李艳军,李小霞,陈国栋,高昊,郭良栋,姚新生
LI Yan-jun1,LI Xiao-xia1,CHEN Guo-dong1,GAO Hao1,GUO Liang-dong2,YAO Xin-sheng1(1.Institute of Traditional Chinese Medicine and Natural Products

• 1:暨南大学药学院中药及天然药物研究所
• 2:中国科学院微生物研究所真菌学重点实验室

摘要(Abstract)：

目的研究一株地衣内生真菌Sporormiella irregularis(No.71-11-4-1)的次生代谢产物。方法采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、ODS柱色谱以及HPLC等多种色谱手段对其发酵提取物进行分离纯化,并借助光谱学数据对单体化合物进行结构鉴定。结果分离得到9个甾类化合物,分别鉴定为22E-3,7-epoxy-5,10∶8,9-disecoergosta-9(10),22-diene-5,8-dione(1)、22E-5α,6α-ep-oxyergosta-8(14),22-diene-3β,7α-diol(2)、22E-5α,6α-epoxyergosta-8(9),22-diene-3β,7α-diol(3)、22E-7α-methoxy-5α,6α-epoxyergosta-8(14),22-dien-3β-ol(4)、22E-3β-hydroxy-5α,6α-epoxyergosta-22-en-7-one(5)、22E-ergosta-7,22-diene-3β,5α,6β-triol(6)、22E-6β-methoxyergosta-7,22-diene-3β,5α-diol(7)、22E-5α,8α-epidioxyergosta-6,22-dien-3β-ol(8)、22E-ergosta-4,6,8(14),22-tetraen-3-one(9)。结论其中化合物1是新化合物,属于5,10∶8,9二裂甾体;化合物2～9均为首次从Sporormiella属真菌中分离得到。
Objective To study the secondary metabolites of an endolichenic fungal strain Sporormiella irregularis(No.71-11-4-1). Methods The compounds were isolated by various chromatographic techniques and determined by spectroscopic methods. Results Nine steroids were obtained and identified as 22E-3,7-epoxy-5,10∶8,9-disecoergosta-9(10),22-diene-5,8-dione( 1),22E-5α,6α-epoxyergosta-8(14),22-diene-3β,7α-diol( 2),22E-5α,6α-epoxyergosta-8(9),22-diene-3β,7α-diol( 3),22E-7α-methoxy-5α,6α-epoxyergosta-8(14),22-dien-3β-ol( 4),22E-3β-hydroxy-5α,6α-epoxyergosta-22-en-7-one( 5),22E-ergosta-7,22-diene-3β,5α,6β-triol( 6),22E-6β-methoxyergosta-7,22-diene-3β,5α-diol( 7),22E-5α,8α-epidioxyergosta-6,22-dien-3β-ol( 8)and 22E-ergosta-4,6,8(14),22-tetraen-3-one(9). Conclusions Compound 1 is a new 5,10∶8,9-disecosteroid.Compounds 29 are isolated from Sporormiella fungi for the first time.

关键词(KeyWords)： 内生真菌;Sporormiella irregularis;次生代谢产物;甾体;5,10∶8,9二裂甾体;结构鉴定
endolichenic fungi;Sporormiella irregularis;secondary metabolites;steroid;5,10∶8,9-disecoergosta;structure identification

Abstract:

Keywords:

基金项目(Foundation): 国家重点基础研究发展计划项目(973计划,2009CB522300)

作者(Author): 李艳军,李小霞,陈国栋,高昊,郭良栋,姚新生
LI Yan-jun1,LI Xiao-xia1,CHEN Guo-dong1,GAO Hao1,GUO Liang-dong2,YAO Xin-sheng1(1.Institute of Traditional Chinese Medicine and Natural Products

DOI: 10.14066/j.cnki.cn21-1349/r.2012.09.002

参考文献(References)：

• [1]KRUYS A,ERIKSSON O E,WEDIN M.Phylogenet-ic relationships of coprophilous pleosporales(Do-thideomycetes,Ascomycota),and the classification of some bitunicate taxa of unknown position[J].Myco-logical Research,2006,110(5):527-536.
• [2]LORENC L,BONDARENKO L,PAVLOVIC V,et al.Opening of the macrocyclic ring in5,10∶8,9-dise-costeroids(steroklastanes)[J].Helvetica Chimica Ac-ta,1992,75(1):203-209.
• [3]LORENC L,BONDARENKO L,PAVLOVIC V,etal.5,10∶8,9-disecosteroids(steroklastanes):a new type of modified steroids[J].Mihailovic Helvetica Chimica Acta,1989,72(3):608-623.
• [4]MIHAILOVIC M L,LORENC L,PAVLOVIC V,et al.Photochemistry of5,10:8,9-disecosteroidal(3E,9E)-diene-5,8-diones[J].Journal of the Serbian Chemical Society,1989,54(9/10):459-464.
• [5]LORENC L,BONDARENKO L,MIHAILOVIC M L.Transformation of steroidal5α,8α-peroxides to the 14-membered ring containing5,10∶8,9-diseco-steroid derivatives[J].Tetrahedron Letters,1985,26(3):389-392.
• [6]LEE J S,MA C M,PARK D K,et al.Transformation of ergosterol peroxide to cytotoxic substances by rat intestinal bacteria[J].Biological and Pharmaceutical Bulletin,2008,31(5):949-954.
• [7]KWON H C,ZEE S D,CHO S Y,et al.Cytotoxic er-gosterols from Paecilomyces sp.J300[J].Archives of Pharmacal Research,2002,25(6):851-855.
• [8]GRECA M D,FIORENTINO A,MOLINARO A,et al.Steroidal5,6-epoxides from Arum italicum[J].Natural Product Letters,1993,2(1):27-32.
• [9]GAO Hao,HONG Kui,CHEN Guo-dong,et al.New oxidized sterols from Aspergillus awamori and the en-do-boat conformation adopted by the cyclohexene ox-ide system[J].Magnetic Resonance in Chemistry,2010,48(1):38-43.
• [10]GAO Hao,HONG Kui,ZHANG Xue,et al.New ster-yl esters of fatty acids from the mangrove fungus As-pergillus awamori[J].Helvetica Chimica Acta,2007,90(6):1165-1178.
• [11]PICCIALLI V,SICA D.Four new trihydroxylated ste-rols from the sponge Spongionella gracilis[J].Journal of Natural Products,1987,50(5):915-920.
• [12]KAWGISHI H,KATSUMI R,SAZAWA T,et al.Cy-totoxic steroids from the mushroom Agaricus blazei[J].Phytochemistry,1988,27(9):2777-2779.
• [13]HYBELBAUEROVA S,SEJBALA J,DRACINSKY M,et al.Chemical constituents of Stereum subtomen-tosum and two other birch-associated basidiomycetes:an interspecies comparative study[J].Chemistry&Biodiversity,2008,5(5):743-750.
• [14]GAWAS D,GARCIA R,HUCH V,et al.A Highly conjugated dihydroxylated C28steroid from a myx-obacterium[J].Journal of Natural Products,2011,74(5):1281-1283.