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化学进展 2008, Vol. 20 Issue (04): 429-440   后一篇

• 综述与评论 •

高通量天然产物化学和毛细管核磁共振探头技术的应用*

胡金锋1,2** Gary R. Eldridge2 余亦华3 Mark O’Neil-Johnson2   

  1. (1.华东师范大学脑功能基因组学教育部重点实验室 上海 200062; 2. 美国红杉科学公司,圣路易斯市 密苏里州 63114; 3.华东师范大学上海市功能磁共振成像重点实验室 上海 200062)

  • 收稿日期:2007-09-23 修回日期:2007-10-19 出版日期:2008-04-24 发布日期:2008-04-24
  • 通讯作者: 胡金锋

High-throughput Natural Product Chemistry Methods and the Application of the Capillary NMR Probe

Hu Jinfeng1,2**; Gary R.Eldridge1;Yu Yihua3;Mark O's Neil-Johnson2

  

  1. (1. Key Laboratory of Brain Functional Genomics of the Ministry of Education, East China Normal University, Shanghai 200062, China; 2. Sequoia Sciences, Inc., Saint Louis, Missouri 63114, USA; 3. Shanghai Key Laboratory of Functional Magnetic Resonance Imaging, East China Normal University, Shanghai 200062, China)
  • Received:2007-09-23 Revised:2007-10-19 Online:2008-04-24 Published:2008-04-24
  • Contact: Hu Jinfeng
介绍了近几年为高通量药物筛选构建大型天然产物样品库的高通量天然产物化学,即多通道平行高效液相制备和平行液质联用分析技术;详细介绍了核磁共振新技术即体积小和质量灵敏度高的毛细管核磁共振探头技术,该探头技术的成功应用使得天然产物样品库中活性化合物的结构鉴定所需样品量降低到前所未有的微克级水平;展望了源于中药的天然产物作为小分子探针开展脑功能方面的化学基因组学研究。
High-throughput natural product chemistry methods, mainly consisting of two parallel multi-channel systems of preparative HPLC and LC-ELSD-MS, have been applied to the generation and analysis of large natural product libraries. The enhancement on mass sensitivity by the low volume capillary NMR probe (CapNMRTM) technology makes the NMR data acquisition, structure elucidation and de-replication on microgram amounts of natural products a reality. This state-of-the-art probe has ushered in a new era in the miniaturization of structure elucidation of natural products using mass-limited material. The perspectives for natural products as small molecular probes in brain functional genomics are briefly provided.

