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Biological Activity of Secondary Metabolites
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Biological Activity of Secondary Metabolites

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

Deadline for manuscript submissions: closed (28 February 2018) | Viewed by 120032

Special Issue Editors

Prof. Dr. Helen D. Skaltsa

E-Mail Website
Guest Editor
Department of Pharmacognosy and Chemistry of Natural Products, School of Pharmacy, University of Athens, 15771 Athens, Greece
Interests: chemistry of natural products; analytical methods; NMR; GC-MS; terpenes (iridoids, sesquiterpene lactones, and triterpenes); phenolics (flavonoids, phenols, phenolic acids, and lignans); essential oils; ethnopharmacology; history of pharmacy
Special Issues, Collections and Topics in MDPI journals
Dr. Marina Soković

E-Mail Website
Guest Editor
Mycological Laboratory, Department of Plant Physiology, Institute for Biological Research "Siniša Stanković"—National Institute of Republic of Serbia, University of Belgrade, Bulevar Despota Stefana 142, 11000 Belgrade, Serbia
Interests: microfungi; macrofungi; antibacterial activity; antifungal activity; natural products
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue is related to the biological activities of natural products. Secondary metabolites are largely found in plants, marine organisms, bacteria, fungi, and insects. Natural products are used and marketed as medicines or food supplements for a number of health reasons, like the prevention or treatment of an illness or the reduction of health risks, or the maintenance of good health.

Past practices of compound drugs containing different natural ingredients predominately of plant origin were highly esteemed over centuries, but only recently are scientifically confirmed. The ethno pharmacological properties of healing plants have been used as a primary source of medicines for early drug discovery. The investigation of biological and chemical properties of natural products has, not only revealed new bioactive entities for the treatment of several diseases, but also enabled the development of synthetic organic chemistry. Natural products are the most successful source of leads for potential drug discovery and play a highly significant role in medicinal chemistry.

We particularly have interest in manuscripts dealing with the most recent research on bio-active natural products, including: Isolation and structure elucidation, metabolomic analyses, bio-assays, mechanisms of action of bioactive natural products, SAR studies, ethno-pharmacological studies.

Prof. Dr. Helen D. Skaltsa
Dr. Marina Sokovic
Guest Editors

Manuscript Submission Information

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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 semimonthly 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 2700 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

  • Secondary Metabolites
  • Analytical Techniques
  • Structure elucidation
  • Biological activities
  • Predicting biological activities
  • Structure-activity relationship
  • Target-based assays
  • Ligand-based drug design
  • Ethnopharmacological studies
  • Metabolomic analysis of medicinal plants

Published Papers (15 papers)

