scholarly journals A New Pyrrolidine Derivative and Steroids from an Algicolous Gibberella zeae Strain

2011 ◽  
Vol 6 (9) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Xiang-Hong Liu ◽  
Xiao-Zhen Tang ◽  
Feng-Ping Miao ◽  
Nai-Yun Ji
Keyword(s):  
Cell Lines ◽  
Green Alga ◽  
Endophytic Fungus ◽  
2D Nmr ◽  
Gibberella Zeae ◽  
Spectroscopic Techniques ◽  
Codium Fragile ◽  
Relative Stereochemistry ◽  
Marine Green Alga

A new pyrrolidine derivative, 3-hydroxy-5-(hydroxymethyl)-4-(4′-hydroxyphenoxy)pyrrolidin-2-one (1), and eight known steroids, (22 E,24 R)-7β,8β-epoxy-3β,5α,9α-trihydroxyergosta-22-en-6-one (2, a reassigned structure of (22 E,24 R)-5α,6α-epoxy-3β,8β,14α-trihydroxyergosta-22-en-7-one), (22 E,24 R)-3β,5α,9α-trihydroxyergosta-7,22-dien-6-one (3), (22 E,24 R)-3β,5α-dihydroxyergosta-7,22-dien-6-one (4), (22 E,24 R)-ergosta-7,22-dien-3β,5α,6β-triol (5), (22 E,24 R)-ergosta-5,22-dien-3β-ol (6), (22 E,24 R)-5α,8α-epidioxyergosta-6,22-dien-3β-ol (7), (22 E,24 R)-5α,8α-epidioxyergosta-6,9(11),22-trien-3β-ol (8), and (22 E,24 R)-1(10→6)- abeo-ergosta-5,7,9,22-tetraen-3α-ol (9), were isolated from the cultures of Gibberella zeae, an endophytic fungus isolated from the marine green alga Codium fragile. Their structures and relative stereochemistry were elucidated by 1D, 2D NMR and mass spectroscopic techniques. Compound 1 showed cytotoxicity against A-549 and BEL-7402 cell lines.

scholarly journals Coumarin-Based Triapine Derivatives and Their Copper(II) Complexes: Synthesis, Cytotoxicity and mR2 RNR Inhibition Activity

Biomolecules ◽  
2021 ◽  
Vol 11 (6) ◽  
pp. 862
Author(s):  
Iryna Stepanenko ◽  
Maria V Babak ◽  
Gabriella Spengler ◽  
Marta Hammerstad ◽  
Ana Popovic-Bijelic ◽  
...  
Keyword(s):  
Cell Lines ◽  
2D Nmr ◽  
Multidrug Resistant ◽  
Lung Fibroblasts ◽  
Spectroscopic Techniques ◽  
Tyrosyl Radical ◽  
X Ray Diffraction ◽  
Healthy Human ◽  
12 Steps ◽  
Esi Mass Spectrometry

A series of thiosemicarbazone-coumarin hybrids (HL1-HL3 and H2L4) has been synthesised in 12 steps and used for the preparation of mono- and dinuclear copper(II) complexes, namely Cu(HL1)Cl2 (1), Cu(HL2)Cl2 (2), Cu(HL3)Cl2 (3) and Cu2(H2L4)Cl4 (4), isolated in hydrated or solvated forms. Both the organic hybrids and their copper(II) and dicopper(II) complexes were comprehensively characterised by analytical and spectroscopic techniques, i.e., elemental analysis, ESI mass spectrometry, 1D and 2D NMR, IR and UV–vis spectroscopies, cyclic voltammetry (CV) and spectroelectrochemistry (SEC). Re-crystallisation of 1 from methanol afforded single crystals of copper(II) complex with monoanionic ligand Cu(L1)Cl, which could be studied by single crystal X-ray diffraction (SC-XRD). The prepared copper(II) complexes and their metal-free ligands revealed antiproliferative activity against highly resistant cancer cell lines, including triple negative breast cancer cells MDA-MB-231, sensitive COLO-205 and multidrug resistant COLO-320 colorectal adenocarcinoma cell lines, as well as in healthy human lung fibroblasts MRC-5 and compared to those for triapine and doxorubicin. In addition, their ability to reduce the tyrosyl radical in mouse R2 protein of ribonucleotide reductase has been ascertained by EPR spectroscopy and the results were compared with those for triapine.

scholarly journals Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols

2021 ◽  
Vol 17 ◽  
pp. 983-990
Author(s):  
Ákos Bajtel ◽  
Mounir Raji ◽  
Matti Haukka ◽  
Ferenc Fülöp ◽  
Zsolt Szakonyi
Keyword(s):  
Alkaline Hydrolysis ◽  
Stereoselective Synthesis ◽  
2D Nmr ◽  
Ring Closure ◽  
Spectroscopic Techniques ◽  
Reductive Alkylation ◽  
X Ray ◽  
Relative Stereochemistry ◽  
Hydrolysis Of

