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PubMed2025

Genomic mechanism of aroma terpenoids biosynthesis in plants.

BACKGROUND: Aroma terpenoids are crucial plant secondary metabolites with physiological and commercial importance. Interestingly, both closely and distantly related species can synthesize identical aroma terpenoids. With the development of genome sequencing technology, it has become possible to elucidate the genomic mechanism underlying this phenomenon. AIM: This review highlights whole-genome data as a robust strategy for investigating the genomic mechanism of aroma terpenoids biosynthesis in plants, and provides new perspectives on the origin, evolution, and engineering of terpene synthases (TPSs). This aims to significantly benefit plant breeding and enhance suitability for industrial production. KEY SCIENTIFIC CONCEPTS OF REVIEW: Genomic mechanism of aroma terpenoids biosynthesis in plant genomes is the genetic and evolutionary dynamics. We elaborate the genomic mechanism governing the biosynthesis of plant-derived aroma terpenoids in three dimensions: (1) Genome-wide identification and phylogenetic analyses of TPSs. The same aroma terpenoids were produced by numerous plant species with chromosome-level genomes. Based on 34 plant genomes, we identified 1643 TPSs and classified them into seven subfamilies. (2) Functional and structural basis of TPSs. We found that TPSs with identical functions in distant species exhibit low sequence similarity but conserved active cavity architectures. Conversely, functionally distinct TPSs in closely related species cluster phylogenetically but differ in active cavity structures. (3) Patterns of TPS gene origination. Comparative genomic analyses within and between species revealed three patterns enabling TPSs to acquire the same functions: tandem duplications, dispersed duplications, and genes without duplication.

Terpenes↗
PubMed2003

Biotransformation of hop aroma terpenoids by ale and lager yeasts.

Terpenoids are important natural flavour compounds, which are introduced to beer via hopping. It has been shown recently that yeasts are able to biotransform some monoterpene alcohols. As a first step towards examining whether yeasts are capable of altering hop terpenoids during the brewing of beer, we investigated whether they were transformed when an ale and lager yeast were cultured in the presence of a commercially available syrup. Both yeasts transformed the monoterpene alcohols geraniol and linalool. The lager yeast also produced acetate esters of geraniol and citronellol. The major terpenoids of hop oil, however, were not biotransformed. Oxygenated terpenoids persisted much longer than the alkenes.

Acyclic Monoterpenes↗
PubMed2001

Enhanced levels of the aroma and flavor compound S-linalool by metabolic engineering of the terpenoid pathway in tomato fruits.

The aromas of fruits, vegetables, and flowers are mixtures of volatile metabolites, often present in parts per billion levels or less. We show here that tomato (Lycopersicon esculentum Mill.) plants transgenic for a heterologous Clarkia breweri S-linalool synthase (LIS) gene, under the control of the tomato late-ripening-specific E8 promoter, synthesize and accumulate S-linalool and 8-hydroxylinalool in ripening fruits. Apart from the difference in volatiles, no other phenotypic alterations were noted, including the levels of other terpenoids such as gamma- and alpha-tocopherols, lycopene, beta-carotene, and lutein. Our studies indicate that it is possible to enhance the levels of monoterpenes in ripening fruits by metabolic engineering.

Acyclic Monoterpenes↗
PubMed2003

Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene.

Citrus fruits possess unique aromas rarely found in other fruit species. While fruit flavor is composed of complex combinations of soluble and volatile compounds, several low-abundance sesquiterpenes, such as valencene, nootkatone, alpha-sinensal, and beta-sinensal, stand out in citrus as important flavor and aroma compounds. The profile of terpenoid volatiles in various citrus species and their importance as aroma compounds have been studied in detail, but much is still lacking in our understanding of the physiological, biochemical, and genetic regulation of their production. Here, we report on the isolation, functional expression, and developmental regulation of Cstps1, a sesquiterpene synthase-encoding gene, involved in citrus aroma formation. The recombinant enzyme encoded by Cstps1 was shown to convert farnesyl diphosphate to a single sesquiterpene product identified as valencene by gas chromatography-mass spectrometry (GC-MS). Phylogenetic analysis of plant terpene synthase genes localized Cstps1 to the group of angiosperm sesquiterpene synthases. Within this group, Cstps1 belongs to a subgroup of citrus sesquiterpene synthases. Cstps1 was found to be developmentally regulated: transcript was found to accumulate only towards fruit maturation, corresponding well with the timing of valencene accumulation in fruit. Although citrus fruits are non-climacteric, valencene accumulation and Cstps1 expression were found to be responsive to ethylene, providing further evidence for the role of ethylene in the final stages of citrus fruit ripening. Isolation of the gene encoding valencene synthase provides a tool for an in-depth study of the regulation of aroma compound biosynthesis in citrus and for metabolic engineering for fruit flavor characteristics.

