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Lignans II
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Lignans II

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

Deadline for manuscript submissions: closed (10 December 2020) | Viewed by 41281

Special Issue Editor

Prof. Dr. David Barker

E-Mail Website
Guest Editor
School of Chemical Sciences, The University of Auckland, Auckland 1010, New Zealand
Interests: medicinal chemistry; natural products total synthesis; asymmetric synthesis; bioactive natural products; polymeric materials; anticancer treatments; synthesis from biowaste-derived materials; isotopically labelled materials
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

We are planning a second volume of the Special Issue on lignans to highlight current research on this important class of natural products. Lignans are are a class of secondary metabolites that are derived from the dimersation of two or more phenylpropanoid units. They are found with vast structural diversity, and it is well-established that this class of compounds exhibit a range of potent biological activities. Lignans have proven to be challenging and desirable synthetic targets and have instigated the development of a number of different synthetic methods, advancing our collective knowledge towards the synthesis of complex and unique structures.

This second volume of the Special Issue will focus on current research involving lignans, ranging in scope from recent isolation and structural elucidation of new compounds, biosynthetic studies to explore their origins, synthetic work towards lignan natural products and the use of lignans as synthetic precursors for other complex molecules. Further, the assessment of their biological activities and potential for further therapeutic development can also be reported.

Prof. David Barker
Guest Editor

Manuscript Submission Information

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Keywords

  • Lignans
  • Polyphenols
  • Total synthesis
  • Bioactive compounds
  • Biosynthesis
  • Antioxidants
  • Natural products
  • Phenyl propanoids

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Related Special Issue

Published Papers (8 papers)

