Identification of 3-hydroxyoctyl β-d-glucoside and absolute configuration of free and bound octane-1,3-diol in apple fruit

Wilfried Schwab; Gerhard Scheller; Doris Gerlach; Peter Schreier

doi:10.1016/0031-9422(89)85029-0

Identification of 3-hydroxyoctyl β-d-glucoside and absolute configuration of free and bound octane-1,3-diol in apple fruit

Wilfried Schwab, Gerhard Scheller, Doris Gerlach, Peter Schreier

University of Würzburg

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

In an extract obtained from neutralized apple juice, cv. Jonathan, by LC separation on Amberlite XAD resin using ethyl acetate caution, 3-hydroxyoctyl βd-glucoside was identified by HRGC, HRGC-MS and HRGC-FTIR after per-O-methylation. Chiral evaluation of free and glucosidically bound octane-1,3-diol was performed by HRGC after derivatization with Mosher's reagent revealing the occurrence of optically pure diol in apple fruit. By means of comparison of optical rotation of the 1,3-diacetoxy derivative with previously published data, (R)-(+)-configuration was evaluated.

Original language	English
Pages (from-to)	157-160
Number of pages	4
Journal	Phytochemistry
Volume	28
Issue number	1
DOIs	https://doi.org/10.1016/0031-9422(89)85029-0
State	Published - 1989
Externally published	Yes

Keywords

3-hydroxyoctyl β-d-glucoside
Malus sylvestris
Rosaceae
apple
free and bound (R)-(+)-octane-1,3-diol.
fruit

Access to Document

10.1016/0031-9422(89)85029-0

Cite this

@article{8c2aabd27bb34c93afd7cdbc0234a44f,

title = "Identification of 3-hydroxyoctyl β-d-glucoside and absolute configuration of free and bound octane-1,3-diol in apple fruit",

abstract = "In an extract obtained from neutralized apple juice, cv. Jonathan, by LC separation on Amberlite XAD resin using ethyl acetate caution, 3-hydroxyoctyl βd-glucoside was identified by HRGC, HRGC-MS and HRGC-FTIR after per-O-methylation. Chiral evaluation of free and glucosidically bound octane-1,3-diol was performed by HRGC after derivatization with Mosher's reagent revealing the occurrence of optically pure diol in apple fruit. By means of comparison of optical rotation of the 1,3-diacetoxy derivative with previously published data, (R)-(+)-configuration was evaluated.",

keywords = "3-hydroxyoctyl β-d-glucoside, Malus sylvestris, Rosaceae, apple, free and bound (R)-(+)-octane-1,3-diol., fruit",

author = "Wilfried Schwab and Gerhard Scheller and Doris Gerlach and Peter Schreier",

note = "Funding Information: Acknowledgements-T. Keller{\textquoteright}s skilful operation of HRGC-FTIR analyses is gratefully acknowledged. The Deutsche Forschungsgemeinschaft, Bonn, is thanked for the financial support of this work. D. Gerlach is grateful for the support of a Dechema Graduate Fellowship in the program {\textquoteleft}Biotechnology{\textquoteright} of the Bundesministerium fur Forschung und Technologie, Bonn.",

year = "1989",

doi = "10.1016/0031-9422(89)85029-0",

language = "English",

volume = "28",

pages = "157--160",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd.",

number = "1",

}

TY - JOUR

T1 - Identification of 3-hydroxyoctyl β-d-glucoside and absolute configuration of free and bound octane-1,3-diol in apple fruit

AU - Schwab, Wilfried

AU - Scheller, Gerhard

AU - Gerlach, Doris

AU - Schreier, Peter

N1 - Funding Information: Acknowledgements-T. Keller’s skilful operation of HRGC-FTIR analyses is gratefully acknowledged. The Deutsche Forschungsgemeinschaft, Bonn, is thanked for the financial support of this work. D. Gerlach is grateful for the support of a Dechema Graduate Fellowship in the program ‘Biotechnology’ of the Bundesministerium fur Forschung und Technologie, Bonn.

PY - 1989

Y1 - 1989

N2 - In an extract obtained from neutralized apple juice, cv. Jonathan, by LC separation on Amberlite XAD resin using ethyl acetate caution, 3-hydroxyoctyl βd-glucoside was identified by HRGC, HRGC-MS and HRGC-FTIR after per-O-methylation. Chiral evaluation of free and glucosidically bound octane-1,3-diol was performed by HRGC after derivatization with Mosher's reagent revealing the occurrence of optically pure diol in apple fruit. By means of comparison of optical rotation of the 1,3-diacetoxy derivative with previously published data, (R)-(+)-configuration was evaluated.

AB - In an extract obtained from neutralized apple juice, cv. Jonathan, by LC separation on Amberlite XAD resin using ethyl acetate caution, 3-hydroxyoctyl βd-glucoside was identified by HRGC, HRGC-MS and HRGC-FTIR after per-O-methylation. Chiral evaluation of free and glucosidically bound octane-1,3-diol was performed by HRGC after derivatization with Mosher's reagent revealing the occurrence of optically pure diol in apple fruit. By means of comparison of optical rotation of the 1,3-diacetoxy derivative with previously published data, (R)-(+)-configuration was evaluated.

KW - 3-hydroxyoctyl β-d-glucoside

KW - Malus sylvestris

KW - Rosaceae

KW - apple

KW - free and bound (R)-(+)-octane-1,3-diol.

KW - fruit

UR - https://www.scopus.com/pages/publications/0000117785

U2 - 10.1016/0031-9422(89)85029-0

DO - 10.1016/0031-9422(89)85029-0

M3 - Article

AN - SCOPUS:0000117785

SN - 0031-9422

VL - 28

SP - 157

EP - 160

JO - Phytochemistry

JF - Phytochemistry

IS - 1

ER -

Identification of 3-hydroxyoctyl β-d-glucoside and absolute configuration of free and bound octane-1,3-diol in apple fruit

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this