Molecules

Editorial

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4 pages, 176 KiB

Open AccessEditorial

Lignans

by David Barker

Molecules 2019, 24(7), 1424; https://doi.org/10.3390/molecules24071424 - 11 Apr 2019

Cited by 34 | Viewed by 5039

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 [...] Full article

(This article belongs to the Special Issue Lignans)

Research

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15 pages, 2341 KiB

Open AccessArticle

Quality Evaluation of Wild and Cultivated Schisandrae Chinensis Fructus Based on Simultaneous Determination of Multiple Bioactive Constituents Combined with Multivariate Statistical Analysis

by Shuyu Chen, Jingjing Shi, Lisi Zou, Xunhong Liu, Renmao Tang, Jimei Ma, Chengcheng Wang, Mengxia Tan and Jiali Chen

Molecules 2019, 24(7), 1335; https://doi.org/10.3390/molecules24071335 - 4 Apr 2019

Cited by 22 | Viewed by 3081

Abstract

Schisandrae Chinensis Fructus, also called wuweizi in China, was a widely used folk medicine in China, Korea, and Russia. Due to the limited natural resources and huge demand of wuweizi, people tend to cultivate wuweizi to protect this species. However, the quality of [...] Read more.

Schisandrae Chinensis Fructus, also called wuweizi in China, was a widely used folk medicine in China, Korea, and Russia. Due to the limited natural resources and huge demand of wuweizi, people tend to cultivate wuweizi to protect this species. However, the quality of wild and cultivated herbs of the same species may change. Little attention has been paid to comparing wild and cultivated wuweizi based on simultaneous determination of its active components, such as lignans and organic acids. An analytical method based on UFLC-QTRAP-MS/MS was used for the simultaneous determination of 15 components, including 11 lignans (schisandrin, gomisin D, gomisin J, schisandrol B, angeloylgomisin H, schizantherin B, schisanhenol, deoxyschizandrin, γ-schisandrin, schizandrin C, and schisantherin) and 4 organic acids (quinic acid, d(−)-tartaric acid, l-(−)-malic acid, and protocatechuic acid) in wuweizi under different ecological environments. Principal components analysis (PCA), partial least squares discrimination analysis (PLS-DA), independent sample t-test, and gray relational analysis (GRA) have been applied to classify and evaluate samples from different ecological environments according to the content of 15 components. The results showed that the differential compounds (i.e., quinic acid, l-(−)-malic acid, protocatechuic acid, schisandrol B) were significantly related to the classification of wild and cultivated wuweizi. GRA results demonstrated that the quality of cultivated wuweizi was not as good as wild wuweizi. The protocol not just provided a new method for the comprehensive evaluation and quality control of wild and cultivated wuweizi, but paved the way to differentiate them at the chemistry level. Full article

(This article belongs to the Special Issue Lignans)

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12 pages, 1121 KiB

Open AccessArticle

9-Norlignans: Occurrence, Properties and Their Semisynthetic Preparation from Hydroxymatairesinol

by Patrik Eklund and Jan-Erik Raitanen

Molecules 2019, 24(2), 220; https://doi.org/10.3390/molecules24020220 - 9 Jan 2019

Cited by 19 | Viewed by 4848

Abstract

Lignans, neolignans, norlignans and norneolignans constitute a large class of phenolic natural compounds. 9-Norlignans, here defined to contain a β–β’ bond between the two phenylpropanoid units and to lack carbon number 9 from the parent lignan structure, are the most rarely occurring compounds [...] Read more.