Alkyl and Aryl Transferases↗
PubMed2005

Analysis of hop-derived terpenoids in beer and evaluation of their behavior using the stir bar-sorptive extraction method with GC-MS.

Hop aroma components, which mainly comprise terpenoids, contribute to the character of beers. However, pretreatments are necessary before analyzing these components because of their trace levels and complicated matrixes. Here, the stir bar-sorptive extraction (SBSE) method was used to detect and quantify many terpenoids simultaneously from small samples. This simple technique showed low coefficients of variation, high accuracy, and low detection limits. An investigation of the behavior of terpenoids identified two distinct patterns of decreasing concentration during wort boiling. The first, which was seen in myrcene and linalool, involved a rapid decrease that was best fitted by a quadratic curve. The second, which was observed in beta-eudesmol, humulene, humulene epoxide I, beta-farnesene, caryophyllene, and geraniol, involved a gentle linear decrease. Conversely, the concentration of beta-damascenone increased after boiling. As the aroma composition depended on the hop variety, we also examined the relationship between terpenoid content and sensory analysis in beer.

Beer↗
PubMed2004

Circadian regulation of the PhCCD1 carotenoid cleavage dioxygenase controls emission of beta-ionone, a fragrance volatile of petunia flowers.

Carotenoids are thought to be the precursors of terpenoid volatile compounds that contribute to flavor and aroma. One such volatile, beta-ionone, is important to fragrance in many flowers, including petunia (Petunia hybrida). However, little is known about the factors regulating its synthesis in vivo. The petunia genome contains a gene encoding a 9,10(9',10') carotenoid cleavage dioxygenase, PhCCD1. The PhCCD1 is 94% identical to LeCCD1A, an enzyme responsible for formation of beta-ionone in tomato (Lycopersicon esculentum; Simkin AJ, Schwartz SH, Auldridge M, Taylor MG, Klee HJ [2004] Plant J [in press]). Reduction of PhCCD1 transcript levels in transgenic plants led to a 58% to 76% decrease in beta-ionone synthesis in the corollas of selected petunia lines, indicating a significant role for this enzyme in volatile synthesis. Quantitative reverse transcription-PCR analysis revealed that PhCCD1 is highly expressed in corollas and leaves, where it constitutes approximately 0.04% and 0.02% of total RNA, respectively. PhCCD1 is light-inducible and exhibits a circadian rhythm in both leaves and flowers. beta-Ionone emission by flowers occurred principally during daylight hours, paralleling PhCCD1 expression in corollas. The results indicate that PhCCD1 activity and beta-ionone emission are likely regulated at the level of transcript.

Amino Acid Sequence↗
PubMed2003

Characterization of volatiles in bullock's heart (Annona reticulata L.) fruit cultivars from Cuba.

Volatile compounds were isolated from four cultivars of bullock's heart fruit (Cenizo, Rojo, Verde, and De Ojo) by simultaneous steam distillation-solvent extraction. Compounds were identified by HRGC and capillary GC-MS. One hundred and eighty compounds were identified in the aroma extracts, of which alpha-pinene, beta-pinene, myrcene, limonene, terpinen-4-ol, and germacrene D were found to be the major constituents. Fruit from cv. De Ojo containing the highest concentration of total volatile and the highest major terpenoid content had the highest custard-like and overall fruity aroma intensity. The presence of many terpenic compounds is thought to contribute to the unique flavor of the bullock's heart fruit.

