Longphyllinesides A and B: Natural Diels-Alder adducts from Daphniphyllum longeracemosum?

Tetrahedron

Volumn 70, Issue 26, 2014, Pages 4017-4021

  Di, Ying Tong ^a   Wee, Chorng Shin ^b   Li, Chun Shun ^a   Kong, Ning Chuan ^d   Wang, Jun Song ^a   Fang, Xin ^a   Zhu, Hua Jie ^a   Wu, Yun Dong ^b,c   Hao, Xiao Jiang ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^c PEKING UNIVERSITY   (China)

^d YUNNAN ACADEMY OF TOBACCO SCIENCE   (China)

Author keywords

Alkaloid; Biogenetic pathway; Chemical computation; Daphniphyllum longeracemosum; Diels Alderase

Indexed keywords

ALKALOID; LONGPHYLLINESIDE A; LONGPHYLLINESIDE B; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLOADDITION; DAPHNIPHYLLUM LONGERACEMOSUM; DENSITY FUNCTIONAL THEORY; DIELS ALDER REACTION; DRUG ISOLATION; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; MEDICINAL PLANT; MOLECULAR INTERACTION; NUCLEAR OVERHAUSER EFFECT; PLANT LEAF; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

ALNUS; DAPHNIPHYLLUM;

EID: 84901243266     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.04.073     Document Type: Article

References (52)

