Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Austalides S-U, New Meroterpenoids from the Sponge-Derived Fungus Aspergillus aureolatus HDN14-107.

ABSTRACT: Three new meroterpenoids, named austalides S-U (1-3), were isolated from the culture of a sponge-derived fungus Aspergillus aureolatus HDN14-107, together with eleven known austalides derivates (4-14). Their structures, including absolute configurations, were assigned on the basis of NMR, MS data, and TDDFT ECD calculations. Compound 1 is the first case of austalides with the terpene ring fused to the chroman ring in trans configuration. Compounds 3 and 5 exhibited activities against influenza virus A (H1N1), with IC50 values of 90 and 99 ?M, respectively.

SUBMITTER: Peng J

PROVIDER: S-EPMC4962021 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Austalides S-U, New Meroterpenoids from the Sponge-Derived Fungus Aspergillus aureolatus HDN14-107.

Peng Jixing J Zhang Xiaomin X Wang Wei W Zhu Tianjiao T Gu Qianqun Q Li Dehai D

Marine drugs 20160714 7

Three new meroterpenoids, named austalides S-U (1-3), were isolated from the culture of a sponge-derived fungus Aspergillus aureolatus HDN14-107, together with eleven known austalides derivates (4-14). Their structures, including absolute configurations, were assigned on the basis of NMR, MS data, and TDDFT ECD calculations. Compound 1 is the first case of austalides with the terpene ring fused to the chroman ring in trans configuration. Compounds 3 and 5 exhibited activities against influenza v ...[more]

PMID: 27428982

Similar Datasets

New isocoumarin derivatives and meroterpenoids from the marine sponge-associated fungus Aspergillus similanensis sp. nov. KUFA 0013.

Project description:Two new isocoumarin derivatives, including a new 5-hydroxy-8-methyl-2H, 6H-pyrano[3,4-g]chromen-2,6-dione (1) and 6,8-dihydroxy-3,7-dimethylisocoumarin (2b), a new chevalone derivative, named chevalone E (3), and a new natural product pyripyropene S (6) were isolated together with 6, 8-dihydroxy-3-methylisocoumarin (2a), reticulol (2c), p-hydroxybenzaldehyde, chevalone B, chevalone C, S14-95 (4), and pyripyropene E (5) from the ethyl acetate extract of the undescribed marine sponge-associated fungus Aspergillus similanensis KUFA 0013. The structures of the new compounds were established based on 1D and 2D NMR spectral analysis, and in the case of compound 3, X-ray analysis was used to confirm its structure and the absolute configuration of its stereogenic carbons. Compounds 1, 2a-c and 3-6 were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria, Candida albicans ATCC 10231, and multidrug-resistant isolates from the environment. Chevalone E (3) was found to show synergism with the antibiotic oxacillin against methicillin-resistant Staphylococcus aureus (MRSA).

| S-EPMC4210891 | biostudies-literature

New Dihydroisocoumarin Root Growth Inhibitors From the Sponge-Derived Fungus Aspergillus sp. NBUF87.

Project description:Six new dihydroisocoumarins, aspergimarins A-F (1-6), were discovered together with five known analogs (7-11) from a monoculture of the sponge-derived fungus Aspergillus sp. NBUF87. The structures of these compounds were elucidated through comprehensive spectroscopic methods, and absolute configurations were assigned after X-ray crystallography, use of the modified Mosher's method, and comparison of electronic circular dichroism (ECD) data with literature values for previously reported analogs. Compounds 1-11 were evaluated in a variety of bioassays, and at 100 ?M, both 1 and 5 showed significant inhibitory effects on the lateral root growth of Arabidopsis thaliana Columbia-0 (Col-0). Moreover, at 100 ?M, 5 also possessed notable inhibition against the primary root growth of Col-0. Meanwhile, 1-11 were all found to be inactive in vitro against acetylcholinesterase (AChE) (IC50 > 100 ?M), four different types of human-derived cancer cell lines (IC50 > 50 ?M), as well as methicillin-resistant Staphylococcus aureus and Escherichia coli (MIC > 50 ?g/mL), and Plasmodium falciparum W2 (EC50 > 100 ?g/mL), in phenotypic tests.

| S-EPMC6914834 | biostudies-literature

New Anti-inflammatory Cyclopeptides From a Sponge-Derived Fungus Aspergillus violaceofuscus.

