scholarly journals Phytochemical Investigation and Anti-Inflammatory Activity of the Leaves of Machilus japonica var. kusanoi

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4149
Author(s):  
Shiou-Ling Li ◽  
Ho-Cheng Wu ◽  
Tsong-Long Hwang ◽  
Chu-Hung Lin ◽  
Shuen-Shin Yang ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Superoxide Anion Generation ◽  
Phytochemical Investigation ◽  
Potent Inhibition ◽  
Bioassay Guided Fractionation ◽  
Ic50 Values ◽  
Anti Inflammatory ◽  
New Compounds

In a series of anti-inflammatory screenings of lauraceous plants, the methanolic extract of the leaves of Machilus japonica var. kusanoi (Hayata) J.C. Liao showed potent inhibition on both superoxide anion generation and elastase release in human neutrophils. Bioassay-guided fractionation of the leaves of M. japonica var. kusanoi led to the isolation of twenty compounds, including six new butanolides, machinolides A–F (1–6), and fourteen known compounds (7–20). Their structures were characterized by 1D and 2D NMR, UV, IR, CD, and MS data. The absolute configuration of the new compounds were unambiguously confirmed by single-crystal X-ray diffraction analyses (1, 2, and 3) and Mosher’s method (4, 5, and 6). In addition, lignans, (+)-eudesmin (11), (+)-methylpiperitol (12), (+)-pinoresinol (13), and (+)-galbelgin (16) exhibited inhibitory effects on N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation in human neutrophils with IC50 values of 8.71 ± 0.74 μM, 2.23 ± 0.92 μM, 6.81 ± 1.07 μM, and 7.15 ± 2.26 μM, respectively. The results revealed the anti-inflammatory potentials of Formosan Machilus japonica var. kusanoi.

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.

scholarly journals Anti-Inflammatory Cembranoids from a Formosa Soft Coral Sarcophyton cherbonnieri

Marine Drugs ◽  
2020 ◽  
Vol 18 (11) ◽  
pp. 573
Author(s):  
Chia-Chi Peng ◽  
Chiung-Yao Huang ◽  
Atallah F. Ahmed ◽  
Tsong-Long Hwang ◽  
Jyh-Horng Sheu
Keyword(s):  
Superoxide Anion ◽  
Soft Coral ◽  
Chemical Reduction ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Superoxide Anion Generation ◽  
Chemical Structures ◽  
Proinflammatory Responses ◽  
Anti Inflammatory

The present investigation on chemical constituents of the soft coral Sarcophyton cherbonnieri resulted in the isolation of seven new cembranoids, cherbonolides F–L (1–7). The chemical structures of 1–7 were determined by spectroscopic methods, including infrared, one- and two-dimensional (1D and 2D) NMR (COSY, HSQC, HMBC, and NOESY), MS experiments, and a chemical reduction of hydroperoxide by triphenylphosphine. The anti-inflammatory activities of 1–7 against neutrophil proinflammatory responses were evaluated by measuring their inhibitory ability toward N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced superoxide anion generation and elastase release in primary human neutrophils. The results showed that all isolates exhibited moderate activities, while cherbonolide G (2) and cherbonolide H (3) displayed a more active effect than others on the inhibition of elastase release (48.2% ± 6.2%) and superoxide anion generation (44.5% ± 4.6%) at 30 µM, respectively.

scholarly journals An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge Spongia sp. from the Red Sea

Marine Drugs ◽  
2021 ◽  
Vol 19 (1) ◽  
pp. 38
Author(s):  
Chi-Jen Tai ◽  
Chiung-Yao Huang ◽  
Atallah F. Ahmed ◽  
Raha S. Orfali ◽  
Walied M. Alarif ◽  
...  
Keyword(s):  
Red Sea ◽  
Superoxide Anion ◽  
Dermal Fibroblast ◽  
Fibroblast Cell ◽  
Inhibitory Effect ◽  
Human Dermal Fibroblast ◽  
Superoxide Anion Generation ◽  
Potent Inhibitory Effect ◽  
Anti Inflammatory ◽  
New Compounds

