New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus

Wu, Jing-Shuai; Shi, Xiaohui; Yao, Guangshan; Shao, Chang‐Lun; Fu, Xiaojian; Zhang, Xiuli; Guan, Hongzai; Wang, Chang‐Yun

doi:10.3390/md18030132

Cited by 24 publications

(22 citation statements)

References 27 publications

(45 reference statements)

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“…The fungus was identified as Aspergillus terreus based on the sequence analysis (GenBank accession no. MK611650) of the ITS region of the rRNA gene, as described previously [ 15 ]. This fungal strain was deposited in the Key Laboratory of Marine Drugs, Ministry of Education of China, School of Medicine and Pharmacy, Ocean University of China, Qingdao, China.…”

Section: Methodsmentioning

confidence: 99%

“…In recent years, during our efforts to explore new bioactive marine natural products [ 9 ], chemical epigenetic manipulation has been applied to marine-derived fungi to mine their potential ability to produce metabolic products [ 9 , 10 , 11 , 12 , 13 , 14 ]. In our previous work, a series of thiodiketopiperazines and 3,4-dihydroisocoumarin derivatives were isolated from the starch liquid culture of A. terreus RA2905 derived from sea hare Aplysia pulmonica [ 15 ]. In the present study, in order to tap the metabolic potential of this fungal strain, chemical epigenetic modifiers were applied to activate its cryptic secondary biosynthetic pathways.…”

Section: Introductionmentioning

confidence: 99%

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Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Shi

Zhang

et al. 2020

Molecules

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Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Shi

Zhang

et al. 2020

Molecules

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“…Emestrins L (235) and M (236), two novel DKPs, were separated from the fungus Aspergillus terreus RA2905, which was obtained from the sea hare Aplysia pulmonica from the Weizhou coral reefs in the South China Sea. Compound 236 showed antifungal activity against P. aeruginosa ATCC 27853 with the MIC value of 64 µg/mL [111].…”

Section: Fungi From Other Originmentioning

confidence: 99%

“…Compound 236 showed antifungal activity against P . aeruginosa ATCC 27853 with the MIC value of 64 μg/mL [ 111 ].…”

Section: Chemical Structures Of Diketopiperazines From Marine Organismsmentioning

confidence: 99%

Structures and Biological Activities of Diketopiperazines from Marine Organisms: A Review

et al. 2021

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Diketopiperazines are potential structures with extensive biological functions, which have attracted much attention of natural product researchers for a long time. These compounds possess a stable six-membered ring, which is an important pharmacophore. The marine organisms have especially been proven to be a wide source for discovering diketopiperazine derivatives. In recent years, more and more interesting bioactive diketopiperazines had been found from various marine habitats. This review article is focused on the new 2,5-diketopiperazines derived from marine organisms (sponges and microorganisms) reported from the secondary half-year of 2014 to the first half of the year of 2021. We will comment their chemical structures, biological activities and sources. The objective is to assess the merit of these compounds for further study in the field of drug discovery.

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“…Fungi of the Aspergillus genus isolated from a marine environment have been proven to be rich sources for discovering new chemical entries with antibacterial and antifungal [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 ], inflammatory [ 19 ], antiviral [ 20 , 21 ], and antitumor [ 22 , 23 ] activities. During our ongoing search for novel bioactive secondary metabolites against bacteria and mycobacteria from marine-derived fungi, the crude extract of the fungus Aspergillus sp.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Secondary Metabolites from Marine-Derived Fungus Aspergillus sp. IMCASMF180035

et al. 2021

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Four new secondary metabolites, including one spiro[anthracenone-xanthene] derivative aspergiloxathene A (1), one penicillide analogue, Δ2′-1′-dehydropenicillide (2), and two new phthalide derivatives, 5-methyl-3-methoxyepicoccone (3) and 7-carboxy-4-hydroxy-6-methoxy-5-methylphthalide (4), together with four known compounds, yicathin C (5), dehydropenicillide (6), 3-methoxyepicoccone (7), 4-hydroxy-6-methoxy-5-methylphthalide (8), were identified from the marine-derived fungus Aspergillus sp. IMCASMF180035. Their structures were determined by spectroscopic data, including high-resolution electrospray ionization mass spectrometry (HRESIMS), 1D and 2D nuclear magnetic resonance (NMR) techniques. Compound 1 was identified as the first jointed molecule by xanthene and anthracenone moieties possessing an unprecedented carbon skeleton with spiro-ring system. All compounds were evaluated activities against Staphylococcus aureus, methicillin resistant S. aureus (MRSA), Escherichia coli, Escherichia faecium, Pseudomonas aeruginosa, and Helicobacter pylori. Compound 1 showed significant inhibitory effects against S. aureus and MRSA, with minimum inhibitory concentration (MIC) values of 5.60 and 22.40 µM. Compounds 2 and 6 exhibited potent antibacterial activities against H. pylori, with MIC values of 21.73 and 21.61 µM, respectively.

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New Thiodiketopiperazine and 3,4-Dihydroisocoumarin Derivatives from the Marine-Derived Fungus Aspergillus terreus

Cited by 24 publications

References 27 publications

Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Structures and Biological Activities of Diketopiperazines from Marine Organisms: A Review

Antibacterial Secondary Metabolites from Marine-Derived Fungus Aspergillus sp. IMCASMF180035

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