Scalarane Sesterterpenoids with Antibacterial and Anti-Proliferative Activities from the Mushroom Neonothopanus nambi

Seven undescribed scalarane sesterterpenoids, nambiscalaranes B–H (1–7), together with two known compounds, nambiscalarane (8) and aurisin A (9) were isolated from the cultured mycelium of the luminescent mushroom Neonothopanus nambi. Their structures were elucidated by thorough analysis of their 1D and 2D NMR spectroscopic data. The absolute configurations of 1–8 were determined by electronic circular dichroism (ECD) calculations and optical rotation measurements. The isolated sesterterpenoids were evaluated against A549, HT29, HeLa, and HCT-116 cancer cell lines, and against five bacterial strains. Compounds 3, 5, and 7 showed strong cytotoxicity against HCT-116 cell line, with IC50 values ranging from 13.41 to 16.53 µM, and showed no cytotoxicity towards Vero cells. Moreover, compound 8 inhibited the growth of Bacillus subtilis with a MIC value of 8 µg/mL, which was equivalent to the MIC value of the standard kanamycin.

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Pyrenosetin D, a New Pentacyclic Decalinoyltetramic Acid Derivative from the Algicolous Fungus Pyrenochaetopsis sp. FVE-087

Marine Drugs ◽

10.3390/md18060281 ◽

2020 ◽

Vol 18 (6) ◽

pp. 281

Author(s):

Bicheng Fan ◽

Pradeep Dewapriya ◽

Fengjie Li ◽

Laura Grauso ◽

Martina Blümel ◽

...

Keyword(s):

Cell Line ◽

Acid Derivative ◽

Optical Rotation ◽

Chemical Study ◽

2D Nmr ◽

Human Malignant Melanoma ◽

Chemical Structures ◽

Isolation And Characterization ◽

Ic50 Values ◽

Fungal Genus

The fungal genus Pyrenochaetopsis is commonly found in soil, terrestrial, and marine environments, however, has received little attention as a source of bioactive secondary metabolites so far. In a recent work, we reported the isolation and characterization of three new anticancer decalinoyltetramic acid derivatives, pyrenosetins A–C, from the Baltic Fucus vesiculosus-derived endophytic fungus Pyrenochaetopsis sp. FVE-001. Herein we report a new pentacyclic decalinoylspirotetramic acid derivative, pyrenosetin D (1), along with two known decalin derivatives wakodecalines A (2) and B (3) from another endophytic strain Pyrenochaetopsis FVE-087 isolated from the same seaweed and showed anticancer activity in initial screenings. The chemical structures of the purified compounds were elucidated by comprehensive analysis of HR-ESIMS, FT-IR, [α]D, 1D and 2D NMR data coupled with DFT calculations of NMR parameters and optical rotation. Compounds 1–3 were evaluated for their anticancer and toxic potentials against the human malignant melanoma cell line (A-375) and the non-cancerous keratinocyte cell line (HaCaT). Pyrenosetin D (1) showed toxicity towards both A-375 and HaCaT cells with IC50 values of 77.5 and 39.3 μM, respectively, while 2 and 3 were inactive. This is the third chemical study performed on the fungal genus Pyrenochaetopsis and the first report of a pentacyclic decalin ring system from the fungal genus Pyrenochaetopsis.

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Synthesis and Antibacterial Activity of New Spiro[thiadiazoline-(pyrazolo[3,4-d]pyrimidine)] Derivatives

Journal of Chemistry ◽

10.1155/2015/982404 ◽

2015 ◽

Vol 2015 ◽

pp. 1-6 ◽

Cited By ~ 1

Author(s):

Mohammed El Fal ◽

Youssef Ramli ◽

Abdelfettah Zerzouf ◽

Ahmed Talbaoui ◽

Youssef Bakri ◽

...

