Antimicrobial Secondary Metabolites from the Seawater-Derived Fungus Aspergillus sydowii SW9

Liu, Yujing; Zhang, Jianlong; Li, Chen; Mu, Xue-Gen; Liu, Xiaoli; Wang, Lei; Zhao, Yancui; Zhang, Peng; Li, Xiaodong; Zhang, Xingxiao

doi:10.3390/molecules24244596

Cited by 16 publications

(10 citation statements)

References 20 publications

(28 reference statements)

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“…An endophytic fungus Aspergillus sp. xy02 associated with the Thai mangrove Xylocarpus moluccensis yielded seven new phenolic bisabolane sesquiterpenoids: (7R,10S)-7,10-epoxysydonic acid (21), (7S,10S)-7,10-epoxysydonic acid (22), (7R,11S)-7,12-epoxysydonic acid (23), (7S,11S)-7,12epoxysydonic acid (24), 7-deoxy-7,14-didehydro-12-hydroxysydonic acid (25), (Z)-7-deoxy-7,8-didehydro-12-hydroxysydonic acid (26), and (E)-7deoxy-7,8-didehydro-12-hydroxy-sydonic acid (27) [20]. Biologically, compounds 22-23, 25, and 27 displayed mild antibacterial activity against Staphylococcus aureus ATCC 25923, with IC 50 values ranging from 31.5 to 41.9 µM [20].…”

Section: Sesquiterpenesmentioning

confidence: 99%

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Jiang

Guo

et al. 2020

Marine Drugs

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Marine-derived fungi are a significant source of pharmacologically active metabolites with interesting structural properties, especially terpenoids with biological and chemical diversity. In the past five years, there has been a tremendous increase in the rate of new terpenoids from marine-derived fungi being discovered. In this updated review, we examine the chemical structures and bioactive properties of new terpenes from marine-derived fungi, and the biodiversity of these fungi from 2015 to 2019. A total of 140 research papers describing 471 new terpenoids of six groups (monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, and meroterpenes) from 133 marine fungal strains belonging to 34 genera were included. Among them, sesquiterpenes, meroterpenes, and diterpenes comprise the largest proportions of terpenes, and the fungi genera of Penicillium, Aspergillus, and Trichoderma are the dominant producers of terpenoids. The majority of the marine-derived fungi are isolated from live marine matter: marine animals and aquatic plants (including mangrove plants and algae). Moreover, many terpenoids display various bioactivities, including cytotoxicity, antibacterial activity, lethal toxicity, anti-inflammatory activity, enzyme inhibitor activity, etc. In our opinion, the chemical diversity and biological activities of these novel terpenoids will provide medical and chemical researchers with a plenty variety of promising lead compounds for the development of marine drugs.

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Section: Sesquiterpenesmentioning

confidence: 99%

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Jiang

Guo

et al. 2020

Marine Drugs

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“…Liu et al [29] recently (2019) detected a new antimicrobial quinazoline in Aspergillus sydowii SW9, living in China's seawater. They named the compound 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin- Oxysporizoline (21) was discovered by Nenkep et al (2016) [27] in the marine fungus F. oxysporum in Suncheon Bay, Korea.…”

Section: Quinazolinesmentioning

confidence: 99%

“…Liu et al [29] recently (2019) detected a new antimicrobial quinazoline in Aspergillus sydowii SW9, living in China's seawater. They named the compound 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin-one (23) and it showed antibacterial inhibition against both Gram + and Gram − bacterial strains.…”

Section: Quinazolinesmentioning

confidence: 99%

“…On the other hand, self-condensation of anthranilic acid and chemical synthesis of polycyclic quinazoline derivatives like oxysporizoline complexed with metals were reported, and the latter implied several interesting bioactivities [91]. Another novel quinazoline alkaloid is 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolinone (23), which only differs from the co-discovered 2-(4-hydroxybenzoyl)-4(3H)-quinazolinone through an N-acetyl moiety [29]. The latter was discovered in 2011 [92] and its proposed biogenetic origin starts with l-tyrosine [93].…”

