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.

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 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 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 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 Targeted Isolation of Xenicane Diterpenoids from Taiwanese Soft Coral Asterospicularia laurae

Marine Drugs ◽  
2021 ◽  
Vol 19 (3) ◽  
pp. 123
Author(s):  
Yu-Chi Lin ◽  
Yi-Jen Chen ◽  
Shu-Rong Chen ◽  
Wan-Ju Lien ◽  
Hsueh-Wei Chang ◽  
...  
Keyword(s):  
Cytotoxic Effect ◽  
Soft Coral ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Analyses ◽  
Potential Source ◽  
First Case ◽  
The Family ◽  
Mcf 7

Application of LC-MS/MS-based molecular networking indicated the ethanol extract of octocoral Asterospicularia laurae is a potential source for the discovery of new xenicane derivatives. A natural product investigation of this soft coral resulted in the isolation of four new xenicane diterpenoids, asterolaurins O‒R (1‒4), together with six known compounds, xeniolide-A (5), isoxeniolide-A (6), xeniolide-B (7), 7,8-epoxyxeniolide-B (8), 7,8-oxido-isoxeniolide-A (9), and 9-hydroxyxeniolide-F (10). The structures of isolated compounds were characterized by employing spectroscopic analyses, including 2D-NMR (COSY, HMQC, HMBC, and NOESY) and high-resolution electrospray ionization mass spectrometry (HRESIMS). Asterolaurin O is the first case of brominated tricarbocyclic type floridicin in the family Xeniidae. Concerning bioactivity, the cytotoxic activity of those isolates was evaluated. As a result, compounds 1 and 2 demonstrated a selective cytotoxic effect against the MCF-7 cell line at IC50 of 14.7 and 25.1 μM, respectively.

scholarly journals tert-Butylphenolic Derivatives from Paenibacillus odorifer—A Case of Bioconversion

Molecules ◽  
2018 ◽  
Vol 23 (8) ◽  
pp. 1951 ◽  
Author(s):  
Thi-Bach-Le Nguyen ◽  
Olivier Delalande ◽  
Isabelle Rouaud ◽  
Solenn Ferron ◽  
Laura Chaillot ◽  
...  
Keyword(s):  
Bacterial Strain ◽  
2D Nmr ◽  
One Dimensional ◽  
Spectroscopic Analyses ◽  
Human Keratinocyte ◽  
Rhizocarpon Geographicum ◽  
Ionisation Mass Spectrometry ◽  
Keratinocyte Cell ◽  
Ic50 Values ◽  
First Time

Two compounds (1) and (2) containing tert-butylphenol groups were, for the first time, produced during the culture of Paenibacillus odorifer, a bacterial strain associated with the crustose lichen, Rhizocarpon geographicum. Their entire structures were identified by one-dimensional (1D) and two-dimensional (2D) NMR and high-resolution electrospray ionisation mass spectrometry (HRESIMS) spectroscopic analyses. Among them, Compound 1 exhibited significant cytotoxicity against B16 murine melanoma and HaCaT human keratinocyte cell lines with micromolar half maximal inhibitory concentration (IC50) values. Furthermore, after supplementation studies, a putative biosynthesis pathway was proposed for Compound 1 throughout a bioconversion by this bacterial strain of butylated hydroxyanisole (BHA), an antioxidant polymer additive.

scholarly journals Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3927
Author(s):  
Jing-Shuai Wu ◽  
Xiao-Hui Shi ◽  
Ya-Hui Zhang ◽  
Chang-Lun Shao ◽  
Xiu-Mei Fu ◽  
...  
Keyword(s):  
Aspergillus Terreus ◽  
Epigenetic Modification ◽  
2D Nmr ◽  
Etoac Extract ◽  
One Dimensional ◽  
X Ray ◽  
Deacetylase Inhibitor ◽  
Ic50 Values ◽  
First Time ◽  
Mic Value

Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

scholarly journals New Metabolites from the Marine-Derived Fungus Aspergillus Fumigatus

2012 ◽  
Vol 7 (4) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Shamil Sh. Afiyatullov ◽  
Olesya I. Zhuravleva ◽  
Alexandr S. Antonov ◽  
Anatoly I. Kalinovsky ◽  
Michail V. Pivkin ◽  
...  
Keyword(s):  
Aspergillus Fumigatus ◽  
Soft Coral ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Ehrlich Carcinoma ◽  
Early Apoptosis ◽  
Marine Strain ◽  
New Metabolites

A new alkaloid, fumiquinazoline K (1), and a new nordammarane triterpenoid (2), together with three known diketopiperazines (3-5) and tryptoquivaline F (6) have been isolated from a marine strain of Aspergillus fumigatus KMM 4631 associated with the soft coral Sinularia sp. Their structures were determined by HR-MS and 1D and 2D NMR. Compounds 3-5 exhibit weak cytotoxicity against cytoplasm non-specific esterase in Ehrlich carcinoma cells. Compound 3 also induces early apoptosis of the same cells in a non-toxic range of concentrations.

Aspernolides L and M, new butyrolactones from the endophytic fungus Aspergillus versicolor

2017 ◽  
Vol 72 (5-6) ◽  
pp. 155-160 ◽  
Author(s):  
Sabrin R.M. Ibrahim ◽  
Gamal A. Mohamed ◽  
Samir A. Ross
Keyword(s):  
Endophytic Fungi ◽  
Endophytic Fungus ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Systematic Search ◽  
Aspergillus Versicolor ◽  
Active Compounds ◽  
Etoac Extract ◽  
First Time

Abstract During the systematic search of active compounds from endophytic fungi, two new butyrolactones, namely aspernolides L (2) and M (4), together with four known compounds: 1-O-acetylglycerol (1), butyrolactone I (3), butyrolactone VI (5), and (+) alantrypinone (6) were characterized from the EtOAc extract of the endophytic fungus Aspergillus versicolor isolated from the roots of Pulicaria crispa (Asteraceae). Extensive spectroscopic analysis, including 1D, 2D NMR, and HRESIMS, was used to elucidate their structures. Compounds 1, 5, and 6 are reported for the first time from this fungus.

scholarly journals A HOPANE TRITERPENOID FROM THE MYCELIUM OF Isaria japonica IN VIETNAM

2017 ◽  
Vol 55 (5) ◽  
pp. 535
Author(s):  
Nguyen Ngoc Tuan ◽  
Tran Thi Kim Anh ◽  
Ping-Chung Kuo ◽  
Tran Dinh Thang
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Methanol Extract ◽  
2D Nmr ◽  
1H And 13C Nmr ◽  
Nmr Techniques ◽  
First Time

A hopane triterpenoid (11b, 22-dihydroxyhopane) was isolated from the methanol extract of the mycelium of Isaria japonica in Vietnam. The structure of this compound was elucidated using a combination of 1D and 2D NMR techniques (1H-, 13C-NMR, COSY, HSQC and HMBC). In the study, we reported the comprehensive 1H- and 13C-NMR spectral data of 11b, 22-dihydroxyhopane for the first time.

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