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Journal articles on the topic 'Peptaibol Antibiotics'

Author: Grafiati

Published: 4 June 2021

Last updated: 6 September 2023

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1

Víglaš, Ján, Simona Dobiasová, Jitka Viktorová, et al. "Peptaibol-Containing Extracts of Trichoderma atroviride and the Fight against Resistant Microorganisms and Cancer Cells." Molecules 26, no. 19 (2021): 6025. http://dx.doi.org/10.3390/molecules26196025.

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Fighting resistance to antibiotics and chemotherapeutics has brought bioactive peptides to the fore. Peptaibols are short α-aminoisobutyric acid-containing peptides produced by Trichoderma species. Here, we studied the production of peptaibols by Trichoderma atroviride O1 and evaluated their antibacterial and anticancer activity against drug-sensitive and multidrug-resistant bacterium and cancer cell lines. This was substantiated by an analysis of the activity of the peptaibol synthetase-encoding gene. Atroviridins, 20-residue peptaibols were detected using MALDI-TOF mass spectrometry. Gram-po

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2

HÜLSMANN, HEIKE, STEPHAN HEINZE, MICHAEL RITZAU, BRIGITTE SCHLEGEL, and UDO GRÄFE. "Isolation and Structure of Peptaibolin, a New Peptaibol from Sepedonium Strains." Journal of Antibiotics 51, no. 11 (1998): 1055–58. http://dx.doi.org/10.7164/antibiotics.51.1055.

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3

Dalla Torre, Chiara, Filomena Sannio, Mattia Battistella, Jean-Denis Docquier, and Marta De Zotti. "Peptaibol Analogs Show Potent Antibacterial Activity against Multidrug Resistant Opportunistic Pathogens." International Journal of Molecular Sciences 24, no. 9 (2023): 7997. http://dx.doi.org/10.3390/ijms24097997.

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New classes of antibacterial drugs are urgently needed to address the global issue of antibiotic resistance. In this context, peptaibols are promising membrane-active peptides since they are not involved in innate immunity and their antimicrobial activity does not involve specific cellular targets, therefore reducing the chance of bacterial resistance development. Trichogin GA IV is a nonhemolytic, natural, short-length peptaibol active against Gram-positive bacteria and resistant to proteolysis. In this work, we report on the antibacterial activity of cationic trichogin analogs. Several pepti

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4

SHARMAN, Gary J., Andrew C. TRY, Dudley H. WILLIAMS, et al. "Structural elucidation of XR586, a peptaibol-like antibiotic from Acremonium persicinum." Biochemical Journal 320, no. 3 (1996): 723–28. http://dx.doi.org/10.1042/bj3200723.

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A novel peptide, XR586, has been isolated from fermentations of Acremonium persicinum (Xenova culture collection number X21488). The structure of XR586 has been elucidated by means of NMR spectroscopy, electrospray and fast-atom bombardment MS, derivatization and enzymic digestion. It has been shown to be helical by CD measurements. XR586 shows many structural and conformational features in common with peptaibols, particularly the zervamicins. Peptaibol antibiotics are peptides, typically of 15–20 residues, containing a large proportion of α-aminoisobutyric acid (Aib) residues. These peptides

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5

DORNBERGER, KLAUSJÜRGEN, WOLFGANG IHN, MICHAEL RITZAU, et al. "Chrysospermins, New Peptaibol Antibiotics from Apiocrea chrysosperma Ap101." Journal of Antibiotics 48, no. 9 (1995): 977–89. http://dx.doi.org/10.7164/antibiotics.48.977.

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6

CHIKANISHI, TOSHIHIRO, KEIJI HASUMI, TOMOTAKA HARADA, NOBUHIDE KAWASAKI, and AKIRA ENDO. "Clonostachin, a Novel Peptaibol That Inhibits Platelet Aggregation." Journal of Antibiotics 50, no. 2 (1997): 105–10. http://dx.doi.org/10.7164/antibiotics.50.105.