A library of pinane-based 2-amino-1,3-diols was synthesised in a stereoselective manner. Isopinocarveol prepared from (−)-α-pinene was converted into condensed oxazolidin-2-one in two steps by carbamate formation followed by a stereoselective aminohydroxylation process. The relative stereochemistry of the pinane-fused oxazolidin-2-one was determined by 2D NMR and X-ray spectroscopic techniques. The regioisomeric spiro-oxazolidin-2-one was prepared in a similar way starting from the commercially available (1R)-(−)-myrtenol (10). The reduction or alkaline hydrolysis of the oxazolidines, followed by reductive alkylation resulted in primary and secondary 2-amino-1,3-diols, which underwent a regioselective ring closure with formaldehyde or benzaldehyde delivering pinane-condensed oxazolidines. During the preparation of 2-phenyliminooxazolidine, an interesting ring–ring tautomerism was observed in CDCl3.

scholarly journals Cyclonerane Derivatives from the Algicolous Endophytic Fungus Trichoderma asperellum A-YMD-9-2

Marine Drugs ◽  
2019 ◽  
Vol 17 (5) ◽  
pp. 252 ◽  
Author(s):  
Yin-Ping Song ◽  
Feng-Ping Miao ◽  
Xiang-Hong Liu ◽  
Xiu-Li Yin ◽  
Nai-Yun Ji
Keyword(s):  
Endophytic Fungus ◽  
Structural Diversity ◽  
2D Nmr ◽  
Red Alga ◽  
Gracilaria Verrucosa ◽  
Marine Phytoplankton ◽  
Spectroscopic Techniques ◽  
Phytoplankton Species ◽  
Trichoderma Asperellum ◽  
Potent Inhibition

Seven previously unreported cyclonerane derivatives, namely, 3,7,11-trihydroxycycloneran-10-one, cycloneran-3,7,10,11-tetraol, cycloneran-3,7,11-triol, 11,12,15-trinorcycloneran-3,7,10-triol, 7,10S-epoxycycloneran-3,15-diol, 7,10R-epoxycycloneran-3,15-diol, and (10Z)-15-acetoxy-10-cycloneren-3,7-diol, were isolated in addition to the known (10Z)-cyclonerotriol, (10E)-cyclonerotriol, catenioblin C, and chokol E from the culture of Trichoderma asperellum A-YMD-9-2, an endophytic fungus obtained from the marine red alga Gracilaria verrucosa. The structures of previously unreported compounds were established by spectroscopic techniques, including 1D/2D NMR, MS, and IR. The isolation of these new cyclonerane derivatives greatly adds to the structural diversity of unusual cyclonerane sesquiterpenes, and several isolates exhibit potent inhibition against some marine phytoplankton species.

scholarly journals A Novel Sesquiterpene Polyol Ester from the Celastrus Rosthornianus with Anti-tumor Activities

2006 ◽  
Vol 1 (7) ◽  
pp. 1934578X0600100 ◽  
Author(s):  
Kuiwu Wang ◽  
Yuanjiang Pan
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Human Tumor ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Polyol Ester ◽  
Human Tumor Cell Lines ◽  
Polyol Esters

A new (1) and a known (2) β-dihydroagarofuran sesquiterpene polyol esters were isolated from Celastrus rosthornianus and their structures were established by 1D- and 2D-NMR spectroscopic techniques. The two compounds exhibited anti-tumor activities against a panel of human tumor cell lines.

scholarly journals Additional New Tetracyclic Tetraterpenoid: Methyl Tortuoate D from Soft Coral Sarcophyton tortuosum

2009 ◽  
Vol 4 (9) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Wen-Jian Lan ◽  
Shou-Liang Wang ◽  
Hou-Jin Li
Keyword(s):  
Mass Spectrometry ◽  
South China Sea ◽  
Electrospray Ionization ◽  
South China ◽  
Soft Coral ◽  
2D Nmr ◽  
Ionization Mass ◽  
Spectroscopic Techniques ◽  
Direct Infusion ◽  
Relative Stereochemistry

Under the guidance of chemical prescreening by direct infusion electrospray ionization mass spectrometry (DI ESI-MS), a new tetracyclic tetraterpenoid, methyl tortuoate D (1) was isolated from the soft coral Sarcophyton tortuosum collected from the South China Sea. Its structure and relative stereochemistry were established by MS, and 1D- and 2D-NMR spectroscopic techniques.

scholarly journals Chemical Constituents from an Endophytic Fungus Chaetomium Globosum Z1

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800
Author(s):  
Chun-Yan Zhang ◽  
Xiao Ji ◽  
Xuan Gui ◽  
Bao-Kang Huang
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Endophytic Fungus ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Chaetomium Globosum ◽  
Spectroscopic Methods ◽  
Esi Ms

