scholarly journals Scalarane-Type Sesterterpenoids from the Marine Sponge Lendenfeldia sp. Alleviate Inflammation in Human Neutrophils

Marine Drugs ◽  
2021 ◽  
Vol 19 (10) ◽  
pp. 561
Author(s):  
Bo-Rong Peng ◽  
Kuei-Hung Lai ◽  
Gene-Hsiang Lee ◽  
Steve Sheng-Fa Yu ◽  
Chang-Yih Duh ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Superoxide Anion ◽  
Inflammatory Responses ◽  
Chemical Diversity ◽  
Human Neutrophils ◽  
Metabolomic Profile ◽  
Inhibitory Effects ◽  
Neutrophilic Inflammation ◽  
The Rich ◽  
First Time

Sponge-derived scalaranes are remarkable sesterterpenoids previously found to exhibit profound inhibitory effects against neutrophilic inflammation. In our current work, we constructed the metabolomic profile of marine sponge Lendenfeldia sp. for the first time using a tandem mass spectrometry (MS/MS) molecular networking approach. The results highlighted the rich chemical diversity of these scalaranes, motivating us to conduct further research to discover novel scalaranes targeting neutrophilic inflammation. MS- and NMR-assisted isolation and elucidation led to the discovery of seven new homoscalaranes, lendenfeldaranes K–Q (1–7), characterized by methylation at C-24, together with five known derivatives, lendenfeldarane B (8), 25-nor-24-methyl-12,24-dioxoscalar-16-en-22-oic acid (9), 24-methyl-12,24,25-trioxoscalar-16-en-22-oic acid (10), felixin B (11), and 23-hydroxy-20-methyldeoxoscalarin (12). Scalaranes 1–4 and 6–12 were assayed against superoxide anion generation and elastase release, which represented the neutrophilic inflammatory responses of respiratory burst and degranulation, respectively. The results indicated that 1–3 and 6–12 exhibited potential anti-inflammatory activities (IC50 for superoxide anion scavenging: 0.87~6.57 μM; IC50 for elastase release: 1.12~6.97 μM).

Four New 2-(2-Phenylethyl)-4H-chromen-4-one Derivatives from the Resinous Wood of Aquilaria sinensis and Their Inhibitory Activities on Neutrophil Pro-Inflammatory Responses

Planta Medica ◽  
2018 ◽  
Vol 84 (18) ◽  
pp. 1340-1347 ◽  
Author(s):  
Sin-Ling Wang ◽  
Hsiang-Ruei Liao ◽  
Ming-Jen Cheng ◽  
Chih-Wen Shu ◽  
Chun-Lin Chen ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Inflammatory Responses ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Aquilaria Sinensis ◽  
Superoxide Anion Generation ◽  
Spectroscopic Analyses ◽  
Inhibitory Activities ◽  
New Compounds ◽  
First Time

AbstractFour new 2-(2-phenylethyl)-4H-chromen-4-one derivatives, 6-hydroxy-5-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (1), 6,7-dimethoxy-2-[2-(2′-hydroxyphenyl)ethyl]chromone (2), 5-hydroxy-6-methoxy-2-[2-(3′-methoxyphenyl)ethyl]-chromone (3), and 7-chloro-8-hydroxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (4), have been isolated from the resinous wood of Aquilaria sinensis, together with 16 known compounds (5–20). Among these, 7-methoxy-2-[2-(4′-methoxyphenyl)ethyl]chromone (5) was isolated from a natural source for the first time. The structures of the new compounds were established by spectroscopic analyses (1D and 2D NMR, HR-ESI-MS, IR, UV). Nine compounds, including 1 showed more than 80% inhibition of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine at 50 µM.

Inhibitory effects of 16-hydroxycleroda-3,13(14)E-dien-15-oic acid on superoxide anion and elastase release in human neutrophils through multiple mechanisms

2008 ◽  
Vol 586 (1-3) ◽  
pp. 332-339 ◽  
Author(s):  
Han-Lin Chang ◽  
Fang-Rong Chang ◽  
Jin-Shan Chen ◽  
Hui-Po Wang ◽  
Yi-Hsiu Wu ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Human Neutrophils ◽  
Inhibitory Effects

scholarly journals Natural Clovanes from the Gorgonian Coral Rumphella Antipathies

2013 ◽  
Vol 8 (8) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Hsu-Ming Chung ◽  
Wei-Hsien Wang ◽  
Tsong-Long Hwang ◽  
Yang-Chang Wu ◽  
Ping-Jyun Sung
Keyword(s):  
Spectral Data ◽  
Natural Source ◽  
Human Neutrophils ◽  
Spectroscopic Methods ◽  
Superoxide Anions ◽  
Inhibitory Effects ◽  
Gorgonian Coral ◽  
First Time

Three natural clovane-related sesquiterpenoids, 2β-acetoxyclovan-9α-ol (1), 9α-acetoxyclovan-2β-ol (2) and clovan-2β,9β-diol (3), were isolated from the gorgonian coral Rumphella antipathies. The structures of clovanes 1–3 were elucidated by spectroscopic methods and by comparison of the spectral data with those of known clovane analogues. This is the first time that clovanes 1–3 have been isolated from a natural source. Clovanes 1 and 2 displayed inhibitory effects on the generation of superoxide anions and the release of elastase by human neutrophils.

scholarly journals Targeting redox regulatory site of protein kinase B impedes neutrophilic inflammation in lung injury

