title: Biosynthesis of 2,3-epoxybrassinosteroids in seedlings of Secale cereale.
abstract: 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.
authors.affiliation: Max-Planck-Institute for Chemical Ecology, Beutenberg Campus, Winzerlaer Str. 10, D-07745 Jena, Germany.
authors.forename: Andrey P
authors.initials: AP
authors.lastname: Antonchick
authors.forename: Bernd
authors.initials: B
authors.lastname: Schneider
authors.forename: Vladimir N
authors.initials: VN
authors.lastname: Zhabinskii
authors.forename: Olga V
authors.initials: OV
authors.lastname: Konstantinova
authors.forename: Vladimir A
authors.initials: VA
authors.lastname: Khripach
mesh_terms: 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*
chemical_list: 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