Biological Activities and Constituents of Plant-Derived Natural Products and Their Application

A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (20 May 2023) | Viewed by 18354

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Guest Editor
Natural Product Informatics Research Center, Korea Institute of Science and Technology (KIST), Gangneung 25451, Republic of Korea
Interests: phytochemistry; phytochemicals; bioactive compounds; natural product isolation
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural products have been investigated to alleviate disease since early human history. They have been utilized in pharmaceuticals, agrochemicals, cosmetics, fine chemicals, and nutraceuticals. Indeed, natural products are extremely rich sources of biomolecules useful for a multitude of applications. Of these, plant-derived natural products have been some of the most important, and continue to be the source and inspiration for a substantial fraction to improve quality of life. Currently, approximately 350,000 species of plants are believed to exist, and a third have been discovered, but only a few have been investigated chemically or biologically. Therefore, studies on a diverse range of plants are a vital necessity. Additionally, with recent technological advances accelerating the emergence of new screening systems, there is a need to rapidly identify novel lead compounds. We believe that a very significant portion of these leads will continue to be from natural products, especially plants.

For all these reasons, this Special Issue invites researchers to contribute original research and review articles that provide evidence for the constituents of diverse plants and their pharmacological properties. To ensure the quality of the articles in the Special Issue, the phytochemical and biological information of plant extracts should be included.

Dr. Jaeyoung Kwon
Guest Editor

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Keywords

  • plant extracts
  • phytochemistry
  • phytochemicals
  • bioactive compounds
  • natural medicines

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Published Papers (10 papers)

