Biosynthetic pathway for C6-aldehydes formation from linolenic acid in green leaves

Hatanaka, Akikazu; Kajiwara, Tadahiko; Sekiya, Jiro

doi:10.1016/0009-3084(87)90057-0

Cited by 178 publications

(117 citation statements)

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“…Lipoxygenase might be involved in seed deterioration (Bewley, 1986) because it catalyzes the incorporation of molecular oxygen into fatty acids containing a (Z, Z) -l, 4-pentadiene moiety and generates free radicals (Hatanaka et al, 1987;Vick and Zimmerman, 1987). The ability of lipoxygenase to generate free radicals and oxidize polyunsaturated fatty acids suggest that lipoxygenase might contribute to seed deterioration by disrupting membrane integrity.…”

Section: Resultsmentioning

confidence: 99%

Changes of enzymes activities in botanical treated aged seed of soybean (Glycine max (L.) Merrill) cv. CO 3 seeds

Rejeendran

Lakshmi

Ambika

2017

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Changes occurring in seed during aging are very significant for determining seed quality, i.e. seed longevity. An experiment was conducted in Department of Seed Science and Technology, TNAU, Coimbatore to standardize suitable seed dry dressing treatments, using near nano size botanicals that can alleviate the deleterious effect of accelerated ageing and to improve the enzyme activities of soybean aged seeds. Five days aged seeds were treated with 1 h ball milled fenugreek seed powder, leaf powders of ashwagandha, tea and noni @ 2 g kg -1 with 60 min. shaking and evaluated for enzyme activities and field emergence (naturally and artificially aged seeds). Among the treatments seeds treated with fenugreek seed powder has the highest dehydrogenase activity (OD 10 min -1 ), protein (%), oil content (%), catalase activity, peroxidase activity (OD 10 min -1 ) (µg H 2 O 2 mg -1 min -1 ) with minimum values of electrical conductivity (dSm -1 ), free fatty acid (%), lipid peroxidation (OD value), lipoxygenase activity (g mol s -1 mg -1 ). Field emergence (%) was also higher in fenugreek seed powder treated seeds (2 g kg -1 with 60 min).

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Section: Resultsmentioning

confidence: 99%

Changes of enzymes activities in botanical treated aged seed of soybean (Glycine max (L.) Merrill) cv. CO 3 seeds

Rejeendran

Lakshmi

Ambika

2017

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“…Tale studio ha dimostrato che i componenti principali della frazione volatile di F. arundinacea sono alcoli, aldeidi ed esteri a sei atomi di carbonio, fra cui cis-3-esenolo, trans-2-esenale e cis-3-esenil acetato sono i più rappresentativi. Questi composti sono caratteristici e tipici dell'odore di erba appena falciata, e sono prodotti in tutti i tessuti vegetali per rottura enzimatica della catena dell'acido linolenico (Hatanaka et al, 1987). L'indagine non ha mostrato differenze qualitative nella composizione dei volatili nelle diverse cultivars esaminate, ma ha evidenziato una notevole variabilità del loro contenuto durante la stagione di crescita (cis-3-esenolo 2.0-7.7 µg/g, trans-2-esenale 0.4-1.5 µg/g e cis-3-esenil acetato 0.3-1.2 µg/g, calcolati sul peso del materiale fresco).…”

Section: Sostanze Volatiliunclassified

Secondary metabolites in grasses: characterization and biological activity

Tava¹

2007

Ital J Agronomy

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RiassuntoNell'ambito di indagini sul valore nutrizionale di specie foraggere, si è dato sempre più ampio spazio allo studio di componenti minori, definiti metaboliti secondari, che possono influenzare alcuni aspetti nutrizionali del foraggio. Infatti, accanto ai componenti principali, protidi, glucidi, lipidi, fibre, che ne determinano le caratteristiche nutrizionali, vi sono i metaboliti secondari che ne possono influenzare, in alcuni casi, l'utilizzo. Il nome metaboliti secondari, deriva dal fatto che queste sostanze sono presenti nella pianta in concentrazione molto inferiore rispetto agli altri costituenti principali, ma sono indispensabili alla pianta stessa perchè entrano a far parte dei suoi complessi processi fisiologici. Queste sostanze sono spesso dotate di particolari attività biologiche e ciò li rende importanti dal punto di vista nutrizionale ed interessanti anche per il loro possibile utilizzo in ambito farmacologico. Nel presente lavoro sono riportati i vari metaboliti indagati, nonché indicazioni sui metodi di analisi, la loro presenza nel materiale vegetale e la loro attività biologica.Parole chiave: metaboliti secondari, sostanze volatili, saponine, inibitori di proteasi, fitoestrogeni, glucosidi cianogenici, alcaloidi. Summary SECONDARY METABOLITES IN GRASSES: CHARACTERIZATION AND BIOLOGICAL ACTIVITYIn a series of studies dealing on the nutritional value of forage species, more attention was focussed on several compounds, named secondary metabolites, that are important in determining nutritional characteristics. Secondary metabolites are compounds detected in the green materials in low concentration compared to primary metabolites (proteins, sugars, lipids, fibers), but of fundamental importance for the plant physiology. The possess several biological activities and this contribute to their possible pharmacological use. In the present paper studies on secondary metabolites from herbaceous plants are reviewed. Indications of the chemical methods used for their analyses, their presence in the green material and their biological activity are also reported.

