南海深海沉积环境来源真菌Aspergillus sp. SCSIO F063的次生代谢产物研究
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摘要
目的采用单株菌多次级代谢产物(OSMAC)策略对1株南海深海沉积环境来源真菌的次生代谢产物进行分离、鉴定及活性研究。方法通过改变培养基组成并筛选合适的发酵条件,采用硅胶柱层析、反相ODS柱层析、半制备高效液相等色谱学方法对真菌Aspergillus sp. SCSIO F063的发酵产物进行化学分离,利用NMR、MS等波谱学技术并结合文献进行化合物的结构鉴定,并对化合物进行初步的抗氧化活性测试。结果从菌株SCSIO F063中新增分离鉴定5个单体化合物:6-O-methyl-averythrin(1),(2,4-dichlorophenyl)-2,4-dichlorobenzoate(2),dibutyl phthalate(3),folipastatin(4),di-(2-ethylhexyl)-phthalate(5)。结论改变培养基组成可以刺激该菌株产生不同类型的化合物,化合物1～5为首次从真菌SCSIO F063中分离得到。
Objective Using one strain many compounds strategy to isolate and identify the secondary metabolites of strain Aspergillus sp.SCSIO F063,a deep-sea sediment derived fungus from the South China Sea.Methods By altering the cultivation parameters and screening the fermentation conditions,many different compounds were produced from Aspergillus sp. SCSIO F063.The extracted products were purified by silica gel column,reverse phase ODS column,and semi-preparative HPLC.The isolated compounds were identified by spectroscopic analysis(NMR and MS)as well as comparison with literature.They were screened for antioxidative potency.Results Five compounds were obtained from the ethyl acetate extracts of strain SCSIO F063.Their structures were identified as 6-O-methyl-averythrin(1),(2,4-dichlorophenyl)-2,4-dichlorobenzoate(2),dibutyl phthalate(3),folipastatin(4),di-(2-ethylhexyl)-phthalate(5).Conclusion Using different medium in fermentation of this fungus could result different kinds of secondary metabolites.Compounds 1～5 were isolated from SCSIO F063 for the first time.
Objective Using one strain many compounds strategy to isolate and identify the secondary metabolites of strain Aspergillus sp.SCSIO F063,a deep-sea sediment derived fungus from the South China Sea.Methods By altering the cultivation parameters and screening the fermentation conditions,many different compounds were produced from Aspergillus sp. SCSIO F063.The extracted products were purified by silica gel column,reverse phase ODS column,and semi-preparative HPLC.The isolated compounds were identified by spectroscopic analysis(NMR and MS)as well as comparison with literature.They were screened for antioxidative potency.Results Five compounds were obtained from the ethyl acetate extracts of strain SCSIO F063.Their structures were identified as 6-O-methyl-averythrin(1),(2,4-dichlorophenyl)-2,4-dichlorobenzoate(2),dibutyl phthalate(3),folipastatin(4),di-(2-ethylhexyl)-phthalate(5).Conclusion Using different medium in fermentation of this fungus could result different kinds of secondary metabolites.Compounds 1～5 were isolated from SCSIO F063 for the first time.
引文
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[2]Wang Y T,Xue Y R,Liu C H.A brief review ofbioactive metabolites derived from deep-sea fungi[J].Mar Drugs,2015,13(8):4594-4616.
[3]Skropeta D,Wei L.Recent advances in deep-seanatural products[J].Nat Prod Rep,2014,31(8):999-1025.
[4]Jones E G.Fifty years of marine mycology[J].Fungal Divers,2011,50(1):73-112.
[5]Richards T A,Jones M D,Leonard G,et al.Marine fungi:their ecology and molecular diversity[J].Annu Rev Mar Sci,2012,4(4):495-522.
[6]Niu S,Liu D,Shao Z,et al.Eutypellazines N-S,new thiodiketopiperazines from a deep sea sediment derived fungus Eutypella sp.with anti-VRE activities[J].Tetrahedron Lett,2017,58(38):3695-3699.
[7]Blunt J W,Carroll A R,Copp B R,et al.Marine natural products[J].Nat Prod Rep,2018,35(1):8-53.
[8]Bode H B,Bethe B,H9fs R,et al.Big effects fromsmall changes:possible ways to explore nature'schemical diversity[J].Chem Bio Chem,2002,3(7):619-627.
[9]Liu Y,Li X M,Meng L H,et al.Bisthiodiketopiperazines and acorane sesquiterpenes produced bythe marine-derived fungus Penicillium adametzioides AS-53ondifferent culture media[J].J Nat Prod,2015,78(6):1294-1299.
[10]Luan Y,Wei H,Zhang Z,et al.Eleganketal A,a highly oxygenated dibenzospiroketal from the marine-derived fungus Spicaria elegans KLA03[J].J Nat Prod,2014,77(7):1718-1723.
[11]Lin Z J,Zhu T J,Chen L,et al.Three new aspochalasin derivatives from the marine-derived fungus Spicaria elegans[J].Chinese Chem Lett,2010,21(7):824-826.
[12]Wang F Z,Wei H J,Zhu T J,et al.Three new cytochalasins from the marine-derived fungus Spicaria elegans KLA03by supplementing the cultures with L-and D-tryptophan[J].Chem Biodivers,2011,8(5):887-894.
[13]Huang H B,Wang F Z,Luo M H,et al.Halogenated anthraquinones from the marine-derived fungus Aspergillus sp.SCSIO F063[J].J Nat Prod,2012,75(7):1346-1352.
[14]Yen G C,Chen H Y.Antioxidant activity of various tea extracts in relation to their antimutagenicity[J].J Agric Food Chem,1995,43(1):27-32.
[15]Ebizuka Y,Sankawa U,Shibata S.The constituents of solorina crocea:averythrin 6-monomethyl ether and methyl gyrophorate[J].Phytochemistry,1970,9(9):2061-2063.
[16]卢启洪,徐娟华,赵昱,等.孔石莼化学成分的研究[J].中国药学杂志,2008,43(8):582-584.
[17]孙萌,杨宇萍,李拥军,等.姜炭化学成分的初步研究[J].中药材,2016,39(2):307-311.
[18]Kamano K,Kinoshita-Okami M,Hemmi A,et al.Folipastatin,a new depsidone compound from Aspergillus unguis as an inhibitor of phospholipase A2[J].J Antibiot,2016,69(8):647-651.
[19]Abdel-Sattar E,El-Mekkawy S.New sulphide derivative fromFerula rutabensis[J].Nat Prod Res,2009,23(9):861-865.
[20]张幸,桂春,田新朋,等.海洋放线菌Streptomyces sp.SC-SIO 01681次级代谢产物的研究[J].中国海洋药物,2015,34(6):23-28.