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Research

12 pages, 1604 KiB  
Article
Magnolin Inhibits Paclitaxel-Induced Cold Allodynia and ERK1/2 Activation in Mice
by Nari Kim, Geehoon Chung, So-Ri Son, Jae Hyun Park, Young Hyun Lee, Keon-Tae Park, Ik-Hyun Cho, Dae Sik Jang and Sun Kwang Kim
Plants 2023, 12(12), 2283; https://doi.org/10.3390/plants12122283 - 12 Jun 2023
Cited by 2 | Viewed by 1049
Abstract
Chemotherapy-induced peripheral neuropathy (CIPN) is a common side effect of anti-cancer drugs. The main symptoms often include sensory disturbances and neuropathic pain, and currently there is no effective treatment for this condition. This study aimed to investigate the suppressive effects of magnolin, an [...] Read more.
Chemotherapy-induced peripheral neuropathy (CIPN) is a common side effect of anti-cancer drugs. The main symptoms often include sensory disturbances and neuropathic pain, and currently there is no effective treatment for this condition. This study aimed to investigate the suppressive effects of magnolin, an extracellular signal-regulated kinase (ERK) inhibitor substance derived from a 95% EtOH extract of the seeds of Magnolia denudata, on the symptoms of CIPN. A taxol-based anti-cancer drug paclitaxel (PTX) was repeatedly injected (2 mg/kg/day, total 8 mg/kg) into mice to induce CIPN. A neuropathic pain symptom was assessed using a cold allodynia test that scores behaviors of licking and shaking paw after plantar administration of acetone drop. Magnolin was administered intraperitoneally (0.1, 1, or 10 mg/kg) and behavioral changes to acetone drop were measured. The effect of magnolin administration on ERK expression in the dorsal root ganglion (DRG) was investigated using western blot analysis. The results showed that the repeated injections of PTX induced cold allodynia in mice. Magnolin administration exerted an analgesic effect on the PTX-induced cold allodynia and inhibited the ERK phosphorylation in the DRG. These results suggest that magnolin could be developed as an alternative treatment to suppress paclitaxel-induced neuropathic pain symptoms. Full article
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16 pages, 4595 KiB  
Article
Elucidation of Phytochemicals Affecting Platelet Responsiveness in Dangguisu-san: Active Ingredient Prediction and Experimental Research Using Network Pharmacology
by Dong-Ha Lee, Hee Jae Kwak, Yonghee Shin, Sung Jin Kim, Ga Hee Lee, Il-Ho Park, Seung Hyun Kim and Ki Sung Kang
Plants 2023, 12(5), 1120; https://doi.org/10.3390/plants12051120 - 02 Mar 2023
Cited by 1 | Viewed by 1409
Abstract
Plant-derived phytochemicals are emerging as novel agents for protection against chronic disorders. Dangguisu-san is a herbal prescription to invigorate the blood and relieve pain. Among the numerous active constituents of Dangguisu-san, those expected to be effective at inhibiting platelet aggregation were predicted using [...] Read more.
Plant-derived phytochemicals are emerging as novel agents for protection against chronic disorders. Dangguisu-san is a herbal prescription to invigorate the blood and relieve pain. Among the numerous active constituents of Dangguisu-san, those expected to be effective at inhibiting platelet aggregation were predicted using a network pharmacological method, and their efficacy was experimentally demonstrated. All four identified chemical components, namely chrysoeriol, apigenin, luteolin, and sappanchalcone, suppressed the aggregation of platelets to a certain extent. However, we report, for the first time, that chrysoeriol acts as a strong inhibitor of platelet aggregation. Although additional in vivo studies are needed, among the complex constituents of herbal medicines, the components that exert an inhibitory effect on platelet aggregation were predicted using a network pharmacological method and experimentally confirmed with human platelets. Full article
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27 pages, 6289 KiB  
Article
Phytoecdysteroids and Anabolic Effect of Atriplex dimorphostegia: UPLC-PDA-MS/MS Profiling, In Silico and In Vivo Models
by Eman Zaghloul, Heba Handousa, Abdel Nasser B. Singab, Mohey M. Elmazar, Iriny M. Ayoub and Noha Swilam
Plants 2023, 12(1), 206; https://doi.org/10.3390/plants12010206 - 03 Jan 2023
Cited by 1 | Viewed by 1848
Abstract
Atriplex dimorphostegia (Saltbush) is an annual halophytic shrub that is widely distributed across various parts of Asia. The current study is the first to report the metabolites profile of the total ethanol extract of the aerial parts of A. dimorphostegia (TEAD), and its [...] Read more.
