Dipleosporalones A and B, Dimeric Azaphilones from a Marine-Derived <i>Pleosporales</i> sp. Fungus

Cao, Fei; Meng, Zhi-Hui; Wang, Pu; Luo, Du‐Qiang; Zhu, Hua‐Jie

doi:10.1021/acs.jnatprod.0c00132

Cited by 44 publications

(36 citation statements)

References 14 publications

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“…Quantum chemical calculations for 1 – 3 and 5 were carried out on the basis of previous references (gas phase) [ 12 , 13 , 14 ]. Chemical structures of 1 – 3 and 5 were constructed and used for conformational searches using MMFF94S force field by the BARISTA 7.0 software (CONFLEX Corporation Tokyo, Japan).…”

Section: Methodsmentioning

confidence: 99%

Absolute Configurations and Chitinase Inhibitions of Quinazoline-Containing Diketopiperazines from the Marine-Derived Fungus Penicillium polonicum

et al. 2020

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Three new quinazoline-containing diketopiperazines, polonimides A–C (1–3), along with four analogues (4–7), were obtained from the marine-derived fungus Penicillium polonicum. Among them, 2 and 4, 3 and 5 were epimers, respectively, resulting the difficulty in the determination of their configurations. The configurations of 1–3 were determined by 1D nuclear overhauser effect (NOE), Marfey and electron circular dichroism (ECD) methods. Nuclear magnetic resonance (NMR) calculation with the combination of DP4plus probability method was used to distinguish the absolute configurations of C-3 in 3 and 5. All of 1–7 were tested for their chitinase inhibitory activity against OfHex1 and OfChi-h and cytotoxicity against A549, HGC-27 and UMUC-3 cell lines. Compounds 1–7 exhibited weak activity towards OfHex1 and strong activity towards OfChi-h at a concentration of 10.0 μM, with the inhibition rates of 0.7%–10.3% and 79.1%–95.4%, respectively. Interestingly, 1–7 showed low cytotoxicity against A549, HGC-27 and UMUC-3 cell lines, suggesting that good prospect of this cluster of metabolites for drug discovery.

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Section: Methodsmentioning

confidence: 99%

Absolute Configurations and Chitinase Inhibitions of Quinazoline-Containing Diketopiperazines from the Marine-Derived Fungus Penicillium polonicum

et al. 2020

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“…Especially, the experimental ECD spectra of 1-3 were almost identical, indicating that the ECD method had limitations in the assignment of the C-10 absolute configurations for them. Recently, computational methods for atomic chemical shift calculations have been developed and used for the relative configuration identifications of complex natural compounds [9][10][11]. Compounds 1 and 2 are a pair of epimers with more than one stereogenic carbon.…”

Section: Resultsmentioning

confidence: 99%

Setosphlides A–D, New Isocoumarin Derivatives from the Entomogenous Fungus Setosphaeria rostrate LGWB-10

Gao

Wang

Chen

et al. 2021

Nat. Prod. Bioprospect.

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Investigation of the entomogenous fungus Setosphaeria rostrate LGWB-10 from Harmonia axyridis led to the isolation of four new isocoumarin derivatives, setosphlides A–D (1–4), and four known analogues (5–8). Their planar structures and the relative configurations were elucidated by comprehensive spectroscopic methods. The absolute configurations of isocoumarin nucleus for 1–4 were elucidated by their ECD spectra. The C-10 relative configurations for the pair of C-10 epimers (1 and 2) were established by comparing the magnitude of the computed 13C NMR chemical shifts (Δδcalcd.) with the experimental 13C NMR values (Δδexp.) for the epimers. All of the isolated compounds (1–8) were evaluated for their cytotoxicities against four human tumor cell lines MCF-7, MGC-803, HeLa, and Huh-7. Graphic Abstract

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“…Considering the biosynthesis and coisolation of nafuredin A ( 2 ), whose absolute configuration was determined based on asymmetric synthesis ( Takano et al, 2001 ; Zhang et al, 2017 ), the chirality of C-10 and C-16 was determined to be 10 R and 16 S , which was supported by the identical NMR data. Comparing the computed ECD spectra with experimental results is a valid method of assigning the absolute configurations of natural products ( Cao et al, 2020 ). To determine the absolute configuration of the δ -lactone ring in 1 , ECD computations for all B3LYP/6-311+G(d)-optimized conformers (50 structures) were carried out at the B3LYP/6-311++G(2d,p) level, and six structures with relative energy less than 2.5 kcal/mol were obtained.…”

Section: Resultsmentioning

confidence: 99%

Antifungal Nafuredin and Epithiodiketopiperazine Derivatives From the Mangrove-Derived Fungus Trichoderma harzianum D13

et al. 2020

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A new polyketide derivative, nafuredin C (1), a novel heterocyclic dipeptide, trichodermamide G (3), together with four known biogenetically related compounds nafuredin A (2), trichodermamide A (4), aspergillazin A (5), and peniisocoumarin H (6), were isolated from the mangrove-derived fungus Trichoderma harzianum D13. Their structures, including their absolute configurations, were determined by spectroscopic analysis and time-dependent density functional theory-electronic circular dichroism (ECD) calculations. Trichodermamide G was found to be a novel epithiodiketopiperazine derivative with an unprecedented cyclic system containing a sulfur bridge, and nafuredin C represented the third nafuredin derivative of these homologous compounds. The new compound nafuredin C exhibited obvious antifungal activity against Magnaporthe oryzae with a minimum inhibitory concentration (MIC) of 8.63 µM, which is on the same order of magnitude as the positive control carbendazim (MIC = 3.27 µM).

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Dipleosporalones A and B, Dimeric Azaphilones from a Marine-Derived Pleosporales sp. Fungus

Cited by 44 publications

References 14 publications

Absolute Configurations and Chitinase Inhibitions of Quinazoline-Containing Diketopiperazines from the Marine-Derived Fungus Penicillium polonicum

Absolute Configurations and Chitinase Inhibitions of Quinazoline-Containing Diketopiperazines from the Marine-Derived Fungus Penicillium polonicum

Setosphlides A–D, New Isocoumarin Derivatives from the Entomogenous Fungus Setosphaeria rostrate LGWB-10

Antifungal Nafuredin and Epithiodiketopiperazine Derivatives From the Mangrove-Derived Fungus Trichoderma harzianum D13

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