scholarly journals Discovery of New Secondary Metabolites by Epigenetic Regulation and NMR Comparison from the Plant Endophytic Fungus Monosporascus eutypoides

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4192
Author(s):  
Zhe Guo ◽  
Zhong-Mei Zou
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
Chemical Diversity ◽  
Ionization Mass ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Planar Structures ◽  
Ionization Mass Spectroscopy ◽  
Epigenetic Manipulation ◽  
New Compounds ◽  
Mcf 7

Overexpression of the histone acetyltransferase and the 1H NMR spectroscopic experiments of the endophytic fungus Monosporascus eutypoides resulted in the isolation of two new compounds, monosporasols A (1) and B (2), and two known compounds, pestaloficin C (3) and arthrinone (4). Their planar structures and absolute configurations were determined by spectroscopic analysis including high resolution electrospray ionization mass spectroscopy (HRESIMS), one-dimensional (1D) and two-dimensional (2D) NMR, and calculated electronic circular dichroism data. Compounds 1–2 were screened in cytotoxic bioassays against HeLa, HCT-8, A549 and MCF-7 cells. Our work highlights the enormous potential of epigenetic manipulation along with the NMR comparison as an effective strategy for unlocking the chemical diversity encoded by fungal genomes.

scholarly journals New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750

Marine Drugs ◽  
2021 ◽  
Vol 19 (9) ◽  
pp. 483
Author(s):  
Kuo Yong ◽  
Sidra Kaleem ◽  
Bin Wu ◽  
Zhizhen Zhang
Keyword(s):  
Chemical Degradation ◽  
Ionization Mass ◽  
X Ray Diffraction ◽  
Penicillium Sp ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Rice Medium ◽  
Antiglioma Activity ◽  
New Compounds

Seven novel compounds, namely peniresorcinosides A–E (1–5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8–17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher’s method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.

scholarly journals Two New Compounds from Rhizomes of Musa basjoo

2019 ◽  
Vol 14 (12) ◽  
pp. 1934578X1989343
Author(s):  
Li Jiang ◽  
Yang Wang ◽  
Min-Hui Zhu ◽  
Lin Zheng ◽  
Lin-Zhen Li ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Carboxylic Acid ◽  
High Resolution ◽  
Spectroscopic Analysis ◽  
Acid Ethyl Ester ◽  
Ethanol Extract ◽  
Ionization Mass ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
New Compounds

Two new compounds, rel-(3 S,4a R,10b R)-3-(4′-methoxyphenyl)-8-hydroxy-9-methoxy-4a,5,6,10b-tetrahydro-3 H-naphtho[2,1-b]pyran (1), 7-hydroxy- 2-phenylnaphthalene-1-carboxylic acid ethyl ester (2), were isolated from the 70% ethanol extract of the rhizomes of Musa basjoo. Their structures were determined on the basis of spectroscopic analysis including 1-dimensional (1D), 2D nuclear magnetic resonance and high-resolution electrospray ionization mass spectroscopy.

scholarly journals Pestalotiones A–D: Four New Secondary Metabolites from the Plant Endophytic Fungus Pestalotiopsis Theae

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 470 ◽  
Author(s):  
Longfang Guo ◽  
Jie Lin ◽  
Shubin Niu ◽  
Shuchun Liu ◽  
Ling Liu
Keyword(s):  
Endophytic Fungus ◽  
Diphenyl Ether ◽  
2D Nmr ◽  
Hela Cell Line ◽  
Dpph Radical ◽  
Xanthone Derivatives ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
Mcf 7

Two new xanthone derivatives, pestalotiones A (1) and B (2), one new diphenyl ketone riboside, pestalotione C (7), and one new diphenyl ether, pestalotione D (8), along with five known compounds isosulochrin dehydrate (3), 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (4), isosulochrin (5), chloroisosulochrin (6), and pestalotether D (9), were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). The structures of the new compounds were unambiguously deduced by HRESIMS and 1D/2D-NMR spectroscopic data. Compound 6 showed modest cytotoxicity against the HeLa cell line with an IC50 value of 35.2 μM. Compound 9 also showed cytotoxic to the HeLa and MCF-7 cell lines, with IC50 values of 60.8 and 22.6 μM, respectively. Additionally, compounds 1 and 2 exhibited antioxidant activity in scavenging DPPH radical with IC50 values of 54.2 and 59.2 μg/mL, respectively.

scholarly journals Chemical Constituents and Their Activities From the Seeds of Ormosia hosiei

