Isolation, purification and identification of etiolation substrate from fresh-cut Chinese water-chestnut (Eleocharis tuberosa)

Yingjie, Pan; Yixiao, Li; Yuan, Mengqi

doi:10.1016/j.foodchem.2015.03.070

Cited by 48 publications

(34 citation statements)

References 33 publications

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“…Similarly, we identified 3′,4′,5,7-tetrahydroxyflavanone as a 3′-OH hydroxylated derivative of naringenin, which is known as eriodictyol. The NMR data were consistent with the previously published results [ 38 ].…”

Section: Resultssupporting

confidence: 92%

Hydroxylation of diverse flavonoids by CYP450 BM3 variants: biosynthesis of eriodictyol from naringenin in whole cells and its biological activities

et al. 2016

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BackgroundCytochrome P450 monooxygenase constitutes a significant group of oxidative enzymes that can introduce an oxygen atom in a high regio- and stereo-selectivity mode. We used the Bacillus megaterium cytochrome P450 BM3 (CYP450 BM3) and its variants namely mutant 13 (M13) and mutant 15 (M15) for the hydroxylation of diverse class of flavonoids.ResultsAmong 20 flavonoids, maximum seven flavonoids were hydroxylated by the variants while none of these molecules were accepted by CYP450 BM3 in in vitro reaction. Moreover, M13 exhibited higher conversion of substrates than M15 and CYP450 BM3 enzymes. We found that M13 carried out regiospecific 3ʹ-hydroxylation reaction of naringenin with the highest conversion among all the tested flavonoids. The apparent Km and kcat values of M13 for naringenin were 446 µM and 1.955 s−1, respectively. In whole-cell biotransformation experiment with 100 µM of naringenin in M9 minimal medium with 2 % glucose in shake flask culture, M13 showed 2.14- and 13.96-folds higher conversion yield in comparison with M15 (16.11 %) and wild type (2.47 %). The yield of eriodictyol was 46.95 µM [~40.7 mg (13.5 mg/L)] in a 3-L volume lab scale fermentor at 48 h in the same medium exhibiting approximately 49.81 % conversion of the substrate. In addition, eriodictyol exhibited higher antibacterial and anticancer potential than naringenin, flavanone and hesperetin.ConclusionsWe elucidated that eriodictyol being produced from naringenin using recombinant CYP450 BM3 and its variants from B. megaterium, which shows an approach for the production of important hydroxylated compounds of various polyphenols that may span pharmaceutical industries.Electronic supplementary materialThe online version of this article (doi:10.1186/s12934-016-0533-4) contains supplementary material, which is available to authorized users.

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Section: Resultssupporting

confidence: 92%

Hydroxylation of diverse flavonoids by CYP450 BM3 variants: biosynthesis of eriodictyol from naringenin in whole cells and its biological activities

et al. 2016

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“…Thus, further purification was focused on the two flavonoids-enriched fractions (C and D). The isolated compounds ( Fig.1) included quercetin (1) [16], isorhamnetin 3-O-b-D-glucoside (2) [17], eriodictyol (3) [18], pyracanthoside (4) [19], apigenin (5) [20], apigetrin (6) [20], acacetin (7) [21], acacipetalin (8) [21], luteolin (9) [16], diosmetin (10) [22], spinacetin (11) [16], axillarin (12) [16], bonanzin (13) [23], cirsiliol (14) [24], chrysosplenol D (15) [25] and artemetin (16) [23], and were characterized by detailed spectroscopic analysis and comparing with the previous literature data. Among them, compounds 11-16 have never been reported from Chrsanthemum species before, and 14 compounds (1-3, 5-7, 9-16) were isolated from Chuju for the first time.…”

Section: Bioassay Guided Isolation and Structural Identification Of Fmentioning

confidence: 99%

Antioxidant and Anti-Inflammatory Flavonoids from the Flowers of Chuju, a Medical Cultivar of Chrysanthemum Morifolim Ramat

et al. 2018

J. Mex. Chem. Soc.

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Chuju, the flower of Chrysanthemum morifolim cv. Chuju, is a traditional medicine-food material used in China. Bioassay-guided chemical investigation on Chuju led the isolation of 16 flavonoids (1-16) characterized as quercetin (1), isorhamnetin 3-O-β-D-glucoside (2), eriodictyol (3), pyracanthoside (4), apigenin (5), apigetrin (6), acacetin (7), acacipetalin (8), luteolin (9), diosmetin (10), spinacetin (11), axillarin (12), bonanzin (13), cirsiliol (14), chrysosplenol D (15) and artemetin (16). Among them, compounds (11-16) were first reported from the Chrysanthemum species. Chuju flavonoids displayed strong antioxidant in DPPH (1, 1-diphenyl-2- picrylhydrazyl) radical scavenging assay, and high anti-inflammatory activity by inhibiting NO production in LPS-induced RAW 264.7 cells. These findings suggests that Chuju is an ideal source of natural flavonoids with significant antioxidant and anti-inflammatory effects, and is worthy of further development as health-promoting food or supplement.

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“…Some treatments such as citric acid (Jiang et al, 2004), salicylic acid (Peng & Jiang, 2006) and hydrogen peroxide (Peng et al, 2008) could inhibit fresh-cut CWC browning. Pan et al (2015) investigated the browning products and identified some substrates such as eriodictyol, naringenin, sucrose and ethyl D -glucoside in fresh-cut CWC. However, chemical preservation easily leads to the formation of toxic substances.…”

Section: Introductionmentioning

confidence: 99%

Study on the browning and structure properties of fresh-cut Chinese water chestnut ( Eleocharis tuberosa)

2019

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On this paper, the microstructure, water properties and browning control of Chinese water chestnut (CWC) after harvest were studied. Results showed that the tuber cell contained a large number of starch granules (5-10 μm for each one). The water-holding capacity of tuber cell was weak and T2 relaxation time was 28.5-75.6 ms. Sucrose was the main sugar component in Chinese water chestnut, which account for 84.8% of total sugar. On addition, potassium sorbate, green tea polyphenol and chitosan decreased the browning of fresh-cut CWC compared with the other anti-browning agents such as acetic acid, citric acid, oxalic acid, vitamin C and thyme oil. Moreover, chitosan coating combined with potassium sorbate and green tea polyphenol delayed weight loss and decay of fresh-cut tubers, also maintained a higher soluble solids and ascorbic acid content. The study provided an alternative method for controlling CWC browning, which would be helpful for the application of anti-browning agents in CWC processing.Practical Application: Provide a better understanding in the texture and anti-browning agents of Chinese water chestnut.

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Isolation, purification and identification of etiolation substrate from fresh-cut Chinese water-chestnut (Eleocharis tuberosa)

Cited by 48 publications

References 33 publications

Hydroxylation of diverse flavonoids by CYP450 BM3 variants: biosynthesis of eriodictyol from naringenin in whole cells and its biological activities

Hydroxylation of diverse flavonoids by CYP450 BM3 variants: biosynthesis of eriodictyol from naringenin in whole cells and its biological activities

Antioxidant and Anti-Inflammatory Flavonoids from the Flowers of Chuju, a Medical Cultivar of Chrysanthemum Morifolim Ramat

Study on the browning and structure properties of fresh-cut Chinese water chestnut ( Eleocharis tuberosa)

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