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39 results on '"Schrey, Hedda"'

5. Omnipolyphilins A and B: Chlorinated Cyclotetrapeptides and Naphtho-α-pyranones from the Plant Nematode-Derived Fungus Polyphilus sieberi

Author

Wennrich, Jan-Peer, primary, Ebada, Sherif S., additional, Sepanian, Ellen, additional, Holzenkamp, Caren, additional, Khalid, Syeda J., additional, Schrey, Hedda, additional, Maier, Wolfgang, additional, Mándi, Attila, additional, Kurtán, Tibor, additional, Ashrafi, Samad, additional, and Stadler, Marc, additional

Published
2024
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22. Synthesis and Bioactivity of Ancorinoside B, a Marine Diglycosyl Tetramic Acid

Author

Soliga, Kevin J., Bär, Sofia I., Oberhuber, Natalie, Zeng, Haoxuan, Schrey, Hedda, Schobert, Rainer, and HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.

Subjects
ancorinoside B, Aquatic Organisms, Staphylococcus aureus, QH301-705.5, Microbial Sensitivity Tests, MMP inhibitor, Pyrrolidinones, Article, Anti-Bacterial Agents, Porifera, glycosyl tetramic acid, Animals, marine sponge metabolite, Biology (General), microbial biofilm inhibitor
Abstract

The sponge metabolite ancorinoside B was prepared for the first time in 16 steps and 4% yield. It features a β-d-galactopyranosyl-(1→4)-β-d-glucuronic acid tethered to a d-aspartic acid-derived tetramic acid. Key steps were the synthesis of a fully protected d-lactose derived thioglycoside, its attachment to a C20-aldehyde spacer, functionalization of the latter with a terminal N-(β-ketoacyl)-d-aspartate, and a basic Dieckmann cyclization to close the pyrrolidin-2,4-dione ring with concomitant global deprotection. Ancorinoside B exhibited multiple biological effects of medicinal interest. It inhibited the secretion of the cancer metastasis-relevant matrix metalloproteinases MMP-2 and MMP-9, and also the growth of Staphylococcus aureus biofilms by ca 87% when applied at concentrations as low as 0.5 µg/mL. This concentration is far below its MIC of ca 67 µg/mL and thus unlikely to induce bacterial resistance. It also led to a 67% dispersion of preformed S. aureus biofilms when applied at a concentration of ca 2 µg/mL. Ancorinoside B might thus be an interesting candidate for the control of the general hospital, catheter, or joint protheses infections.

Published
2021

24. Total Synthesis via Biomimetic Late-Stage Heterocyclization: Assignment of the Relative Configuration and Biological Evaluation of the Nitraria Alkaloid (±)-Nitrabirine

Author

Kagho, Mervic D., primary, Hintersatz, Helen, additional, Ihle, Andreas, additional, Zeng, Haoxuan, additional, Schrey, Hedda, additional, Colisi, Wera, additional, Klahn, Philipp, additional, Stadler, Marc, additional, Bruhn, Clemens, additional, Rüffer, Tobias, additional, Lang, Heinrich, additional, and Banert, Klaus, additional

Published
2021
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26. Total Synthesis via Biomimetic Late-stage Heterocyclization, Assignment of the Relative Configuration and Biological Evalu-ation of the Nitraria Alkaloid (±)-Nitrabirine

Author

Kagho, Mervic Dongock, primary, Hintersatz, Helen, additional, Ihle, Andreas, additional, Zeng, Haoxuan, additional, Schrey, Hedda, additional, Colisi, Wera, additional, Klahn, Philipp, additional, Stadler, Marc, additional, Bruhns, Clemens, additional, Rüffer, Tobias, additional, Lang, Heinrich, additional, and Banert, Klaus, additional

Published
2021
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27. Dual Agents : Fungal Macrocidins and Synthetic Analogues with Herbicidal and Antibiofilm Activities

Author

Treiber, Laura, Pezolt, Christine, Zeng, Haoxuan, Schrey, Hedda, Jungwirth, Stefan, Shekhar, Aditya, Stadler, Marc, Bilitewski, Ursula, Erb-Brinkmann, Maike, and Schobert, Rainer