Keyword(s):

Staphylococcus Aureus ◽

Antibacterial Activity ◽

Spectroscopic Data ◽

Heterocyclic Compounds ◽

Dipolar Cycloaddition ◽

Bacterial Strains ◽

Pyrimidine Derivatives ◽

H Nmr ◽

Biological Interest ◽

Mic Value

New heterocyclic compounds spiroderivatives of allopurinol of biological interest were prepared from allopurinol via thionation and 1,3-dipolar cycloaddition and were produced in high to excellent yields. These compounds were characterized on the basis of spectral and spectroscopic data (1H NMR,13C, IR, and MS). The antibacterial activity of the synthesized products was studied using bacterial strains:Staphylococcus aureus,Enterococcus faecalis,Escherichia coli, andPseudomonas aeruginosa. Compounds having an ethyl group showed the best activity with MIC value of 31.25 µg/mL againstStaphylococcus aureusandStreptococcus fasciens.

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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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Oxygenated Acyclic Diterpenes with Anticancer Activity from the Irish Brown Seaweed Bifurcaria bifurcata

Marine Drugs ◽

10.3390/md18110581 ◽

2020 ◽

Vol 18 (11) ◽

pp. 581

Author(s):

Vangelis Smyrniotopoulos ◽

Christian Merten ◽

Daria Firsova ◽

Howard Fearnhead ◽

Deniz Tasdemir

Keyword(s):

Cell Line ◽

Brown Seaweed ◽

Cancer Cell Line ◽

Structural Diversity ◽

Chemical Study ◽

2D Nmr ◽

Chemical Structures ◽

Bifurcaria Bifurcata ◽

Ic50 Values ◽

Ft Ir

Brown alga Bifurcaria bifurcata is a prolific source of bioactive acyclic (linear) diterpenes with high structural diversity. In the continuation of our investigations on Irish brown algae, we undertook an in-depth chemical study on the n-hexanes and chloroform subextracts of B. bifurcata that led to isolation of six new (1–6) and two known (7–8) acyclic diterpenes. Chemical structures of the compounds were elucidated by a combination of 1D and 2D NMR, HRMS, FT-IR, [α]D and vibrational circular dichroism (VCD) spectroscopy. Compounds 1–8, as well as three additional linear diterpenes (9–11), which we isolated from the same seaweed before, were tested against the human breast cancer cell line (MDA-MB-231). Several compounds moderately inhibited the growth of the MDA-MB-231 cell line with IC50 values ranging from 11.6 to 32.0 μg/mL. The present study carried out on the lipophilic extracts of the Irish B. bifurcata shows the enormous capacity of this seaweed to produce a large palette of acyclic diterpenes with diverse oxygenation and substitution patterns and promising bioactivities.

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Flavonoids from Milletia leucantha and Their Cytotoxicity

Natural Product Communications ◽

10.1177/1934578x1801300810 ◽

2018 ◽

Vol 13 (8) ◽

pp. 1934578X1801300

Author(s):

Uraiwan Sriphana ◽

Chavi Yenjai ◽

Siriporn Tungnoi ◽

Jongjai Srirapa ◽

Auemporn Junsongduang

Keyword(s):

Cytotoxic Activity ◽

Vero Cell ◽

Cell Line ◽

Vero Cells ◽

2D Nmr ◽

Nmr Techniques ◽

Vero Cell Lines ◽

First Time ◽

Flavonol Derivatives ◽

Mcf 7

Two known chalcones (1–2), five known flavonol derivatives (3 and 5–8) and one flavone (4) were isolated for the first time from fruits of Millettia leucantha Kurz. In addition, 5 was found for the first time from this genus. Their structures were elucidated on the basis of IR, MS, 1D and 2D NMR techniques. Chalcone 1 exhibited moderate cytotoxicity against the MCF-7 cell line with an IC50 value of 50.93 μM, whereas this compound showed inactive cytotoxicity against Vero cells. Compound 2 exhibited cytotoxicity against the KB, NCI-H187 and Vero cell lines with IC50 values of 63.64, 114.44 and 28.44 μM, respectively. Compound 8 only showed cytotoxic activity against the KB cell line with an IC50 value of 110.23 μM.

