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.

Autor: Suzuki M; Shizuoka University, 836 Ohya, Shizuoka 422-8529, Japan., Matsumoto S, Mizoguchi M, Hirata S, Takagi K, Hashimoto I, Yamano Y, Ito M, Fleischmann P, Winterhalter P, Morita T, Watanabe N
Jazyk: angličtina
Zdroj: Bioscience, biotechnology, and biochemistry [Biosci Biotechnol Biochem] 2002 Dec; Vol. 66 (12), pp. 2692-7.
DOI: 10.1271/bbb.66.2692
Abstrakt: 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.
Databáze: MEDLINE