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Flavichalasines A-M, cytochalasan alkaloids from Aspergillus flavipes.

ABSTRACT: Two new tetracyclic cytochalasans, flavichalasines A and B (1 and 2), three new pentacyclic cytochalasans, flavichalasines C-E (3-5), and eight new tricyclic cytochalasans, flavichalasines F-M (6-13), together with eight known analogues (14-21), were isolated from the solid culture of Aspergillus flavipes. Structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses including 1D, 2D NMR and HRESIMS data. Their absolute configurations were determined by comparison of their experimental ECD with either computed ECD or experimental ECD spectrum of known compound. The structure and absolute configuration of 2 were further determined by X-ray crystallographic diffraction. Flavichalasine A (1) represents the first example of cytochalasan with a terminal double bond at the macrocyclic ring and flavichalasine E (5) is the only cytochalasan with an ?-oriented oxygen-bridge in D ring. These new compounds were evaluated for their cytotoxic activities against seven human cancer cell lines, of which, 6 and 14 displayed moderate inhibitory activities against tested cell lines. In addition, compounds 6 and 14 induced apoptosis of HL60 cells by activation of caspase-3 and degradation of PARP.

SUBMITTER: Wei G

PROVIDER: S-EPMC5304325 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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Flavichalasines A-M, cytochalasan alkaloids from Aspergillus flavipes.

Wei Guangzheng G Tan Dongdong D Chen Chunmei C Tong Qingyi Q Li Xiao-Nian XN Huang Jinfeng J Liu Junjun J Xue Yongbo Y Wang Jianping J Luo Zengwei Z Zhu Hucheng H Zhang Yonghui Y

Scientific reports 20170213

Two new tetracyclic cytochalasans, flavichalasines A and B (1 and 2), three new pentacyclic cytochalasans, flavichalasines C-E (3-5), and eight new tricyclic cytochalasans, flavichalasines F-M (6-13), together with eight known analogues (14-21), were isolated from the solid culture of Aspergillus flavipes. Structures of these new compounds were elucidated on the basis of extensive spectroscopic analyses including 1D, 2D NMR and HRESIMS data. Their absolute configurations were determined by compa ...[more]

PMID: 28205583

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Project description:BackgroundMycosynthesis of silver nanoparticles (SNPs) offers a safe, eco-friendly, and promising alternative technique for large-scale manufacturing. Our study might be the first report that uses mycelial filtrate of an endophytic fungus, Aspergillus flavipes, for SNPs production under optimal conditions as an antimicrobial agent against clinical multidrug-resistant (MDR) wound pathogens.ResultsIn the present study, among four different endophytic fungi isolated from leaves of Lycium shawii, the only one isolate that has the ability to mycosynthesize SNPs has been identified for the first time as Aspergillus flavipes AUMC 15772 and deposited in Genebank under the accession number OP521771. One variable at a time (OVAT) and Plackett Burman design (PBD) were conducted for enhancing the production of mycosynthesized SNPs (Myco-SNPs) through optimization using five independent variables. The overall optimal variables for increasing the mycosynthesis of SNPs from mycelial filtrate of A. flavipes as a novel endophytic fungus were a silver nitrate concentration of 2 mM, a pH of 7.0, an incubation time of 5 days, and a mycelial filtrate concentration of 30% in dark conditions. UV-visible spectroscopy (UV-Vis), Fourier transform infrared spectroscopy (FT-IR), X-ray spectroscopy (XRD), Transmission electron microscopy (TEM), and Selected-Area Electron Diffraction (SAED) patterns were used to characterize Myco-SNPs, which showed the peak of absorbance at 420 nm, and FTIR showed the bands at 3426.44, 2923.30, 1681.85, 1552.64, and 1023.02 cm-1, respectively, which illustrated the presence of polyphenols, hydroxyl, alkene, nitro compounds, and aliphatic amines, respectively. The XRD pattern revealed the formation of Myco-SNPs with good crystal quality at 2θ = 34.23° and 38.18°. The TEM image and SAED pattern show the spherical crystalline shape of Myco-SNPs with an average size of 6.9232 nm. High antibacterial activity of Myco-SNPs was recorded against MDR wound pathogens as studied by minimum inhibitory concentrations ranging from 8 to 32 µg/mL, time kill kinetics, and post-agent effects. Also, in vitro cell tests indicated that Myco-SNPs support the cell viability of human skin fibroblast cells as a nontoxic compound.ConclusionThe obtained results revealed the successful production of Myco-SNPs using the mycelial filtrate of A. flavipes, which may be a promising nontoxic alternative candidate for combating MDR wound pathogens.

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Flavichalasines A-M, cytochalasan alkaloids from Aspergillus flavipes.

Publications

Flavichalasines A-M, cytochalasan alkaloids from Aspergillus flavipes.

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