Alfalfa contains substantial 9‐hydroperoxide lyase activity and a 3<i>Z</i>:2<i>E</i>‐enal isomerase

Noordermeer, Minke A.; Veldink, Gerrit A.; Vliegenthart, Johannes F.G.

doi:10.1016/s0014-5793(98)01706-2

Cited by 67 publications

(55 citation statements)

References 23 publications

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“…The results presented here on the endogenous amounts of these isomers, their formation in plant extracts together with the data obtained for the recombinant garlic enzyme indicate that the trans-isomers are direct products of AsDES. In contrast, the formation of the cis-isomer is not due to AsDES activity, but rather catalyzed by a yet not identified isomerase activity as has been described for the isomerization of HPL products where (3Z)-aldehydes are converted into (2E)-aldehydes [22]. In general DES activity appears to be characteristic for certain genera of plants, whereas AOS and HPL are widely distributed within the plant kingdom.…”

Section: Discussionmentioning

confidence: 89%

Lipid metabolism in arbuscular mycorrhizal roots of Medicago truncatula

Stumpe¹,

Carsjens²,

Stenzel

et al. 2005

Phytochemistry

117

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Section: Discussionmentioning

confidence: 89%

Lipid metabolism in arbuscular mycorrhizal roots of Medicago truncatula

Stumpe¹,

Carsjens²,

Stenzel

et al. 2005

Phytochemistry

117

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“…This HPO lyase from alfalfa is highly specific for 13-hydroperoxy linoleic and linolenic acids. A crude extract of alfalfa was prepared as described previously (7).…”

Section: Methodsmentioning

confidence: 99%

Oxygenation of (3Z)-Alkenals to 4-Hydroxy-(2E)-Alkenals in Plant Extracts: A Nonenzymatic Process

Noordermeer

Feußner

Kolbe

et al. 2000

Biochemical and Biophysical Research Communications

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There is large interest in 4-hydroxy-(2E)-alkenals because of their cytotoxicity in mammals. However, the biosynthetic pathway for these compounds has not been elucidated yet. In plants, 4-hydroxy-(2E)-alkenals were supposed to be derived by the subsequent actions of lipoxygenase and a peroxygenase on (3Z)-alkenals. The presence of 9-hydroxy-12-oxo-(10E)-dodecenoic acid (9-hydroxy-traumatin) in incubations of 12-oxo-(9Z)-dodecenoic acid (traumatin) in the absence of lipoxygenase or peroxygenase, has prompted us to reinvestigate its mode of formation. We show here that in vitro 9-hydroxy-traumatin, 4-hydroxy-(2E)-hexenal and 4-hydroxy-(2E)-nonenal, are formed in a nonenzymatic process. Furthermore, a novel product derived from traumatin was observed and identified as 11-hydroxy-12-oxo-(9Z)-dodecenoic acid. The results obtained here strongly suggest that the 4-hydroxy-(2E)-alkenals, observed in crude extracts of plants, are mainly due to autoxidation of (3Z)-hexenal, (3Z)-nonenal and traumatin. This may have implications for the in vivo existence and previously proposed physiological significance of these products in plants.

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“…Although 3Z,2E-enal isomerase activity has been described in soybeans (Glycine max L.) and alfalfa (Medicago sativa L.), neither a protein nor a corresponding gene has been cloned yet (Noordermeer et al, 1999;Takamura and Gardner, 1996). C 6 and C 9 aldehydes can be further metabolized by ADH to form the corresponding alcohols.…”

Section: Fatty Acid-derived and Other Lipophylic Flavor Compoundsmentioning

confidence: 99%

Biosynthesis of plant‐derived flavor compounds

Schwab¹,

Davidovich‐Rikanati²,

Lewinsohn³

2008

The Plant Journal

944

704

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SummaryPlants have the capacity to synthesize, accumulate and emit volatiles that may act as aroma and flavor molecules due to interactions with human receptors. These low-molecular-weight substances derived from the fatty acid, amino acid and carbohydrate pools constitute a heterogenous group of molecules with saturated and unsaturated, straight-chain, branched-chain and cyclic structures bearing various functional groups (e.g. alcohols, aldehydes, ketones, esters and ethers) and also nitrogen and sulfur. They are commercially important for the food, pharmaceutical, agricultural and chemical industries as flavorants, drugs, pesticides and industrial feedstocks. Due to the low abundance of the volatiles in their plant sources, many of the natural products had been replaced by their synthetic analogues by the end of the last century. However, the foreseeable shortage of the crude oil that is the source for many of the artifical flavors and fragrances has prompted recent interest in understanding the formation of these compounds and engineering their biosynthesis. Although many of the volatile constituents of flavors and aromas have been identified, many of the enzymes and genes involved in their biosynthesis are still not known. However, modification of flavor by genetic engineering is dependent on the knowledge and availability of genes that encode enzymes of key reactions that influence or divert the biosynthetic pathways of plant-derived volatiles. Major progress has resulted from the use of molecular and biochemical techniques, and a large number of genes encoding enzymes of volatile biosynthesis have recently been reported.

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Alfalfa contains substantial 9‐hydroperoxide lyase activity and a 3Z:2E‐enal isomerase

Cited by 67 publications

References 23 publications

Lipid metabolism in arbuscular mycorrhizal roots of Medicago truncatula

Lipid metabolism in arbuscular mycorrhizal roots of Medicago truncatula

Oxygenation of (3Z)-Alkenals to 4-Hydroxy-(2E)-Alkenals in Plant Extracts: A Nonenzymatic Process

Biosynthesis of plant‐derived flavor compounds

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