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Research

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11 pages, 1470 KiB  
Article
Alkaloids from Tetrastigma hemsleyanum and Their Anti-Inflammatory Effects on LPS-Induced RAW264.7 Cells
by Cai Yi Wang, Hyun-Jae Jang, Yoo Kyong Han, Xiang Dong Su, Seung Woong Lee, Mun-Chual Rho, Heng-Shan Wang, Seo Young Yang and Young Ho Kim
Molecules 2018, 23(6), 1445; https://doi.org/10.3390/molecules23061445 - 14 Jun 2018
Cited by 35 | Viewed by 4410
Abstract
Alkaloids 1–10 were isolated from the aerial parts of Tetrastigma hemsleyanum (APTH) and obtained from species of the genus Tetrastigma for the first time. The chemical structures of the isolated compounds were identified by NMR, UV, and MS analyses. Their anti-inflammatory [...] Read more.
Alkaloids 1–10 were isolated from the aerial parts of Tetrastigma hemsleyanum (APTH) and obtained from species of the genus Tetrastigma for the first time. The chemical structures of the isolated compounds were identified by NMR, UV, and MS analyses. Their anti-inflammatory activities were investigated by measuring nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW264.7 macrophages. Among all the isolates, compounds 6, 7 and 10 showed potent inhibitory activity against LPS-stimulated NO production in RAW264.7 cells (IC50: 31.9, 25.2 and 6.3 μM, respectively). Furthermore, APTH and S-(−)-trolline (10) inhibited induction of inflammatory cytokines or mediators such as interleukin-1β (IL-1β) and inducible nitric oxide synthase (iNOS) via suppression of nuclear factor κB (NF-κB) translocation into the nucleus. In addition, 10 suppressed extracellular signal-regulated protein kinase 1/2 (ERK1/2) mitogen-activated protein kinase (MAPK) phosphorylation in a dose-dependent manner. These results conclusively demonstrated that compound 10 displays anti-inflammatory activity via suppression of NF-κB activation and the ERK-MAPK signaling pathway in LPS-stimulated RAW264.7 cells. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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12 pages, 1086 KiB  
Communication
MAO-A Inhibitory Potential of Terpene Constituents from Ginger Rhizomes—A Bioactivity Guided Fractionation
by Wirginia Kukula-Koch, Wojciech Koch, Lidia Czernicka, Kazimierz Głowniak, Yoshinori Asakawa, Akemi Umeyama, Zbigniew Marzec and Takashi Kuzuhara
Molecules 2018, 23(6), 1301; https://doi.org/10.3390/molecules23061301 - 29 May 2018
Cited by 19 | Viewed by 5355
Abstract
Background: In the search for novel antidepressive drug candidates, bioguided fractionation of nonpolar constituents present in the oleoresin from ginger rhizomes (Zingiber officinale Roscoe, Zingiberaceae) was performed. This particular direction of the research was chosen due to the existing reports on the [...] Read more.
Background: In the search for novel antidepressive drug candidates, bioguided fractionation of nonpolar constituents present in the oleoresin from ginger rhizomes (Zingiber officinale Roscoe, Zingiberaceae) was performed. This particular direction of the research was chosen due to the existing reports on the antidepressive properties of ginger total extract. The search for individual metabolites acting as MAO-A inhibitors, which correspond to the apparent effect of the total extract, is the subject of this work. Methods: Hexane extracts from ginger rhizomes were fractionated by using column chromatography (including silica gel impregnated with silver nitrate) and semi-preparative high-performance chromatography. For the activity assessment, an in vitro monoamine oxidase A (MAO-A) inhibition luminescence assay was performed on 10 purified terpenes: 1,8-cineole, α-citronellal, geraniol, β-sesquiphellandrene, γ-terpinen, geranyl acetate, isobornyl acetate, terpinen-4-ol, (E,E)-α-farnesene, and α-zingiberene. Results: Geraniol and (−)-terpinen-4-ol were found to be the strongest enzyme inhibitors with inhibition of 44.1% and 42.5%, respectively, at a concentration of 125 µg/mL. No differences in the inhibition potential were observed for the different groups of terpenes: sesquiterpenes, monoterpenes, or sesquiterpene alcohols; however, the two most active compounds contained a hydroxyl moiety. Conclusions: Terpene constituents from ginger’s extract were found to exhibit moderate inhibitory properties against the MAO-A enzyme in in vitro tests. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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19 pages, 1401 KiB  
