Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5−22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher’s method. Compounds 2, 3, 5, 7, 9–18, and 20–22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

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Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽

10.3390/md19060305 ◽

2021 ◽

Vol 19 (6) ◽

pp. 305

Author(s):

Guangyuan Luo ◽

Li Zheng ◽

Qilin Wu ◽

Senhua Chen ◽

Jing Li ◽

...

Keyword(s):

Fusarium Solani ◽

2D Nmr ◽

Inflammatory Activity ◽

Raw264.7 Cells ◽

Spectroscopic Methods ◽

X Ray ◽

X Ray Crystallography ◽

Structure Activity ◽

Ic50 Values ◽

New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Marine Drugs ◽

10.3390/md20010051 ◽

2022 ◽

Vol 20 (1) ◽

pp. 51

Author(s):

Senhua Chen ◽

Heng Guo ◽

Minghua Jiang ◽

Qilin Wu ◽

Jing Li ◽

...

Keyword(s):

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Crystallographic Analysis ◽

Selective Cytotoxicity ◽

X Ray ◽

Planar Structures ◽

Spectroscopic Analyses ◽

Ic50 Values ◽

Anti Inflammatory ◽

Resolution Mass

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

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New polysubstituted monoterpenic thiazolidinones: synthesis, spectroscopic and crystal structure studies

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229618015802 ◽

2018 ◽

Vol 74 (12) ◽

pp. 1629-1634 ◽

Cited By ~ 1

Author(s):

Abdellah N'ait Ousidi ◽

Moulay Youssef Ait Itto ◽

Aziz Auhmani ◽

Abdelkhalek Riahi ◽

Anthony Robert ◽

...

Keyword(s):

Crystal Structure ◽

Nmr Spectroscopy ◽

2D Nmr ◽

Asymmetric Unit ◽

2D Nmr Spectroscopy ◽

X Ray ◽

X Ray Crystallography ◽

Naturally Occurring ◽

Spectroscopic Analyses ◽

Graph Set

The synthesis of three new polysubstituted monoterpenic thiazolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C14H21N3OS (2), (2Z,5Z)-5-[(dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C16H24N4OS (3), and (2Z,5Z)-5-[(dimethylamino)methylidene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C17H26N4OS (4), is reported, starting from the corresponding thiosemicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thiazolidin-4-ones have been fully characterized by HRMS and 1H and 13C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical molecules within the asymmetric unit with the same absolute configuration. These two molecules are linked through N—H...O hydrogen bonds, building an R 2 2(8) graph-set motif.

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Phenylhydrazone and Quinazoline Derivatives from the Cold-Seep-Derived Fungus Penicillium oxalicum

Marine Drugs ◽

10.3390/md19010009 ◽

2020 ◽

Vol 19 (1) ◽

pp. 9

Author(s):

Ya-Ping Liu ◽

Sheng-Tao Fang ◽

Zhen-Zhen Shi ◽

Bin-Gui Wang ◽

Xiao-Nian Li ◽

...

Keyword(s):

Deep Sea ◽

Spectroscopic Data ◽

2D Nmr ◽

Penicillium Oxalicum ◽

Marine Phytoplankton ◽

Cold Seep ◽

Phytoplankton Species ◽

X Ray ◽

X Ray Crystallography ◽

Quinazoline Derivatives

Three new phenylhydrazones, penoxahydrazones A–C (compounds 1–3), and two new quinazolines, penoxazolones A (compound 4) and B (compound 5), with unique linkages were isolated from the fungus Penicillium oxalicum obtained from the deep sea cold seep. Their structures and relative configurations were assigned by analysis of 1D/2D NMR and mass spectroscopic data, and the absolute configurations of 1, 4, and 5 were established on the basis of X-ray crystallography or ECD calculations. Compound 1 represents the first natural phenylhydrazone-bearing steroid, while compounds 2 and 3 are rarely occurring phenylhydrazone tautomers. Compounds 4 and 5 are enantiomers that feature quinazoline and cinnamic acid units. Some isolates exhibited inhibition of several marine phytoplankton species and marine-derived bacteria.