2019 ◽  
Vol 14 (7) ◽  
pp. 1934578X1985997
Author(s):  
Huiyou Xu ◽  
Yatie Qiu ◽  
Jingxin Chen ◽  
Yan Shi ◽  
Xiaoqin Zhang ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Nmr Spectroscopy ◽  
High Resolution ◽  
Chemical Constituents ◽  
Ionization Mass ◽  
Cytotoxic Effects ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Mcf 7 ◽  
C Nmr

A new cytisine-like alkaloid, hosimonoal (1), with a fused monoterpene group, and 6 known compounds (2-6) were isolated from the seeds of Ormosia hosiei Hemsl. et Wils. The structure of the new compound was confirmed by high resolution electrospray ionization mass spectroscopy (HRESIMS), 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, and electronic circular dichroism, and the others by 1H and 13C NMR spectroscopy and comparison with the literature data. In addition, compounds 1, 2, 3, and 6 showed moderate cytotoxic effects against A2780, A-549, HepG2, and MCF-7 cell lines with IC50 values ranging from 5.7 to 36.5 μM.

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.

Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha

2021 ◽  
Vol 76 (5-6) ◽  
pp. 213-218
Author(s):  
Usama W. Hawas ◽  
Lamia T. Abou El-Kassem ◽  
Radwan Al-farawati ◽  
Fekri M. Shaher
Keyword(s):  
2D Nmr ◽  
Cytotoxic Activities ◽  
Dpph Radical ◽  
Srb Assay ◽  
Phenolic Metabolites ◽  
2D Nmr Spectra ◽  
New Compounds ◽  
Benzaldehyde Derivatives ◽  
Mcf 7

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.

scholarly journals Fe(III)-doxycycline complexes with diimine ligands: Syntheses, characterization and biological properties

2019 ◽  
Vol 38 (1) ◽  
pp. 29
Author(s):  
Joshua A Obaleye ◽  
Olufunso Olumide Abosede
Keyword(s):  
Binding Constants ◽  
Biological Properties ◽  
Axial Position ◽  
Klebsiella Pneumonia ◽  
Ionization Mass ◽  
Polypyridyl Ligands ◽  
Diimine Ligands ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Ct Dna

Three new iron(III) complexes of doxycycline viz: [Fe(dox)2Cl]Cl2 (1), [Febpy(dox)Cl]Cl2 (2) and [Fephen(dox)Cl]Cl2 (3), where dox is doxycycline, bpy is 2,2ʹ-bipyridine and phen is 1,10-phenanthroline, were synthesized and characterized by elemental analysis, electronic absorption, FT-IR, and electrospray ionization mass spectroscopy. Doxycycline and the polypyridyl ligands behave as bidendate ligands; the polypyridyl ligands coordinate through the two diimine nitrogen atoms and doxycycline through enolate and diketoamide oxygen atoms of ring A in a five-coordinate system with chloride atom in the axial position. Their antibacterial and antiplasmodial activities against chloroquine-sensitive Plasmodium falciparum NF54 and their interaction with calf thymus (CT) DNA using electronic titration were investigated. The three complexes showed good activity against strains of Staphylococcus aureus and Klebsiella pneumonia. The complexes bind moderately to CT DNA with binding constants of 5.6 × 104 and 4.8 × 104 for complexes 2 and 3, respectively.

scholarly journals Conjugated Polyene Ketones From the Marine Sponge Clathria (Thalysias) Reinwardti (Vosmaer, 1880) and Their Cytotoxic Activity

2021 ◽  
Vol 16 (9) ◽  
pp. 1934578X2110437
Author(s):  
Bui H. Tai ◽  
Dan T. Hang ◽  
Do T. Trang ◽  
Pham H. Yen ◽  
Phan T. T. Huong ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Marine Sponge ◽  
Human Cancer ◽  
2D Nmr ◽  
Ionization Mass ◽  
Hep G2 ◽  
Human Cancer Cells ◽  
Resolution Electron ◽  
New Compounds ◽  
First Time