Article
Selected Plant Metabolites Involved in Oxidation-Reduction Processes during Bud Dormancy and Ontogenetic Development in Sweet Cherry Buds (Prunus avium L.)
by Susanne Baldermann, Thomas Homann, Susanne Neugart, Frank-M. Chmielewski, Klaus-Peter Götz, Kristin Gödeke, Gerd Huschek, Getrud E. Morlock and Harshadrai M. Rawel
Molecules 2018, 23(5), 1197; https://doi.org/10.3390/molecules23051197 - 17 May 2018
Cited by 14 | Viewed by 4115
Abstract
Many biochemical processes are involved in regulating the consecutive transition of different phases of dormancy in sweet cherry buds. An evaluation based on a metabolic approach has, as yet, only been partly addressed. The aim of this work, therefore, was to determine which [...] Read more.
Many biochemical processes are involved in regulating the consecutive transition of different phases of dormancy in sweet cherry buds. An evaluation based on a metabolic approach has, as yet, only been partly addressed. The aim of this work, therefore, was to determine which plant metabolites could serve as biomarkers for the different transitions in sweet cherry buds. The focus here was on those metabolites involved in oxidation-reduction processes during bud dormancy, as determined by targeted and untargeted mass spectrometry-based methods. The metabolites addressed included phenolic compounds, ascorbate/dehydroascorbate, reducing sugars, carotenoids and chlorophylls. The results demonstrate that the content of phenolic compounds decrease until the end of endodormancy. After a long period of constancy until the end of ecodormancy, a final phase of further decrease followed up to the phenophase open cluster. The main phenolic compounds were caffeoylquinic acids, coumaroylquinic acids and catechins, as well as quercetin and kaempferol derivatives. The data also support the protective role of ascorbate and glutathione in the para- and endodormancy phases. Consistent trends in the content of reducing sugars can be elucidated for the different phenophases of dormancy, too. The untargeted approach with principle component analysis (PCA) clearly differentiates the different timings of dormancy giving further valuable information. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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16 pages, 1445 KiB  
Article
Graminex Pollen: Phenolic Pattern, Colorimetric Analysis and Protective Effects in Immortalized Prostate Cells (PC3) and Rat Prostate Challenged with LPS
by Marcello Locatelli, Nicola Macchione, Claudio Ferrante, Annalisa Chiavaroli, Lucia Recinella, Simone Carradori, Gokhan Zengin, Stefania Cesa, Lidia Leporini, Sheila Leone, Luigi Brunetti, Luigi Menghini and Giustino Orlando
Molecules 2018, 23(5), 1145; https://doi.org/10.3390/molecules23051145 - 11 May 2018
Cited by 51 | Viewed by 5395
Abstract
Prostatitis, a general term describing prostate inflammation, is a common disease that could be sustained by bacterial or non-bacterial infectious agents. The efficacy of herbal extracts with antioxidant and anti-inflammatory effects for blunting the burden of inflammation and oxidative stress, with possible improvements [...] Read more.
Prostatitis, a general term describing prostate inflammation, is a common disease that could be sustained by bacterial or non-bacterial infectious agents. The efficacy of herbal extracts with antioxidant and anti-inflammatory effects for blunting the burden of inflammation and oxidative stress, with possible improvements in clinical symptoms, is under investigation. Pollen extracts have been previously reported as promising agents in managing clinical symptoms related to prostatitis. The aim of the present work was to evaluate the protective effects of Graminex pollen (GraminexTM, Deshler, OH, USA), a commercially available product based on standardized pollen extracts, in rat prostate specimens, ex vivo. In this context, we studied the putative mechanism of action of pollen on multiple inflammatory pathways, including the reduction of prostaglandin E2 (PGE2), nuclear factor kappa-light-chain-enhancer of activated B cells (NFκB), and malondialdehyde (MDA), whose activities were significantly increased by inflammatory stimuli. We characterized by means of chromatographic and colorimetric studies the composition of Graminex pollen to better correlate the activity of pollen on immortalized prostate cells (PC3), and in rat prostate specimens challenged with Escherichia coli lipopolysaccharide (LPS). We found that Graminex pollen was able to reduce radical oxygen species (ROS) production by PC3 cells and MDA, NFκB mRNA, and PGE2 levels, in rat prostate specimens. According to our experimental evidence, Graminex pollen appears to be a promising natural product for the management of the inflammatory components in the prostate. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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7 pages, 796 KiB  
Article
Tricycloalternarene Analogs from a Symbiotic Fungus Aspergillus sp. D and Their Antimicrobial and Cytotoxic Effects
by Huawei Zhang, Ziping Zhao, Jianwei Chen, Xuelian Bai and Hong Wang
Molecules 2018, 23(4), 855; https://doi.org/10.3390/molecules23040855 - 09 Apr 2018
Cited by 15 | Viewed by 3683
Abstract
Bioassay-guided fractionation of the crude extract of fermentation broth of one symbiotic strain Aspergillus sp. D from the coastal plant Edgeworthia chrysantha Lindl. led to isolation of one new meroterpenoid, tricycloalternarene 14b (1), together with four known analogs (2– [...] Read more.
Bioassay-guided fractionation of the crude extract of fermentation broth of one symbiotic strain Aspergillus sp. D from the coastal plant Edgeworthia chrysantha Lindl. led to isolation of one new meroterpenoid, tricycloalternarene 14b (1), together with four known analogs (2–5), tricycloalternarenes 2b (2), 3a (3), 3b (4), and ACTG-toxin F (5). Their chemical structures were unambiguously established on the basis of NMR, mass spectrometry, and optical rotation data analysis, as well as by comparison with literature data. Biological assays indicated that compound 2 exhibited potent in vitro cytotoxicity against human lung adenocarcinoma A549 cell line with an IC50 value of 2.91 μM, and compound 5 had a moderate inhibitory effect on Candida albicans, with an MIC value of 15.63 μM. The results indicated that this symbiotic strain D is an important producer of tricycloalternarene derivatives, with potential therapeutic application in treatment of cancer and pathogen infection. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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12 pages, 3034 KiB  
Article
Comparison of Inhibitory Capacities of 6-, 8- and 10-Gingerols/Shogaols on the Canonical NLRP3 Inflammasome-Mediated IL-1β Secretion
by Su-Chen Ho and Yi-Huang Chang
Molecules 2018, 23(2), 466; https://doi.org/10.3390/molecules23020466 - 21 Feb 2018
Cited by 43 | Viewed by 5127
Abstract
Endogenous noninfectious substances that mediate the nucleotide oligomerization domain (NOD)-like receptor family pyrin domain-containing 3 (NLRP3) inflammasome activation and interleukin (IL)-1β secretion causes inappropriate sterile inflammation and is implicated in the pathogenesis of several chronic diseases, such as type 2 diabetes mellitus, gout, [...] Read more.
Endogenous noninfectious substances that mediate the nucleotide oligomerization domain (NOD)-like receptor family pyrin domain-containing 3 (NLRP3) inflammasome activation and interleukin (IL)-1β secretion causes inappropriate sterile inflammation and is implicated in the pathogenesis of several chronic diseases, such as type 2 diabetes mellitus, gout, atherosclerosis and Alzheimer’s disease. Consequently, dietary phytochemicals exhibiting capacities to suppress canonical NLRP3 inflammasome-mediated IL-1β secretion can be a reliable supplement to prevent such diseases. The purpose of this study was to investigate and compare the inhibitory effects of ginger phytochemicals, including 6-, 8- and 10-gingerols/shogaols on the canonical NLRP3 inflammasome-mediated IL-1β secretion in THP-1 macrophages with ordered stimulations of lipopolysaccharide (LPS) and adenosine 5′-triphosphate (ATP). At 20 μM, the 10-gingerol and all the shogaols significantly inhibited canonical IL-1β secretion. The shogaols had a more potent inhibitory capacity than that of corresponding gingerols. Increase of alkyl chain length impacted negatively the inhibitory activity of shogaols. Additionally, these effective ginger phytochemicals not only inhibited the LPS-primed expression of pro-IL-1β and NLRP3, but also decreased ATP-activated caspase-1. The results demonstrated that ginger phytochemicals, especially the most potent, 6-shogaol, might be promising for developing as an inhibitor of the canonical NLRP3 inflammasome-mediated IL-1β secretion and further applied in prevention of NLRP3 inflammasome-associated diseases. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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11 pages, 1602 KiB  
