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1.

001-es BibID:BIBFORM111396
035-os BibID:(WoS)000992551700001 (Scopus)85153802032
Első szerző:Eze, Peter M.
Cím:Two new metabolites from a marine-derived fungus Penicillium ochrochloron / Peter M. Eze, Yang Liu, Viktor E. Simons, Sherif S. Ebada, Tibor Kurtán, Sándor Balázs Király, Charles O. Esimone, Festus B.C. Okoye, Peter Proksch, Rainer Kalscheuer
Dátum:2023
ISSN:1874-3900 1876-7486
Megjegyzések:Co-culturing of fungi and bacteria proved to be an efficient tool for inducing the expression of silent biosynthetic gene clusters (BGCs). This study reports the isolation of a new meroterpenoid derivative, andrastin I (1), from a marine-derived fungus Penicillium ochrochloron. Co-cultivation of the fungus with Bacillus subtilis yielded another new natural product, a butyrolactone congener, ochrochloronic acid (2) and the known fungal metabolite striatisporolide A. Chemical structures of all isolated compounds were confirmed based on HRESIMS as well as, extensive 1D and 2D NMR spectral analyses. Absolute configuration of 1 was established by comparing the experimental ECD with those of known analogues. Results of this study highlight the potential of marine fungi as sources of new natural products and demonstrates the efficiency of fungal-bacterial co-cultivation as a promising tool to induce the immense biosynthetic capabilities of silent BGCs.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Fungi
Penicillium ochrochloron
Bacillus subtilis
Co-cultivation
Andrastin
Megjelenés:Phytochemistry Letters. - 55 (2023), p. 101-104. -
További szerzők:Liu, Yang Simons, Viktor Emanuel Ebada, Sherif Saeed Kurtán Tibor (1973-) (vegyész, angol szakfordító) Király Sándor Balázs (1991-) (vegyész) Esimone, Charles O. Okoye, Festus B.C. Proksch, Peter Kalscheuer, Rainer
Pályázati támogatás:K138672
OTKA
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2.

001-es BibID:BIBFORM070759
Első szerző:Li, Hong-Lei
Cím:Characterization of cladosporols from the marine algal-derived endophytic Fungus Cladosporium cladosporioides EN-399 and configurational revision of the previously reported Cladosporol derivatives / Hong-Lei Li, Xiao-Ming Li, Attila Mándi, Sándor Antus, Xin Li, Peng Zhang, Yang Liu, Tibor Kurtán, Bin-Gui Wang
Dátum:2017
ISSN:0022-3263
Megjegyzések:Four new cladosporol derivatives, cladosporols F?I (1?4), the known cladosporol C (5), and its new epimer, cladosporol J (6), were isolated and identified from the marine algal-derived endophytic fungus Cladosporium cladosporioides EN-399. Their structures were determined by detailed interpretation of NMR and MS data, and the absolute configurations were established on the basis of TDDFT-ECD and OR calculations. The configurational assignment of cladosporols F (1) and G (2) showed that the previously reported absolute configuration of cladosporol A and all the related cladosporols need to be revised from (4·R) to (4·S). Compounds 1?6 showed antibacterial activity against Escherichia coli, Micrococcus luteus, and Vibrio harveyi with MIC values ranging from 4 to 128 ?g/mL. Compound 3 showed significant cytotoxicity against A549, Huh7, and LM3 cell lines with IC50 values of 5.0, 1.0, and 4.1 ?M, respectively, and compound 5 showed activity against H446 cell line with IC50 value of 4.0 ?M.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Megjelenés:Journal of Organic Chemistry 82 : 19 (2017), p. 9946-9954. -
További szerzők:Li, Xiao-Ming Mándi Attila (1981-) (vegyész, német szakfordító) Antus Sándor (1944-2022) (vegyészmérnök) Li, Xin Zhang, Peng Liu, Yang Kurtán Tibor (1973-) (vegyész, angol szakfordító) Wang, Bin-Gui
Pályázati támogatás:NKFI K120181
Egyéb
NKFI K112951
Egyéb
NKFI PD121020
Egyéb
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3.

