Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1

Bouwmeester, Harro J.; Gershenzon, Jonathan; Konings, Maurice; Croteau, Rodney

doi:10.1104/pp.117.3.901

Cited by 147 publications

(51 citation statements)

References 32 publications

(49 reference statements)

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“…A desprotonação do C8 do cátion α-terpinílico [9] favorece a produção do limoneno [10], 14,20 cuja hidroxilação por enzimas do citocromo P-450 origina o E-carveol [11]. 15,20,23,24 Quando a saída do próton ocorre no C6, forma-se o terpinoleno [13] 14 que, por isomerização, passaria a isoterpinoleno [14]. Muitos terpenóides são produtos diretos das enzimas terpeno-sintetases, enquanto outros são obtidos após transformações secundárias, 15 o que parece ser o caso do isoterpinoleno [14].…”

Section: Resultsunclassified

“…A desprotonação do cátion pinílico [20] no C4 e/ou C10 conduz, respectivamente, ao α-pineno [21] e/ou β-pineno [22]. 20,21,22,27 As ações das enzimas do citocromo P-450 15,36 sobre o β-pineno [22], em um processo análogo à biossíntese da carvona, 20,23,24 formam o pinocarveol [23], cuja desidrogenação oxidativa resulta na pinocarvona [24] 36 (Esquema 1). Um rearranjo do cátion bornílico [25] do tipo Wagner-Meerwein gera o cátion canfílico [26] que, por desprotonação do C10, leva ao canfeno [27].…”

Section: Resultsunclassified

“…26,34 Em contrapartida, a acilação enzimática do borneol [29], em semelhança ao que ocorre com outras substâncias, 15 resultaria no acetato de isobornila [31] (Esquema 1). [2] Cátion linalílico, [2'] Cátion linalílico/isômero [3] E-β-Ocimeno, [4] Linalol, [5] 6,7 Epóxido de linalol, [6] Óxido de linalol, [7] Difosfato de linalila (LPP), [7'] Difosfato de linalila (LPP)/isômero, [8] β-Mirceno, [9] Cátion α-terpinílico, [10] Limoneno, [11] E-carveol, [12] Isolimoneno, [13] Terpinoleno, [14] Isoterpinoleno, [15] α-Tujona, [16] Sabineno, [17] Z-Hidrato de sabineno, [18] α-Terpineol, [19] 1,8-Cineol, [20] Cátion pinílico, [21] α-Pineno, [22] β-Pineno, [23] Pinocarveol, [24] Pinocarvona, [25] Cátion bornílico, [26] Cátion canfílico, [27] Canfeno, [28] Difosfato de bornila, [29] Borneol, [30] Cânfora, [31] Acetato de isobornila, [32] Difosfato de farnesila (FPP), [33] Cátion difosfato farnesílico, [34] E-β-Farneseno, [35] [37] Cátion difosfato nerolídico (NPP), [37'] Cátion difosfato nerolidílico/isômero, [38]…”

Section: Resultsunclassified

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Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae)

Barros¹,

Zambarda²,

Heinzmann³

et al. 2009

Quím. Nova

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Recebido em 26/2/08; aceito em 22/10/08; publicado na web em 6/3/09 SEASONAL VARIABILITY AND TERPENOID BIOSYNTHESIS OF THE ESSENTIAL OIL OF Lippia alba (Mill.) N. E. BROWN (VERBENACEAE). The essential oil of the leaves of Lippia alba chemotype linalool-1,8-cineol was extracted by hidrodistillation at different seasons and analyzed by GC/MS. Qualitative and quantitative variations in regard to the period of harvesting have been performed and the results were correlated with meteorological data. The essential oil yield varied from 0.33 to 0.67%. The chemical diversity of the constituents increased throughout the year, being 1,8-cineol and linalool the major components. Possible biosynthetic routes of mono and sesquiterpenoids present in the essential oil are discussed.Keywords: Lippia alba; terpenoids; seasonal variability. introdUÇÃoLippia alba (Mill.) N. E. Brown (Verbenaceae) é uma planta medicinal nativa da América do Sul, conhecida popularmente como falsa-melissa.1 Infusões, banhos e xaropes, preparados com suas folhas ou raízes, são utilizados na medicina popular para o tratamento de distúrbios estomacais, afecções das vias respiratórias, no combate à hipertensão e como sedativo. 2Entre os metabólitos secundários descritos para L. alba encontram-se flavonóides, taninos, iridóides, saponinas triterpênicas, resinas, mucilagens e óleo essencial. 3Variações qualitativas e quantitativas dos principais componentes do óleo essencial desta espécie têm levado a sua separação em quimiotipos ou raças químicas: citral, 4,5 carvona, 4 linalol -1, 8-cineol, 6 entre outros. Adicionalmente, a influência de fatores abióticos como luz, temperatura, água, solo e altitude sobre a biossíntese de certos constituintes vegetais, especialmente os terpenóides, foi comprovada em diferentes espécies vegetais. 7 A variabilidade na composição do óleo essencial das folhas de L. alba foi demonstrada anteriormente em função das diferentes regiões do ramo vegetal, 5 das épocas e horários de coleta, 5,6,8 bem como da metodologia empregada na sua extração. 9No entanto, até o momento, não há trabalhos publicados interligando, por meio de dados meteorológicos, as variações observadas aos fatores abióticos. O presente trabalho teve como objetivo avaliar a variação do teor e da composição química do óleo essencial das folhas de L. alba, provenientes de cultivo e coletadas nas diferentes estações do ano, relacionando as variações observadas com dados meteorológicos de temperatura, insolação, umidade relativa e chuva acumulada. As possíveis rotas biossintéticas para os mono e sesquiterpenóides presentes no óleo essencial também são discutidas.