Five conjugated polyene ketones (1-5) were isolated from the methanol extract of the marine sponge Clathria ( Thalysias) reinwardti (Vosmaer, 1880) living in the coastal waters of Vietnam. Their structures were determined to be 8-(2′,3′,4′-trimethylphenyl)-6-methyl-oct-3( E),5( E),7( E)-trien-2-one (1), 13-apoastaxanthinone (2), 9-apoastaxanthinone (3), 2,3-dehydro-4-oxo- β-ionone (4), and 4-(2′,3′,4′-trimethylphenyl)-but-3( E)-en-2-one (5), by extensive analysis of high-resolution electron spray ionization mass spectrum (HR-ESI-MS), one-dimensional, and two-dimensional (2D) nuclear magnetic resonance (NMR) spectra, as well as by comparison of the spectral data with those reported in the literature. Compound 1 was new, compounds 2 to 4 were isolated from nature for the first time, and the chemical structure as well as the NMR assignments, of 5 were indicated by 2D NMR for the first time. Additionally, compound 5 exhibited cytotoxic activity against the human cancer cells SK-LU-1, SK-Mel-2, MCF-7, and Hep-G2 with half-minimal inhibitory concentration (IC50) values of 15.12 ± 3.43, 17.41 ± 2.83, 33.12 ± 3.39, and 34.38 ± 3.52 µM, respectively, but displayed only a weak cytotoxic effect on the normal HEK-239A cells (IC50 64.67 ± 3.67 µM). Compound 5 also significantly increased Caspase-3 activity in SK-LU-1 cells at concentrations of 10, 15, and 20 µM.

Homoadamantane and Adamantane Acylphloroglucinols from Hypericum hirsutum

Planta Medica ◽  
2021 ◽  
Author(s):  
Julianna Max ◽  
Jörg Heilmann
Keyword(s):  
Petroleum Ether Extract ◽  
2D Nmr ◽  
Positive Control ◽  
Ionization Mass ◽  
2D Nmr Spectroscopy ◽  
Vitro Assay ◽  
Ionization Mass Spectroscopy ◽  
Ic50 Values ◽  
Adamantane Skeleton

Abstract 1H NMR-guided fractionation of the petroleum ether extract of the aerial parts from Hypericum hirsutum yielded to the isolation of 19 polyprenylated polycyclic acylphloroglucinols. Structure elucidation based on 1D and 2D NMR spectroscopy together with high-resolution electrospray ionization mass spectroscopy revealed 14 acylphloroglucinols with a homoadamantane scaffold (1–14), while 5 further compounds showed an adamantane skeleton (15–19). Except for hookerione C (15), all isolated metabolites are hitherto unknown. While structurally-related metabolites have been isolated from other Hypericum species, it is the first report of admantan and homoadamantan type acylphloroglucinols in section Taeniocarpium Jaub. & Spach (Hypericaceae). The isolated compounds have been tested in a crystal violet-based in vitro assay on their properties to reduce the proliferation of human microvascular endothelial cells compared to hyperforin as the positive control. They showed a moderate reduction of proliferation with IC50 values in the range ~ 3 – 22 µM, with the homoadamantane-based compounds 2 and 4 being the most active. In addition, inhibition of the TNF-α-induced ICAM-1 expression was determined for 1 – 5, 7, and 10 – 12. Substances 3 and 12 reduced the ICAM-1 expression significantly (to 46.7% of control for 3, 62.3% for 12, at 50 µM).

scholarly journals Novel Bioactive Penicipyrroether A and Pyrrospirone J from the Marine-Derived Penicillium sp. ZZ380

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 292 ◽  
Author(s):  
Tengfei Song ◽  
Mingmin Tang ◽  
Hengju Ge ◽  
Mengxuan Chen ◽  
Xiaoyuan Lian ◽  
...  
Keyword(s):  
Inhibitory Concentration ◽  
Structural Type ◽  
Ionization Mass ◽  
Isolation And Identification ◽  
Penicillium Sp ◽  
Electrospray Ionization Mass Spectroscopy ◽  
Ionization Mass Spectroscopy ◽  
Fused Ring ◽  
Ic50 Values ◽  
Fused Ring System

The marine-sourced fungus Penicillium sp. ZZ380 was previously reported to have the ability to produce a series of new pyrrospirone alkaloids. Further investigation on this strain resulted in the isolation and identification of novel penicipyrroether A and pyrrospirone J. Each of them represents the first example of its structural type, with a unique 6/5/6/5 polycyclic fusion that is different from the 6/5/6/6 fused ring system for the reported pyrrospirones. Their structures were elucidated by extensive nuclear magnetic resonance (NMR) and high resolution electrospray ionization mass spectroscopy (HRESIMS) spectroscopic analyses, electronic circular dichroism (ECD) and 13C NMR calculations and X-ray single crystal diffraction. Penicipyrroether A showed potent antiproliferative activity against human glioma U87MG and U251 cells with half maximal inhibitory concentration (IC50) values of 1.64–5.50 μM and antibacterial inhibitory activity with minimum inhibitory concentration (MIC) values of 1.7 μg/mL against methicillin-resistant Staphylococcus aureus and 3.0 μg/mL against Escherichia coli.

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