An update on bioactive plant lignans

Saleem, Muhammad; Kim, Hyoung Ja; Ali, Muhammad; Lee, Yong Sup

doi:10.1039/b514045p

Cited by 429 publications

(180 citation statements)

References 103 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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confidence: 99%

Stereoselective Synthesis of Highly Substituted Tetrahydrofurans through Diverted Carbene OH Insertion Reaction

et al. 2015

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Abstract:Copper or rhodium catalyzed reaction of diazocarbonyl compounds with β-hydroxyketones gives highly substituted tetrahydrofurans with excellent diastereoselectivity, under mild conditions, in a single step process that starts as a carbene O-H insertion reaction but is diverted by an intramolecular aldol reaction.The tetrahydrofuran ring is a commonly found motif in naturally occurring bioactive compounds, and occurs in structural classes such as lignans, [1] acetogenins, [2] ionophores, [3] and macrolides. [4] Examples include (+)-fragransin A2 [5] and amphidinolide F [6] (Figure 1). As a consequence, a number of strategies have been employed for the stereoselective synthesis of tetrahydrofurans. [7][8][9] However, despite advances in synthetic methodology, highly substituted tetrahydrofurans remain difficult to access, and new approaches are needed. We now describe a new route to highly substituted tetrahydrofurans that proceeds with excellent diastereoselectivity, under mild conditions in a single step (Scheme 1) by a novel process initiated by metallocarbene O-H insertion but diverted by intramolecular aldol reaction.

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“…For example, [2,3]-sigmatropic rearrangements of oxonium ylides (e.g. 163) generated in this manner have been employed for the construction of tetrahydrofuran-3-ones.…”

Section: Metal-catalyzed Addition or Insertion Reactions Of Diazo Commentioning

confidence: 99%