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7

ISHIYAMA, DAISUKE, TSUTOMU SATOU, HISATO SENDA, TSUKASA FUJIMAKI, REIKO HONDA, and SUSUMU KANAZAWA. "Heptaibin, a Novel Antifungal Peptaibol Antibiotic from Emericellopsis sp. BAUA8289." Journal of Antibiotics 53, no. 7 (2000): 728–32. http://dx.doi.org/10.7164/antibiotics.53.728.

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8

Grigoriev, Pavel, Rolf Schlegel, Klausjürgen Dornberger, and Udo Gräfe. "Formation of membrane channels by chrysospermins, new peptaibol antibiotics." Biochimica et Biophysica Acta (BBA) - Biomembranes 1237, no. 1 (1995): 1–5. http://dx.doi.org/10.1016/0005-2736(95)00072-b.

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9

SCHIELL, MATTHIAS, JOACHIM HOFMANN, MICHAEL KURZ, et al. "Cephaibols, New Peptaibol Antibiotics with Anthelmintic Properties from Acremonium tubakii DSM 12774." Journal of Antibiotics 54, no. 3 (2001): 220–33. http://dx.doi.org/10.7164/antibiotics.54.220.

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10

LECLERC, GREGORY, SYLVIE REBUFFAT, and BERNARD BODO. "Directed Biosynthesis of Peptaibol Antibiotics in Two Trichoderma Strains. II. Structure Elucidation." Journal of Antibiotics 51, no. 2 (1998): 178–83. http://dx.doi.org/10.7164/antibiotics.51.178.

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11

Jaworski, Andreas, and Hans Br�ckner. "New sequences and new fungal producers of peptaibol antibiotics antiamoebins." Journal of Peptide Science 6, no. 4 (2000): 149–67. http://dx.doi.org/10.1002/(sici)1099-1387(200004)6:4<149::aid-psc235>3.0.co;2-m.

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12

LECLERC, GREGORY, SYLVIE REBUFFAT, CHRISTOPHE GOULARD, and BERNARD BODO. "Directed Biosynthesis of Peptaibol Antibiotics in Two Trichoderma Strains. I. Fermentation and Isolation." Journal of Antibiotics 51, no. 2 (1998): 170–77. http://dx.doi.org/10.7164/antibiotics.51.170.

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13

Maddau, Lucia, Annalisa Cabras, Antonio Franceschini, et al. "Occurrence and characterization of peptaibols from Trichoderma citrinoviride, an endophytic fungus of cork oak, using electrospray ionization quadrupole time-of-flight mass spectrometry." Microbiology 155, no. 10 (2009): 3371–81. http://dx.doi.org/10.1099/mic.0.030916-0.

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A cork oak endophytic strain of Trichoderma citrinoviride, previously selected for its antagonistic potential against various fungal pathogens involved in oak decline, was screened for the production of bioactive secondary metabolites. From liquid culture a mixture of polypeptide antibiotics (peptaibols) belonging to the paracelsin family was isolated and characterized. This peptide mixture was purified by column chromatography and preparative TLC on silica gel, and separated by analytical HPLC. It was analysed by MALDI-TOF MS and nano-ESI-QTOF MS. Tandem mass experiments were performed to det

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14

BERG, A., M. RITZAU, W. IHN, et al. "Isolation and Structure of Bergofungin, a New Antifungal Peptaibol from Emericellopsis donezkii HKI 0059." Journal of Antibiotics 49, no. 8 (1996): 817–20. http://dx.doi.org/10.7164/antibiotics.49.817.

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15

BENEDETTI, ETTORE, ALFONSO BAVOSO, BENEDETTO BLASIO, et al. "Protected 1-3 segment of the peptaibol antibiotics alamethicin and hypelcin." International Journal of Peptide and Protein Research 22, no. 4 (2009): 385–97. http://dx.doi.org/10.1111/j.1399-3011.1983.tb02107.x.

