Biological activities of lignans and stilbenoids associated with plant-insect chemical interactions

Harmatha, Juraj; Dinan, Laurence

doi:10.1023/b:phyt.0000045494.98645.a3

Cited by 140 publications

(71 citation statements)

References 55 publications

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“…For example, the lignan pinoresinol has been described to have antioxidant activity Leu et al, 2011), to act as an antifungal agent (Hwang et al, 2010), to exert cytotoxicity (Menendez et al, 2008), or to delay molting and induce mortality in insects (Cabral et al, 1999). Most of the evidence for an involvement of lignans in plant defense against insects arises from the testing of how compounds isolated from plant species that are resistant to particular insect pests deter feeding (Harmatha and Dinan, 2003). It is likely that the reported differences between the effects of lignans and neolignans are due not only to their structural specificities but also to their redox state.…”

Section: Introductionmentioning

confidence: 99%

Phenylcoumaran Benzylic Ether Reductase Prevents Accumulation of Compounds Formed under Oxidative Conditions in Poplar Xylem

et al. 2014

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Phenylcoumaran benzylic ether reductase (PCBER) is one of the most abundant proteins in poplar (Populus spp) xylem, but its biological role has remained obscure. In this work, metabolite profiling of transgenic poplar trees downregulated in PCBER revealed both the in vivo substrate and product of PCBER. Based on mass spectrometry and NMR data, the substrate was identified as a hexosylated 8-5-coupling product between sinapyl alcohol and guaiacylglycerol, and the product was identified as its benzyl-reduced form. This activity was confirmed in vitro using a purified recombinant PCBER expressed in Escherichia coli. Assays performed on 20 synthetic substrate analogs revealed the enzyme specificity. In addition, the xylem of PCBER-downregulated trees accumulated over 2000-fold higher levels of cysteine adducts of monolignol dimers. These compounds could be generated in vitro by simple oxidative coupling assays involving monolignols and cysteine. Altogether, our data suggest that the function of PCBER is to reduce phenylpropanoid dimers in planta to form antioxidants that protect the plant against oxidative damage. In addition to describing the catalytic activity of one of the most abundant enzymes in wood, we provide experimental evidence for the antioxidant role of a phenylpropanoid coupling product in planta.

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Section: Introductionmentioning

confidence: 99%

Phenylcoumaran Benzylic Ether Reductase Prevents Accumulation of Compounds Formed under Oxidative Conditions in Poplar Xylem

et al. 2014

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“…For example, lignans with various O-methylation (methoxylation) patterns are distributed widely in the plant kingdom (Umezawa 2003a(Umezawa , 2003b. These methoxylated lignans have bioactivities that are useful for human health and play important physiological roles in plant metabolism (Harmatha and Dinan 2003;MacRae and Towers 1984;Umezawa 2003a).…”

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confidence: 99%

A lignan O-methyltransferase catalyzing the regioselective methylation of matairesinol in Carthamus tinctorius

Umezawa

Ragamustari

Nakatsubo

et al. 2013

Plant Biotechnology

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Lignans are a group of plant phenolic compounds with various biological activities, including antitumor and antioxidant properties. O-Methylation is a critical step in biosynthesis of these compounds. However, little is known about the O-methyltransferase (OMT) enzymes that catalyze lignan O-methylation. We discovered a highly regioselective OMT activity in safflower (Carthamus tinctorius) seeds that catalyzed the methylation of matairesinol, a dibenzylbutyrolactone lignan, into 4′-O-methylmatairesinol (arctigenin) but not 4-O-methylmatairesinol (isoarctigenin). By examining such OMT activity in correlation with OMT transcript abundances during seed development, we cloned a few putative OMT cDNAs and produced their recombinant proteins in Escherichia coli. Among them, one protein exhibited O-methylation activity for matairesinol with the regioselectivity identical to that of the plant protein, and was named C. tinctorius matairesinol OMT (CtMROMT). CtMROMT did not show any detectable OMT activities towards phenylpropanoid monomers under the reaction conditions tested, while it methylated flavonoid apigenin efficiently into 4′-O-methylapigenin (acacetin). However, quantitative real-time polymerase chain reaction analysis demonstrated that expression of the CtMROMT gene was synchronized with the CtMROMT activity profile and arctigenin accumulation in the plant. These results demonstrated that CtMROMT is a novel plant OMT for lignan methylation.

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“…As lignanas são metabólitos secundários que desempenham um papel importante na defesa das plantas contra insetos, 22,[53][54][55] embora o modo de ação destes compostos seja desconhecido, 55 eles podem atuar em grande parte como reguladores de alimentação dos insetos, mas em alguns casos, podem também influenciar as funções fisiológicas específicas destes.…”

Section: Funções Biológicas Da (-)-Cubebina Nas Plantasunclassified

Cubebin: A Small Molecule with Great Potential

Pissurno

Laurentiz²

2017

Rev. Virtual Quim.

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Abstract:The (-)-cubebin is a lignan dibenzylbutyrolactolic of occurrence in various species of plants, especially in the genus Piper. Although it has been known for over 150 years, the last few decades the biological properties of this molecule has attracted the attention of several research groups. Recent publications obtained from Scopus bases, SciFinder and PubMed database have highlighted the numerous biological activities attributed to cubebin, as trypanocidal activity, shistomicida, cytotoxicity on cancer lines, vasodilator, antihistaminic, and anti-inflammatory. These studies demonstrate the pharmacological potential of cubebin and its importance as starting material to obtain even more potent derivatives.

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Biological activities of lignans and stilbenoids associated with plant-insect chemical interactions

Cited by 140 publications

References 55 publications

Phenylcoumaran Benzylic Ether Reductase Prevents Accumulation of Compounds Formed under Oxidative Conditions in Poplar Xylem

Phenylcoumaran Benzylic Ether Reductase Prevents Accumulation of Compounds Formed under Oxidative Conditions in Poplar Xylem

A lignan O-methyltransferase catalyzing the regioselective methylation of matairesinol in Carthamus tinctorius

Cubebin: A Small Molecule with Great Potential

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