Lignans

Barker, David

doi:10.3390/molecules24071424

Cited by 36 publications

(25 citation statements)

References 20 publications

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“…Lignans are a large group of polyphenols found in plants, particularly in seeds, whole grains, and vegetables [ 22 ]. They are derived from oxidative dimerization of more than two phenylpropanoid units.…”

Section: Discussionmentioning

confidence: 99%

Nordihydroguaiaretic Acid as a Novel Substrate and Inhibitor of Catechol O-Methyltransferase Modulates 4-Hydroxyestradiol-Induced Cyto- and Genotoxicity in MCF-7 Cells

et al. 2021

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Nordihydroguaiaretic acid (NDGA) is a major lignan metabolite found in Larrea spp., which are widely used in South America to treat various diseases. In breast tissue, estradiol is metabolized to the catechol estrogens such as 4-hydroxyestradiol (4-OHE2), which have been proposed to be cancer initiators potentially involved in mammary carcinogenesis. Catechol-O-methyltransferase (COMT) catalyzes the O-methylation of catechol estrogens to their less toxic methoxy derivatives, such as 4-O-methylestradiol (4-MeOE2). The present study investigated the novel biological activities of NDGA in relation to COMT and the effects of COMT inhibition by NDGA on 4-OHE2-induced cyto- and genotoxicity in MCF-7 human breast cancer cells. Two methoxylated metabolites of NDGA, 3-O-methylNDGA (3-MNDGA) and 4-O-methyl NDGA (4-MNDGA), were identified in the reaction mixture containing human recombinant COMT, NDGA, and cofactors. Km values for the COMT-catalyzed metabolism of NDGA were 2.6 µM and 2.2 µM for 3-MNDGA and 4-MNDGA, respectively. The COMT-catalyzed methylation of 4-OHE2 was inhibited by NDGA at an IC50 of 22.4 µM in a mixed-type mode of inhibition by double reciprocal plot analysis. Molecular docking studies predicted that NDGA would adopt a stable conformation at the COMT active site, mainly owing to the hydrogen bond network. NDGA is likely both a substrate for and an inhibitor of COMT. Comet and apurinic/apyrimidinic site quantitation assays, cell death, and apoptosis in MCF-7 cells showed that NDGA decreased COMT-mediated formation of 4-MeOE2 and increased 4-OHE2-induced DNA damage and cytotoxicity. Thus, NDGA has the potential to reduce COMT activity in mammary tissues and prevent the inactivation of mutagenic estradiol metabolites, thereby increasing catechol estrogen-induced genotoxicities.

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Section: Discussionmentioning

confidence: 99%

Nordihydroguaiaretic Acid as a Novel Substrate and Inhibitor of Catechol O-Methyltransferase Modulates 4-Hydroxyestradiol-Induced Cyto- and Genotoxicity in MCF-7 Cells

et al. 2021

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“…(+)-Nyasol exerted antiprotozoal activity against Leishmania major promastigotes. (+)-medioresinol, (+)-pinoresinoland (−)-lirioresinol B showed antileishmanial effect against Leishmania amazonensis amastigotes; veraguensin and grandisin demonstrated trypanosomicidal effect against Trypanosoma cruzi trypomastigotes; anolignan B and termilignan were active against the chloroquine-susceptible strain of Plasmodium falciparum (Barker, 2019). In terms of insecticide activity, sesamin, asarinin, savinin, and hinokinin improved the effects of insecticides.…”

Section: Lignans and Flavonolignansmentioning

confidence: 99%

Evaluation of the status quo of polyphenols analysis: Part I—phytochemistry, bioactivity, interactions, and industrial uses

Sanches-Silva

Reboredo‐Rodríguez

Süntar

et al. 2020

Comp Rev Food Sci Food Safe

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Phytochemicals, especially polyphenols, are gaining more attention from both the scientific community and food, pharmaceutical, and cosmetics industries due to their implications in human health. In this line, lately new applications have emerged, and of great importance is the selection of accurate and reliable analytical methods for better evaluation of the quality of the end-products, which depends on diverse process variables as well as on the matrices and on the physicochemical properties of different polyphenols. The first of a two-part review on polyphenols will address the phytochemistry and biological activities of different classes of polyphenols including flavonoids, lignans and flavanolignans, stilbenoids, tannins, curcuminoids, and coumarins. Moreover, the possible interactions of polyphenols and current and potential industrial applications of polyphenols are discussed. K E Y W O R D S bioactivity, flavonoid, industrial uses, phytochemistry, plant-based food, polyphenol, possible interactions How to cite this article: Silva AS, Reboredo-Rodríguez P, Süntar I, et al. Evaluation of the status quo of polyphenols analysis: part iphytochemistry, bioactivity, interactions and industrial uses.

