TY - JOUR
T1 - Structure-activity relationship of lepidimoide and its analogues
AU - Yamada, Kosumi
AU - Anai, Toyoaki
AU - Kosemura, Seiji
AU - Yamamura, Shosuke
AU - Hasegawa, Koji
N1 - Funding Information:
Acknowledoements--This work was supporteidn part by a Grant-Aid for ScientificR esearch(N o. 06454649f)r om the Ministry of EducationS, ciencea ndCulture of Japan (to K.H.). Financial support was also given by Shorai Foundationfo r Sciencea ndT echnologyJ,a pan(to K.H.).
PY - 1996
Y1 - 1996
N2 - The structure-activity relationship of lepidimoide and its analogues was investigated by means of the Amaranthus caudatus L. hypocotyl elongation test. In addition, the activities of α-D-galacturonic acid and L-( + )-rhamnose, which are component sugars of lepidimoide, were also studied. The carboxylic acid free type of lepidimoide showed growth-promoting activity as high as the original lepidimoide (sodium type). The acetylated compound showed considerably higher activity than lepidimoide, whereas the methylated lepidimoide did not show any activity. The hydroxylated lepidimoide without a double bond in the C-4,5 position showed lower activity. The sugar alcohol type of lepidimoide [2-O-(α-D-glucopyranosyl)-L-rhamnose] showed the highest activity in all the compounds studied. α-D-Galacturonic acid, L-( + )-rhamnose and their mixtures, which are component sugars of lepidimoide, exhibited only slight or no activity, respectively. D-Glucose and the mixture of D-glucose and L-( + )-rhamnose were also slightly active or inactive. These data suggest that the active sites in the chemical structure of the lepidimoide are the uronic acid derivative bearing an α,β-unsaturated carboxylate bonded to rhamnose via an α-glucoside linkage and a double bond in the C-4,5 position in the uronic acid.
AB - The structure-activity relationship of lepidimoide and its analogues was investigated by means of the Amaranthus caudatus L. hypocotyl elongation test. In addition, the activities of α-D-galacturonic acid and L-( + )-rhamnose, which are component sugars of lepidimoide, were also studied. The carboxylic acid free type of lepidimoide showed growth-promoting activity as high as the original lepidimoide (sodium type). The acetylated compound showed considerably higher activity than lepidimoide, whereas the methylated lepidimoide did not show any activity. The hydroxylated lepidimoide without a double bond in the C-4,5 position showed lower activity. The sugar alcohol type of lepidimoide [2-O-(α-D-glucopyranosyl)-L-rhamnose] showed the highest activity in all the compounds studied. α-D-Galacturonic acid, L-( + )-rhamnose and their mixtures, which are component sugars of lepidimoide, exhibited only slight or no activity, respectively. D-Glucose and the mixture of D-glucose and L-( + )-rhamnose were also slightly active or inactive. These data suggest that the active sites in the chemical structure of the lepidimoide are the uronic acid derivative bearing an α,β-unsaturated carboxylate bonded to rhamnose via an α-glucoside linkage and a double bond in the C-4,5 position in the uronic acid.
KW - Allelopathic substance
KW - Amaranthaceae
KW - Amaranthus caudatus L.
KW - Lepidimoide
KW - Structure-activity relationship
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U2 - 10.1016/0031-9422(95)00712-1
DO - 10.1016/0031-9422(95)00712-1
M3 - Article
C2 - 8835453
AN - SCOPUS:0030087684
SN - 0031-9422
VL - 41
SP - 671
EP - 673
JO - Phytochemistry
JF - Phytochemistry
IS - 3
ER -