Atriplex dimorphostegia (Saltbush) is an annual halophytic shrub that is widely distributed across various parts of Asia. The current study is the first to report the metabolites profile of the total ethanol extract of the aerial parts of A. dimorphostegia (TEAD), and its anabolic activity together with the isolated 20-hydroxyecdysone (20-HE) in orchidectomized male rats. TEAD was analyzed and standardized utilizing UPLC-PDA-ESI–MS/MS and UPLC-PDA-UV techniques, resulting in tentative identification of fifty compounds including polyphenols, steroids and triterpenoids. In addition, 20-HE was quantified, representing 26.79 μg/mg of the extract. Phytochemical investigation of TEAD resulted in the isolation of 20-HE from the ethyl acetate fraction (EFAD) and was identified by conventional spectroscopic methods of analysis. Furthermore, the anabolic effect of the isolated 20-HE and TEAD was then evaluated using in silico and in vivo models. Molecular docking experiments revealed in vitro selectivity of 20-HE towards estrogen receptors (ERs), specifically ERβ over ERα and androgenic receptor (AR). The anabolic efficacy of TEAD and 20-HE was studied in orchidectomized immature male Wistar rats using the weight of gastrocnemius and soleus muscles. The weights of ventral prostate and seminal vesicles were used as indicators for androgenic activity. Rats administered 20-HE and TEAD showed a significant increase (p = 0.0006 and p < 0.0001) in the net muscle mass compared to the negative control, while the group receiving TEAD showed the highest percentage among all groups at p < 0.0001. Histopathological investigation of skeletal muscle fibers showed normal morphological structures, and the group administered 20-HE showed an increase in cross sectional area of muscle fibers comparable to methandienone and testosterone groups at p > 0.99. A. dimorphostegia exhibited promising anabolic activity with minimal androgenic side effects. Full article
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14 pages, 1722 KiB  
Article
Chemical Constituents of the Roots of Polygala tenuifolia and Their Anti-Inflammatory Effects
by So-Ri Son, Young-Seo Yoon, Joon-Pyo Hong, Jae-Min Kim, Kyung-Tae Lee and Dae Sik Jang
Plants 2022, 11(23), 3307; https://doi.org/10.3390/plants11233307 - 30 Nov 2022
Cited by 4 | Viewed by 1926
Abstract
Increasing scientific evidence has demonstrated that the roots of Polygala tenuifolia Willd. have pharmacological effects related to anti-inflammation. Therefore, the aim of this study is to investigate the chemical constituents from P. tenuifolia roots as anti-inflammatory drug candidates. In the present work, [...] Read more.
Increasing scientific evidence has demonstrated that the roots of Polygala tenuifolia Willd. have pharmacological effects related to anti-inflammation. Therefore, the aim of this study is to investigate the chemical constituents from P. tenuifolia roots as anti-inflammatory drug candidates. In the present work, twenty-three compounds were isolated from P. tenuifolia roots, including three saponins (13), ten phenylpropanoid sucrose esters (412), one benzoic acid sugar ester derivative (13), four xanthones (1417), two hydroxy benzophenone derivatives (18 and 19), two phenolic derivatives (20 and 21), and two ionones (22 and 23). All isolates were tested for their inhibitory effects of LPS-stimulated NO and PGE2 production in RAW 264.7 macrophages. Among these, 3-O-(3,4,5-trimethoxy-cinnamoyl),6′-O-(p-methoxybenzoyl) sucrose ester (TCMB; 11) together with compounds 3 and 21 exhibited significant inhibitory effects on NO production, while TCMB and compounds 17, 19, and 21 showed strong inhibitory effects on PGE2 production. Specifically, TCMB (11) downregulated the protein levels of iNOS and COX-2 in LPS-induced RAW 264.7 macrophages. In addition, TCMB (11) dose-dependently diminished the relative mRNA expression levels of iNOS, PGE2, and proinflammatory cytokines (TNF-α, IL-1β, and IL-6). A molecular docking study showed that TCMB (11) has strong binding affinities with iNOS and COX-2. Full article
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22 pages, 4798 KiB  
Article
Liposomal Formulation of Botanical Extracts may Enhance Yield Triggering PR Genes and Phenylpropanoid Pathway in Barley (Hordeum vulgare)
by Géza Hegedűs, Barbara Kutasy, Márta Kiniczky, Kincső Decsi, Ákos Juhász, Ágnes Nagy, József Péter Pallos and Eszter Virág
Plants 2022, 11(21), 2969; https://doi.org/10.3390/plants11212969 - 03 Nov 2022
Cited by 4 | Viewed by 1900
Abstract
This work aimed to study the plant conditioning effect and mode of action of a plant-based biostimulant used in organic farming. This new generation plant biostimulant, named ELICE16INDURES®, is rich in plant bio-active ingredients containing eleven supercritical botanical extracts encapsulated in [...] Read more.
This work aimed to study the plant conditioning effect and mode of action of a plant-based biostimulant used in organic farming. This new generation plant biostimulant, named ELICE16INDURES®, is rich in plant bio-active ingredients containing eleven supercritical botanical extracts encapsulated in nano-scale liposomes. The dose–response (10 to 240 g ha−1) relationship was tested in a field population of autumn barley (Hordeum vulgare) test crop, and underlying molecular mechanisms were studied. Applying nanotechnology, cell-identical nanoparticles may help the better uptake and delivery of active ingredients increasing resilience, vitality, and crop yield. The amount of harvested crops showed a significant increase of 27.5% and 39.9% interconnected to higher normalized difference vegetation index (NDVI) of 20% and 25% after the treatment of low and high dosages (20 and 240 g ha−1), respectively. Illumina NextSeq 550 sequencing, gene expression profiling, and KEGG-pathway analysis of outstanding dosages indicated the upregulation of pathogenesis-related (PR) and other genes—associated with induced resistance—which showed dose dependency as well. Full article
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10 pages, 1740 KiB  