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[ 1 ] Petersen F. Drug Discovery from Natural Sources , 85 Years of Natural Products Research at Novartis. 1 —13
[ 2 ] Newman D J , Cragg G M. J . Nat . Prod. , 2007 , 70 (3) : 461 —477
[ 3 ] Newman D J , Cragg G M, Snader K M. J . Nat . Prod. , 2003 , 66(7) : 1022 —1037
[ 4 ] Newman D J , Cragg G M, Kingston D G. The Practice of Medicinal Chemistry ( ed. Wermuth C G ) . London : Academic Press , 2003. 91
[ 5 ] Roggo S , Ertl P. Drug Discovery from Natural Sources , 85 Years of Natural Products Research at Novartis. 70 —71
[ 6 ] Shu Y Z. J . Nat . Prod. , 1998 , 61 (8) : 1053 —1071
[ 7 ] Henkel T , Brunne R M, Müller H , Reichel F. Angew. Chem.Int . Ed. , 1999 , 38 (5) : 643 —647
[ 8 ] Eldridge G R , Vervoort H C , Lee C M, Cremin P A , Williams C T , Hart S M, Goering M G, O'Neil-Johnson M, Zeng L. Anal .Chem. , 2002 , 74 (16) : 3963 —3971
[ 9 ] Cremin P A , Zeng L. Anal . Chem. , 2002 , 74 (21) : 5492 —5500
[10] Fang L L , Pan J M, Yan B. Biotechnol . Bioeng. , 2000 , 71(2) : 162 —171
[11] Fang L L , Wan M, Pennacchio M, Pan J M. J . Comb. Chem. ,2000 , 2 (3) : 254 —257
[12] Weller H N. Mol . Diversity , 1999 , 4 (1) : 47 —52
[13] Wang T , Zeng L , Cohen J , Kassel D B. Comb. Chem. High T.Scr. , 1999 , 2 (6) : 327 —334
[14] De Biasi V , Haskins N , Organ A , Bateman R , Giles K, Jarvis S.Rapid Commun. Mass Spec. , 1999 , 13 (12) : 1165 —1168
[15] Zeng L , Burton L , Yung K, Shushan B , Kassel D B. J .Chromatogr. A , 1998 , 794 (1/2) : 3 —13
[16] Taylor E W, Qian M G, Dollinger G D. Anal . Chem. , 1998 , 7016) : 3339 —3347
[17] Zeng L , Kassel D B. Anal . Chem. , 1998 , 70 (20) : 4380 —4388
[18] Schultz L , Garr C D , Cameron L M, Bukowski J . Bioorg. Med.Chem. Lett . , 1998 , 8 (17) : 2409 —2414
[19] Weller H N , YoungM G, Michalczyk S J , Reitnauer G H , Cooley R S , Rahn P C , Loyd D J , Fiore D , Fischman S J . Mol .Diversity , 1997 , 3 (1) : 61 —70
[20] Hu J F , Garo E , Yoo H D , Cremin P A , Zeng L , Goering M G,O’Neil-Johnson M, Eldridge G R. Phytochem. Anal . , 2005 , 16(2) : 127 —133
[21] Hu J F , Yoo H D , Williams C T , Garo E , Cremin P A , Zeng L ,Vervoot H C , Lee CM, Hart SM, GoeringM G, O’Neil-Johnson M, Eldridge G R. Planta Med. , 2005 , 71 (2) : 176 —180
[22] Yoo H D , Cremin P A , Zeng L , Garo E , Williams C T , Lee C M, Goering M G, O’Neil-Johnson M, Eldridge G R , Hu J F. J .Nat . Prod. , 2005 , 68 (1) : 122 —124
[23] McNally D J , Aubry A J , Hui J P M, Khieu N H , Whitfield D ,Ewing C P , Guerry P , Brisson J R , Logan S M, Soo E C. J .Bio. Chem. , 2007 , 282 (19) : 14463 —14475
[24] Szantay C , Beni Z , Balogh G, Gati T. TrAC-Trends Anal .Chem. , 2006 , 25 (8) : 806 —820
[25] Kay W, Petersen B O , Duus J O , Perry M B , Vinogradov E.FEBS J . , 2006 , 273 (13) : 3002 —3013
[26] De Swiet T M. J . Magn. Reson. , 2005 , 174 (2) : 331 —334
[27] Lane A N , Arumugam S. J . Magn. Reson. , 2005 , 173 (2) :339 —343
