Planta Med 2011; 77(3): 271-276
DOI: 10.1055/s-0030-1250344
Natural Product Chemistry
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Limonoids and Quinoline Alkaloids from Dictamnus dasycarpus

Jun-Li Yang1 , Lei-Lei Liu1 , Yan-Ping Shi1 , 2
  • 1State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, People's Republic of China
  • 2Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine , of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, People's Republic of China
Weitere Informationen

Publikationsverlauf

received May 25, 2010 revised July 19, 2010

accepted August 5, 2010

Publikationsdatum:
15. September 2010 (online)

Abstract

Phytochemical investigation on Dictamnus dasycarpus (Rutaceae) has led to the isolation of four new secondary metabolites (2, 6, 9, and 10) along with twelve known phytochemicals (1, 35, 7, 8, 1116). Compound 4 was isolated as a natural product for the first time. The structures of compounds 116 were elucidated by extensive spectroscopic analyses and comparison with previously reported spectroscopic data. The structures of 8 and 13 were further confirmed based on X‐ray data analyses. The absolute configuration of compounds 812 were studied based on the CD spectra analyses.

References

  • 1 Zhao P H, Sun L M, Gao M A, Yuan C S. Two limonoids from the root of Dictamnus radicis Cortex.  Chem Lett. 2007;  36 1200-1201
  • 2 Yoon J S, Sung S H, Kim Y C. Neuroprotective limonoids of root bark of Dictamnus dasycarpus.  J Nat Prod. 2008;  71 208-211
  • 3 Chen I S, Chen H F, Cheng M J, Chang Y L, Teng C M, Tsutomu I, Chen J J, Tsai I L. Quinoline alkaloids and other constituents of Melicope semecarpifolia with antiplatelet aggregation activity.  J Nat Prod. 2001;  64 1143-1147
  • 4 Muyard F, Bevalot F, Laude B, Vaquette J. Alkaloids from stem bark of Dutaillyea baudouinii.  Phytochemistry. 1992;  31 1087-1089
  • 5 Liu Z L, Xu Y J, Wu J, Goh S H, Ho S H. Feeding deterrents from Dictamnus dasycarpus Turcz. against two stored-product insects.  J Agric Food Chem. 2002;  50 1447-1450
  • 6 Zhou X, Ji C, Fu J, Li Y G, Chen T. Obacunone.  Acta Crystallogr E. 2006;  62 o5544-o5546
  • 7 Yuan T, Yang S P, Zhang C R, Zhang S, Yue J M. Two limonoids, khayalenoids A and B with an unprecedented 8-oxa-tricyclo[4.3.2.02, 7]undecane motif, from Khaya senegalensis.  Org Lett. 2009;  11 617-620
  • 8 Coggon P, McPhail A T. Structure and absolute configuration of fraxinellone: X-ray analysis of 9β-bromofraxinellone.  J Chem Soc. 1970;  1521-1524
  • 9 Yang R L, Jia T L, Zhang R Q. Microbial transformation of fraxinellone by Aspergillus niger.  J Asian Nat Prod Res. 2005;  7 843-845
  • 10 Zhao W M, Wolfender J L, Hostettmann K, Xu R S, Qin G W. Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus.  Phytochemistry. 1998;  47 7-11
  • 11 Barr S A, Boyd D R, Sharma N D, Loke P L. Synthesis and absolute configuration assignments of mono- and di-substitued chiral quinoline alkaloids obtained by asymmetric oxidation.  Heterocycles. 2009;  79 831-850
  • 12 Blaise A J, Winternitz F. Isofraxinellone, a limonoid lactone from the bark of Fagaropsis glabra.  Phytochemistry. 1985;  24 2379-2381
  • 13 Boustie J, Moulis C, Gleye J, Fouraste I, Servin P, Bon M. A degraded limonoid from Fagaropsis glabra.  Phytochemistry. 1990;  29 1699-1701
  • 14 Rugutt J K, Fischer N H, Nauman M A, Schmidt T J, Berner D K. 13C-NMR assignments for methyls and quaternary carbons of the limonoid obacunene.  Spectrosc Lett. 1996;  29 711-726
  • 15 Dreyer D L, Pickering M V, Cohan P. Distribution of limonoids in the rutaceae.  Phytochemistry. 1972;  11 705-713
  • 16 Sugimoto T, Miyase T, Kuroyanagi M, Ueno A. Limonoids and quinoline alkaloids from Evodia rutaecarpa Bentham.  Chem Pharm Bull. 1988;  36 4453-4461
  • 17 Yoon J S, Sung S H, Kim Y C. Neuroprotective limonoids of root bark of Dictamnus dasycarpus.  J Nat Prod. 2008;  71 208-211
  • 18 Zhao W M, Wolfender J L, Hostettmann K, Xu R S, Qin G W. Antifungal alkaloids and limonoid derivatives from Dictamnus dasycarpus.  Phytochemistry. 1998;  47 7-11

Prof. Yan-Ping Shi

Lanzhou Institute of Chemical Physics
Chinese Academy of Sciences

Lanzhou 730000

People's Republic of China

Telefon: + 86 93 14 96 82 08

Fax: + 86 93 18 27 70 88

eMail: shiyp@licp.cas.cn

>