Article
Efficacy of Compounds Isolated from the Essential Oil of Artemisia lavandulaefolia in Control of the Cigarette Beetle, Lasioderma serricorne
by Jun Zhou, Kexing Zou, Wenjuan Zhang, Shanshan Guo, Hong Liu, Jiansheng Sun, Jigang Li, Dongye Huang, Yan Wu, Shushan Du and Almaz Borjigidai
Molecules 2018, 23(2), 343; https://doi.org/10.3390/molecules23020343 - 07 Feb 2018
Cited by 14 | Viewed by 4540
Abstract
To develop natural product resources to control cigarette beetles (Lasioderma serricorne), the essential oil from Artemisia lavandulaefolia (Compositae) was investigated. Oil was extracted by hydrodistillation of the above-ground portion of A. lavandulaefolia and analyzed using gas chromatography-mass spectrometer (GC-MS). Extracted essential [...] Read more.
To develop natural product resources to control cigarette beetles (Lasioderma serricorne), the essential oil from Artemisia lavandulaefolia (Compositae) was investigated. Oil was extracted by hydrodistillation of the above-ground portion of A. lavandulaefolia and analyzed using gas chromatography-mass spectrometer (GC-MS). Extracted essential oil and three compounds isolated from the oil were then evaluated in laboratory assays to determine the fumigant, contact, and repellent efficacy against the stored-products’ pest, L. serricorne. The bioactive constituents from the oil extracts were identified as chamazulene (40.4%), 1,8-cineole (16.0%), and β-caryophyllene (11.5%). In the insecticidal activity assay, the adults of L. serricorne were susceptible to fumigant action of the essential oil and 1,8-cineole, with LC50 values of 31.81 and 5.18 mg/L air. The essential oil, 1,8-cineole, chamazulene, and β-caryophyllene exhibited contact toxicity with LD50 values of 13.51, 15.58, 15.18 and 35.52 μg/adult, respectively. During the repellency test, the essential oil and chamazulene had repellency approximating the positive control. The results indicated that chamazulene was abundant in A. lavandulaefolia essential oil and was toxic to cigarette beetles. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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11 pages, 1242 KiB  
Article
Isolation and Quantification of Ginsenoside Rh23, a New Anti-Melanogenic Compound from the Leaves of Panax ginseng
by Dae Young Lee, Hyoung-Geun Kim, Yeong-Geun Lee, Jin Hee Kim, Jae Won Lee, Bo-Ram Choi, In-Bae Jang, Geum-Soog Kim and Nam-In Baek
Molecules 2018, 23(2), 267; https://doi.org/10.3390/molecules23020267 - 29 Jan 2018
Cited by 16 | Viewed by 4800
Abstract
A new ginsenoside, named ginsenoside Rh23 (1), and 20-O-β-d-glucopyranosyl-3β,6α,12β,20β,25-pentahydroxydammar-23-ene (2) were isolated from the leaves of hydroponic Panax ginseng. Compounds were isolated by various column chromatography and their structures were determined based on spectroscopic [...] Read more.
A new ginsenoside, named ginsenoside Rh23 (1), and 20-O-β-d-glucopyranosyl-3β,6α,12β,20β,25-pentahydroxydammar-23-ene (2) were isolated from the leaves of hydroponic Panax ginseng. Compounds were isolated by various column chromatography and their structures were determined based on spectroscopic methods, including high resolution quadrupole/time of flight mass spectrometry (HR-QTOF/MS), nuclear magnetic resonance (NMR) spectroscopy, and infrared (IR) spectroscopy. To determine anti-melanogenic activity, the change in the melanin content in melan-a cells treated with identified compounds was tested. Additionally, we investigated the melanin inhibitory effects of ginsenoside Rh23 on pigmentation in a zebrafish in vivo model. Compound 1 inhibited potent melanogenesis in melan-a cells with 37.0% melanogenesis inhibition at 80 µM and also presented inhibition on the body pigmentation in zebrafish model. Although compound 2 showed slightly lower inhibitory activity than compound 1, it also showed significantly decreased melanogenesis in melan-a cell and in zebrafish model. These results indicated that compounds isolated from hydroponic P. ginseng may be used as new skin whitening compound through the in vitro and in vivo systems. Furthermore, this study demonstrated the utility of MS-based compound 1 for the quantitative analysis. Ginsenoside Rh23 (1) was found at a level of 0.31 mg/g in leaves of hydroponic P. ginseng. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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2718 KiB  
