Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC–MS/MS-based molecular networking

Han, Yi-Qian; Zhang, Qun; Xu, Weifeng; Hai, Yang; Chao, Rong; Wang, Cuifang; Hou, Xuemei; Wei, Mei‐Yan; Gu, Yu‐Cheng; Wang, Chang‐Yun; Shao, Chang‐Lun

doi:10.1007/s42995-022-00157-8

Cited by 14 publications

(3 citation statements)

References 30 publications

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“…Asperversiamides A-C (21-23, Table 1) are cyclic heptapeptides isolated from a coralderived fungal strain Aspergillus versicolor CHNSCLM-0063 with strong anti-Mycobacterium marinum activity, where asperversiamide B also has mild anti-TB activity [55]. asperheptatides A-D (24-27) are derived from the same fungus, share the same cyclic heptapeptide skeleton as asperversiamides, and have the following amino acid residue sequence: cyclo-Trp1-D-Ala/serine z(Ser)2-Ala/glycine(Gly)/phenylalanine(Phe)3-D/L-valine(Val)4-D-Phe5-Val6-Ala/Ser7 (Table 1) [56,57]. Asperheptatides A-B are structurally closest to asperversiamide B and also exhibit mild anti-TB activity [56].…”

Section: Asperversiamides and Asperheptatidesmentioning

confidence: 99%

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Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Wang,

Gu,

Wang

et al. 2023

Marine Drugs

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In the post-antibiotic era, the rapid development of antibiotic resistance and the shortage of available antibiotics are triggering a new health-care crisis. The discovery of novel and potent antibiotics to extend the antibiotic pipeline is urgent. Small-molecule antimicrobial peptides have a wide variety of antimicrobial spectra and multiple innovative antimicrobial mechanisms due to their rich structural diversity. Consequently, they have become a new research hotspot and are considered to be promising candidates for next-generation antibiotics. Therefore, we have compiled a collection of small-molecule antimicrobial peptides derived from marine microorganisms from the last fifteen years to show the recent advances in this field. We categorize these compounds into three classes—cyclic oligopeptides, cyclic depsipeptides, and cyclic lipopeptides—according to their structural features, and present their sources, structures, and antimicrobial spectrums, with a discussion of the structure activity relationships and mechanisms of action of some compounds.

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Section: Asperversiamides and Asperheptatidesmentioning

confidence: 99%

“…Cyclic depsipeptides derived from marine microorganisms(50)(51)(52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63).…”

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confidence: 99%

Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Wang,

Gu,

Wang

et al. 2023

Marine Drugs

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“…During our previous research on marine fungi for new biological alkaloids, several new diketopiperazine alkaloids with antibacterial, antiviral, and cytotoxic activities were isolated (Han et al 2023 ; Meng et al 2021 ; Li et al 2009 ; Liu et al 2019 ). Among which, three indole diketopiperazines were obtained from the strain of P. brasilianum (HBU-136) (Zhang et al 2019 ).…”

Section: Introductionmentioning

confidence: 99%

Novel anti-inflammatory diketopiperazine alkaloids from the marine-derived fungus Penicillium brasilianum

Zhang,

Du,

Liu

et al. 2024

Appl Microbiol Biotechnol

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Diketopiperazine alkaloids have proven the most abundant heterocyclic alkaloids up to now, which usually process diverse scaffolds and rich biological activities. In our search for bioactive diketopiperazine alkaloids from marine-derived fungi, two novel diketopiperazine alkaloids, penipiperazine A (1) and its biogenetically related new metabolite (2), together with a known analogue neofipiperzine C (3), were obtained from the strain Penicillium brasilianum. Their planar structures and absolute configurations were elucidated by extensive spectroscopic analyses, 13C NMR calculation, Marfey’s, ECD, and ORD methods. Compound 1 featured a unique 6/5/6/6/5 indole-pyrazino-pyrazino-pyrrolo system, and its plausible biogenetic pathway was also proposed. Additionally, compounds 1–3 have been tested for their inflammatory activities. 1 and 2 significantly inhibited the release of NO and the expression of related pro-inflammatory cytokines on LPS-stimulated RAW264.7 cells, suggesting they could be attracting candidate for further development as anti-inflammatory agent. Key points • A novel diketopiperazine alkaloid featuring a unique 6/5/6/6/5 indole-pyrazino-pyrazino-pyrrolo system was isolated from the marine fungus Penicillium brasilianum. • The structure of 1 was elucidated by detailed analysis of 2D NMR data, 13C NMR calculation, Marfey’s, ECD, and ORD methods. • Compounds 1 and 2 significantly inhibited the release of NO and the expression of related pro-inflammatory cytokines on LPS-stimulated RAW264.7 cells. Graphical Abstract

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Natural and synthetic 5‐(3′‐indolyl)oxazoles: Biological activity, chemical synthesis and advanced molecules

Liu,

Jiang,

Sukhbaatar

et al. 2024

Medicinal Research Reviews

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Abstract5‐(3′‐Indolyl)oxazole moiety is a privileged heterocyclic scaffold, embedded in many biologically interesting natural products and potential therapeutic agents. Compounds containing this scaffold, whether from natural sources or synthesized, have demonstrated a wide array of biological activities. This has piqued the interest of synthetic chemists, leading to a large number of reported synthetic approaches to 5‐(3′‐indolyl)oxazole scaffold in recent years. In this review, we comprehensively overviewed the different biological activities and chemical synthetic methods for the 5‐(3′‐indolyl)oxazole scaffold reported in the literatures from 1963 to 2024. The focus of this study is to highlight the significance of 5‐(3′‐indolyl)oxazole derivatives as the lead compounds for the lead discovery of anticancer, pesticidal, antimicrobial, antiviral, antioxidant and anti‐inflammatory agents, to summarize the synthetic methods for the 5‐(3′‐indolyl)oxazole scaffold. In addition, the reported mechanism of action of 5‐(3′‐indolyl)oxazoles and advanced molecules studied in animal models are also reviewed. Furthermore, this review offers perspectives on how 5‐(3′‐indolyl)oxazole scaffold as a privileged structure might be exploited in the future.

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Targeted isolation of antitubercular cycloheptapeptides and an unusual pyrroloindoline-containing new analog, asperpyrroindotide A, using LC–MS/MS-based molecular networking

Cited by 14 publications

References 30 publications

Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Recent Advances in Polypeptide Antibiotics Derived from Marine Microorganisms

Novel anti-inflammatory diketopiperazine alkaloids from the marine-derived fungus Penicillium brasilianum

Natural and synthetic 5‐(3′‐indolyl)oxazoles: Biological activity, chemical synthesis and advanced molecules

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