Aspernolides L and M, new butyrolactones from the endophytic fungus Aspergillus versicolor

2017 ◽  
Vol 72 (5-6) ◽  
pp. 155-160 ◽  
Author(s):  
Sabrin R.M. Ibrahim ◽  
Gamal A. Mohamed ◽  
Samir A. Ross
Keyword(s):  
Endophytic Fungi ◽  
Endophytic Fungus ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Systematic Search ◽  
Aspergillus Versicolor ◽  
Active Compounds ◽  
Etoac Extract ◽  
First Time

Abstract During the systematic search of active compounds from endophytic fungi, two new butyrolactones, namely aspernolides L (2) and M (4), together with four known compounds: 1-O-acetylglycerol (1), butyrolactone I (3), butyrolactone VI (5), and (+) alantrypinone (6) were characterized from the EtOAc extract of the endophytic fungus Aspergillus versicolor isolated from the roots of Pulicaria crispa (Asteraceae). Extensive spectroscopic analysis, including 1D, 2D NMR, and HRESIMS, was used to elucidate their structures. Compounds 1, 5, and 6 are reported for the first time from this fungus.

scholarly journals Two Compounds from the Endophytic Colletotrichum sp. of Ginkgo biloba

2011 ◽  
Vol 6 (8) ◽  
pp. 1934578X1100600
Author(s):  
Sheng-Liang Zhou ◽  
Song-Lin Zhou ◽  
Mei-Xia Wang ◽  
Shuang-Lin Chen
Keyword(s):  
Spectral Data ◽  
Ginkgo Biloba ◽  
Endophytic Fungus ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Fermentation Products ◽  
First Time

Two compounds, apigenin-8- C-β-D-glucopyranoside and 2-(hydroxymethylthio)ethanol, were extracted from the fermentation products of a strain of endophytic fungus, Colletotrichum sp. NTB-2, isolated from the leafstalk of Ginkgo biloba. The structures of the two compounds were determined on the basis of extensive spectroscopic analysis, including 1D and 2D NMR spectral data. The compounds were obtained from microorganisms for the first time.

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

Molecules ◽  
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.

Glucosides from the Fresh Flowers of Juglans regia L. and Their Biological Evaluation

2019 ◽  
Vol 17 (1) ◽  
pp. 31-35
Author(s):  
Haibo Wang ◽  
Xikui Liu
Keyword(s):  
Spectroscopic Analysis ◽  
Juglans Regia ◽  
2D Nmr ◽  
Antibacterial Activities ◽  
Biological Evaluation ◽  
Chemical Investigation ◽  
Etoac Extract

The chemical investigation of the EtOAc extract of the fresh flowers of Juglans regia L. resulted in a new α-tetralonyl glucoside (1) and two known glucosides (2-3). The structure of the new compound was determined by extensive 1D and 2D NMR spectroscopic analysis and HRESIMS. The biological evaluation of the obtained glucosides showed that compound 1 and 3 displayed good antioxidant and antibacterial activities. These two compounds were identified as the main functional molecules in the fresh flowers of Juglans regia L.

scholarly journals Prenylated Phenol and Benzofuran Derivatives from Aspergillus terreus EN-539, an Endophytic Fungus Derived from Marine Red Alga Laurencia okamurai

Marine Drugs ◽  
2019 ◽  
Vol 17 (11) ◽  
pp. 605 ◽  
Author(s):  
Li ◽  
Li ◽  
Yang ◽  
Meng ◽  
Li ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Density Functional ◽  
Aspergillus Terreus ◽  
Optical Rotation ◽  
2D Nmr ◽  
Red Alga ◽  
Spectrometric Data ◽  
Phenol Derivatives ◽  
First Time ◽  
Laurencia Okamurai

Three new prenylated phenol derivatives, terreprenphenols A–C (1–3), along with four known related compounds (4–7), were isolated from Aspergillus terreus EN-539, an endophytic fungus obtained from the marine red alga Laurencia okamurai. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, and optical rotation (OR). The corresponding relationship between absolute configuration and optical rotation for known compounds anodendroic acid (4) and asperterreusine C (5) was ambiguous in literature, and their absolute configurations were therefore discussed and confirmed for the first time by time-dependent density functional (TDDFT) ECD and OR calculations. Compounds 1–7 inhibited some common aquatic bacteria with MIC values ranging from 2 to 64 μg/mL.