Article
Agarwood Essential Oil Displays Sedative-Hypnotic Effects through the GABAergic System
by Shuai Wang, Canhong Wang, Deqian Peng, Xinmin Liu, Chongming Wu, Peng Guo and Jianhe Wei
Molecules 2017, 22(12), 2190; https://doi.org/10.3390/molecules22122190 - 09 Dec 2017
Cited by 37 | Viewed by 7569
Abstract
Although agarwood has been used as a tranquilizer in Asian countries for hundreds of years, the underlying pharmacological basis is still unclear. This study investigated the sedative-hypnotic effect of agarwood essential oil (AEO) using locomotor activity and pentobarbital-induced sleeping assays in mice. Single [...] Read more.
Although agarwood has been used as a tranquilizer in Asian countries for hundreds of years, the underlying pharmacological basis is still unclear. This study investigated the sedative-hypnotic effect of agarwood essential oil (AEO) using locomotor activity and pentobarbital-induced sleeping assays in mice. Single (1-day) and multiple (7- and 14-days) administrations of 60 mg/kg AEO generated significant sedative effect on inhibiting locomotor activity and hypnotic effect on pentobarbital-induced sleeping in mice. Interestingly, prolonged AEO treatment did not result in obvious desensitization. Concoitant measurement of the levels of brain neurotransmitters using ultrafast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS) indicated that AEO had no significant effect on the levels of glutamic acid (Glu) and γ-aminobutyric acid (GABA) in the brain. However, the sedative-hypnotic effects were blocked by the type A GABA (GABAA) receptor antagonists bicuculline and flumazenil. In addition, AEO significantly elevated the expression of GABAA receptor subunits and subtypes in the cerebral cortex. Furthermore, AEO increased chlorine ion (Cl−) influx through GABAA receptors in human neuroblastoma cells. These results together demonstrate that AEO exerts its sedative-hypnotic effects through regulating gene expression of GABAA receptors and potentiating GABAA receptor function. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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4332 KiB  
Article
HPLC-PDA-MS/MS Characterization of Bioactive Secondary Metabolites from Turraea fischeri Bark Extract and Its Antioxidant and Hepatoprotective Activities In Vivo
by Mansour Sobeh, Mona F. Mahmoud, Omar M. Sabry, Rasha Adel, Malak Dmirieh, Assem M. El-Shazly and Michael Wink
Molecules 2017, 22(12), 2089; https://doi.org/10.3390/molecules22122089 - 29 Nov 2017
Cited by 20 | Viewed by 5529
Abstract
Turraea fischeri is an East African traditional herb, which is widely used in traditional medicine. In this study, we profiled the secondary metabolites in the methanol extract of T. fischeri bark using HPLC-PDA-ESI-MS/MS, and 20 compounds were tentatively identified. Several isomers of the [...] Read more.
Turraea fischeri is an East African traditional herb, which is widely used in traditional medicine. In this study, we profiled the secondary metabolites in the methanol extract of T. fischeri bark using HPLC-PDA-ESI-MS/MS, and 20 compounds were tentatively identified. Several isomers of the flavonolignan cinchonain-I and bis-dihydroxyphenylpropanoid-substituted catechin hexosides dominated the extract. Robust in vitro and in vivo antioxidant properties were observed in 1,1-diphenyl-2-picrylhydrazyl radical scavenging assay (DPPH) and ferric reducing antioxidant power (FRAP) assay, and in the model organism Caenorhabditis elegans. Additionally, the extract exhibited promising hepatoprotective activities in D-galactosamine (D-GaIN) treated rats. A significant reduction in the elevated levels of aspartate aminotransferase (AST), total bilirubin, gamma-glutamyltransferase (GGT), and malondialdehyde (MDA) and increase of glutathione (GSH) was observed in rats treated with the bark extract in addition to D-galactosamine when compared with rats treated with D-galactosamine alone. In conclusion, T. fischeri is apromising candidate for health-promoting and for pharmaceutical applications. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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1842 KiB  
