Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Polyhydroxy p-Terphenyls from a Mangrove Endophytic Fungus Aspergillus candidus LDJ-5.

ABSTRACT: Six undescribed polyhydroxy p-terphenyls, namely asperterphenyllins A-F, were isolated from an endophytic fungus Aspergillus candidus LDJ-5. Their structures were determined by NMR and MS data. Differing from the previously reported p-terphenyls, asperterphenyllin A represents the first p-terphenyl dimer connected by a C-C bond. Asperterphenyllin A displayed anti-influenza virus A (H1N1) activity and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC₅₀ values of 53 ?M and 21 ?M, respectively. The anti-influenza virus A (H1N1) activity and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity of p-terphenyls are reported for the first time. Asperterphenyllin G exhibited cytotoxicity against nine cell lines with IC₅₀ values ranging from 0.4 to 1.7 ?M. Asperterphenyllin C showed antimicrobial activity against Proteus species with a MIC value of 19 ?g/mL.

SUBMITTER: Zhou G

PROVIDER: S-EPMC7912881 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Polyhydroxy p-Terphenyls from a Mangrove Endophytic Fungus Aspergillus candidus LDJ-5.

Zhou Guoliang G Zhang Xiaomin X Shah Mudassir M Che Qian Q Zhang Guojian G Gu Qianqun Q Zhu Tianjiao T Li Dehai D

Marine drugs 20210202 2

Six undescribed polyhydroxy p-terphenyls, namely asperterphenyllins A-F, were isolated from an endophytic fungus Aspergillus candidus LDJ-5. Their structures were determined by NMR and MS data. Differing from the previously reported p-terphenyls, asperterphenyllin A represents the first p-terphenyl dimer connected by a C-C bond. Asperterphenyllin A displayed anti-influenza virus A (H1N1) activity and protein tyrosine phosphatase 1B (PTP1B) inhibitory activity with IC< ...[more]

PMID: 33540563

Similar Datasets

Bioactive Metabolites from Mangrove Endophytic Fungus Aspergillus sp. 16-5B.

Project description:Chemical investigation of the endophytic fungus Aspergillus sp. 16-5B cultured on Czapek's medium led to the isolation of four new metabolites, aspergifuranone (1), isocoumarin derivatives (±) 2 and (±) 3, and (R)-3-demethylpurpurester A (4), together with the known purpurester B (5) and pestaphthalides A (6). Their structures were determined by analysis of 1D and 2D NMR spectroscopic data. The absolute configuration of Compound 1 was determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra, and that of Compound 4 was revealed by comparing its optical rotation data and CD with those of the literature. The structure of Compound 6 was further confirmed by single-crystal X-ray diffraction experiment using CuKα radiation. All isolated compounds were evaluated for their α-glucosidase inhibitory activities, and Compound 1 showed significant inhibitory activity with IC50 value of 9.05 ± 0.60 μM. Kinetic analysis showed that Compound 1 was a noncompetitive inhibitor of α-glucosidase. Compounds 2 and 6 exhibited moderate inhibitory activities.

| S-EPMC4446620 | biostudies-literature

Acetylcholinesterase Inhibitory Meroterpenoid from a Mangrove Endophytic Fungus Aspergillus sp. 16-5c.

Project description:One new meroterpenoid, named 2-hydroacetoxydehydroaustin (1), together with nine known meroterpenoids, 11-acetoxyisoaustinone (2), isoaustinol (3), austin (4), austinol (5), acetoxydehydroaustin (6), dehydroaustin (7), dehydroaustinol (8), preaustinoid A2 (9), and 1,2-dihydro-acetoxydehydroaustin B (10), were isolated from the mangrove endophytic fungus, Aspergillus sp. 16-5c. These structures were characterized by spectroscopic analysis, further the absolute configurations of stereogenic carbons for Compounds 1, 3, 4, 6, 7, 8, 9, and 10 were determined by single crystal X-ray diffraction analysis using Cu Kα radiation. Moreover, the absolute configurations of stereogenic carbons for Known Compounds 3, 7, 8, and 9 are identified here for the first time. Compounds 3, 7, and 8 showed acetylcholinesterase (AchE) inhibitory activity with IC50 values of 2.50, 0.40, and 3.00 μM, respectively.

| S-EPMC6154586 | biostudies-literature

New Benzofuranoids and Phenylpropanoids from the Mangrove Endophytic Fungus, Aspergillus sp. ZJ-68.

