Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

Four phenylfuropyridone racemates, (±)-tersones A-C and E (1–3, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs 8 and 9 were isolated from the deep-sea fungus Phomopsis tersa. Their structures and absolute configurations were characterized on the basis of comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Moreover, compounds 1–9 were evaluated for in vitro antimicrobial and cytotoxic activity. Compounds 5b and 8b exhibited antibacterial activity against S. aureus with the MIC value of 31.5 μg/mL, while compound 5b showed cytoxic activities against SF-268, MCF-7, HepG-2 and A549 cell lines with IC50 values of 32.0, 29.5, 39.5 and 33.2 μM, respectively.

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Chevalones H–M: Six New α-Pyrone Meroterpenoids from the Gorgonian Coral-Derived Fungus Aspergillus hiratsukae SCSIO 7S2001

Marine Drugs ◽

10.3390/md20010071 ◽

2022 ◽

Vol 20 (1) ◽

pp. 71

Author(s):

Xia-Yu Chen ◽

Qi Zeng ◽

Yu-Chan Chen ◽

Wei-Mao Zhong ◽

Yao Xiang ◽

...

Keyword(s):

Antibacterial Activity ◽

South China Sea ◽

South China ◽

A549 Cell ◽

Spectroscopic Analysis ◽

X Ray Diffraction ◽

Gorgonian Coral ◽

X Ray ◽

Ic50 Values ◽

Mcf 7

Six new α-pyrone meroterpenoid chevalones H–M (1–6), together with six known compounds (7–12), were isolated from the gorgonian coral-derived fungus Aspergillus hiratsukae SCSIO 7S2001 collected from Mischief Reef in the South China Sea. Their structures, including absolute configurations, were elucidated on the basis of spectroscopic analysis and X-ray diffraction data. Compounds 1–5 and 7 showed different degrees of antibacterial activity with MIC values of 6.25–100 μg/mL. Compound 8 exhibited potent cytotoxicity against SF-268, MCF-7, and A549 cell lines with IC50 values of 12.75, 9.29, and 20.11 μM, respectively.

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Structurally Diverse Polycyclic Salicylaldehyde Derivative Enantiomers from a Marine-Derived Fungus Eurotium sp. SCSIO F452

Marine Drugs ◽

10.3390/md19100543 ◽

2021 ◽

Vol 19 (10) ◽

pp. 543

Author(s):

Wei-Mao Zhong ◽

Xiao-Yi Wei ◽

Yu-Chan Chen ◽

Qi Zeng ◽

Jun-Feng Wang ◽

...

Keyword(s):

A549 Cell ◽

13C Nmr ◽

Large Scale ◽

Chemical Constituents ◽

Chemical Diversity ◽

Cytotoxic Activities ◽

X Ray Diffraction ◽

X Ray ◽

Spectroscopic Analyses ◽

Mcf 7

To enlarge the chemical diversity of Eurotium sp. SCSIO F452, a talented marine-derived fungus, we further investigated its chemical constituents from a large-scale fermentation with modified culture. Four pairs of new salicylaldehyde derivative enantiomers, euroticins F-I (1–4), as well as a known one eurotirumin (5) were isolated and characterized. Compound 1 features an unprecedented constructed 6/6/6/5 tetracyclic structures, while 2 and 3 represent two new types of 6/6/5 scaffolds. Their structures were established by comprehensive spectroscopic analyses, X-ray diffraction, 13C NMR, and electronic circular dichroism calculations. Selected compounds showed significant inhibitory activity against α-glucosidase and moderate cytotoxic activities against SF-268, MCF-7, HepG2, and A549 cell lines.

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Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508

Marine Drugs ◽

10.3390/md16090329 ◽

2018 ◽

Vol 16 (9) ◽

pp. 329 ◽

Cited By ~ 9

Author(s):

Jian-Lin Xu ◽

Hong-Xin Liu ◽

Yu-Chan Chen ◽

Hai-Bo Tan ◽

Heng Guo ◽

...

