Penicisochromans from the endophytic fungus Penicillium sp. BCC18034

Bunbamrung, Nantiya; Intaraudom, Chakapong; Boonyuen, Nattawut; Rachtawee, Pranee; Laksanacharoen, Pattiyaa; Pittayakhajonwut, Pattama

doi:10.1016/j.phytol.2014.06.018

Cited by 17 publications

(16 citation statements)

References 19 publications

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“…Chlamydocin ( 41 ) was isolated from Diheterospora chlantydosporia [ 39 ] and Penicillium sp. BCC18034 [ 40 ], respectively. This compound showed antimalarial and cytotoxic activities.…”

Section: Cyclic Tetrapeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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Cyclic peptides are cyclic compounds formed mainly by the amide bonds between either proteinogenic or non-proteinogenic amino acids. This review highlights the occurrence, structures and biological activities of fungal cyclic peptides (excluding cyclodipeptides, and peptides containing ester bonds in the core ring) reported until August 2017. About 293 cyclic peptides belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, dodeca-, tetradeca-, and octadecapeptides as well as cyclic peptides containing ether bonds in the core ring have been isolated from fungi. They were mainly isolated from the genera Aspergillus, Penicillium, Fusarium, Acremonium and Amanita. Some of them were screened to have antimicrobial, antiviral, cytotoxic, phytotoxic, insecticidal, nematicidal, immunosuppressive and enzyme-inhibitory activities to show their potential applications. Some fungal cyclic peptides such as the echinocandins, pneumocandins and cyclosporin A have been developed as pharmaceuticals.

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“…Chlamydocin ( 41 ) was isolated from Diheterospora chlantydosporia [ 39 ] and Penicillium sp. BCC18034 [ 40 ], respectively. This compound showed antimalarial and cytotoxic activities.…”

Section: Cyclic Tetrapeptidesmentioning

confidence: 99%

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Wang

Lin

et al. 2017

Molecules

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“…Its molecular formula C 16 , and a methoxy carbon quaternary carbon quaternary carbon (d C 60.9 q). Its 1 H and 13 C NMR spectroscopic data were similar to those of penicisochroman L at the positions of C-1, C-3, C-4, and C-9, indicated that 1 should be a 3-methyl-isocoumarin [20]. This deduction was also supported by the HMBC correlations ( Figure 2) of H-9 (d H 2.28) with C-3 (d C 154.1) and C-4 (d C 101.1), and of H-4 (d H 6.50) with C-3 (d C 154.1), C-9 (d C 18.2), C-4a (d C 129.0), C-5 (d C 131.7), and C-8a (d C 122.1).…”

Section: Resultsmentioning

confidence: 78%

Isocoumarins from the fermentation products of a plant entophytic fungusPenicillium oxalicum

Dang

Zhang

et al. 2015

Journal of Asian Natural Products Research

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Three new isocoumarins, terrecoumarins A-C (1-3), together with six known isocoumarins (4-9) were isolated from the fermentation products of the fungus Penicillium oxalicum 0403. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. The anti-tobacco mosaic virus (anti-TMV) activities of 1-9 were evaluated. The results revealed that compound 1 showed high anti-TMV activity with inhibition rate 25.4 ± 3.5%. Other compounds also showed weak activity with inhibition rate in the range of 11.3-18.9%.

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“…ZJ-68 was purified by repeatedly various chromatography to yield five new ( 1 – 3 , 6 , and 7 ) and nine known compounds ( 4 , 5 , and 8 − 14 ). The known compounds were identical to (−)-penicisochroman A ( 4 ) [13,14,15], (+)-penicisochroman A ( 5 ) [13,14,15], 2-(hydroxymethyl)-3-propylphenol ( 8 ) [16], peniciphenol ( 9 ) [13], penicibenzoxepinol ( 10 ) [17], (−)-brassicadiol ( 11 ) [14,18], (+)-pseudodeflectusin ( 12 ) [14,19], (−)-penicisochroman B ( 13 ) [13,14], and ustusorane A ( 14 ) [14,20] by the comparison of their spectral data (NMR and MS) as well as specific rotation data with those reported.…”

Section: Resultsmentioning

confidence: 99%

New Benzofuranoids and Phenylpropanoids from the Mangrove Endophytic Fungus, Aspergillus sp. ZJ-68

et al. 2019

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Three new benzofuranoids, asperfuranoids A–C (1–3), two new phenylpropanoid derivatives (6 and 7), and nine known analogues (4, 5, and 8–14) were isolated from the liquid substrate fermentation cultures of the mangrove endopytic fungus Aspergillus sp. ZJ-68. The structures of the new compounds were determined by extensive spectroscopic data interpretation. The absolute configurations of 1–3 were assigned via the combination of Mosher’s method, and experimental and calculated electronic circular dichroism (ECD) data. Compounds 4 and 5 were a pair of enantiomers and their absolute configurations were established for the first time on the basis of their ECD spectra aided with ECD calculations. All isolated compounds (1–14) were evaluated for their enzyme inhibitory activity against α-glucosidase and antibacterial activities against four pathogenic bacteria (Staphylococcus aureus, Escherichia coli, Bacillus subtilis, and Pseudomonas aeruginosa). Among them, compound 6 exhibited potent inhibitory activity against α-glucosidase in a standard in vitro assay, with an IC50 value of 12.4 μM, while compounds 8 and 11 showed activities against S. aureus, E. coli, and B. subtilis, with MIC values in the range of 4.15 to 12.5 μg/mL.

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Penicisochromans from the endophytic fungus Penicillium sp. BCC18034

Cited by 17 publications

References 19 publications

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Isocoumarins from the fermentation products of a plant entophytic fungusPenicillium oxalicum

New Benzofuranoids and Phenylpropanoids from the Mangrove Endophytic Fungus, Aspergillus sp. ZJ-68

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