Four Novel Hydropyranoindeno-Derivatives from Marine Fungus Aspergillus versicolor

From the cultured filtrates of fungus Aspergillus versicolor, isolated from marine sponge Xestospongia exigua, four novel secondary metabolites, namely aspergillone 1, aspergillodiol 2, aspergillol 3 and 12-acetyl-aspergillol 4, have been isolated by column chromatographic separation. The structures of all the new compounds are established on the basis of extensive 2D NMR spectroscopy in conjugation with MS, UV spectral analysis. The basic structure pattern of those compounds possessed an hydroindenoisopyran nucleus.

Phenylquinolinones with antitumor activity from the Indian Ocean-derived fungus Aspergillus versicolor Y31-2

Two phenylquinolinones,including one new compound(1) and a previously isolated compound(2),were isolated from the ethyl acetate extracts of the fungus Aspergillus versicolor Y31-2,which was obtained from seawater samples collected from the Indian Ocean.The structures of these compounds were established by spectroscopic analyses.4-(3-Hydroxyphenyl)-3-methoxyquinolin-2(1H)-one(1) exhibited moderate cytotoxicity against MCF-7(human breast carcinoma cell line) and SMMC-7721(human liver cancer cell line) cells with IC_(50) values of 16.6 and 18.2 μmol/L,respectively.To the best of our knowledge,this study represents the first reported account of the isolation of compounds 1 and 2 as the secondary metabolites of the seawater derived fungus Aspergillus versicolor from the Indian Ocean.

Novel Chromone Derivatives from Marine Fungus Aspergillus versicolor Isolated from the Sponge Xestospongia exigua

From the marine sponge Xestospongia exigua, fungal isolates of Aspergillus versicolor (Vuill)Triab were obtained. Isolation and purification of ethyl acetate extracts from culture filtrates of the fungus led to yield six new chromone derivatives namely aspergione A, aspergione B, aspergione C, aspergione D. aspergione E, aspergione F. The structures of all the new compounds were established on the basis of extensive spectroscopy (UV, MS, H-1 and C-13 NMR, COSY, HMQC and HMBC) analysis.

浒苔来源真菌Aspergillus versicolor ZJOU-SKL-02次级代谢产物及其活性研究

目的研究真菌Aspergillus versicolor ZJOU-SKL-02的次级代谢产物及其生物活性。方法利用硅胶柱色谱、薄层色谱(TLC)、高效液相色谱(HPLC)等方法对Aspergillus versicolor ZJOU-SKL-02发酵液进行分离纯化;通过电喷雾质谱(ESI-MS)、核磁共振(NMR)、比旋光、化学合成等手段,并结合文献数据,确定了其产生的化合物结构及绝对构型。对分离得到的化合物进行了抑菌活性和α-葡萄糖苷酶抑制活性的测试。结果分离得到6个二苯醚类化合物Diorcinol B(1)、Diorcinol C(2)、Diorcinol E(3)、Diorcinol J(4)、Diorcinol(5)和methyl diorcinol-4-carboxylate(6)。其中化合物5对铜绿假单胞菌有较强的抑菌活性,MIC值为4μg·m L^-1;化合物6显示出对铜绿假单胞菌(Pseudomonas aeruginosa)和光滑念珠菌(Candida glabrata)有较强的抑菌活性,MIC值分别为4和8μg·mL^-1。化合物3和化合物4具有强的α-葡萄糖苷酶抑制活性,IC50值分别为117.3和237.4μmol·L^-1,优于阳性对照阿卡波糖的IC50255.3μmol·L^-1。结论以上活性化合物可以为抗生素的发现和糖尿病的预防和治疗用药提供活性先导化合物资源。