Article
Asperflavin, an Anti-Inflammatory Compound Produced by a Marine-Derived Fungus, Eurotium amstelodami
by Xiudong Yang, Min-Cheol Kang, Yong Li, Eun-A. Kim, Sung-Myung Kang and You-Jin Jeon
Molecules 2017, 22(11), 1823; https://doi.org/10.3390/molecules22111823 - 29 Oct 2017
Cited by 20 | Viewed by 4808
Abstract
In the present study, 16 marine-derived fungi were isolated from four types of marine materials including float, algae, animals and drift woods along with the coast of Jeju Island, Korea and evaluated for anti-inflammatory effects in lipopolysaccharide (LPS)-stimulated RAW 24.7 cells. The broth [...] Read more.
In the present study, 16 marine-derived fungi were isolated from four types of marine materials including float, algae, animals and drift woods along with the coast of Jeju Island, Korea and evaluated for anti-inflammatory effects in lipopolysaccharide (LPS)-stimulated RAW 24.7 cells. The broth and mycelium extracts from the 16 fungi were prepared and the broth extract (BE) of Eurotium amstelodami (015-2) inhibited nitric oxide (NO) production in LPS-stimulated RAW 264.7 cells without cytotoxicity. By further bioassay-guided isolation, three compounds including asperflavin, neoechinulin A and preechinulin were successfully isolated from the BE of E. amstelodami. It was revealed that asperflavin showed no cytotoxicity up to 200 μM and significantly inhibited LPS-induced NO and PGE2 production in a dose-dependent manner. In the western blot results, asperflavin suppressed only inducible NOS (iNOS), but COX-2 were slightly down-regulated. Asperflavin was also observed to inhibit the production of pro-inflammatory cytokines including TNF-α, IL-1β, and IL-6. In conclusion, this study reports a potential use of asperflavin isolated from a marine fungus, E. amstelodami as an anti-inflammatory agent via suppression of iNOS and pro-inflammatory cytokines as well as no cytotoxicity. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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2303 KiB  
Article
Inhibition of Human Kallikrein 5 Protease by Triterpenoids from Natural Sources
by Yosuke Matsubara, Takashi Matsumoto, Junichi Koseki, Atsushi Kaneko, Setsuya Aiba and Kenshi Yamasaki
Molecules 2017, 22(11), 1829; https://doi.org/10.3390/molecules22111829 - 27 Oct 2017
Cited by 14 | Viewed by 6221
Abstract
Stratum corneum tryptic enzyme kallikrein 5 (KLK5) is a serine protease that is involved in the cell renewal and maintenance of the skin barrier function. The excessive activation of KLK5 causes an exacerbation of dermatoses, such as rosacea and atopic dermatitis. Some triterpenoids [...] Read more.
Stratum corneum tryptic enzyme kallikrein 5 (KLK5) is a serine protease that is involved in the cell renewal and maintenance of the skin barrier function. The excessive activation of KLK5 causes an exacerbation of dermatoses, such as rosacea and atopic dermatitis. Some triterpenoids are reported to suppress the serine proteases. We aimed to investigate whether bioactive triterpenoids modulate the KLK5 protease. Nineteen triterpenoids occurring in medicinal crude drugs were evaluated using an enzymatic assay to measure the anti-KLK5 activity. The KLK5-dependent cathelicidin peptide LL-37 production in human keratinocytes was examined using immunoprecipitation and Western blotting. Screening assays for evaluating the anti-KLK5 activity revealed that ursolic acid, oleanolic acid, saikosaponin b1, tumulosic acid and pachymic acid suppressed the KLK5 protease activity, although critical molecular moieties contributing to anti-KLK5 activity were unclarified. Ursolic acid and tumulosic acid suppressed the proteolytic processing of LL-37 in keratinocytes at ≤10 μM; no cytotoxicity was observed. Both triterpenoids were detected in the plasma of rats administered orally with triterpenoid-rich crude drug Jumihaidokuto. Our study reveals that triterpenoids, such as ursolic acid and tumulosic acid, modulate the KLK5 protease activity and cathelicidin peptide production. Triterpenoids may affect the skin barrier function via the regulation of proteases. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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Review

