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

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

Marine Drugs ◽

10.3390/md18080426 ◽

2020 ◽

Vol 18 (8) ◽

pp. 426 ◽

Cited By ~ 1

Author(s):

Senhua Chen ◽

Yanlian Deng ◽

Chong Yan ◽

Zhenger Wu ◽

Heng Guo ◽

...

Keyword(s):

Secondary Metabolites ◽

2D Nmr ◽

X Ray ◽

X Ray Crystallography ◽

Spectroscopic Analyses ◽

Structure Activity ◽

Ic50 Values ◽

Alternaria Sp ◽

Modified Mosher’S Method ◽

Oxide Inhibition

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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Labdane and Abietane Diterpenoids from Juniperus oblonga and Their Cytotoxic Activity

Molecules ◽

10.3390/molecules24081561 ◽

2019 ◽

Vol 24 (8) ◽

pp. 1561 ◽

Cited By ~ 1

Author(s):

Qiao ◽

Khutsishvili ◽

Alizade ◽

Atha ◽

Borris

Keyword(s):

Cell Lines ◽

Human Tumor ◽

2D Nmr ◽

Human Tumor Cell Lines ◽

Abietane Diterpenoids ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Values ◽

First Time ◽

Mcf 7

A phytochemical investigation of the whole plant of Juniperus oblonga led to the isolationof one previously undescribed labdane diterpenoid, (4R,5S,9S,10R)‐13‐des‐ethyl‐13‐oxolabda‐8(17),11E‐dien‐19‐oic acid (1), together with nine known diterpenoids (2–3, 6–12), two lignans (4, 5),and a coumarin (13). The structures of all the compounds were elucidated on the basis ofspectrometric data, primarily one‐dimensional (1D)‐ and two‐dimensional (2D)‐NMR and massspectrometry. Electronic circular dichroism (ECD) calculations determined the absoluteconfiguration of 1. In addition, the isolated compounds were evaluated for their cytotoxic activityagainst three human tumor cell lines (HepG2, MCF‐7, and HeLa). 6,12‐Dihydroxyabieta‐5,8,11,13‐tetraen‐7‐one (6) showed moderate cytotoxicity against all three cell lines with IC50 values rangingfrom 24.41 μM to 58.39 μM and trilobinone (10) showed weaker activity with IC50 values rangingfrom 56.93 μM to 79.98 μM. None of the isolated diterpenoids have been previously reported fromJuniperus oblonga, and five compounds are here reported from the genus Juniperus for the first time.

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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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Absolute Configuration of Cembrane Diterpenoids from Bursera multijuga

Natural Product Communications ◽

10.1177/1934578x1400900907 ◽

2014 ◽

Vol 9 (9) ◽

pp. 1934578X1400900 ◽

Cited By ~ 2

Author(s):

Juan D. Hernández-Hernández ◽

Hugo A. García-Gutiérrez ◽

Luisa U. Román-Marín ◽

Yunuen I. Torres-Blanco ◽

Carlos M. Cerda-García-Rojas ◽

...

Keyword(s):

Molecular Modeling ◽

Absolute Configuration ◽

2D Nmr ◽

Vibrational Circular Dichroism ◽

Conformational Preference ◽

X Ray Diffraction ◽

X Ray ◽

The Absolute ◽

First Time ◽

Good Agreement

The stems of Bursera multijuga afforded (-)-(1 S,3 E,7 R,8 R,11 E)-7,8-epoxycembra-3,11-dien-1-ol (1) and its acetate 2, together with cembrene A (3), nephthenol (4), and cembrenol (5). The structures of 1 and 2 were elucidated by 1D and 2D NMR, HRESIMS, and X-ray diffraction. The conformational preference of flexible 1 was studied by molecular modeling at the DFT B3LYP/DGDZVP level of theory. Good agreement between calculated and experimental vibrational circular dichroism curves established the absolute configuration of 1. This is the first time that cembrane derivatives have been isolated from the genus Bursera.

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Two Dibenzoquinones from the Fungus Acremonium cavaraeanum

Natural Product Communications ◽

10.1177/1934578x1701201129 ◽

2017 ◽

Vol 12 (11) ◽

pp. 1934578X1701201

Author(s):

Qiao Xu ◽

Miao-Miao Zhang ◽

Shu-Zhen Yana ◽

Lu-Fen Cao ◽

Qiang Lia ◽

...

Keyword(s):

Single Crystal ◽

2D Nmr ◽

X Ray Diffraction ◽

X Ray ◽

First Time

Two symmetrical dibenzoquinone derivatives were isolated from solid cultures of the fungus Acremonium cavaraeanum. Compound 1 was new and identified as 2,7-dihydroxy-3,6,9-trimethyl-9 H-xanthene-1,4,5,8-tetraone. Compound 2 was 3,3’,6,6’-tetrahydroxy-4,4’-dimethyl-1,1’-bi- p-benzoquinone, i.e. oosporein, which was reported from A. cavaraeanum for the first time. The structure of the dibenzoquinone (1) was unambiguously elucidated using a combination of MS, IR, 1D- and 2D-NMR, and the dibenzoquinone (2) was further determined by single-crystal X-ray diffraction.

