Structurally Diverse Sesquiterpenoids with Anti-neuroinflammatory Activity from the Endolichenic Fungus Cryptomarasmius aucubae

Two new phomaligols, deketo-phomaligol A (1) and phomaligol E (2), together with six known compounds (3–8) were isolated from the culture broth of the marine-derived fungus Aspergillus flocculosus. Compound 1 was first isolated as a phomaligol derivative possessing a five-membered ring. The structures and absolute configurations of the new phomaligols were determined by detailed analyses of mass spectrometry (MS), nuclear magnetic resonance (NMR) data, optical rotation values and electronic circular dichroism (ECD). In addition, the absolute configurations of the known compounds 3 and 4 were confirmed by chemical oxidation and comparison of optical rotation values. Isolated compounds at a concentration of 100 μM were screened for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. Among the compounds, 4 showed moderate anti-neuroinflammatory effects with an IC50 value of 56.6 μM by suppressing the production of pro-inflammatory mediators in activated microglial cells without cytotoxicity.

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Saccharpiscinols A–C: Flavans with Potential Inflammatory Activities from One Actinobacteria Saccharomonospora piscinae

Molecules ◽

10.3390/molecules26164909 ◽

2021 ◽

Vol 26 (16) ◽

pp. 4909

Author(s):

Yung-Shun Su ◽

Jih-Jung Chen ◽

Ming-Jen Cheng ◽

Chee-Yin Chai ◽

Aij-Lie Kwan ◽

...

Keyword(s):

Data Analysis ◽

Chromatographic Separation ◽

Spectroscopic Data ◽

2D Nmr ◽

No Production ◽

Raw 264.7 ◽

Phytochemical Investigation ◽

Inhibitory Activities ◽

New Compounds ◽

First Time

Phytochemical investigation and chromatographic separation of extracts from the actinobacteria strain Saccharomonospora piscinae that was isolated from dried fishpond sediment of Kouhu township, in the south of Taiwan, led to the isolation of three new compounds, saccharpiscinols A–C (1–3, respectively), and three new natural products, namely (2S)-5,7,3′,4′-tetrahydroxy-6,8-dimethylflavanone (4), methyl-4-hydroxy-2-methoxy-6-methylbenzoate (5), and (±)-7-acetyl-4,8-dihydroxy-6-methyl-1-tetralone (6). Compounds 4–6 were reported before as synthesized products, herein, they are reported from nature for the first time. The structures of the new compounds were unambiguously elucidated on the basis of extensive spectroscopic data analysis (1D- and 2D-NMR, MS, and UV) and comparison with literature data. The effect of some isolates on the inhibition of NO production in lipopolysaccharide-activated RAW 264.7 murine macrophages was evaluated. Saccharpiscinol A showed inhibitory activities against LPS-induced NO production.

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Monomeric and Dimeric Bromophenols from the Red Alga Ceramium Sp. with Antioxidant and Anti-Inflammatory Activities

10.26434/chemrxiv.12760352 ◽

2020 ◽

Author(s):

Yi Zhang ◽

Evgenia Glukhov ◽

Haobin Yu ◽

Lena Gerwick ◽

Pieter Dorrestein ◽

...

Keyword(s):

Nitric Oxide ◽

Spectroscopic Data ◽

Optical Rotation ◽

Red Alga ◽

Isopropyl Ether ◽

Specific Optical Rotation ◽

Extensive Analysis ◽

Red Algal ◽

Anti Inflammatory ◽

Brominated Compounds

LC-MS2-based molecular networking using the Global Natural Products Social (GNPS) tool revealed a rich assortment of brominated compounds present in the antioxidant fraction of a red algal extract (Ceramium sp.) Further chemical investigation led to discovery of one monomeric bromophenol (lanosol isopropyl ether, 1) and seven dimeric ones (bromourceolatols A-G, 2-8), all of which are previously undescribed. Their structures were elucidated by extensive analysis of their spectroscopic data. Compounds 2-8 were determined to be racemic trans-type isomers by NOESY, specific optical rotation, and ECD. Compounds 1 and 3 displayed antioxidant activity with their EC50 of 44.4 and 47.0 μM, respectively, for scavenging DPPH free radicals while compounds 2 and 4 had approximate EC50 values of ~ 64 μM. Furthermore, compounds 2, 3, and 7 exhibited relatively potent anti-inflammatory activity at 32 μM by quenching 97%, 47%, and 73% of nitric oxide induced by bacterial lipopolysaccharide in macrophage RAW264.7 cells, respectively.

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Monomeric and Dimeric Bromophenols from the Red Alga Ceramium Sp. with Antioxidant and Anti-Inflammatory Activities

10.26434/chemrxiv.12760352.v1 ◽

2020 ◽

Author(s):

Yi Zhang ◽

Evgenia Glukhov ◽

Haobin Yu ◽

Lena Gerwick ◽

Pieter Dorrestein ◽

...