Article
New Monocyclic Terpenoid Lactones from a Brown Algae Sargassum macrocarpum as Monoamine Oxidase Inhibitors
by Jaeyoung Kwon, Kyerim Lee, Hoseong Hwang, Seong-Hwan Kim, Se Eun Park, Prasannavenkatesh Durai, Keunwan Park, Hyung-Seop Kim, Dae Sik Jang, Jae Sue Choi and Hak Cheol Kwon
Plants 2022, 11(15), 1998; https://doi.org/10.3390/plants11151998 - 31 Jul 2022
Cited by 6 | Viewed by 1833
Abstract
Algae are unique natural products that can produce various types of biologically active compounds. The 70% ethanol extract of brown algae Sargassum macrocarpum collected from the East Sea of Korea inhibited human monoamine oxidases A and B enzymes (hMAO-A and h [...] Read more.
Algae are unique natural products that can produce various types of biologically active compounds. The 70% ethanol extract of brown algae Sargassum macrocarpum collected from the East Sea of Korea inhibited human monoamine oxidases A and B enzymes (hMAO-A and hMAO-B) at a 50 μg/mL concentration. The bioassay-guided isolation was performed through solid-phase extraction and the Sepbox system followed by serial high-performance liquid chromatography on the reverse phase condition, resulting in the identification of two new monocyclic terpenoid lactones, sargassumins A and B (1 and 2). The planar structures of the compounds were determined by a combination of spectroscopic data. The absolute configurations were determined by the interpretation of circular dichroism data. Compound 1 exhibited mild hMAO-A inhibition (42.18 ± 2.68% at 200 μM) and docked computationally into the active site of hMAO-A (−8.48 kcal/mol). Although compound 2 could not be tested due to insufficient quantity, it docked better into hMAO-A (−9.72 kcal/mol). Therefore, the above results suggest that this type of monocyclic terpenoid lactone could be one of the potential lead compounds for the treatment of psychiatric or neurological diseases. Full article
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11 pages, 2815 KiB  
Article
Chemical Constituents from the Aerial Parts of Artemisia iwayomogi and Their Anti-Neuroinflammatory Activities
by So-Ri Son, In Gyong Ju, Jinhee Kim, Keon-Tae Park, Myung Sook Oh and Dae Sik Jang
Plants 2022, 11(15), 1954; https://doi.org/10.3390/plants11151954 - 27 Jul 2022
Cited by 4 | Viewed by 1670
Abstract
Neuroinflammation, predominantly mediated by microglial activation, is a key immunological response in the pathogenesis of neurodegenerative disorders. In our preliminary study, the aerial part of Artemisia iwayomogi inhibits LPS-induced microglial activation. The present study aims to identify chemical constituents with anti-neuroinflammatory properties in [...] Read more.
Neuroinflammation, predominantly mediated by microglial activation, is a key immunological response in the pathogenesis of neurodegenerative disorders. In our preliminary study, the aerial part of Artemisia iwayomogi inhibits LPS-induced microglial activation. The present study aims to identify chemical constituents with anti-neuroinflammatory properties in the aerial parts of A. iwayomogi. Two new guaianolide sesquiterpenes, iwayomogins A and B (1 and 2), along with thirteen known sesquiterpene lactones (315), one diterpene glycoside (16), and nine phenolic compounds (1725) were isolated from the aerial parts of A. iwayomogi by repeated chromatography. The structures of the isolates were elucidated by their spectroscopic data. All isolates were evaluated for their inhibitory activities on nitric oxide (NO) production in LPS-induced BV-2 microglial cells. 2,3-Dehydro-1-epi-asperilin (11) exhibited the strongest inhibitory effect on NO production (IC50 value of 1.78 μM). In the molecular docking study, three compounds (1, 2, and 11) showed good binding affinities with iNOS. Additionally, compounds 1, 2, and 11 inhibit pro-inflammatory cytokines (TNF-α and IL-6) in dose-dependent manners. The present study demonstrates that the chemical constituents from A. iwayomogi inhibit NO production and pro-inflammatory cytokine release in BV-2 cells. However, further evaluation with biological experiments utilizing in vivo models is necessary. Full article
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7 pages, 1437 KiB  
Article
Dual Beneficial Effects of Methylnissolin-3-O-β-d-Glucopyranoside on Obesity-Induced Inflammatory Responses in Adipocyte-Macrophage Co-Culture
by Dahae Lee, Xiaohua Wu, Ingo Lange, Shugeng Cao and Ki Sung Kang
Plants 2022, 11(13), 1715; https://doi.org/10.3390/plants11131715 - 28 Jun 2022
Cited by 1 | Viewed by 1453
Abstract
Methylnissolin-3-O-β-d-glucopyranoside (MNG) is a pterocarpan analog, which protects EA.hy926 cells against oxidative damage through the Nrf2/HO-1 pathway. However, the effects of MNG on obesity-induced inflammatory responses in adipocyte-macrophage co-culture remain unclear. A differentiated murine preadipocyte cell line (3T3-L1) was co-cultured with [...] Read more.
