Anti-trypanosomal activity of diarylheptanoids isolated from the bark of Alnus japonica.
Am J Chin Med
; 42(5): 1245-60, 2014.
Article
em En
| MEDLINE
| ID: mdl-25178281
ABSTRACT
The crude extract of Alnus japonica bark exhibited a strong effect on the growth of Trypanosoma brucei. Subsequent chromatographic separation resulted in the isolation of two novel diarylheptanoids, known as alnuside C (2) and alnuside D (3), and three known compounds, 1-(3,4-dihydroxyphenyl)-7-(4-hydroxyphenyl)-heptan-3(R)-O-ß-D-glucopyranoside (1), oregonin (4) and hirsutanone (5). The structures of the isolates were elucidated based on the use of extensive spectroscopic and chemical methods. Among the isolated diarylheptanoids, oregonin (4) (a major component of plant bark) and hirsutanone (5) exhibited potent in vitro inhibitory activity against T. brucei growth in the bloodstream with IC50 values of 1.14 and 1.78 µM, respectively. We confirmed that oregonin (4) and hirsutanone (5) were not toxic to human normal skin fibroblast cells (NB1RGB) and colon cancer cells (HCT-15) at a concentration of 50 µM; however, lower levels of toxicity were observed for leukemia cells. To determine the structure activity relationships of the isolated components, we performed Conformation Search and found that the 3-oxo function of the heptane chain in the diarylheptanoid molecule is required for their trypanocidal activity.
Palavras-chave
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Tripanossomicidas
/
Trypanosoma brucei brucei
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Extratos Vegetais
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Alnus
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Diarileptanoides
Limite:
Animals
/
Humans
Idioma:
En
Revista:
Am J Chin Med
Ano de publicação:
2014
Tipo de documento:
Article
País de afiliação:
Japão
País de publicação:
SG
/
SINGAPORE
/
SINGAPUR
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SINGAPURA