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Trypanocidal diarylheptanoids from Aframomum letestuianum K. Schum (Zingiberaceae).

Kamnaing, P; Tsopmo, Apollinaire LU ; Tanifum, E A; Tchuendem, M H K; Tane, P; Ayafor, J F; Sterner, Olov LU ; Rattendi, D; Iwu, M M and Schuster, B, et al. (2003) In Journal of Natural Products 66(3). p.364-367
Abstract
Three new diarylheptanoids, (4Z,6E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-4,6-dien-3-one, letestuianin A (1), (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-4,6-dien-3-one, letestuianin B (2), and 1,7-bis(4-hydroxyphenyl)heptan-3,5-dione, letestuianin C (3), as well as the known (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-4,6-dien-3-one (5) were isolated from Aframomum letestuianum. The known flavonoids 3-acetoxy-5,7,4'-trihydroxyflavanone, 3-acetoxy-7-methoxy-5,4'-dihydroxyflavanone, 7-methoxy-3,5,4'-trihydroxyflavone, and 3,3',4',5,7-pentahydroxyflavan were also obtained from this plant. Their structures were determined using a combination of 1D and 2D NMR techniques. The four diarylheptanoids... (More)
Three new diarylheptanoids, (4Z,6E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-4,6-dien-3-one, letestuianin A (1), (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-4,6-dien-3-one, letestuianin B (2), and 1,7-bis(4-hydroxyphenyl)heptan-3,5-dione, letestuianin C (3), as well as the known (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-4,6-dien-3-one (5) were isolated from Aframomum letestuianum. The known flavonoids 3-acetoxy-5,7,4'-trihydroxyflavanone, 3-acetoxy-7-methoxy-5,4'-dihydroxyflavanone, 7-methoxy-3,5,4'-trihydroxyflavone, and 3,3',4',5,7-pentahydroxyflavan were also obtained from this plant. Their structures were determined using a combination of 1D and 2D NMR techniques. The four diarylheptanoids were tested for growth inhibitory activity in vitro versus bloodstream forms of African trypanosomes. IC50 values in the range of 1-3 g/mL were found for compounds 3 and 5. (Less)
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Contribution to journal
publication status
published
subject
in
Journal of Natural Products
volume
66
issue
3
pages
364 - 367
publisher
The American Chemical Society
external identifiers
  • pmid:12662093
  • wos:000181923100008
  • scopus:0037349085
ISSN
0163-3864
DOI
10.1021/np020362f
language
English
LU publication?
yes
id
66aeecd5-f809-42e2-8715-390a047dbc63 (old id 127932)
date added to LUP
2007-07-10 12:04:14
date last changed
2018-05-29 10:11:03
@article{66aeecd5-f809-42e2-8715-390a047dbc63,
  abstract     = {Three new diarylheptanoids, (4Z,6E)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)hepta-4,6-dien-3-one, letestuianin A (1), (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-4,6-dien-3-one, letestuianin B (2), and 1,7-bis(4-hydroxyphenyl)heptan-3,5-dione, letestuianin C (3), as well as the known (4Z,6E)-5-hydroxy-1,7-bis(4-hydroxyphenyl)hepta-4,6-dien-3-one (5) were isolated from Aframomum letestuianum. The known flavonoids 3-acetoxy-5,7,4'-trihydroxyflavanone, 3-acetoxy-7-methoxy-5,4'-dihydroxyflavanone, 7-methoxy-3,5,4'-trihydroxyflavone, and 3,3',4',5,7-pentahydroxyflavan were also obtained from this plant. Their structures were determined using a combination of 1D and 2D NMR techniques. The four diarylheptanoids were tested for growth inhibitory activity in vitro versus bloodstream forms of African trypanosomes. IC50 values in the range of 1-3 g/mL were found for compounds 3 and 5.},
  author       = {Kamnaing, P and Tsopmo, Apollinaire and Tanifum, E A and Tchuendem, M H K and Tane, P and Ayafor, J F and Sterner, Olov and Rattendi, D and Iwu, M M and Schuster, B and Bacchi, C},
  issn         = {0163-3864},
  language     = {eng},
  number       = {3},
  pages        = {364--367},
  publisher    = {The American Chemical Society},
  series       = {Journal of Natural Products},
  title        = {Trypanocidal diarylheptanoids from Aframomum letestuianum K. Schum (Zingiberaceae).},
  url          = {http://dx.doi.org/10.1021/np020362f},
  volume       = {66},
  year         = {2003},
}