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Special Issue "Lignans"

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: 31 January 2019

Special Issue Editor

Guest Editor
Assoc. Prof. David Barker

School of Chemical Sciences, University of Auckland, Private Bag 92019, Auckland, New Zealand
Website | E-Mail
Interests: natural product total synthesis; medicinal chemistry; asymmetric synthesis; lignans; polymeric materials; anti-cancer treatments; synthesis from biowaste-derived materials; isotopically labelled materials

Special Issue Information

Dear Colleagues,

Lignans are traditionally defined as a class of secondary metabolites that are derived from the dimersation of two or more phenylpropanoid units. Despite their common biosynthetic origins, they boast a vast structural diversity. It is also well-established that this class of compounds exhibit a range of potent biological activities. Owing to these factors, lignans have proven to be a challenging and desirable synthetic target and has instigated the development of a number of different synthetic methods, advancing our collective knowledge towards the synthesis of complex and unique structures.

This Special Issue is focused on current research concerning this notable class of compounds, ranging in scope from recent isolation and structural elucidation of new and novel compounds, biosynthetic studies to explore their origins, total syntheses and strategies towards lignan synthesis, assessment of their biological activities and potential for further therapeutic development.

Assoc. Prof. David Barker
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • lignans
  • polyphenols
  • total synthesis
  • bioactive compounds
  • biosynthesis
  • antioxidants
  • natural products
  • phenyl propanoids

Published Papers (6 papers)

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Research

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Open AccessArticle Insight into the Influence of Cultivar Type, Cultivation Year, and Site on the Lignans and Related Phenolic Profiles, and the Health-Promoting Antioxidant Potential of Flax (Linum usitatissimum L.) Seeds
Molecules 2018, 23(10), 2636; https://doi.org/10.3390/molecules23102636
Received: 23 September 2018 / Revised: 10 October 2018 / Accepted: 11 October 2018 / Published: 14 October 2018
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Abstract
Flaxseeds are a functional food representing, by far, the richest natural grain source of lignans, and accumulate substantial amounts of other health beneficial phenolic compounds (i.e., flavonols, hydroxycinnamic acids). This specific accumulation pattern is related to their numerous beneficial effects on human health.
[...] Read more.
Flaxseeds are a functional food representing, by far, the richest natural grain source of lignans, and accumulate substantial amounts of other health beneficial phenolic compounds (i.e., flavonols, hydroxycinnamic acids). This specific accumulation pattern is related to their numerous beneficial effects on human health. However, to date, little data is available concerning the relative impact of genetic and geographic parameters on the phytochemical yield and composition. Here, the major influence of the cultivar over geographic parameters on the flaxseed phytochemical accumulation yield and composition is evidenced. The importance of genetic parameters on the lignan accumulation was further confirmed by gene expression analysis monitored by RT-qPCR. The corresponding antioxidant activity of these flaxseed extracts was evaluated, both in vitro, using ferric reducing antioxidant power (FRAP), oxygen radical absorbance capacity (ORAC), and iron chelating assays, as well as in vivo, by monitoring the impact of UV-induced oxidative stress on the lipid membrane peroxidation of yeast cells. Our results, both the in vitro and in vivo studies, confirm that flaxseed extracts are an effective protector against oxidative stress. The results point out that secoisolariciresinol diglucoside, caffeic acid glucoside, and p-coumaric acid glucoside are the main contributors to the antioxidant capacity. Considering the health benefits of these compounds, the present study demonstrates that the flaxseed cultivar type could greatly influence the phytochemical intakes and, therefore, the associated biological activities. We recommend that this crucial parameter be considered in epidemiological studies dealing with flaxseeds. Full article
(This article belongs to the Special Issue Lignans)
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Graphical abstract