Lignans, neolignans, norlignans and norneolignans constitute a large class of phenolic natural compounds. 9-Norlignans, here defined to contain a β–β’ bond between the two phenylpropanoid units and to lack carbon number 9 from the parent lignan structure, are the most rarely occurring compounds within this class of natural compounds. We present here an overview of the structure, occurrence and biological activity of thirty-five 9-norlignans reported in the literature to date. In addition, we report the semisynthetic preparation of sixteen 9-norlignans using the natural lignan hydroxymatairesinol obtained from spruce knots, as starting material. 9-Norlignans are shown to exist in different species and to have various biological activities, and they may therefore serve as lead compounds for example for the development of anticancer agents. Hydroxymatairesinol is shown to be a readily available starting material for the preparation of norlignans of the imperanene, vitrofolal and noralashinol family. Full article

(This article belongs to the Special Issue Lignans)

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15 pages, 1466 KiB

Open AccessArticle

Lignans in Spirits: Chemical Diversity, Quantification, and Sensory Impact of (±)-Lyoniresinol

by Delphine Winstel and Axel Marchal

Molecules 2019, 24(1), 117; https://doi.org/10.3390/molecules24010117 - 30 Dec 2018

Cited by 20 | Viewed by 4467

Abstract

During barrel aging, spirits undergo organoleptic changes caused by the release of aroma and taste compounds. Recently, studies have revealed the bitter properties of oak wood lignans, such as (±)-lyoniresinol, and their contribution to wine taste. To evaluate the impact of lignans in [...] Read more.

During barrel aging, spirits undergo organoleptic changes caused by the release of aroma and taste compounds. Recently, studies have revealed the bitter properties of oak wood lignans, such as (±)-lyoniresinol, and their contribution to wine taste. To evaluate the impact of lignans in spirits, a targeted screening of 11 compounds was set up and served to validate their presence in this matrix, implying their release by oak wood during aging. After development and validation of a quantification method, the most abundant and the bitterest lignan, (±)-lyoniresinol, was assayed by liquid chromatography–high resolution mass spectrometry (LC-HRMS) in spirits. Its gustatory detection threshold was established at 2.6 mg/L in spirits. A large number of samples quantified were above this detection threshold, which suggests its effect of increased bitterness in spirit taste. Significant variations were observed in commercial spirits, with concentrations ranging from 0.2 to 11.8 mg/L, which could be related to differences in barrel aging processes. In “eaux-de-vie” of cognac, concentrations of (±)-lyoniresinol were observed in the range from 1.6 mg/L to 12 mg/L. Lower concentrations were measured for older vintages. Full article

(This article belongs to the Special Issue Lignans)

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13 pages, 3096 KiB

Open AccessArticle

Lignans from Bursera fagaroides Affect In Vivo Cell Behavior by Disturbing the Tubulin Cytoskeleton in Zebrafish Embryos

by Mayra Antúnez-Mojica, Andrés M. Rojas-Sepúlveda, Mario A. Mendieta-Serrano, Leticia Gonzalez-Maya, Silvia Marquina, Enrique Salas-Vidal and Laura Alvarez

Molecules 2019, 24(1), 8; https://doi.org/10.3390/molecules24010008 - 20 Dec 2018

Cited by 8 | Viewed by 4334

Abstract

By using a zebrafish embryo model to guide the chromatographic fractionation of antimitotic secondary metabolites, seven podophyllotoxin-type lignans were isolated from a hydroalcoholic extract obtained from the steam bark of Bursera fagaroides. The compounds were identified as podophyllotoxin (1), β-peltatin-A-methylether [...] Read more.