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“…It was observed that OVX rats fed flaxseed oil (10%) and sesame oil showed elongated trabeculae, less destruction, bone alterations, and a reduction in the activity of tartrate-resistant acid phosphatase (TRAP). Thus, the ingestion of phytoestrogens, for example, from flaxseed may aid in the prevention of osteoporosis associated with estrogen deficiency (Barker, 2019;Do et al, 2008;Sacco et al, 2009). The role of some foods and their components in the prevention and treatment of Type 2 diabetes has been extensively investigated and demonstrated through different scientific methodologies.…”

Section: Osteoporosismentioning

confidence: 99%

“…Regarding lignans, their precursors are present in the films that cover the cereals, being products from the transformation of lignin into phenolic compounds, whereas, in humans, they show anticarcinogenic and antioxidant properties, although being removed in the refinement process (Barker, 2019; Mali, Padhye, Anant, Hegde, & Kadam, 2019). Lignans can be found in plants and grains rich in fiber, such as wheat, barley, oats, beans, lentils, garlic, asparagus, broccoli, carrot and some fruits.…”

Section: Introductionmentioning

confidence: 99%

“…Lignans can be found in plants and grains rich in fiber, such as wheat, barley, oats, beans, lentils, garlic, asparagus, broccoli, carrot and some fruits. Oily grains, such as flaxseed, contain higher concentrations of biologically active lignans (Barker, 2019). On the other hand, foods rich in coumestans include peas, beans and alfalfa shoots (Landete et al, 2016).…”

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confidence: 99%

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The influence of phytoestrogens on different physiological and pathological processes: An overview

Petrine¹,

Bianco-Borges²

2020

Phytotherapy Research

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Functional foods have nutritional properties and organic functions, which are beneficial to health. Certain types of functional food components are so‐called phytoestrogens, non‐steroidal compounds derived from the metabolism of precursors contained in plants, which originate secondary metabotypes known to induce biological responses and by mimicry or modulating the action of endogenous estrogen. These molecules are involved in several physiological and pathological processes related to reproduction, bone remodeling, skin, cardiovascular, nervous, immune systems, and metabolism. This review aimed to present an overview of phytoestrogens regarding their chemical structure, actions, and effects in the organism given several pathologies. Several studies have demonstrated beneficial phytoestrogen actions, such as lipid profile improvement, cognitive function, menopause, oxidative stress, among others. Phytoestrogens effects are not completely elucidated, being necessary future research to understand the exact action mechanisms, whether they are via estrogen receptor or whether other hidden mechanisms produce these effects. Thus, this review makes a general approach to the phytoestrogen actions, beneficial effects, risk and limitations. However, the complexities of biological effects after ingestion of phytoestrogens and the differences in their metabolism and bioavailability indicate that interpretation of either risk or benefits needs to be made with caution.

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Lignans

Abstract: The 13 research articles/communications, six reviews, and one perspective that comprise this Special Issue on Lignans, highlight the most recent research and investigations into this diverse and important class of bioactive natural products [...]

Cited by 36 publications

References 20 publications

Nordihydroguaiaretic Acid as a Novel Substrate and Inhibitor of Catechol O-Methyltransferase Modulates 4-Hydroxyestradiol-Induced Cyto- and Genotoxicity in MCF-7 Cells

Nordihydroguaiaretic Acid as a Novel Substrate and Inhibitor of Catechol O-Methyltransferase Modulates 4-Hydroxyestradiol-Induced Cyto- and Genotoxicity in MCF-7 Cells

Evaluation of the status quo of polyphenols analysis: Part I—phytochemistry, bioactivity, interactions, and industrial uses

The influence of phytoestrogens on different physiological and pathological processes: An overview

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