Antioxidation reaction mechanism studies of phenolic lignans, identification of antioxidation products of secoisolariciresinol from lipid oxidation

Masuda, Toshiya; Akiyama, Jun; Fujimoto, Aya; Yamauchi, Satoshi; Maekawa, Tomomi; Sone, Yoshitsugu

doi:10.1016/j.foodchem.2010.04.065

Cited by 43 publications

(30 citation statements)

References 31 publications

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“…Lignans represent an abundant and widespread group of compounds demonstrating a wide range of biological activities, such as anticancer (review by Landete 2012), antimicrobial, anti-inflammatory (Küpeli et al 2003;During et al 2012), hypoglycemic (Banskota et al 2006; reviews by: Erdemoglu et al 2004;Saleem et al 2005;Topcu and Demirkiran 2007;Dar and Arumugam 2013), antioxidant (Masuda et al 2010), cardioprotective (Zanwar et al 2011) and anti-osteoporotic (Yin et al 2006). Lignan food ingredients such as secoisolariciresinol, matairesinol, lariciresinol and pinoresinol are conversed by intestinal bacteria to enterolignans: enterodiol and enterolactone and were reported to reduce the risk of some cancers and cardiovascular diseases (Milder et al 2007;Ghisalberti 1997;Landete 2012) and exhibited estrogen activity (Cassidy et al 2000;Aehle et al 2011).…”

Section: Introductionmentioning

confidence: 99%

Lignan accumulation in two-phase cultures of Taxus x media hairy roots

Sykłowska-Baranek

Łysik

Jeziorek

et al. 2018

Plant Cell Tiss Organ Cult

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The biosynthetic potential for six lignans accumulation in two lines of Taxus x media hairy roots was investigated. The cultures of KT and ATMA hairy root lines were supplemented with precursors: coniferyl alcohol (CA 1, 10 or 100 µM) and/or l-phenylalanine (100 µM PHEN) and/or methyl jasmonate (100 µM MeJa). Moreover the two-phase in vitro cultures supported with perfluorodecalin (PFD) as a gas carrier and in situ extrahent were used. The hairy root lines differed in lignan production profiles. In the control untreated cultures KT roots did not accumulate secoisolariciresinol and lariciresinol while ATMA roots did not accumulate matairesinol. In ATMA roots the treatment with CA (1 or 10 µM) resulted in the production of lariciresinol and secoisolariciresinol whereas solely lariciresinol was present after 100 µM CA application. Elicitation with 1 µM CA and MeJa yielded with hydroxymatairesinol aglyca and lariciresinol glucosides with their highest content 37.88 and 3.19 µg/g DW, respectively. The stimulatory effect of simultaneous treatment with 1 µM CA, PHEN and MeJa on lignan production was observed when the cultures were supplemented with PFD-aerated or degassed. In ATMA root cultures these applied conditions were the most favourable for matairesinol content which amounted to 199.86 and 160.25 µg/g DW in PFD-aerated and PFD-degassed supported cultures, respectively. In KT root cultures solely, hydroxymatairesinol and coniferin/CA content was enhanced with their highest yield 59.29 and 134.60 µg/g DW in PFD-aerated and PFD-degassed cultures, respectively.

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Section: Introductionmentioning

confidence: 99%

Lignan accumulation in two-phase cultures of Taxus x media hairy roots

Sykłowska-Baranek

Łysik

Jeziorek

et al. 2018

Plant Cell Tiss Organ Cult

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“…It was found that the differences of the The OH configurations of two stereogenic centers in 1 and 2 were determined by comparison with the 13 C NMR data of the structural similar compounds, erythro-and threo-honokitriol 16 and erythro-and threo-1-C-syringylglycerol. 17 The difference of 13 C NMR chemical shifts of C-7 (δ C 76.0) and C-8 (δ C 76.2) in erythro-honokitriol is δ C-8-C-7 0.2, which is smaller than that in threo-honokitriol ( δ C-8(77.8)-C-7(74.6) 3.2). 16 In addition, the difference of 13 C NMR chemical shifts of C-7 (δ C 74.1) and C-8 (δ C 75.3) in erythro-1-C-syringylglycerol is δ C-8-C-7 1.2, which is also smaller than that in its threo-isomer ( δ C-8(75.8)-C-7(72.9) 2.9).…”