001-es BibID:BIBFORM072281
Első szerző:Liu, Yang
Cím:A novel 10-membered macrocyclic lactone from the mangrove-derived endophytic fungus Annulohypoxylon sp. / Yang Liu, Tibor Kurtán, Attila Mándi, Horst Weber, Changyun Wang, Rudolf Hartmann, Wenhan Lin, Georgios Daletos, Peter Proksch
Dátum:2018
ISSN:0040-4039
Megjegyzések:A novel 10-membered macrolactone, hypoxylide ( 1), was isolated from the endophytic fungus Annulohypoxylon sp. that was obtained from the Mangrove plant Rhizophora racemosa. The structure and absolute configuration of 1 were unambiguously elucidated by comprehensive 1D and 2D NMR, as well as by HRESIMS and ECD spectroscopic analyses. Hypoxylide (1) features an unprecedented polyketide skeleton comprised of a trihydroxynaphthalene-dione moiety fused to a decalactone ring. A plausible biosynthetic pathway of this novel metabolite is proposed.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Macrolactone
Natural product
Annulohypoxylon sp.
Mangrove
Endophytic fungus
Megjelenés:Tetrahedron Letters 59 : 7 (2018), p. 632-636. -
További szerzők:Kurtán Tibor (1973-) (vegyész, angol szakfordító) Mándi Attila (1981-) (vegyész, német szakfordító) Weber, Horst Wang, Chang Yun Hartmann, Rudolf Lin, Wen Han Daletos, Georgios Proksch, Peter
Pályázati támogatás:NKFI K120181
Egyéb
NKFI PD 121020
Egyéb
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4.

001-es BibID:BIBFORM067037
Első szerző:Liu, Yang
Cím:Daldinone derivatives from the mangrove-derived endophytic fungus Annulohypoxylon sp. / Yang Liu, Fabian Stuhldreier, Tibor Kurtán, Attila Mándi, Sathishkumar Arumugam, Wenhan Lin, Björn Stork, Sebastian Wesselborg, Horst Weber, Birgit Henrich, Georgios Daletos, Peter Proksch
Dátum:2017
ISSN:2046-2069
Megjegyzések:Two new benzo[j]fluoranthene metabolites, daldinones H, J (1 and 3), and the likewise undescribed artefact, daldinone I (2), along with six known compounds (4-9) were isolated from the endophytic fungus Annulohypoxylon sp. that was obtained from the Mangrove plant Rhizophora racemosa collected in Cameroon. The structures of the new compounds were elucidated by 1D and 2D NMR as well as by HRESIMS and ECD spectra analysis. Co-cultivation of this fungus with the actinomycetes Streptomyces lividans or with Streptomyces coelicolor resulted in an up to 38-fold increase of 1-hydroxy-8-methoxynaphthalene (9), while no significant induction was detected when the fungus was co-cultivated either with Bacillus subtilis or with Bacillus cereus. Compound 2 exhibited strong to moderate cytotoxicity against Ramos and Jurkat J16 cells with IC50 values of 6.6 and 14.1 ?M, respectively. Mechanistic studies indicated that compound 2 induces apoptotic cell death caused by induction of intrinsic apoptosis. Moreover, 2 potently blocks autophagy, a potential pro-survival pathway for cancer cells. Feeding experiments with 1,8-dihydroxynaphthalene (DHN) led to an enhanced accumulation of daldinone B (6), which supported the proposed biogenetic pathway.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Megjelenés:RSC Advances. - 7 : 9 (2017), p. 5381-5393. -
További szerzők:Stuhldreier, Fabian Kurtán Tibor (1973-) (vegyész, angol szakfordító) Mándi Attila (1981-) (vegyész, német szakfordító) Arumugam, Sathishkumar Lin, Wen Han Stork, Björn Wesselborg, Sebastian Weber, Horst Henrich, Birgit Daletos, Georgios Proksch, Peter
Pályázati támogatás:K105871
OTKA
NIIFI 10038
Egyéb
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5.