Chemical investigation of a Red Sea Spongia sp. led to the isolation of four new compounds, i.e., 17-dehydroxysponalactone (1), a carboxylic acid, spongiafuranic acid A (2), one hydroxamic acid, spongiafuranohydroxamic acid A (3), and a furanyl trinorsesterpenoid 16-epi-irciformonin G (4), along with three known metabolites (−)-sponalisolide B (5), 18-nor- 3,17-dihydroxy-spongia-3,13(16),14-trien-2-one (6), and cholesta-7-ene-3β,5α-diol-6-one (7). The biosynthetic pathway for the molecular skeleton of 1 and related compounds was postulated for the first time. Anti-inflammatory activity of these metabolites to inhibit superoxide anion generation and elastase release in N-formyl-methionyl-leucyl phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophil cells and cytotoxicity of these compounds toward three cancer cell lines and one human dermal fibroblast cell line were assayed. Compound 1 was found to significantly reduce the superoxide anion generation and elastase release at a concentration of 10 μM, and compound 5 was also found to display strong inhibitory activity against superoxide anion generation at the same concentration. Due to the noncytotoxic activity and the potent inhibitory effect toward the superoxide anion generation and elastase release, 1 and 5 can be considered to be promising anti-inflammatory agents.

scholarly journals Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽  
2019 ◽  
Vol 24 (18) ◽  
pp. 3336 ◽  
Author(s):  
Ping-Chen Tu ◽  
Han-Chun Tseng ◽  
Yu-Chia Liang ◽  
Guan-Jhong Huang ◽  
Te-Ling Lu ◽  
...  
Keyword(s):  
2D Nmr ◽  
Raw 264.7 Cells ◽  
No Production ◽  
Isolation And Characterization ◽  
Whole Plant ◽  
Phytochemical Investigation ◽  
Ic50 Value ◽  
Anti Inflammatory ◽  
New Compounds ◽  
First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

scholarly journals New Anti-Inflammatory Aporphine and Lignan Derivatives from the Root Wood of Hernandia nymphaeifolia

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2286 ◽  
Author(s):  
Chuan-Yen Wei ◽  
Shih-Wei Wang ◽  
Jin-Wang Ye ◽  
Tsong-Long Hwang ◽  
Ming-Jen Cheng ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Superoxide Anion ◽  
Cytochalasin B ◽  
Human Neutrophils ◽  
Superoxide Anion Production ◽  
Natural Sources ◽  
Spectroscopic Analyses ◽  
Anion Production ◽  
Ic50 Values ◽  
Anti Inflammatory

A new aporphine, 3-hydroxyhernandonine (1) and a new lignin, 4′-O-demethyl-7-O-methyldehydropodophyllotoxin (2), have been isolated from the root wood of Hernanadia nymphaeifolia, together with thirteen known compounds (3–15). The structures of these compounds were determined through mass spectrometry (MS) and spectroscopic analyses. The known isolate, 2-O-methyl-7-oxolaetine (3), was first isolated from natural sources. Among the isolated compounds, 3-hydroxyhernandonine (1), 4′-O-demethyl-7-O-methyldehydropodophyllotoxin (2), hernandonine (4), oxohernangerine (5), and oxohernagine (6) displayed inhibition (IC50 values ≤5.72 μg/mL) of superoxide anion production by human neutrophils in response to formyl-l-methionyl-l-leucyl-l-phenylalanine/cytochalasin B (fMLP/CB). In addition, 3-hydroxyhernandonine (1), 4′-O-demethyl-7-O-methyldehydropodophyllotoxin (2), oxohernangerine (5), and oxohernagine (6) suppressed fMLP/CB-induced elastase release with IC50 values ≤5.40 μg/mL.

scholarly journals Secondary Metabolites with Anti-Inflammatory Activities from One Actinobacteria Amycolatopsis taiwanensis

