scholarly journals Polyketide Derivatives, Guhypoxylonols A–D from a Mangrove Endophytic Fungus Aspergillus sp. GXNU-Y45 That Inhibit Nitric Oxide Production

Marine Drugs ◽  
2021 ◽  
Vol 20 (1) ◽  
pp. 5
Author(s):  
Xiaoya Qin ◽  
Jiguo Huang ◽  
Dexiong Zhou ◽  
Wenxiu Zhang ◽  
Yanjun Zhang ◽  
...  

Four undescribed compounds, guhypoxylonols A (1), B (2), C (3), and D (4), were isolated from the mangrove endophytic fungus Aspergillus sp. GXNU-Y45, together with seven previously reported metabolites. The structures of 1–4 were elucidated based on analysis of HRESIMS and NMR spectroscopic data. The absolute configurations of the stereogenic carbons in 1–3 were established through a combination of spectroscopic data and electronic circular dichroism (ECD). Compounds 1–11 were evaluated for their anti-inflammatory activity. Compounds 1, 3, 4, and 6 showed an inhibitory activity against the production of nitric oxide (NO), with the IC50 values of 14.42 ± 0.11, 18.03 ± 0.14, 16.66 ± 0.21, and 21.05 ± 0.13 μM, respectively.

Marine Drugs ◽  
2021 ◽  
Vol 19 (2) ◽  
pp. 56
Author(s):  
Yan Chen ◽  
Ge Zou ◽  
Wencong Yang ◽  
Yingying Zhao ◽  
Qi Tan ◽  
...  

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.


2019 ◽  
Vol 14 (5) ◽  
pp. 1934578X1984817
Author(s):  
Tong Shen ◽  
Yongdong Wang ◽  
Zhiming Zhu ◽  
Xiujie Wang ◽  
Tian Tian

Phytochemical investigation of the fruits from Vitex kwangsiensia led to the isolation of 18 constituents, including 6 lignans (1-6), 3 diterpenoids (7-9), 2 sesquiterpenoids (10, 11), 2 triterpenoids (16, 17), and 5 other compounds. Their structures were identified by spectroscopic methods (mass spectroscopy, infrared, UV, 1-dimensional and 2-dimensional nuclear magnetic resonance) and comparison with reported data in the literatures. Among these constituents, compound 1 was a new lignan and named as vitekwangin A. The spectroscopic data of 2 was reported herein for the first time, and given a trivial name vitekwangin B. The isolated lignans, diterpenoids, and sesquiterpenoids were evaluated for their inhibitory activity to prevent nitric oxide production in lipopolysaccharide-stimulated RAW264.7 macrophages.


Planta Medica ◽  
2020 ◽  
Vol 86 (13/14) ◽  
pp. 1032-1042
Author(s):  
Jean-Bosco Jouda ◽  
Emmanuel Mfotie Njoya ◽  
Serge Alain Tanemossu Fobofou ◽  
Zong Yuan Zhou ◽  
Zhe Qiang ◽  
...  

AbstractThree previously undescribed natural products, phomopsinin A – C (1 – 3), together with three known compounds, namely, cis-hydroxymellein (4), phomoxanthone A (5) and cytochalasin L-696,474 (6), were isolated from the solid culture of Phomopsis sp. CAM212, an endophytic fungus obtained from Garcinia xanthochymus. Their structures were determined on the basis of spectroscopic data, including IR, NMR, and MS. The absolute configurations of 1 and 2 were assigned by comparing their experimental and calculated ECD spectra. Acetylation of compound 1 yielded 1a, a new natural product derivative that was tested together with other isolated compounds on lipopolysaccharide-stimulated RAW 264.7 cells. Cytochalasin L-696,474 (6) was found to significantly inhibit nitric oxide production, but was highly cytotoxic to the treated cells, whereas compound 1 slightly inhibited nitric oxide production, which was not significantly different compared to lipopolysaccharide-treated cells. Remarkably, the acetylated derivative of 1, compound 1a, significantly inhibited nitric oxide production with an IC50 value of 14.8 µM and no cytotoxic effect on treated cells, thereby showing the importance of the acetyl group in the anti-inflammatory activity of 1a. The study of the mechanism of action revealed that 1a decreases the expression of inducible nitric oxide synthase, cyclooxygenase 2, and proinflammatory cytokine IL-6 without an effect on IL-1β expression. Moreover, it was found that 1a exerts its anti-inflammatory activity in lipopolysaccharide-stimulated RAW 264.7 macrophage cells by downregulating the activation of ERK1/2 and by preventing the translocation of nuclear factor κB. Thus, derivatives of phomopsinin A (1), such as compound 1a, could provide new anti-inflammatory leads.