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

A549 Cell ◽

Marine Sediment ◽

Deep Sea ◽

Crystallographic Analysis ◽

X Ray ◽

Naturally Occurring ◽

Ic50 Values ◽

New Compounds

Five new benzophenone derivatives named tenellones D–H (1–5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), were isolated from the deep marine sediment-derived fungus Phomopsis lithocarpus FS508. All of the structures for these new compounds were fully characterized and established on the basis of extensive spectroscopic interpretation and X-ray crystallographic analysis. Compound 5 exhibited cytotoxic activity against HepG-2 and A549 cell lines with IC50 values of 16.0 and 17.6 μM, respectively.

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Nitric Oxide Inhibitory Activity of Xanthones from the Green Fruits of Cratoxylum formosum ssp. pruniflorum

Australian Journal of Chemistry ◽

10.1071/ch10193 ◽

2010 ◽

Vol 63 (11) ◽

pp. 1550 ◽

Cited By ~ 15

Author(s):

Nawong Boonnak ◽

Achjana Khamthip ◽

Chatchanok Karalai ◽

Suchada Chantrapromma ◽

Chanita Ponglimanont ◽

...

Keyword(s):

Nitric Oxide ◽

Antibacterial Activity ◽

Inhibitory Activity ◽

Spectroscopic Methods ◽

Gram Negative Bacteria ◽

Gram Negative ◽

X Ray ◽

X Ray Crystallography ◽

Ic50 Values ◽

Mic Value

Three new xanthones, pruniflorone M-O (1–3), and a new xanthonolignoid, 3-methoxy-5′-demethoxycadensin G (4), were isolated from the green fruits of Cratoxylum formosum ssp. pruniflorum along with three known xanthones (5–7) and a known flavonoid (8). Their structures were elucidated by spectroscopic methods and the structure of 1 was also determined by X-ray crystallography. Compounds 2 and 7 showed potent nitric oxide inhibitory activity with IC50 values of 4.4 and 4.3 μM, respectively. Moreover, 7 also showed strong antibacterial activity against both Gram-positive and Gram-negative bacteria with an MIC value of 4.67 μg mL–1.

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Curcumin-Loaded Mixed Micelles: Preparation, Characterization, and In Vitro Antitumor Activity

Journal of Nanotechnology ◽

10.1155/2018/9103120 ◽

2018 ◽

Vol 2018 ◽

pp. 1-9 ◽

Cited By ~ 6

Author(s):

Suping Ji ◽

Xiao Lin ◽

Enjiang Yu ◽

Chengyang Dian ◽

Xiong Yan ◽

...

Keyword(s):

Mixed Micelles ◽

Drug Loading ◽

Molecular State ◽

X Ray Diffraction ◽

X Ray ◽

Release Property ◽

Mean Size ◽

Xrd Patterns ◽

Mcf 7

The objective of this study was to prepare curcumin-loaded mixed Soluplus/TPGS micelles (Cur-TPGS-PMs) for oral administration. The Cur-TPGS-PMs showed a mean size of 65.54 ± 2.57 nm, drug encapsulation efficiency over 85%, and drug loading of 8.17%. The Cur-TPGS-PMs were found to be stable in various pH media (pH 1.2 for 2 h, pH 6.8 for 2 h, and pH 7.4 for 6 h). The X-ray diffraction (XRD) patterns illustrated that curcumin was in the amorphous or molecular state within PMs. The In vitro release test indicated that Cur-TPGS-PMs possessed a significant sustained-release property. The cell viability in MCF-7 cells was found to be relatively lower in Cur-TPGS-PM-treated cells as compared to free Cur-treated cells. CLSM imaging revealed that mixed micelles were efficiently absorbed into the cytoplasm region of MCF-7 cells. Therefore, Cur-TPGS-PMs could have the significant value for the chronic breast cancer therapy.