Project description:Three new benzofuranoids, asperfuranoids A-C (1-3), two new phenylpropanoid derivatives (6 and 7), and nine known analogues (4, 5, and 8-14) were isolated from the liquid substrate fermentation cultures of the mangrove endopytic fungus Aspergillus sp. ZJ-68. The structures of the new compounds were determined by extensive spectroscopic data interpretation. The absolute configurations of 1-3 were assigned via the combination of Mosher's method, and experimental and calculated electronic circular dichroism (ECD) data. Compounds 4 and 5 were a pair of enantiomers and their absolute configurations were established for the first time on the basis of their ECD spectra aided with ECD calculations. All isolated compounds (1-14) were evaluated for their enzyme inhibitory activity against ?-glucosidase and antibacterial activities against four pathogenic bacteria (Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa). Among them, compound 6 exhibited potent inhibitory activity against ?-glucosidase in a standard in vitro assay, with an IC50 value of 12.4 ?M, while compounds 8 and 11 showed activities against S. aureus, E. coli, and B. subtilis, with MIC values in the range of 4.15 to 12.5 ?g/mL.

| S-EPMC6723808 | biostudies-literature

Identification and Antifungal Activity of Compounds from the Mangrove Endophytic Fungus Aspergillus clavatus R7.

Project description:Two new coumarin derivatives, 4,4'-dimethoxy-5,5'-dimethyl-7,7'-oxydicoumarin (1), 7-(γ,γ-dimethylallyloxy)-5-methoxy-4-methylcoumarin (2), a new chromone derivative, (S)-5-hydroxy-2,6-dimethyl-4H-furo[3,4-g]benzopyran-4,8(6H)-dione (5), and a new sterone derivative, 24-hydroxylergosta-4,6,8(14),22-tetraen-3-one (6), along with two known bicoumarins, kotanin (3) and orlandin (4), were isolated from an endophytic fungus Aspergillusclavatus (collection No. R7), isolated from the root of Myoporum bontioides collected from Leizhou Peninsula, China. Their structures were elucidated using 1D- and 2D- NMR spectroscopy, and HRESIMS. The absolute configuration of compound 5 was determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. Compound 6 significantly inhibited the plant pathogenic fungi Fusarium oxysporum, Colletotrichum musae and Penicillium italicum, compound 5 significantly inhibited Colletotrichum musae, and compounds 1, 3 and 4 greatly inhibited Fusarium oxysporum, showing the antifungal activities higher than those of the positive control, triadimefon.

| S-EPMC5577613 | biostudies-literature

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242.

Project description:The chemical investigation of the mangrove endophytic fungus Aspergillus sp. 085242 afforded eight isocoumarin derivatives 1-8 and one isoquinoline 9. Asperisocoumarins A and B (1 and 2) were new furoisocoumarins, and asperisocoumarins E and F (5 and 6) were new isocoumarins. Their structures were established by analysis of their spectroscopic data and the absolute configuration of compound 2 was unambiguously determined by X-ray structure analysis and ECD calculation. Moreover, the absolute configurations of compounds 3-5 were assigned by comparison of their ECD spectra with isocoumarins described in the literature. Asperisocoumarins C and D (3 and 4) were fully characterized spectroscopically and isolated from a natural source for the first time. Asperisocoumarins A-D (1-4) related to the class of furo[3,2-h]isocoumarins are rarely occurring in natural sources. Compounds 2, 5, and 6 showed moderate α-glucosidase inhibitory activity with IC50 of 87.8, 52.3, and 95.6 μM, respectively. In addition, compounds 1 and 3 exhibited weak radical scavenging activity with EC50 values of 125 and 138 μM, respectively.

| S-EPMC5082600 | biostudies-literature

Asperlones A and B, dinaphthalenone derivatives from a mangrove endophytic fungus Aspergillus sp. 16-5C.

Project description:Racemic dinaphthalenone derivatives, (±)-asperlone A (1) and (±)-asperlone B (2), and two new azaphilones, 6'-hydroxy-(R)-mitorubrinic acid (3) and purpurquinone D (4), along with four known compounds, (-)-mitorubrinic acid (5), (-)-mitorubrin (6), purpurquinone A (7) and orsellinic acid (8), were isolated from the cultures of Aspergillus sp. 16-5C. The structures were elucidated using comprehensive spectroscopic methods, including 1D and 2D NMR spectra and the structures of 1 further confirmed by single-crystal X-ray diffraction analysis, while the absolute configuration of 3 and 4 were determined by comparing their optical rotation and CD with those of the literature, respectively. Compounds 1, 2 and 6 exhibited potent inhibitory effects against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with IC50 values of 4.24 ± 0.41, 4.32 ± 0.60 and 3.99 ± 0.34 μM, respectively.

| S-EPMC4306942 | biostudies-literature

Identification and Bioactivity of Compounds from the Mangrove Endophytic Fungus Alternaria sp.