001-es BibID:BIBFORM065737
Első szerző:Liu, Yang
Cím:Cladosporinone, a new viriditoxin derivative from the hypersaline lake derived fungus Cladosporium cladosporioides / Yang Liu, Tibor Kurtán, Chang Yun Wang, Wen Han Lin, Raha Orfali, Werner E. G. Müller, Georgios Daletos, Peter Proksch
Dátum:2016
ISSN:0021-8820
Megjegyzések:A new cytotoxic viriditoxin derivative, cladosporinone (1), along with the known viriditoxin (2) and two viriditoxin derivatives (3 and 4) were obtained from the fungus Cladosporium cladosporioides isolated from the sediment of a hypersaline lake in Egypt. The structure of the new compound (1) was determined by 1D and 2D NMR measurements as well as by high-resolution ESIMS and electronic circular dichroism spectroscopy. All isolated compounds were studied for their cytotoxicity against the murine lymphoma cell line L5187Y and for their antibiotic activity against several pathogenic bacteria. Viriditoxin (2) was the most active compound in both bioassays. Compound 1 also exhibited strong cytotoxicity against the murine lymphoma cell line L5187Y with an IC50 value of 0.88 ?M, whereas its antibiotic activity was weak.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Megjelenés:Journal of Antibiotics 69 : 9 (2016), p. 702-706. -
További szerzők:Kurtán Tibor (1973-) (vegyész, angol szakfordító) Yun Wang, Chang Han Lin, Wen Orfali, Raha Müller, Werner E. G. Daletos, Georgios Proksch, Peter
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6.

001-es BibID:BIBFORM058851
Első szerző:Liu, Yang
Cím:Tetrahydroanthraquinone Derivatives from the Endophytic Fungus Stemphylium globuliferm / Yang Liu, Andreas Marmann, Mohamed S. Abdel-Aziz, Chang Yun Wang, Werner E. G. Müller, Wen Han Lin, Attila Mándi, Tibor Kurtán, Georgios Daletos, Peter Proksch
Dátum:2015
ISSN:1434-193X 1099-0690
Megjegyzések:Four new tetrahydroanthraquinone derivatives, namely, dihydroaltersolanol B (1), dihydroaltersolanol C (2), and the atropisomers acetylalterporriol D (3) and acetylalterporriol E (4), were obtained from the endophytic fungus Stemphylium globuliferum, which was isolated from Juncus acutus growing in Egypt. The structures of the new compounds were unambiguously elucidated on the basis of one- and two-dimensional NMR spectroscopy, as well as by high-resolution mass spectrometry and electronic circular dichroism (ECD) spectroscopy. In addition, seven known anthraquinone derivatives 5?11 were isolated and identified on the basis of their spectral characteristics and by comparison with literature data. Compounds 2, 4?7, 9, and 11 showed strong cytotoxicity against the murine lymphoma cell line L5178Y with IC50 values ranging from 1.25 to 10.4 ?M. Compounds 1?4 were also tested for their antibacterial activity against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Only 2 exhibited moderate growth inhibition against S. aureus with a minimum inhibitory concentration (MIC) of 49.7 ?M.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Natural products
Endophytic fungi
Quinones
Cytotoxicity
Antibacterial activity
Atropisomerism
Megjelenés:European Journal of Organic Chemistry. - 2015 : 12 (2015), p. 2646-2653. -
További szerzők:Marmann, Andreas Abdel-Aziz, Mohamed S. Wang, Chang Yun Müller, Werner E. G. Lin, Wen Han Mándi Attila (1981-) (vegyész, német szakfordító) Kurtán Tibor (1973-) (vegyész, angol szakfordító) Daletos, Georgios Proksch, Peter
Pályázati támogatás:K105871
OTKA
NIIFI 10038
Egyéb
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7.