Subjects
polycyclic tetramate macrolactams, macrocidin, 3-acyltetramic acids, Therapeutics. Pharmacology, RM1-950, biofilms, Article, antibiotics
Abstract

Eight analogues of the bioherbicides macrocidin A (1) and Z (2) with structural variance in the size of the macrocycle, its para- or meta-cyclophane character, and its functional groups were synthesized on two modular routes and tested for herbicidal, antibiotic, and antibiofilm activities. Apart from the lead compounds 1 and 2, the structurally simplified dihydromacrocidin Z (3) and normacrocidin Z (4) showed high herbicidal activity in either thistles, dandelions or in both. The derivatives 2, 3, and dibromide 9 also inhibited the growth of Staphylococcus aureus biofilms by ca 70% when applied at subtoxic concentrations as low as ca 20 µM, which are unlikely to induce bacterial resistance. They also led to the dispersion of preformed biofilms of S. aureus, exceeding a similar effect by microporenic acid A, a known biofilm inhibitor. Compounds 3 and 9 showed no noticeable cytotoxicity against human cancer and endothelial cells at concentrations below 50 µM, making them conceivable candidates for application as anti-biofilm agents in a medicinal context.

Published
2021
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28. Macrooxazoles A-D, New 2,5-Disubstituted Oxazole-4-Carboxylic Acid Derivatives from the Plant Pathogenic Fungus

Author

Matio Kemkuignou, Blondelle, Treiber, Laura, Zeng, Haoxuan, Schrey, Hedda, Schobert, Rainer, Stadler, Marc, and HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.

Subjects
macrocidin Z synthesis, oxazole derivatives, structure elucidation, anti-biofilm, isolation, Phoma macrostoma
Abstract

In our ongoing search for new bioactive fungal metabolites, four previously undescribed oxazole carboxylic acid derivatives (1-4) for which we proposed the trivial names macrooxazoles A-D together with two known tetramic acids (5-6) were isolated from the plant pathogenic fungus Phoma macrostoma. Their structures were elucidated based on high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy. The hitherto unclear structure of macrocidin Z (6) was also confirmed by its first total synthesis. The isolated compounds were evaluated for their antimicrobial activities against a panel of bacteria and fungi. Cytotoxic and anti-biofilm activities of the isolates are also reported herein. The new compound 3 exhibited weak-to-moderate antimicrobial activity as well as the known macrocidins 5 and 6. Only the mixture of compounds 2 and 4 (ratio 1:2) showed weak cytotoxic activity against the tested cancer cell lines with an IC50 of 23 µg/mL. Moreover, the new compounds 2 and 3, as well as the known compounds 5 and 6, interfered with the biofilm formation of Staphylococcus aureus, inhibiting 65%, 75%, 79%, and 76% of biofilm at 250 µg/mL, respectively. Compounds 5 and 6 also exhibited moderate activity against S. aureus preformed biofilm with the highest inhibition percentage of 75% and 73% at 250 µg/mL, respectively.

Published
2020

36. Lachnuoic Acids A-F: Ambuic Acid Congeners from a Saprotrophic Lachnum Species.

Author

Phutthacharoen K, Toshe R, Khalid SJ, Llanos-López NA, Wennrich JP, Schrey H, Ebada SS, Hyde KD, and Stadler M

Subjects
Molecular Structure, Cyclohexanones, Ascomycota chemistry, Anti-Infective Agents pharmacology, Anti-Infective Agents chemistry
Abstract

Chemical prospection of an extract derived from a saprotrophic fungus Lachnum sp. IW157 resulted in the isolation and characterization of six unprecedentedly reported ambuic acid analogues named lachnuoic acids A-F (1-6). Chemical structures of 1-6 were determined based on comprehensive 1D and 2D NMR spectroscopic analyses together with HR-ESI-MS spectrometry. The relative configurations of 1-3 were defined by ROESY spectroscopic analyses while their absolute configurations were unambiguously determined by Mosher's esters method. All isolated compounds were subjected to cytotoxic, antimicrobial, antibiofilm and nematicidal activity assays where only lachnuoic acid A (1) revealed potent antimicrobial activity against Staphylococcus aureus and Bacillus subtilis at MIC values of 16.6 and 8.3 μg/mL, respectively., (© 2024 The Authors. Chemistry & Biodiversity published by Wiley‐VHCA AG.)

