Meroditerpene pyrone, tryptoquivaline and brasiliamide derivatives from the fungus Neosartorya pseudofischeri

Paluka, Jakkapat; Kanokmedhakul, Kwanjai; Soytong, Mayamor; Soytong, Kasem; Kanokmedhakul, Somdej

doi:10.1016/j.fitote.2019.104257

Cited by 16 publications

(26 citation statements)

References 18 publications

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“…In this study, bioactive secondary metabolites were isolated from the gorgonian coralderived fungus Aspergillus hiratsukae SCSIO 7S2001: six new α-pyrone meroterpenoid chevalones H-M (1-6), together with six known compounds (7)(8)(9)(10)(11)(12). The absolute configurations of the new compounds were deduced by combining the NOE spectrum, X-ray single crystal diffraction, and ECD spectra.…”

Section: Discussionmentioning

confidence: 99%

“…chevalones H-M (1-6), together with the six known compounds neoechinulin A (7) [9], echinuline (8) [10], isorugulosuvine (9) [11], cyclo(L-Phe-L-Val) (10) [12], trans-cinnamic acid (11) [13], and N-phenethylacetamide (12) [14], by comparison with the reported literature data (Figure 1). Herein, we report the isolation, structural elucidation and bioactivities of these compounds.…”

Section: Introductionmentioning

confidence: 91%

“…Chevalone C was found to show synergism with doxorubicin in A549 cells [5], and its acetylated analog also had certain cytotoxic activity against tumor cells [6]. In addition, chevalones F and G were both isolated by Paluka, but neither of them showed activity [7,8].…”

Section: Introductionmentioning

confidence: 99%

“…Recently, we conducted NMR data analysis on the pretreated crude extracts of marinederived fungal secondary metabolites and found that the metabolites of the coral-derived fungus Aspergillus hiratsukae SCSIO 7S2001 contained NMR signals with high similarity to chevalone C [1]. After further investigation of secondary metabolites of the fungus Aspergillus hiratsukae SCSIO 7S2001, we isolated six new α-pyrone meroterpenoid chevalones H-M (1-6), together with the six known compounds neoechinulin A (7) [9], echinuline (8) [10], isorugulosuvine (9) [11], cyclo(L-Phe-L-Val) (10) [12], trans-cinnamic acid (11) [13], and N-phenethylacetamide (12) [14], by comparison with the reported literature data (Figure 1). Herein, we report the isolation, structural elucidation and bioactivities of these compounds.…”

Section: Introductionmentioning

confidence: 99%

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Chevalones H–M: Six New α-Pyrone Meroterpenoids from the Gorgonian Coral-Derived Fungus Aspergillus hiratsukae SCSIO 7S2001

et al. 2022

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Six new α-pyrone meroterpenoid chevalones H–M (1–6), together with six known compounds (7–12), were isolated from the gorgonian coral-derived fungus Aspergillus hiratsukae SCSIO 7S2001 collected from Mischief Reef in the South China Sea. Their structures, including absolute configurations, were elucidated on the basis of spectroscopic analysis and X-ray diffraction data. Compounds 1–5 and 7 showed different degrees of antibacterial activity with MIC values of 6.25–100 μg/mL. Compound 8 exhibited potent cytotoxicity against SF-268, MCF-7, and A549 cell lines with IC50 values of 12.75, 9.29, and 20.11 μM, respectively.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Chevalones H–M: Six New α-Pyrone Meroterpenoids from the Gorgonian Coral-Derived Fungus Aspergillus hiratsukae SCSIO 7S2001

et al. 2022

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“…In comparison, kanamycin showed antibacterial activity against B. cereus and B. subtilis with an MIC value of 2.1 µM and gentamicin showed antibacterial activity against E. coli and P. aeruginosa with MIC values of 2.1 and 1.1 µM, respectively. Weak cytotoxicity and antibacterial activities of the known compounds 4-12 have been previously reported [41].…”

Section: Resultsmentioning

confidence: 91%

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

et al. 2021

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Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A – C (1 – 3), together with fourteen known compounds (4 – 17), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1 – 3 were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1 showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC50 values of 7, 11, 10, 12, and 10 µM, respectively. Compounds 1 and 14 showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1 – 3 and 14 showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1 showed weak antibacterial activity against Escherichia coli.

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Non‐Heme Iron Enzymes Catalyze Heterobicyclic and Spirocyclic Isoquinolone Core Formation in Piperazine Alkaloid Biosynthesis

Pham,

Yang,

Liu

et al. 2024

Angewandte Chemie

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We report the discovery and biosynthesis of new piperazine alkaloids‒arizonamides, and their derived compounds‒arizolidines, featuring heterobicyclic and spirocyclic isoquinolone skeletons, respectively. Their biosynthetic pathway involves two crucial non‐heme iron enzymes, ParF and ParG, for core skeleton construction. ParF has a dual function facilitating 2,3‐alkene formation of helvamide, as a substrate for ParG, and oxidative cleavage of piperazine. Notably, ParG exhibits catalytic versatility in multiple oxidative reactions, involving cyclization and ring reconstruction. A key amino acid residue Phe67 was characterized to control the formation of the constrained arizonamide B backbone by ParG.

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Meroditerpene pyrone, tryptoquivaline and brasiliamide derivatives from the fungus Neosartorya pseudofischeri

Cited by 16 publications

References 18 publications

Chevalones H–M: Six New α-Pyrone Meroterpenoids from the Gorgonian Coral-Derived Fungus Aspergillus hiratsukae SCSIO 7S2001

Chevalones H–M: Six New α-Pyrone Meroterpenoids from the Gorgonian Coral-Derived Fungus Aspergillus hiratsukae SCSIO 7S2001

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

Non‐Heme Iron Enzymes Catalyze Heterobicyclic and Spirocyclic Isoquinolone Core Formation in Piperazine Alkaloid Biosynthesis

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