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Section: Resultsunclassified

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Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae)

Barros¹,

Zambarda²,

Heinzmann³

et al. 2009

Quím. Nova

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“…Enzymes in this family also catalyze the transfer of other acyl groups; for example, from benzoyl-CoA to benzyl alcohol to produce benzylbenzoate in flowers of Clarkia breweri, a California annual (20). Members of another large group of enzymes, the oxidoreductases, have been found to catalyze the oxidation of the monoterpene carveol to carvone (caraway spice) and the reduction of medium-chain fatty acid aldehydes to alcohols (27,28).…”

Section: Enzymes For the Biosynthesis Of Pvs Often Belong To Large Famentioning

confidence: 99%

Biosynthesis of Plant Volatiles: Nature's Diversity and Ingenuity

Pichersky

Noel

Dudareva

2006

Science

836

525

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Plant volatiles (PVs) are lipophilic molecules with high vapor pressure that serve various ecological roles. The synthesis of PVs involves the removal of hydrophilic moieties and oxidation/ hydroxylation, reduction, methylation, and acylation reactions. Some PV biosynthetic enzymes produce multiple products from a single substrate or act on multiple substrates. Genes for PV biosynthesis evolve by duplication of genes that direct other aspects of plant metabolism; these duplicated genes then diverge from each other over time. Changes in the preferred substrate or resultant product of PV enzymes may occur through minimal changes of critical residues. Convergent evolution is often responsible for the ability of distally related species to synthesize the same volatile.Plant volatiles (PV) are typically lipophilic liquids with high vapor pressures. Nonconjugated PVs can cross membranes freely and evaporate into the atmosphere when there are no barriers to diffusion. The number of identified volatile chemicals synthesized by various plants exceeds 1000 and is likely to grow as more plants are examined with new methods for detecting and analyzing quantities of volatiles that are often minute (1-3).PVs serve multiple functions in both floral and vegetative organs, and these roles are not always related to their volatility (1). Most PVs are restricted to specific lineages and are involved in species-specific ecological interactions, leading to their designation as specialized, or secondary, metabolites (4). To humans, pollinator-attracting floral scents have been a source of olfactory pleasure since antiquity, and we also use a large number of aromatic plants as flavorings, preservatives, and herbal remedies (5). Flower and herb aromas may contain many individual chemicals, sometimes with very little overlap in the PV profiles of even closely related species (6). It is unlikely that the observed differences are due entirely to differential gene expression. That most PVs are restricted to a few lineages, both ancient and derived, argues for frequent changes in enzymatic profiles through evolution. Considerable diversity and fast rates of change have also been observed in nonvolatile specialized metabolites in plants, raising similar questions regarding the underlying evolutionary mechanisms (7).Improvements in analytical techniques and molecular and biochemical methods have made PVs one of the best-studied groups of plant secondary metabolites. Here we describe

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“…Second, this intermediate is either stored in the essential oil ductus without further metabolism or is converted by limonene-6-hydroxylase to trans-carveole. Third, trans-carveole is oxidized by a dehydrogenase to trans-carvone (Bouwmeester et al 1998). At the enzyme level, the hydroxylation of limonene to trans-carveole seems to be a critical, rate limiting step in carvone biosynthesis.…”

Section: Essential Oil Constituentsmentioning

confidence: 99%

Evaluation of caraway essential oil from different production areas of Serbia

Aćimović¹,

Oljača²,

Tešević³

et al. 2014

Hortic. Sci.

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Caraway fruits contain essential oils that give caraway its characteristic aroma. This paper evaluates quantity and composition of the essential oil from the annual caraway grown in different production areas of Serbia. Experiments were conducted in three production areas: Banat, Bačka and Srem, during two years. The fruits contained 3.95% of oil on average. The highest content of essential oil was obtained in the production area of Banat, a part of Serbia where environmental conditions are very favourable for cultivation of medicinal plants. Weather conditions have not a significant influence on the content of essential oil in caraway fruits. However, weather conditions as well as production region had a great influence on seed yield and essential oil yield. There were 22 compounds determined in caraway essential oil by GC/MS. The main components were carvone and limonene, whose mixture constituted from 97.69 to 98.62% of total oil composition. Carvone/limonene ratio was 0.58% on average, therefore, it can be concluded that this annual caraway belongs to limonene chemotype.

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Biosynthesis of the Monoterpenes Limonene and Carvone in the Fruit of Caraway1

Cited by 147 publications

References 32 publications

Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae)

Variabilidade sazonal e biossíntese de terpenóides presentes no óleo essencial de Lippia alba (Mill.) N. E. Brown (Verbenaceae)

Biosynthesis of Plant Volatiles: Nature's Diversity and Ingenuity

Evaluation of caraway essential oil from different production areas of Serbia

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