By using a zebrafish embryo model to guide the chromatographic fractionation of antimitotic secondary metabolites, seven podophyllotoxin-type lignans were isolated from a hydroalcoholic extract obtained from the steam bark of Bursera fagaroides. The compounds were identified as podophyllotoxin (1), β-peltatin-A-methylether (2), 5′-desmethoxy-β-peltatin-A-methylether (3), desmethoxy-yatein (4), desoxypodophyllotoxin (5), burseranin (6), and acetyl podophyllotoxin (7). The biological effects on mitosis, cell migration, and microtubule cytoskeleton remodeling of lignans 1–7 were further evaluated in zebrafish embryos by whole-mount immunolocalization of the mitotic marker phospho-histone H3 and by a tubulin antibody. We found that lignans 1, 2, 4, and 7 induced mitotic arrest, delayed cell migration, and disrupted the microtubule cytoskeleton in zebrafish embryos. Furthermore, microtubule cytoskeleton destabilization was observed also in PC3 cells, except for 7. Therefore, these results demonstrate that the cytotoxic activity of 1, 2, and 4 is mediated by their microtubule-destabilizing activity. In general, the in vivo and in vitro models here used displayed equivalent mitotic effects, which allows us to conclude that the zebrafish model can be a fast and cheap in vivo model that can be used to identify antimitotic natural products through bioassay-guided fractionation. Full article

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31 pages, 1798 KiB

Open AccessArticle

Combined In Vitro Studies and in Silico Target Fishing for the Evaluation of the Biological Activities of Diphylleia cymosa and Podophyllum hexandrum

by Marina Pereira Rocha, Priscilla Rodrigues Valadares Campana, Denise de Oliveira Scoaris, Vera Lucia de Almeida, Julio Cesar Dias Lopes, Julian Mark Hugh Shaw and Claudia Gontijo Silva

Molecules 2018, 23(12), 3303; https://doi.org/10.3390/molecules23123303 - 13 Dec 2018

Cited by 15 | Viewed by 4487

Abstract

This paper reports the in silico prediction of biological activities of lignans from Diphylleia cymosa and Podophyllum hexandrum combined with an in vitro bioassays. The extracts from the leaves, roots and rhizomes of both species were evaluated for their antibacterial, anticholinesterasic, antioxidant and [...] Read more.

This paper reports the in silico prediction of biological activities of lignans from Diphylleia cymosa and Podophyllum hexandrum combined with an in vitro bioassays. The extracts from the leaves, roots and rhizomes of both species were evaluated for their antibacterial, anticholinesterasic, antioxidant and cytotoxic activities. A group of 27 lignans was selected for biological activities prediction using the Active-IT system with 1987 ligand-based bioactivity models. The in silico approach was properly validated and several ethnopharmacological uses and known biological activities were confirmed, whilst others should be investigated for new drugs with potential clinical use. The extracts from roots of D. cymosa and from rhizomes and roots of P. hexandrum were very effective against Bacillus cereus and Staphylococcus aureus, while podophyllotoxin inhibited the growth of Staphylococcus aureus and Escherichia coli. D. cymosa leaves and roots showed anticholinesterasic and antioxidant activities, respectively. The evaluated extracts showed to be moderately toxic to THP-1 cells. The chromatographic characterization indicated that podophyllotoxin was the major constituent of P. hexandrum extract while kaempferol and its hexoside were the main constituents of D. cymosa leaves and roots, respectively. These results suggest that the podophyllotoxin could be the major antibacterial lignan, while flavonoids could be responsible for the antioxidant activity. Full article

(This article belongs to the Special Issue Lignans)

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16 pages, 574 KiB

Open AccessArticle

Targeted Lignan Profiling and Anti-Inflammatory Properties of Schisandra rubriflora and Schisandra chinensis Extracts

by Agnieszka Szopa, Michał Dziurka, Angelika Warzecha, Paweł Kubica, Marta Klimek-Szczykutowicz and Halina Ekiert

Molecules 2018, 23(12), 3103; https://doi.org/10.3390/molecules23123103 - 27 Nov 2018

Cited by 45 | Viewed by 5137

Abstract

Schisandra rubriflora is a dioecious plant of increasing importance due to its lignan composition, and therefore, possible therapeutic properties. The aim of the work was lignan profiling of fruits, leaves and shoots of female (F) and male (M) plants using UHPLC-MS/MS. Additionally, the [...] Read more.