Section: Quinazolinesmentioning

confidence: 99%

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Alkaloids from Marine Fungi: Promising Antimicrobials

et al. 2020

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Resistance of pathogenic microorganisms against antimicrobials is a major threat to contemporary human society. It necessitates a perpetual influx of novel antimicrobial compounds. More specifically, Gram− pathogens emerged as the most exigent danger. In our continuing quest to search for novel antimicrobial molecules, alkaloids from marine fungi show great promise. However, current reports of such newly discovered alkaloids are often limited to cytotoxicity studies and, moreover, neglect to discuss the enigma of their biosynthesis. Yet, the latter is often a prerequisite to make them available through sufficiently efficient processes. This review aims to summarize novel alkaloids with promising antimicrobial properties discovered in the past five years and produced by marine fungi. Several discovery strategies are summarized, and knowledge gaps in biochemical production routes are identified. Finally, links between the structure of the newly discovered molecules and their activity are proposed. Since 2015, a total of 35 new antimicrobial alkaloids from marine fungi were identified, of which 22 showed an antibacterial activity against Gram− microorganisms. Eight of them can be classified as narrow-spectrum Gram− antibiotics. Despite this promising ratio of novel alkaloids active against Gram− microorganisms, the number of newly discovered antimicrobial alkaloids is low, due to the narrow spectrum of discovery protocols that are used and the fact that antimicrobial properties of newly discovered alkaloids are barely characterized. Alternatives are proposed in this review. In conclusion, this review summarizes novel findings on antimicrobial alkaloids from marine fungi, shows their potential as promising therapeutic candidates, and hints on how to further improve this potential.

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“…A literature retrieval discovered that 52 out of 59 new compounds were isolated from the marine-derived Aspergillus sydowii fungus. The bisabolane-type sesquiterpenoids [ 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ], xanthones [ 18 , 23 , 25 ], diphenyl ethers [ 20 , 26 , 27 , 28 ], and diketopiperazine alkaloids [ 29 , 30 , 31 ] were common secondary metabolites of the A. sydowii , some of which exhibited a wide range of pharmacological activities. To date, only three undescribed polyketides, namely asperentin B [ 32 ], 2,3,5-trimethyl-6-(3-oxobutan-2-yl)-4H-pyran-4-one, and (2 R )-2,3-dihydro-7-hydroxy-6,8-dimethyl-2-[( E )-propl-enyl] chromen-4-one [ 33 ], have been reported from the deep-sea-derived A. sydowii .…”

Section: Introductionmentioning

confidence: 99%

New Monoterpenoids and Polyketides from the Deep-Sea Sediment-Derived Fungus Aspergillus sydowii MCCC 3A00324

et al. 2020

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Chemical study of the secondary metabolites of a deep-sea-derived fungus Aspergillus sydowii MCCC 3A00324 led to the isolation of eleven compounds (1–11), including one novel (1) and one new (2) osmane-related monoterpenoids and two undescribed polyketides (3 and 4). The structures of the metabolites were determined by comprehensive analyses of the NMR and HRESIMS spectra, in association with quantum chemical calculations of the 13C NMR, ECD, and specific rotation data for the configurational assignment. Compound 1 possessed a novel monoterpenoid skeleton, biogenetically probably derived from the osmane-type monoperpenoid after the cyclopentane ring cleavage and oxidation reactions. Additionally, compound 3 was the first example of the α-pyrone derivatives bearing two phenyl units at C-3 and C-5, respectively. The anti-inflammatory activities of 1–11 were tested. As a result, compound 6 showed potent inhibitory nitric oxide production in lipopolysaccharide (LPS)-activated BV-2 microglia cells with an inhibition rate of 94.4% at the concentration of 10 µM. In addition, a plausible biosynthetic pathway for 1 and 2 was also proposed.

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Antimicrobial Secondary Metabolites from the Seawater-Derived Fungus Aspergillus sydowii SW9

Cited by 16 publications

References 20 publications

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

A Review of Terpenes from Marine-Derived Fungi: 2015–2019

Alkaloids from Marine Fungi: Promising Antimicrobials

New Monoterpenoids and Polyketides from the Deep-Sea Sediment-Derived Fungus Aspergillus sydowii MCCC 3A00324

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