A New Chlorine-containing Glucosyl-fused Compound from Curculigo glabrescens

2009 ◽  
Vol 64 (9) ◽  
pp. 1077-1080 ◽  
Author(s):  
Cui-Cui Zhu ◽  
Tian-Ming Wang ◽  
Kai-Jin Wang ◽  
Ning Li
Keyword(s):  
Spectroscopic Analysis ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
2D Nmr ◽  
Free Radical Scavenging ◽  
Scavenging Activity ◽  
Dpph Assay ◽  
Etoh Extract ◽  
Structure Activity ◽  
First Time

A new chlorine-containing glucosyl-fused compound, crassifoside H (1), was isolated from the EtOH extract of the rhizomes of Curculigo glabrescens. The structure was established on the basis of MS, IR, 1D and 2D NMR experiments. In addition, seven known compounds (2 - 8) were isolated and identified by spectroscopic analysis and comparison of their spectral data with those reported previously. All the compounds were isolated from this plant for the first time. The free radical scavenging activity of the isolated compounds was evaluated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Compounds 1 and 2 showed strong radical scavenging activities. The primary structure-activity relationship is also discussed.

scholarly journals Secondary Metabolites Produced by an Endophytic Fungus Pestalotiopsis microspora

2019 ◽  
Vol 9 (6) ◽  
pp. 411-417 ◽  
Author(s):  
G. R. Nalin Rathnayake ◽  
N. Savitri Kumar ◽  
Lalith Jayasinghe ◽  
Hiroshi Araya ◽  
Yoshinori Fujimoto
Keyword(s):  
Acetic Acid ◽  
Secondary Metabolites ◽  
Chromatographic Separation ◽  
Endophytic Fungus ◽  
Potato Dextrose Broth ◽  
Etoac Extract ◽  
Manilkara Zapota ◽  
Pestalotiopsis Microspora ◽  
First Time

Abstract An endophytic fungus Pestalotiopsis microspora isolated from the fruits of Manilkara zapota was cultured in potato dextrose broth media. Chromatographic separation of the EtOAc extract of the broth and mycelium led to the isolation of a new azaphilonoid named pitholide E (1), in addition to previously identified pitholide B (2), pitholide D (3), pestalotin (LL-P880α) (4), PC-2 (5), LL-P880β (6), tyrosol (7) and 4-oxo-4H-pyran-3-acetic acid (8). An endophytic fungus P. microspora from M. zapota and the isolation of compounds 1–5, 7 and 8 from P. microspora are reported here for the first time. Graphic Abstract

scholarly journals Endophytic Mycobiota of Schinus molle L., (Anacardiaceae) and Peganum harmala L., (Tetradiclidaceae) in Algeria

2020 ◽  
Vol 8 (1) ◽  
pp. 413
Author(s):  
Khamssa Rouabah ◽  
Berna Tunali ◽  
Nadia Lombarkia ◽  
Oussama Ali Bensaci
Keyword(s):  
Endophytic Fungi ◽  
North Africa ◽  
Aerial Part ◽  
Peganum Harmala ◽  
Active Compounds ◽  
Cosmopolitan Species ◽  
Schinus Molle ◽  
The World ◽  
First Time

Schinus molle is an arborescent plant that is common in North Africa. It has insecticidal and pharmaceutical activities that are assigned to some active compounds. Harmel is a cosmopolitan species extensively distributed in the world and very common in Algeria especially in the Sahara. This plant is very rich in alkaloids of the β-carbolines group of which most important are harmine. It has pharmaceutical and agrochemical virtues. Endophytic fungi were isolated from aerial part (leaves and fruits) of Peruvian peppertree (S. molle L.) Anacardiaceae and for the first time of the Harmel (Peganum harmala L.) Tetradiclidaceae.Twenty three mycotaxa were identified whose eleven isolated from S. molle and twelve isolated from the second plant. The vast majority are included in mitosporic group (Deuteromycota). The frequency of colonization or infection (FC%) at leaves of the two plants species is significant comparatively to the fruits.

