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Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana

Two new pentacyclic indole alkaloids, lirofolines A and B, possessing a novel rearranged ibogan ring system, are obtained from two Malayan Tabernaemontana species ( Tabernaemontana corymbosa and Tabernaemontana divaricata) and the structures are established by analysis of the spectroscopic data. A...

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Main Authors: Kam, T.S., Low, Y.Y., Lim, K.H., Choo, Y.M., Pang, H.S., Etoh, T., Hayashi, M., Komiyama, K.
Format: Article
Language:English
Published: Elsevier 2010
Subjects:
QD Chemistry
Online Access:http://eprints.um.edu.my/10396/1/Structure%2C_biological_activity%2C_and_a_biomimetic_partial_synthesis_of_the_lirofolines%2C_novel_pentacylic_indole_alkaloids_from_Tabernaemontana.pdf
http://eprints.um.edu.my/10396/
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spelling my.um.eprints.103962014-10-15T01:42:09Z http://eprints.um.edu.my/10396/ Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana Kam, T.S. Low, Y.Y. Lim, K.H. Choo, Y.M. Pang, H.S. Etoh, T. Hayashi, M. Komiyama, K. QD Chemistry Two new pentacyclic indole alkaloids, lirofolines A and B, possessing a novel rearranged ibogan ring system, are obtained from two Malayan Tabernaemontana species ( Tabernaemontana corymbosa and Tabernaemontana divaricata) and the structures are established by analysis of the spectroscopic data. A biomimetic partial synthesis of lirofoline A from ibogaine via the Polonovski reaction is carried out. Lirofolines A and B showed significant activity in reversing multidrug resistance in vincristine-resistant KB cells (IC50 3.4 and 7.5 µg/ml, respectively). Elsevier 2010 Article PeerReviewed application/pdf en http://eprints.um.edu.my/10396/1/Structure%2C_biological_activity%2C_and_a_biomimetic_partial_synthesis_of_the_lirofolines%2C_novel_pentacylic_indole_alkaloids_from_Tabernaemontana.pdf Kam, T.S. and Low, Y.Y. and Lim, K.H. and Choo, Y.M. and Pang, H.S. and Etoh, T. and Hayashi, M. and Komiyama, K. (2010) Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana. Tetrahedron Letters, 51. pp. 269-272. ISSN 0040-4039 doi:10.1016/j.tetlet.2009.10.122
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Kam, T.S.
Low, Y.Y.
Lim, K.H.
Choo, Y.M.
Pang, H.S.
Etoh, T.
Hayashi, M.
Komiyama, K.
Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana
description Two new pentacyclic indole alkaloids, lirofolines A and B, possessing a novel rearranged ibogan ring system, are obtained from two Malayan Tabernaemontana species ( Tabernaemontana corymbosa and Tabernaemontana divaricata) and the structures are established by analysis of the spectroscopic data. A biomimetic partial synthesis of lirofoline A from ibogaine via the Polonovski reaction is carried out. Lirofolines A and B showed significant activity in reversing multidrug resistance in vincristine-resistant KB cells (IC50 3.4 and 7.5 µg/ml, respectively).
format Article
author Kam, T.S.
Low, Y.Y.
Lim, K.H.
Choo, Y.M.
Pang, H.S.
Etoh, T.
Hayashi, M.
Komiyama, K.
author_facet Kam, T.S.
Low, Y.Y.
Lim, K.H.
Choo, Y.M.
Pang, H.S.
Etoh, T.
Hayashi, M.
Komiyama, K.
author_sort Kam, T.S.
title Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana
title_short Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana
title_full Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana
title_fullStr Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana
title_full_unstemmed Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana
title_sort structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from tabernaemontana
publisher Elsevier
publishDate 2010
url http://eprints.um.edu.my/10396/1/Structure%2C_biological_activity%2C_and_a_biomimetic_partial_synthesis_of_the_lirofolines%2C_novel_pentacylic_indole_alkaloids_from_Tabernaemontana.pdf
http://eprints.um.edu.my/10396/
_version_ 1643688788498579456
score 13.209306

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