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1.
Fitoterapia ; 177: 106130, 2024 Sep.
Article in English | MEDLINE | ID: mdl-39032912

ABSTRACT

A fungus strain, Neopestalotiopsis clavispora AL01, was isolated from the leaf spot of the plant Phoenix dactylifera. Further chemical investigation of the fermentation extract of this strain afforded six new secondary metabolites (1-6), along with 11 known compounds (7-17) which included a new natural compound (7). Their structures were determined by extensive spectroscopic analysis including one-and two-dimensional (1D and 2D) NMR spectroscopy, high-resolution electrospray ionization mass spectrometry (HRESIMS), and ECD and NMR calculations. All compounds were evaluated for their phytotoxic activities. Among them, compounds 10, 12 and 13 exhibited phytotoxic activities against Nicotiana tabacum. Compound 3 exhibited weak antibacterial activity against methicillin-resistant Staphylococcus aureus, Micrococcus luteus and Vibrio harveyi. Taken collectively, these findings establish a solid research foundation for future investigations on bioactive natural products derived from phytopathogenic fungi.


Subject(s)
Anti-Bacterial Agents , Polyketides , Terpenes , Molecular Structure , Anti-Bacterial Agents/pharmacology , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/chemistry , Polyketides/pharmacology , Polyketides/isolation & purification , Polyketides/chemistry , Terpenes/pharmacology , Terpenes/isolation & purification , Plant Leaves/chemistry , Nicotiana , Microbial Sensitivity Tests , China , Biological Products/pharmacology , Biological Products/isolation & purification , Biological Products/chemistry , Methicillin-Resistant Staphylococcus aureus/drug effects
2.
Mar Drugs ; 22(6)2024 Jun 11.
Article in English | MEDLINE | ID: mdl-38921581

ABSTRACT

A marine-derived fungal strain, Aspergillus sp. ITBBc1, was isolated from coral collected from the South China Sea in Hainan province. Intensive chemical investigation of the fermentation extract of this strain afforded four new secondary metabolites (1-4), named megastigmanones A-C and prenylterphenyllin H, along with four known compounds (5-8). Their structures were elucidated by extensive spectroscopic analysis including one-and two-dimensional (1D and 2D) NMR spectroscopy and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). The modified Mosher's method was undertaken to determine the absolute configurations of new compounds. The phytotoxic activity test showed that compounds 6-8 exhibited significant antagonistic activity against the germination of Triticum aestivum L. and Oryza sativa L. seeds with a dose-dependent relationship.


Subject(s)
Anthozoa , Aspergillus , Triticum , Aspergillus/metabolism , Aspergillus/chemistry , Anthozoa/microbiology , Animals , Triticum/microbiology , Oryza/microbiology , Secondary Metabolism , Magnetic Resonance Spectroscopy , Seeds , China , Germination/drug effects , Molecular Structure
3.
Org Lett ; 25(22): 4203-4207, 2023 06 09.
Article in English | MEDLINE | ID: mdl-37232514

ABSTRACT

Chemical investigation of Streptomyces sp. NA07423 led to the discovery of two unreported macrolactams, nagimycins A (1) and B (2). Their structures were elucidated by NMR, HRESIMS, X-ray crystallography, and comparison of experimental and theoretical ECD spectra. The nagimycins have a unique butenolide moiety rarely found in ansamycin antibiotics. Genome analysis revealed the putative biosynthetic gene cluster for nagimycins, and a likely biosynthetic pathway was proposed. Notably, compounds 1 and 2 exhibited potent antibacterial activity against two pathogenic Xanthomonas bacteria.


