Lipoxygenase-mediated cleavage of fatty acids to carbonyl fragments in tomato fruits

Galliard, T.; Matthew, Jennifer A.

doi:10.1016/0031-9422(77)80060-5

Cited by 115 publications

(49 citation statements)

References 19 publications

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“…Substrate specificity of the reaction suggests that lipoxygenase is involved. The fact that oleic acid is not a substrate argues with other data indicating plant lipoxygenase involvement (40). This is supported by immunological data where antibodies to a putative plastidial rice lipoxygenase (41) positively reacted with the plastidial pepper lipoxygenase (Fig.…”

Section: Resultssupporting

confidence: 59%

Xanthophyll Biosynthesis

Bouvier

d’Harlingue

Hugueney

et al. 1996

Journal of Biological Chemistry

157

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Pepper (Capsicum annuum) ␤-cyclohexenyl xanthophyll epoxidase cDNA was cloned and the corresponding enzyme overexpressed and purified from Escherichia coli, for investigation of its catalytic activity. The recombinant protein did not directly accept NADPH for epoxidation of cyclohexenyl carotenoids, nor did it operate according to a peroxygenase-based mechanism. Instead, the reducing power of NADPH was transferred to the epoxidase via reduced ferredoxin as shown by reconstitution of epoxidase activity in the presence of NADPH, ferredoxin oxidoreductase, and ferredoxin. Bacterial rubredoxin could be substituted for ferredoxin. The pepper epoxidase acted specifically on the ␤-ring of xanthophylls such as ␤-cryptoxanthin, zeaxanthin, and antheraxanthin. The proposed reaction mechanism for epoxidation involves the formation of a transient carbocation. This characteristic allows selective inhibition of the epoxidase activity by different nucleophilic diethylamine derivatives, p-dimethylaminobenzenediazonium fluoroborate and N,N-dimethyl-2-phenylaziridinium. It was also shown that the epoxidase gene was up-regulated during oxidative stress and when chloroplasts undergo differentiation into chromoplasts in pepper fruit.

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Section: Resultssupporting

confidence: 59%

Xanthophyll Biosynthesis

Bouvier

d’Harlingue

Hugueney

et al. 1996

Journal of Biological Chemistry

157

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“…Similarly, the hexenal level was increased by addition of linolenic acid [11]. The increase of hexanal and 1-hexanol upon addition of linoleic acid and the increase of (Z)-3-hexenal and (E)-2-hexenal upon addition of linolenic acid have been reported in other studies in tomato [12,3], bell pepper [13] and cucumber [14]. When LOX activity in tomato was decreased by reducing expression of LOX mRNA, the levels of hexenal and hexanal were significantly decreased [11].…”

Section: Introductionsupporting

confidence: 71%

“…Thus, it appears that a higher ratio of linoleic acid:linolenic results in a higher ratio of hexanal:hexenal. An increase of hexanal upon addition of linoleic acid and an increase of (Z)-3-hexenal and (E)-2-hexenal upon addition of linolenic acid have also been reported in tomato [3,12], bell pepper [13] and cucumber [14]. However, there was no strong correlation between the ratio of linoleic acid:linolenic acid and the ratio of hexanal:hexenal in the Solanaceae family (R2=0.65) ( Table 3).…”

Section: Effect Of Fatty Acid Concentration On Volatile Concentrationmentioning

confidence: 82%

“…The main products of the LOX pathway are C6 aldehydes and alcohols generated through sequential enzymatic reactions. The major enzymes in this pathway include lipoxygenase, hydroperoxide lyase (HPL), alcohol dehydrogenase (ADH) and (Z)-3/(E)-2 isomerase [3]. Linoleic and linolenic acids are the substrates that are converted to volatiles such as hexanal, (Z)-3-hexenal, (E)-2-hexenal, 1-hexanol, hexen-1-ol, (E)-2-octenal, (E)-2-heptenal, (E)-2-pentenal 1-penten-3-one, hexanoic acid, (Z)-3-hexenyl acetate and hexyl acetate.…”

Section: Introductionmentioning

confidence: 99%

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Formation of Volatiles in the Lipoxygenase Pathway as Affected by Fruit Type and Temperature