Annona↗
PubMed1999

Aroma chemicals isolated and identified from leaves of Aloe arborescens Mill. Var. Natalensis Berger.

Extracts from leaves of aloe (Aloe arborescens Mill. var. natalensis Berger) were obtained using two methods: steam distillation under reduced pressure followed by dichloromethane extraction (DRP) and simultaneous purging and extraction (SPE). A total of 123 aroma chemicals were identified in the extracts obtained by both methods using gas chromatography and gas chromatography/mass spectrometry. There were 42 alcohols, 23 terpenoids, 21 aldehydes, 9 esters, 8 ketones, 6 acids, 5 phenols, and 9 miscellaneous compounds. The major aroma constituents of this extract by DRP were (Z)-3-hexenol (29.89%), (Z)-3-hexenal (18.86%), (E)-hexenal (7.31%), 4-methyl-3-pentenol (5.66%), and butanol (4.29%). The major aroma constituents of this extract by SPE were (E)-2-hexenal (45.46%), (Z)-3-hexenal (32.12%), hexanal (9.14%), (Z)-3-hexenol (1.60%), and 3-pentanone (1.41%). Terpenoids were also found as one of the major constituents. The fresh green note of aloe leaves is due to the presence of these C(6) alcohols and aldehydes as well as terpenoids.

Alcohols↗
PubMed2005

Flavor characteristics of lapsang souchong and smoked lapsang souchong, a special Chinese black tea with pine smoking process.

The major volatile constituents of lapsang souchong, smoked lapsang souchong, and smoked souchong, a group of special black teas in China, were analyzed with GC and GC-MS analyses. Forty-nine constituents were identified. Longifolene and alpha-terpineol were the most abundant compounds in the aroma. Due to its special production process, the compounds longifolene, longicyclene, guaiacol, 4-methylguaiacol, 4-ethylguaiacol, etc., were identified only in this kind of black tea. The aroma constituents of tea origin decreased during the smoking process, whereas the pine terpenoids and the thermal pyrolysis products of the pine wood increased markedly. The pine material for smoking was also analyzed for the volatile constituents showing apparent selectivity of the tea leaves to absorb. There were apparent differences among the tea samples in the contents of aroma constituents. The characteristics of the aroma of the teas are discussed with their processes and the features of sensory qualities.

Camellia sinensis↗
PubMed2004

The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles beta-ionone, pseudoionone, and geranylacetone.

Volatile terpenoid compounds, potentially derived from carotenoids, are important components of flavor and aroma in many fruits, vegetables and ornamentals. Despite their importance, little is known about the enzymes that generate these volatiles. The tomato genome contains two closely related genes potentially encoding carotenoid cleavage dioxygenases, LeCCD1A and LeCCD1B. A quantitative reverse transcriptase-polymerase chain reaction analysis revealed that one of these two genes, LeCCD1B, is highly expressed in ripening fruit (4 days post-breaker), where it constitutes 0.11% of total RNA. Unlike the related neoxanthin cleavage dioxygenases, import assays using pea chloroplasts showed that the LeCCD1 proteins are not plastid-localized. The biochemical functions of the LeCCD1 proteins were determined by bacterial expression and in vitro assays, where it was shown that they symmetrically cleave multiple carotenoid substrates at the 9,10 (9',10') positions to produce a C14 dialdehyde and two C13 cyclohexones that vary depending on the substrate. The potential roles of the LeCCD1 genes in vivo were assessed in transgenic tomato plants constitutively expressing the LeCCD1B gene in reverse orientation. This over-expression of the antisense transcript led to 87-93% reductions in mRNA levels of both LeCCD1A and LeCCD1B in the leaves and fruits of selected lines. Transgenic plants exhibited no obvious morphological alterations. High-performance liquid chromatography analysis showed no significant modification in the carotenoid content of fruit tissue. However, volatile analysis showed a > or =50% decrease in beta-ionone (a beta-carotene-derived C13 cyclohexone) and a > or =60% decrease in geranylacetone (a C13 acyclic product likely derived from a lycopene precursor) in selected lines, implicating the LeCCD1 genes in the formation of these important flavor volatiles in vivo.