Schisandra rubriflora is a dioecious plant of increasing importance due to its lignan composition, and therefore, possible therapeutic properties. The aim of the work was lignan profiling of fruits, leaves and shoots of female (F) and male (M) plants using UHPLC-MS/MS. Additionally, the anti-inflammatory activity of plant extracts and individual lignans was tested in vitro for the inhibition of 15-lipooxygenase (15-LOX), phospholipases A2 (sPLA₂), cyclooxygenase 1 and 2 (COX-1; COX-2) enzyme activities. The extracts of fruits, leaves and shoots of the pharmacopoeial species, S. chinensis, were tested for comparison. Twenty-four lignans were monitored. Lignan contents in S. rubriflora fruit extracts amounted to 1055.65 mg/100 g DW and the dominant compounds included schisanhenol, aneloylgomisin H, schisantherin B, schisandrin A, gomisin O, angeloylgomisin O and gomisin G. The content of lignan in leaf extracts was 853.33 (F) and 1106.80 (M) mg/100 g DW. Shoot extracts were poorer in lignans—559.97 (F) and 384.80 (M) mg/100 g DW. Schisantherin B, schisantherin A, 6-O-benzoylgomisin O and angeloylgomisin H were the dominant compounds in leaf and shoot extracts. The total content of detected lignans in S. chinensis fruit, leaf and shoot extracts was: 1686.95, 433.59 and 313.83 mg/100 g DW, respectively. Gomisin N, schisandrin A, schisandrin, gomisin D, schisantherin B, gomisin A, angeloylgomisin H and gomisin J were the dominant lignans in S. chinensis fruit extracts were. The results of anti-inflammatory assays revealed higher activity of S. rubriflora extracts. Individual lignans showed significant inhibitory activity against 15-LOX, COX-1 and COX-2 enzymes. Full article

(This article belongs to the Special Issue Lignans)

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26 pages, 1800 KiB

Open AccessArticle

Modular Synthesis and Biological Investigation of 5-Hydroxymethyl Dibenzyl Butyrolactones and Related Lignans

by Samuel J. Davidson, Lisa I. Pilkington, Nina C. Dempsey-Hibbert, Mohamed El-Mohtadi, Shiying Tang, Thomas Wainwright, Kathryn A. Whitehead and David Barker

Molecules 2018, 23(12), 3057; https://doi.org/10.3390/molecules23123057 - 22 Nov 2018

Cited by 11 | Viewed by 4590

Abstract

Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route [...] Read more.

Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway. Full article

(This article belongs to the Special Issue Lignans)

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7 pages, 1343 KiB

Open AccessCommunication

Concise Synthesis of (+)-β- and γ-Apopicropodophyllins, and Dehydrodesoxypodophyllotoxin

by Jian Xiao, Guangming Nan, Ya-Wen Wang and Yu Peng

Molecules 2018, 23(11), 3037; https://doi.org/10.3390/molecules23113037 - 21 Nov 2018

Cited by 15 | Viewed by 3462

Abstract

Herein, we present an expeditous synthesis of bioactive aryldihydronaphthalene lignans (+)-β- and γ-apopicropodophyllins, and arylnaphthalene lignan dehydrodesoxypodophyllotoxin. The key reaction is regiocontrolled oxidations of stereodivergent aryltetralin lactones, which were easily accessed from a nickel-catalyzed reductive cascade approach developed in our group. Full article

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15 pages, 1561 KiB

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

by Laurine Garros, Samantha Drouet, Cyrielle Corbin, Cédric Decourtil, Thibaud Fidel, Julie Lebas de Lacour, Emilie A. Leclerc, Sullivan Renouard, Duangjai Tungmunnithum, Joël Doussot, Bilal Haider Abassi, Benoit Maunit, Éric Lainé, Ophélie Fliniaux, François Mesnard and Christophe Hano

Molecules 2018, 23(10), 2636; https://doi.org/10.3390/molecules23102636 - 14 Oct 2018

Cited by 41 | Viewed by 5255

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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11 pages, 642 KiB

