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Bioactive Plant Secondary Metabolites
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Bioactive Plant Secondary Metabolites

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Bioactives and Nutraceuticals".

Deadline for manuscript submissions: closed (31 May 2021) | Viewed by 19552

Special Issue Editor

Prof. Dr. Toshio Morikawa

E-Mail Website
Guest Editor
Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashiosaka, Osaka 577-8502, Japan
Interests: isolation and structure determination of bioactive natural products; synthetic studies on bioactive natural products; structure-activity relationship studies on bioactive natural products; studies of bioactive natural products on the application to pharmaceuticals, nutraceuticals, dietary supplements, cosmetics, and food additives; mechanisms of action of bioactive natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural products have contributed to the development of many drugs for diverse applications. In particular, medicinal plant-derived natural products and their derivatives are still one of the most abundant and reliable sources of valuable therapeutic agents. Their chemical diversity and variety of biological activities have attracted the attention of chemists, biochemists, biologists, etc. This Special Issue on "Bioactive Plant Secondary Metabolites" will offer biological active natural products as candidates and/or leads for pharmaceuticals, dietary supplements, functional foods, cosmetics, food additives, etc. The research fields of this Special Issue include natural products chemistry, phytochemistry, pharmacognosy, food chemistry, bioorganic synthetic chemistry, chemical biology, molecular biology, molecular pharmacology, and other related research fields of bioactive natural products from plant resources. Original research and review articles on the bioactivity and mechanisms of action of plant secondary metabolites and their role in promoting human health and preventing diseases are invited. I am looking forward to receiving many submissions from outstanding experts in these research fields.

Prof. Dr. Toshio Morikawa
Guest Editor

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Keywords

  • Natural product chemistry 
  • Phytochemistry 
  • Pharmacognosy 
  • Food chemistry 
  • Bioorganic chemistry 
  • Chemical biology 
  • Molecular biology 
  • Molecular pharmacology 
  • Isolation and structure determination 
  • Total synthesis 
  • Structure–activity relationship 
  • Mechanism of action

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Published Papers (5 papers)

