Identification of (3S, 9R)- and (3S, 9S)-Megastigma-6,7-dien-3,5,9-triol 9-O-β-<small>D</small>-glucopyranosides as Damascenone Progenitors in the…

Masayuki SUZUKI; Shigetaka MATSUMOTO; Masaya MIZOGUCHI; Satoshi HIRATA; Kazuteru TAKAGI; Ikue HASHIMOTO; Yumiko YAMANO; Masayoshi ITO; Peter FLEISCHMANN; Peter WINTERHALTER; Tetuichiro MORITA; Naoharu WATANABE

doi:10.1271/bbb.66.2692

Food & Nutrition Science Notes

Identification of (3S, 9R)- and (3S, 9S)-Megastigma-6,7-dien-3,5,9-triol 9-O-β-D-glucopyranosides as Damascenone Progenitors in the…

Masayuki SUZUKI, Shigetaka MATSUMOTO, Masaya MIZOGUCHI, Satoshi HIRATA, Kazuteru TAKAGI, Ikue HASHIMOTO, Yumiko YAMANO, Masayoshi ITO, Peter FLEISCHMANN, Peter WINTERHALTER, Tetuichiro MORITA, Naoharu WATANABE

Author information

Masayuki SUZUKI
Shizuoka University
Shigetaka MATSUMOTO
Shizuoka University
Masaya MIZOGUCHI
Shizuoka University
Satoshi HIRATA
Shizuoka University
Kazuteru TAKAGI
Shizuoka University
Ikue HASHIMOTO
Shizuoka University
Yumiko YAMANO
Kobe Pharmaceutical University
Masayoshi ITO
Kobe Pharmaceutical University
Peter FLEISCHMANN
Institut für Lebensmittel Chemie
Peter WINTERHALTER
Institut für Lebensmittel Chemie
Tetuichiro MORITA
Jeol Co., Ltd., Applied Research Center
Naoharu WATANABE
Shizuoka University

Keywords: rose flower, damascenone, C₁₃-norisoprenoid, progenitor, megastigma-6,7-dien-3,5,9-triol 9-O-β-D-glucopyranoside

JOURNAL FREE ACCESS

2002 Volume 66 Issue 12 Pages 2692-2697

DOI https://doi.org/10.1271/bbb.66.2692

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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-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.

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