Open AccessArticle

Lignans from Tujia Ethnomedicine Heilaohu: Chemical Characterization and Evaluation of Their Cytotoxicity and Antioxidant Activities

by Yongbei Liu, Yupei Yang, Shumaila Tasneem, Nusrat Hussain, Muhammad Daniyal, Hanwen Yuan, Qingling Xie, Bin Liu, Jing Sun, Yuqing Jian, Bin Li, Shenghuang Chen and Wei Wang

Molecules 2018, 23(9), 2147; https://doi.org/10.3390/molecules23092147 - 27 Aug 2018

Cited by 42 | Viewed by 4526

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 (1–3) and twenty known (4–23) lignans. Three new heilaohulignans A-C (1–3) and seventeen known (4–20) lignans possessed dibenzocyclooctadiene skeletons. Similarly, one was a diarylbutane (21) and two were spirobenzofuranoid dibenzocyclooctadiene (22–23) lignans. Among the known compounds, 4–5, 7, 13–15 and 17–22 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

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12 pages, 2233 KiB

Open AccessArticle

Molecular Dynamics on Wood-Derived Lignans Analyzed by Intermolecular Network Theory

by Thomas Olof Sandberg, Christian Weinberger and Jan-Henrik Smått

Molecules 2018, 23(8), 1990; https://doi.org/10.3390/molecules23081990 - 10 Aug 2018

Cited by 6 | Viewed by 4695

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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11 pages, 1512 KiB

Open AccessArticle

Lignan Glycosides and Flavonoid Glycosides from the Aerial Portion of Lespedeza cuneata and Their Biological Evaluations

by Jiwon Baek, Tae Kyoung Lee, Jae-Hyoung Song, Eunyong Choi, Hyun-Jeong Ko, Sanghyun Lee, Sang Un Choi, Seong Lee, Sang-Woo Yoo, Seon-Hee Kim and Ki Hyun Kim

Molecules 2018, 23(8), 1920; https://doi.org/10.3390/molecules23081920 - 1 Aug 2018

Cited by 15 | Viewed by 4289

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 (3–7) and nine known flavonoid glycosides (8–14). 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 4–6 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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24 pages, 5138 KiB

Open AccessArticle

Lignans: A Chemometric Analysis

by Lisa I. Pilkington

Molecules 2018, 23(7), 1666; https://doi.org/10.3390/molecules23071666 - 9 Jul 2018

Cited by 22 | Viewed by 5711

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

Jump to: Editorial, Research, Other

25 pages, 1435 KiB

Open AccessReview

Naturally Lignan-Rich Foods: A Dietary Tool for Health Promotion?

by Carmen Rodríguez-García, Cristina Sánchez-Quesada, Estefanía Toledo, Miguel Delgado-Rodríguez and José J. Gaforio

Molecules 2019, 24(5), 917; https://doi.org/10.3390/molecules24050917 - 6 Mar 2019

Cited by 245 | Viewed by 19110

Abstract

Dietary guidelines universally advise adherence to plant-based diets. Plant-based foods confer considerable health benefits, partly attributable to their abundant micronutrient (e.g., polyphenol) content. Interest in polyphenols is largely focused on the contribution of their antioxidant activity to the prevention of various disorders, including [...] Read more.

Dietary guidelines universally advise adherence to plant-based diets. Plant-based foods confer considerable health benefits, partly attributable to their abundant micronutrient (e.g., polyphenol) content. Interest in polyphenols is largely focused on the contribution of their antioxidant activity to the prevention of various disorders, including cardiovascular disease and cancer. Polyphenols are classified into groups, such as stilbenes, flavonoids, phenolic acids, lignans and others. Lignans, which possess a steroid-like chemical structure and are defined as phytoestrogens, are of particular interest to researchers. Traditionally, health benefits attributed to lignans have included a lowered risk of heart disease, menopausal symptoms, osteoporosis and breast cancer. However, the intake of naturally lignan-rich foods varies with the type of diet. Consequently, based on the latest humans’ findings and gathered information on lignan-rich foods collected from Phenol Explorer database this review focuses on the potential health benefits attributable to the consumption of different diets containing naturally lignan-rich foods. Current evidence highlight the bioactive properties of lignans as human health-promoting molecules. Thus, dietary intake of lignan-rich foods could be a useful way to bolster the prevention of chronic illness, such as certain types of cancers and cardiovascular disease. Full article