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Research

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26 pages, 4556 KiB  
Article
LC-ESI-QTOF-MS/MS Analysis, Cytotoxic, Antiviral, Antioxidant, and Enzyme Inhibitory Properties of Four Extracts of Geranium pyrenaicum Burm. f.: A Good Gift from the Natural Treasure
by Łukasz Świątek, Elwira Sieniawska, Kouadio Ibrahime Sinan, Magdalena Maciejewska-Turska, Anastazja Boguszewska, Małgorzata Polz-Dacewicz, Ismail Senkardes, Gokalp Ozmen Guler, Nabeelah Bibi Sadeer, Mohamad Fawzi Mahomoodally and Gokhan Zengin
Int. J. Mol. Sci. 2021, 22(14), 7621; https://doi.org/10.3390/ijms22147621 - 16 Jul 2021
Cited by 29 | Viewed by 4736
Abstract
This study focused on the biological evaluation and chemical characterization of Geranium pyrenaicum Burm. f. Different solvent extracts (hexane, ethyl acetate, methanol, and water extracts) were prepared. The phytochemical profile, antioxidant, and enzyme inhibitory activity were investigated. Cytotoxicity was assessed using VERO, FaDu, [...] Read more.
This study focused on the biological evaluation and chemical characterization of Geranium pyrenaicum Burm. f. Different solvent extracts (hexane, ethyl acetate, methanol, and water extracts) were prepared. The phytochemical profile, antioxidant, and enzyme inhibitory activity were investigated. Cytotoxicity was assessed using VERO, FaDu, HeLa and RKO cells. The antiviral activity was carried out against HSV-1 (Herpes simplex virus 1) propagated in VERO cell line. The aqueous extract, possessing high phenolic content (170.50 mg gallic acid equivalent/g extract), showed the highest reducing capacity (613.27 and 364.10 mg Trolox equivalent/g extract, for cupric reducing antioxidant capacity and ferric reducing antioxidant power, respectively), radical scavenging potential (469.82 mg Trolox equivalent/g extract, against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)), metal chelating ability (52.39 mg ethylenediaminetetraacetic acid equivalent/g extract) and total antioxidant capacity (3.15 mmol Trolox equivalent/g extract). Liquid chromatography-electrospray ionization-quadrupole time-of-flight-mass spectrometry (LC-ESI-QTOF-MS/MS) alloved to tentatively identify a total of 56 compounds in the extracts, including ellagitannins, gallic acid and galloyl derivatives amongst others. The ethyl acetate extracts substantially depressed cholinesterase enzymes (4.49 and 12.26 mg galantamine equivalent/g extract against AChE and BChE, respectively) and α-amylase enzyme (1.04 mmol acarbose equivalent/g extract). On the other hand, the methanolic extract inhibited tyrosinase (121.42 mg kojic acid equivalent/g extract) and α-glucosidase (2.39 mmol acarbose equivalent/g extract) activities. The highest selectivity towards all cancer cell lines (SI 4.5–10.8) was observed with aqueous extract with the FaDu cells being the most sensitive (CC50 40.22 µg/mL). It can be concluded that the presence of certain bioactive antiviral molecules may be related to the high anti HSV-1 activity of the methanolic extract. This work has generated vital scientific data on this medicinal plant, which is a prospective candidate for the creation of innovative phyto-pharmaceuticals. Full article
(This article belongs to the Special Issue Bioactive Plant Secondary Metabolites)
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16 pages, 4178 KiB  
Article
Dibenzofuran, 4-Chromanone, Acetophenone, and Dithiecine Derivatives: Cytotoxic Constituents from Eupatorium fortunei
by Chun-Hao Chang, Semon Wu, Kai-Cheng Hsu, Wei-Jan Huang and Jih-Jung Chen
Int. J. Mol. Sci. 2021, 22(14), 7448; https://doi.org/10.3390/ijms22147448 - 12 Jul 2021
Cited by 7 | Viewed by 2324
Abstract
Five new compounds, eupatodibenzofuran A (1), eupatodibenzofuran B (2), 6-acetyl-8-methoxy-2,2-dimethylchroman-4-one (3), eupatofortunone (4), and eupatodithiecine (5), have been isolated from the aerial part of Eupatorium fortunei, together with 11 known compounds ( [...] Read more.
Five new compounds, eupatodibenzofuran A (1), eupatodibenzofuran B (2), 6-acetyl-8-methoxy-2,2-dimethylchroman-4-one (3), eupatofortunone (4), and eupatodithiecine (5), have been isolated from the aerial part of Eupatorium fortunei, together with 11 known compounds (6‒16). Compounds 1 and 2 featured a new carbon skeleton with an unprecedented 1-(9-(4-methylphenyl)-6-methyldibe nzo[b,d]furan-2-yl)ethenone. Among the isolates, compound 1 exhibited potent inhibitory activity with IC50 values of 5.95 ± 0.89 and 5.55 ± 0.23 μM, respectively, against A549 and MCF-7 cells. The colony-formation assay demonstrated that compound 1 (5 μM) obviously decreased A549 and MCF-7 cell proliferation, and Western blot test confirmed that compound 1 markedly induced apoptosis of A549 and MCF-7 cells through mitochondrial- and caspase-3-dependent pathways. Full article
(This article belongs to the Special Issue Bioactive Plant Secondary Metabolites)
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19 pages, 4582 KiB  
Article
Coumarin Interferes with Polar Auxin Transport Altering Microtubule Cortical Array Organization in Arabidopsis thaliana (L.) Heynh. Root Apical Meristem
by Leonardo Bruno, Emanuela Talarico, Luz Cabeiras-Freijanes, Maria Letizia Madeo, Antonella Muto, Marco Minervino, Luigi Lucini, Begoña Miras-Moreno, Adriano Sofo and Fabrizio Araniti
Int. J. Mol. Sci. 2021, 22(14), 7305; https://doi.org/10.3390/ijms22147305 - 7 Jul 2021
Cited by 12 | Viewed by 3324
Abstract
Coumarin is a phytotoxic natural compound able to affect plant growth and development. Previous studies have demonstrated that this molecule at low concentrations (100 µM) can reduce primary root growth and stimulate lateral root formation, suggesting an auxin-like activity. In the present study, [...] Read more.
Coumarin is a phytotoxic natural compound able to affect plant growth and development. Previous studies have demonstrated that this molecule at low concentrations (100 µM) can reduce primary root growth and stimulate lateral root formation, suggesting an auxin-like activity. In the present study, we evaluated coumarin’s effects (used at lateral root-stimulating concentrations) on the root apical meristem and polar auxin transport to identify its potential mode of action through a confocal microscopy approach. To achieve this goal, we used several Arabidopsis thaliana GFP transgenic lines (for polar auxin transport evaluation), immunolabeling techniques (for imaging cortical microtubules), and GC-MS analysis (for auxin quantification). The results highlighted that coumarin induced cyclin B accumulation, which altered the microtubule cortical array organization and, consequently, the root apical meristem architecture. Such alterations reduced the basipetal transport of auxin to the apical root apical meristem, inducing its accumulation in the maturation zone and stimulating lateral root formation. Full article
(This article belongs to the Special Issue Bioactive Plant Secondary Metabolites)
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12 pages, 1446 KiB  
Article
Investigating the Antifungal Mechanism of Action of Polygodial by Phenotypic Screening in Saccharomyces cerevisiae
by Purity N. Kipanga, Liesbeth Demuyser, Johannes Vrijdag, Elja Eskes, Petra D’hooge, Josphat Matasyoh, Geert Callewaert, Joris Winderickx, Patrick Van Dijck and Walter Luyten
Int. J. Mol. Sci. 2021, 22(11), 5756; https://doi.org/10.3390/ijms22115756 - 28 May 2021
Cited by 3 | Viewed by 3408
Abstract
Polygodial is a “hot” peppery-tasting sesquiterpenoid that was first described for its anti-feedant activity against African armyworms. Using the haploid deletion mutant library of Saccharomyces cerevisiae, a genome-wide mutant screen was performed to shed more light on polygodial’s antifungal mechanism of action. [...] Read more.
Polygodial is a “hot” peppery-tasting sesquiterpenoid that was first described for its anti-feedant activity against African armyworms. Using the haploid deletion mutant library of Saccharomyces cerevisiae, a genome-wide mutant screen was performed to shed more light on polygodial’s antifungal mechanism of action. We identified 66 deletion strains that were hypersensitive and 47 that were highly resistant to polygodial treatment. Among the hypersensitive strains, an enrichment was found for genes required for vacuolar acidification, amino acid biosynthesis, nucleosome mobilization, the transcription mediator complex, autophagy and vesicular trafficking, while the resistant strains were enriched for genes encoding cytoskeleton-binding proteins, ribosomal proteins, mitochondrial matrix proteins, components of the heme activator protein (HAP) complex, and known regulators of the target of rapamycin complex 1 (TORC1) signaling. WE confirm that polygodial triggers a dose-dependent vacuolar alkalinization and that it increases Ca2+ influx and inhibits glucose-induced Ca2+ signaling. Moreover, we provide evidence suggesting that TORC1 signaling and its protective agent ubiquitin play a central role in polygodial resistance, suggesting that they can be targeted by polygodial either directly or via altered Ca2+ homeostasis. Full article
(This article belongs to the Special Issue Bioactive Plant Secondary Metabolites)
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Review

