Trichothecene and tremulane sesquiterpenes from a hallucinogenic mushroom Gymnopilus junonius and their cytotoxicity

Lee, Seulah; Ryoo, Rhim; Choi, Jin Hee; Kim, Jeong‐Han; Kim, Seon Hee; Kim, Ki‐Hyun

doi:10.1007/s12272-020-01213-6

Cited by 61 publications

(40 citation statements)

References 40 publications

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“…Cell viability was assessed using the MTT assay with some modifications [55][56][57][58][59]. Briefly, cell were seeded in 96-well plates (2 × 10 4 cell/well) and treated with 0.5% DMSO (control), 10 μM quercetin (positive control), or different concentrations of the crude extract of white mulberry fruit (50-150 μg/mL) and the EA (5-20 μg/mL), BuOH (10-50 μg/mL), HX, (5-20 μg/mL), and MC (5-30 μg/mL) fractions in the absence or presence of LPS (2 μg/mL in PBS) for 24 h. Following treatment, 20 μL MTT solution (5 mg/mL in PBS) was added to each well, and the plates were incubated at 37 °C in an atmosphere of 5% CO2 for 2 h. Then, the supernatant was removed, and 100 μL DMSO was added to each well to dissolve any formazan crystals that developed.…”

Section: Cell Viabilitymentioning

confidence: 99%

Antioxidant and Anti-Inflammatory Effects of White Mulberry (Morus alba L.) Fruits on Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Lim

Lee

et al. 2021

Molecules

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In this study, the protective effects of white mulberry (Morus alba) fruits on lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages were investigated. The ethanol (EtOH) extract of white mulberry fruits and its derived fractions contained adequate total phenolic and flavonoid contents, with good in vitro antioxidant radical scavenging activity. The extract and fractions also markedly inhibited ROS generation and antioxidant activity. After treatment with the EtOH extract and its fractions, LPS stimulation-induced elevated nitric oxide (NO) production was restored, which was primarily mediated by downregulation of inducible NO synthase expression. A total of 20 chemical constituents including flavonoids, steroids, and phenolics were identified in the fractions using ultra-high-performance liquid chromatography (UHPLC)-quadrupole time-of-flight (QTOF) high-resolution mass spectrometry (HRMS). These findings provide experimental evidence of the protective effects of white mulberry fruit extract against oxidative stress and inflammatory responses, suggesting their nutraceutical and pharmaceutical potential as natural antioxidant and anti-inflammatory agents.

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Section: Cell Viabilitymentioning

confidence: 99%

Antioxidant and Anti-Inflammatory Effects of White Mulberry (Morus alba L.) Fruits on Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Lim

Lee

et al. 2021

Molecules

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“…In this context, as a part of continuous research programs to discover structurally new bioactive compounds from diverse natural sources [ 13 , 14 , 15 , 16 , 17 , 18 , 19 ], our group has focused on the potential bioactive composition of H. rhamnoides fruits. In our recent study of H. rhamnoides fruits, we identified six chemical compounds, including one citric acid derivative, two flavonoids, one phenolic compound, and two megastigmane derivatives, which were evaluated for their anti-inflammatory effects by determining LPS-induced NO production in RAW 264.7 cells [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

Phytochemical Analysis of the Fruits of Sea Buckthorn (Hippophae rhamnoides): Identification of Organic Acid Derivatives

Lee

Jang

Park

et al. 2021

Plants

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Hippophae rhamnoides L. (Elaeagnaceae), commonly known as “Sea buckthorn” and “Vitamin tree”, is a spiny deciduous shrub whose fruit is known for its nutritional composition, such as vitamin C, and is consumed as a dietary supplement worldwide. As part of our ongoing efforts to identify structurally new and bioactive constituents from natural resources, the phytochemical investigation of the extract of H. rhamnoides fruits led to the isolation of one malate derivative (1), five citrate derivatives (2–6), and one quinate derivative (7). The structures of the isolated compounds were elucidated by analysis of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization (HR-ESI) liquid chromatography–mass spectrometry (LC/MS) data. Three of the citrate derivatives were identified as new compounds: (S)-1-butyl-5-methyl citrate (3), (S)-1-butyl-1′-methyl citrate (4), and (S)-1-methyl-1′-butyl citrate (6), which turned out to be isolation artifacts. The absolute configurations of the new compounds were established by quantum chemical electronic circular dichroism (ECD) calculation, which is an informative tool for verifying the absolute configuration of organic acid derivatives. The isolated compounds 1–7 were evaluated for their stimulatory effects on osteogenesis. Compounds 1, 3, 4, 6, and 7 stimulated osteogenic differentiation up to 1.4 fold, compared to the negative control. These findings provide experimental evidence that active compounds 1, 3, 4, 6, and 7 induce the osteogenesis of mesenchymal stem cells and activate bone formation.

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“…Tremulanes, a family of sesquiterpenoids with characteristic structures of 5/7 fused bicyclic system, were rarely discovered in nature until 2015 (Guo et al, 2016). However, from 2016 to 2020, about 60 tremulane derivatives were found (Guo et al, 2016;Isaka et al, 2016;Wu, 2016;Chen et al, 2017Chen et al, , 2018Cong et al, 2020;Wang et al, 2017Wang et al, , 2020Ding et al, 2018Ding et al, , 2019Ding et al, , 2020aZhou et al, 2018;Duan et al, 2019;Wu et al, 2019Wu et al, , 2020He et al, 2020;Lee et al, 2020;Shi et al, 2020;, and the number is twice as many as before. Most of them were isolated from the cultures of the basidiomycetes Irpex lacteus (Chen et al, 2018(Chen et al, , 2020Ding et al, 2018Ding et al, , 2019Ding et al, , 2020aZhou et al, 2018;Duan et al, 2019;Wu et al, 2019;Shi et al, 2020;Wang et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

Sesquiterpenoids From the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11

Shi

Zheng

et al. 2021

Front. Microbiol.

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The fungal strains Pseudogymnoascus are a kind of psychrophilic pathogenic fungi that are ubiquitously distributed in Antarctica, while the studies of their secondary metabolites are infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11 led to the isolation of six new tremulane sesquiterpenoids pseudotremulanes A–F (1–6), combined with one known analog 11,12-epoxy-12β-hydroxy-1-tremulen-5-one (7), and five known steroids (8–12). The absolute configurations of the new compounds (1–6) were elucidated by their ECD spectra and ECD calculations. Compounds 1–7 were proved to be isomeride structures with the same chemical formula. Compounds 1/2, 3/4, 1/4, and 2/3 were identified as four pairs of epimerides at the locations of C-3, C-3, C-9, and C-9, respectively. Compounds 8 and 9 exhibited cytotoxic activities against human breast cancer (MDA-MB-231), colorectal cancer (HCT116), and hepatoma (HepG2) cell lines. Compounds 9 and 10 also showed antibacterial activities against marine fouling bacteria Aeromonas salmonicida. This is the first time to find terpenoids and steroids in the fungal genus Pseudogymnoascus.

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Trichothecene and tremulane sesquiterpenes from a hallucinogenic mushroom Gymnopilus junonius and their cytotoxicity

Cited by 61 publications

References 40 publications

Antioxidant and Anti-Inflammatory Effects of White Mulberry (Morus alba L.) Fruits on Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Antioxidant and Anti-Inflammatory Effects of White Mulberry (Morus alba L.) Fruits on Lipopolysaccharide-Stimulated RAW 264.7 Macrophages

Phytochemical Analysis of the Fruits of Sea Buckthorn (Hippophae rhamnoides): Identification of Organic Acid Derivatives

Sesquiterpenoids From the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11

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