Lumusidines A-D and villalstonidine F, macroline-macroline and macroline-pleiocarpamine bisindole alkaloids from Alstonia macrophylla

Phytochemistry

Volumn 87, Issue , 2013, Pages 148-156

  Lim, Siew Huah ^a   Low, Yun Yee ^a   Subramaniam, G ^b   Abdullah, Zanariah ^a   Thomas, Noel F ^a   Kam, Toh Seok ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b SCHOOL OF ENGINEERING   (Singapore)

Author keywords

Alstonia macrophylla; Apocynaceae; Bisindole alkaloids; NMR; X ray crystallography

Indexed keywords

ALKALOID; INDOLE ALKALOID; MACROLINE; PLANT EXTRACT; PLEIOCARPAMINE;

ALSTONIA; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; X RAY DIFFRACTION;

ALKALOIDS; ALSTONIA; INDOLE ALKALOIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PLANT EXTRACTS; X-RAY DIFFRACTION;

ALSTONIA; ALSTONIA MACROPHYLLA; APOCYNACEAE;

EID: 84872815556     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2012.11.005     Document Type: Article

References (19)

1. I.H. Burkill A Dictionary of Economic Products of the Malay Peninsula 1966 Ministry of Agriculture and Co-operatives Kuala Lumpur
2. K. Changwichit, N. Khorana, K. Suwanborirux, N. Waranuch, N. Limpeanchob, W. Wisuitiprot, N. Suphrom, and K. Ingkaninan Bisindole alkaloids and secoiridoids from Alstonia macrophylla Wall. ex G. Don Fitoterapia 82 2011 798 804
3. H.D. Flack On enantiomorph-polarity estimation Acta Crystallogr. A 39 1983 876 881
4. H.D. Flack, and G. Bernardinelli Reporting and evaluating absolute-structure and absolute-configuration determinations J. Appl. Crystallogr. 33 2000 1143 1148 (Pubitemid 32182502)
5. K. Ghedira, M. Zeches-Hanrot, B. Richard, G. Massiot, L. Le Men-Olivier, T. Sevenet, and S.H. Goh Alkaloids of Alstonia angustifolia Phytochemistry 27 1988 3955 3962
6. M. Hesse, H. Hurzeler, C.W. Gemenden, B.S. Joshi, W.I. Taylor, and H. Schmid The structure of the Alstonia alkaloid villalstonine Helv. Chim. Acta 48 1965 689 704
7. R.W.W. Hooft, L.H. Straver, and A.L. Spek Using the t-distribution to improve the absolute structure assignment with likelihood calculations J. Appl. Crystallogr. 43 2010 665 668
8. R.W.W. Hooft, L.H. Straver, and A.L. Spek Determination of absolute structure using Bayesian statistics on Bijvoet differences J. Appl. Crystallogr. 41 2008 96 103
9. T.S. Kam, S.J. Tan, S.W. Ng, and K. Komiyama Bipleiophylline, an unprecedented cytotoxic bisindole alkaloid constituted from the bridging of two indole moieties by an aromatic spacer unit Org. Lett. 10 2008 3749 3752
10. T.S. Kam, and Y.M. Choo Bisindole alkaloids G.A. Cordell, The Alkaloids: Chemistry and Biology vol. 63 2006 Academic Press Amsterdam 181 337
11. T.S. Kam, Y.M. Choo, and K. Komiyama Unusual spirocyclic macroline alkaloids, nitrogenous derivatives, and a cytotoxic bisindole from Alstonia Tetrahedron 60 2004 3957 3966 (Pubitemid 38472003)
12. T.S. Kam Alkaloids from Malaysian flora S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives vol. 14 1999 Pergamon Amsterdam 285 435
13. N. Keawpradub, P.J. Houghton, E. Eno-Amooquaye, and P.J. Burke Activity of extracts and Thai Alstonia species against human lung cancer cell lines Planta Med. 63 1997 97 101 (Pubitemid 27196072)
14. S.H. Lim, Y.Y. Low, S.J. Tan, K.H. Lim, N.F. Thomas, and T.S. Kam Perhentidines A-C: macroline-macroline bisindoles from Alstonia and the absolute configuration of perhentinine and macralstonine J. Nat. Prod. 75 2012 942 950
15. S.H. Lim, S.J. Tan, Y.Y. Low, and T.S. Kam Lumutinines A-D, linearly fused macroline-macroline and macroline-sarpagine bisindoles from Alstonia macrophylla J. Nat. Prod. 74 2011 2556 2562
16. F. Markgraf Apocynaceae II Blumea 22 1974 20 29
17. L.M. Perry, and J. Metzger Medicinal Plants of East and Southeast Asia 1980 MIT Press Cambridge
18. Sidiyasa, K.; 1998. Taxonomy, Phylogeny, and Wood Anatomy of Alstonia (Apocynaceae). vol. Blumea Supplement 11. Rijksherbarium/Hortus Botanicus, The Netherlands, pp. 1-230.
19. T.C. Whitmore Tree Flora of Malaya vol. 2 1973 Longman London 7 12