Distribution of lipoxygenase and hydroperoxide lyase in the leaves of various plant species

Sekiya, Jiro; Kajiwara, Tadahiko; Munechika, Koji; Hatanaka, Akikazu

doi:10.1016/0031-9422(83)80003-x

Cited by 52 publications

(23 citation statements)

References 11 publications

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“…The next transformation step depends on the HPL enzymatic activity of the selected plant, and may be limited by its extractability, stability and specificity. HPL activity was first measured in watermelon seedlings [11], tea leaves [12], alfalfa seedlings [13], soya leaf [14], spinach leaves [15] and olive fruits [16]. However the enzymatic mechanism was completely elucidated only a few years ago [17,18].…”

Section: Introductionmentioning

confidence: 99%

Optimization and scaling up of a biotechnological synthesis of natural green leaf volatiles using Beta vulgaris hydroperoxide lyase

Gigot

Ongena

Fauconnier

et al. 2012

Process Biochemistry

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a b s t r a c tFollowing a promising preliminary study concerning sugar beet leaves valorization and to fulfill the high demand in natural C 6 -aldehydes flavors, an efficient biocatalytic reaction was developed to synthesize (2E)-hexenal at large scale. As major product of the lipoxygenase enzyme, 13-HPOT was converted by sugar beet hydroperoxide lyase extracted from leaves or expressed by recombinant Escherichia coli strains. With the adaptation of a fed-batch substrate addition and a continuous extraction of volatiles, 3.46 mM and 1.37 mM of C 6 -aldehydes were produced with the native hydroperoxide lyase at respectively 2 and 100 L scale. Furthermore, higher molar productivity of green leaf volatiles was reached with recombinant hydroperoxide lyase (5.5 mM at 2 L scale) while no others side products from the lipoxygenase pathway were formed. Once purified, these natural aromas are suitable for food and beverage preparations, perfumes or cosmetic products.

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Section: Introductionmentioning

confidence: 99%

Optimization and scaling up of a biotechnological synthesis of natural green leaf volatiles using Beta vulgaris hydroperoxide lyase

Gigot

Ongena

Fauconnier

et al. 2012

Process Biochemistry

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“…There is a possible parallel to a pasture diet for cattle. Linolenic acid dominates the fatty acid profile of pasture (Hitchcock & Nichols 1971;Black 1981), and lipoxygenase is present in the green leaves of clover and alfalfa (Sekiya et al 1983). Therefore, the presence of 4-heptenal may indicate exposure at some time to a pasture diet.…”

Section: Possible Causes Of Pastoral Flavourmentioning

confidence: 99%

The effect of diet on the flavour of cooked beef and the odour compounds in beef fat

Young¹,

Baumeister²

1999

New Zealand Journal of Agricultural Research

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Fatty meat from cattle finished for nine weeks on ryegrass/clover or maize was evaluated for intensity of pastoral odour and flavour by a sensory panel. Although there was no significant treatment effect for intensity, panellists' comments indicated that even this short period on a maize diet could change descriptions of odour and flavour; when assessed by independent assessors, the pasture treatment had a much lower ratio of "favourable" to "unfavourable" comments (P < 0.01). Odorous compounds in fat from the two treatments were examined by odourport sniffing, where compounds eluting from a gas chromatographic column were described, and identified where possible. Two "sniffers" semiquantitatively evaluated the fat volatiles, first trapped on Tenax then resolved on a column. Comparisons between treatments were largely unproductive. However, particularly odorous compounds were tentatively identified along with others of interest with respect to dietary origins. Compounds included 4-heptenal (and/or the coeluant heptanal), l-octen-3-ol, nonanal, 2,6-nonadienal, nonanoic acid, and the faecal-smelling compound indole. 4-Methylphenol was not detected by sniffing but was present in the fat headspace. The chemical origins of these compounds are discussed in relation to diet. A98056

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“…HPLS activity has been reported in soybean leaves (23), and from soybean seeds and seedlings the enzyme has been partially characterized (17,20) and purified (20). During development of the soybean seed, HPLS activity continues to decrease and lipoxygenase levels increase (24).…”

mentioning

confidence: 99%

Hydroperoxide Lyase and Other Hydroperoxide-Metabolizing Activity in Tissues of Soybean, Glycine max

Gardner¹,

Weisleder²,

Plattner³

1991

Plant Physiol.