001-es BibID:BIBFORM058799
Első szerző:Liu, Yang
Cím:Peniciadametizine A, a Dithiodiketopiperazine with a Unique Spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] Skeleton, and a Related Analogue, Peniciadametizine B, from the Marine Sponge-Derived Fungus Penicillium adametzioides / Yang Liu, Attila Mándi, Xiao-Ming Li, Ling-Hong Meng, Tibor Kurtán, Bin-Gui Wang
Dátum:2015
ISSN:1660-3397
Megjegyzések:Peniciadametizine A (1); a new dithiodiketopiperazine derivative possessing a uniquespiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine] skeleton, together with a highly oxygenated newanalogue, peniciadametizine B (2); as well as two known compounds, brasiliamide A (3); andviridicatumtoxin (4), were isolated and identified from Penicillium adametzioides AS-53, afungus obtained from an unidentified marine sponge. The unambiguous assignment of therelative and absolute configuration for the spiro center C-2 of compound 1 was solved bythe combination of NMR and ECD measurements with Density-Functional Theory (DFT)conformational analysis and Time-Dependent Density-Functional Theory-Electronic CircularDichroism (TDDFT-ECD) calculations. The spiro[furan-2,7'-pyrazino[1,2-b][1,2]oxazine]skeleton of 1 has not been reported yet among natural products and the biosynthetic pathwayfor 1 and 2 was discussed. Compounds 1 and 2 showed inhibitory activity against thepathogenic fungus Alternaria brassicae.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
marine sponge
endophytic fungus
Penicillium adametzioides
secondary metabolites
antifungal activity
Megjelenés:Marine Drugs. - 13 : 6 (2015), p. 3640-3652. -
További szerzők:Mándi Attila (1981-) (vegyész, német szakfordító) Li, Xiao-Ming Meng, Ling-Hong Kurtán Tibor (1973-) (vegyész, angol szakfordító) Wang, Bin-Gui
Pályázati támogatás:K105871
OTKA
NIIFI 10038
Egyéb
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8.

001-es BibID:BIBFORM064958
Első szerző:Meng, Ling-Hong
Cím:Isolation, Stereochemical Study, and Antioxidant Activity of Benzofuranone Derivatives from a Mangrove-derived Fungus Eurotium rubrum MA-150 / Ling-Hong Meng, Attila Mándi, Xiao-Ming Li, Yang Liu, Tibor Kurtán, Bin-Gui Wang
Dátum:2016
ISSN:0899-0042
Megjegyzések:Enantiomers of a 2-benzofuran-1(3H)-one derivative [(?)-1 and (+)-1] and four known analogs (2-5) were isolated and identified from the culture extract of Eurotium rubrum MA?150, a fungus obtained from the mangrove-derived rizospheric soil. Their structures were established by detailed interpretation of nuclear magnetic resonance (NMR) data and the structure of (?)-1 was confirmed by single-crystal X-ray diffraction analysis. The absolute configuration of the enantiomers (?)-1 and (+)-1 was determined by means of online high-performance liquid chromatography - electronic circular dichroism (HPLC-ECD) measurements and time-dependent Density Functional Theory - electronic circular dichroism (TDDFT-ECD) calculations. Compounds (?)-1 as well as 2 and 3 exhibited potent DPPH radical scavenging activities with IC50 values of 1.23, 2.26, and 3.99 ?g/mL, respectively.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
marine-derived fungus
benzofuran-1(3H)-one
HPLC-ECD
TDDFT calculations
DPPH
radical scavenging activity
Megjelenés:Chirality. - 28 : 8 (2016), p. 581-584. -
További szerzők:Mándi Attila (1981-) (vegyész, német szakfordító) Li, Xiao-Ming Liu, Yang Kurtán Tibor (1973-) (vegyész, angol szakfordító) Wang, Bin-Gui
Pályázati támogatás:K105871
OTKA
BAROSS REG_EA_09-1-2009-0028 (LCMS_TAN)
Egyéb
TÁMOP-4.2.2.C-11/1/KONV-2012-0010
TÁMOP
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9.