Han¹,

Barringer²

2015

J Exp Food Chem

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Objective: The objective of this study is to study the effect of temperature, lipoxygenase activity, substrate and fruit type on formation of volatiles in the LOX pathway. Methods:Volatiles in the headspace of tomato, bell pepper, tomatillo, strawberry, apple and pear were measured during and after fruit tissue disruption in real time using selected ion flow tube mass spectrometry (SIFT-MS) at 4, 25, 37 and 45°C for 60 min, and were compared to lipoxygenase (LOX) activity and fatty acid concentration. Results:In tomatoes, bell peppers and tomatillos, (Z)-3-hexenal, (E)-2-hexenal and hexanal increased rapidly after blending, peaked and declined, while in strawberry, apple and pear they sometimes peaked and sometimes remained constant over the 60 min. In tomato and bell pepper, the peak levels of (Z)-3-hexenal, (E)-2-hexenal and hexanal in the LOX pathway had good correlations to LOX activity, which was greatest at 25°C. In contrast, tomatillo, strawberry, apple and pear had lower LOX activity, their 6C aldehydes did not show strong correlation with LOX activity, and the volatiles increased with increasing temperature to 45°C. The concentrations of hexen-1-ol and 1-hexanol did not correlate to LOX activity for any of the fruits. In tomato, bell pepper and tomatillo, there was no significant correlation between the ratio of linoleic acid:linolenic and the ratio of hexanal:hexenal. In strawberry, apple and pear, there were good correlations between linolenic acid content and concentrations of (E)-2-hexenal, hexenal and hexen-1-ol. Conclusion:Thus the effect of enzyme activity and substrate composition on formation of volatiles in the lipoxygenase pathway remains complicated and difficult to predict.

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“…The 13-hydroperoxide product is further metabolized into other products, including jasmonic acid, a plant growth regulator, and hexenal, the volatile compound that gives tomato fruit its aroma. However, formation of the 9-hydroperoxide product is favored over the 13-hydroperoxide by 24:l by LOX that is present in tomato fruits (Galliard and Matthew, 1977;Regdel et al, 1994). The fate of the 9-hydroperoxide product is unknown, but about 0.1% of it may be converted to hexanal under high concentrations (Hantanaka et al, 1992).…”

Section: Discussionmentioning

confidence: 99%

Molecular Cloning of a Ripening-Specific Lipoxygenase and Its Expression during Wild-Type and Mutant Tomato Fruit Development

Kausch

Handa

1997

Plant Physiology

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A 94-kD protein that accumulates predominately in tomato (Lycopersicon esculenfum) fruit during ripening was purified, and antibodies specific for the purified protein were used to isolate cDNA clones from a red-ripe fruit cDNA library. A sequence analysis of these cDNAs and cross-reactivity of the 94-kD-specific antibodies to the soybean lipoxygenase (LOX) L-1, L-2, and L-3 proteins and soybean LOX L-l-specific antibodies to the 94-kD protein identified it as a member of the LOX gene family. Maximum levels of the 94-kD LOX mRNA and protein are present in breaker to ripe and red-ripe stages, respectively. Expression of 94-kD LOX in different tissues from mature green and red-ripe tomato fruits was found to be greatest in the radial walls of ripe fruit, but immunocytolocalization using tissue printing suggests that the highest accumulation of its protein occurs in locular jelly. None of 94-kD LOX is expressed in nonripening mutant fruits of any age. Never-ripe mutant fruit accumulate the 94-kD LOX mRNA to levels similar to those obtained in wild-type fruit, but fail to accumulate the 94-kD LOX protein. Collectively, the results show that expression of 94-kD LOX is regulated by the ripening process, and ethylene may play a role in its protein accumulation.

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Lipoxygenase-mediated cleavage of fatty acids to carbonyl fragments in tomato fruits

Cited by 115 publications

References 19 publications

Xanthophyll Biosynthesis

Xanthophyll Biosynthesis

Formation of Volatiles in the Lipoxygenase Pathway as Affected by Fruit Type and Temperature

Molecular Cloning of a Ripening-Specific Lipoxygenase and Its Expression during Wild-Type and Mutant Tomato Fruit Development

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