A new bioactive isocoumarin from the mangrove-derived fungus <i>Penicillium</i> sp. TGM112

Zeng, Wei-Nv; Cai, Jin; Wang, Bin; Chen, Liang‐Yu; Pan, Chen-Xin; Chen, Shi-Ji; Huang, Guo-Lei; Zheng, Cai‐Juan

doi:10.1080/10286020.2021.1952188

Cited by 7 publications

(9 citation statements)

References 21 publications

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“…By comparing physical and spectroscopic data with the literature, the 17 known homologues were identified as (R)-3-(3-hydroxypropyl)-8-hydroxy-3,4-dihydroisocoumarin (7) [35], peniciisocoumarin C (8) [28], 7-hydroxy-3-(3-hydroxypropyl)-8-methoxyisochroman-1-one (9) [34], 5,6-dihydroxy-3-(4-hydroxypentyl)-isochroman-1-one (10) [23], peniciisocoumarin F (11) [28], penicimarin G (12) [16], penicimarin C (13) [36], peniciisocoumarin A (14) [28], peniciisocoumarin B (15) [28], aspergillumarin A (16) [37], penicimarin H (17) [16], peniciisocoumarin D (18) [28], peniciisocoumarin G (19) [28], peniciisocoumarin E (20) [28], penicimarin N (21) [15], 6,8-dihydroxy-3-(2-hydroxypropyl)-7-methyl-1H-isochromen-1one (22) [38] and pestalotiorin (23) [39].…”

Section: Resultsmentioning

confidence: 99%

“…In summary, 23 secondary metabolites, including six new isocoumarin derivative talaromarins A-F (1-6) and 17 known analogues (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23) were obtained from the mangrovederived fungus Talaromyces flavus TGGP35. Compounds 6-11, 17-19 and 22 exerted similar or better antioxidant activity than the positive control trolox (IC 50 = 0.29 mM), with IC 50 values ranging from 0.009 to 0.27 mM.…”

Section: Discussionmentioning

confidence: 99%

“…Hydrolysate of 1 (1a): The antioxidant activity assay was based on the reported methods [15]. The assay was performed on a 96-well microplate, the reaction was initiated by adding 10 µL of sample solution to 200 µL of ABTS working solution.…”

Section: Fermentation Extraction and Isolationmentioning

confidence: 99%

“…[3][4][5][6][7][8]. Among them, isocoumarins are lactone-type derivatives derived from the polyketide pathway [9,10], and they possess a wide range of pharmacological activities such as antibacterial 7-hydroxyoospolactone and parapholactone [11], anti-inflammatory (±)-prunomarin A [12], cytotoxic lunatinin [13], insecticidal peniciisocoumarins A and B, antiplasmodial monocerin [14], antioxidant and α-glucosidase inhibitory penicimarin N [15], brine shrimp (Artemia salina) lethal and broad-spectrum antimicrobial penicimarins G-K [16,17], penicoffrazins B and C [18].…”

Section: Introductionmentioning

confidence: 99%

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Talaromarins A–F: Six New Isocoumarins from Mangrove-Derived Fungus Talaromyces flavus TGGP35

et al. 2022

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Six new isocoumarin derivative talaromarins A-F (1–6), along with 17 known analogues (7–23), were isolated from the mangrove-derived fungus Talaromyces flavus (Eurotiales: Trichocomaceae) TGGP35. Their structures were identified by detailed IR, UV, 1D/2D NMR and HR-ESI-MS spectra. The absolute configurations of new compounds were determined by the modified Mosher’s method and a comparison of their CD spectra with dihydroisocoumarins described in the literature. The antioxidant, antibacterial, anti-phytopathogenic and inhibitory activity against α-glucosidase of all the isolated compounds were tested. Compounds 6–11, 17–19 and 21–22 showed similar or better antioxidant activity than the IC50 values ranging from 0.009 to 0.27 mM, compared with the positive control trolox (IC50 = 0.29 mM). Compounds 10, 18, 21 and 23 exhibited strong inhibitory activities against α-glucosidase with IC50 values ranging from 0.10 to 0.62 mM, while the positive control acarbose had an IC50 value of 0.5 mM. All compounds showed no antibacterial or anti-phytopathogenic activity at the concentrations of 50 μg/mL and 1 mg/mL, respectively. These results indicated that isocoumarins will be useful to developing antioxidants and as diabetes control agents.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Fermentation Extraction and Isolationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Talaromarins A–F: Six New Isocoumarins from Mangrove-Derived Fungus Talaromyces flavus TGGP35

