Nat Struct Biol 8 : — Lange BM Biosynthesis and biotechnology of high-value p-menthane monoterpenes, including menthol, carvone, and limonene. Adv Biochem Eng Biotechnol : — Lange BM , Croteau R a Isoprenoid biosynthesis via a mevalonate-independent pathway in plants: cloning and heterologous expression of 1-deoxy-D-xylulosephosphate reductoisomerase from peppermint.
Lange BM , Croteau R b Isopentenyl diphosphate biosynthesis via a mevalonate-independent pathway: isopentenyl monophosphate kinase catalyzes the terminal enzymatic step. Med Aromat Plants 2 : 5. Lange BM , Rios-Estepa R Kinetic modeling of plant metabolism and its predictive power: peppermint essential oil biosynthesis as an example. Methods Mol Biol : — Plant Biotechnol J 11 : 2 — Genome Biol 10 : R Bioinformatics 28 : — Bioinformatics 26 : — Mahmoud SS , Croteau RB Metabolic engineering of essential oil yield and composition in mint by altering expression of deoxyxylulose phosphate reductoisomerase and menthofuran synthase.
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Sign In. Advanced Search. Search Menu. Article Navigation. Close mobile search navigation Article Navigation. Volume Article Contents Abstract. Johnson , Sean R. Institute of Biological Chemistry and M. Oxford Academic. Iris Lange. Narayanan Srividya. Markus Lange. Cite Cite Sean R. Select Format Select format. Permissions Icon Permissions. Open in new tab Download slide. Table I. Reaction Description.
Open in new tab. Multiple levels of regulation determine monoterpenoid essential oil compositional variation in the mint family.
Google Scholar Crossref. Search ADS. Bottom-up metabolic reconstruction of Arabidopsis and its application to determining the metabolic costs of enzyme production. The energy charge of the adenylate pool as a regulatory parameter: interaction with feedback modifiers. Multi-omics of tomato glandular trichomes reveals distinct features of central carbon metabolism supporting high productivity of specialized metabolites.
The development of type VI glandular trichomes in the cultivated tomato Solanum lycopersicum and a related wild species S. Unexpected roles for ancient proteins: flavone 8-hydroxylase in sweet basil trichomes is a Rieske-type, PAO-family oxygenase. Demonstration that menthofuran synthase of mint Mentha is a cytochrome P monooxygenase: cloning, functional expression, and characterization of the responsible gene. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding.
Carbohydrate metabolism in source leaves of sweet basil Ocimum basilicum L. Geranyl diphosphate synthase: cloning, expression, and characterization of this prenyltransferase as a heterodimer. Direct regeneration in vitro and transient GUS expression in Mentha x piperita.
Google Scholar PubMed. A method for accounting for maintenance costs in flux balance analysis improves the prediction of plant cell metabolic phenotypes under stress conditions. Monoterpene metabolism: cloning, expression, and characterization of menthone reductases from peppermint. AraGEM, a genome-scale reconstruction of the primary metabolic network in Arabidopsis.
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Intragenic recombination in maize: pollen analysis methods and the effect of parental adh1 isoalleles. An investigation of the storage and biosynthesis of phenylpropenes in sweet basil.
Biochemical and histochemical localization of monoterpene biosynthesis in the glandular trichomes of spearmint Mentha spicata. Isolation of secretory cells from plant glandular trichomes and their use in biosynthetic studies of monoterpenes and other gland products. Full-length transcriptome assembly from RNA-Seq data without a reference genome. Detection and kinetic properties of alcohol dehydrogenase in dormant corm of Crocus sativus L. Multiple iso-proteins of FNR in Arabidopsis: evidence for different contributions to chloroplast function and nitrogen assimilation.
Metabolic network reconstruction and flux variability analysis of storage synthesis in developing oilseed rape Brassica napus L. To us, however, they represent so much more. Though we do utilize them for their beneficial medicinal properties, we also regale them for their flavors and aromas.
Substances created within glandular trichomes enhance our daily lives and prove that, no matter what, we are still strongly attached to the plants we grow and the nature that surrounds us. About Us. Dry Blends Liquid Blends. Where To Buy. Distributors Online Retail Stores. Follow Us On. Contact Us. Essential oil is not actually an oil because it contains no fatty substance. It is obtained from the essence rich in natural flavors and active ingredients that it secretes the cells of certain parts of the plant.
Precious liquids are obtained by distilling or pressing the secretory organs. For example, citrus peel is cold pressed, and the other parts of the plant stem, leaves, flowers, root, wood are distilled 3 , 4. These processes result in an aromatic concentrate and a genuine source of active substances.
Essential oil is also known as volatile oil or ethereal oil 5. Extraction of essential oils is expensive because of the large amount of raw material required to produce a few milliliters of oil. This explains the high prices required for genuine essential oils. For example, to obtain a single drop of essential rose oil, approx. However, there are also less expensive oils due to the abundance of inexpensive raw materials and high productivity. Such oils are citrus—lemon, orange, bergamot, lime, lemongrass oil, tea tree oil.
