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

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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Metabolites with Anti-Inflammatory Activity from the Mangrove Endophytic Fungus Diaporthe sp. QYM12

Marine Drugs ◽

10.3390/md19020056 ◽

2021 ◽

Vol 19 (2) ◽

pp. 56

Author(s):

Yan Chen ◽

Ge Zou ◽

Wencong Yang ◽

Yingying Zhao ◽

Qi Tan ◽

...

Keyword(s):

Nitric Oxide ◽

Endophytic Fungus ◽

Spectroscopic Data ◽

Specific Rotation ◽

Ring System ◽

Meoh Extract ◽

Mangrove Endophytic Fungus ◽

Extensive Analysis ◽

Ic50 Values ◽

Anti Inflammatory

One new diterpenoid, diaporpenoid A (1), two new sesquiterpenoids, diaporpenoids B–C (2,3) and three new α-pyrone derivatives, diaporpyrones A–C (4–6) were isolated from an MeOH extract obtained from cultures of the mangrove endophytic fungus Diaporthe sp. QYM12. Their structures were elucidated by extensive analysis of spectroscopic data. The absolute configurations were determined by electronic circular dichroism (ECD) calculations and a comparison of the specific rotation. Compound 1 had an unusual 5/10/5-fused tricyclic ring system. Compounds 1 and 4 showed potent anti-inflammatory activities by inhibiting the production of nitric oxide (NO) in lipopolysaccharide (LPS)-induced RAW264.7 cells with IC50 values of 21.5 and 12.5 μM, respectively.

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

Natural Products and Bioprospecting ◽

10.1007/s13659-021-00299-9 ◽

2021 ◽

Author(s):

Yi-Jie Zhai ◽

Jian-Nan Li ◽

Yu-Qi Gao ◽

Lin-Lin Gao ◽

Da-Cheng Wang ◽

...

Keyword(s):

Nitric Oxide ◽

Data Analysis ◽

Spectroscopic Data ◽

Optical Rotation ◽

Ring System ◽

Microglial Cells ◽

No Production ◽

Specific Optical Rotation ◽

Endolichenic Fungus ◽

New Compounds

AbstractTwo new sterpurane sesquiterpenoids named sterpurol D (1) and sterpurol E (2), and one skeletally new sesquiterpene, cryptomaraone (3), bearing a 5,6-fused bicyclic ring system, along with five known ones, sterpurol A (4), sterpurol B (5), paneolilludinic Acid (6), murolane-2α, 9β-diol-3-ene (7) and (–)-10,11-dihydroxyfarnesol (8) were isolated from an endolichenic fungus Cryptomarasmius aucubae. The structures of the new compounds were elucidated by analysis of NMR spectroscopic spectra and HRESIMS data. The absolute configurations of 1 and 2 were established by spectroscopic data analysis and comparison of specific optical rotation, as well as the biosynthetic consideration. Additionally, compounds 1, 2, 4–6, and 8 showed significant nitric oxide (NO) production inhibition in Lipopolysaccharide (LPS)-induced BV-2 microglial cells with the IC50 values ranging from 9.06 to 14.81 μM. Graphic Abstract

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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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New Thio-Compounds and Monoterpenes With Anti-inflammatory Activities From the Fungus Aspergillus sp. CYH26

Frontiers in Microbiology ◽

10.3389/fmicb.2021.668938 ◽

2021 ◽

Vol 12 ◽

Author(s):

Guojun Pan ◽

Yanling Li ◽

Xinyu Che ◽

Dan Tian ◽

Wenjie Han ◽

...

Keyword(s):

Nitric Oxide ◽

Natural Products ◽

Spectroscopic Data ◽

Rhizosphere Soil ◽

New Family ◽

Inhibitory Activities ◽

Anti Inflammatory ◽

Aspergillus Sp ◽

Sulfur Containing

Two new thio-compounds named aspergerthinol A and B (1 and 2) and two new monoterpenes named aspergerthinacids A and B (3 and 4) were isolated from the fungus Aspergillus sp. CYH26 from the rhizosphere soil of Cynanchum bungei Decne. The structures of compounds were elucidated by spectroscopic data and quantum NMR and ECD calculations. Compounds 1 and 2 represented a new family of sulfur containing natural products with a 3-methyl-4H-cyclopenta[b]thiophen-4-one skeleton. Compounds 1–4 showed inhibitory activities against nitric oxide (NO) with IC50 values of 38.0, 19.8, 46.3, and 56.6 μM, respectively.

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New prenylated coumarins from the stems of Toddalia asiatica

RSC Advances ◽

10.1039/c7ra04794k ◽

2017 ◽

Vol 7 (49) ◽

pp. 31061-31068 ◽

Cited By ~ 8

Author(s):

Wei Li ◽

Jun-Sheng Zhang ◽

Jia-Luo Huang ◽

Min-Hong Jiang ◽

You-Kai Xu ◽

...

Keyword(s):

Spectroscopic Data ◽

Optical Rotation ◽

Specific Optical Rotation ◽

X Ray ◽

Toddalia Asiatica

Prenylated coumarins from Toddalia asiatica were established using spectroscopic data, X-ray, and ECD and specific optical rotation calculations.

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Indole-Terpenoids With Anti-inflammatory Activities From Penicillium sp. HFF16 Associated With the Rhizosphere Soil of Cynanchum bungei Decne

Frontiers in Microbiology ◽

10.3389/fmicb.2021.710364 ◽

2021 ◽

Vol 12 ◽

Author(s):

Guojun Pan ◽

Yanfen Zhao ◽

Shuang Ren ◽

Fengyang Liu ◽

Qicai Xu ◽

...

Keyword(s):

Nitric Oxide ◽

Tumor Necrosis Factor ◽

Spectroscopic Data ◽

Tumor Necrosis ◽

Tumor Necrosis Factor Α ◽

Rhizosphere Soil ◽

Raw264.7 Macrophages ◽

Anti Inflammatory ◽

Factor Α ◽

Necrosis Factor

Four new indole-terpenoids (1–4) named encindolene A, 18-O-methyl-encindolene A, encindolene B, and encindolene C, as well as three known analogs (5–7), were isolated from the fungus Penicillium sp. HFF16 from the rhizosphere soil of Cynanchum bungei Decne. The structures of compounds including absolute configurations were elucidated by spectroscopic data and electronic circular dichroism (ECD) analysis. Anti-inflammatory activity evaluation revealed that compounds 1–7 inhibit the production of nitric oxide with IC50 values of 79.4, 49.7, 81.3, 40.2, 86.7, 90.1, and 54.4 μM, respectively, and decrease the levels of tumor necrosis factor-α, interleukin-6 contents in lipopolysaccharide-induced RAW264.7 macrophages.

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