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Research

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13 pages, 1601 KiB  
Article
Nordihydroguaiaretic Acid as a Novel Substrate and Inhibitor of Catechol O-Methyltransferase Modulates 4-Hydroxyestradiol-Induced Cyto- and Genotoxicity in MCF-7 Cells
by Jin-Hee Kim, Jimin Lee, Hyesoo Jeong, Mi Seo Bang, Jin-Hyun Jeong and Minsun Chang
Molecules 2021, 26(7), 2060; https://doi.org/10.3390/molecules26072060 - 3 Apr 2021
Cited by 2 | Viewed by 2628
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Special Issue Lignans II)
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13 pages, 2623 KiB  
Article
Formation of Tetrahydrofurano-, Aryltetralin, and Butyrolactone Norlignans through the Epoxidation of 9-Norlignans
by Patrik A. Runeberg, Dominique Agustin and Patrik C. Eklund
Molecules 2020, 25(5), 1160; https://doi.org/10.3390/molecules25051160 - 5 Mar 2020
Cited by 5 | Viewed by 3426
Abstract
Epoxidation of the C=C double bond in unsaturated norlignans derived from hydroxymatairesinol was studied. The intermediate epoxides were formed in up to quantitative conversions and were readily further transformed into tetrahydrofuran, aryltetralin, and butyrolactone products—in diastereomeric mixtures—through ring-closing reactions and intramolecular couplings. For [...] Read more.
Epoxidation of the C=C double bond in unsaturated norlignans derived from hydroxymatairesinol was studied. The intermediate epoxides were formed in up to quantitative conversions and were readily further transformed into tetrahydrofuran, aryltetralin, and butyrolactone products—in diastereomeric mixtures—through ring-closing reactions and intramolecular couplings. For epoxidation, the classical Prilezhaev reaction, using stoichiometric amounts of meta-chloroperbenzoic acid (mCPBA), was used. As an alternative method, a catalytic system using dimeric molybdenum-complexes [MoO2L]2 with ONO- or ONS-tridentate Schiff base ligands and aqueous tert-butyl hydroperoxide (TBHP) as oxidant was used on the same substrates. Although the epoxidation was quantitative when using the Mo-catalysts, the higher temperatures led to more side-products and lower yields. Kinetic studies were also performed on the Mo-catalyzed reactions. Full article
(This article belongs to the Special Issue Lignans II)
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13 pages, 2862 KiB  
Article
Design and Synthesis of a Compound Library Exploiting 5-Methoxyleoligin as Potential Cholesterol Efflux Promoter
by Thomas Linder, Sophie Geyrhofer, Eleni Papaplioura, Limei Wang, Atanas G. Atanasov, Hermann Stuppner, Verena M. Dirsch, Michael Schnürch and Marko D. Mihovilovic
Molecules 2020, 25(3), 662; https://doi.org/10.3390/molecules25030662 - 4 Feb 2020
Cited by 3 | Viewed by 3512
Abstract
5-Methoxyleoligin and leoligin are natural occurring lignans derived from Edelweiss (Leontopodium nivale ssp. alpinum), displaying potent pro-angiogenic and pro-arteriogenic activity. Cholesterol efflux from macrophages is associated with reverse cholesterol transport which inhibits the development of cardiovascular disease. Within this study, we [...] Read more.
5-Methoxyleoligin and leoligin are natural occurring lignans derived from Edelweiss (Leontopodium nivale ssp. alpinum), displaying potent pro-angiogenic and pro-arteriogenic activity. Cholesterol efflux from macrophages is associated with reverse cholesterol transport which inhibits the development of cardiovascular disease. Within this study, we developed a modular and stereoselective total synthesis of 5-methoxyleoligin which can be readily used to prepare a novel compound library of related analogs. The target 5-methoxyleoligin was synthesized exploiting a recently disclosed modular route, which allows also rapid synthesis of analogous compounds. All obtained products were tested towards macrophage cholesterol efflux enhancement and the performance was compared to the parent compound leoligin. It was found that variation on the aryl moiety in 2-position of the furan ring allows optimization of the activity profile, whereas the ester-functionality does not tolerate significant alterations. Full article
(This article belongs to the Special Issue Lignans II)
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14 pages, 1643 KiB  
Article
Distribution Patterns for Bioactive Constituents in Pericarp, Stalk and Seed of Forsythiae Fructus
by Lifang Wei, Yuqi Mei, Lisi Zou, Jiali Chen, Mengxia Tan, Chengcheng Wang, Zhichen Cai, Liqun Lin, Chuan Chai, Shengxin Yin and Xunhong Liu
Molecules 2020, 25(2), 340; https://doi.org/10.3390/molecules25020340 - 14 Jan 2020
Cited by 11 | Viewed by 2748
Abstract
Forsythiae Fructus (FF) is a widely used folk medicine in China, Japan, and Korea. The distribution of bioactive constituents throughout the fruit segments has rarely been addressed, although mounting evidence suggests that plant secondary metabolites are synthesized and distributed regularly. The phytochemical profiles [...] Read more.