Project description:Three new cyclic peptides including a cyclic tetrapeptide (1), an aspochracin-type cyclic tripeptide sclerotiotide L (2) and a diketopiperazine dimer (3), have been isolated from the ethyl acetate extract of a marine sponge-derived fungus Aspergillus violaceofuscus. The structures of all compounds were unambiguously elucidated on the basis of HRESIMS, 1D and 2D NMR spectroscopic data, MS/MS experiments and chemical methods. Compounds 1 and 3 showed anti-inflammatory activity against IL-10 expression of the LPS-induced THP-1 cells with inhibitory rates of 84.3 and 78.1% respectively at concentration of 10 μM.

| S-EPMC6010530 | biostudies-literature

Chevalones H-M: Six New α-Pyrone Meroterpenoids from the Gorgonian Coral-Derived Fungus Aspergillus hiratsukae SCSIO 7S2001.

Project description:Six new α-pyrone meroterpenoid chevalones H-M (1-6), together with six known compounds (7-12), were isolated from the gorgonian coral-derived fungus Aspergillus hiratsukae SCSIO 7S2001 collected from Mischief Reef in the South China Sea. Their structures, including absolute configurations, were elucidated on the basis of spectroscopic analysis and X-ray diffraction data. Compounds 1-5 and 7 showed different degrees of antibacterial activity with MIC values of 6.25-100 μg/mL. Compound 8 exhibited potent cytotoxicity against SF-268, MCF-7, and A549 cell lines with IC50 values of 12.75, 9.29, and 20.11 μM, respectively.

| S-EPMC8781156 | biostudies-literature

Brasilianoids A-F, New Meroterpenoids From the Sponge-Associated Fungus Penicillium brasilianum.

Project description:3,5-Dimethylorsellinic acid (DMOA) derived meroterpenoids comprise an unique class of natural products with diverse scaffolds and with a broad spectrum of bioactivities. Bioinformatics analysis of the gene clusters in association with the qRT-PCR detection of the amplification of two key genes led to speculate that the sponge associated fungus Penicillium brasilianum WZXY-m122-9 is a potential producer of meroterpenoids. Chromatographic separation of the EtOAc extract of this fungal strain on a large-scale fermentation resulted in the isolation of six new DMOA-related meroterpenoids with trivial names of brasilianoids A-F (1-6), together with preaustinoid D and preaustinoid A2. The structures were determined by extensive analyses of spectroscopic data, including the X-ray diffraction and the ECD data for configurational assignment. Brasilianoids A and F showed an unprecedented skeleton with a γ-lactone in ring A, while brasilianoids B-C featured a 7/6/6/5/5 pentacyclic ring system finding in nature for the first time. The biosynthetic relationship among the isolated compounds was postulated. Compound 1 significantly stimulated the expression of filaggrin and caspase-14 in HaCaT cells in dose-dependent manner, while compounds 2 and 3 showed moderate inhibition against NO production in LPS-induced RAW 264.7 macrophages.

| S-EPMC6072878 | biostudies-literature

New Andrastin-Type Meroterpenoids from the Marine-Derived Fungus Penicillium sp.

Project description:Three new andrastin-type meroterpenoids penimeroterpenoids A-C (1-3) together with two known analogs (4 and 5) were isolated from the cultures of the marine-derived Penicillium species (sp.). The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of 1-3 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed moderate cytotoxicity against A549, HCT116, and SW480 cell lines.

| S-EPMC8066695 | biostudies-literature

Antibacterial bisabolane-type sesquiterpenoids from the sponge-derived fungus Aspergillus sp.

