Two new hetero-spirocyclic γ-lactam derivatives from marine sediment-derived fungus Aspergillus sydowi D2–6

Ren, Hong; Liu, Rui; Chen, Li; Zhu, Tianjiao; Zhu, Wei; Gu, Qian Qun

doi:10.1007/s12272-010-0401-4

Cited by 33 publications

(37 citation statements)

References 8 publications

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“…Fractionation and multiple steps of SiO 2 and Sephadex LH-20 followed by reversed phase semi-preparative HPLC purification led to the isolation and identification of a new metabolite belonging to the diketopiperazine family named brevianamide X 1 ( Figure 1 ), in addition to the known metabolites brevianamide F 4 , cyclo( L -pro- L -val), cyclo( L -pro- L -ile), cyclo( L -pro- L -phe), cyclo( L -pro- L -leu), fumitremorgin C, spirotryprostatin A, 6-methoxy-spirotryprostatin C (El-Gendy and Rateb, 2015), pseurotin A (Rateb et al, 2013), bis (dethio) bis (methylthio)gliotoxin (Afiyatullov et al, 2005), and azaspirofurans A and B (Ren et al, 2010). These metabolites were identified based on comparing their spectral data with published data.…”

Section: Resultsmentioning

confidence: 99%

Dual Induction of New Microbial Secondary Metabolites by Fungal Bacterial Co-cultivation

et al. 2017

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The frequent re-isolation of known compounds is one of the major challenges in drug discovery. Many biosynthetic genes are not expressed under standard culture conditions, thus limiting the chemical diversity of microbial compounds that can be obtained through fermentation. On the other hand, the competition during co-cultivation of two or more different microorganisms in most cases leads to an enhanced production of constitutively present compounds or an accumulation of cryptic compounds that are not detected in axenic cultures of the producing strain under different fermentation conditions. Herein, we report the dual induction of newly detected bacterial and fungal metabolites by the co-cultivation of the marine-derived fungal isolate Aspergillus fumigatus MR2012 and two hyper-arid desert bacterial isolates Streptomyces leeuwenhoekii strain C34 and strain C58. Co-cultivation of the fungal isolate MR2012 with the bacterial strain C34 led to the production of luteoride D, a new luteoride derivative and pseurotin G, a new pseurotin derivative in addition to the production of terezine D and 11-O-methylpseurotin A which were not traced before from this fungal strain under different fermentation conditions. In addition to the previously detected metabolites in strain C34, the lasso peptide chaxapeptin was isolated under co-culture conditions. The gene cluster for the latter compound had been identified through genome scanning, but it had never been detected before in the axenic culture of strain C34. Furthermore, when the fungus MR2012 was co-cultivated with the bacterial strain C58, the main producer of chaxapeptin, the titre of this metabolite was doubled, while additionally the bacterial metabolite pentalenic acid was detected and isolated for the first time from this strain, whereas the major fungal metabolites that were produced under axenic culture were suppressed. Finally, fermentation of the MR2012 by itself led to the isolation of the new diketopiperazine metabolite named brevianamide X.

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Section: Resultsmentioning

confidence: 99%

Dual Induction of New Microbial Secondary Metabolites by Fungal Bacterial Co-cultivation

et al. 2017

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“…pseurotins D (82) displayed an apomorphine-antagonistic effect [73], as well as antiparasitic and cytotoxicity affects [78], and pseurotins F2 (83) demonstrated apomorphine-antagonistic activity [86] and chitin synthase inhibition [74]. Screening for antitumor agents, the marine-sediment-derived fungus Aspergillus sydowii D2-6 was found to produce two new 3-STAs, named azaspirofurans A and B (84 and 85), which feature a new furan ring instead of the long linear side chain of pseurotin [87]. In vitro cytotoxicity experiments have demonstrated that 85 has moderate cytotoxicity toward A549 HTCL (IC50 = 10 μM) [87].…”

Section: -Spirotetramic Acidsmentioning

confidence: 99%

The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms

Jiang

Chen

et al. 2020

Marine Drugs

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Tetramic acid (pyrrolidine-2,4-dione) compounds, isolated from a variety of marine and terrestrial organisms, have attracted considerable attention for their diverse, challenging structural complexity and promising bioactivities. In the past decade, marine-derived microorganisms have become great repositories of novel tetramic acids. Here, we discuss the biological activities of 277 tetramic acids of eight classifications (simple 3-acyl tetramic acids, 3-oligoenoyltetramic acids, 3-decalinoyltetramic acid, 3-spirotetramic acids, macrocyclic tetramic acids, N-acylated tetramic acids, α-cyclopiazonic acid-type tetramic acids, and other tetramic acids) from marine-derived microbes, including fungi, actinobacteria, bacteria, and cyanobacteria, as reported in 195 research studies up to 2019.

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“…Chiral amino acid and amino esters are important compounds used as precursors in the preparation of various pharmaceutical and agrochemical molecules, particularly chiral γ‐amino acids, γ‐lactams, and δ‐amino alcohols, which are building blocks for pharmaceutical substances in the chemical industry . Moreover, amino acids have important applications in various organic syntheses as chiral starting materials, auxiliaries, polymer sources, and catalysts.…”

Section: Introductionmentioning

confidence: 99%

Asymmetric Synthesis of Chiral γ‐ and δ‐Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst

et al. 2020

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Novel chiral γand δamino esters 2 a-k were synthesized by enantioselective reduction of N-aryl γand δ-imino esters with aryl, substituted aryl, and heteroaryl groups 1 a-k using trichlorosilane activated with optically active N-pivaloyl L-proline I in high yields (50%-98%) with enantioselectivities (10%-84% enantiomeric excess). The structures of the chiral amino esters 2 a-k were clarified by infrared, nuclear magnetic resonance ( 1 H and 13 C) and gas chromatography-mass spectrometry. The enantiomeric excess of these compounds were identified by chiral high-performance liquid chromatography using a Chiralpak ADÀ H column. The highest ee of 84% and highest yield of 98% were found for 2 d.

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Two new hetero-spirocyclic γ-lactam derivatives from marine sediment-derived fungus Aspergillus sydowi D2–6

Cited by 33 publications

References 8 publications

Dual Induction of New Microbial Secondary Metabolites by Fungal Bacterial Co-cultivation

Dual Induction of New Microbial Secondary Metabolites by Fungal Bacterial Co-cultivation

The Biological and Chemical Diversity of Tetramic Acid Compounds from Marine-Derived Microorganisms

Asymmetric Synthesis of Chiral γ‐ and δ‐Amino Esters Using Trichlorosilane Activated with a Lewis Base Catalyst

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