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16

Aubry, André, Daniel Bayeul, Hans Brückner, Norbert Schiemann, and Ettore Benedetti. "The crystal state conformation of Aib-rich segments of peptaibol antibiotics." Journal of Peptide Science 4, no. 8 (1998): 502–10. http://dx.doi.org/10.1002/(sici)1099-1387(199812)4:8<502::aid-psc171>3.0.co;2-n.

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17

Chugh, J. K., and B. A. Wallace. "Peptaibols: models for ion channels." Biochemical Society Transactions 29, no. 4 (2001): 565–70. http://dx.doi.org/10.1042/bst0290565.

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Peptaibols are membrane-active polypeptides isolated from fungal sources. They are characterized by the presence of an unusual amino acid, α-aminoisobutyric acid, and a C-terminal hydroxylated amino acid. Peptaibols exhibit antibiotic activity against bacteria and fungi. Their amphipathic nature allows them to self-associate into oligomeric ion-channel assemblies which span the width of lipid bilayer membranes. Over 200 peptaibol sequences have been reported to date, which are compiled in the Peptaibol Database at http://www.cryst.bbk.ac.uk/peptaibol. Alignments of these sequences have been ca

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18

RITZAU, MICHAEL, STEPHAN HEINZE, KLAUSJÜRGEN DORNBERGER, et al. "Ampullosporin, a New Peptaibol-type Antibiotic from Sepedonium ampullosporum HKI-0053 with Neuroleptic Activity in Mice." Journal of Antibiotics 50, no. 9 (1997): 722–28. http://dx.doi.org/10.7164/antibiotics.50.722.

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19

Jaworski, Andreas, and Hans Brückner. "Sequences of polypeptide antibiotics stilboflavins, natural peptaibol libraries of the moldStilbella flavipes." Journal of Peptide Science 7, no. 8 (2001): 433–47. http://dx.doi.org/10.1002/psc.335.

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20

Jaworski, Andreas, Jochen Kirschbaum, and Hans Brückner. "Structures of trichovirins II, peptaibol antibiotics from the moldTrichoderma viride NRRL 5243." Journal of Peptide Science 5, no. 8 (1999): 341–51. http://dx.doi.org/10.1002/(sici)1099-1387(199908)5:8<341::aid-psc204>3.0.co;2-0.

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21

Schiell, Matthias, Joachim Hofmann, Michael Kurz, et al. "ChemInform Abstract: Cephaibols, New Peptaibol Antibiotics with Anthelmintic Properties from Acremonium tubakii DSM 12774." ChemInform 32, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.200134235.

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22

OH, SEUNG-UK, BONG-SIK YUN, SANG-JUN LEE, JUNG-HAN KIM, and ICK-DONG YOO. "Atroviridins A-C and Neoatroviridins A-D, Novel Peptaibol Antibiotics Produced by Trichoderma atroviride F80317. I. Taxonomy, Fermentation, Isolation and Biological Activities." Journal of Antibiotics 55, no. 6 (2002): 557–64. http://dx.doi.org/10.7164/antibiotics.55.557.

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23

Brückner, H., and C. Reinecke. "Chromatographic assays for the rapid and sensitive detection of peptaibol mycotoxins (antibiotics) in filamentous fungi." Journal of High Resolution Chromatography 12, no. 2 (1989): 113–16. http://dx.doi.org/10.1002/jhrc.1240120213.

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24

Becker, Dieter, Michael Kiess, and Hans Brückner. "Structures of Peptaibol Antibiotics Hypomurocin A and B from the Ascomycetous FungusHypocrea muroiana hino et katsumoto." Liebigs Annalen 1997, no. 4 (1997): 767–72. http://dx.doi.org/10.1002/jlac.199719970421.

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25

LECLERC, G., S. REBUFFAT, C. GOULARD, and B. BODO. "ChemInform Abstract: Directed Biosynthesis of Peptaibol Antibiotics in Two Trichoderma Strains. Part 1. Fermentation and Isolation." ChemInform 29, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199827299.

