Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Structure-Activity Relationship of Brassinosteroids with Respect to the A/B-Ring Functional Groups
SUGURU TAKATSUTONOBUO IKEKAWATADASHI MORISHITAHIROSHI ABE
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1987 Volume 35 Issue 1 Pages 211-216

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Abstract

In order to examine the biological role of the A/B-ring functional groups of plant-growth-promoting brassinosteroids, twenty-three brassinosteroids with some modifications at rings A and B (1-15 and 22-29) were bioassayed by means of the rice-lamina inclination test. The results showed that 1) removal of one or two hydroxyl groups from the A-ring reduced the biological activity of the steroids; 2) the 7-oxalactone brassinosteroids were almost as active as the corresponding 6-oxo steroids and they were much more active than their regioisomeric 6-oxalactone counterparts; 3) introduction of a double bond at the C-7 position and a hydroxyl group at the C-5 position of 6-oxo brassinosteroids significantly decreased the biological activity of the hormonal steroids. These data suggest that the presence of a 2α, 3α-diol, 7-oxalactone or 6-oxo group, and the A/B-trans ring junction are important for high biological activity.

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© The Pharmaceutical Society of Japan
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