Chloroplasts↗
PubMed2004

Composition and aroma compounds of Ragusano cheese: native pasture and total mixed rations.

Raw milk from 13 cows fed TMR supplemented with native pasture and from 13 cows fed only TMR on one farm was collected separately 4 times with an interval of 15 d between collections. Two blocks (14 kg each) of cheese were made from each milk. The objective was to determine the influence of consumption of native plants in Sicilian pastures on the aroma compounds present in Ragusano cheese. Milk from cows that consumed native pasture plants produced cheeses with more odor-active compounds. In 4-mo-old cheese made from milk of pasture-fed cows, 27 odor-active compounds were identified, whereas only 13 were detected in cheese made from milk of total mixed ration-fed cows. The pasture cheeses were much more rich in odor-active aldehyde, ester, and terpenoid compounds than cheeses from cows fed only total mixed ration. A total of 8 unique aroma-active compounds (i.e., not reported in other cheeses evaluated by gas chromatography olfactory) were detected in Ragusano cheese made from milk from cows consuming native Sicilian pasture plants. These compounds were 2 aldehydes ([E,E]-2,4-octadienal and dodecanal), 2 esters (geranyl acetate and [E]-methyl jasmonate), 1 sulfur compound (methionol), and 3 terpenoid compounds (1-carvone, L(-) carvone, and citronellol). Geranyl acetate and (E)-methyl jasmonate were particularly interesting because these compounds are released from fresh plants as they are being damaged and are part of a possible plant defense mechanism against damage from insects. Most of the odor-active compounds that were unique in Ragusano cheese from pasture-fed cows appeared to be compounds created by oxidation processes in the plants that may have occurred during foraging and ingestion by the cow. Some odor-active compounds were consistently present in pasture cheeses that were not detected in the total mixed ration cheeses or in the 14 species of pasture plants analyzed. Either these compounds were present in other plants not analyzed, created in the rumen or in cheese after the pasture-plant material had been consumed, or the compounds were lost in the method of sample extraction used for the plant analysis (i.e., steam distillation) versus the solid-phase microextraction method used for the cheeses. This research has demonstrated clearly that some unique odor-active compounds found in pasture plants can be transferred to the cheese.

Animal Feed↗
PubMed2004

Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species.

The blends of flavor compounds produced by fruits serve as biological perfumes used to attract living creatures, including humans. They include hundreds of metabolites and vary in their characteristic fruit flavor composition. The molecular mechanisms by which fruit flavor and aroma compounds are gained and lost during evolution and domestication are largely unknown. Here, we report on processes that may have been responsible for the evolution of diversity in strawberry (Fragaria spp) fruit flavor components. Whereas the terpenoid profile of cultivated strawberry species is dominated by the monoterpene linalool and the sesquiterpene nerolidol, fruit of wild strawberry species emit mainly olefinic monoterpenes and myrtenyl acetate, which are not found in the cultivated species. We used cDNA microarray analysis to identify the F. ananassa Nerolidol Synthase1 (FaNES1) gene in cultivated strawberry and showed that the recombinant FaNES1 enzyme produced in Escherichia coli cells is capable of generating both linalool and nerolidol when supplied with geranyl diphosphate (GPP) or farnesyl diphosphate (FPP), respectively. Characterization of additional genes that are very similar to FaNES1 from both the wild and cultivated strawberry species (FaNES2 and F. vesca NES1) showed that only FaNES1 is exclusively present and highly expressed in the fruit of cultivated (octaploid) varieties. It encodes a protein truncated at its N terminus. Green fluorescent protein localization experiments suggest that a change in subcellular localization led to the FaNES1 enzyme encountering both GPP and FPP, allowing it to produce linalool and nerolidol. Conversely, an insertional mutation affected the expression of a terpene synthase gene that differs from that in the cultivated species (termed F. ananassa Pinene Synthase). It encodes an enzyme capable of catalyzing the biosynthesis of the typical wild species monoterpenes, such as alpha-pinene and beta-myrcene, and caused the loss of these compounds in the cultivated strawberries. The loss of alpha-pinene also further influenced the fruit flavor profile because it was no longer available as a substrate for the production of the downstream compounds myrtenol and myrtenyl acetate. This phenomenon was demonstrated by cloning and characterizing a cytochrome P450 gene (Pinene Hydroxylase) that encodes the enzyme catalyzing the C10 hydroxylation of alpha-pinene to myrtenol. The findings shed light on the molecular evolutionary mechanisms resulting in different flavor profiles that are eventually selected for in domesticated species.

