玄参内生真菌Nigrospora oryzae D7次生代谢产物研究

Secondary metabolites of endophytic fungus Nigrospora oryzae D7 from Scrophularia ningpoensis

目的研究玄参内生真菌Nigrospora oryzae D7的次生代谢产物及生物活性。方法采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱及HPLC进行分离纯化,利用核磁共振谱和质谱等谱学技术对化合物进行结构鉴定。结果从N.oryzae D7培养物的醋酸乙酯萃取物中共分离得到11个化合物,分别鉴定4,5,8-三羟基-6-甲氧基-2-甲基-3-2-丙酰-3,4-二氢萘-1(2H)-酮(1)、(S)-2-甲基-2,3-二氢苯并呋喃-4-羧酸(2)、3-羟基-2-甲氧基-5,6-二甲基苯甲酸(3)、2-乙氧基-3-羟基-5,6-二甲基苯甲酸(4)、2,4-二羟基-3,6-二甲基苯甲醛(5)、2,5-二甲基间苯二酚(6)、2-(4-羟苯基)乙酸乙酯(7)、酪醇(8)、α-acetylorcinol(9)、(20S,22E,24R)-5α,8α-桥二氧-麦角甾烷-6,22-二烯-3β-醇(10)、(3β,5α,6β,22E)-麦角甾-7,22-二烯-3,5,6-三醇(11)。化合物1为新化合物,活性测试结果表明化合物1对人肺癌A549细胞和人乳腺癌MDA-MB-435细胞具有较强的生长抑制活性,IC50分别为(9.25±1.60)、(11.37±2.10)μmol/L;化合物10和11对A549细胞的增殖有一定的抑制活性,IC50分别为(25.23±2.50)、(27.48±1.90)μmol/L。结论化合物1为萘醌类新化合物,命名为稻黑孢醌A;化合物1对A549细胞和MDA-MB-435细胞的增殖有显著的抑制活性。化合物10和11对A549细胞增殖有一定的抑制作用。

Objective To study the secondary metabolites and its biological activities of the endophyties Nigrospora oryzaeD7 derived from the roots of Scrophularia ningpoensis.Methods The secondary metabolites of N.oryzaeD7 were separated and purified by using the chromatographic methods(silica gel,Sephadex LH-20 and HPLC).The structures of all compounds were determined by chemical and spectroscopic methods(NMR,mass spectrometry,etc.).ResultsA total of 11compounds were isolated fromN.oryzaeD7 and identified as 4,5,8-trihydroxy-6-methoxy-2-methyl-3-(2-oxopropyl)-3,4-dihydronaphthalen-1(2H)-one(1),(S)-2-methyl-2,3-dihydrobenzofuran-4-carboxylic acid(2),3-hydroxy-2-methoxy-5,6-dimethylbenzoic acid(3),2-ethoxy-3-hydroxy-5,6-dimethylbenzoic acid(4),2,4-dihydroxy-3,6-dimethyl benzaldehyde(5),2,5-dimethyl resorcinol(6),2-(4-hydroxyphenyl)ethyl acetate(7),tyrosol(8),α-acetylorcinol(9),5α,8α-epidioxy-(20S,22E,24R)-ergosta-6,22-dien-3β-ol(10),(3β,5α,6β,22E)-ergosta-7,22-diene-3,5,6-triol(11),respectively.The results showed that compound1had strong anti-tumor activity against A549 and MDA-MB-435 cell lines with the IC50values of(9.25±1.60)μmol/Land(11.37±2.10)μmol/L,respectively;Compounds 10and 11exhibited moderate antitumor activity with the IC50 values of(25.23±2.50)μmol/Land(27.48±1.90)μmol/L,respectively.ConclusionCompound 1is a new naphthoquinone compound,which is namednaphthspora A.Compound 1 has strong cytotoxicity on the proliferation of lung cancer cell line A549 and breast cancer cell line MDA-MB-435 cell.Compound10and11have moderate inhibitory effect on lung cancer cell line A549.