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Astrotricoumarin, an antiproliferative 4′-hydroxy-2′,3′-dihydroprenylated methylcoumarin from an Astrotrichilia sp. from the Madagascar dry forest[1]

Natural Product Communications ◽

10.1177/1934578x1100600913 ◽

2011 ◽

Vol 6 (9) ◽

pp. 1934578X1100600 ◽

Cited By ~ 1

Author(s):

Liva Harinantenaina ◽

Peggy J. Brodie ◽

Martin W. Callmander ◽

Richard Randrianaivo ◽

Stephan Rakotonandrasana ◽

...

Keyword(s):

Cell Line ◽

Endemic Species ◽

Spectroscopic Data ◽

Ethanol Extract ◽

2D Nmr ◽

Dry Forest ◽

Nmr Analysis ◽

A2780 Cell ◽

Bioassay Guided Fractionation ◽

A2780 Cell Line

Bioassay guided fractionation of the ethanol extract of a new endemic species of the genus Astrotrichilia led to the isolation of the new antiproliferative 3-(4′-hydroxy-2′,3′-dihydroprenyl)-4,6-dimethoxy-5-methylcoumarin, named astrotricoumarin (8) with an IC50 value of 6.8 μM against the A2780 cell line. The structure of compound 8 was elucidated on the basis of its physical and spectroscopic data, including extensive 1D- and 2D-NMR analysis.

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Dimeric 1,4-benzoquinone Derivatives with Cytotoxic Activities from the Marine-Derived Fungus Penicillium sp. L129

Marine Drugs ◽

10.3390/md17070383 ◽

2019 ◽

Vol 17 (7) ◽

pp. 383 ◽

Cited By ~ 1

Author(s):

Zhang ◽

Ju ◽

Li ◽

Sun ◽

Peng ◽

...

Keyword(s):

Quorum Sensing ◽

Cell Lines ◽

Inhibitory Activity ◽

Spectroscopic Data ◽

Cytotoxic Activities ◽

Penicillium Sp ◽

Ic50 Values ◽

Cytotoxicity Activities ◽

Mic Value ◽

Mcf 7

Two new dimeric 1,4-benzoquinone derivatives, peniquinone A (1) and peniquinone B (2), a new dibenzofuran penizofuran A (3), and a new pyrazinoquinazoline derivative quinadoline D (4), together with 13 known compounds (5–17), were isolated from a marine-derived fungus Penicillium sp. L129. Their structures, including absolute configurations, were elucidated by extensive spectroscopic data and electronic circular dichroism calculations. Compound 1 exhibited cytotoxicity against the MCF-7, U87 and PC3 cell lines with IC50 values of 12.39 µM, 9.01 µM and 14.59 µM, respectively, while compound 2 displayed relatively weak cytotoxicity activities against MCF-7, U87 and PC3 cell lines with IC50 values of 25.32 µM, 13.45 µM and 19.93 µM, respectively. Furthermore, compound 2 showed weak quorum sensing inhibitory activity against Chromobacterium violaceum CV026 with an MIC value of 20 μg/well.

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Melicope moluccana Antimalarial Activity of Furoquinoline Alkaloids from the Leaves of Melicope moluccana

Journal Of Tropical Pharmacy And Chemistry ◽

10.25026/jtpc.v5i2.260 ◽

2020 ◽

Vol 5 (2) ◽

pp. 138-142

Author(s):

Ryan Ayub Wahjoedi ◽

Ratih Dewi Saputri ◽

Tjitjik Srie Tjahjandarie ◽

Mulyadi Tandjung

Keyword(s):

Plasmodium Falciparum ◽

Spectral Data ◽

Spectroscopic Data ◽

Chemical Structure ◽

Antimalarial Activity ◽

2D Nmr ◽

Esi Ms ◽

Ic50 Values

Two furoquinoline alkaloids, leptanoine C (1) and haplopine-3,3´-dimethylallyl ether (2) were isolated from the leaves of Melicope moluccana. The chemical structure of both compounds was determined based on spectroscopic data, including UV, IR, HR-ESI-MS, 1D, and 2D NMR spectral data. The antimalarial activity of compounds 1-2 against Plasmodium falciparum 3D7 showing their IC50 values are 0.18 ppm and 2.28 µg/mL, respectively.

