decarboxylated pigments were confirmed by NMR analyses. Exploring the matrix effect on pigment reactivity revealed a tremendous increase in the stability of all betacyanins after the initial stage of extract purification using a cation exchanger under various conditions. This indicates the removal of a substantial portion of the unfavorable matrix from the extract, which presumably contains reactive species that could otherwise degrade the pigments. Furthermore, the high concentration of citrates played a significant role in favoring the formation of 2decarboxy-gomphrenin to a considerable extent. In vitro screening experiments revealed that the tested compounds demonstrated strong anti-inflammatory properties in lipopolysaccharide (LPS)-activated human macrophages. This effect encompassed the selective inhibition of cytokine and chemokine release from activated macrophages, modulation of the chemotactic activity of immune cells, and the regulation of tissue remodeling mediators' release.

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Section: Results and Discussionmentioning

confidence: 77%

Section: Journal Of Agricultural and Food Chemistrymentioning

confidence: 93%

Section: Methods For Generation Of Decarboxylated Gomphrenins For Bio...mentioning

confidence: 99%

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Basella alba L. (Malabar Spinach) as an Abundant Source of Betacyanins: Identification, Stability, and Bioactivity Studies on Natural and Processed Fruit Pigments

Sutor-Świeży,

Górska,

Kumorkiewicz-Jamro

et al. 2024

J. Agric. Food Chem.

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“…Sulfamethazine has also been reported as an antimicrobial compound [ 30 ]. On the other hand, cyclo -Dopa 5- O -glucoside may act as a ROS scavenger [ 31 ]. DIMBOA-glucoside is likely related to defense signaling [ 32 ].…”

Section: Resultsmentioning

confidence: 99%

Nicotinamide Effectively Suppresses Fusarium Head Blight in Wheat Plants

Sidiq

Mori

Yaeno

et al. 2021

IJMS

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Pyridine nucleotides such as a nicotinamide adenine dinucleotide (NAD) are known as plant defense activators. We previously reported that nicotinamide mononucleotide (NMN) enhanced disease resistance against fungal pathogen Fusarium graminearum in barley and Arabidopsis. In this study, we reveal that the pretreatment of nicotinamide (NIM), which does not contain nucleotides, effectively suppresses disease development of Fusarium Head Blight (FHB) in wheat plants. Correspondingly, deoxynivalenol (DON) mycotoxin accumulation was also significantly decreased by NIM pretreatment. A metabolome analysis showed that several antioxidant and antifungal compounds such as trigonelline were significantly accumulated in the NIM-pretreated spikes after inoculation of F. graminearum. In addition, some metabolites involved in the DNA hypomethylation were accumulated in the NIM-pretreated spikes. On the other hand, fungal metabolites DON and ergosterol peroxide were significantly reduced by the NIM pretreatment. Since NIM is relative stable and inexpensive compared with NMN and NAD, it may be more useful for the control of symptoms of FHB and DON accumulation in wheat and other crops.

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“…Degradation products and degradation pathways of betanin have been identified [ 28 , 29 ], and generally, degradation of betanin proceeds through degradation into betalamic acid and cyclo-dopa 5-O-glycoside by cleavage of the aldimine bond. An antioxidant capacity of these compounds: betalamic acid [ 30 ] and cyclo-dopa derivatives [ 31 ] has been reported, allowing the suggestion that the degradation products like these compounds may be involved in the antioxidant capacity of betanin after heat degradation.…”

Section: Discussionmentioning

confidence: 99%

Effects of heat degradation of betanin in red beetroot (Beta vulgaris L.) on biological activity and antioxidant capacity

et al. 2023

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Betanin is a red pigment of red beetroot (Beta vulgaris L.), providing the beneficial effects to maintain human health. Betanin is involved in the characteristic red color of red beetroot, and used as an edible dye. Betanin is known to be a highly unstable pigment, and water solutions of betanin are nearly fully degraded after heating at 99°C for 60 min in the experimental conditions of this study. The present study investigated the effects of red beetroot juice (RBJ) and betanin on immune cells, and found that stimulation with RBJ and betanin induces interleukin (IL)-1β, IL-8, and IL-10 mRNA in a human monocyte derived cell line, THP-1 cells. This mRNA induction after stimulation with RBJ and betanin was not significantly changed after heat treatment when attempting to induce degradation of the betanin. Following these results, the effects of heat degradation of betanin on the inhibition of lipopolysaccharide (LPS) induced nitric oxide (NO) production in RAW264 cells and the antioxidant capacity were investigated. The results showed that the inhibition activity of RBJ and betanin with the LPS induced NO production is not altered after heat degradation of betanin. In addition, the results of FRAP (ferric reducing antioxidant power) and DPPH (1,1-Diphenyl-2-picrylhydrazyl) assays indicate that a not inconsiderable degree of the antioxidant capacity of RBJ and betanin remained after heat degradation of betanin. These results suggest that it is important to consider the effects of degradation products of betanin in the evaluation of the beneficial effects of red beetroot on health.

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pH Stability and Antioxidant Power of CycloDOPA and Its Derivatives

Cited by 12 publications

References 12 publications

Basella alba L. (Malabar Spinach) as an Abundant Source of Betacyanins: Identification, Stability, and Bioactivity Studies on Natural and Processed Fruit Pigments

Basella alba L. (Malabar Spinach) as an Abundant Source of Betacyanins: Identification, Stability, and Bioactivity Studies on Natural and Processed Fruit Pigments

Nicotinamide Effectively Suppresses Fusarium Head Blight in Wheat Plants

Effects of heat degradation of betanin in red beetroot (Beta vulgaris L.) on biological activity and antioxidant capacity

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