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.

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

Marine Drugs ◽  
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.

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.

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 New Diphenylketones and a New Xanthone from Talaromyces islandicus EN-501, an Endophytic Fungus Derived from the Marine Red Alga Laurencia okamurai

Marine Drugs ◽  
2016 ◽  
Vol 14 (12) ◽  
pp. 223 ◽  
Author(s):  
Hong-Lei Li ◽  
Xiao-Ming Li ◽  
Hui Liu ◽  
Ling-Hong Meng ◽  
Bin-Gui Wang
Keyword(s):  
Endophytic Fungus ◽  
Red Alga ◽  
Laurencia Okamurai

Cytotoxic 24-nor-ursane-type triterpenoids from the twigs of Mostuea hirsuta

2015 ◽  
Vol 70 (11) ◽  
pp. 837-842 ◽  
Author(s):  
Jean Pierre Longue Ekon ◽  
Achille Nouga Bissoue ◽  
Marie Fomani ◽  
Flavien Aristide Alfred Toze ◽  
Alain François Waffo Kamdem ◽  
...  
Keyword(s):  
Methanol Extract ◽  
2D Nmr ◽  
Adenocarcinoma Cell Line ◽  
2D Nmr Spectroscopy ◽  
Spectrometric Data ◽  
Spectroscopic Analyses ◽  
Paper Disk ◽  
Standard Doxorubicin ◽  
First Time ◽  
Diffusion Assay

AbstractTwo new 24-nor-ursane-type triterpenoids, 2α,3β,19α-trihydroxy-24-norurs-4(23),12-dien-28-oic acid (1) and 3β-acetoxy-2α,19α-dihydroxy-24-norurs-4(23),12-dien-28-oic acid (2), along with 15 known compounds were isolated from the methanol extract of the twigs of Mostuea hirsuta. While 2-hydroxymethylbenzamide (13) was isolated for the first time from the natural source, compounds 3–12 are reported here for the first time from the genus Mostuea. Their structures were elucidated by means of spectroscopic analyses including 1D- and 2D-NMR spectroscopy, high-resolution mass spectrometric data as well as comparison with data from the literature. Compounds 1, 2, 4–9 and 13 were tested against bacteria, fungi and plant pathogen oomycetes by the paper disk agar diffusion assay resulting in missing to low activities corresponding with minimum inhibitory concentrations (MICs) > 1 mg mL–1. However, the respective compounds 1, 2, 8, 9 and 13 exhibited moderate cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC50 10.6–16.5 μm compared to the standard doxorubicin with IC50 0.9 μm.

scholarly journals Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291

2016 ◽  
Vol 12 ◽  
pp. 2012-2018 ◽  
Author(s):  
Peng Zhang ◽  
Xiao-Ming Li ◽  
Xin-Xin Mao ◽  
Attila Mándi ◽  
Tibor Kurtán ◽  
...  
Keyword(s):  
Endophytic Fungus ◽  
Density Functional ◽  
Indole Derivative ◽  
Marine Alga ◽  
2D Nmr ◽  
Paecilomyces Variotii ◽  
Functional Theory ◽  
Nmr Data ◽  
Hepg2 Cell Lines ◽  
C Nmr

A new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative, varioloid A (1), was isolated from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291. Its structure was elucidated on the basis of extensive analysis of 1D and 2D NMR data and the absolute configuration was determined by time-dependent density functional theory-electronic circular dichroism (TDDFT-ECD) calculations. A similar compound, whose planar structure was previously described but the relative and absolute configurations and 13C NMR data were not reported, was also identified and was tentatively named as varioloid B (2). Both compounds 1 and 2 exhibited cytotoxicity against A549, HCT116, and HepG2 cell lines, with IC50 values ranging from 2.6 to 8.2 µg/mL.

scholarly journals New Antifungal Cholestane and Aldehyde Derivatives from the Red Alga Laurencia papillosa

2011 ◽  
Vol 6 (12) ◽  
pp. 1934578X1100601 ◽  
Author(s):  
Walied M. Alarif ◽  
Sultan S. Al-Lihaibi ◽  
Ahmed Abdel-Lateff ◽  
Seif-Eldin N. Ayyad
Keyword(s):  
Saudi Arabia ◽  
Candida Albicans ◽  
Antifungal Activity ◽  
Methanol Extract ◽  
2D Nmr ◽  
Red Alga ◽  
Mass Spectrometric ◽  
First Time ◽  
Chloroform Methanol ◽  
Aldehyde Derivative