Keyword(s):

Nitric Oxide ◽

Spectroscopic Data ◽

Optical Rotation ◽

Red Alga ◽

Isopropyl Ether ◽

Specific Optical Rotation ◽

Extensive Analysis ◽

Red Algal ◽

Anti Inflammatory ◽

Brominated Compounds

LC-MS2-based molecular networking using the Global Natural Products Social (GNPS) tool revealed a rich assortment of brominated compounds present in the antioxidant fraction of a red algal extract (Ceramium sp.) Further chemical investigation led to discovery of one monomeric bromophenol (lanosol isopropyl ether, 1) and seven dimeric ones (bromourceolatols A-G, 2-8), all of which are previously undescribed. Their structures were elucidated by extensive analysis of their spectroscopic data. Compounds 2-8 were determined to be racemic trans-type isomers by NOESY, specific optical rotation, and ECD. Compounds 1 and 3 displayed antioxidant activity with their EC50 of 44.4 and 47.0 μM, respectively, for scavenging DPPH free radicals while compounds 2 and 4 had approximate EC50 values of ~ 64 μM. Furthermore, compounds 2, 3, and 7 exhibited relatively potent anti-inflammatory activity at 32 μM by quenching 97%, 47%, and 73% of nitric oxide induced by bacterial lipopolysaccharide in macrophage RAW264.7 cells, respectively.

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Bioactive Polyketides From the Potato Endophytic Fungus Aspergillus carneus

Natural Product Communications ◽

10.1177/1934578x20985222 ◽

2020 ◽

Vol 15 (12) ◽

pp. 1934578X2098522

Author(s):

Xian Zhang ◽

Fa-Lei Zhang ◽

Xing Wu ◽

Ke Ye ◽

Xiao Lv ◽

...

Keyword(s):

Nitric Oxide ◽

Nuclear Magnetic Resonance ◽

Antioxidant Activity ◽

Endophytic Fungus ◽

Spectroscopic Data ◽

Plant Pathogens ◽

Inhibitory Concentration ◽

Optical Rotation ◽

Nitric Oxide Production ◽

Effective Antioxidant

A previously undescribed polyketide (1) and 3 known analogs (2-4) were obtained from cultures of the potato endophytic fungus Aspergillus carneus. The structures were elucidated on the basis of extensive nuclear magnetic resonance spectroscopic data. The absolute conﬁguration of 1 was further determined by electronic circular dichroism and optical rotation calculations. Compounds 1-4 showed moderate antifungal activity against plant pathogens. Compounds 1, 2, and 4 inhibited nitric oxide production in lipopolysaccharide-stimulated RAW264.7 cells, with half-maximal inhibitory concentration values of 13.36, 30.16, and 51.47 µM, respectively. Compound 4 showed effective antioxidant activity.

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Cytochalasins from Xylaria sp. CFL5, an Endophytic Fungus of Cephalotaxus fortunei

Natural Products and Bioprospecting ◽

10.1007/s13659-020-00279-5 ◽

2020 ◽

Author(s):

Kai-Liang Ma ◽

Shi-Hui Dong ◽

Hang-Ying Li ◽

Wen-Jun Wei ◽

Yong-Qiang Tu ◽

...

Keyword(s):

Endophytic Fungus ◽

Spectroscopic Data ◽

Biological Activities ◽

Optical Rotation ◽

Ags Cells ◽

Mhc Ii ◽

Chemical Structures ◽

Data Analyses ◽

Binding Inhibition ◽

New Compounds

Abstract Three previously undescribed cytochalasins, named xylariasins A‒C (1‒3), together with six known ones (4‒9) were isolated from Xylaria sp. CFL5, an endophytic fungus of Cephalotaxus fortunei. The chemical structures of all new compounds were elucidated on the basis of extensive spectroscopic data analyses and electronic circular dichroism calculation, as well as optical rotation calculation. Biological activities of compounds 1, 4‒9 were evaluated, including cytotoxic, LAG3/MHC II binding inhibition and LAG3/FGL1 binding inhibition activities. Compounds 6 and 9 possessed cytotoxicity against AGS cells at 5 μM, with inhibition rates of 94% and 64%, respectively. In addition, all tested isolates, except compound 6, exhibited obvious inhibitory activity against the interaction of both LAG3/MHC II and LAG3/FGL1. Compounds 1, 5, 7, and 8 inhibited LAG3/MHC II with IC50 values ranging from 2.37 to 4.74 μM. Meanwhile, the IC50 values of compounds 1, 7, and 8 against LAG3/FGL1 were 11.78, 4.39, and 7.45 μM, respectively. Graphic Abstract

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Isolation of Novel Sesquiterpeniods and Anti-neuroinflammatory Metabolites from Nardostachys jatamansi

Molecules ◽

10.3390/molecules23092367 ◽

2018 ◽

Vol 23 (9) ◽

pp. 2367 ◽

Cited By ~ 6

Author(s):

Chi-Su Yoon ◽

Dong-Cheol Kim ◽

Jin-Soo Park ◽

Kwan-Woo Kim ◽

Youn-Chul Kim ◽

...