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26 pages, 3618 KiB  
Review
Response of Plant Secondary Metabolites to Environmental Factors
by Li Yang, Kui-Shan Wen, Xiao Ruan, Ying-Xian Zhao, Feng Wei and Qiang Wang
Molecules 2018, 23(4), 762; https://doi.org/10.3390/molecules23040762 - 27 Mar 2018
Cited by 919 | Viewed by 33763
Abstract
Plant secondary metabolites (SMs) are not only a useful array of natural products but also an important part of plant defense system against pathogenic attacks and environmental stresses. With remarkable biological activities, plant SMs are increasingly used as medicine ingredients and food additives [...] Read more.
Plant secondary metabolites (SMs) are not only a useful array of natural products but also an important part of plant defense system against pathogenic attacks and environmental stresses. With remarkable biological activities, plant SMs are increasingly used as medicine ingredients and food additives for therapeutic, aromatic and culinary purposes. Various genetic, ontogenic, morphogenetic and environmental factors can influence the biosynthesis and accumulation of SMs. According to the literature reports, for example, SMs accumulation is strongly dependent on a variety of environmental factors such as light, temperature, soil water, soil fertility and salinity, and for most plants, a change in an individual factor may alter the content of SMs even if other factors remain constant. Here, we review with emphasis how each of single factors to affect the accumulation of plant secondary metabolites, and conduct a comparative analysis of relevant natural products in the stressed and unstressed plants. Expectantly, this documentary review will outline a general picture of environmental factors responsible for fluctuation in plant SMs, provide a practical way to obtain consistent quality and high quantity of bioactive compounds in vegetation, and present some suggestions for future research and development. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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13 pages, 1637 KiB  
Review
Therapeutic Perspectives of 8-Prenylnaringenin, a Potent Phytoestrogen from Hops
by Kateřina Štulíková, Marcel Karabín, Jakub Nešpor and Pavel Dostálek
Molecules 2018, 23(3), 660; https://doi.org/10.3390/molecules23030660 - 15 Mar 2018
Cited by 62 | Viewed by 12574
Abstract
Hop (Humulus lupulus L.), as a key ingredient for beer brewing, is also a source of many biologically active molecules. A notable compound, 8-prenylnaringenin (8-PN), structurally belonging to the group of prenylated flavonoids, was shown to be a potent phytoestrogen, and thus, [...] Read more.
Hop (Humulus lupulus L.), as a key ingredient for beer brewing, is also a source of many biologically active molecules. A notable compound, 8-prenylnaringenin (8-PN), structurally belonging to the group of prenylated flavonoids, was shown to be a potent phytoestrogen, and thus, became the topic of active research. Here, we overview the pharmacological properties of 8-PN and its therapeutic opportunities. Due to its estrogenic effects, administration of 8-PN represents a novel therapeutic approach to the treatment of menopausal and post-menopausal symptoms that occur as a consequence of a progressive decline in hormone levels in women. Application of 8-PN in the treatment of menopause has been clinically examined with promising results. Other activities that have already been assessed include the potential to prevent bone-resorption or inhibition of tumor growth. On the other hand, the use of phytoestrogens is frequently questioned regarding possible adverse effects associated with long-term consumption. In conclusion, we emphasize the implications of using 8-PN in future treatments of menopausal and post-menopausal symptoms, including the need for precise evidence and further investigations to define the safety risks related to its therapeutic use. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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21 pages, 6343 KiB  
Review
Chemical Constituents and Pharmacological Activity of Agarwood and Aquilaria Plants
by Shuai Wang, Zhangxin Yu, Canhong Wang, Chongming Wu, Peng Guo and Jianhe Wei
Molecules 2018, 23(2), 342; https://doi.org/10.3390/molecules23020342 - 07 Feb 2018
Cited by 98 | Viewed by 10424
Abstract
Agarwood, a highly precious non-timber fragrant wood of Aquilaria spp. (Thymelaeaceae), has been widely used in traditional medicine, religious rites, and cultural activities. Due to the inflated demanding and depleted natural resources, the yields of agarwood collected from the wild are shrinking, and [...] Read more.
Agarwood, a highly precious non-timber fragrant wood of Aquilaria spp. (Thymelaeaceae), has been widely used in traditional medicine, religious rites, and cultural activities. Due to the inflated demanding and depleted natural resources, the yields of agarwood collected from the wild are shrinking, and the price is constantly rising, which restricts agarwood scientific research and wide application. With the sustainable planting and management of agarwood applied, and especially the artificial-inducing methods being used in China and Southeast Asian countries, agarwood yields are increasing, and the price is becoming more reasonable. Under this condition, illuminating the scientific nature of traditional agarwood application and developing new products and drugs from agarwood have become vitally important. Recently, the phytochemical investigations have achieved fruitful results, and more than 300 compounds have been isolated, including numerous new compounds that might be the characteristic constituents with physiological action. However, no one has focused on the new compounds and presented a summary until now. Alongside phytochemical advances, bioactivity screening and pharmacological investigation have also made a certain progress. Therefore, this review discussed the new compounds isolated after 2010, and summarized the pharmacological progress on agarwood and Aquilaria plants. Full article
(This article belongs to the Special Issue Biological Activity of Secondary Metabolites)
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