[28] Bradley S A , Paschal J , Kulanthaivel P. Magn. Reson. Chem. ,2005 , 43 (1) : 31 —35
[29] Sigvardson K W, Adams S P , Barnes TB , Blom K F , Fortunak J M, Haas MJ , Reilly KL , Repta A J , Nemeth GA. J . Pharm.Biomed. Anal . , 2002 , 27 (1P2) : 327 —334
[30] Russell D J , Hadden C E , Martin G E , Gibson A A , Zens A P ,Carolan J L. J . Nat . Prod. , 2000 , 63 (8) : 1047 —1049
[31] Bringmann G, Wohlfarth M, Rischer H , Grune M, Schlauer J .Angew. Chem. Int . Ed. , 2000 , 39 (8) : 1464 —1466
[32] Shockcor J P , Wurm R M, Silver I S , Crouch R C , Martin G E.Tetrahedron Lett . , 1994 , 35 (28) : 4919 —4922
[33] Coxon B. Carbohyd. Res. , 2007 , 342 (8) : 1044 —1054
[34] Findeisen M, Brand T , Berger S. Magn. Reson. Chem. , 2007 ,45 (2) : 175 —178
[35] Charlton A J , Donarski J A , Jones S A , May B D , Thompson K C. J . Environ. Monitor. , 2006 , 8 (11) : 1106 —1110
[36] Anklin C , Alemany L B. Magn. Reson. Chem. , 2006 , 44 (3) :230 —240
[37] Pham T N , Kover K E , Jin L , Uhrin D. J . Magn. Reson. ,2005 , 176 (2) : 199 —206
[38] Coxon B. Carbohyd. Res. , 2005 , 340 (10) : 1714 —1721
[39] Losonczi J , Green I. Am. Lab. , 2004 , 36 (1) : 26 —26
[40] Griffin J L , Keun H , Richter C , Moskau D , Rae C , Nicholson J K. Neurochem. Int . , 2003 , 42 (1) : 93 —99
[41] Martin G E , Hadden C E , Russell DJ , Kaluzny B D , Guido J E ,Duholke W K, Stiemsma B A , Thamann TJ , Crouch R C , Blinov K, Elyashberg M, Martirosian E R , Molodtsov S G, Williams A J , Schiff P L. J . Heterocyclic Chem. , 2002 , 39 (6) : 1241 —1250
[42] Rantanen H , Virkki L , Tuomainen P , Kabel M, Schols H ,Tenkanen M. Carbohyd. Polym. , 2007 , 68 (2) : 350 —359
[43] Quemener B , Ordaz-Ortiz J J , Saulnier L. Carbohyd. Res. ,2006 , 341 (11) : 1834 —1847
[44] Yamaji N , Dai L , Sugase K, Andriantsiferana M, Nakajima T ,Iwashita T. Eur. J . Biochem. , 2004 , 271 (19) : 3855 —3864
[45] Li J Y, Harper J K, Grant DM, Tombe B O , Bashyal B , Hess W M, Strobel GA. Phytochemistry , 2001 , 56 (5) : 463 —468
[46] Chauret D C , Durst T , Armason J T , Sanchez-Vindas P , Roman L S , Poveda L , Keifer P A. Tetrahedron Lett . , 1996 , 37 (44) :7875 —7878
[47] Keifer P A , Baltusis L , Rice D M, Tymiak A A , Shoolery J N.J . Magn. Reson. , 1996 , 119 (1) : 65 —75
[48] Manzi A , Salimath P V , Spiro R C , Keifer P A , Freeze H H. J .Bio. Chem. , 1995 , 270 (16) : 9154 —9163
[49] Spraul M, Freund A S , Nast R E , Withers R S , Maas W E ,Corcoran O. Anal . Chem. , 2003 , 75 (6) : 1536 —1541
[50] Lewis R J , Bernstein M A , Duncan S J , Sleigh C J . Magn.Reson. Chem. , 2005 , 43 (9) : 783 —789
[51] Corcoran O , Spraul M. Drug Discovery Today , 2003 , 8 (14) :624 —631
[52] Corcoran O , Spraul M, Hofmann M, Ismail I M, Lindon J C ,Nicholson J K. J . Pharm. Biomed. Anal . , 1997 , 16 (3) : 481 —489
[53] Sidelmann U G, Braumann U , Hofmann M, Spraul M, Lindon J C , Nicholson J K, Hansen S H. Anal . Chem. , 1997 , 69 (4) :607 —612
