Lipovelutibols A–D: Cytotoxic Lipopeptaibols from the Himalayan Cold Habitat Fungus <i>Trichoderma velutinum</i>

Singh, Varun Pratap; Nalli, Yedukondalu; Sharma, Vandana; Kushwaha, Manoj; Sharma, Richa; Chaubey, Asha; Kumar, Anil; Singh, Deepika; Vishwakarma, Ram A.

doi:10.1021/acs.jnatprod.6b00873

Cited by 30 publications

(33 citation statements)

References 34 publications

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“…There is a wide structural diversity among peptaibols from Trichoderma spp., many of which are found to have single amino acid substitutions [51]. In some cases, peptaibols from Trichoderma are isolated as groups of homologous peptides that have certain variability in their amino acid sequence, which influences the quantitative level of biological activity, particularly cytotoxicity as a rule [52][53][54]. Semi-synthetic analogues based on peptaibol trichogin isolated from Trichoderma sp.…”

Section: Discussionmentioning

confidence: 99%

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The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

Куварина¹,

Gavryushina²,

Kul'ko

et al. 2021

JoF

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Novel antimicrobial peptides with antifungal and cytotoxic activity were derived from the alkalophilic fungus Emericellopsis alkalina VKPM F1428. We previously reported that this strain produced emericellipsin A (EmiA), which has strong antifungal and cytotoxic properties. Further analyses of the metabolites obtained under a special alkaline medium resulted in the isolation of four new homologous (Emi B–E). In this work, we report the complete primary structure and detailed biological activity for the newly synthesized nonribosomal antimicrobial peptides called emericellipsins B–E. The inhibitory activity of themajor compound, EmiA, against drug-resistant pathogenic fungi was similar to that of amphotericin B (AmpB). At the same time, EmiA had no hemolytic activity towards human erythrocytes. In addition, EmiA demonstrated low cytotoxic activity towards the normal HPF line, but possessed cancer selectivity to the K-562 and HCT-116 cell lines. Emericillipsins from the alkalophilic fungus Emericellopsis alkaline are promising treatment alternatives to licensed antifungal drugs for invasive mycosis therapy, especially for multidrug-resistant aspergillosis and cryptococcosis.

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Section: Discussionmentioning

confidence: 99%

“…It was shown that this modification increased peptide amphiphilicity and did not lead to critical changes of 3D orientation. Concerning functional aspects, most of the mutant peptaibols could improve the inhibition effect towards B. cinerea [54].…”

Section: Discussionmentioning

confidence: 99%

The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

Куварина¹,

Gavryushina²,

Kul'ko

et al. 2021

JoF

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“…Peptaibols were a family of linear peptides generally composed of 5–20 amino acid residues, characterized by N‐acyl terminus, C‐amino alcohol terminus, and a high proportion of nonproteinogenic amino acids such as α ‐aminoisobutyric acid (Aib) or isovaline (Iva) [5–12] . Peptaibols usually showed antibacterial, [6,7] antifungal, [6–9] antiviral [10] or cytotoxic activities [5,11,12] . The bioactivities of peptaibols were affected strongly by the number of amino residues, and enhanced with the increasing of the amino residues [13] .…”

Section: Introductionmentioning

confidence: 99%

Longibramides A–E, Peptaibols Isolated from a Mushroom Derived Fungus Trichoderma longibrachiatum Rifai DMG‐3‐1‐1

Zhang

Yang²,

Ma³

et al. 2021

Chemistry & Biodiversity

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Five new peptaibols, longibramides A–E (1–5) with 11 amino acid residues, were isolated from a fungus Trichoderma longibrachiatum Rifai DMG‐3‐1‐1, which was isolated from a mushroom Clitocybe nebularis (Batsch) P. Kumm collected from coniferous forest in the subboreal area of northeast China. The structures of longibramides A–E were determined by their spectroscopic data (NMR and MS‐MS spectra), their absolute configurations were determined by X‐ray diffractions and Marfey's analyses. The X‐ray diffractions of longibramides A, B, and the similar CD spectra of A–E showed that they all had α‐helix conformations. Longibramides B and E showed moderate cytotoxicities against BV2 and MCF‐7 cells and also showed some inhibitory effects against methicillin‐resistant Staphylococcus aureus MRSA T144. L‐trans‐Hyp was not commonly found in natural peptaibols, which was the 6th or 10th amino acid residue in longibramides C–E. The X‐ray diffractions of longibramides A and B afforded the accuracy conformations of their secondary structures, which maybe help to interpret the structure‐activity relationships of the family of peptaibols in the future.

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“…Peptaibols (nonribosomal linear oligopeptides with the reduced C-terminal fragment that contain αbranched amino acids, i.e., α-aminoizobutanoic acid and/or isovaline) are a common type of peptide secondary metabolites of micromycetes among linear peptides. In recent years, two new representatives of this structural type, i.e., lipovelutibols A-D (22-25) [56] and emericellipsin A (26) [57] have been isolated from extremophilic micromycetes. Features of lipovelutibols B (23) and D (25) are the presence of nonproteinogenic amino acid D-isovaline and the absence of α-aminoisobutanoic acid in their molecules, previously described among all peptaibols.…”

Section: Peptides Diketopiperazines and Related Compoundsmentioning

confidence: 99%

Antibiotics from Extremophilic Micromycetes

et al. 2020

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Extremophilic microorganisms, which are capable of functioning normally at extremely high or low temperatures, pressure, and in other environmental conditions, have been in the focus of microbiologists’ attention for several decades due to the biotechnological potential of enzymes inherent in extremophiles. These enzymes (also called extremozymes) are used in the production of food and detergents and other industries. At the same time, the inhabitants of extreme econiches remained almost unexplored for a long time in terms of the chemistry of natural compounds. In recent years, the emergence of new antibiotic-resistant strains of pathogens, which affect humans and animals has become a global problem. The problem is compounded by a strong slowdown in the development of new antibiotics. In search of new active substances and scaffolds for medical chemistry, researchers turn to unexplored natural sources. In recent years, there has been a sharp increase in the number of studies on secondary metabolites produced by extremophiles. From the discovery of penicillin to the present day, micromycetes, along with actinobacteria, are one of the most productive sources of antibiotic compounds for medicine and agriculture. Many authors consider extremophilic micromycetes as a promising source of small molecules with an unusual mechanism of action or significant structural novelty. This review summarizes the latest (for 2018–2019) experimental data on antibiotic compounds, which are produced by extremophilic micromycetes with various types of adaptation. Active metabolites are classified by the type of structure and biosynthetic origin. The data on the biological activity of the isolated metabolites are summarized.

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Lipovelutibols A–D: Cytotoxic Lipopeptaibols from the Himalayan Cold Habitat Fungus Trichoderma velutinum

Cited by 30 publications

References 34 publications

The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

The Emericellipsins A–E from an Alkalophilic Fungus Emericellopsis alkalina Show Potent Activity against Multidrug-Resistant Pathogenic Fungi

Longibramides A–E, Peptaibols Isolated from a Mushroom Derived Fungus Trichoderma longibrachiatum Rifai DMG‐3‐1‐1

Antibiotics from Extremophilic Micromycetes

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