Forsythiae Fructus (FF) is a widely used folk medicine in China, Japan, and Korea. The distribution of bioactive constituents throughout the fruit segments has rarely been addressed, although mounting evidence suggests that plant secondary metabolites are synthesized and distributed regularly. The phytochemical profiles of three segments of FF (pericarp, stalk and seed) were firstly revealed by liquid chromatography-tandem mass spectrometry (LC-MS/MS)-based quantitative analysis of twenty-one bioactive constituents, including three phenylethanoid glycosides, five lignans, eight flavonoids, and five phenolic acids to explore the spatial distribution of bioactive constituents. Furthermore, the hierarchical clustering analysis (HCA) and one-way analysis of variance (one-way ANOVA) were conducted to visualize and verify the distribution regularity of twenty-one analytes among three segments. The results showed that phytochemical profiles of the three segments were similar, i.e., phenylethanoid glycosides covering the most part were the predominant compounds, followed by lignans, flavonoids and phenolic acids. Nevertheless, the abundance of twenty-one bioactive constituents among three segments was different. Specifically, phenylethanoid glycosides were highly expressed in the seed; lignans were primarily enriched in the stalk; flavonoids were largely concentrated in the pericarp, while the contents of phenolic acids showed no much difference among various segments. The research improves our understanding of distribution patterns for bioactive constituents in FF, and also complements some scientific data for further exploring the quality formation mechanism of FF. Full article
(This article belongs to the Special Issue Lignans II)
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16 pages, 1878 KiB  
Article
Assaying Chlamydia pneumoniae Persistence in Monocyte-Derived Macrophages Identifies Dibenzocyclooctadiene Lignans as Phenotypic Switchers
by Eveliina Taavitsainen, Maarit Kortesoja, Tanja Bruun, Niklas G. Johansson and Leena Hanski
Molecules 2020, 25(2), 294; https://doi.org/10.3390/molecules25020294 - 11 Jan 2020
Cited by 7 | Viewed by 4053
Abstract
Antibiotic-tolerant persister bacteria involve frequent treatment failures, relapsing infections and the need for extended antibiotic treatment. The virulence of an intracellular human pathogen C. pneumoniae is tightly linked to its propensity for persistence and means for its chemosensitization are urgently needed. In the [...] Read more.
Antibiotic-tolerant persister bacteria involve frequent treatment failures, relapsing infections and the need for extended antibiotic treatment. The virulence of an intracellular human pathogen C. pneumoniae is tightly linked to its propensity for persistence and means for its chemosensitization are urgently needed. In the current work, persistence of C. pneumoniae clinical isolate CV6 was studied in THP-1 macrophages using quantitative PCR and quantitative culture. A dibenzocyclooctadiene lignan schisandrin reverted C. pneumoniae persistence and promoted productive infection. The concomitant administration of schisandrin and azithromycin resulted in significantly improved bacterial eradication compared to sole azithromycin treatment. In addition, the closely related lignan schisandrin C was superior to azithromycin in eradicating the C. pneumoniae infection from the macrophages. The observed chemosensitization of C. pneumoniae was associated with the suppression of cellular glutathione pools by the lignans, implying to a previously unknown aspect of chlamydia–host interactions. These data indicate that schisandrin lignans induce a phenotypic switch in C. pneumoniae, promoting the productive and antibiotic-susceptible phenotype instead of persistence. By this means, these medicinal plant -derived compounds show potential as adjuvant therapies for intracellular bacteria resuscitation. Full article
(This article belongs to the Special Issue Lignans II)
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17 pages, 4001 KiB  
Article
Insights into Lignan Composition and Biosynthesis in Stinging Nettle (Urtica dioica L.)
by Xuan Xu, Cédric Guignard, Jenny Renaut, Jean-Francois Hausman, Edoardo Gatti, Stefano Predieri and Gea Guerriero
Molecules 2019, 24(21), 3863; https://doi.org/10.3390/molecules24213863 - 26 Oct 2019
Cited by 11 | Viewed by 6786
Abstract
Stinging nettle (Urtica dioica L.) has been used as herbal medicine to treat various ailments since ancient times. The biological activity of nettle is chiefly attributed to a large group of phenylpropanoid dimers, namely lignans. Despite the pharmacological importance of nettle lignans, [...] Read more.
Stinging nettle (Urtica dioica L.) has been used as herbal medicine to treat various ailments since ancient times. The biological activity of nettle is chiefly attributed to a large group of phenylpropanoid dimers, namely lignans. Despite the pharmacological importance of nettle lignans, there are no studies addressing lignan biosynthesis in this plant. We herein identified 14 genes encoding dirigent proteins (UdDIRs) and 3 pinoresinol-lariciresinol reductase genes (UdPLRs) in nettle, which are two gene families known to be associated with lignan biosynthesis. Expression profiling of these genes on different organs/tissues revealed a specific expression pattern. Particularly, UdDIR7, 12 and 13 displayed a remarkable high expression in the top internode, fibre tissues of bottom internodes and roots, respectively. The relatively high expression of UdPLR1 and UdPLR2 in the young internodes, core tissue of bottom internode and roots is consistent with the high accumulation of lariciresinol and secoisolariciresinol in these tissues. Lignan quantification showed a high abundance of pinoresinol in roots and pinoresinol diglucosides in young internodes and leaves. This study sheds light on lignan composition and biosynthesis in nettle, providing a good basis for further functional analysis of DIRs and PLRs and, ultimately, engineering lignan metabolism in planta and in cell cultures. Full article
(This article belongs to the Special Issue Lignans II)
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Review

