海洋细菌NJ6-3-1次级代谢产物化学成分的分离与鉴定Isolation and identification of the secondary metabolites from marine bacteria NJ6-3-1
王彧博;郑立;李文;裴月湖;
WANG Yu-bo1,ZHENG Li2,LI Wen3,PEI Yue-hu1(1.School of Traditional Chinese Materia Medica,Shenyang Pharmaceutical University,Shenyang 110016,China;2.Qingdao Key Laboratory of Analytical Technology Development and Standardization of Chinese Medicines,First Institute of Oceanography,State Oceanic Administration,Qingdao 266061,China;3.The Test Center for Analysis,Shenyang Pharmaceutical University,Shenyang 110016,China)
摘要(Abstract):
目的研究海洋细菌NJ6-3-1次级代谢产物,以期得到有活性的先导化合物。方法采用硅胶柱色谱、凝胶柱色谱、HPLC等方法进行分离纯化,通过理化性质和波谱手段分析确定化合物的结构。结果从海洋细菌NJ6-3-1的乙酸乙酯萃取物中分离得到15个化合物,分别为环(色-脯)二肽(cyclo(Trp-Pro),1)、环(甘-脯)二肽(cyclo(Gly-Pro),2)、环(甘-苯丙)二肽(cyclo(Gly-Phe),3)、环(丙-苯丙)二肽(cylo(Ala-Phe),4)、环(酪-苯丙)二肽(cyclo(Tyr-Phe),5)、环(酪-脯)二肽(cy-clo(Tyr-Pro),6)、环(4-羟基-脯氨酸-苯丙氨酸)(cyclo(4-hydroxyl-Pro-Phe),7)、环(4-羟基-脯氨酸-亮氨酸)(cyclo(4-hydroxyl-Pro-Leu),8)、环(酪-亮)二肽(cyclo(Tyr-Leu),9)、环(丙-亮)二肽(cyclo(Ala-Leu),10)、环(甘-亮)二肽(cyclo(Gly-Leu),11)、环(丙-缬)二肽(cyclo(Ala-Val),12)、异光黄素(isolumichrome,13)、胸腺嘧啶(thymine,14)、尿嘧啶(uracil,15)。结论化合物115均为首次从海洋细菌NJ6-3-1次级代谢物中分离得到。
Objective To study the chemical constituents from marine bacteria NJ6-3-1.Methods The compounds from the ethyl acetate extracts were isolated by silica gel column,Sephadex LH-20 column and HPLC,and their structures were identified by 1H-NMR,13C-NMR and comparison of chemical and physical data with authentic samples reported in literatures.Results Fifteen compounds were isolated from the ethyl acetate extracts of marine bacteria NJ6-3-1.They were identified as cyclo(Trp-Pro)(1),cyclo(Gly-Pro)(2),cyclo(Gly-Phe)(3),cylo(Ala-Phe)(4),cyclo(Tyr-Phe)(5),cyclo(Tyr-Pro)(6),cyclo(4-hydroxyl-Pro-Phe)(7),cyclo(4-hydroxyl-Pro-Leu)(8),cyclo(Tyr-Leu)(9),cyclo(Ala-Leu)(10),cyclo(Gly-Leu)(11),cyclo(Ala-Val)(12),isolumichrome(13),thymine(14),uracil(15).Conclusions All of the compounds are obtained from marine bacteria NJ6-3-1 for the first time.
关键词(KeyWords):
海洋细菌;乙酸乙酯萃取物;化学成分;结构鉴定
marine bacteria;ethyl acetate extract;chemical constituent;structure identification
基金项目(Foundation): 国家“863”项目(2007AA09Z413,2007AA09Z435);; 国家自然科学基金(40776098,20602009)
作者(Authors):
王彧博;郑立;李文;裴月湖;
WANG Yu-bo1,ZHENG Li2,LI Wen3,PEI Yue-hu1(1.School of Traditional Chinese Materia Medica,Shenyang Pharmaceutical University,Shenyang 110016,China;2.Qingdao Key Laboratory of Analytical Technology Development and Standardization of Chinese Medicines,First Institute of Oceanography,State Oceanic Administration,Qingdao 266061,China;3.The Test Center for Analysis,Shenyang Pharmaceutical University,Shenyang 110016,China)
DOI: 10.14066/j.cnki.cn21-1349/r.2010.05.020
参考文献(References):
- [1]李大志,韩宝芹.海洋细菌活性代谢产物的研究进展[J].中国海洋药物杂志,2006,25(5):51-55.
- [2]赵文英,朱庆书,顾谦群.海洋来源真菌烟曲霉(As-pergillus fumigatus)次级代谢产物研究(II)[J].青岛科技大学学报:自然科学版,2007,28(5):390-393.
- [3]石瑛,田黎,裴月湖,等.海洋放线菌Micromonospo-rasp.与细菌Oceanospirillumsp.发酵液中化学成分的研究[J].中国海洋药物杂志,2006,25(1):6-10.
- [4]KENNETH D K,DAVID H M.Conformations of cy-clic peptides.the folding of cyclic dipeptides contai-ning an aromatic side chain[J].J Am Chem Soc,1967,89(24):6193-6200.
- [5]吴雄宇,林永成,冯爽,等.南海红树林内生真菌1356#代谢产物的研究[J].热带海洋学报,2001,20(4):80-85.
- [6]王双明,谭宁华,杨亚滨,等.三七环二肽成分[J].天然产物研究与开发,2004,16(5):383-386.
- [7]李德海,顾谦群,朱伟明,等.海洋放线菌11014中抗肿瘤活性成分的研究Ⅰ.环二肽[J].中国抗生素杂志,2005,30(8):449-452.
- [8]熊江,周俊,戴好富,等.多蕊商陆的化学成分[J].云南植物研究,2001,24(3):401-405.
- [9]向兰,郭东晓,鞠瑞,等.马齿苋中环二肽成分研究[J].中草药,2007,38(11):1622-1625.
- [10]李春远,陈敏,丁唯嘉,等.一株南海木榄内生真菌(Gloesporiumsp.)代谢产物的研究[J].华南农业大学学报,2008,29(1):122-124.
- [11]李莉娅,邓志威,林文翰,等.中国南海海绵Cin-achyrella australiensis化学成分研究[J].北京大学学报:医学版,2004,36(1):12-17.
- [12]陈光英,朱峰,林永成,等.南海红树内生真菌1947号次级代谢产物的研究[J].化学研究与应用,2007,19(1):98-99.
- 王彧博
- 郑立
- 李文
- 裴月湖
WANG Yu-bo1- ZHENG Li2
- LI Wen3
- PEI Yue-hu1(1.School of Traditional Chinese Materia Medica
- Shenyang Pharmaceutical University
- Shenyang 110016
- China
- 2.Qingdao Key Laboratory of Analytical Technology Development and Standardization of Chinese Medicines
- First Institute of Oceanography
- State Oceanic Administration
- Qingdao 266061
- China
- 3.The Test Center for Analysis
- Shenyang Pharmaceutical University
- Shenyang 110016
- China)
- 王彧博
- 郑立
- 李文
- 裴月湖
WANG Yu-bo1- ZHENG Li2
- LI Wen3
- PEI Yue-hu1(1.School of Traditional Chinese Materia Medica
- Shenyang Pharmaceutical University
- Shenyang 110016
- China
- 2.Qingdao Key Laboratory of Analytical Technology Development and Standardization of Chinese Medicines
- First Institute of Oceanography
- State Oceanic Administration
- Qingdao 266061
- China
- 3.The Test Center for Analysis
- Shenyang Pharmaceutical University
- Shenyang 110016
- China)