冬虫夏草内生菌Penicillium crustosum的化学成分研究  

Study on the chemical constituents of Penicillium crustosum,an endophytic fungus from Ophiocordyceps sinensis

作　　者：巨凤 罗凡 冯丹 郭大乐 任波[1] 邓赟[1] JU Feng;LUO Fan;FENG Dan;GUO Da-le;REN Bo;DENG Yun(Sichuan Provincial Key Laboratory of Systematic Research,Development and Utilization of Chinese Medical Resources:Ministry of State Key Laboratory Breeding Base,School of Pharmacy,Chengdu University of Traditional Chinese Medicine,Chengdu 611137,China)

机构地区：[1]成都中医药大学药学院,四川省中药资源系统研究与开发利用重点实验-省部共建国家重点实验室培育基地,成都611137

出　　处：《天然产物研究与开发》2021年第7期1147-1155,共9页Natural Product Research and Development

基　　金：国家自然科学基金面上项目(81373961);四川省科技厅省青年科技创新研究团队专项(2016TD0006);中国博士后科学基金(2017M622985);四川省教育厅科研项目(18ZA0191)。

摘　　要：对来源于冬虫夏草中分离得到的内生菌Penicillium crustosum的次级代谢产物和抑菌活性进行研究。采用硅胶柱色谱、MCI柱色谱和半制备HPLC等色谱技术对其进行分离纯化,通过NMR结合质谱进行化学成分鉴定。分离并鉴定16个化合物,分别为:Ac-L-Leu-L-Pro-OCH3(1)、(E)-3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione(2)、(Z)-3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione(3)、cyclopenin(4)、(3S)-1,4-benzodiazepine-2,5-diones(5)、O-acetyl-β-paxitriol(6)、roquefortine C(7)、isoroquefortine C(8)、aflaquinolone G(9)、3-hydroxy-4-phenylquinolin-2(1H)-one(10)、viridicatol(11)、cyclo(Pro-Leu)(12)、N-苯甲基氨基甲酸(13)、(5S,6R,7S,8R)-5-amino-(2Z,4Z)-1,2,3-trihydroxybuta-2,4-dienyloxy-pentane-6,7,8,9-tetraol(14)、2′,4′-二羟基-3′,5′-二甲基苯乙酮(15)、conidiogenone B(16)。分离得到化合物主要为苯二氮卓类、吲哚二萜类和喹诺酮类生物碱。其中化合物1和2为新的天然产物,化合物1~4、6、9、12~14和16为首次从该真菌中分离得到。To investigate the compounds produced by the endophytic fungus Penicillium crustosum from Ophiocordyceps sinensis and their antibacterial activities,16 compounds were isolated and purified by reversed-phase silica gel column chromatography,MCI column chromatography,preparative HPLC,and other methods.Their structures were elucidated on the basis of NMR and MS spectroscopic evidences.The compounds were identified as Ac-L-Leu-L-Pro-OCH3(1),(E)-3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione(2),(Z)-3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione(3),cyclopenin(4),(3S)-1,4-benzodiazepine-2,5-diones(5),O-acetyl-β-paxitriol(6),roquefortine C(7),isoroquefortine C(8),aflaquinolone G(9),3-hydroxy-4-phenylquinolin-2(1H)-one(10),viridicatol(11),cyclo(Pro-Leu)(12),N-(phenylmethyl)carbamic acid(13),(5S,6R,7S,8R)-5-amino-(2Z,4Z)-1,2,3-trihydroxybuta-2,4-dienyloxy-pentane-6,7,8,9-tetraol(14),2′,4′-dihydroxy-3′,5′-dimethylacetophenone(15),and conidiogenone B(16).The compounds isolated are mainly benzodiazepines,indole diterpenes and quinolone alkaloids.Compounds 1 and 2 were isolated as new natural products,and compounds 1-4,6,9,12-14 and 16 were isolated from this strain for the first time.

关 键 词：Penicillium crustosum 化学成分 冬虫夏草 内生菌 

分 类 号：R284.1[医药卫生—中药学]