Antimicrobial Materials Derived from the Endophytic Fungus Fusarium sp. of Eucommia ulmoides

2012 ◽  
Vol 531 ◽  
pp. 346-349 ◽  
Author(s):  
Hong Chi Zhang ◽  
Yang Min Ma ◽  
Rui Liu
Keyword(s):  
Endophytic Fungus ◽  
Spectroscopic Analysis ◽  
Screening Program ◽  
Eucommia Ulmoides ◽  
Antibacterial And Antifungal Activities ◽  
Antimicrobial Materials ◽  
Fusarium Sp ◽  
Reported Data ◽  
Antibacterial And Antifungal ◽  
First Time

Within our screening program for antimicrobial materials, eight compounds (1-8) were isolated from an endophytic fungus Fusarium sp. of Eucommia ulmoides. Compound 1, 2, 5-8 were isolated for the first time from endophytic fungi. Their structures were elucidated on the basis of NMR spectroscopic analysis with the reported data in the literature. All compounds showed potent antibacterial and antifungal activities and can be use as new antimicrobial materials.

Cytotoxic and Pro-apoptotic Activities of Diterpenoids from Zhumeria Majdae

2020 ◽  
Vol 17 ◽  
Author(s):  
Abolfazl Shakeri ◽  
Samira Navabi Nejad ◽  
Javad Asili ◽  
Milena Masullo ◽  
Mansoor Saeidi ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cytotoxic Effect ◽  
Therapeutic Agent ◽  
2D Nmr ◽  
Etoac Extract ◽  
Chemical Structures ◽  
Ic50 Value ◽  
Cytotoxic Compounds ◽  
First Time ◽  
Mcf 7

Abstract:: Since the ethylacetate (EtOAc) extract of the roots of Zhumeria majdae had the potent cytotoxic effect (IC50 < 50 μg/ml) on three cancer cell lines; MCF-7, PC3 and MDA-MB-231, therefore the purpous of this study is to isolation of the responcible cytotoxic compounds from the plant. Isolation of the extract led to the identification of four diterpenoids named as lanugon Q (1), 12,16-dideoxy aegyptinone B (2), 12-deoxy-salvipisone (3) and manool (4). The chemical structures have been determined on the basis of 1D and 2D NMR experiments. Compound 1 is reported for the first time in the plants of Zhumeria genus. The results of cytotoxic and apoptotic evaluation revealed that compound 2 had the strong cytotoxic effect with the IC50 value of 15.90 μg/ml against MCF-7 cell lines. Sub-G1 peak in flow cytometry histogram of cells treated with EtOAc axtract and compound 2 showed the induction of apoptosis. Changes in the Bax/Bcl-2 ratio and cleavage of PARP were observed. It is to be noted that owing to strong cytotoxic effect, Z. majdae extract could be represented as therapeutic agent against cancer.

scholarly journals New Phenylpropanoid-Substituted Flavan-3-ols from Pu-er Ripe Tea

2014 ◽  
Vol 9 (8) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Mu-Ke Tao ◽  
Min Xu ◽  
Hong-Tao Zhu ◽  
Rong-Rong Cheng ◽  
Dong Wang ◽  
...  
Keyword(s):  
Green Tea ◽  
Camellia Sinensis ◽  
Spectroscopic Analysis ◽  
2D Nmr ◽  
Cd Spectra ◽  
Beneficial Effects ◽  
The Past ◽  
First Time ◽  
Fermentative Process

Pu-er ripe tea is a special microbial post-fermented tea made from Pu-er raw tea, a kind of green tea produced from the leaves of Camellia sinensis var. assamica. It is one of the most consumed teas in the past two decades in China, due to its special flavor, taste, and beneficial effects. This work aimed to obtain diverse catechin structures from Pu-er ripe tea, which led to the isolation of four new phenylpropanoid-substituted flavan-3-ols, puerins C-F (1-4), together with four known flavan-3-ols, (+)-catechin (5), (-)-epicatechin (6), (±)-gallocatechin (7), and (-)-epigallocatechin (8). Their structures were elucidated on the basis of detailed spectroscopic analysis, including 1D and 2D NMR, mass and CD spectra. Compounds 1-4, which could be formed in the post-fermentative process of Pu-er tea, were isolated for the first time from tea and Theaceae plant.

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