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Search Results (4)

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Keywords = verrucosidin

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11 pages, 2737 KiB  
Article
Verrucosidin Derivatives from the Deep Sea Cold-Seep-Derived Fungus Penicillium polonicum CS-252
by Yanhe Li, Xiaoming Li, Xin Li, Suiqun Yang, Bingui Wang and Honglei Li
Int. J. Mol. Sci. 2022, 23(10), 5567; https://doi.org/10.3390/ijms23105567 - 16 May 2022
Cited by 13 | Viewed by 2517
Abstract
Six novel verrucosidin derivatives, namely, poloncosidins A–F (1–6), together with one known analogue (7), were isolated and identified from the deep-sea-derived fungus Penicillium polonicum CS-252, which was obtained from cold-seep sediments collected in the South China Sea [...] Read more.
Six novel verrucosidin derivatives, namely, poloncosidins A–F (1–6), together with one known analogue (7), were isolated and identified from the deep-sea-derived fungus Penicillium polonicum CS-252, which was obtained from cold-seep sediments collected in the South China Sea at a depth of 1183 m. Their structures were mainly established on the basis of a detailed interpretation of NMR spectroscopic and mass spectrometric data. The relative and absolute configurations of compounds 1–6 were determined by ECD calculations and a DP4+ probability analysis. Compounds 1–5 represent the first examples of verrucosidins with a 2,5-dihydrofuran ring which is uncommon among the known analogues. These compounds exhibited inhibitory activities against several human and aquatic pathogens with MIC values ranging from 4 to 32 μg/mL. Full article
(This article belongs to the Special Issue Marine Natural Products Identified by Molecular Approaches and Human Disease)
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16 pages, 3185 KiB  
Article
Exploring Verrucosidin Derivatives with Glucose-Uptake-Stimulatory Activity from Penicillium cellarum Using MS/MS-Based Molecular Networking
by Junjie Han, Baosong Chen, Rui Zhang, Jinjin Zhang, Huanqin Dai, Tao Wang, Jingzu Sun, Guoliang Zhu, Wei Li, Erwei Li, Xueting Liu, Wenbing Yin and Hongwei Liu
J. Fungi 2022, 8(2), 143; https://doi.org/10.3390/jof8020143 - 30 Jan 2022
Cited by 6 | Viewed by 3668
Abstract
Under the guidance of LC-MS/MS-based molecular networking, seven new verrucosidin derivatives, penicicellarusins A-G (3–9), were isolated together with three known analogues from the fungus Penicillium cellarum. The structures of the new compounds were determined by a combination of [...] Read more.
Under the guidance of LC-MS/MS-based molecular networking, seven new verrucosidin derivatives, penicicellarusins A-G (3–9), were isolated together with three known analogues from the fungus Penicillium cellarum. The structures of the new compounds were determined by a combination of NMR, mass and electronic circular dichroism spectral data analysis. The absolute configuration of penicyrone A (10) was corrected based on X-ray diffraction analyses. Bioactivity screening indicated that compounds 1, 2, and 4 showed much stronger promising hypoglycemic activity than the positive drug (rosiglitazone) in the range of 25–100 μM, which represents a potential new class of hypoglycemic agents. Preliminary structure-activity relationship analysis indicates that the formation of epoxy ring on C6-C7 in the structures is important for the glucose uptake-stimulating activity. The gene cluster for the biosynthesis of 1–12 is identified by sequencing the genome of P. cellarum and similarity analysis with the gene cluster of verrucosidins in P. polonicum. Full article
(This article belongs to the Special Issue Secondary Metabolites from Fungi—in Honour of Prof. Dr. Ji-Kai Liu's 60th Birthday)
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7 pages, 973 KiB  
Article
An Unusual Conformational Isomer of Verrucosidin Backbone from a Hydrothermal Vent Fungus, Penicillium sp. Y-50-10
by Chengqian Pan, Yutong Shi, Bibi Nazia Auckloo, Xuegang Chen, Chen-Tung Arthur Chen, Xinyi Tao and Bin Wu
Mar. Drugs 2016, 14(8), 156; https://doi.org/10.3390/md14080156 - 18 Aug 2016
Cited by 24 | Viewed by 6440
Abstract
A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. [...] Read more.
A new verrucosidin derivative, methyl isoverrucosidinol (1), was isolated from the marine fungus Penicillium sp. Y-50-10, dwelling in sulfur rich sediment in the Kueishantao hydrothermal vents off Taiwan. The structure was established by spectroscopic means including HRMS and 2D-NMR spectroscopic analysis. The absolute configuration was defined mainly by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Among hitherto known compounds with a verrucosidine backbone isolated from natural resource, compound 1 represents the first example of a new conformational isomer of its skeleton, exhibiting antibiotic activity against Bacillus subtilis with MIC value 32 μg/mL. Full article
(This article belongs to the Special Issue Marine Fungal Natural Products)
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11 pages, 216 KiB  
Article
Verrucisidinol and Verrucosidinol Acetate, Two Pyrone-Type Polyketides Isolated from a Marine Derived Fungus, Penicillium aurantiogriseum
by Ke Yu, Biao Ren, Junli Wei, Caixia Chen, Jinsheng Sun, Fuhang Song, Huanqin Dai and Lixin Zhang
Mar. Drugs 2010, 8(11), 2744-2754; https://doi.org/10.3390/md8112744 - 1 Nov 2010
Cited by 35 | Viewed by 10445
Abstract
The new secondary metabolites verrucosidinol (1) and its derivative verrucosidinol acetate (2), together with a potent neurotoxin verrucosidin (3), a congener norverrucosidin (4) and a mixture of two known phytotoxic metabolites terrestric acids (5 [...] Read more.
The new secondary metabolites verrucosidinol (1) and its derivative verrucosidinol acetate (2), together with a potent neurotoxin verrucosidin (3), a congener norverrucosidin (4) and a mixture of two known phytotoxic metabolites terrestric acids (5 and 6), were isolated from the marine derived fungus Penicillium aurantiogriseum. Verrucosidinol has a ring-opened ethylene oxide moiety in the polyene α-pyrone skeleton, and verrucosidinol acetate is its acetate derivative. The chemical structures were determined by comparing with literature data and a combination of spectroscopic techniques, including high resolution mass spectrum and two-dimentional nuclear magnetic resonance spectroscopic analysis. Full article
(This article belongs to the Special Issue Marine Natural Products - Advances in Separation, Characterisation and Chemical Profiling Methodologies)
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