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18 pages, 1258 KiB  
Review
Iron Absorption in Celiac Disease and Nutraceutical Effect of 7-Hydroxymatairesinol. Mini-Review
by Isabella Zanella, Giulia Paiardi, Diego Di Lorenzo and Giorgio Biasiotto
Molecules 2020, 25(9), 2041; https://doi.org/10.3390/molecules25092041 - 27 Apr 2020
Cited by 5 | Viewed by 4311
Abstract
Anemia is the main extra-gastrointestinal symptom in inflammatory bowel diseases (IBDs). Interleukin-6 (IL-6) and other cytokines are secreted and act in the microenvironment of the small intestine mucous membrane of IBD patients. Iron is essential for multiple cell functions and its homeostasis is [...] Read more.
Anemia is the main extra-gastrointestinal symptom in inflammatory bowel diseases (IBDs). Interleukin-6 (IL-6) and other cytokines are secreted and act in the microenvironment of the small intestine mucous membrane of IBD patients. Iron is essential for multiple cell functions and its homeostasis is regulated by the hepcidin–ferroportin axis. Hepcidin (HEPC) is mainly produced by the liver in response to iron needs but is also an acute phase protein. During inflammation, hepcidin is upregulated by IL-6 and is responsible for iron compartmentalization within cells, in turn causing anemia of inflammation. Tissues other than liver can produce hepcidin in response to inflammatory stimuli, in order to decrease iron efflux at a local level, then acting in an autocrine–paracrine manner. In IBDs and, in particular, in celiac disease (CeD), IL-6 might trigger the expression, upregulation and secretion of hepcidin in the small intestine, reducing iron efflux and exacerbating defective iron absorption. 7-Hydroxymatairesinol (7-HMR) belongs to the family of lignans, polyphenolic compounds produced by plants, and has nutraceutical antioxidant, anti-inflammatory and estrogenic properties. In this mini-review we revise the role of inflammation in IBDs and in particular in CeD, focusing our attention on the close link among inflammation, anemia and iron metabolism. We also briefly describe the anti-inflammatory and estrogenic activity of 7-HMR contained in foods that are often consumed by CeD patients. Finally, considering that HEPC expression is regulated by iron needs, inflammation and estrogens, we explored the hypothesis that 7-HMR consumption could ameliorate anemia in CeD using Caco-2 cells as bowel model. Further studies are needed to verify the regulation pathway through which 7-HMR may interfere with the local production of HEPC in bowel. Full article
(This article belongs to the Special Issue Lignans II)
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17 pages, 2537 KiB  
Review
Lignans and Their Derivatives from Plants as Antivirals
by Qinghua Cui, Ruikun Du, Miaomiao Liu and Lijun Rong
Molecules 2020, 25(1), 183; https://doi.org/10.3390/molecules25010183 - 1 Jan 2020
Cited by 117 | Viewed by 13192
Abstract
Lignans are widely produced by various plant species; they are a class of natural products that share structural similarity. They usually contain a core scaffold that is formed by two or more phenylpropanoid units. Lignans possess diverse pharmacological properties, including their antiviral activities [...] Read more.
Lignans are widely produced by various plant species; they are a class of natural products that share structural similarity. They usually contain a core scaffold that is formed by two or more phenylpropanoid units. Lignans possess diverse pharmacological properties, including their antiviral activities that have been reported in recent years. This review discusses the distribution of lignans in nature according to their structural classification, and it provides a comprehensive summary of their antiviral activities. Among them, two types of antiviral lignans—podophyllotoxin and bicyclol, which are used to treat venereal warts and chronic hepatitis B (CHB) in clinical, serve as examples of using lignans for antivirals—are discussed in some detail. Prospects of lignans in antiviral drug discovery are also discussed. Full article
(This article belongs to the Special Issue Lignans II)
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