Keyword(s):

Nitric Oxide ◽

Signaling Pathway ◽

2D Nmr ◽

Microglial Cells ◽

No Production ◽

Nardostachys Jatamansi ◽

Tnf Α ◽

Factor Α ◽

Oxide Synthase ◽

Bv2 Microglial Cells

Nardostachys jatamansi contains various types of sesquiterpenoids that may play an important role in the potency of plant’s anti-inflammatory effects, depending on their structure. In this study, five new sesquiterpenoids, namely kanshone L (1), kanshone M (2), 7-methoxydesoxo-narchinol (3), kanshone N (4), and nardosdaucanol (5), were isolated along with four known terpenoids (kanshone D (6), nardosinanone G (7), narchinol A (8), and nardoaristolone B (9)) from the rhizomes and roots of Nardostachys jatamansi. Their structures were determined by analyzing 1D and 2D NMR and MS data. Among the nine sesquiterpenoids, compounds 3, 4, and 8 were shown to possess dose-dependent inhibitory effects against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in BV2 microglial cells. Furthermore, compounds 3, 4, and 8 exhibited anti-neuroinflammatory effects by inhibiting the production of pro-inflammatory mediators, including prostaglandin E2 (PGE2), inducible nitric oxide synthase (iNOS), and cyclooxygenase-2 (COX-2) proteins, as well as pro-inflammatory cytokines, such as interleukin (IL)-1β, IL-12 and tumor necrosis factor-α (TNF-α), in LPS-stimulated BV2 microglial cells. Moreover, these compounds were shown to inhibit the activation of the NF-κB signaling pathway in LPS-stimulated BV2 microglial cells by suppressing the phosphorylation of IκB-α and blocking NF-κB translocation. In conclusion, five new and four known sesquiterpenoids were isolated from Nardostachys jatamansi, and compounds 3, 4, and 8 exhibited anti-neuroinflammatory effects in LPS-stimulated BV2 microglial cells through inhibiting of NF-κB signaling pathway.

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Antineuroinflammatory constituents from the root extract of Paris verticillata

Canadian Journal of Chemistry ◽

10.1139/v10-166 ◽

2011 ◽

Vol 89 (4) ◽

pp. 441-445 ◽

Cited By ~ 3

Author(s):

Ki Hyun Kim ◽

Kyu Ha Lee ◽

Ho Kyung Kim ◽

Eunjung Moon ◽

Sung-Hoon Kim ◽

...

Keyword(s):

Nitric Oxide ◽

Fatty Acid ◽

Cell Line ◽

Spectroscopic Data ◽

2D Nmr ◽

No Production ◽

Root Extract ◽

Meoh Extract ◽

Microglia Cell ◽

Chemical Evidence

Two new cyclopropanoic fatty acid glycosides, named parisveroside A (1) and parisveroside B (2), were isolated from a MeOH extract of the roots of Paris verticillata (Liliaceae) together with three other known compounds, salicin (3), 3-(β-d-glucopyranosyloxymethyl)-2-(4-hydroxy-3-methoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-(2R,3S)-dihydrobenzofuran (4), and allantoin (5). Their structures were elucidated on the basis of spectroscopic data, including 1D and 2D NMR, HR-FAB-MS, and chemical evidence. To investigate the antineuroinflammatory effects of the isolated compounds (1–5), nitric oxide (NO) production was evaluated in the lipopolysaccharide-activated microglia cell line, BV-2. Compounds 2 and 4 significantly inhibited NO production with IC50 values of 74.8 and 60.5 µmol/L, respectively.

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Four New Iridoid Metabolites Have Been Isolated from the Stems of Neonauclea reticulata (Havil.) Merr. with Anti-Inflammatory Activities on LPS-Induced RAW264.7 Cells

Molecules ◽

10.3390/molecules24234271 ◽

2019 ◽

Vol 24 (23) ◽

pp. 4271

Author(s):

Fang-Pin Chang ◽

Shyh-Shyun Huang ◽

Tzong-Huei Lee ◽

Chi-I Chang ◽

Tzong-Fu Kuo ◽

...

Keyword(s):

Nitric Oxide ◽

Detailed Analysis ◽

Cell Line ◽

Spectroscopic Data ◽

Protocatechuic Acid ◽

Control Group ◽

No Production ◽

Raw264.7 Macrophages ◽

Ic50 Values ◽

Inhibitory Activities

One new iridoid, namely neonanin C (1) one monocyclic iridoid ring-opened derivative namely neonanin D (2), two new bis-iridoid derivatives namely reticunin A (3) and reticunin B (4) with sixteen known compounds (5–20) were isolated from the stems of Neonauclea reticulata (Havil.) Merr. These new structures were determined by the detailed analysis of spectroscopic data and comparison with the data of known analogues. Compounds 1–20 were evaluated for inhibition of nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages cell line. The results showed that all compounds exhibited no obvious cytotoxicity compared to the control group and five compounds including isoboonein (7), syringaresinol (10), (+)-medioresinol (12), protocatechuic acid (14) and trans-caffeic acid (15) exhibited inhibitory activities with IC50 values at 86.27 ± 3.45; 9.18 ± 1.90; 76.18 ± 2.42; 72.91 ± 4.97 and 95.16 ± 1.20 µg/mL, respectively.

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