1株深海来源Aspergillus versicolor(MCCC 3A00937)化学成分及生物活性研究

目的研究1株采自西太平洋海山区深海沉积物中真菌Aspergillus versicolor(MCCC3A00937)的次级代谢产物。方法利用薄层色谱法(TLC)、硅胶柱层析法、SephadexLH-20凝胶柱层析法、中压制备液相色谱法(MPLC)、高效液相色谱法(HPLC)等分离方法对该菌株发酵次级代谢产物进行了分离纯化;通过核磁共振(NMR)、高效液相色谱法耦合质谱分析(LCMS)等现代波谱学方法,并结合相关文献进行数据分析,鉴定化合物结构。结果从真菌Aspergillus versicolor(MCCC3A00937)的代谢产物中共分离得到9个化合物,分别是Averantin(1),Averantin-1'-meether(2),2H-6-O-Methylaverufin(3),6-O-Methylaverufin(4),6,8-di-O-methylnidurufin(5),versicolorin B(6),5-methoxysterigmatocystin(7),Brevianamide F(8),Psychrophilin E(9)。活性测试结果,化合物2对HL-60、BEL-704、HCT-116、A549,HeLa和MCF-7细胞系有一定的抑制作用,IC50分别为10.27、4.74、22.12、16.40、8.92、24.26μmol/L;化合物7对MCF-7细胞系有细胞毒性,IC50为12.25μmol/L。

Antioxidant xanthones and anthraquinones isolated from a marine-derived fungus Aspergillus versicolor

Chemical examination of an EtOAc extract of cultured Aspergillus versicolor fungus from deep-sea sediments resulted in the isolation of four xanthones, eight anthraquinones and five alkaloids, including a new xanthone, oxisterigmatocystin D （1） and a new alkaloid, aspergillusine A （13）. High resolution electron impact mass spectrometry （HR-EI-MS）, FT-IR spectroscopy, and NMR techniques were used to elucidate the structures of these compounds, and the absolute configuration of compound 1 was established by its NMR features and coupling constant. Furthermore, the biosynthesis pathway of these xanthones and anthraquinones were deduced, and their antioxidant activity and cytotoxicity in human cancer cell lines （HTC-8, Bel-7420, BGC-823, A549, and A2780） were evaluated. The trolox equivalent antioxidant capacity （TEAC） assay indicated most of the xanthones and anthraquinones possessing moderate antioxidant activities. The Nrf2-dependent luciferase reporter gene assay revealed that compounds 6, 7, 9, and 12 potentially activated the expression of Nrf2-regulated gene. In addition, compounds 5 and 11 showed weak cytotoxicity on A549 with the ICs0 values of 25.97 and 25.60 gmol·L^-1, respectively.

Secondary metabolites from a deep-sea-derived Aspergillus versicolor F77

Chemical examination of fermentation products of a deep-sea-derived fungus Aspergillus versicolor F77 led to the isolation of two new compounds acetyl-sydonol(1)and 2-hydroxydiorcinol D(2),a new natural product 1-(2,4-dimethoxyphenyl)-1,2-dihydro-3 H-pyrazol-3-one(3),together with four known compounds sydonol(4),(S)-sydonic acid(5),aspergillusene A(6)and diorcinol D(7).Their structures were determined through the extensive spectroscopic analysis and comparison with the reported data in literature.Compound 6 showed moderate NF-κB inhibitory activity.

营养物质协同真菌修复石油烃污染土壤

研究了生物强化结合生物刺激对石油烃污染土壤的修复效果及对修复后土壤pH、土壤呼吸作用的影响。结果表明:向石油烃污染土壤中添加菌液量为20%(w,下同)的真菌杂色曲霉(Aspergillus versicolor)、10%的蔗糖,修复30 d时总石油烃(TPH)降解率达55.63%;添加7%的酒石酸修复30 d时,TPH降解率为42.9%。添加蔗糖和酒石酸修复后,土壤pH均呈下降趋势,土壤CO_(2)释放量均增大。石油烃污染土壤颗粒紧致密实,土壤颗粒之间孔隙被堵塞;经生物修复后土壤孔隙结构明显增大,表面粗糙、疏松,呼吸作用增强。