Essential oils are relatively widespread in the plant kingdom, some families being very rich in such substances, both in number and quantity. Typically, essential oils are found in superior plants about 50 families belonging to orders of angiosperms Asterales, Laurales, Magnoliales, Zimgiberales, etc. Although terpenic compounds are characteristic of the plant kingdom, some biosynthesized monoterpenes have been reported from soil bacteria, insects probably pheromones , and some sesquiterpene and diterpenes of animal origin 10 , 11 , The synthesis and accumulation of essential oils occur either outside the plant, in the glandular brushes Asteraceae, Geraniaceae, Laminaceae, etc.
Essential oils can accumulate in all plant organs, but in varying amounts. Thus we can meet them in: roots, leaves, flowers, fruits, wood of the stems or in the bark. The name of aromatic plants is attributed to those species which contain a higher amount of volatile oil at least 0.
In addition, there are other species that, although characteristically smell, still contain therapeutic substances that are comprised of essential oils. The biosynthesis of odorous substances takes place in the leaves, where most of them are found and remains until flowering. Flowering, essential oils migrate into flowers, and part is consumed in the fertilization process. After fertilization, it accumulates in fruits and seeds or there is a migration to leaves, bark and root 16 , During the maturation of plants, the composition of essential oils changes: in young plants they contain mainly terpenic hydrocarbons and simpler molecules, while the reproductive organs contain etheric oils richer in oxygenated compounds.
Although their role in the plant organism is partly known, ethereal oils have multiple uses. There are more than 3, essential oils that are physically and chemically characterized, about of which are manufactured on an industrial scale 18 , 19 , Essential oils are complex mixtures — chemical constituents in which mono— and sesquitrpene constituents predominate, but also contain aromatic compounds, often phenylpropane derivatives, and rarely meet diterpenes.
The terpenic compounds may be hydrocarbons or oxygenated derivatives oxides, alcohols, aldehydes, ketones, acids or reaction products thereof esters, ethers. Terpenic compounds are substances of vegetable origin that enter into the natural composition of molecular mixtures that lead to the formation of volatile essential, etheric oils.
Obtaining aromatic waters and essential oils requires raw materials, plant products, quality. First of all, harvesting the plant material should be done with great care, so that it is not contaminated with other plant species. Essential oils are widespread in the most varied organs of the plant, but are more commonly found in flowers and leaves 21 , The chemical composition of essential oils is very varied and the main components can be part of the aliphatic, aromatic and terpenic series.
Generally, essential oils contain ternary, rarely quaternary substances. Volatile products are made up of terpenes, aromatics, aldehydes, ketones, phenols, volatile acids, esters, etc.
The plant material that is subject to hydrodynamics is not always processed after harvesting Generally, fresh plants lead to more pleasant odor solutions and greater therapeutic action; except cinnamon, lime flowers and lavender flowers that are used dry.
In the case of dry plants, the lower volatile urine is sometimes obtained as a result of morphological and chemical changes due to the action of air, heating, because of the accumulation of grams, possibly by alteration 24 , Also, the technological process of obtaining volatile oil intervenes decisively in its composition and its quality.
In the case of hydrodistillation, physical and chemical processes are produced which significantly alter the content of the plant material and, consequently, the volatile oil released. Vegetable products are brought to a convenient degree by crushing, cutting, grinding, which is chosen according to its nature and chemical composition 26 , 27 , Thus, the flowers and leaves fall down to pass through the sieve I, and bark and roots, dried fruits and seeds, through sieve II or III.
Fresh fruits are crushed to obtain a pulp that is subject to water vapor entrainment. The plant—solvent ratio ranges from 1: 1 to 1: 5. This proportion is dependent on the amount of volatile oil contained in the plant and its solubility The excess undiluted volatile oil is separated from the saturated aqueous solution. Trimmed reads were mapped to the de novo transcriptome assembly of C. Similarly, the range of Pearson correlation coefficient between two samples in each experimental group is 0.
Figure 2. Transcriptional cascade of DEGs in terpenoid backbone biosynthesis in linalool-type C. The x- axis indicates the number of unigenes annotated in each corresponding pathway. The five categories of KEGG pathways are divided and color-coded. B DEGs in terpenoid backbone biosynthesis.
The transcriptional cascade of terpenoid backbone biosynthesis is shown in the form of protein-coding enzymes or nodes annotated by KEGG pathway analysis. The left three and right three columns represent low oil content type N and linalool type LI , respectively.
The black bars represent relative gene expression determined by qRT-PCR left y -axis and the dotted gray bars represent gene expression levels detected by RNA-Seq right y- axis. Standard errors of the three technical replicates of each sample of the qRT-PCR analysis and three biological replicates in the two experimental groups of the RNA-Seq analysis are indicated by error bars.