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42 pages, 1256 KiB  
Review
Phytochemical Composition and Biological Activities of Scorzonera Species
by Karolina Lendzion, Agnieszka Gornowicz, Krzysztof Bielawski and Anna Bielawska
Int. J. Mol. Sci. 2021, 22(10), 5128; https://doi.org/10.3390/ijms22105128 - 12 May 2021
Cited by 22 | Viewed by 4281
Abstract
The genus Scorzonera comprises nearly 200 species, naturally occurring in Europe, Asia, and northern parts of Africa. Plants belonging to the Scorzonera genus have been a significant part of folk medicine in Asia, especially China, Mongolia, and Turkey for centuries. Therefore, they have [...] Read more.
The genus Scorzonera comprises nearly 200 species, naturally occurring in Europe, Asia, and northern parts of Africa. Plants belonging to the Scorzonera genus have been a significant part of folk medicine in Asia, especially China, Mongolia, and Turkey for centuries. Therefore, they have become the subject of research regarding their phytochemical composition and biological activity. The aim of this review is to present and assess the phytochemical composition, and bioactive potential of species within the genus Scorzonera. Studies have shown the presence of many bioactive compounds like triterpenoids, sesquiterpenoids, flavonoids, or caffeic acid and quinic acid derivatives in extracts obtained from aerial and subaerial parts of the plants. The antioxidant and cytotoxic properties have been evaluated, together with the mechanism of anti-inflammatory, analgesic, and hepatoprotective activity. Scorzonera species have also been investigated for their activity against several bacteria and fungi strains. Despite mild cytotoxicity against cancer cell lines in vitro, the bioactive properties in wound healing therapy and the treatment of microbial infections might, in perspective, be the starting point for the research on Scorzonera species as active agents in medical products designed for miscellaneous skin conditions. Full article
(This article belongs to the Special Issue Bioactive Plant Secondary Metabolites)
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