2018 ◽  
Author(s):  
Po-Jen Chen ◽  
I-Ling Ko ◽  
Chia-Lin Lee ◽  
Hao-Chun Hu ◽  
Fang-Rong Chang ◽  
...  
Keyword(s):  
Protein Kinase ◽  
Lung Injury ◽  
Inflammatory Responses ◽  
Protein Kinase B ◽  
Reduced Form ◽  
Human Neutrophils ◽  
Akt Inhibitor ◽  
Neutrophilic Inflammation

AbstractNeutrophil activation has a pathogenic effect in inflammatory diseases. Protein kinase B (PKB)/AKT regulates diverse cellular responses. However, the significance of AKT in neutrophilic inflammation is still not well understood. Here, we identified CLLV-1 as a novel AKT inhibitor. CLLV-1 inhibited respiratory burst, degranulation, chemotaxis, and AKT phosphorylation in activated human neutrophils and dHL-60 cells. Significantly, CLLV-1 blocked AKT activity and covalently reacted with AKT Cys310 in vitro. The AKT309-313 peptide-CLLV-1 adducts were determined by NMR or mass spectrometry assay. The alkylation agent-conjugated AKT (reduced form) level was also inhibited by CLLV-1. Additionally, CLLV-1 ameliorated lipopolysaccharide (LPS)-induced acute lung injury (ALI) in mice. CLLV-1 acts as a covalent allosteric AKT inhibitor by targeting AKT Cys310 to restrain inflammatory responses in human neutrophils and LPS-induced ALI in vivo. Our findings provide a mechanistic framework for redox modification of AKT that may serve as a novel pharmacological target to alleviate neutrophilic inflammation.

scholarly journals Cladieunicellin H, a New Hemiketal Eunicellin-Based Diterpenoid from the Octocoral Cladiella sp

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Yung-Husan Chen ◽  
Chia-Ying Tai ◽  
Tsong-Long Hwang ◽  
Ping-Jyun Sung
Keyword(s):  
Superoxide Anion ◽  
Human Neutrophils ◽  
Spectroscopic Methods ◽  
Inhibitory Effects

A new hemiketal eunicellin-based diterpenoid, cladieunicellin H (1), was isolated from an Indonesian octocoral identified as Cladiella sp. The structure of 1 was determined by spectroscopic methods. This compound was found to display moderate inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

scholarly journals Bioactive Capnosanes and Cembranes from the Soft Coral Klyxum flaccidum

Marine Drugs ◽  
2019 ◽  
Vol 17 (8) ◽  
pp. 461
Author(s):  
Tseng ◽  
Ahmed ◽  
Huang ◽  
Tsai ◽  
Tai ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Spectroscopic Data ◽  
Cytochalasin B ◽  
Soft Coral ◽  
Biological Activities ◽  
Human Neutrophils ◽  
Data Comparison ◽  
Spectroscopic Analyses ◽  
New Compounds ◽  
First Time

Two new capnosane-based diterpenoids, flaccidenol A (1) and 7-epi-pavidolide D (2), two new cembranoids, flaccidodioxide (3) and flaccidodiol (4), and three known compounds 5 to 7 were characterized from the marine soft coral Klyxum flaccidum, collected off the coast of the island of Pratas. The structures of the new compounds were determined by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and spectroscopic data comparison with related structures. The rare capnosane diterpenoids were isolated herein from the genus Klyxum for the first time. The cytotoxicity of compounds 1 to 7 against the proliferation of a limited panel of cancer cell lines was assayed. The isolated diterpenoids also exhibited anti-inflammatory activity through suppression of superoxide anion generation and elastase release in the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-stimulated human neutrophils. Furthermore, 1 and 7 also exhibited cytotoxicity toward the tested cancer cells, and 7 could effectively inhibit elastase release. It is worth noting that the biological activities of 7 are reported for the first time in this paper.

scholarly journals Isolation of Lobane and Prenyleudesmane Diterpenoids from the Soft Coral Lobophytum varium

Marine Drugs ◽  
2020 ◽  
Vol 18 (4) ◽  
pp. 223
Author(s):  
Chuan-Hsiang Chang ◽  
Atallah F. Ahmed ◽  
Tian-Sheng Yang ◽  
You-Cheng Lin ◽  
Chiung-Yao Huang ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Soft Coral ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Etoac Extract ◽  
1H And 13C Nmr ◽  
Spectroscopic Analyses ◽  
Complete Assignment ◽  
First Time ◽  
New Metabolites

Further chemical investigation of the EtOAc extract of the soft coral Lobophytum varium resulted in the discovery of eleven new diterpenoids lobovarols F–P (1–11) of lobane– and prenyleudesmane–types, along with two known metabolites (12 and 13). The structures of the new metabolites were established by spectroscopic analyses, including 2D NMR experiments. The absolute configuration of 1 was determined using Mosher’s method. The complete assignment of 1H and 13C NMR spectroscopic data of 12 and 13 and the identification of pyran-derived moieties in the prenyleudesmanes were reported for the first time. Anti-inflammatory activities of the isolated compounds in suppressing elastase release and superoxide anion generation in human neutrophils were disclosed for 1, 2, 4, 12, and 13. A stereospecific biosynthesis for lobanes and prenyleudesmanes from the related prenylgermacranes could explain the coexistence of lobanes and prenylgermacranes in L. varium.

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