Acyclic Monoterpenes↗
PubMed2002

Effect of storage on some volatile aroma compounds in fresh-cut cantaloupe melon.

Changes in volatile aroma constituents of fresh-cut cantaloupe melon with storage were determined by headspace solid-phase microextraction gas chromatography-mass spectrometry. The compounds isolated from the fruit immediately after cutting were predominantly aliphatic and aromatic esters. Storage of fruit at 4 degrees C caused a considerable decrease in concentration of esters and synthesis of the terpenoid compounds beta-ionone and geranylacetone over a period of 24 h. This change in the volatile profile with storage is consistent with that of a stress-induced defense response in the cut fruit as an adaptation process to tissue exposure and cell disruption. The same effect occurred in fruit stored at 22 degrees C and in those treated with sodium azide and ascorbic acid prior to storage. Fruit treated with ascorbic acid and sodium azide had higher concentrations of beta-ionone and geranylacetone and retained these compounds better with storage time. The reduction of esters appears to be an important early reaction step in the loss of freshness during storage of fresh-cut cantaloupe.

Ascorbic Acid↗
PubMed2003

Changes in volatile compounds of carrots (Daucus carota L.) during refrigerated and frozen storage.

Carrots (Daucus carota L.) of cv. Bolero and cv. Carlo were processed into shreds and stored for up to 4 months at -24 degrees C (frozen storage), or the roots were stored for up to 4 months at 1 degrees C (refrigerated storage) followed by processing into shreds. Volatiles from the carrot shreds were collected by dynamic headspace technique and analyzed by GC-FID, GC-MS, GC-MS/MS, and GC-O to determine the volatile composition and aroma active components of carrots stored under different temperature conditions. A total of 52 compounds were quantified, of which mono- and sesquiterpenes accounted for approximately 99% of the total volatile mass. Major volatile compounds were (-)-alpha-pinene, beta-myrcene, (-)-limonene, (+)-limonene, (+)-sabinene, gamma-terpinene, p-cymene, terpinolene, beta-caryophyllene, alpha-humulene, and (E)- and (Z)-gamma-bisabolene. A considerable increase in the concentration of mono- and sesquiterpenes was observed during refrigerated storage, whereas the concentration of terpenoids was around the same level during frozen storage. GC-O revealed that the major volatiles together with (+)-alpha-pinene, (-)-beta-pinene, (+)-beta-pinene, 6-methyl-5-hepten-2-one, (-)-beta-bisabolene, beta-ionone, and myristicin had an odor sensation, which included notes of "carrot top", "terpene-like", "green", "earthy", "fruity", "citrus-like", "spicy", "woody", and "sweet".

Chromatography, Gas↗
PubMed2003

Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches.

Sweet basil (Ocimum basilicum L.) is an herb that is used to add a distinct aroma and flavor to food. Volatile compounds emitted from fully expanded fresh leaves grown in drip-irrigated plots that were covered with six colors of mulch were compared. The colors reflected a range of photosynthetic photon flux, far-red, red, and blue light from the soil surface to developing leaves. Our objective was to determine whether reflection from the different colors could influence concentrations of volatile compounds emitted from the fresh leaves. Volatile compounds were isolated by headspace sampling and quantified by gas chromatography. Twenty-six compounds were identified, of which the terpenoids linalool and 1,8-cineole comprised more than 50% of the total yield. Concentrations of volatile compounds from leaves that developed over green, blue, yellow, white, and red mulches followed the same patterns as they did for air-dried leaves of the same cultivar. However, the concentration of volatile compounds from fresh leaves was about 50-fold higher than those found in the previous study of air-dried leaves.

Acyclic Monoterpenes↗
PubMed2000

Aroma potential of two bairrada white grape varieties: Maria Gomes and Bical.

