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.

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.

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.

Capping of silver nanoparticles by anti-inflammatory ligands: Antibacterial activity and superoxide anion generation

2019 ◽  
Vol 193 ◽  
pp. 100-108 ◽  
Author(s):  
Manuel I. Azócar ◽  
Romina Alarcón ◽  
Antonio Castillo ◽  
Jenny M. Blamey ◽  
Mariana Walter ◽  
...  
Keyword(s):  
Silver Nanoparticles ◽  
Antibacterial Activity ◽  
Superoxide Anion ◽  
Superoxide Anion Generation ◽  
Anti Inflammatory

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 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 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 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.

Feijoa sellowiana Berg Fruit Juice: Anti-Inflammatory Effect and Activity on Superoxide Anion Generation

2014 ◽  
Vol 17 (4) ◽  
pp. 455-461 ◽  
Author(s):  
Maria T. Monforte ◽  
Vincenzo Fimiani ◽  
Francesco Lanuzza ◽  
Clara Naccari ◽  
Salvatore Restuccia ◽  
...  
Keyword(s):  
Superoxide Anion ◽  
Fruit Juice ◽  
Superoxide Anion Generation ◽  
Anti Inflammatory ◽  
Inflammatory Effect

scholarly journals Chemical Constituents from the Stems of Tinospora sinensis and Their Bioactivity

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2541 ◽  
Author(s):  
Sio-Hong Lam ◽  
Po-Hsun Chen ◽  
Hsin-Yi Hung ◽  
Tsong-Long Hwang ◽  
Chih-Chao Chiang ◽  
...  
Keyword(s):  
Analytical Methods ◽  
Superoxide Anion ◽  
Cytochalasin B ◽  
Chemical Constituents ◽  
Superoxide Anion Generation ◽  
Anti Inflammatory ◽  
New Compounds

Fifty-seven compounds were purified from the stems of Tinospora sinensis, including three new compounds characterized as a lignan (1), a pyrrole alkaloid (11), and a benzenoid (17), respectively. Their structures were elucidated and established by various spectroscopic and spectrometric analytical methods. Among the isolates, fifteen compounds were examined for their anti-inflammatory potential in vitro. The results showed that several compounds displayed moderate inhibition of N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release.

Novel Heterocyclic Hybrids Based on 2-Pyrazoline: Synthesis and Assessment of Anti-Inflammatory and Analgesic Activities

2019 ◽  
Vol 16 (6) ◽  
pp. 921-930 ◽  
Author(s):  
Ahmed A.O. Abeed ◽  
Gehad A.A. Jaleel ◽  
Mohamed S.K. Youssef
Keyword(s):  
Acute Toxicity ◽  
1H Nmr ◽  
13C Nmr ◽  
High Performance ◽  
Nmr Spectra ◽  
Chemical Shifts ◽  
Coupling Constants ◽  
Inflammatory Activity ◽  
Necrosis Factor Alpha ◽  
Anti Inflammatory

Aim and Objective: A series of new 2-pyrazoline analogues were synthesized. The structures of the synthesized compounds were elucidated by the analytical and spectroscopic data. Some selected compounds were screened for the anti-inflammatory activity by using animal model of carrageenan-induced paw edema in mice. Additionally, the analgesic and acute toxicity of these compounds were evaluated and exhibited reasonable results. The anti-oxidant and anti-inflammatory effects of these compounds were established by measuring the contents of malondialdehyde (MDA), reduced glutathione (GSH), nitric oxide (NO), and tumor necrosis factor alpha (TNF-α) in the edema paw tissue. Materials and Methods: All chemicals and reagents used in current study were of analytical grade. Melting points were determined using APP. Digital ST 15 melting point apparatus and are uncorrected. FT-IR spectra were recorded on a Pye-Unicam SP3-100 spectrophotometer in KBr pellet. All 1H and 13C NMR spectra were recorded on AVANCE-III (400 MHz) High Performance FT-NMR Spectrometer Brucker (Switzerland) and some 1H NMR spectra were recorded on Varian EM-360L NMR Spectrophotometer (60 MHz) (USA) in CDCl3 or DMSO-d6 as solvent. Chemical shifts are reported in δ units and the coupling constants (J) are reported in hertz. C, H, N and S analyses were performed with a Vario EL C, H, N, S Analyzer. Carrageenan (product number C1013) was obtained from Sigma-Aldrich (USA). Results: The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analyses. The results of pharmacological activity revealed that compounds 5, 6, 7, and 15 could be recognized as potential multi-potent anti-inflammatory. Conclusion: A simple and suitable method for the synthesis of new pharmacophore was reported. We have designed nineteen heterocycles related to pyrazoline ring, and evaluated eleven of them for their antiinflammatory, analgesic and acute toxicity activities. Compounds 5, 6, 7, and 15 proved to be the interesting compounds, they have high anti-inflammatory activity. However, all the selected compounds show remarkable analgesic activity.

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