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5765
Author(s):  
Yung-Shun Su ◽  
Ming-Der Wu ◽  
Jih-Jung Chen ◽  
Ming-Jen Cheng ◽  
Yueh-Hsiung Kuo ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
No Production ◽  
The North ◽  
Phytochemical Investigation ◽  
Ic50 Value ◽  
Production Activity ◽  
Inos Inhibitor ◽  
Ic50 Values ◽  
New Compounds

Phytochemical investigation and chromatographic separation of extracts from one new actinobacteria strain Amycolatopsis taiwanensis that was isolated from soil of Yilan township, in the north of Taiwan, led to the isolation of nine new compounds, amycolataiwanensins A–I (1–9, resp.), and one new natural product, namely amycolataiwanensin J (10). 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. Of the isolates, 3, 5, 7 and 8 exhibited potent anti-NO production activity, with IC50 values of 17.52, 12.31, 17.81 and 13.32 μM, respectively, compared to that of quercetin, an iNOS inhibitor with an IC50 value of 35.94 μM. This is the first report on indole metabolite from the genus Amycolatopsis.

scholarly journals Constituents from the Fruiting Bodies of Trametes cubensis and Trametes suaveolens in Vietnam and Their Anti-Inflammatory Bioactivity

Molecules ◽  
2021 ◽  
Vol 26 (23) ◽  
pp. 7311
Author(s):  
Yue-Chiun Li ◽  
Nguyen Thi Ngan ◽  
Kun-Ching Cheng ◽  
Tsong-Long Hwang ◽  
Tran Dinh Thang ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Analytical Data ◽  
Significant Inhibition ◽  
Human Neutrophils ◽  
Spectrometric Analysis ◽  
Fruiting Bodies ◽  
Edible Fungi ◽  
Superoxide Anion Generation ◽  
Isolation And Characterization ◽  
Anti Inflammatory

It is reported that various fungi have been used for medicine and edible foods. The tropical Trametes genus is popular and well-known in Vietnam for its health effects and bioactivities. In this study, the fruiting bodies of the edible fungi T. cubensis and T. suaveolens were collected in Vietnam. The preliminary bioactivity screening data indicated that the methanol extracts of the fruiting bodies of T. cubensis and T. suaveolens displayed significant inhibition of superoxide anion generation and elastase release in human neutrophils. Therefore, the isolation and characterization were performed on these two species by a combination of chromatographic methods and spectrometric analysis. In total, twenty-four compounds were identified, and among these (1–3) were characterized by 1D-, 2D-NMR, and HRMS analytical data. In addition, the anti-inflammatory potentials of some purified compounds were examined by the cellular model for the inhibition of superoxide anion generation and elastase release in human neutrophils. Among the isolated compounds, (5,14), and (19) displayed significant anti-inflammatory potential. As the results suggest, the extracts and isolated compounds from T. cubensis and T. suaveolens are potential candidates for the further development of new anti-inflammatory lead drugs or natural healthy foods.

scholarly journals Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri

Marine Drugs ◽  
2021 ◽  
Vol 19 (5) ◽  
pp. 260
Author(s):  
Chia-Chi Peng ◽  
Tzu-Yin Huang ◽  
Chiung-Yao Huang ◽  
Tsong-Long Hwang ◽  
Jyh-Horng Sheu
Keyword(s):  
Superoxide Anion ◽  
Cytochalasin B ◽  
Soft Coral ◽  
2D Nmr ◽  
Human Neutrophils ◽  
Cd Spectra ◽  
Ether Linkage ◽  
Relative Configuration ◽  
Nmr Data ◽  
New Compounds

Two new isosarcophine derivatives, cherbonolides M (1) and N (2), were further isolated from a Formosan soft coral Sarcophyton cherbonnieri. The planar structure and relative configuration of both compounds were established by the detailed analysis of the IR, MS, and 1D and 2D NMR data. Further, the absolute configuration of both compounds was determined by the comparison of CD spectra with that of isosarcophine (3). Notably, cherbonolide N (2) possesses the unique cembranoidal scaffold of tetrahydrooxepane with the 12,17-ether linkage fusing with a γ-lactone. In addition, the assay for cytotoxicity of both new compounds revealed that they showed to be noncytotoxic toward the proliferation of A549, DLD-1, and HuCCT-1 cell lines. Moreover, the anti-inflammatory activities of both metabolites were carried out by measuring the N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced generation of superoxide anion and elastase release in the primary human neutrophils. Cherbonolide N (2) was found to reduce the generation of superoxide anion (20.6 ± 6.8%) and the elastase release (30.1 ± 3.3%) in the fMLF/CB-induced human neutrophils at a concentration of 30 μM.