Methylnissolin-3-O-β-d-glucopyranoside (MNG) is a pterocarpan analog, which protects EA.hy926 cells against oxidative damage through the Nrf2/HO-1 pathway. However, the effects of MNG on obesity-induced inflammatory responses in adipocyte-macrophage co-culture remain unclear. A differentiated murine preadipocyte cell line (3T3-L1) was co-cultured with a murine macrophage cell line (RAW264.7). Intracellular lipid accumulation was determined using Oil Red O staining. Western blotting was performed to investigate the expression of adipogenesis- and inflammation-associated proteins. Cell culture supernatants were assayed using ELISA kits to measure the levels of proinflammatory cytokines such as interleukin 6 (IL-6) and monocyte chemoattractant protein-1 (MCP-1). MNG inhibited lipid accumulation and the production of IL-6 and MCP-1 in the 3T3-L1 and RAW264.7 cell co-culture. Moreover, MNG inhibited the protein expression of CCAAT/enhancer-binding protein alpha (C/EBPα), C/EBPβ, peroxisome proliferator-activated receptor γ (PPARγ), cyclooxygenase 2 (COX-2), and inducible nitric oxide synthase (iNOS) under the same co-culture conditions. MNG also inhibited IL-6 and MCP-1 production compared with the co-culture control. These findings demonstrate that MNG inhibited lipid accumulation and inflammatory response by downregulating IL-6 and MCP-1 production and protein expression of C/EBPβ, C/EBPα, PPARγ, COX-2, and iNOS in co-culture conditions with 3T3-L1 and RAW264.7 cells. These results suggest that MNG may be beneficial in preventing obesity-related inflammatory status. Full article
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16 pages, 4269 KiB  
Article
Brevilin A Isolated from Centipeda minima Induces Apoptosis in Human Gastric Cancer Cells via an Extrinsic Apoptotic Signaling Pathway
by Dahae Lee, Hee Jae Kwak, Byoung Ha Kim, Dong-Wook Kim, Hyun Young Kim, Seung Hyun Kim and Ki Sung Kang
Plants 2022, 11(13), 1658; https://doi.org/10.3390/plants11131658 - 23 Jun 2022
Cited by 10 | Viewed by 1981
Abstract
Brevilin A, which has anticancer activities against a range of cancers, is an abundant constituent of the medicinal herb Centipeda minima (L.) A. Braun & Asch, which has also been reported to have anticancer activity against breast cancer cells. However, the anticancer activities [...] Read more.
Brevilin A, which has anticancer activities against a range of cancers, is an abundant constituent of the medicinal herb Centipeda minima (L.) A. Braun & Asch, which has also been reported to have anticancer activity against breast cancer cells. However, the anticancer activities of C. minima and brevilin A against human gastric cancer have yet to be reported. In this study, we aimed to evaluate the cytotoxicity and molecular basis underlying the anticancer activities of extracts of C. minima (CMX) and brevilin A against human gastric cancer (AGS) cells. We deduced the potential targets and mechanisms underlying the anticancer activity of brevilin A based on a network pharmacology approach. CCND1, CDK4, and BCL2L1 were identified as the key anticancer genes targeted by brevilin A. Cytotoxicity analyses revealed that CMX and brevilin A reduced the viability of AGS cells to levels below 50% (9.73 ± 1.29 µg/mL and 54.69 ± 1.38 μM, respectively). Furthermore, Hoechst 33342, annexin V, and propidium iodide staining and western blot analyses revealed that CMX and brevilin A promoted a significant induction of apoptotic cell death by upregulating the expression of cleaved caspase-8 and cleaved caspase-3 and reducing the ratio of Bax to Bcl-2, which is partially consistent with the findings of our network pharmacology analysis. Collectively, our observations indicate that CMX and brevilin A are novel sources of herbal medicine with potential utility as effective agents for the treatment of gastric cancer. Full article
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12 pages, 1881 KiB  
Article
Chemical Constituents of the Flowers of Pueraria lobata and Their Cytotoxic Properties
by Yejin Kim, Jaeyoon Kim, So-Ri Son, Ji-Young Kim, Jung-Hye Choi and Dae Sik Jang
Plants 2022, 11(13), 1651; https://doi.org/10.3390/plants11131651 - 22 Jun 2022
Cited by 6 | Viewed by 1992
Abstract
The flower of Pueraria lobata (Puerariae Flos) is a reddish-purple to violet-purple flower that blooms between July and September. In our preliminary study, Puerariae Flos extract exhibited significant activity against a human ovarian cancer cell line. This research aims to identify the active [...] Read more.
The flower of Pueraria lobata (Puerariae Flos) is a reddish-purple to violet-purple flower that blooms between July and September. In our preliminary study, Puerariae Flos extract exhibited significant activity against a human ovarian cancer cell line. This research aims to identify the active compounds in Pueraria Flos. By repeated chromatography, one new tryptophan derivative (1), two new flavanones (4 and 5), and 19 known compounds, including tryptophan derivatives (2 and 3), flavonoids (69), isoflavonoids (1020), a flavonolignan (21), and a phenolic compound (22), were isolated from a methanol extract of Puerariae Flos. The structures of new compounds were elucidated as 13-N-benzoyl-l-tryptophan-1-N-β-d-glucopyranoside (1), 2-hydroxy-5-methoxy-naringenin (4), and 2-hydroxy-5-methoxy-naringenin 7-O-β-d-glucopyranoside (5). Among the isolates, afromosin (17), tectorigenin (11), apigenin (8), glycitein (16), (-)-hydnocarpin (21), irilin D (12), irisolidone 7-O-glucoside (14), and genistein (10) showed cytotoxicity against human ovarian cancer cell line A2780. Apigenin (8) and (-)-hydnocarpin (21) were the most active (IC50 values of 9.99 and 7.36 μM, respectively). Full article
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