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Thioester-Containing Benzoate Derivatives with α-Glucosidase Inhibitory Activity from the Deep-Sea-Derived Fungus Talaromyces indigoticus FS688

Marine Drugs ◽

10.3390/md20010033 ◽

2021 ◽

Vol 20 (1) ◽

pp. 33

Author(s):

Mingqiong Li ◽

Saini Li ◽

Jinhua Hu ◽

Xiaoxia Gao ◽

Yanlin Wang ◽

...

Keyword(s):

Inhibitory Activity ◽

Deep Sea ◽

Spectroscopic Analysis ◽

X Ray Diffraction ◽

Docking Analysis ◽

X Ray ◽

Structure Activity ◽

Ic50 Value ◽

Ic50 Values ◽

Benzoate Derivatives

Eurothiocins C–H (1–6), six unusual thioester-containing benzoate derivatives, were isolated from the deep-sea-derived fungus Talaromyces indigoticus FS688 together with a known analogue eurothiocin A (7). Their structures were elucidated through spectroscopic analysis and the absolute configurations were determined by X-ray diffraction and ECD calculations. In addition, compound 1 exhibited significant inhibitory activity against α-glucosidase with an IC50 value of 5.4 μM, while compounds 4 and 5 showed moderate effects with IC50 values of 33.6 and 72.1 μM, respectively. A preliminary structure–activity relationship is discussed and a docking analysis was performed.

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Two New Cytotoxic Steroidal Alkaloids from Sarcococca Hookeriana

Molecules ◽

10.3390/molecules24010011 ◽

2018 ◽

Vol 24 (1) ◽

pp. 11 ◽

Cited By ~ 1

Author(s):

Shaojie Huo ◽

Jichun Wu ◽

Xicheng He ◽

Lutai Pan ◽

Jiang Du

Keyword(s):

Cell Lines ◽

Human Cancer ◽

Cytotoxic Activities ◽

Steroidal Alkaloids ◽

X Ray ◽

Human Cancer Cell Lines ◽

X Ray Crystallography ◽

Ic50 Values ◽

Mcf 7

Two new steroidal alkaloids, named hookerianine A (1) and hookerianine B (2) were isolated from the stems and roots of Sarcococca hookeriana Baill., along with two known compounds, sarcorucinine G (3) and epipachysamine D (4). On the basis of spectroscopic methods and by comparison with literature data, their structures were determined. As well as X-ray crystallography was performed to confirm compound 4. To identify novel antitumor inhibitors, all compounds were performed a CCK-8 assay against five human cancer cell lines SW480, SMMC-7721, PC3, MCF-7 and K562 in vitro. Compound 2 exhibited moderate cytotoxic activities to all cell lines with IC50 values in the range of 5.97–19.44 μM. Compound 3 was the most effective one against SW480 and K562 cell lines with IC50 values of 5.77 and 6.29 μM, respectively.

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Reactions of 2-cyano-3-ferrocenylacrylonitrile with malononitrile: formation of 4-ferrocenylpyridine-3,5-dicarbonitrile derivatives and sodium polymeric complexes containing carbanionic ligands

Pure and Applied Chemistry ◽

10.1515/pac-2014-0611 ◽

2014 ◽

Vol 86 (11) ◽

pp. 1839-1852 ◽

Cited By ~ 1

Author(s):

Elena Ivanovna Klimova ◽

Marcos Martínez García ◽

Jessica Jazmin Sánchez García ◽

Teresa Ramírez Apan ◽

Andrei V. Churakov ◽

...