The chloroform/methanol extract of the red alga, Laurencia papillosa, collected from the Red Sea in Saudi Arabia, was found to contain two cholestane derivatives: 3α, 6α-dihydroxy-5β-cholestan-12-one (1) and the known, 6β-hydroxycholest-4-en-3-one (2), which was isolated separately in a pure form for the first time. In addition to these compounds, a new aldehyde derivative, ( E)-2-{( E) tridec-2-en-2-yl} heptadec-2-enal (3), was isolated. The structures of all compounds were established based on extensive spectroscopic (1D and 2D NMR, UV, IR) and mass spectrometric studies. All compounds, except 2, were tested for their antifungal activity. Significant activities were associated with 1 and 3 against Candida albicans, Aspergillus fumigatus, and A. flavus.

scholarly journals Chemical Composition and Biological Activities of Soldiers of the Brazilian Termite Species, Nasutitermes macrocephalus (Isoptera: Natutitermitinae)

2013 ◽  
Vol 8 (1) ◽  
pp. 1934578X1300800
Author(s):  
Márcia N. S. de la Cruz ◽  
Helvécio M. S. Júnior ◽  
Denilson F. Oliveira ◽  
Letícia V. Costa-Lotufo ◽  
Antonio G. Ferreira ◽  
...  
Keyword(s):  
Biological Activities ◽  
Optical Rotation ◽  
2D Nmr ◽  
Positive Bacterium ◽  
Specific Optical Rotation ◽  
Frontal Gland ◽  
Chemical Structures ◽  
Lack Of Information ◽  
First Time ◽  
Termite Soldiers

The defensive secretion of the frontal gland from termite soldiers is a mixture of monoterpenes, sesquiterpenes and diterpenes, the latter being the most representative. Analyses of the dichloromethane extract from soldiers of the Brazilian termite, Nasutitermes macrocephalus (Silvestri, 1903) (Isoptera, Nasutitermitinae), described for the first time, allowed to identify the presence of two monoterpenes (α-pinene and limonene) and two sesquiterpenes (β-trans- caryophyllene and α-selinene) by GC-EIMS, and the isolation of one rippertane and six trinervitane diterpenes by RP-HPLC. The chemical structures of the purified compounds were elucidated by interpretation of their spectroscopic data (1D and 2D NMR, EIMS, HRESIMS, and specific optical rotation) and the complete unequivocal assignment of the 3α-hydroxy-trinervita-1(15),8(19)-dien-2-one (6) was included in this paper, to complement the lack of information in the literature. Antibacterial, antifungal and cytotoxicity against cancer cell lines activities were evaluated. In particular, the compounds 2α,3β-dihydroxy- trinervita-1(15),8(19)-diene (2) and 3α-hydroxy-15-rippertene (7) exhibited the better activities against the clinically isolated Gram-positive bacterium methicillin-resistant Staphylococcus aureus BMB 9393, both with a MIC value of 31.2 μg mL−1. This is the first description of a rippertane diterpene (7) as an antibacterial agent.

scholarly journals Chemical Constituents from Stems of Pileostegia viburnoides

2019 ◽  
Vol 14 (1) ◽  
pp. 1934578X1901400
Author(s):  
Xiao-Jun Li ◽  
Kwan-Woo Kim ◽  
Qin-Peng Zou ◽  
Zu-Zhen Liu ◽  
Hyun-Cheol Oh ◽  
...  
Keyword(s):  
Optical Rotation ◽  
Chemical Constituents ◽  
2D Nmr ◽  
Spatial Structures ◽  
H Nmr ◽  
Mass Data ◽  
Phytochemical Investigation ◽  
Coumarin Glycoside ◽  
First Time ◽  
Nmr Signals

Phytochemical investigation on the stems of Pileostegia viburnoides Hook.f.et Thoms led to the isolation of twelve compounds, including two steroids (1 and 10), two fatty compounds (2 and 12), seven triterpenoids (3–9), and one coumarin glycoside (11). 24-methylene-5α-dammara-20(21)-en-3β-yl acetate (5), a rare dammarane-tetracyclic triterpene had been first reported just according to the typical 1H-NMR signals analysis, melting point and optical rotation in 1975. However, the complete and reliable NMR and mass data were still unknown. This is the first time to identify the planar and spatial structures of compound 5 by the analysis of 1D-, 2D-NMR, mass data and other physicochemical properties, as well as by comparison of the spectral data with the literature. Further more, the anti-inflammatory and anti-neuroinflammatory activities of dammarane-type triterpenes 4 and 5 were evaluated.

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