Annotated protein-coding enzymes were mapped into the terpenoid backbone biosynthesis pathway, and gene expression data of each enzyme in the two experimental groups were indicated with logRPKM values Figure 2B and Supplementary Table S6.
Among the DEGs, 14 unigenes were annotated as terpenoid synthase—encoding genes, including four in monoterpenoid biosynthesis, four in sesquiterpenoid and triterpenoid biosynthesis, and six in diterpenoid biosynthesis Figure 2B and Supplementary Table S6.
One LIS-like and one GerS-like unigene were up-regulated in the monoterpenoid biosynthesis pathway, indicating that increased availability of terpenoid precursors, along with increased levels of monoterpene synthases, might be the reason for the higher oil yield and higher accumulation of linalool and other monoterpenes in the trees of linalool type.
In general, the upregulation of terpenoid synthase unigenes in the trees of linalool-type C. Because of earlier unregulated harvesting, many natural sources of camphor trees have been exhausted. In response to this, camphor tree plantations have been established in many countries including China and Japan. These camphor trees are maintained as bushes and are harvested for twigs and leaves before essential oil extraction.
Camphor trees can be divided into different chemotypes based on their main terpenoid components. In this study, we identified camphor trees of linalool type and low oil contents without a dominant terpene component.
A total of 26 main components were identified by GC-MS. We further demonstrated that the chemical components in the essential oils of C. Terpenoid biosynthesis and its regulation are extensively documented in many plant species.
Although many members of the Lauraceae family are rich in terpenoids and are economically important tree species, limited studies are available analyzing genes involved in its terpenoid biosynthesis pathway Yang et al. This study was focused on identifying genes involved in terpenoid biosynthesis and key enzymes involved in the biosynthesis of the backbone IPP and DMAPP molecules in C.
A transcriptome of C. This is consistent with our observation that September—November is the time of the year when C. Furthermore, and 18 expressed unigenes were identified to be highly homologous with 49 and 11 known enzymes in the terpenoid backbone biosynthesis and monoterpenoid biosynthesis pathways, respectively. By comparing the transcriptome profiles of leaves of linalool and leaves with low oil contents, 3, unigenes were identified as DEGs.
However, the contribution of each pathway to the generation of the common precursors for varied terpenoid biosynthesis is still unknown, because crosstalk between the two pathways has been documented in many species including chamomile, Arabidopsis , tobacco, and snapdragon Adam and Zapp, ; Bick and Lange, ; Hemmerlin et al.
Although the percentage of diterpenes in leaf extracts of linalool-type camphor trees is not high, their oil yield is much higher than trees of low oil yield. Therefore, higher GGPPS expression level may simply be correlated with a general increase in oil content. Interestingly, it has been documented that GPP, the precursor for monoterpene, is constitutively and ubiquitously expressed in Arabidopsis Van Schie et al. However, caution should be used when assigning protein functions to terpenoid synthase genes predicted based on sequence similarities as it has been reported that point mutations alone were sufficient to significantly change the kinetic activity of a linalool synthase gene in Cinnamomum osmophloeum Lin et al.
Additionally, alternative splicing has been shown to alter linalool biosynthesis, as reported in Camellia sinensis Liu et al. Higher levels of monoterpene production could potentially lower production of other terpenes and isoprenoid derivatives due to the competition for common precursors.
Other genes of interest emerged from this study, which include several members of the WRKY family. WRKY transcription factors have been reported to regulate the expression of genes involved in terpene biosynthesis in many species, including Arabidopsis , cotton, Artemisia annua , Catharanthus roseus , and others Xu et al.
Moreover, it was suggested that the linalool-type C. Based on these previous studies, we suspect that members of the WRKY family might be involved in the regulation of terpene synthase genes of C.
All in all, this study identified a cohort of genes in the terpenoid backbone biosynthesis and monoterpenoid biosynthesis pathways that were commonly up-regulated in leaves with high linalool contents compared to leaves with low oil contents. The knowledge obtained from this study could facilitate manipulation of camphor tree essential oil production through metabolic engineering of essential oil biosynthesis. Additional studies should focus on the isolation of monoterpene synthases genes from different chemotypes of C.
Additionally, functional analyses are needed to demonstrate the impact of these genes on terpenoid production. HZ and JH analyzed the data. JH wrote the manuscript.
All authors read and approved the final manuscript. The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.
We thank HuiJuan Cheng and Yiqun Zhang for their assistance in sample harvesting and essential oil extraction. We would also like to thank Yanbo Wang and reviewers for their help in improving the manuscript.
Supplementary Table 3 GO enrichment analysis of C. Supplementary Table 6 Putative unigenes associated with terpenoid biosynthesis. Supplementary Table 7 Sequences of putative unigenes associated with terpenoid biosynthesis. Adam, K. Biosynthesis of the isoprene units of chamomile sesquiterpenes. Phytochemistry 48, — Aharoni, A. Gain and loss of fruit flavor compounds produced by wild and cultivated strawberry species.
Plant Cell 16, —
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