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Induction of Secondary Metabolites from the Marine-Derived Fungus Aspergillus versicolor through Co-cultivation with Bacillus subtilis

Planta Medica ◽

10.1055/a-0835-2332 ◽

2019 ◽

Vol 85 (06) ◽

pp. 503-512 ◽

Cited By ~ 11

Author(s):

Nada Abdel-Wahab ◽

Sebastian Scharf ◽

Ferhat Özkaya ◽

Tibor Kurtán ◽

Attila Mándi ◽

...

Keyword(s):

Bacillus Subtilis ◽

Circular Dichroism ◽

Density Functional ◽

2D Nmr ◽

Fungal Culture ◽

Aspergillus Versicolor ◽

Electronic Circular Dichroism ◽

Ic50 Values ◽

Culture Extract ◽

Circular Dichroïsm

AbstractA new cyclic pentapeptide, cotteslosin C (1), a new aflaquinolone, 22-epi-aflaquinolone B (3), and two new anthraquinones (9 and 10), along with thirty known compounds (2, 4 – 8, 11 – 34) were isolated from a co-culture of the sponge-associated fungus Aspergillus versicolor with Bacillus subtilis. The new metabolites were only detected in the co-culture extract, but not when the fungus was grown under axenic conditions. Furthermore, the co-culture extract exhibited an enhanced accumulation of the known constituents versicolorin B (14), averufin (16), and sterigmatocyctin (19) by factors of 1.5, 2.0, and 4.7, respectively, compared to the axenic fungal culture. The structures of the isolated compounds were elucidated on the basis of 1D and 2D NMR spectra and mass spectrometry as well as by comparison with literature data. The absolute configuration of compounds 3, 9, and 10 was determined by ECD (electronic circular dichroism) analysis aided by TDDFT-ECD (time-dependent density functional theory electronic circular dichroism) calculations. Compounds 15, 18 – 21, and 26 exhibited strong to moderate cytotoxic activity against the mouse lymphoma cell line L5178Y, with IC50 values ranging from 2.0 to 21.2 µM, while compounds 14, 16, 31, 32, and 33 displayed moderate inhibitory activities against several gram-positive bacteria, with MIC values ranging from 12.5 to 50 µM.

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Antiplasmodial Bis-Indole Alkaloids from the Bark of Flindersia pimenteliana

Planta Medica ◽

10.1055/a-1028-7786 ◽

2019 ◽

Vol 86 (01) ◽

pp. 19-25 ◽

Cited By ~ 2

Author(s):

Luke P. Robertson ◽

Leonardo Lucantoni ◽

Vicky M. Avery ◽

Anthony R. Carroll

Keyword(s):

Plasmodium Falciparum ◽

Spectroscopic Data ◽

Indole Alkaloids ◽

2D Nmr ◽

Antiplasmodial Activity ◽

Structure Activity Relationships ◽

Structure Activity ◽

Ic50 Values ◽

Significant Attention

AbstractThree new (1–3) and 2 known (4–5) bis-indole alkaloids were identified from the bark of Flindersia pimenteliana (Rutaceae). The structures of 1–3 were elucidated on the basis of their (+)-HRESESIMS and 2D NMR spectroscopic data. Antiplasmodial activity for 1–3 against chloroquine sensitive (3D7) and chloroquine-resistant (Dd2) Plasmodium falciparum is also reported, with IC50 values ranging from 0.96 to 2.41 µg/mL. These results expand our knowledge of the structure-activity relationships of potently antiplasmodial isoborreverine-type alkaloids, the bioactivity of which have recently attracted significant attention in the literature.

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