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26

Jaworski, Andreas, and Hans Brückner. "Detection of new sequences of peptaibol antibiotics trichotoxins A-40 by on-line liquid chromatography–electrospray ionization mass spectrometry." Journal of Chromatography A 862, no. 2 (1999): 179–89. http://dx.doi.org/10.1016/s0021-9673(99)00931-0.

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27

BECKER, D., M. KIESS, and H. BRUECKNER. "ChemInform Abstract: Structures of Peptaibol Antibiotics Hypomurocin A and B from the Ascomycetous Fungus Hypocrea muroiana Hino et Katsumoto." ChemInform 28, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199733315.

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28

Bardi, Renato, Anna Maria Piazzesi, Claudio Toniolo, Ole E. Jensen, Rashad S. Omar, and Alexander Senning. "Molecular and crystal structures of three monothiated analogues of the terminally blocked ala-aib-ala sequence of peptaibol antibiotics." Biopolymers 27, no. 5 (1988): 747–61. http://dx.doi.org/10.1002/bip.360270504.

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29

Gessmann, Renate, Danny Axford, Hans Brückner, Albrecht Berg, and Kyriacos Petratos. "A natural, single-residue substitution yields a less active peptaibiotic: the structure of bergofungin A at atomic resolution." Acta Crystallographica Section F Structural Biology Communications 73, no. 2 (2017): 95–100. http://dx.doi.org/10.1107/s2053230x17001236.

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Bergofungin is a peptide antibiotic that is produced by the ascomycetous fungusEmericellopsis donezkiiHKI 0059 and belongs to peptaibol subfamily 2. The crystal structure of bergofungin A has been determined and refined to 0.84 Å resolution. This is the second crystal structure of a natural 15-residue peptaibol, after that of samarosporin I. The amino-terminal phenylalanine residue in samarosporin I is exchanged to a valine residue in bergofungin A. According to agar diffusion tests, this results in a nearly inactive antibiotic peptide compared with the moderately active samarosporin I. Crysta

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30

Grigoriev, P. A., A. Berg, R. Schlegel, and U. Gräfe. "Differences in ion permeability of an artificial bilayer membrane caused by ampullosporin and bergofungin, new 15-membered peptaibol-type antibiotics." Bioelectrochemistry and Bioenergetics 44, no. 1 (1997): 155–58. http://dx.doi.org/10.1016/s0302-4598(97)00063-9.

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31

Valle, Giovanni, Marco Crisma, Claudio Toniolo, Rudolf Beißwenger, Anton Rieker, and Günther Jung. "Molecular and Crystal Structures of Two Terminally Blocked Tripeptides Corresponding to the 3–5 Sequence of the Peptaibol Antibiotics Antiamoebins." Liebigs Annalen der Chemie 1989, no. 4 (1989): 337–43. http://dx.doi.org/10.1002/jlac.198919890159.

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32

Toniolo, Claudio, Gian Maria Bonora, Ettore Benedetti, et al. "Linear oligopeptides: peptaibol antibiotics — preferred conformation of the 2–9 segment of emerimicins III and IV and all related short sequences." International Journal of Biological Macromolecules 7, no. 6 (1985): 357–62. http://dx.doi.org/10.1016/0141-8130(85)90050-9.

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33

Rogozhin, Eugene, Vera Sadykova, Anna Baranova, et al. "A Novel Lipopeptaibol Emericellipsin A with Antimicrobial and Antitumor Activity Produced by the Extremophilic Fungus Emericellopsis alkalina." Molecules 23, no. 11 (2018): 2785. http://dx.doi.org/10.3390/molecules23112785.

