title: Identification of (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-beta-D-glucopyranosides as damascenone progenitors in the flowers of Rosa damascena Mill.
abstract: The progenitors of damascenone (1), the most intensive C13-norisoprenoid volatile aroma constituent of rose essential oil, were surveyed in the flowers of Rosa damascena Mill. Besides 9-O-beta-D-glucopyranosyl-3-hydroxy-7,8-didehydro-beta-ionol (4b), a stable progenitor already isolated from the residual water after steam distillation of flowers of R. damascena Mill., two labile progenitors were identified to be (3S, 9R)- and (3S, 9S)-megastigma-6,7-dien-3,5,9-triol 9-O-beta-D-glucopyranosides (2b) based on their synthesis and HPLC-MS analytical data. Compound 2b gave damascenone (1), 3-hydroxy-beta-damascone (3) and 4b upon heating under acidic conditions.
authors.affiliation: Shizuoka University, 836 Ohya, Shizuoka 422-8529, Japan.
authors.forename: Masayuki
authors.initials: M
authors.lastname: Suzuki
authors.forename: Shigetaka
authors.initials: S
authors.lastname: Matsumoto
authors.forename: Masaya
authors.initials: M
authors.lastname: Mizoguchi
authors.forename: Satoshi
authors.initials: S
authors.lastname: Hirata
authors.forename: Kazuteru
authors.initials: K
authors.lastname: Takagi
authors.forename: Ikue
authors.initials: I
authors.lastname: Hashimoto
authors.forename: Yumiko
authors.initials: Y
authors.lastname: Yamano
authors.forename: Masayoshi
authors.initials: M
authors.lastname: Ito
authors.forename: Peter
authors.initials: P
authors.lastname: Fleischmann
authors.forename: Peter
authors.initials: P
authors.lastname: Winterhalter
authors.forename: Tetuichiro
authors.initials: T
authors.lastname: Morita
authors.forename: Naoharu
authors.initials: N
authors.lastname: Watanabe
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003510:Cyclohexanes / Q000737:chemistry / Q000378:metabolism; D035264:Flowers / Q000378:metabolism*; D005960:Glucosides / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D045792:Norisoprenoids; D027826:Rosa / Q000378:metabolism*; D013729:Terpenes / Q000737:chemistry / Q000378:metabolism*
chemical_list: C476262:3-hydroxy-beta-damascone; C476260:9-O-glucopyranosyl-3-hydroxy-7,8-didehydro-beta-ionol; D003510:Cyclohexanes; D005960:Glucosides; D045792:Norisoprenoids; D013729:Terpenes; C476261:megastigma-6,7-dien-3,5,9-triol 9-O-glycopyranoside; C075388:beta-damascenone