scholarly journals Clerodane Diterpenoids from Callicarpa hypoleucophylla and Their Anti-Inflammatory Activity

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2288 ◽  
Author(s):  
Yu-Chi Lin ◽  
Jue-Jun Lin ◽  
Shu-Rong Chen ◽  
Tsong-Long Hwang ◽  
Shu-Yen Fang ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Superoxide Anion ◽  
Spectroscopic Data ◽  
Structural Diversity ◽  
Inflammatory Activity ◽  
Endemic Plant ◽  
Superoxide Anion Generation ◽  
Phytochemical Investigation ◽  
Clerodane Diterpenoids ◽  
Anti Inflammatory

Plants of the genus Callicarpa are known to possess several medicinal effects. The constituents of the Taiwan endemic plant Callicarpa hypoleucophylla have never been studied. Therefore, C. hypoleucophylla was selected for our phytochemical investigation. Two new clerodane-type diterpenoids, named callihypolins A (1) and B (2), along with seven known compounds were isolated from the leaves and twigs of the Lamiaceae plant C. hypoleucophylla and then characterized. The structures of compounds 1 and 2 were elucidated by spectroscopic data analysis, specifically, two-dimension nuclear magnetic resonance (NMR). The anti-inflammatory activity of compounds 1–9 based on the suppression of superoxide anion generation and elastase release was evaluated. Among the isolates, compounds 2–4 showed anti-inflammatory activity (9.52−32.48% inhibition at the concentration 10 μm) by suppressing superoxide anion generation and elastase release. Our findings not only expand the description of the structural diversity of the compounds present in plants of the genus Callicarpa but also highlight the possibility of developing anti-inflammatory agents from Callicarpa endemic species.

scholarly journals 1H NMR-Based Isolation of Anti-Inflammatory 9,11-Secosteroids from the Octocoral Sinularia leptoclados

Marine Drugs ◽  
2020 ◽  
Vol 18 (5) ◽  
pp. 271 ◽  
Author(s):  
Yu-Chia Chang ◽  
Kuei-Hung Lai ◽  
Sunil Kumar ◽  
Po-Jen Chen ◽  
Yi-Hsuan Wu ◽  
...  
Keyword(s):  
1H Nmr ◽  
Superoxide Anion ◽  
Nmr Spectra ◽  
Spectroscopic Analysis ◽  
Pronounced Effect ◽  
Neutrophilic Inflammation ◽  
Superoxide Anion Generation ◽  
Ic50 Values ◽  
Anti Inflammatory

Octocoral Sinularia leptoclados has been identified as a source of bioactive 9,11-secosteroids. This study adopted a targeted isolation approach to the discovery and analysis of five 9,11-secosteroids, including two novel compounds named sinleptosterols A (1) and B (2) as well as five known analogues (8αH-3β,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (3), 8βH-3β,11-dihydroxy-24-methylene-9,11-secocholest-5-en-9-one (4), leptosterol A (5), (24S)-3β,11-dihydroxy-24-methyl-9,11-secocholest-5-en-9-one (6), and 3β,11-dihydroxy-9,11-secogorgost-5-en-9-one (7)) in terms of 1H-NMR patterns and potency against neutrophilic inflammation. The structure of secosteroids 1 and 2 was deduced from general spectroscopic analysis and an examination of NMR spectra. Among the above-mentioned isolates, compound 4 had the most pronounced effect in inhibiting elastase release and superoxide anion generation, with the IC50 values of 2.96 and 1.63 μM, respectively.

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