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Neuroprotective Metabolites from Vietnamese Marine Derived Fungi of Aspergillus and Penicillium Genera

Marine Drugs ◽

10.3390/md18120608 ◽

2020 ◽

Vol 18 (12) ◽

pp. 608

Author(s):

Elena V. Girich ◽

Anton N. Yurchenko ◽

Olga F. Smetanina ◽

Phan Thi Hoai Trinh ◽

Ngo Thi Duy Ngoc ◽

...

Keyword(s):

Molecular Weight ◽

Secondary Metabolites ◽

Cell Viability ◽

Chemical Structure ◽

Aspergillus Terreus ◽

Marine Fungi ◽

2D Nmr ◽

Natural Source ◽

Low Molecular Weight ◽

First Time

Low molecular weight secondary metabolites of marine fungi Aspergillus flocculosus, Aspergillus terreus and Penicillium sp. from Van Phong and Nha Trang Bays (Vietnam) were studied and a number of polyketides, bis-indole quinones and terpenoids were isolated. The structures of the isolated compounds were determined by 1D and 2D NMR and HR-ESI-MS techniques. Stereochemistry of some compounds was established based on ECD data. A chemical structure of asterriquinone F (6) was thoroughly described for the first time. Anthraquinone (13) was firstly obtained from a natural source. Neuroprotective influences of the isolated compounds against 6-OHDA, paraquat and rotenone toxicity were investigated. 4-Hydroxyscytalone (1), 4-hydroxy-6-dehydroxyscytalone (2) and demethylcitreoviranol (3) have shown significant increasing of paraquat- and rotenone-treated Neuro-2a cell viability and anti-ROS activity.

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Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

Marine Drugs ◽

10.3390/md18030164 ◽

2020 ◽

Vol 18 (3) ◽

pp. 164 ◽

Cited By ~ 1

Author(s):

Zhongbin Cheng ◽

Wan Liu ◽

Runzhu Fan ◽

Shouye Han ◽

Yuanli Li ◽

...

Keyword(s):

Deep Sea ◽

Chemical Study ◽

Positive Control ◽

Hydroxyl Group ◽

Etoac Extract ◽

The Third ◽

Ic50 Value ◽

Ic50 Values ◽

New Compounds ◽

First Time

A chemical study of the ethyl acetate (EtOAc) extract from the deep-sea-derived fungus Penicillium thomii YPGA3 led to the isolation of a new austalide meroterpenoid (1) and seven known analogues (2−8), two new labdane-type diterpenoids (9 and 10) and a known derivative (11). The structures of new compounds 1, 9, and 10 were determined by comprehensive analyses via nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data. The absolute configurations of 1, 9, and 10 were determined by comparisons of experimental electronic circular dichroism (ECD) with the calculated ECD spectra. Compound 1 represented the third example of austalides bearing a hydroxyl group at C-5 instead of the conserved methoxy in other known analogues. To our knowledge, diterpenoids belonging to the labdane-type were discovered from species of Penicillium for the first time. Compound 1 showed cytotoxicity toward MDA-MB-468 cells with an IC50 value of 38.9 μM. Compounds 2 and 11 exhibited inhibition against α-glucosidase with IC50 values of 910 and 525 μM, respectively, being more active than the positive control acarbose (1.33 mM).

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A Phenylpropanoid and Biflavonoids from the Needles of Cephalotaxus harringtonia var. harringtonia

Natural Product Communications ◽

10.1177/1934578x1701201132 ◽

2017 ◽

Vol 12 (11) ◽

pp. 1934578X1701201 ◽

Cited By ~ 1

Author(s):

Anju Mendiratta (Nee Chugh) ◽

Rameshwar Dayal ◽

John P. Bartley ◽

Graham Smith

Keyword(s):

Nmr Spectroscopy ◽

Oral Dose ◽

Spectral Data ◽

2D Nmr ◽

Hepatoprotective Activity ◽

X Ray Diffraction ◽

Soluble Extract ◽

2D Nmr Spectroscopy ◽

X Ray ◽

First Time

A phenylpropanoid [2-(3-methoxy-4-hydroxyphenyl)-propane-1,3-diol] (1) together with four known biflavonoids namely 7, 4′, 7′″, 4′″-tetra- O-methyl amentoflavone (2); 7, 4′, 7″-tri- O-methyl amentoflavone (3); ginkgetin (4); sequoiaflavone (5) were isolated from the acetone soluble extract of needles of Cephalotaxus harringtonia var. harringtonia. Their structures were elucidated mainly on the basis of interpretation of 1D and 2D NMR spectroscopy and X-ray diffraction studies. The detailed spectral data of phenylpropanoid have been described for the first time. Ginkgetin (4) exhibited significant hepatoprotective activity in rat at 6 mg/kg oral dose level.

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