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Soil fungi are known to contain a rich variety of defense metabolites that allow them to compete with other organisms (fungi, bacteria, nematodes, and insects) and help them occupy more preferential areas at the expense of effective antagonism. These compounds possess antibiotic activity towards a wide range of other microbes, particularly fungi that belong to different taxonomical units. These compounds include peptaibols, which are non-ribosomal synthesized polypeptides containing non-standard amino acid residues (alpha-aminoisobutyric acid mandatory) and some posttranslational modifications

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34

Schirmböck, M., M. Lorito, Y. L. Wang, et al. "Parallel formation and synergism of hydrolytic enzymes and peptaibol antibiotics, molecular mechanisms involved in the antagonistic action of Trichoderma harzianum against phytopathogenic fungi." Applied and Environmental Microbiology 60, no. 12 (1994): 4364–70. http://dx.doi.org/10.1128/aem.60.12.4364-4370.1994.

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35

Ribeiro, Ana R. M., Helena P. Felgueiras, Susana P. G. Costa, and Sílvia M. M. A. Pereira-Lima. "Synthesis of Peptaibolin, an Antimicrobial Peptide." Proceedings 78, no. 1 (2020): 47. http://dx.doi.org/10.3390/iecp2020-08654.

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To tackle one of the biggest global health problems, the resistance of microorganisms to antibiotics, a collective effort in the search for more effective agents against bacteria was required. Peptides with antimicrobial activity have been raising much attention as a promising alternative for antibiotics. Peptaibols, for instance, are a family of antimicrobial peptides (AMPs) with great biomedical potential, in which the Peptaibolin can be highlighted. This peptide has gained relevance due to its small amino acids content, only four, and its acetyl group and a phenylalaninol residue (Phol) at

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36

Toniolo, Claudio, Gian Maria Bonora, Alfonso Bavoso, et al. "Molecular Structure of Peptaibol Antibiotics: Solution Conformation and Crystal Structure of the Octapeptide Corresponding to the 2–9 Sequence of Emerimicins III and IV." Journal of Biomolecular Structure and Dynamics 3, no. 3 (1985): 585–98. http://dx.doi.org/10.1080/07391102.1985.10508446.

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37

Oh, Seung-Uk, Bong-Sik Yun, Sang-Jun Lee, Jung-Han Kim, and Ick-Dong Yoo. "ChemInform Abstract: Atroviridins A-C and Neoatroviridins A-D, Novel Peptaibol Antibiotics Produced by Trichoderma atroviride F80317. Part 1. Taxonomy, Fermentation, Isolation and Biological Activities." ChemInform 33, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.200245211.

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38

Sabareesh, Varatharajan, and Padmanabhan Balaram. "Tandem electrospray mass spectrometric studies of proton and sodium ion adducts of neutral peptides with modified N- and C-termini: synthetic model peptides and microheterogeneous peptaibol antibiotics." Rapid Communications in Mass Spectrometry 20, no. 4 (2006): 618–28. http://dx.doi.org/10.1002/rcm.2349.

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39

Sabareesh, Varatharajan, and Padmanabhan Balaram. "Corrigendum: Tandem electrospray mass spectrometric studies of proton and sodium ion adducts of neutral peptides with modified N- and C- termini: synthetic model peptides and microheterogeneous peptaibol antibiotics." Rapid Communications in Mass Spectrometry 21, no. 19 (2007): 3227. http://dx.doi.org/10.1002/rcm.3200.

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40

Ovchinnikova, T. V., and A. N. Murashev. "The peptaibol antibiotic zervamicin displays neurotropic activity." Doklady Biochemistry and Biophysics 414, no. 1 (2007): 146–48. http://dx.doi.org/10.1134/s1607672907030143.

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41

Rogozhin, Eugene, and Vera Sadykova. "A Lipoaminopeptaibol Secreted by Alkalophilic Fungus Emericellopsis alkalina Demonstrates a Strong Cytotoxic Effect against Tumor Cell Lines." Proceedings 22, no. 1 (2019): 4. http://dx.doi.org/10.3390/proceedings2019022004.

