Conjugated triene oxidation products of α-farnesene induce symptoms of superficial scald on stored apples

D. D. Rowan; M. B. Hunt; S. Fielder; J. Norris; M. S. Sherburn

doi:10.1021/jf0015221

Conjugated triene oxidation products of α-farnesene induce symptoms of superficial scald on stored apples

D. D. Rowan^*, M. B. Hunt, S. Fielder, J. Norris, M. S. Sherburn

^*Corresponding author for this work

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

86 Citations (Scopus)

Abstract

The sesquiterpene α-farnesene (1) and its conjugated triene oxidation products accumulate in the skin of apples after harvest and are implicated as the causal agents of superficial scald. Conjugated triene oxidation products and analogues were synthesized and applied to the surface of Granny Smith apples either as vapors or in squalane. Farnesyl hydroperoxide (2a), trienol (2b), endoperoxide (3a), dehydronerolidol (5), and cumyl hydroperoxide (4) all produced the symptoms of superficial scald when applied at nanomolar doses. Scald-inducing activity was dependent on the mode of application. Farnesyl hydroperoxide (2a) was the most active conjugated triene when applied directly to the apple skin. Trienol (2b) also induced scald symptoms and partially reversed the inhibition of scald caused by diphenylamine.

Original language	English
Pages (from-to)	2780-2787
Number of pages	8
Journal	Journal of Agricultural and Food Chemistry
Volume	49
Issue number	6
DOIs	https://doi.org/10.1021/jf0015221
Publication status	Published - 2001
Externally published	Yes

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title = "Conjugated triene oxidation products of α-farnesene induce symptoms of superficial scald on stored apples",

abstract = "The sesquiterpene α-farnesene (1) and its conjugated triene oxidation products accumulate in the skin of apples after harvest and are implicated as the causal agents of superficial scald. Conjugated triene oxidation products and analogues were synthesized and applied to the surface of Granny Smith apples either as vapors or in squalane. Farnesyl hydroperoxide (2a), trienol (2b), endoperoxide (3a), dehydronerolidol (5), and cumyl hydroperoxide (4) all produced the symptoms of superficial scald when applied at nanomolar doses. Scald-inducing activity was dependent on the mode of application. Farnesyl hydroperoxide (2a) was the most active conjugated triene when applied directly to the apple skin. Trienol (2b) also induced scald symptoms and partially reversed the inhibition of scald caused by diphenylamine.",

keywords = "Apples, Autoxidation, Conjugated triene, Superficial scald, α-farnesene",

author = "Rowan, {D. D.} and Hunt, {M. B.} and S. Fielder and J. Norris and Sherburn, {M. S.}",

year = "2001",

doi = "10.1021/jf0015221",

language = "English",

volume = "49",

pages = "2780--2787",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Conjugated triene oxidation products of α-farnesene induce symptoms of superficial scald on stored apples

AU - Rowan, D. D.

AU - Hunt, M. B.

AU - Fielder, S.

AU - Norris, J.

AU - Sherburn, M. S.

PY - 2001

Y1 - 2001

N2 - The sesquiterpene α-farnesene (1) and its conjugated triene oxidation products accumulate in the skin of apples after harvest and are implicated as the causal agents of superficial scald. Conjugated triene oxidation products and analogues were synthesized and applied to the surface of Granny Smith apples either as vapors or in squalane. Farnesyl hydroperoxide (2a), trienol (2b), endoperoxide (3a), dehydronerolidol (5), and cumyl hydroperoxide (4) all produced the symptoms of superficial scald when applied at nanomolar doses. Scald-inducing activity was dependent on the mode of application. Farnesyl hydroperoxide (2a) was the most active conjugated triene when applied directly to the apple skin. Trienol (2b) also induced scald symptoms and partially reversed the inhibition of scald caused by diphenylamine.

AB - The sesquiterpene α-farnesene (1) and its conjugated triene oxidation products accumulate in the skin of apples after harvest and are implicated as the causal agents of superficial scald. Conjugated triene oxidation products and analogues were synthesized and applied to the surface of Granny Smith apples either as vapors or in squalane. Farnesyl hydroperoxide (2a), trienol (2b), endoperoxide (3a), dehydronerolidol (5), and cumyl hydroperoxide (4) all produced the symptoms of superficial scald when applied at nanomolar doses. Scald-inducing activity was dependent on the mode of application. Farnesyl hydroperoxide (2a) was the most active conjugated triene when applied directly to the apple skin. Trienol (2b) also induced scald symptoms and partially reversed the inhibition of scald caused by diphenylamine.

KW - Apples

KW - Autoxidation

KW - Conjugated triene

KW - Superficial scald

KW - α-farnesene

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U2 - 10.1021/jf0015221

DO - 10.1021/jf0015221

M3 - Article

SN - 0021-8561

VL - 49

SP - 2780

EP - 2787

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 6

ER -

Conjugated triene oxidation products of α-farnesene induce symptoms of superficial scald on stored apples

Abstract

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