1. K.N. Houk, J. Gonzalez, and Y. Li Acc. Chem. Res. 28 1995 81 90
2. E.M. Stocking, and R.M. Williams Angew. Chem., Int. Ed. 42 2003 3078 3115
3. H. Oikawa Bull. Chem. Soc. Jpn. 78 2005 537 554
4. W.L. Kelly Org. Biomol. Chem. 6 2008 4483 4493
5. T. Ose, K. Watanabe, M. Yao, M. Honma, H. Oikawa, and I. Tanaka Nature 422 2003 185 189
6. S.M. Ma, J.W.H. Li, J.W. Choi, H. Zhou, K.K.M. Lee, V.A. Moorthie, X.K. Xie, J.T. Kealey, N.A.D. Silva, J.C. Vederas, and Y. Tang Science 326 2009 589 592
7. R.R. Kim, B. Illarionov, M. Joshi, M. Cushman, C.Y. Lee, W. Eisenreich, M. Fischer, and A. Bacher J. Am. Chem. Soc. 132 2010 2983 2990
8. H.J. Kim, M.W. Ruszczycky, S.H. Choi, Y.N. Liu, and H.W. Liu Nature 473 2011 109 112
9. K.C. Nicolaou, N.A. Petasis, and R.E. Zipkin J. Am. Chem. Soc. 104 1982 5560 5562
10. C. Li, R.P. Johnson, and J.A. Porco Jr. J. Am. Chem. Soc. 125 2003 5095 5106
11. X. Lei, R.P. Johnson, and J.A. Porco Jr. Angew. Chem., Int. Ed. 42 2003 3913 3917
12. K.A. Parker, and Y.H. Lim J. Am. Chem. Soc. 126 2004 15968 15969
13. J. Lumb, and D. Trauner J. Am. Chem. Soc. 127 2005 2870 2871
14. H.N. Lim, and K.A. Parker Org. Lett. 15 2013 398 401
15. C. Gonzalez, and H.B. Schlegel J. Phys. Chem. 94 1990 5523 5527
16. S.P.T. Matsuda, W.K. Wilson, and Q. Xiong Org. Biomol. Chem. 4 2006 530 543
17. Y. Takano, and K.N. Houk J. Chem. Theor. Comput. 1 2005 70 77
18. C.H. Heathcock Proc. Natl. Acad. Sci. U.S.A. 93 1996 14323 14327
19. G.A. Wallace, and C.H. Heathcock J. Org. Chem. 66 2001 450 454
20. J. Kobayashi, and T. Kubota Nat. Prod. Rep. 26 2009 936 962 and reference therein
21. C.R. Zhang, C.Q. Fan, S.H. Dong, H.B. Liu, W.B. Zhou, Y. Wu, and J.M. Yue Org. Lett. 13 2011 2440 2443
22. F. Wang, M.F. Mao, G.Z. Wei, Y. Gao, F.C. Ren, and J.K. Liu Phytochemistry 95 2013 428 435
23. Y. Zhang, Y.T. Di, Q. Zhang, S.Z. Mu, C.J. Tan, X. Fang, H.P. He, S.L. Li, and X.J. Hao Org. Lett. 11 2009 5414 5417
24. Y. Zhang, Y.T. Di, H.P. He, S.F. Li, Y. Lu, N.B. Gong, and X.J. Hao Eur. J. Org. Chem. 2011 2011 4103 4107
25. M.M. Cao, Y. Zhang, H.P. He, S.F. Li, S.D. Huang, D.Z. Chen, G.H. Tang, S.L. Li, Y.T. Di, and X.J. Hao J. Nat. Prod. 75 2012 1076 1082
26. Q. Zhang, T. Zhang, T.Q. Yang, Y.T. Di, and X.J. Hao RSC Adv. 3 2013 9658 9661
27. M.M. Cao, Y. Zhang, H.P. He, Y.C. Gu, Q. Zhang, Y. Li, C.M. Yuan, S.L. Li, Y.T. Di, and X.J. Hao Fitoterapia 89 2013 205 209
28. Y.T. Di, H.P. He, Y. Lv, P. Yi, L. Li, L. Wu, and X.J. Hao J. Nat. Prod. 69 2006 1074 1076
29. L.Ö. Demirezer, F. Gürbüz, Z. Güvenalp, K. Ströch, and A. Zeeck Turk. J. Chem. 30 2006 525 534
30. H. Morita, N. Yoshida, and J. Kobayashi Tetrahedron 55 1999 12549 12556
31. L.J. El-Naggar, and J.L. Beal J. Nat. Prod. 43 1980 649 707
32. B. Dinda, S. Debnath, and Y. Harigaya Chem. Pharm. Bull. 55 2007 689 728
33. B. Dinda, S. Debnath, and Y. Harigaya Chem. Pharm. Bull. 55 2007 159 222
34. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian-03 2005 Gaussian, Inc. Wallingford, CT
35. J.P. Perdew, J.A. Chevary, S.H. Vosko, K.A. Jackson, M.R. Pederson, D.J. Singh, and C. Fiolhais Phys. Rev. B 46 1992 6671 6687
36. C. Adamo, and V. Barone J. Chem. Phys. 108 1998 664 675
37. B.J. Lynch, P.L. Fast, M. Harris, and D.G. Truhlar J. Phys. Chem. A 104 2000 4811 4815
38. V. Guner, K.S. Khuong, A.G. Leach, P.S. Lee, M.D. Bartberger, and K.N. Houk J. Phys. Chem. A 107 2003 11445 11459
39. E. Goldstein, B. Beno, and K. Houk J. Am. Chem. Soc. 118 1996 6036 6043
40. L.R. Domingo, and J.A. Süaez Org. Biomol. Chem. 7 2009 3576 3583
41. TS2′ and TS4′ were not further discussed due to much higher in energy.
42. K.N. Houk Acc. Chem. Res. 8 1975 361 369
43. R. Wolfenden, and M.J. Snider Acc. Chem. Res. 34 2001 938 945
44. M. Garcia-Viloca, J. Gao, M. Karplus, and D.G. Truhlar Science 303 2004 186 195
45. M.G. Snider, B.S. Temple, and R. Wolfenden J. Phys. Org. Chem. 17 2004 586 591
46. A. Warshel, P.K. Sharma, M. Kato, Y. Xiang, H. Liu, and M.H.M. Olsson Chem. Rev. 106 2006 3210 3235
47. D.A. McQuarrie Statistical Mechanics 1976 Harper and Row New York, NY
48. D.J. Tantillo, J. Chen, and K.N. Houk Curr. Opin. Chem. Biol. 2 1998 743 750
49. D.J. Tantillo, and K.N. Houk Theozymes and Catalyst Design Stimulating Concepts in Chemistry 2000 Wiley-VCH Weinheim, Germany 79 88
50. F.P. Sousa, P.A. Fernandes, and M.J. Ramos J. Phys. Chem. A. 113 2009 14231 14236
51. D.J. Tantillo Org. Lett. 12 2010 1164 1167
52. J.L. McLaughlin K. Hostett-mann, Methods in Plant Biochemistry Vol. 6 1991 Academic London, U.K. 1 35