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Synthesis of (24R)-28-homobrassinolide analogues and structure-activity relationships of brassinosteroids in the rice-lamina inclination test

1983; Elsevier BV; Volume: 22; Issue: 6 Linguagem: Inglês

10.1016/s0031-9422(00)84021-2

1873-3700

Suguru Takatsuto, Naoto Yazawa, Nobuo Ikekawa, Tadashi Morishita, Hiroshi Abe,

Seaweed-derived Bioactive Compounds

In order to investigate the biological importance of the alkyl group at the C-24 position of brassinolide, four (24R)-28-homobrassinofide analogues were synthesized from poriferasterol. The plant growth-promoting activity of brassinosteroids with a 24-methyl, -ethyl, or -hydrogen was examined by the rice-lamina inclination test. Structure-activity relationships of brassinosteroids with respect to the stereochemistry of the side chain were also investigated in this bioassay system. The results indicate that an S-configuration of the alkyl group at C-24, a cis-configuration of the C-22, C-23 vicinal diol, and the A,B-ring functionalities of brassinolide are structural requirements for significant plant growth-promoting activity.