Cytotoxic activities of sesquiterpenoids from the aerial parts of Petasites japonicus against cancer stem cells

Μatsumoto, Takahiro; Imahori, Daisuke; Saito, Youhei; Zhang, Wei; Ohta, Tomoe; Yoshida, Tatsusada; Nakayama, Yuji; Ashihara, Eishi; Watanabe, Tetsushi

doi:10.1007/s11418-020-01420-x

Cited by 22 publications

(15 citation statements)

References 26 publications

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“…Eremophilane sesquiterpenes, consisting of three isoprenes, possess the identical decalin framework with the eudesmanes and probably belong to a small group of sesquiterpenes. , Eremophilane sesquiterpenoids widely existed in numerous medicinal plants, especially in the Asteraceae family. − Subsequently, the metabolites of eremophilanes produced by theendophytic and marine fungi have increased remarkably, with some exhibiting multiple bioactivities including antifungal, anti-inflammatory, antivirus, antibacterial, and insecticidal activities. − Owing to the structural diversiform and unique biological activities of eremophilane sesquiterpenes, extensive phytochemical and biological investigations have been carried out by numerous scientists. − Consequently, further studies toward the development of novel and medicinally valuable sesquiterpenoids are essential.…”

Section: Introductionmentioning

confidence: 99%

Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus Septoria rudbeckiae

Lin

Zhang

Han

et al. 2021

J. Agric. Food Chem.

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Fourteen eremophilane sesquiterpenoids (1–14), including nine new congeners, septoreremophilanes A–I (1–9), together with three known sesquiterpenes (15–17), two known tetralone derivatives (18, 19), and two known cholesterol analogues (20, 21), were isolated from the endophytic fungus Septoria rudbeckiae. Compounds 1–6 and 7a belong to the family of the highly oxygenated eremophilane sesquiterpenoids with a 6/6/5 tricyclic system and bearing a hemiacetal moiety. The inhibitions of all metabolites against eight bacteria were estimated in vitro, and nine new metabolites (1–9) were tested for antineuroinflammatory activity. Notably, the effects of 4 against Pseudomonas syringae pv. actinidae and 20 against Bacillus cereus displayed potent inhibitory, with the MIC values of 6.25 and 6.25 μM, respectively. Further, scanning electron microscopy analyses indicated that 4 and 20 were to change the outer configuration of bacterial cells, respectively, and the investigations demonstrated that 4 and 20 may act as potential structure templates for the development of the agrochemical bactericides. Additionally, compound 6 displayed potent inhibition of NO generation in lipopolysaccharide-induced BV-2 microglial cells (IC50 = 12.0 ± 0.32 μM), and the conceivable anti-inflammatory mechanisms implicated were also investigated by molecular docking. Thus, the bioactive metabolites of the strain S. rudbeckiae may serve as a novel resource to be developed.

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Section: Introductionmentioning

confidence: 99%

Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus Septoria rudbeckiae

Lin

Zhang

Han

et al. 2021

J. Agric. Food Chem.

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“…All test compounds were evaluated their cytotoxicity by using CellTiter-Glo 3D® cell viability assay ( Matsumoto et al, 2020 ). Briefly, Vero cells (3.0 × 10 3 cells/ well) were seeded in 96-well plates (96F Nunclon TM Delta Microwell SI; Thermo Fisher Scientific), and precultured for 24 h. The cells were treated with test compounds (10 μ L/well).…”

Section: Methodsmentioning

confidence: 99%

Effective Search of Triterpenes with Anti-HSV-1 Activity Using a Classification Model by Logistic Regression

et al. 2021

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Natural products are an excellent source of skeletons for medicinal seeds. Triterpenes and saponins are representative natural products that exhibit anti-herpes simplex virus type 1 (HSV-1) activity. However, there has been a lack of comprehensive information on the anti-HSV-1 activity of triterpenes. Therefore, expanding information on the anti-HSV-1 activity of triterpenes and improving the efficiency of their exploration are urgently required. To improve the efficiency of the development of anti-HSV-1 active compounds, we constructed a predictive model for the anti-HSV-1 activity of triterpenes by using the information obtained from previous studies using machine learning methods. In this study, we constructed a binary classification model (i.e., active or inactive) using a logistic regression algorithm. As a result of the evaluation of predictive model, the accuracy for the test data is 0.79, and the area under the curve (AUC) is 0.86. Additionally, to enrich the information on the anti-HSV-1 activity of triterpenes, a plaque reduction assay was performed on 20 triterpenes. As a result, chikusetsusaponin IVa (11: IC50 = 13.06 μM) was found to have potent anti-HSV-1 with three potentially anti-HSV-1 active triterpenes. The assay result was further used for external validation of predictive model. The prediction of the test compounds in the activity test showed a high accuracy (0.83) and AUC (0.81). We also found that this predictive model was found to be able to successfully narrow down the active compounds. This study provides more information on the anti-HSV-1 activity of triterpenes. Moreover, the predictive model can improve the efficiency of the development of active triterpenes by integrating many previous studies to clarify potential relationships.

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“…Previous reports have shown that owing to its biological activities, PJ exhibits wide-ranging beneficial therapeutic effects including anticancer [ 22 , 23 ], antiallergy [ 24 ], anti-inflammatory [ 25 ], and antioxidative activities [ 26 ]. Although the antitumor ability of compounds and/or extracts from PJ has been investigated [ 20 , 22 , 23 , 27 , 28 ], the specific immunological role of PJ-EVs has not yet been established.…”

Section: Introductionmentioning

confidence: 99%

Immunostimulatory Potential of Extracellular Vesicles Isolated from an Edible Plant, Petasites japonicus, via the Induction of Murine Dendritic Cell Maturation

Han

Song

Lim

et al. 2021

IJMS

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Extracellular vesicles (EVs) have recently been isolated from different plants. Plant-derived EVs have been proposed as potent therapeutics and drug-delivery nanoplatforms for delivering biomolecules, including proteins, RNAs, DNAs, and lipids. Herein, Petasites japonicus-derived EVs (PJ-EVs) were isolated through a series of centrifugation steps and characterized using dynamic light scattering and transmission electron microscopy. Immunomodulatory effects of PJ-EVs were assessed using dendritic cells (DCs). PJ-EVs exhibited a spherical morphology with an average size of 122.6 nm. They induced the maturation of DCs via an increase in the expression of surface molecules (CD80, CD86, MHC-I, and MHC-II), production of Th1-polarizing cytokines (TNF-α and IL-12p70), and antigen-presenting ability; however, they reduced the antigen-uptake ability. Furthermore, maturation of DCs induced by PJ-EVs was dependent on the activation and phosphorylation of MAPK and NF-κB signal pathways. Notably, PJ-EV-treated DCs strongly induced the proliferation and differentiation of naïve T cells toward Th1-type T cells and cytotoxic CD8+ T cells along with robust secretion of IFN-γ and IL-2. In conclusion, our study indicates that PJ-EVs can be potent immunostimulatory candidates with an ability of strongly inducing the maturation of DCs.

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Cytotoxic activities of sesquiterpenoids from the aerial parts of Petasites japonicus against cancer stem cells

Cited by 22 publications

References 26 publications

Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus Septoria rudbeckiae

Eremophilane Sesquiterpenoids with Antibacterial and Anti-inflammatory Activities from the Endophytic Fungus Septoria rudbeckiae

Effective Search of Triterpenes with Anti-HSV-1 Activity Using a Classification Model by Logistic Regression

Immunostimulatory Potential of Extracellular Vesicles Isolated from an Edible Plant, Petasites japonicus, via the Induction of Murine Dendritic Cell Maturation

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