Project description:Racemic new cyclohexenone and cyclopentenone derivatives, (±)-(4R*,5S*,6S*)-3-amino-4,5,6-trihydroxy-2-methoxy-5-methyl-2-cyclohexen-1-one (1) and (±)-(4S*,5S*)-2,4,5-trihydroxy-3-methoxy-4-methoxycarbonyl-5-methyl-2-cyclopenten-1-one (2), and two new xanthone derivatives 4-chloro-1,5-dihydroxy-3-hydroxymethyl-6-methoxycarbonyl-xanthen-9-one (3) and 2,8-dimethoxy-1,6-dimethoxycarbonyl-xanthen-9-one (4), along with one known compound, fischexanthone (5), were isolated from the culture of the mangrove endophytic fungus Alternaria sp. R6. The structures of these compounds were elucidated by analysis of their MS (Mass), one and two dimensional NMR (nuclear magnetic resonance) spectroscopic data. Compounds 1 and 2 exhibited potent ABTS [2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid)] scavenging activities with EC50 values of 8.19 ± 0.15 and 16.09 ± 0.01 ?M, respectively. In comparison to Triadimefon, compounds 2 and 3 exhibited inhibitory activities against Fusarium graminearum with minimal inhibitory concentration (MIC) values of 215.52 and 107.14 ?M, respectively, and compound 3 exhibited antifungal activity against Calletotrichum musae with MIC value of 214.29 ?M.

| S-EPMC4515629 | biostudies-other

Secondary metabolites of a mangrove endophytic fungus Aspergillus terreus (No. GX7-3B) from the South China Sea.

Project description:The mangrove endophytic fungus Aspergillus terreus (No. GX7-3B) was cultivated in potato dextrose liquid medium, and one rare thiophene compound (1), together with anhydrojavanicin (2), 8-O-methylbostrycoidin (3), 8-O-methyljavanicin (4), botryosphaerone D (5), 6-ethyl-5-hydroxy-3,7-dimethoxynaphthoquinone (6), 3?,5?-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one (7), 3?,5?,14?-trihydroxy-(22E,24R)-ergosta-7, 22-dien-6-one (8), NGA0187 (9) and beauvericin (10), were isolated. Their structures were elucidated by analysis of spectroscopic data. This is the first report of a natural origin for compound 6. Moreover, compounds 3, 4, 5, 7, 8 and 10 were obtained from marine microorganism for the first time. In the bioactive assays in vitro, compounds 2, 3, 9 and 10 displayed remarkable inhibiting actions against ?-acetylcholinesterase (AChE) with IC50 values 2.01, 6.71, 1.89, and 3.09 ?M, respectively. Furthermore, in the cytotoxicity assays, compounds 7 and 10 exhibited strong or moderate cytotoxic activities against MCF-7, A549, Hela and KB cell lines with IC50 values 4.98 and 2.02 (MCF-7), 1.95 and 0.82 (A549), 0.68 and 1.14 (Hela), and 1.50 and 1.10 ?M (KB), respectively; compound 8 had weak inhibitory activities against these tumor cell lines; compounds 1, 2, 3, 4, 5, 6 and 9 exhibited no inhibitory activities against them.

| S-EPMC3736441 | biostudies-literature

Two Antimicrobial Heterodimeric Tetrahydroxanthones with a 7,7'-Linkage from Mangrove Endophytic Fungus Aspergillus flavus QQYZ.

Project description:Mangrove endophytic fungi represent significant and sustainable sources of novel metabolites with unique structures and excellent biological activities, attracting extensive chemical investigations. In this research, two novel heterodimeric tetrahydroxanthones, aflaxanthones A (1) and B (2), dimerized via an unprecedented 7,7'-linkage, a sp3-sp3 dimeric manner, were isolated from the mangrove endophytic fungus Aspergillus flavus QQYZ. Their structures were elucidated through high resolution electrospray ionization mass spectroscopy (HRESIMS) and nuclear magnetic resonance (NMR) spectroscopy, the absolute configurations of them were determined by a single-crystal X-ray diffraction combined with calculated electronic circular dichroism (ECD) spectra and a 1D potential energy scan. These compounds were evaluated for antifungal activities in vitro and exhibited broad-spectrum and potential antifungal activities against several pathogenic fungi with minimum inhibitory concentration (MIC) values in the range of 3.13-50 μM. They also performed moderate antibacterial activities against several bacteria with MIC values in the range of 12.5-25 μM. This research enriched the resources of lead compounds and templates for marine-derived antimicrobial drugs.

| S-EPMC9103106 | biostudies-literature

Isolation, Structural Characterization and Antidiabetic Activity of New Diketopiperazine Alkaloids from Mangrove Endophytic Fungus Aspergillus sp. 16-5c.

Project description:Six new DIKETOPIPERAZINE alkaloids aspergiamides A-F (1-6), together with ten known alkaloids (7-16), were isolated from the mangrove endophytic fungus Aspergillus sp. 16-5c. The structures of the new compounds were elucidated based on 1D/2D NMR spectroscopic and HR-ESIMS data analyses. The absolute configurations of aspergiamides A-F were established based on the experimental and calculated ECD data. All the compounds were evaluated for the antidiabetic activity against α-glucosidase and PTP1B enzyme. The bioassay results disclosed compounds 1 and 9 exhibited significant α-glucosidase inhibitory with IC50 values of 18.2 and 7.6 μM, respectively; compounds 3, 10, 11, and 15 exhibited moderate α-glucosidase inhibition with IC50 values ranging from 40.7 to 83.9 μM; while no compounds showed obvious PTP1B enzyme inhibition activity.

| S-EPMC8304462 | biostudies-literature