(This article belongs to the Special Issue Lignans)

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37 pages, 13674 KiB

Open AccessReview

Oxidative Transformations of Lignans

by Patrik A. Runeberg, Yury Brusentsev, Sabine M. K. Rendon and Patrik C. Eklund

Molecules 2019, 24(2), 300; https://doi.org/10.3390/molecules24020300 - 15 Jan 2019

Cited by 20 | Viewed by 6377

Abstract

Numerous oxidative transformations of lignan structures have been reported in the literature. In this paper we present an overview on the current findings in the field. The focus is put on transformations targeting a specific structure, a specific reaction, or an interconversion of [...] Read more.

Numerous oxidative transformations of lignan structures have been reported in the literature. In this paper we present an overview on the current findings in the field. The focus is put on transformations targeting a specific structure, a specific reaction, or an interconversion of the lignan skeleton. Oxidative transformations related to biosynthesis, antioxidant measurements, and total syntheses are mostly excluded. Non-metal mediated as well as metal mediated oxidations are reported, and mechanisms based on hydrogen abstractions, epoxidations, hydroxylations, and radical reactions are discussed for the transformation and interconversion of lignan structures. Enzymatic oxidations, photooxidation, and electrochemical oxidations are also briefly reported. Full article

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21 pages, 937 KiB

Open AccessReview

A Review of Lignan Metabolism, Milk Enterolactone Concentration, and Antioxidant Status of Dairy Cows Fed Flaxseed

by André F. Brito and Yu Zang

Molecules 2019, 24(1), 41; https://doi.org/10.3390/molecules24010041 - 22 Dec 2018

Cited by 39 | Viewed by 5879

Abstract

Lignans are polyphenolic compounds with a wide spectrum of biological functions including antioxidant, anti-inflammatory, and anticarcinogenic activities, therefore, there is an increasing interest in promoting the inclusion of lignan-rich foods in humans’ diets. Flaxseed is the richest source of the lignan secoisolariciresinol diglucoside—a [...] Read more.

Lignans are polyphenolic compounds with a wide spectrum of biological functions including antioxidant, anti-inflammatory, and anticarcinogenic activities, therefore, there is an increasing interest in promoting the inclusion of lignan-rich foods in humans’ diets. Flaxseed is the richest source of the lignan secoisolariciresinol diglucoside—a compound found in the outer fibrous-containing layers of flax. The rumen appears to be the major site for the conversion of secoisolariciresinol diglucoside to the enterolignans enterodiol and enterolactone, but only enterolactone has been detected in milk of dairy cows fed flaxseed products (whole seeds, hulls, meal). However, there is limited information regarding the ruminal microbiota species involved in the metabolism of secoisolariciresinol diglucoside. Likewise, little is known about how dietary manipulation such as varying the nonstructural carbohydrate profile of rations affects milk enterolactone in dairy cows. Our review covers the gastrointestinal tract metabolism of lignans in humans and animals and presents an in-depth assessment of research that have investigated the impacts of flaxseed products on milk enterolactone concentration and animal health. It also addresses the pharmacokinetics of enterolactone consumed through milk, which may have implications to ruminants and humans’ health. Full article

(This article belongs to the Special Issue Lignans)

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22 pages, 6078 KiB

Open AccessReview

Advances in the Synthesis of Lignan Natural Products

by Xianhe Fang and Xiangdong Hu

Molecules 2018, 23(12), 3385; https://doi.org/10.3390/molecules23123385 - 19 Dec 2018

Cited by 49 | Viewed by 7889

Abstract

Lignans comprise a family of secondary metabolites existing widely in plants and also in human food sources. As important components, these compounds play remarkable roles in plants’ ecological functions as protection against herbivores and microorganisms. Meanwhile, foods rich in lignans have revealed potential [...] Read more.