Open AccessArticle Lignans from Tujia Ethnomedicine Heilaohu: Chemical Characterization and Evaluation of Their Cytotoxicity and Antioxidant Activities
Molecules 2018, 23(9), 2147; https://doi.org/10.3390/molecules23092147
Received: 30 July 2018 / Revised: 24 August 2018 / Accepted: 24 August 2018 / Published: 27 August 2018
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Abstract
Heilaohu, the roots of Kadsura coccinea, has a long history of use in Tujia ethnomedicine for the treatment of rheumatoid arthritis and gastroenteric disorders, and a lot of work has been done in order to know the material basis of its pharmacological activities.
[...] Read more.
Heilaohu, the roots of Kadsura coccinea, has a long history of use in Tujia ethnomedicine for the treatment of rheumatoid arthritis and gastroenteric disorders, and a lot of work has been done in order to know the material basis of its pharmacological activities. The chemical investigation led to the isolation and characterization of three new (13) and twenty known (423) lignans. Three new heilaohulignans A-C (13) and seventeen known (420) lignans possessed dibenzocyclooctadiene skeletons. Similarly, one was a diarylbutane (21) and two were spirobenzofuranoid dibenzocyclooctadiene (2223) lignans. Among the known compounds, 45, 7, 1315 and 1722 were isolated from this species for the first time. The structures were established, using IR, UV, MS and NMR data. The absolute configurations of the new compounds were determined by circular dichroism (CD) spectra. The isolated lignans were further evaluated for their cytotoxicity and antioxidant activities. Compound 3 demonstrated strong cytotoxic activity with an IC50 value of 9.92 µM, compounds 9 and 13 revealed weak cytotoxicity with IC50 values of 21.72 µM and 18.72 µM, respectively in the HepG-2 human liver cancer cell line. Compound 3 also showed weak cytotoxicity against the BGC-823 human gastric cancer cell line and the HCT-116 human colon cancer cell line with IC50 values of 16.75 µM and 16.59 µM, respectively. A chemiluminescence assay for antioxidant status of isolated compounds implied compounds 11 and 20, which showed weak activity with IC50 values of 25.56 µM and 21.20 µM, respectively. Full article
(This article belongs to the Special Issue Lignans)
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Open AccessArticle Molecular Dynamics on Wood-Derived Lignans Analyzed by Intermolecular Network Theory
Molecules 2018, 23(8), 1990; https://doi.org/10.3390/molecules23081990
Received: 3 July 2018 / Revised: 8 August 2018 / Accepted: 8 August 2018 / Published: 10 August 2018
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Abstract
The dynamics of interactions to a solvent is a key factor in the proper characterization of new molecular structures. In molecular dynamics simulations, the solvent molecules are explicitly present, thereby defining a more accurate description on how the solvent molecules affect the molecular
[...] Read more.
The dynamics of interactions to a solvent is a key factor in the proper characterization of new molecular structures. In molecular dynamics simulations, the solvent molecules are explicitly present, thereby defining a more accurate description on how the solvent molecules affect the molecular conformation. Intermolecular interactions in chemical systems, e.g., hydrogen bonds, can be considered as networks or graphs. Graph theoretical analyses can be an outstanding tool in analyzing the changes in interactions between solvent and solute. In this study, the software ChemNetworks is applied to interaction studies between TIP4P solvent molecules and organic solutes, i.e., wood-derived lignan-based ligands called LIGNOLs, thereby supporting the research of interaction networks between organic molecules and solvents. This new approach is established by careful comparisons to studies using previously available tools. In the hydration studies, tetramethyl 1,4-diol is found to be the LIGNOL which was most likely to form hydrogen bonds to the TIP4P solvent. Full article
(This article belongs to the Special Issue Lignans)
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Graphical abstract

Open AccessArticle Lignan Glycosides and Flavonoid Glycosides from the Aerial Portion of Lespedeza cuneata and Their Biological Evaluations
Molecules 2018, 23(8), 1920; https://doi.org/10.3390/molecules23081920
Received: 9 July 2018 / Revised: 28 July 2018 / Accepted: 30 July 2018 / Published: 1 August 2018
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Abstract
Lespedeza cuneata (Fabaceae), known as Chinese bushclover, has been used in traditional medicines for the treatment of diseases including diabetes, hematuria, and insomnia. As part of a continuing search for bioactive constituents from Korean medicinal plant sources, phytochemical analysis of the aerial portion
[...] Read more.
Lespedeza cuneata (Fabaceae), known as Chinese bushclover, has been used in traditional medicines for the treatment of diseases including diabetes, hematuria, and insomnia. As part of a continuing search for bioactive constituents from Korean medicinal plant sources, phytochemical analysis of the aerial portion of L. cuneata led to the isolation of two new lignan glycosides (1,2) along with three known lignan glycosides (37) and nine known flavonoid glycosides (814). Numerous analysis techniques, including 1D and 2D NMR spectroscopy, CD spectroscopy, HR-MS, and chemical reactions, were utilized for structural elucidation of the new compounds (1,2). The isolated compounds were evaluated for their applicability in medicinal use using cell-based assays. Compounds 1 and 46 exhibited weak cytotoxicity against four human breast cancer cell lines (Bt549, MCF7, MDA-MB-231, and HCC70) (IC50 < 30.0 μM). However, none of the isolated compounds showed significant antiviral activity against PR8, HRV1B, or CVB3. In addition, compound 10 produced fewer lipid droplets in Oil Red O staining of mouse mesenchymal stem cells compared to the untreated negative control without altering the amount of alkaline phosphatase staining. Full article
(This article belongs to the Special Issue Lignans)
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Graphical abstract