Keyword(s):

Human Tumor ◽

Tumor Cell Lines ◽

X Ray Diffraction ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

X Ray ◽

Biological Specificity ◽

Polymeric Complexes ◽

Mcf 7

Abstract The reactions of 2-cyano-3-ferrocenylacrylonitrile with malononitrile in a EtOH/H2O or MeOH/H2O medium in the presence of Na2CO3 afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles 3a,b (multi-component condensation), 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenylmethyl-3,4-dihydropyridine-3,5-dicarbonitriles 4a,b (multi-component cyclodimerization) and Na+ polymeric complexes: {[Na+(2-ferrocenyl(tetracyano)propenyl)–L]∞5a,b and [Na+(2-amino-3,5-dicyano-4-ferrocenyl-6-pyridyl-dicyanomethyl)–L]∞6a,b, where L = ethanol, methanol. Complexes with L = acetonitrile, dimethylformamide, acetone, ethyl acetate were prepared by recrystallization. The structures of the compounds 3b, 4b and Na+ polymeric complexes were established by the spectroscopic data and X-ray diffraction analysis. Two compounds 3a and 4a were tested in vitro against six human tumor cell lines U-251, PC-3, K-562, HCT-15, MCF-7 and SKLU-1 to assess their in vitro antitumor activity. The results suggest biological specificity towards PC-3, K-562 and HCT-15 cells for compound 3a, and towards PC-3 cell for compound 4a at doses of 50 μM, which are lower than cis-platin.

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Studies of Cell Growth on TiO2 Nanotubes

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.620.325 ◽

2012 ◽

Vol 620 ◽

pp. 325-329 ◽

Cited By ~ 1

Author(s):

Nur Hidayati Ahmad Barudin ◽

Srimala Sreekantan ◽

Ong Ming Thong ◽

Lam Kit Lay

Keyword(s):

Cancer Cell Line ◽

Cellular Responses ◽

Cell Interaction ◽

Electrochemical Anodization ◽

X Ray Diffraction ◽

Cell Adherence ◽

Anodization Voltage ◽

X Ray ◽

Mcf 7

The in vitro cell response was investigated on flat Ti surface vs nanostructured TiO2 nanotube surface. The titanium dioxide nanotube layers were prepared by electrochemical anodization of Ti in ethylene glycol, 5 wt% NH4F and 1ml H2O2. The nanotube layered structure and morphology were characterized using X-ray diffraction (XRD) and field emission scanning electron microscopy (FESEM). The diameter and the length of the nanotubes are found to increase with anodization voltage. Hs27 and breast cancer cell line MCF-7 were used for cell interaction studies. Different surfaces of titanium show variation in term of growth and viability of cells. Different cell type also show different cellular responses to these surfaces. Titanium nanotube with tube diameter 90 nm promoted normal cell adherence and spreading but killed the cancer cells. The detail of the observation is discussed thoroughly in this paper.

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Briarenones A‒C, New Briarellin Diterpenoids from the Gorgonian Briareum violaceum

Marine Drugs ◽

10.3390/md17020120 ◽

2019 ◽

Vol 17 (2) ◽

pp. 120 ◽

Cited By ~ 1

Author(s):

Yang Cheng ◽

Atallah Ahmed ◽

Raha Orfali ◽

Chang-Feng Dai ◽

Jyh-Horng Sheu

Keyword(s):

Cytochalasin B ◽

2D Nmr ◽

Human Neutrophils ◽

Superoxide Anions ◽

X Ray Diffraction ◽

X Ray ◽

Chemical Structures ◽

Spectroscopic Analyses ◽

Phenyl Alanine

Three new eunicellin-derived diterpenoids of briarellin type, briarenones A‒C (1‒3), were isolated from a Formosan gorgonian Briareum violaceum. The chemical structures of the compounds were elucidated on the basis of extensive spectroscopic analyses, including two-dimensional (2D) NMR. The absolute configuration of 1 was further confirmed by a single crystal X-ray diffraction analysis. The in vitro cytotoxic and anti-inflammatory potentialities of the isolated metabolites were tested against the growth of a limited panel of cancer cell lines and against the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenyl-alanine and cytochalasin B (fMLF/CB)-stimulated human neutrophils, respectively.

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