Lignans comprise a family of secondary metabolites existing widely in plants and also in human food sources. As important components, these compounds play remarkable roles in plants’ ecological functions as protection against herbivores and microorganisms. Meanwhile, foods rich in lignans have revealed potential to decrease of risk of cancers. To date, a number of promising bioactivities have been found for lignan natural products and their unnatural analogues, including antibacterial, antiviral, antitumor, antiplatelet, phosphodiesterase inhibition, 5-lipoxygenase inhibition, HIV reverse transcription inhibition, cytotoxic activities, antioxidant activities, immunosuppressive activities and antiasthmatic activities. Therefore, the synthesis of this family and also their analogues have attracted widespread interest from the synthetic organic chemistry community. Herein, we outline advances in the synthesis of lignan natural products in the last decade. Full article

(This article belongs to the Special Issue Lignans)

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18 pages, 3330 KiB

Open AccessReview

Chemical Structures of Lignans and Neolignans Isolated from Lauraceae

by Ya Li, Shuhan Xie, Jinchuan Ying, Wenjun Wei and Kun Gao

Molecules 2018, 23(12), 3164; https://doi.org/10.3390/molecules23123164 - 30 Nov 2018

Cited by 32 | Viewed by 7094

Abstract

Lauraceae is a good source of lignans and neolignans, which are the most chemotaxonomic characteristics of many species of the family. This review describes 270 naturally occurring lignans and neolignans isolated from Lauraceae. Full article

(This article belongs to the Special Issue Lignans)

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20 pages, 1176 KiB

Open AccessReview

An Ethnopharmacological, Phytochemical and Pharmacological Review on Lignans from Mexican Bursera spp.

by Maria Carla Marcotullio, Massimo Curini and Judith X. Becerra

Molecules 2018, 23(8), 1976; https://doi.org/10.3390/molecules23081976 - 8 Aug 2018

Cited by 36 | Viewed by 6017

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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14 pages, 552 KiB

Open AccessPerspective

Dietary Lignans: Definition, Description and Research Trends in Databases Development

by Alessandra Durazzo, Massimo Lucarini, Emanuela Camilli, Stefania Marconi, Paolo Gabrielli, Silvia Lisciani, Loretta Gambelli, Altero Aguzzi, Ettore Novellino, Antonello Santini, Aida Turrini and Luisa Marletta

Molecules 2018, 23(12), 3251; https://doi.org/10.3390/molecules23123251 - 8 Dec 2018

Cited by 84 | Viewed by 7260

Abstract

The study aims to communicate the current status regarding the development and management of the databases on dietary lignans; within the phytochemicals, the class of the lignan compounds is of increasing interest because of their potential beneficial properties, i.e., anticancerogenic, antioxidant, estrogenic, and [...] Read more.

The study aims to communicate the current status regarding the development and management of the databases on dietary lignans; within the phytochemicals, the class of the lignan compounds is of increasing interest because of their potential beneficial properties, i.e., anticancerogenic, antioxidant, estrogenic, and antiestrogenic activities. Furthermore, an introductory overview of the main characteristics of the lignans is described here. In addition to the importance of the general databases, the role and function of a food composition database is explained. The occurrence of lignans in food groups is described; the initial construction of the first lignan databases and their inclusion in harmonized databases at national and/or European level is presented. In this context, some examples of utilization of specific databases to evaluate the intake of lignans are reported and described. Full article

(This article belongs to the Special Issue Lignans)

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