Subject(s)
Rifabutin , Streptomyces , Lactams, Macrocyclic/chemistry , Rifabutin/chemistry , Streptomyces/chemistry , Anti-Bacterial Agents/chemistry , Magnetic Resonance Spectroscopy
4.
Molecules ; 27(21)2022 Oct 29.
Article in English | MEDLINE | ID: mdl-36364185

ABSTRACT

The secondary metabolites of the phytopathogenic fungus Corynespora cassiicola CC01 from Hevea brasiliensis were investigated. As a result, two new compounds, 5-acetyl-7-hydroxy-6- methoxybenzofuran-2(3H)-one (1) and (S)-2-(2,3-dihydrofuro [3,2-c]pyridin-2-yl)propan-2-ol (2), together with seven known compounds, 4,6,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one (3), 3,6,8-trihydroxy-3,4-dihydronaphthalen-1(2H)-one (4), curvulin acid (5), 2-methyl-5-carboxymethyl- 7-hydroxychromone (6), tyrosol (7), p-hydroxybenzoic acid (8) and cerevisterol (9), were isolated from the fermentation extract by comprehensive silica gel, reverse phase silica gel, Sephadex-LH20 column chromatography and high-performance liquid chromatography (HPLC). The structures of these compounds were identified by using high-resolution electrospray mass spectrometry (HRESIMS), nuclear magnetic resonance spectroscopy (NMR), optical rotation, ultraviolet and infrared spectroscopy techniques and a comparison of NMR data with those reported in the literature. Compounds 1 and 2 were new compounds, and compounds 3-9 were discovered from this phytopathogenic fungus for the first time. Compounds 1-9 were tested for phytotoxicity against the fresh tender leaf of Hevea brasiliensis, and the results show that none of them were phytotoxic. Additionally, these compounds were subjected to an antimicrobial assay against three bacteria (E. coli, methicillin-resistant Staphylococcus aureus and Micrococcus luteus), but they showed no activity.


Subject(s)
Ascomycota , Hevea , Methicillin-Resistant Staphylococcus aureus , Hevea/chemistry , Silica Gel , Escherichia coli
5.
Mar Drugs ; 20(11)2022 Oct 28.
Article in English | MEDLINE | ID: mdl-36355001

ABSTRACT

Chemical investigation of the fermentation extract of the coral-associated fungus Aspergillus sp. ITBBc1 led to the discovery of five unreported p-terphenyl derivatives, sanshamycins A-E (1-5), together with five previously described analogues, terphenyllin (6), 3-hydroxyterphenyllin (7), candidusin A (8), 4,5-dimethoxycandidusin A (9), and candidusin C (10). Their structures were elucidated by HRESIMS data and NMR spectroscopic analysis. Compound 1 represents the first example of p-terphenyls with an aldehyde substitution on the benzene ring. Compounds 2-4 feature varying methoxyl and isopentenyl substitutions, while compound 5 features a five-membered lactone linked to a biphenyl. These findings expand the chemical diversity of the family of p-terphenyl natural products. Compounds 1-6 and 9 were evaluated for their inhibitory activity against type 4 phosphodiesterase (PDE4), which is a fascinating drug target for treatment of inflammatory, respiratory, and neurological diseases. Compound 3 was the most potent and exhibited PDE4D inhibitory activity with an IC50 value of 5.543 µM.


Subject(s)
Agaricales , Anthozoa , Biological Products , Animals , Phosphodiesterase Inhibitors/metabolism , Aspergillus/chemistry , Biological Products/pharmacology , Biological Products/metabolism , Anthozoa/metabolism , Phosphoric Diester Hydrolases/metabolism , Molecular Structure
6.
Mar Genomics ; 18 Pt B: 119-21, 2014 Dec.
Article in English | MEDLINE | ID: mdl-25176559

ABSTRACT

Halomonas sp. FS-N4 is a bacterium, which can grow in the medium Marine Broth 2216 with 5M initial hydrogen peroxide concentration, shows a strong oxidation resistance, and the crude enzyme activity can reach as high as 13.33katal/mg. We reported the draft genome sequence of H. sp. FS-N4, showing that it contains 3434 protein-coding genes, including the genes putatively involved in the response to the oxidative stress, among which a phytochrome-like gene might be a key point to survive in the environment with high concentration of hydrogen peroxide and exhibit high catalase activity.


Subject(s)
Catalase/metabolism , Genome, Bacterial/genetics , Halomonas/enzymology , Halomonas/genetics , Base Sequence , Cluster Analysis , Computational Biology , DNA Primers/genetics , Hydrogen Peroxide/analysis , Molecular Sequence Data , Phylogeny , RNA, Ribosomal, 16S/genetics , Sequence Analysis, DNA
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