Maria Gomes and Bical are the main white grape varieties in Portuguese Bairrada Appellation, which represent 80% and 15%, respectively, of white vineyard. To estimate their aroma potentialities, free and potential volatile components from the musts were examined. The free volatile components were extracted using a liquid-liquid continuous method and were analyzed by gas chromatography-mass spectrometry. The potential volatile compounds were determined after elimination of the free components by heat and enzymatic treatments. Principal component analysis was used to establish relations between the compounds and the varieties and also the form (free or in potential). Maria Gomes has 11.5 mg/L volatile compounds, of which 33% are in free form; Bical has 4.4 mg/L volatile compounds, of which 46% are in free form. A total of 59 compounds was identified and quantified. In Maria Gomes, the sum of the terpenoids is within the perception limits for hotrienol (0.21 mg/L) and linalool (0.20 mg/L). In Bical, benzyl alcohol and phenylethylethanol represent 20% of the volatile compounds. Considering that the volatile composition pattern of Maria Gomes and Bical varieties are different, wine-making technologies should be developed specifically for each variety.

Alcohols↗
PubMed2004

Differences in the volatile components and their odor characteristics of green and ripe fruits and dried pericarp of Japanese pepper (Xanthoxylum piperitum DC.).

The essential oils of green and ripe fruits and dried pericarp of Japanese pepper (Xanthoxylum piperitum DC.), which are commonly used in Japanese dishes as spices, were extracted with methanol, followed by adsorption to Porapak Q resin. Their aroma profiles were characterized by a sensory evaluation, and their chemical constituents were investigated by using gas chromatography (GC), gas chromatography-mass spectrometry, and aroma extract dilution analysis. Geraniol, citronellal, linalool, and methyl cinnamate were perceived to be important to the basic flavor of the three samples of Japanese pepper by GC-sniffing at high flavor dilution (FD) factors. Monoterpene hydrocarbons constituting almost 76% of the essential oil are the major flavor compounds in the green fruit, and the stronger green and pine leaf notes in the green fruit were considered to be imparted mainly by the large amount of d-limonene, beta-phellandrene, and myrcene due to their high FD factors. On the other hand, the oxygenated terpenes including citronellal, geraniol, and geranial are predominant for the potent odorant in the ripe fruit. The marked citrus-like note in the ripe fruit was thought to be due to the amounts of geranial and citronellal, being 20% of the essential oil. In the dried pericarp, the ratio of oxygenated terpenoids was almost equal to that of monoterpene hydrocarbons. These seemed to induce the flavor character of the dried pericarp to be milder than that of the ripe fruit.

Chromatography, Gas↗
PubMed2006

Use of SPME-GC-MS in the study of time evolution of the constituents of saffron aroma: modifications of the composition during storage.

The effect of storage on the composition of saffron aroma is studied. Six samples of saffron from different areas of Italy are analyzed by solid-phase microextraction-gas chromatography-mass spectrometry. Samples 1, 2, and 3 are derived from cultivations of Crocus sativus in the zone of Salerno (Southern Italy) from 2000 to 2002. Samples 4, 5, and 6 are derived from cultivations in Sardinia, Italy (from 1998, 2000, and 2001, respectively). In all samples, 3,5,5-trimethyl-2-cyclohexen-1-one; 3,5,5-trimethyl-2-cyclohexen-1,4-dione; safranal; and 2,4,4-3,5,5-trimethyl-2-cyclohexen-1,4-dione; safranal; and 2,4,4-trimethyl-6-hydroxy-3-carboxaldehyde-2,5-cyclohexadien-1-one are found. 5,5-Dimethyl-2-methylene-1-carboxaldehyde-3-cyclohexene; 3,5,5-trimethyl-1,4-cyclohexandione; and beta-ionone are found with nonanal, dihydro-beta-ionone, and 2,6-di-t-butylphenol. Safranal is the main component in all of the samples. The most important changes are in the presence of alcohols and aldehydes and oxidation products of the major terpenoids components. Furthermore, the presence of safranal--the most important constituent of the flavor--changes during the time, increasing during 3 years, then decreasing after 5 years.

Crocus↗