New bioactive pyrrospirones C−I from a marine-derived fungus Penicillium sp. ZZ380

Song, Tengfei; Chen, Mengxuan; Chai, Weiyun; Zhang, Zhizhen; Lian, Xiao-Yuan

doi:10.1016/j.tet.2018.01.015

Cited by 46 publications

(62 citation statements)

References 30 publications

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“…Pyrrospirone C-F and I (3-7) were discovered by [16] in the fungus Penicillium sp. ZZ380, which was isolated from a wild crab (Pachygrapsus crassipes) living on the seaside rocks of Putuo Mountain (Zhoushan, China).…”

Section: Indolesmentioning

confidence: 99%

“…In 2019, two new antimicrobial indoles were discovered by Guo et al [24], called penijanthine C and D (16)(17). They were detected in Penicillium janthinellum, living in the sediments of the Bohai Sea, China.…”

Section: (Di)terpenoid Indolesmentioning

confidence: 99%

“…A third type of pyrrolidine alkaloids discovered since 2015, the pyrrospirones, contains a 13-membered macroether ring composed of decahydrofluorene, para-cyclophane, and pyrrolidinone [18]. The biosynthesis of pyrrospirones C-F and I (3-7) is assumed to be derived from GKK1032A 1 or GKK1032A 2 through oxidation of the vinyl group and electrophilic cyclization of the resulting epoxide [16]. In 2018, penicipyrrodiether A (8), a novel adduct of GKK1032A 2 , was discovered in the extracts of Penicillium sp.…”

Section: Pyrrolidinesmentioning

confidence: 99%

“…Penijanthines C and D (16)(17) were only tested for their anti-Vibrio activity, to assess their potential as vibriosis moderators in marine cultures. It was seen that penijanthine C displayed a higher antibacterial activity against these species, than did D, suggesting that the acetoxy group (blue in Figure 10D), situated at C-7, may be an inhibitor of anti-Vibrio activity.…”

Section: Structure-activity Analysismentioning

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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Section: Indolesmentioning

confidence: 99%

Section: (Di)terpenoid Indolesmentioning

confidence: 99%

Section: Pyrrolidinesmentioning

confidence: 99%

Section: Structure-activity Analysismentioning

confidence: 99%

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Alkaloids from Marine Fungi: Promising Antimicrobials

et al. 2020

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“…Compound 151 showed potent cytotoxicity against four glioma cells, with IC 50 values of 1.06-8.52 µM, while being devoid of antibacterial activity [128]. PTAs 147-150, 152-153, and 155 showed moderate cytotoxicity, with IC 50 values of 7.44-29.10 µM, and antibacterial activity against both MRSA and E. coli, with MICs of 2.0-34.0 µg/mL (147, 150, and 153: MICs = 2.0-5.0 µg/mL)[127,128]. It is worth noting that 155 was the first example of a hybrid of phenol A fused to the GKK1032 skeleton via the addition of a five-membered ether ring and displayed anti-MRSA activity (MIC = 5.0 µg/mL)[128].…”

mentioning

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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