Strategy for the Biosynthesis of Short Oligopeptides: Green and Sustainable Chemistry

Wang, Tao; Zhang, Yu-Ran; Liu, Xiaohuan; Ge, Shun; Zhu, Youshuang

doi:10.3390/biom9110733

Cited by 11 publications

(6 citation statements)

References 119 publications

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“…The γ-lactam moiety of 1−4 could be derived from two molecules of amino acids (homoserine with leucine, (R)-2-amino-5-methylhex-5-enoic acid, phenylalanine, and tyrosine, respectively) catalyzed by nonribosomal peptide synthetase (NRPS), followed by a series of reactions including oxidation, dehydration, intramolecular condensation, reduction, and methylation as illustrated in Scheme 1. 53,54 Biological Activity. The antibacterial activities of all compounds were evaluated.…”

Section: Molecularmentioning

confidence: 99%

New Cytotoxic γ-Lactam Alkaloids from the Mangrove-Derived Fungus Talaromyces hainanensis sp. nov. Guided by Molecular Networking Strategy

Shi,

Sun,

Zhang

et al. 2024

J. Agric. Food Chem.

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The fungus Talaromyces hainanensis, isolated from the mangrove soil, was characterized as a novel species by morphology observation and phylogenetic analyses. Four new γ-lactam alkaloids talaroilactams A−D (1−4) and two reported compounds harzianic acid (5) and isoharzianic acid (6) were identified from the fungus T. hainanensis WHUF0341, assisted by OSMAC along with molecular networking approaches. Their structures were determined through ECD calculations and spectroscopic analyses. Moreover, the biosynthetic route of 1−4 was also proposed. Compound 1 displayed potent cytotoxicity against HepG2 cell lines, with an IC 50 value of 10.75 ± 1.11 μM. In addition, network pharmacology was employed to dissect the probable mechanisms contributing to the antihepatocellular carcinoma effects of compound 1, revealing that cytotoxicity was mainly associated with proteolysis, negative regulation of autophagy, inflammatory response, and the renin-angiotensin system. These results not only expanded the chemical space of natural products from the mangrove associated fungi but also afforded promising lead compounds for developing the antihepatocellular carcinoma agents.

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Section: Molecularmentioning

confidence: 99%

New Cytotoxic γ-Lactam Alkaloids from the Mangrove-Derived Fungus Talaromyces hainanensis sp. nov. Guided by Molecular Networking Strategy

Shi,

Sun,

Zhang

et al. 2024

J. Agric. Food Chem.

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“…Thus, bio-herbicides from natural sources are required. DKPs are promising nature-inspired herbicides due to their environmental friendliness, safety, high selectivity, and probable new target sites [322][323][324]. Proline-derived DKPs have specific herbicide activities [32].…”

Section: Activators Of Dioxygen In Oxidative Processesmentioning

confidence: 99%

Cyclic Dipeptides: The Biological and Structural Landscape with Special Focus on the Anti-Cancer Proline-Based Scaffold

et al. 2021

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Cyclic dipeptides, also know as diketopiperazines (DKP), the simplest cyclic forms of peptides widespread in nature, are unsurpassed in their structural and bio-functional diversity. DKPs, especially those containing proline, due to their unique features such as, inter alia, extra-rigid conformation, high resistance to enzyme degradation, increased cell permeability, and expandable ability to bind a diverse of targets with better affinity, have emerged in the last years as biologically pre-validated platforms for the drug discovery. Recent advances have revealed their enormous potential in the development of next-generation theranostics, smart delivery systems, and biomaterials. Here, we present an updated review on the biological and structural profile of these appealing biomolecules, with a particular emphasis on those with anticancer properties, since cancers are the main cause of death all over the world. Additionally, we provide a consideration on supramolecular structuring and synthons, based on the proline-based DKP privileged scaffold, for inspiration in the design of compound libraries in search of ideal ligands, innovative self-assembled nanomaterials, and bio-functional architectures.

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“…It was also hypothesized that biological activity of short sequence peptides is associated with their prominent antioxidant properties, although this data is contradictory as some oligopeptides were reported to have prooxidant effect. A number of studies have demonstrated the effect of short peptides on the proliferation and differentiation of stem cells [14,33]. Several oligopeptides were reported to exert potent geroprotective effect due to the inhibition of apoptosis, induction of telomerase activity and telomere elongation in human fibroblast culture, which can be due to reactivation of the telomerase gene in somatic cells and indicates the possibility of prolonging the life span of a cell population [33].…”

Section: The Mechanism Of Action Of Short Sequence Peptidesmentioning

confidence: 99%

“…A number of studies have demonstrated the effect of short peptides on the proliferation and differentiation of stem cells [14,33]. Several oligopeptides were reported to exert potent geroprotective effect due to the inhibition of apoptosis, induction of telomerase activity and telomere elongation in human fibroblast culture, which can be due to reactivation of the telomerase gene in somatic cells and indicates the possibility of prolonging the life span of a cell population [33].…”

Section: The Mechanism Of Action Of Short Sequence Peptidesmentioning

confidence: 99%

Short peptide sequences: current knowledge and future prospects

Nasadyuk¹

2021

Ukr.Biochem.J.

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According to modern knowledge, the biological effect of many peptides is mediated by their shortchain fragments -oligopeptides -ranging from 2 to 20 amino acids and the activity of short peptides often significantly exceeds the activity of the peptide precursor. Aim of the review was to summarize the uptodate data on the stability of short peptide sequences, mechanisms of cell penetration, interaction with cell receptors, biological effects and approaches to clinical application. Stability of short peptides is mediated by their structure and molecular weight. Some di-/tripeptides were reported to be able to permeate through intestinal membranes in their intact forms via peptide transporter systems, while others are vulnerable to protease degradation. although pinocytosis is presumed to be the main mechanism how short peptide sequences enter the cell, some lipophilic oligopeptides were shown to penetrate the cell membrane by the same mechanism as steroid or thyroid hormones and specific extracellular receptors were also described. Low-weighing oligopeptides realize their effect on the cell, chromosomal, genome and molecular levels. The advantages of oligopeptides include oral availability (for low weight compounds), low immunogenicity, high tissue specificity, faster biological effect, better cost efficiency and environmental friendliness of their synthesis. Hence, short peptide sequences are regarded as promising candidates for pharmacotherapy, cell cultures and drug delivery purposes.

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Strategy for the Biosynthesis of Short Oligopeptides: Green and Sustainable Chemistry

Cited by 11 publications

References 119 publications

New Cytotoxic γ-Lactam Alkaloids from the Mangrove-Derived Fungus Talaromyces hainanensis sp. nov. Guided by Molecular Networking Strategy

New Cytotoxic γ-Lactam Alkaloids from the Mangrove-Derived Fungus Talaromyces hainanensis sp. nov. Guided by Molecular Networking Strategy

Cyclic Dipeptides: The Biological and Structural Landscape with Special Focus on the Anti-Cancer Proline-Based Scaffold

Short peptide sequences: current knowledge and future prospects

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