001-es BibID:BIBFORM105627
035-os BibID:(WoS)000791431400029 (Scopus)85128793848
Első szerző:Wang, Lei
Cím:Discovery and Biosynthesis of Antimicrobial Phenethylamine Alkaloids from the Marine Flavobacterium Tenacibaculum discolor sv11 / Lei Wang, Virginia Linares-Otoya, Yang Liu, Ute Mettal, Michael Marner, Lizbeth Armas-Mantilla, Sabine Willbold, Tibor Kurtán, Luis Linares-Otoya, Till F. Schäberle
Dátum:2022
ISSN:0163-3864 1520-6025
Megjegyzések:The bacterial genus Tenacibaculum has been associated with various ecological roles in marine environments. Members of this genus can act, for example, as pathogens, predators, or episymbionts. However, natural products produced by these bacteria are still unknown. In the present work, we investigated a Tenacibaculum strain for the production of antimicrobial metabolites. Six new phenethylamine (PEA)-containing alkaloids, discolins A and B (1 and 2), dispyridine (3), dispyrrolopyridine A and B (4 and 5), and dispyrrole (6), were isolated from media produced by the predatory bacterium Tenacibaculum discolor sv11. Chemical structures were elucidated by analysis of spectroscopic data. Alkaloids 4 and 5 exhibited strong activity against Gram-positive Bacillus subtilis DSM10, Mycobacterium smegmatis ATCC607, Listeria monocytogenes DSM20600, and Staphylococcus aureus ATCC25923, with minimum inhibitory concentration (MIC) values ranging from 0.5 to 4 mu g/mL, and moderate activity against Candida albicans FH2173 and Aspergillus flavus ATCC9170. Compound 6 displayed moderate antibacterial activities against Gram-positive bacteria. Dispyrrolopyridine A (4) was active against efflux pump deficient Escherichia coli ATCC25922 Delta tolC, with an MIC value of 8 mu g/mL, as well as against Caenorhabditis elegans N2 with an MIC value of 32 mu g/mL. Other compounds were inactive against these microorganisms. The biosynthetic route toward discolins A and B (1 and 2) was investigated using in vivo and in vitro experiments. It comprises an enzymatic decarboxylation of phenylalanine to PEA catalyzed by DisA, followed by a nonenzymatic condensation to form the central imidazolium ring. This spontaneous formation of the imidazolium core was verified by means of a synthetic one-pot reaction using the respective building blocks. Six additional strains belonging to three Tenacibaculum species were able to produce discolins, and several DisA analogues were identified in various marine flavobacterial genera, suggesting the widespread presence of PEA-derived compounds in marine ecosystems.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
folyóiratcikk
Megjelenés:Journal of Natural Products. - 85 : 4 (2022), p. 1039-1051. -
További szerzők:Linares-Otoya, Virginia Liu, Yang Mettal, Ute Marner, Michael Armas-Mantilla, Lizbeth Willbold, Sabine Kurtán Tibor (1973-) (vegyész, angol szakfordító) Linares-Otoya, Luis Schäberle, Till F.
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10.

001-es BibID:BIBFORM054606
Első szerző:Zhang, Peng
Cím:Brocaeloids A-C, 4-Oxoquinoline and Indole Alkaloids with C-2 Reversed Prenylation from the Mangrove-Derived Endophytic Fungus Penicillium brocae / Peng Zhang, Ling-Hong Meng, Attila Mándi, Tibor Kurtán, Xiao-Ming Li, Yang Liu, Xin Li, Chun-Shun Li, Bin-Gui Wang
Dátum:2014
ISSN:1434-193X 1434-193X 1099-0690
Megjegyzések:Three new alkaloids, brocaeloids A-C (1-3), containing C-2 reversed prenylation, were isolated from cultures ofPenicillium brocae MA-192, an endophytic fungus obtained from the fresh leaves of the marine mangrove plantAvicennia marina. Their structures were determined on the basis of 1D and 2D NMR spectroscopy as well as by high-resolution mass spectrometry. The absolute configuration of brocaeloid A (1) was established by gas-phase and solution conformational analysis and TDDFT-ECD calculations, which revealed that the fused hetero-ring adopted M-helicity conformation with axial orientation of the C-2 and C-3 substituents. The correct assignment of the hetero-ring conformation was found to be crucial in determining the relative and absolute configuration. Based on ECD calculations, the helicity of the 2,3-dihydroquinoline-4(1H)-one chromophore was correlated with the characteristic ECD transitions, and the resultant helicity rule was found to coincide with that of the chroman-4-one chromophore. X-ray single-crystal analysis of1by Cu-K?radiation also confirmed the result of the stereochemical analysis obtained from ECD calculations. Brocaeloid B (2) showed lethality against brine shrimp (Artemia salina) with an LD50 value of 36.7?M.
Tárgyszavak:Természettudományok Kémiai tudományok idegen nyelvű folyóiratközlemény külföldi lapban
Natural products
Alkaloids
Circular dichroism
Density functional calculations
Megjelenés:European Journal of Organic Chemistry. - 2014 : 19 (2014), p. 4029-4036. -
További szerzők:Meng, Ling-Hong Mándi Attila (1981-) (vegyész, német szakfordító) Kurtán Tibor (1973-) (vegyész, angol szakfordító) Li, Xiao-Ming Liu, Yang Li, Xin Li, Chun-Shun Wang, Bin-Gui
Pályázati támogatás:K105871
OTKA
NIIFI 10038
Egyéb
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