1株海绵共生真菌代谢产物的研究Study on metabolites from a sponge-derived fungus
龙海林;李康强;许文东;傅玉萍;
LONG Hai-lin;LI Kang-qiang;XU Wen-dong;FU Yu-ping;National Engineer Research Center for the Modernization of Extraction and Separation of Traditional Chinese Medicine,Guangzhou Hanfang Pharmaceutical Co.,Ltd.;
摘要(Abstract):
综合运用各种色谱分离技术对海绵共生真菌Emericella variecolor的固体大米培养基发酵产物进行化学成分研究,利用各种波谱技术进行化学结构鉴定。结果从该真菌的发酵产物中分离得到6个单体化合物,分别鉴定为(+)-2-acetyl-dihydroterrein(1),(+)-3-acetyl-dihydroterrein(2),anditomin(3),andilesin A(4),andilesin C(5),andilesin B(6)。其中化合物1和2为新化合物。
We have carried out the investigation on a sponge-derived fungus,which was identified as Emericella variecolor from the south sea of China. Two new chemical constituents,( +)-2-acetyl-dihydroterrein( 1) and( +)-3-acetyl-dihydroterrein( 2),with four known compounds,anditomin( 3),andilesin A( 4),andilesin C( 5) and andilesin B( 6),were isolated from this fungus by column chromatography over silica gel,Sephadex LH-20,and ODS. The structures of 1 and 2 were elucidated by spectroscopic methods including NMR,HR-ESI-MS,and CD.
关键词(KeyWords):
海绵共生真菌;Emericella variecolor;化学成分
sponge-derived fungus;Emericella variecolor;chemical constituents
基金项目(Foundation): 广东省省级科技计划项目(2015B020234001)
作者(Authors):
龙海林;李康强;许文东;傅玉萍;
LONG Hai-lin;LI Kang-qiang;XU Wen-dong;FU Yu-ping;National Engineer Research Center for the Modernization of Extraction and Separation of Traditional Chinese Medicine,Guangzhou Hanfang Pharmaceutical Co.,Ltd.;
DOI: 10.19540/j.cnki.cjcmm.2017.0131
参考文献(References):
- [1]Rateb M E,Ebel R.Secondary metabolites of fungi from marine habitats[J].Nat Prod Rep,2011,28(2):290.
- [2]Dyall S D,Brown M T,Johnson P J.Ancient invasions:from endosymbionts to organelles[J].Science,2004,304:253.
- [3]Partida-Martinez L P,Hertweck C.Pathogenic fungus harbours endosymbiotic bacteria for toxin production[J].Nature,2005,437(7060):884.
- [4]Debbab A,Aly A H,Proksch P.Endophytes and associated marine derived fungi ecological and chemical perspectives[J].Fungal Dives,2012,57(1):45.
- [5]Li C,Zhu T J,Ding Y Q.Sorbiterrin A,a novel sorbicillin derivative with cholinesterase inhibition activity from the marine-derived fungus Penicillium terrestre[J].Tetrahedron Lett,2012,53(3):325.
- [6]Mitova M,Popov S,Rosa S D.Cyclic peptides from a ruegeria strain of bacteria associated with the sponge Suberites domuncula[J].J Nat Prod,2004,67(7):1178.
- [7]Bringmann G,Lang G,Steffens S,et al.Evariquinone,isoemericellin,and stromemycin from a sponge derived strain of the fungus Emericella variecolor[J].Phytochemistry,2003,63:437.
- [8]Wei H,Itoh T,Kinoshita M,et al.Cytotoxic sesterterpenes,6-epiophiobolin G and 6-epi-ophiobolin N,from marine derived fungus Emericella variecolor GF10[J].Tetrahedron,2004,60:6015.
- [9]Liangsakul J,Pornpakakul S,Sangvichien E,et al.Emervaridione and varioxiranediol,two new metabolites from the endophytic fungus,Emericella variecolor[J].Tetrahedron Lett,2011,52:6427.
- [10]Adachi H,Doi H,Kasahara Y,et al.Asteltoxins from the entomopathogenic Fungus Pochonia bulbillosa 8-H-28[J].J Nat Prod,2015,78:1730.
- [11]Wu Q,Wu C M,Long H L,et al.Varioxiranols A-G and 19-O-methyl-22-methoxypre-shamixanthone,PKS and hybrid PKS-derived metabolits from a sponge-associated Emericella variecolor fungus[J].J Nat Prod,2015,78:2461.
- [12]Malmstrm J,Christophersen C,Barrero A F,et al.Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor[J].J Nat Prod,2002,65:364.
- [13]Simpson T J.Biosynthesis of highly modified meroterpenoids in aspergillus variecolor.Incorporation of13C-labelled acetates and methionine into anditomin and andilesin C[J].Tetrahedron Lett,1981,22(38):3785.
- [14]Simpson T J,Walkinshaw M D.Anditomin,a new C-25 metabolite from Aspergillus variecolor[J].J C S Chem Comm,1981,1981(17):914.
- [15]Simpson T J.Studies on fungal metabolites.Part 1.The structures of andibenins-A and-C,and andilesins-A,-B,and-C,meroterpenoids from Aspergillus variecolor[J].J Chem Soc,Perkin TransⅠ,1979,10(9):2118.
- [16]John W B,Brent R C,Robert A K,et al.Marine natural products[J].Nat Prod Rep,2014,31:160.
- [17]John W B,Brent R C,Robert A K,et al.Marine natural products[J].Nat Prod Rep,2013,30:237.
- [18]John W B,Brent R C,Robert A K,et al.Marine natural products[J].Nat Prod Rep,2012,29:144.
- [19]Jonathan C M.Marine natural products:sythetic aspects[J].Nat Prod Rep,2013,30:783.
- [20]John W B,Brent R C,Robert A K,et al.Marine natural products[J].Nat Prod Rep,2011,28:196.
- 龙海林
- 李康强
- 许文东
- 傅玉萍
LONG Hai-lin- LI Kang-qiang
- XU Wen-dong
- FU Yu-ping
- National Engineer Research Center for the Modernization of Extraction and Separation of Traditional Chinese Medicine
- Guangzhou Hanfang Pharmaceutical Co.
- Ltd.
- 龙海林
- 李康强
- 许文东
- 傅玉萍
LONG Hai-lin- LI Kang-qiang
- XU Wen-dong
- FU Yu-ping
- National Engineer Research Center for the Modernization of Extraction and Separation of Traditional Chinese Medicine
- Guangzhou Hanfang Pharmaceutical Co.
- Ltd.