Open AccessArticle Lignans: A Chemometric Analysis
Molecules 2018, 23(7), 1666; https://doi.org/10.3390/molecules23071666
Received: 20 June 2018 / Revised: 2 July 2018 / Accepted: 7 July 2018 / Published: 9 July 2018
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Abstract
The physicochemical properties of classical lignans, neolignans, flavonolignans and carbohydrate-lignan conjugates (CLCs) were analysed to assess their ADMET profiles and establish if these compounds are lead-like/drug-like and thus have potential to be or act as leads in the development of future
[...] Read more.
The physicochemical properties of classical lignans, neolignans, flavonolignans and carbohydrate-lignan conjugates (CLCs) were analysed to assess their ADMET profiles and establish if these compounds are lead-like/drug-like and thus have potential to be or act as leads in the development of future therapeutics. It was found that while no studied compounds were lead-like, a very large proportion (>75%) fulfilled all the requirements to be deemed as present in drug-like space and almost all compounds studied were in the known drug space. Principal component analysis was an effective technique that enabled the investigation of the relationship between the studied molecular descriptors and was able to separate the lignans from their sugar derivatives and flavonolignans, primarily according to the parameters that are considered when defining chemical space (i.e., number of hydrogen bond donors, acceptors, rotatable bonds, polar surface area and molecular weight). These results indicate that while CLCs and flavonolignans are less drug-like, lignans show a particularly high level of drug-likeness, an observation that coupled with their potent biological activities, demands future pursuit into their potential for use as therapeutics. Full article
(This article belongs to the Special Issue Lignans)
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Review

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Open AccessReview An Ethnopharmacological, Phytochemical and Pharmacological Review on Lignans from Mexican Bursera spp.
Molecules 2018, 23(8), 1976; https://doi.org/10.3390/molecules23081976
Received: 5 July 2018 / Revised: 1 August 2018 / Accepted: 5 August 2018 / Published: 8 August 2018
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Abstract
The genus Bursera belongs to the family Burseraceae and has been used in traditional Mexican medicine for treating various pathophysiological disorders. The most representative phytochemicals isolated from this genus are terpenoids and lignans. Lignans are phenolic metabolites known for their antioxidant, apoptotic, anti-cancer,
[...] Read more.
The genus Bursera belongs to the family Burseraceae and has been used in traditional Mexican medicine for treating various pathophysiological disorders. The most representative phytochemicals isolated from this genus are terpenoids and lignans. Lignans are phenolic metabolites known for their antioxidant, apoptotic, anti-cancer, anti-inflammatory, anti-bacterial, anti-viral, anti-fungal, and anti-protozoal properties. Though the genus includes more than 100 species, we have attempted to summarize the biological activities of the 34 lignans isolated from selected Mexican Bursera plants. Full article
(This article belongs to the Special Issue Lignans)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Author: Minsun Chang
Affiliation: Sookmyung Womens Univ, South Korea
 
Author: M. Christofidou-Solomidou
Affiliation:  Univ Penn, Div Pulm Allergy & Crit Care Med, Perelman Sch Med, USA
 
Author: Manabu Horikawa
Affiliation: Bioorganic Research Institute, Suntory Foundation for Life Sciences (SUNBOR), Japan
 
Author: Xiangdong Hu
Affiliation: Northwest University, China
 
Author: Jun Murata
Affiliation: Bioorganic Research Institute, Suntory Foundation for Life Sciences, Japan
 
Author: Yu Peng
Affiliation: Lanzhou University, China
 
Author: Jiří Pospíšil
Affiliation: SPIL, Brno, Czech Republic 
 
Author: Huichang Bi
Affiliation: School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, China
 
Author: Cláudia Gontijo Silva
Affiliation: Serviço de Biotecnologia Vegetal, Fundação Ezequiel Dias, Brazil
 
Author: Axel Marchal
Affiliation: Université de Bordeaux, ISVV, France
 
Author: A.F. Brito
Affiliation: Department of Agriculture, Nutrition, and Food Systems, University of New Hampshire, Durham, UK
 
Author: Patrik Eklund
Affiliation: Laboratory of Organic Chemistry, Abo Akademi University, Finland
 
Author: Ya Li
Affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, China
 
Author: Laura Alvarez
Affiliation: Centro de Investigaciones Químicas-IICBA, Universidad Autónoma del Estado de Morelos, Mexico
 
 
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