2020 ◽  
Vol 15 (12) ◽  
pp. 1934578X2098522
Author(s):  
Xian Zhang ◽  
Fa-Lei Zhang ◽  
Xing Wu ◽  
Ke Ye ◽  
Xiao Lv ◽  
...  

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.


2021 ◽  
pp. 1-5
Author(s):  
Isaraporn Polbuppha ◽  
Virayu Suthiphasilp ◽  
Tharakorn Maneerat ◽  
Rawiwan Charoensup ◽  
Thunwadee Limtharakul ◽  
...  

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5843
Author(s):  
Shaila Mehwish ◽  
Sanjay Varikuti ◽  
Mubarak Ali Khan ◽  
Tariq Khan ◽  
Imdad Ullah Khan ◽  
...  

Natural products from plants contain many interesting biomolecules. Among them, quercetin (Q), gallic acid (GA), and rutin (R) all have well-reported antileishmanial activity; however, their exact mechanisms of action are still not known. The current study is a step forward towards unveil the possible modes of action of these compounds against Leishmania donovani (the causative agent of visceral leishmaniasis). The selected compounds were checked for their mechanisms of action against L. donovani using different biological assays including apoptosis and necrosis evaluation, effects on genetic material (DNA), quantitative testing of nitric oxide production, ultrastructural modification via transmission electron microscopy, and real-time PCR analysis. The results confirmed that these compounds are active against L. donovani, with IC50 values of 84.65 µg/mL, 86 µg/mL, and 98 µg/mL for Q, GA, and R, respectively. These compounds increased nitric oxide production and caused apoptosis and DNA damage, which led to changes in the treated cells’ ultrastructural behavior and finally to the death of L. donovani. These compounds also suppressed essential enzymes like trypanothione reductase and trypanothione synthetase, which are critical for leishmanial survival. The selected compounds have high antileishmanial potentials, and thus in-vivo testing and further screening are highly recommended.


2022 ◽  
Vol 196 ◽  
pp. 113081
Author(s):  
Wei-Wei Yu ◽  
Jin-Tao Ma ◽  
Juan He ◽  
Zheng-Hui Li ◽  
Ji-Kai Liu ◽  
...  

2015 ◽  
Vol 10 (1) ◽  
pp. 1934578X1501000 ◽  
Author(s):  
Nilubon Sornkaew ◽  
Yuan Lin ◽  
Fei Wang ◽  
Guolin Zhang ◽  
Ratchanaporn Chokchaisiri ◽  
...  

Eight new diarylheptanoids, a 1.2:1 mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-7-phenyl-(4 E,6 E)-4,6-heptadien-3-ol (1a and 1b), a racemic mixture of (3S)- and (3 R)-1-(4-hydroxyphenyl)-3-methoxy-7-phenyl-(4 E,6 E)-4,6-heptadiene (2a and 2b), a ca. 1:1 mixture of (3S)- and (3 R)-1-(4-hydroxy-3-methoxyphenyl)-3-methoxy-7-phenyl)-(4 E,6 E)-4,6-heptadiene (3a and 3b), 3-acetoxy-1-(3,4-dihydroxyphenyl)-7-phenylheptan-5-ol (4), (3 R)-1-(4,5-dihydroxyphenyl)-7-phenyl-(6 E)-6-hepten-3,2′-epoxide (5), and thirteen known diarylheptanoids, 6-12, a 3:1 mixture of 13a and 13b, and 14-17, were isolated from the rhizomes of Curcuma comosa from Sakon Nakhon, northeastern part of Thailand. The isolated compounds were evaluated for their antiinflammatory activities on the inhibition of lipopolysaccharide-induced nitric oxide production in macrophage RAW 264.7 cells and the diarylheptanoids 1a and 1b mixture and 14 exhibited potent inhibitory activity.


2008 ◽  
Vol 56 (2) ◽  
pp. 199-202 ◽  
Author(s):  
Seong Su Hong ◽  
Seon A Lee ◽  
Xiang Hua Han ◽  
Min Hee Lee ◽  
Ji Sang Hwang ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document