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.
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.
Suzuki
Masayuki
M
Shizuoka University, 836 Ohya, Shizuoka 422-8529, Japan.
Matsumoto
Shigetaka
S
Mizoguchi
Masaya
M
Hirata
Satoshi
S
Takagi
Kazuteru
K
Hashimoto
Ikue
I
Yamano
Yumiko
Y
Ito
Masayoshi
M
Fleischmann
Peter
P
Winterhalter
Peter
P
Morita
Tetuichiro
T
Watanabe
Naoharu
N
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*
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