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Hydroperoxide lyase (HPLS) activity in soybean (Glycine max) seed/seedlings, leaves, and chloroplasts of leaves required detergent solubilization for maximum in vitro activity. On a per milligram of protein basis, more HPLS activity was found in leaves, especially chloroplasts, than in seeds or seedlings. The total yield of hexanal from 13(S)-hydroperoxy-cis-9,trans-1 1-octadecadienoic acid (13S-HPOD) from leaf or chloroplast preparations was 58 and 66 to 85%, respectively. Because of significant competing hydroperoxide-metabolizing activities from other enzymes in seed/seedling preparations, the hexanal yields from this source were lower (36-56%). Some of the products identified from the seed or seedling preparations indicated that the competing activity was mainly due to both a hydroperoxide peroxygenase and reactions catalyzed by lipoxygenase. Different HPLS isozyme compositions in the seed/seedling versus the leaf/chloroplast preparations were indicated by differences in the activity as a function of pH, the Km values, relative V .. with 13S-HPOD and 13(S)-hydroperoxy-cis-9,trans-1 ,cis-15-octadecatrienoic acid (13S-HPOT), and the specificity with different substrates. With regard to the latter, both seed/seedling and chloroplast HPLS utilized the 13S-HPOD and 13S-HPOT substrates, but only seeds/ seedlings were capable of metabolizing 9(S)-hydroperoxy-trans-10,cis-12-octadecadienoic acid into 9-oxononanoic acid, isomenc nonenals, and 4-hydroxynonenal. From 13S-HPOD and 13S-HPOT, the products were identified as 12-oxo-cis-9-dodecenoic acid, as well as hexanal from 13S-HPOD and cis-3-hexenal from 13S-HPOT. In seed preparations, there was partial isomerization of the cis-3 or cis-9 into trans-2 or trans-10 double bonds, respectively.HPLS', an enzyme that cleaves hydroperoxides of polyunsaturated fatty acids into both aldehyde and w-oxoacid fragments, occurs widely in plants. Depending on substrate specificity of HPLS isoenzymes for isomeric hydroperoxides of linoleic or linolenic acids, the enzyme produces either green/ ' Abbreviations: HPLS, hydroperoxide lyase; CP-HPLC, chiralphase HPLC; El, electron impact; OTMS, trimethylsilyloxy; rac-HPOD, racemic cis,trans-and trans,trans-diene linoleic acid hydroperoxides; rac-HPOT, racemic cis,cis,trans-triene linolenic acid hydroperoxides; 9S-HPOD, 9(S)-hydroperoxy-trans-10,cis-12-octadecadienoic acid; 13S-HPOD, 13(S)-hydroperoxy-cis-9,trans-11-octadecadienoic acid; 12S-HPOT, 12(S)-hydroperoxy-cis-9,trans-13,cis-1 5-octadecatrienoic acid; 1 3S-HPOT, 1 3(S)-hydroperoxy-cis-9,trans-11 ,cis-5-octadecatrienoic acid; SP-HPLC, straight-phase HPLC; Triton X-1 OOR, Triton X-100 reduced; m/z, mass to charge ratio. beany/grassy odors (hexanal or cis-3-hexenal) from 1 3-hydroperoxides or cucumber/pear odors (cis-3-nonenal or cis-3,cis-6 nonadienal) from 9-hydroperoxides (reviewed in refs. 4 and 15). The corresponding w-oxoacid fragments, 12-oxo-cis-9-dodecenoic acid and 9-oxononanoic acid, have no known function, except the former isomerizes into 12-oxo-trans-10-dodecenoi...

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Distribution of lipoxygenase and hydroperoxide lyase in the leaves of various plant species

Cited by 52 publications

References 11 publications

Optimization and scaling up of a biotechnological synthesis of natural green leaf volatiles using Beta vulgaris hydroperoxide lyase

Optimization and scaling up of a biotechnological synthesis of natural green leaf volatiles using Beta vulgaris hydroperoxide lyase

The effect of diet on the flavour of cooked beef and the odour compounds in beef fat

Hydroperoxide Lyase and Other Hydroperoxide-Metabolizing Activity in Tissues of Soybean, Glycine max

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