Project description:Four new bisabolane-type sesquiterpenoids, aspergiterpenoid A (1), (-)-sydonol (2), (-)-sydonic acid (3), and (-)-5-(hydroxymethyl)-2-(2',6',6'-trimethyltetrahydro-2H- pyran-2-yl)phenol (4) together with one known fungal metabolite (5) were isolated from the fermentation broth of a marine-derived fungus Aspergillus sp., which was isolated from the sponge Xestospongia testudinaria collected from the South China Sea. Four of them (1-4) are optically active compounds. Their structures and absolute configurations were elucidated by using NMR spectroscopic techniques and mass spectrometric analysis, and by comparing their optical rotations with those related known analogues. Compounds 1-5 showed selective antibacterial activity against eight bacterial strains with the MIC (minimum inhibiting concentrations) values between 1.25 and 20.0 µM. The cytotoxic, antifouling, and acetylcholinesterase inhibitory activities of these compounds were also examined.

| S-EPMC3280534 | biostudies-literature

2,5-Diketopiperazines From a Sponge-Derived Fungus Aspergillus sclerotiorum.

Project description:Three new 2,5-diketopiperazines, speramide C (1), 3,21-epi-taichunamide F (2), and 2-epi-amoenamide C (3), along with four known analogs (4-7), were obtained from the sponge-derived fungus Aspergillus sclerotiorum GDST-2013-0501 collected from the South China Sea. The chemical structures of new compounds were elucidated by analyzing NMR and MS spectroscopy data, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations. Compound 1 represents the first prenylated indole alkaloid with an ethylene oxide ring at the isopentenyl side chain. Compound 4 displayed DNA topoisomerase I inhibitory activity and antibacterial activity against Staphylococcus epidermidis. The low cytotoxic or non-cytotoxic compound 4 displayed DNA topoisomerase I inhibitory activity, which could provide a starting point for the development of antitumor agents.

| S-EPMC9164150 | biostudies-literature

Antibacterial Cyclic Tripeptides from Antarctica-Sponge-Derived Fungus Aspergillus insulicola HDN151418.

Project description:Three new aspochracin-type cyclic tripeptides, sclerotiotides M-O (1-3), together with three known analogues, sclerotiotide L (4), sclerotiotide F (5), and sclerotiotide B (6), were obtained from the ethyl acetate extract of the fungus Aspergillus insulicola HDN151418, which was isolated from an unidentified Antarctica sponge. Spectroscopic and chemical approaches were used to elucidate their structures. The absolute configuration of the side chain in compound 4 was elucidated for the first time. Compounds 1 and 2 showed broad antimicrobial activity against a panel of pathogenic strains, including Bacillus cereus, Proteus species, Mycobacterium phlei, Bacillus subtilis, Vibrio parahemolyticus, Edwardsiella tarda, MRCNS, and MRSA, with MIC values ranging from 1.56 to 25.0 µM.

| S-EPMC7694092 | biostudies-literature

Isolation and Characterization of Two New Metabolites from the Sponge-Derived Fungus Aspergillus sp. LS34 by OSMAC Approach.

Project description:The application of an OSMAC (One Strain-Many Compounds) approach on the sponge-derived fungus Aspergillus sp. LS34, using two different media including solid rice medium and potato dextrose broth (PDB) resulted in the isolation and identification of two new compounds, named asperspin A (1) and asperther A (2) along with seven known compounds 3-9. Compounds 1-5 were detected in fungal extracts from rice medium, while compounds 6-9 were isolated from PDB medium. Their structures were unambiguously characterized by HRESIMS and NMR spectroscopic data. The growth inhibitory activity of these compounds against four pathogenic bacteria (Vibrio parahaemolyticus, Vibrio harveyi, Escherichia coli, and Staphylococcus aureus) were evaluated. All the compounds were also tested for their cytotoxicity against seven cancer cell lines, including CCRF-CEM, K562, BGC823, AGS, HCT-116, MDA-MB-453, and COR-L23. Among them, compound 9 showed strong activity against CCRF-CEM and K562 cells with IC50 values of 1.22 ± 0.05 µM and 10.58 ± 0.19 µM, respectively. Notably, compound 7 also showed pronounced activity against S. aureus with an MIC value of 3.54 µM.

| S-EPMC6562850 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data