[54] Olson D L , Norcross J A , O’Neil-Johnson M, Molitor P F ,Detlefsen D J , Wilson A G, Peck T L. Anal . Chem. , 2004 , 76(10) : 2966 —2974
[55] Olson D L , Lacey M E , Sweedler J V. Anal . Chem. , 1998 , 70(3) : 645 —650
[56] Olson D L , Peck T L , Webb A G, Magin R L , Sweedler J V.Science , 1995 , 270 (5244) : 1967 —1970
[57] Lambert M, Wolfender J L , Staerk D , Christensen B ,Hostettmann K, Jaroszewski J W. Anal . Chem. , 2007 , 79 (2) :727 —735
[58] Wolfender J L , Queiroz E F , Hostettmann K. Magn. Reson.Chem. , 2005 , 43 (9) : 697 —709
[59] Jaroszewski J W. Planta Med. , 2005 , 71 (9) : 795 —802
[60] Schroeder F C , Gronquist M. Angew. Chem. Int . Ed. , 2006 , 45(43) : 7122 —7131
[61] Kautz R A , Goetzinger W K, Karger B L. J . Comb. Chem. ,2005 , 7 (1) : 14 —20
[62] Jansma A , Chuan T , Albrecht R W, Olson D L , Peck T L ,Geierstanger B H. Anal . Chem. , 2005 , 77 (19) : 6509 —6515
[63] Hoult D I , Richards R E. J . Magn. Reson. , 1976 , 24 : 71 —85
[64] Peti W, Norcross J , Eldridge G R , O’Neil2Johnson M. J . Am.Chem. Soc. , 2004 , 126 (18) : 5873 —5878
[65] Krishnan V V. J . Magn. Reson. , 2006 , 179 (2) : 294 —298
[66] Hu J F , Garo E , Hough G W, GoeringM G, O’Neil Johnson M,Eldridge G R. Tetrahedron Lett . , 2007 , 48 (33) : 5747 —5749
[67] Hu J F , Garo E , Hough G W, Goering M G, Yoo H D , O’Neil Johnson M, Eldridge G R. J . Chem. Res. , 2007 , (5) : 296 —297
[68] Garo E , Hu J F , GoeringM G, Hough GW, O’Neil-Johnson M,Eldridge G R. J . Nat . Prod. , 2007 , 70 (6) : 968 —973
[69] Hu J F , Patel R , Li B , Garo E , Hough GW, GoeringM G, Yoo H D , O’Neil-Johnson M, Eldridge G R. J . Nat . Prod. , 2007 ,70 (4) : 604 —607
[70] Hu J F , Garo E , Hough GW, GoeringM G, O’Neil-Johnson M,Eldridge G R. J . Nat . Prod. , 2006 , 69 (4) : 585 —590
[71] Hu J F , Garo E , Goering M G, Pasmore M, Yoo H D , Esser T ,Sestrich J , Cremin P A , Hough G W, Perrone P , Lee YS L , Le N T , O'Neil-Johnson M, Costerton J W, Eldridge G R. J . Nat .Prod. , 2006 , 69 (1) : 118 —120
[72] Hu J F , Garo E , Yoo H D , Cremin P A , Goering M G, O'Neil Johnson M, Eldridge G R. Phytochemistry , 2005 , 66 ( 9 ) :1077 —1082
[73] Jiang N , Ou-Yang K Q , Cai S X, Hu Y H , Xu Z L. Acta Pharmacol . Sin. , 2005 , 26 (10) :1181 —1186
[74] Fang L Y, Zhang M C , Li C X, Dong S Z , Hu Y H. Neurosci .Lett . , 2006 , 404 (1/2) : 148 —153
[75] Zheng X X, Hu Y H , Liu J H , Ou-Yang K Q. Bioorg. Med.Chem. Lett . , 2005 , 15 (20) : 4531 —4535
[76] Li X C , Hu Y H. Brain Res. Bull . , 2005 , 66 (2) : 99 —105
[77] Wu P , Hu Y H. Curr. Genomics , 2006 , 7 (5) : 293 —300
[78] Dong S Z , Li C X, Wu P , Tsien J Z , Hu Y H. Eur. J .Neurosci . , 2007 , 26 (1) : 101 —112
[79] Niu W Z , Jiang N , Hu Y H. Anal . Biochem. , 2007 , 362 (1) :126 —135
[80] Li X C , Yang Q X, Hu Y H. Neurosci . Lett . , 2006 , 392 (1/2) : 145 —149

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