Anti-Inflammatory Cembranoids from a Formosa Soft Coral Sarcophyton cherbonnieri

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.

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

Molecules ◽

10.3390/molecules25184149 ◽

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.

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Chemical Constituents of the Leaves of Peltophorum pterocarpum and Their Bioactivity

Molecules ◽

10.3390/molecules24020240 ◽

2019 ◽

Vol 24 (2) ◽

pp. 240 ◽

Cited By ~ 5

Author(s):

Yue-Chiun Li ◽

Ping-Chung Kuo ◽

Mei-Lin Yang ◽

Tzu-Yu Chen ◽

Tsong-Long Hwang ◽

...

Keyword(s):

Superoxide Anion ◽

Methanol Extract ◽

Chemical Constituents ◽

Mass Spectrometric ◽

Inhibitory Effects ◽

Superoxide Anion Generation ◽

Chemical Structures

Two new sesquiterpenoids peltopterins A and B (compounds 1 and 2) and fifty-two known compounds were isolated from the methanol extract of P. pterocarpum and their chemical structures were established through spectroscopic and mass spectrometric analyses. The isolates 40, 43, 44, 47, 48, 51 and 52 exhibited potential inhibitory effects of superoxide anion generation or elastase release.

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

Molecules ◽

10.3390/molecules26237311 ◽

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.

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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 ◽

10.1055/a-0645-1437 ◽

2018 ◽

Vol 84 (18) ◽

pp. 1340-1347 ◽

Cited By ~ 6

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.

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Cherbonolides M and N from a Formosan Soft Coral Sarcophyton cherbonnieri

Marine Drugs ◽

10.3390/md19050260 ◽

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.

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Chemical Constituents from the Stems of Tinospora sinensis and Their Bioactivity

Molecules ◽

10.3390/molecules23102541 ◽

2018 ◽

Vol 23 (10) ◽

pp. 2541 ◽

Cited By ~ 8

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.

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

Marine Drugs ◽

10.3390/md18040223 ◽

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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Cembranoid-Related Metabolites and Biological Activities from the Soft Coral Sinularia flexibilis

Marine Drugs ◽

10.3390/md16080278 ◽

2018 ◽

Vol 16 (8) ◽

pp. 278 ◽

Cited By ~ 8

Author(s):

Chia-Hua Wu ◽

Chih-Hua Chao ◽

Tzu-Zin Huang ◽

Chiung-Yao Huang ◽

Tsong-Long Hwang ◽

...

Keyword(s):

Spectral Analysis ◽

Cell Lines ◽

Cancer Cell ◽

Superoxide Anion ◽

Cytochalasin B ◽

Soft Coral ◽

Biological Activities ◽

Human Neutrophils ◽

Sinularia Flexibilis ◽

Anti Inflammatory

Five new cembranoid-related diterpenoids, namely, flexibilisins D and E (1 and 2), secoflexibilisolides A and B (3 and 4), and flexibilisolide H (5), along with nine known compounds (6–14), were isolated from the soft coral Sinularia flexibilis. Their structures were established by extensive spectral analysis. Compound 3 possesses an unusual skeleton that could be biogenetically derived from cembranoids. The cytotoxicity and anti-inflammatory activities of the isolates were investigated, and the results showed that dehydrosinulariolide (7) and 11-epi-sinulariolide acetate (8) exhibited cytotoxicity toward a limited panel of cancer cell lines and 14-deoxycrassin (9) displayed anti-inflammatory activity by inhibition of superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced human neutrophils.

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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 ◽

10.3390/md19010038 ◽

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.

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