| RRC ID |
45265
|
| Author |
Tung NH, Suzuki M, Uto T, Morinaga O, Kwofie KD, Ammah N, Koram KA, Aboagye F, Edoh D, Yamashita T, Yamaguchi Y, Setsu T, Yamaoka S, Ohta N, Shoyama Y.
|
| Title |
Anti-trypanosomal activity of diarylheptanoids isolated from the bark of Alnus japonica.
|
| Journal |
Am J Chin Med
|
| 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-β-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.
|
| Volume |
42(5)
|
| Pages |
1245-60
|
| Published |
2014-1-1
|
| DOI |
10.1142/S0192415X14500785
|
| PMID |
25178281
|
| MeSH |
Alnus*
Animals
Cells, Cultured
Colonic Neoplasms / pathology
Diarylheptanoids / chemistry
Diarylheptanoids / isolation & purification
Diarylheptanoids / pharmacology*
Dose-Response Relationship, Drug
Fibroblasts / drug effects
Humans
In Vitro Techniques
Leukemia / pathology
Plant Bark
Plant Extracts / chemistry
Plant Extracts / pharmacology*
Plant Extracts / toxicity
Skin / cytology
Structure-Activity Relationship
Trypanocidal Agents*
Trypanosoma brucei brucei / drug effects*
Trypanosoma brucei brucei / growth & development*
Tumor Cells, Cultured
|
| IF |
3.682
|
| Times Cited |
10
|
|
WOS Category
|
INTEGRATIVE & COMPLEMENTARY MEDICINE
|
| Resource |
| Human and Animal Cells |
Jurkat
U937
HL60(RCB0041)
THP-1(RCB1189)
NB1RGB(RCB0222) |