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“…C6-aldehydes are major volatile compounds produced by injured leaves of many species of plants. C6-aldehydes are formed via the LOX2 pathway (11). When plant leaves are damaged by wounding or freezing, the unsaturated fatty acids linoleic acid and/or linolenic acid can be rapidly dioxygenated by LOX into 13-hydroperoxy fatty acids.…”

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confidence: 99%

“…Cis-3-hexenal is usually isomerized to trans-2-hexenal both enzymically and nonenzymically. These C6-aldehydes are responsible for the 'green' odor of leaves (11).…”

mentioning

confidence: 99%

“…Although the pathway leading to the formation of C6-compounds in plant leaves has been well understood (11), the control of C6-compound formation in leaves is not yet clear. Previous results showed that the environmental factors of temperature and solar radiation appeared to influence C6-compound formation in leaves, and it was suggested that changes in LOX activity were responsible for the seasonal variation in C6-aldehyde formation in tea leaves (18,20).…”

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confidence: 99%

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Developmental Change in C₆-Aldehyde Formation by Soybean Leaves

Zhuang

Hamilton-Kemp²,

Andersen³

et al. 1992

Plant Physiol.

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Damage to plant leaves by wounding or freezing induces the production of large amounts of C6-compounds. However, the control of formation of these compounds in leaves is not yet clear. In the current study, C6-aldehyde formation by freeze-injured soybean leaves of different ages (based on the leaf positions on the plant) at stage Rl of plant development was investigated. The results demonstrate that C6-aldehyde formation by the soybean (Glycine max L.) leaves changes as leaves develop. Younger leaves produce high levels of C6-aldehydes, mainly composed of hexanal.Subsequently, as the leaves develop, the level of C6-aldehyde formation decreases markedly, followed by an increase with a large shift from hexanal to hexenals. Lipoxygenase and lipolytic acyl hydrolase activity was reduced, and, in contrast, hydroperoxide lyase activity increased. There was little difference in lipoxygenase substrate specificity for linoleic acid and linolenic acid, but hydroperoxide lyase preferentially utilized 13-hydroperoxy-9,11,15-octadecatrienoic acid. In the in vivo lipoxygenase substrate pool, the linoleic acid level declined and the relative level of linolenic acid increased. The change in ratios of linolenic acid to linoleic acid showed a similar trend during soybean leaf development to that of hexenals to hexanal. C6-aldehydes are major volatile compounds produced by injured leaves of many species of plants. C6-aldehydes are formed via the LOX2 pathway (11). When plant leaves are damaged by wounding or freezing, the unsaturated fatty acids linoleic acid and/or linolenic acid can be rapidly dioxygenated by LOX into 13-hydroperoxy fatty acids. These hydroperoxides can be cleaved by HPL to form the C6- ' The investigation reported in this paper ) is in connection with a project of the Kentucky Agricultural Experiment Station and published with approval of the Director. 2Abbreviations: LOX, lipoxygenase; BHT, butylated hydroxytoluene (2,6-di-tert-butyl-p-cresol); DGD, digalactosyldiacylglycerol; FFA, free fatty acid; 17:0, heptadecanoic acid; HPL, hydroperoxide lyase; 13-HPOD, 13-hydroperoxy-9,11-octadecadienoic acid; 9-HPOT, 9-hydroperoxy-9,11,15-octadecatrienoic acid; 13-HPOT, 13-hydroperoxy-9,11,15-octadecatrienoic acid; 18:2, linoleic acid; 18:3, linolenic acid; LAH, lipolytic acyl hydrolase; -L1, a null for LOX 1; -L1L3, a null for LOX 1 and LOX 3; -L2, a null for LOX 2; -L2L3, a null for LOX 2 and LOX 3; -L3, a null for LOX 3; MGD, monogalactosyldiacylglycerol; 18:1, oleic acid; 16:0, palmitic acid; PC, phosphatidylcholine; 18:0, stearic acid; TFA, total fatty acid; TG, triacylglycerol. aldehydes hexanal and/or cis-3-hexenal. Cis-3-hexenal is usually isomerized to trans-2-hexenal both enzymically and nonenzymically. These C6-aldehydes are responsible for the 'green' odor of leaves (11).C6-aldehydes were first reported in green leaves about 80 years ago (1). Although the pathway leading to the formation of C6-compounds in plant leaves has been well understood (11), the control of C6-compound formation in leaves i...

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Biosynthetic pathway for C6-aldehydes formation from linolenic acid in green leaves

Cited by 178 publications

References 49 publications

Changes of enzymes activities in botanical treated aged seed of soybean (Glycine max (L.) Merrill) cv. CO 3 seeds

Changes of enzymes activities in botanical treated aged seed of soybean (Glycine max (L.) Merrill) cv. CO 3 seeds

Secondary metabolites in grasses: characterization and biological activity

Developmental Change in C₆-Aldehyde Formation by Soybean Leaves

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Biosynthetic pathway for C6-aldehydes formation from linolenic acid in green leaves

Cited by 178 publications

References 49 publications

Changes of enzymes activities in botanical treated aged seed of soybean (Glycine max (L.) Merrill) cv. CO 3 seeds

Changes of enzymes activities in botanical treated aged seed of soybean (Glycine max (L.) Merrill) cv. CO 3 seeds

Secondary metabolites in grasses: characterization and biological activity

Developmental Change in C6-Aldehyde Formation by Soybean Leaves

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Product

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Developmental Change in C₆-Aldehyde Formation by Soybean Leaves