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

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-β-D-glucopyranosyl-3-hydroxy-7,8-didehydro-β-ionol (4b), a stable progenitor already isolated from the residual...

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Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2002-12, Vol.66 (12), p.2692
Main Authors: SUZUKI, Masayuki, MATSUMOTO, Shigetaka, MIZOGUCHI, Masaya, HIRATA, Satoshi, TAKAGI, Kazuteru, HASHIMOTO, Ikue, YAMANO, Yumiko, ITO, Masayoshi, FLEISCHMANN, Peter, WINTERHALTER, Peter, MORITA, Tetuichiro, WATANABE, Naoharu
Format: Article
Language:English
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Summary: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-β-D-glucopyranosyl-3-hydroxy-7,8-didehydro-β-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-β-D-glucopyranosides (2b) based on their synthesis and HPLC-MS analytical data. Compound 2b gave damascenone (1), 3-hydroxy-β-damascone (3) and 4b upon heating under acidic conditions.
ISSN:0916-8451
1347-6947