et al. 2022

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“…A wide variety of biological activities have been tested and demonstrated, such as, for example, antioxidant Penicimarin N (1) from mangrove-derived fungus Penicillium sp. [1], zoosporocidal 6,8-dimethoxy-3-methylisocoumarin (2) from terrestrial Streptomyces sp. [2], insecticidal Peniciisocoumarin E (3) against Helicoverpa armiguera [3], a cytotoxic named Beriticulol (4), (12S)-12-hydroxymonocerin (5) from Setosphaeria rostrate [4,5] and anti-inflammatory species (6) from Homalium paniculiflorum [6] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

3-Amino-4-(diphenylamino)-1H-2-benzopyran-1-one

Quiroga-Suavita

Rodríguez

León

2022

Molbank

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Various synthetic methodologies to obtain 3,4-diaminoisocumarin nucleus have been reported and described. However, mechanistic analysis based on experimental evidence is lacking. Herein, we report the synthesis of the novel 3-amino-4-(diphenylamino)-1H-2-benzopyran-1-one using a two-step methodology with a new mechanistic proposal to explain the formation of the latter based on previously reported precursors and the established conditions. This compound was afforded in 80% yield.

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Antibacterial Activity and AbFtsZ Binding Properties of Fungal Metabolites Isolated from Mexican Mangroves

Carrillo-Jaimes,

Fajardo-Hernández,

Hernández-Sedano

et al. 2024

Rev. Bras. Farmacogn.

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Antimicrobial resistance is emerging as a global health challenge that requires immediate and concerted attention. Accordingly, the WHO has issued alerts urging to continue developing antibiotics with novel mechanisms of action toward clinically important pathogens, including Acinetobacter baumannii. In this context, fungi have played a crucial role in the discovery and development of antibiotics. Therefore, in this work, three fungal strains were prioritized based on their metabolic profiles and antibacterial activity against a pan-resistant isolate of A. baumannii, to identify potential antibiotic molecules. Chemical investigation of the selected fungi (mangrove endophytes) led to the isolation of asperazine (1), aurasperone B (2), aurasperone F (3), TMC-256A1 (4), fonsecin B (5), dianhydroaurasperone C (6), aurasperone A (7), pyrophen (8), and penicillide (9). Moreover, an in vitro assay to detect ligands of the filamentous temperature-sensitive mutant Z enzyme of A. baumannii (AbFtsZ), a GTPase that plays a central role in bacterial division, was developed to correlate the antibacterial properties of the isolated molecules to a mechanism of action. Compounds 1–4 and 9 inhibited the growth of A. baumannii. Interestingly, compounds 2, 3, and 5–9 interacted with AbFtsZ1-412, increasing its GTPase activity. Conversely, compound 4 exhibited an outstanding ability to act as an inhibitor of both the enzymatic activity and the growth of the strain under study. Graphical Abstract

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A new bioactive isocoumarin from the mangrove-derived fungus Penicillium sp. TGM112

Cited by 7 publications

References 21 publications

Talaromarins A–F: Six New Isocoumarins from Mangrove-Derived Fungus Talaromyces flavus TGGP35

Talaromarins A–F: Six New Isocoumarins from Mangrove-Derived Fungus Talaromyces flavus TGGP35

3-Amino-4-(diphenylamino)-1H-2-benzopyran-1-one

Antibacterial Activity and AbFtsZ Binding Properties of Fungal Metabolites Isolated from Mexican Mangroves

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