Published
2024
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37. Syntheses and Biofilm Reducing Effects of l-Dopa-Derived Analogues of the Fungal Macrocidins A and Z.

Author

Pezolt C, Karau A, Schobert R, and Schrey H

Subjects
Structure-Activity Relationship, Anti-Bacterial Agents pharmacology, Tyrosine, Levodopa, Biofilms
Abstract

Four analogues of the fungal metabolites macrocidin A and Z, featuring [13]para- or [13]metacyclophanes, were synthesised from fully and orthogonally protected l-dopa instead of l-tyrosine. They were tested for antibiotic activities and for effects on the growth and persistence of microbial biofilms. Tentative structure-activity relationships and distinct differences when compared with the natural lead compounds were identified., (© 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.)

Published
2023
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38. Aminotenuazonic Acid: Isolation, Structure Elucidation, Total Synthesis and Herbicidal Activity of a New Tetramic Acid from Fruiting Bodies of Laccaria Species.

Author

Schrey H, Backenköhler J, Kogler H, Plaumann M, and Spiteller P

Subjects
Arabidopsis, Catalysis, Cyclization, Herbicides chemical synthesis, Lepidium sativum, Oxidation-Reduction, Pinus sylvestris, Plant Roots, Plant Shoots, Tenuazonic Acid chemical synthesis, Fruiting Bodies, Fungal chemistry, Herbicides isolation & purification, Laccaria chemistry, Tenuazonic Acid analogs & derivatives, Tenuazonic Acid isolation & purification
Abstract

(5S,6S)-Aminotenuazonic acid, a new 3-acyltetramic acid, related to the well-known mycotoxin tenuazonic acid has been isolated from fruiting bodies of Laccaria bicolor. Its structure was mostly established by analysis of its 2D NMR and HR-(+)-ESI-MS spectra. A total synthesis starting from N-Boc-l-isoleucine gave (5S,6S)-aminotenuazonic acid in 8 % yield over nine steps (67 % de). The key steps of the total synthesis are a light-initiated Hofmann-Löffler-Freytag radical chain reaction and a Dieckmann cyclisation. The relative and absolute configurations of the natural product were determined by comparison of its NMR and CD spectra with those of the corresponding enantiopure synthetic compounds. Metabolic profiling of crude extracts of different mushrooms showed that aminotenuazonic acid is present in all four of the investigated Laccaria species. Aminotenuazonic acid shows phytotoxic activities against the root and shoot growth of Lepidium sativum, Pinus sylvestris and Arabidopsis thaliana comparable to those of tenuazonic acid., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2019
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39. E- and Z-Proxamidines, Unprecedented 1,3-Diazacyclooct-1-ene Alkaloids from Fruiting Bodies of Laccaria proxima.

Author

Schrey H and Spiteller P

Abstract

Fruiting bodies of Laccaria proxima were screened for the presence of new secondary metabolites by means of HPLC-UV and LC-HR-(+)-ESIMS. Thus, two isomeric alkaloids with a highly unusual core structure, E-proxamidine and its Z-isomer, were isolated from Laccaria proxima. The proxamidines consist of an eight-membered heterocyclic ring system with a formamidine unit. The structures were established by 2D NMR spectroscopic methods, HR-(+)-ESIMS, and HR-(+)-ESIMS/MS. The proxamidines are probably biosynthetically derived from tryptophan, dimethylallyl pyrophosphate, and S-adenosylmethionine and the eight-membered ring of the proxamidines is likely to be generated by a rearrangement of the tryptophan sceleton. Metabolic profiling of fruiting bodies of some other Laccaria species revealed that the proxamidines appear in significant amounts only in L. proxima making the compounds suitable as chemotaxonomic markers. E-Proxamidine exhibits herbicidal activity against Lepidium sativum., (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Published
2019
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