Section: Resultsmentioning

confidence: 99%

“…17 The difference of 13 C NMR chemical shifts of C-7 (δ C 76.0) and C-8 (δ C 76.2) in erythro-honokitriol is δ C-8-C-7 0.2, which is smaller than that in threo-honokitriol ( δ C-8(77.8)-C-7(74.6) 3.2). 16 In addition, the difference of 13 C NMR chemical shifts of C-7 (δ C 74.1) and C-8 (δ C 75.3) in erythro-1-C-syringylglycerol is δ C-8-C-7 1.2, which is also smaller than that in its threo-isomer ( δ C-8(75.8)-C-7(72.9) 2.9). 17 Therefore，the relative configurations of 1 and 2 could also be determined base on the rules as mentioned in the above cases.…”

Section: Resultsmentioning

confidence: 99%

“…et Wils, a plant widely distributed in the west of China and being partly used as a substitute of M. officinalis in Yunnan and Sichuan provinces of China. 4,10 As a result, two new neolignans, manneoinsigins A (1) and B (2), together with other four known lignans, scaphopetalone (3), 11 mesosecoisolariciresinol (4), 12 lariciresinol (5) 13 and evafolin B (6), 14 were isolated. Herein, the isolation, structural elucidation, and their cytotoxic activity are described.…”

Section: Introductionmentioning

confidence: 99%

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Two new neolignans from Manglietia insignis

Shang

Yan

Zhang

et al. 2012

Nat. Prod. Bioprospect.

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Two new neolignans, manneoinsigins A (1) and B (2), together with four known lignans, were isolated from the leaves and stems of Manglietia insignis. The new compounds were established on the basis of extensive spectroscopic analyses. All compounds except 2 were tested for their cytotoxic activity. Compound 3 showed weak cytotoxic activity against the HL-60 human tumor cell line with the IC 50 value of 23.5 μM.

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“…This process should be chemically influenced by the surrounding reactive molecules present in foods. 3) We have reported that many antioxidative polyphenols reacted with a thiol compound, which can influence both nucleophilic and radical reactions, under radical oxidation conditions. 4) We have also revealed that this polyphenol-thiol coupling reaction was faster than thiol oxidation itself.…”

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confidence: 99%

Enhancing Effect of a Cysteinyl Thiol on the Antioxidant Activity of Flavonoids and Identification of the Antioxidative Thiol Adducts of Myricetin

Masuda

Miura

Inai

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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The enhancing effect of a cysteinyl thiol N-benzoylcysteine methyl ester on the antioxidant activity of several flavonoids was investigated in a lipid oxidation system. Obvious enhancement was apparent for catechin, myricetin, quercetin, and taxifolin, the activity for myricetin being the most potent among them. An HPLC analysis of the products from the antioxidation reaction of myricetin in the presence of the thiol was carried out and the structures of the products were determined to clarify the enhancing effect chemically. The obtained data indicated that two thiol adducts on the B ring, and probably C-ring adducts, which were produced in the antioxidation process, exerted an enhancing effect on the antioxidant activity of myricetin.

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Antioxidation reaction mechanism studies of phenolic lignans, identification of antioxidation products of secoisolariciresinol from lipid oxidation

Cited by 43 publications

References 31 publications

Lignan accumulation in two-phase cultures of Taxus x media hairy roots

Lignan accumulation in two-phase cultures of Taxus x media hairy roots

Two new neolignans from Manglietia insignis

Enhancing Effect of a Cysteinyl Thiol on the Antioxidant Activity of Flavonoids and Identification of the Antioxidative Thiol Adducts of Myricetin

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