Biosynthesis of octane-1,3-diol in apple fruit

Till Beuerle; Wilfried Schwab

doi:10.1016/S0031-9422(97)00108-8

Biosynthesis of octane-1,3-diol in apple fruit

Till Beuerle, Wilfried Schwab

University of Würzburg

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

6 Scopus citations

Abstract

The biosynthesis of octane-1,3-diol and 3-hydroxy-octyl-β-D- glucopyranoside was investigated by administering [1-¹⁴C]hexanoic acid, [1- ¹⁴C]octanoic acid and [U-¹⁴C]linoleic acid into intact ripe apple fruits cv. Peau de Chien. After a storage period of 2 months at 4, the metabolites were isolated by solid phase extraction and analysed by HPLC and TLC. The fatty acids were converted to octane-1,3-diol with incorporation rates of 3.9, 3.4 and 16.2% and to 3-hydroxy-octyl-β-D-glucopyranoside with transformation rates of 0.9, 0.4 and 3.0% for hexanoic, octanoic and linoleic acid, respectively. No other major metabolites were detected. Enzymatic hydrolysis of the solid residues released additional amounts of [¹⁴C] octane-1,3-diol.

Original language	English
Pages (from-to)	1153-1155
Number of pages	3
Journal	Phytochemistry
Volume	45
Issue number	6
DOIs	https://doi.org/10.1016/S0031-9422(97)00108-8
State	Published - Jul 1997
Externally published	Yes

Keywords

3-Hydroxy-octyl- β-D-glucopyranoside
Apple fruit
Biosynthesis
Hexanoic acid
Linoleic acid
Malus sylvestris
Octane-1,3-diol
Octanoic acid
Rosaceae

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10.1016/S0031-9422(97)00108-8

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@article{c06973ffc1a54d02b258534c7e237463,

title = "Biosynthesis of octane-1,3-diol in apple fruit",

abstract = "The biosynthesis of octane-1,3-diol and 3-hydroxy-octyl-β-D- glucopyranoside was investigated by administering [1-14C]hexanoic acid, [1- 14C]octanoic acid and [U-14C]linoleic acid into intact ripe apple fruits cv. Peau de Chien. After a storage period of 2 months at 4, the metabolites were isolated by solid phase extraction and analysed by HPLC and TLC. The fatty acids were converted to octane-1,3-diol with incorporation rates of 3.9, 3.4 and 16.2% and to 3-hydroxy-octyl-β-D-glucopyranoside with transformation rates of 0.9, 0.4 and 3.0% for hexanoic, octanoic and linoleic acid, respectively. No other major metabolites were detected. Enzymatic hydrolysis of the solid residues released additional amounts of [14C] octane-1,3-diol.",

keywords = "3-Hydroxy-octyl- β-D-glucopyranoside, Apple fruit, Biosynthesis, Hexanoic acid, Linoleic acid, Malus sylvestris, Octane-1,3-diol, Octanoic acid, Rosaceae",

author = "Till Beuerle and Wilfried Schwab",

note = "Funding Information: Acknowledgements-Dr P. Brunerie is thanked for providing apples. We extend appreciation to Professor G. Bringmann (Institute of Organic Chemistry) for the use of the radiochemical laboratory and the assistance of R. Roscher is gratefully acknowledged. The authors wish to thank the Deutsche Forschungs-gemeinschaft (SCHW 63411-l) and Fonds der Chem-ischen Industrie for funding.",

year = "1997",

month = jul,

doi = "10.1016/S0031-9422(97)00108-8",

language = "English",

volume = "45",

pages = "1153--1155",

journal = "Phytochemistry",

issn = "0031-9422",

publisher = "Elsevier Ltd.",

number = "6",

}

TY - JOUR

T1 - Biosynthesis of octane-1,3-diol in apple fruit

AU - Beuerle, Till

AU - Schwab, Wilfried

N1 - Funding Information: Acknowledgements-Dr P. Brunerie is thanked for providing apples. We extend appreciation to Professor G. Bringmann (Institute of Organic Chemistry) for the use of the radiochemical laboratory and the assistance of R. Roscher is gratefully acknowledged. The authors wish to thank the Deutsche Forschungs-gemeinschaft (SCHW 63411-l) and Fonds der Chem-ischen Industrie for funding.

PY - 1997/7

Y1 - 1997/7

N2 - The biosynthesis of octane-1,3-diol and 3-hydroxy-octyl-β-D- glucopyranoside was investigated by administering [1-14C]hexanoic acid, [1- 14C]octanoic acid and [U-14C]linoleic acid into intact ripe apple fruits cv. Peau de Chien. After a storage period of 2 months at 4, the metabolites were isolated by solid phase extraction and analysed by HPLC and TLC. The fatty acids were converted to octane-1,3-diol with incorporation rates of 3.9, 3.4 and 16.2% and to 3-hydroxy-octyl-β-D-glucopyranoside with transformation rates of 0.9, 0.4 and 3.0% for hexanoic, octanoic and linoleic acid, respectively. No other major metabolites were detected. Enzymatic hydrolysis of the solid residues released additional amounts of [14C] octane-1,3-diol.

AB - The biosynthesis of octane-1,3-diol and 3-hydroxy-octyl-β-D- glucopyranoside was investigated by administering [1-14C]hexanoic acid, [1- 14C]octanoic acid and [U-14C]linoleic acid into intact ripe apple fruits cv. Peau de Chien. After a storage period of 2 months at 4, the metabolites were isolated by solid phase extraction and analysed by HPLC and TLC. The fatty acids were converted to octane-1,3-diol with incorporation rates of 3.9, 3.4 and 16.2% and to 3-hydroxy-octyl-β-D-glucopyranoside with transformation rates of 0.9, 0.4 and 3.0% for hexanoic, octanoic and linoleic acid, respectively. No other major metabolites were detected. Enzymatic hydrolysis of the solid residues released additional amounts of [14C] octane-1,3-diol.

KW - 3-Hydroxy-octyl- β-D-glucopyranoside

KW - Apple fruit

KW - Biosynthesis

KW - Hexanoic acid

KW - Linoleic acid

KW - Malus sylvestris

KW - Octane-1,3-diol

KW - Octanoic acid

KW - Rosaceae

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U2 - 10.1016/S0031-9422(97)00108-8

DO - 10.1016/S0031-9422(97)00108-8

M3 - Article

AN - SCOPUS:0030958792

SN - 0031-9422

VL - 45

SP - 1153

EP - 1155

JO - Phytochemistry

JF - Phytochemistry

IS - 6

ER -

Biosynthesis of octane-1,3-diol in apple fruit

Abstract

Keywords

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