Biosynthesis of 2,3-epoxybrassinosteroids in seedlings of Secale cereale.
Two new brassinosteroids, (22R,23R,24S)-22,23-dihydroxy-24-methyl-5alpha-cholest-2-en-6-one (secasterol) and (22R,23R,24S)-22,23-dihydroxy-2alpha,3alpha-epoxy-24-methyl-5alpha-cholest-6-one (2,3-diepisecasterone) have been identified together with a known 2,3-epoxybrassinosteroid, secasterone, in seedlings of Secale cereale. Deuterated secasterol, teasterone, and typhasterol, upon administration to rye seedlings, were incorporated into secasterone and 2,3-diepisecasterone, indicating a biosynthetic route via teasterone/typhasterol to secasterol to 2,3-epoxybrassinosteroids.
Antonchick
Andrey P
AP
Max-Planck-Institute for Chemical Ecology, Beutenberg Campus, Winzerlaer Str. 10, D-07745 Jena, Germany.
Schneider
Bernd
B
Zhabinskii
Vladimir N
VN
Konstantinova
Olga V
OV
Khripach
Vladimir A
VA
D006888:Hydroxycholesterols / Q000097:blood / Q000737:chemistry; D015394:Molecular Structure; D012434:Secale / Q000737:chemistry / Q000378:metabolism*; D036226:Seedlings / Q000737:chemistry / Q000378:metabolism*; D013256:Steroids / Q000096:biosynthesis* / Q000737:chemistry*
C477919:(22R,23R,24S)-22,23-dihydroxy-24-methyl-5alpha-cholest-2-en-6-one; C477918:(22R,23R,24S)-22,23-dihydroxy-2alpha,3alpha-epoxy-24-methyl-5alpha-cholest-6-one; D006888:Hydroxycholesterols; D013256:Steroids