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Soil fungi are known to produce and secrete antibiotics with a strong antimicrobial effect towards eukaryotic organisms. In many occasions, these compounds belong to peptides that are products of non-ribosomal biosynthesis and are called peptaibols. Many peptaibols are cytotoxic and some of them suppress tumor cell lines much better than normal cells by inducing calcium-mediated apoptosis. The main antimicrobial lipoaminopeptaibol—emericellipsin A—isolated from the fungus Emericellopsis alkalina strain VKPM F-1428, which demonstrates promising antifungal activity against different fungal taxon

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42

Tsantrizos, Youla S., Sotiria Pischos, Françoise Sauriol, and Paul Widden. "Peptaibol metabolites of Tolypocladium geodes." Canadian Journal of Chemistry 74, no. 2 (1996): 165–72. http://dx.doi.org/10.1139/v96-020.

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Three antibiotic peptides, LP237-F8 (1), F5 (2), and F7 (3), were isolated from the liquid culture of the fungus Tolypocladium geodes. Chemical shift assignments of the 1H and 13C NMR resonances and sequencing of these metabolites were achieved by extensive high-field 2D NMR spectroscopy. The N-terminal of peptides 1 and 2 is protected with an octanoyl (Oc) fatty acid unit, whereas that of peptide 3 is protected with a decanoyl (Dec) unit. The C-terminal of all three peptides is protected with the amino alcohol leucinol (Lol). All three metabolites contain the common amino acids Ala, Phe or Ty

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43

Ogrel, Andrei, Alexei Ogrel, Svetlana Ogrel, Vitaliy Shvets, and Jan Raap. "Synthesis of the15N-Gln11 labeled peptaibol antibiotic zervamicin-IIB." Letters in Peptide Science 5, no. 2-3 (1998): 175–78. http://dx.doi.org/10.1007/bf02443464.

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44

Duclohier, Herve. "Antimicrobial Peptides and Peptaibols, Substitutes for Conventional Antibiotics." Current Pharmaceutical Design 16, no. 28 (2010): 3212–23. http://dx.doi.org/10.2174/138161210793292500.

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45

Duclohier, Hervé. "Peptaibiotics and Peptaibols: An Alternative to Classical Antibiotics?" Chemistry & Biodiversity 4, no. 6 (2007): 1023–26. http://dx.doi.org/10.1002/cbdv.200790094.

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46

Br�ckner, H., and A. Koza. "Solution phase synthesis of the 14-residue peptaibol antibiotic trichovirin I." Amino Acids 24, no. 3 (2003): 311–23. http://dx.doi.org/10.1007/s00726-002-0401-x.

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47

BERG, ALBRECHT, BRIGITTE SCHLEGEL, WOLFGANG IHN, ULRICH DEMUTH, and UDO GRÄFE. "Isolation and Structural Elucidation of New Peptaibols, Bergofungins B, C and D, from Emericellopsis donezkii HKI 0059." Journal of Antibiotics 52, no. 7 (1999): 666–69. http://dx.doi.org/10.7164/antibiotics.52.666.

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48

Ovchinnikova, T. V., M. B. Baru, E. Yu Gorbunova, et al. "Total Solid Phase Synthesis of the Biologically Active Peptaibol Antibiotic Zervamicin IIB." Biochemical Society Transactions 28, no. 5 (2000): A207. http://dx.doi.org/10.1042/bst028a207.

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49

Kropacheva, T. N., and J. Raap. "Voltage-dependent interaction of the peptaibol antibiotic zervamicin II with phospholipid vesicles." FEBS Letters 460, no. 3 (1999): 500–504. http://dx.doi.org/10.1016/s0014-5793(99)01401-5.

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50

Krause, Corina, Jochen Kirschbaum, Günther Jung, and Hans Brückner. "Sequence diversity of the peptaibol antibiotic suzukacillin-A from the moldTrichoderma viride." Journal of Peptide Science 12, no. 5 (2006): 321–27. http://dx.doi.org/10.1002/psc.728.

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