A new ergosterol, 15β-hydroxyl-(22 E,24 R)-ergosta-3,5,8,22-tetraen-one (1), along with three known ergosterols, two known cytochalasins, and two known azapholines were isolated from Chaetomium globosum Z1. The structures of these compounds were elucidated on the basis of spectroscopic methods (HR-ESI-MS, 1D NMR, and 2D NMR). Compound 6 showed significant cytotoxic activity against A-549 and MG-63 cell lines with IC50 values of 6.96 and 1.73 μg/mL, respectively.

scholarly journals Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Antibiotics ◽  
2020 ◽  
Vol 9 (11) ◽  
pp. 753
Author(s):  
Elodie Gisèle M. Anoumedem ◽  
Bel Youssouf G. Mountessou ◽  
Simeon F. Kouam ◽  
Abolfazl Narmani ◽  
Frank Surup
Keyword(s):  
Endophytic Fungus ◽  
2D Nmr ◽  
In Vitro Cytotoxicity ◽  
Coupling Constants ◽  
Broth Culture ◽  
Spectroscopic Techniques ◽  
Cytotoxic Effects ◽  
Relative Configuration ◽  
Planar Structures

Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.

scholarly journals A New Sesquiterpene from an Endophytic Aspergillus versicolor Strain

2012 ◽  
Vol 7 (7) ◽  
pp. 1934578X1200700
Author(s):  
Xiang-Hong Liu ◽  
Feng-Ping Miao ◽  
Xiao-Dong Li ◽  
Xiu-Li Yin ◽  
Nai-Yun Ji
Keyword(s):  
Escherichia Coli ◽  
Acetic Acid ◽  
Carboxylic Acid ◽  
Brine Shrimp ◽  
2D Nmr ◽  
Spectroscopic Techniques ◽  
Aspergillus Versicolor ◽  
Codium Fragile ◽  
Staphyloccocus Aureus ◽  
Indole 3 Acetic Acid

A new sesquiterpene, albican-11,14-diol (1), and seven known compounds, including sterigmatocystin (2), 3-hydroxy-5-(hydroxymethyl)-4-(4′-hydroxyphenoxy) pyrrolidin-2-one (3), (1 H-indol-3-yl) oxoacetamide (4), indole-3-carboxylic acid (5), indole-3-acetic acid (6), indole-3-carboxaldehyde (7), and volemolide (8), were isolated from the cultures of Aspergillus versicolor, an endophytic fungus isolated from the marine green alga Codium fragile. The structure of 1 was elucidated by 1D, 2D NMR and mass spectroscopic techniques. The bioassay results showed that 1 possessed potent activity against brine shrimp, Escherichia coli, and Staphyloccocus aureus.

Two new glycosidal metabolites of endophytic fungus Penicillium sp. (NO.4) from Tapiscia sinensis

2016 ◽  
Vol 71 (4) ◽  
pp. 283-286 ◽  
Author(s):  
Qiao Wan ◽  
Ziwei Feng ◽  
Xueshuang Li ◽  
Mengmeng Lv ◽  
Zhiyong Guo ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Cell Lines ◽  
Cancer Cell ◽  
Endophytic Fungus ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Antimicrobial Activities ◽  
Cytotoxic Activities ◽  
A549 Cancer Cell Line

AbstractTwo new glycosides, 8-O-β-d-glucopyranosyl-6-methyl-1-carboxylate methyl ester xanthone (1) and 4′-O-β-d-galactopyranosyl djalonensone (2), together with four known compounds, 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate methyl ester (3), cassionllin (4), djalonensone (5) and alternariol (6), were isolated from the endophytic fungus Penicillium sp. (NO.4) of Tapiscia sinensis Oliv. The structures of compounds 1–6 were elucidated by the analysis of 1D and 2D NMR and HRMS. The cytotoxic activities of these compounds were evaluated against four cancer cell lines, as well as antimicrobial activities against two plant-pathogenic microbes. Compounds 1–6 showed moderate cytotoxicity against the A549 cancer cell line with IC50 values ranging from 6.8 to 35.8 μg mL−1 and were found to be inactive against three other cancer cell lines MCF-7, Caski and Hep G-2.

scholarly journals A New Polyketide from the Endophytic Fungus Penicillium chermesinum

2017 ◽  
Vol 17 (3) ◽  
pp. 360 ◽  
Author(s):  
Cici Darsih ◽  
Vilailak Prachyawarakorn ◽  
Chulabhorn Mahidol ◽  
Somsak Ruchirawat ◽  
Prasat Kittakoop
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Endophytic Fungus ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Esi Ms

A new polyketide derivative, 2-chloro-3,4,7-trihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one (1), was isolated from the endophytic fungus Penicillium chermesinum. The structure was established on the basis of UV, IR, HR-ESI MS, and 1D and 2D NMR experiments. The cytotoxicity against four cancer cell lines (HuCCA-1, HepG2, A-549, and MOLT-3) of compound 1 are 14.94-115.71 µM.

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