TY - JOUR
T1 - Syntheses and novel bioactivities of artificial leaf-opening substances of Lespedeza cuneata G. Don, designed for the bioorganic studies of nyctinasty
AU - Ueda, Minoru
AU - Sawai, Yoshiyuki
AU - Yamamura, Shosuke
N1 - Funding Information:
(Japan) for Grant-in-Aid for Scientific Research on Special Promotion Research No. 09101001, the Asahi Glass Foundation, and Pioneering Research Project in Biotechnology given by the Ministry of Agriculture, Forestry and Fisheries for financial supports.
PY - 1999/9/3
Y1 - 1999/9/3
N2 - Potassium lespedezate (1) is the leaf-opening substance of a nyctinastic plant, Lespedeza cuneata G. Don. We have synthesized two sugar-derivatives of 1, potassium galactolespedezate (4) and mannolespedezate (6). Both 4 and 6 were quite effective for the leaf-opening of Cassia. mimosoides at 8 x 10-7 M, as strong as 1. However, 1 kept the leaf open only for a few days; on the other hand, 4 and 6 kept the leaf open after a week at that concentration. Additionally, remarkable difference was observed in the rate of enzymatic hydrolysis of natural and artificial leaf-opening sustance by using commercially available β-glucosidase. Therefore, 4 and 6 would not be hydrolized in the plant body, and are potentially useful molecular probes for the studies of the control of the nyctinastic leaf-movement by a biological clock.
AB - Potassium lespedezate (1) is the leaf-opening substance of a nyctinastic plant, Lespedeza cuneata G. Don. We have synthesized two sugar-derivatives of 1, potassium galactolespedezate (4) and mannolespedezate (6). Both 4 and 6 were quite effective for the leaf-opening of Cassia. mimosoides at 8 x 10-7 M, as strong as 1. However, 1 kept the leaf open only for a few days; on the other hand, 4 and 6 kept the leaf open after a week at that concentration. Additionally, remarkable difference was observed in the rate of enzymatic hydrolysis of natural and artificial leaf-opening sustance by using commercially available β-glucosidase. Therefore, 4 and 6 would not be hydrolized in the plant body, and are potentially useful molecular probes for the studies of the control of the nyctinastic leaf-movement by a biological clock.
KW - Biologically active compounds
KW - Glycosidation
KW - Glycoside
KW - Natural products
KW - Plants
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U2 - 10.1016/S0040-4020(99)00618-3
DO - 10.1016/S0040-4020(99)00618-3
M3 - Article
AN - SCOPUS:0033520253
SN - 0040-4020
VL - 55
SP - 10925
EP - 10936
JO - Tetrahedron
JF - Tetrahedron
IS - 36
ER -