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

Molecules ◽

10.3390/molecules23081951 ◽

2018 ◽

Vol 23 (8) ◽

pp. 1951 ◽

Cited By ~ 2

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.

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

Molecules ◽

10.3390/molecules25173927 ◽

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.

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Purification, characterization, crystal structure and NO production inhibitory activity of three new sesquiterpenoids from homalomena occulta

Acta Crystallographica Section C Structural Chemistry ◽

10.1107/s2053229618013815 ◽

2018 ◽

Vol 74 (11) ◽

pp. 1440-1446

Author(s):

Qi Zhang ◽

Li Ma ◽

Zhaoxia Qu ◽

Guige Hou ◽

Yanan Wang ◽

...

Keyword(s):

Crystal Structure ◽

Single Crystal ◽

2D Nmr ◽

Inhibitory Effect ◽

Raw 264.7 Cells ◽

No Production ◽

Raw 264.7 ◽

X Ray Diffraction ◽

X Ray ◽

Spectroscopic Analyses

Two new isodaucane-type sesquiterpenoids, namely (1R,4S,5S,6R,7S,10R)-isodauc-6,7,10-triol, C15H28O3, (1), and (1R,4S,5S,6S,7S,10R)-isodauc-6,7,10-triol, (2), and a new eudesmane-type sesquiterpenoid, 1β,4β,5α-trihydroxyeudesmane, (3), were obtained from the rhizomes of homalomena occulta with the aid of column chromatography. Their structures were elucidated based on extensive spectroscopic analyses, including 1D NMR, 2D NMR and HRESIMS. The structure of (1) was confirmed by single-crystal X-ray diffraction and the absolute configuration was assigned with respect to that of the precursor. The single-crystal structure reveals that adjacent molecules of (1) embrace through two groups of intermolecular O—H...O hydrogen bonds to generate a two-dimensional sheet with a 63-net topology. The three compounds were evaluated for their activity against lipopolysaccharide-induced production of nitrogen oxide (NO) in RAW 264.7 cells, and (1) showed an inhibitory effect on NO production, with IC50 values of 5.7±0.22 µM.

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Secondary metabolites of Phlebopus species from Northern Thailand

Mycological Progress ◽

10.1007/s11557-020-01643-y ◽

2020 ◽

Vol 19 (12) ◽

pp. 1525-1536

Author(s):

Boontiya Chuankid ◽

Hedda Schrey ◽

Benjarong Thongbai ◽

Olivier Raspé ◽

Norbert Arnold ◽

...

Keyword(s):

Secondary Metabolites ◽

2D Nmr ◽

Cytotoxic Activities ◽

Tumor Cell Lines ◽

Submerged Cultures ◽

Esi Ms ◽

Spectroscopic Analyses ◽

New Compounds ◽

Comprehensive Characterization

AbstractSubmerged cultures of the edible mushrooms Phlebopus portentosus and Phlebopus spongiosus were screened for their secondary metabolites by HPLC-UV/Vis and HR-LC-ESI-MS. Two new compounds, 9′-hydroxyphenyl pulvinone (1), containing an unusual pulvinone structure, and phlebopyron (2), together with the seven known pigments, atromentic acid (3), xerocomic acid (4), variegatic acid (5), methyl atromentate (6), methyl isoxerocomate (7), methyl variegatate (8), and variegatorubin (9) were isolated from the cultures. Their structures were assigned on the basis of extensive 1D/2D NMR spectroscopic analyses, as well as HR-ESI-MS, and HR-ESI-MS/MS measurements. Furthermore, the isolated compounds were evaluated for their antimicrobial and cytotoxic properties. 9′-hydroxyphenyl pulvinone (1), xerocomic acid (4), and methyl variegatate (8) exhibited weak to moderate cytotoxic activities against several tumor cell lines. The present paper provides a comprehensive characterization of pigments from the class of pulvinic acids that are present in the basidiomes of many edible bolete species.

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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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