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Molecules (Basel, Switzerland) Feb 2023Terpenes and essential oils are materials of great commercial use due to their broad spectra of antibacterial, antifungal, membrane permeation enhancement and... (Review)
Review
Terpenes and essential oils are materials of great commercial use due to their broad spectra of antibacterial, antifungal, membrane permeation enhancement and antioxidant biological properties, as well as for their use as flavors and fragrances. Yeast particles (YPs) are 3-5 µm hollow and porous microspheres, a byproduct of some food-grade yeast ( extract manufacturing processes, that have been used for the encapsulation of terpenes and essential oils with high payload loading capacity (up to 500% weight) and efficiency, providing stability and sustained-release properties. This review focuses on encapsulation approaches for the preparation of YP-terpene and essential oil materials that have a wide range of potential agricultural, food and pharmaceutical applications.
Topics: Oils, Volatile; Terpenes; Saccharomyces cerevisiae
PubMed: 36903519
DOI: 10.3390/molecules28052273 -
International Journal of Molecular... Apr 2023The fragrance industry is increasingly turning to biotechnology to produce sustainable and high-quality fragrance ingredients. Microbial-based approaches have been found... (Review)
Review
The fragrance industry is increasingly turning to biotechnology to produce sustainable and high-quality fragrance ingredients. Microbial-based approaches have been found to be particularly promising, as they offer a more practical, economical and sustainable alternative to plant-based biotechnological methods for producing terpene derivatives of perfumery interest. Among the evaluated works, the heterologous expression of both terpene synthase and mevalonate pathway into has shown the highest yields. Biotechnology solutions have the potential to help address the growing demand for sustainable and high-quality fragrance ingredients in an economically viable and responsible manner. These approaches can help compensate for supply issues of rare or impermanent raw materials, while also meeting the increasing demand for sustainable ingredients and processes. Although scaling up biotransformation processes can present challenges, they also offer advantages in terms of safety and energy savings. Exploring microbial cell factories for the production of natural fragrance compounds is a promising solution to both supply difficulties and the demand for sustainable ingredients and processes in the fragrance industry.
Topics: Metabolic Engineering; Perfume; Terpenes; Biotechnology; Plants; Escherichia coli
PubMed: 37175581
DOI: 10.3390/ijms24097874 -
Applied Microbiology and Biotechnology Aug 2022There is a growing appreciation for the role that yeast play in biotransformation of flavour compounds during beverage fermentations. This is particularly the case for... (Review)
Review
There is a growing appreciation for the role that yeast play in biotransformation of flavour compounds during beverage fermentations. This is particularly the case for brewing due to the continued popularity of aromatic beers produced via the dry-hopping process. Here, we review the current literature pertaining to biotransformation reactions mediated by fermentative yeasts. These reactions are diverse and include the liberation of thiols from cysteine or glutathione-bound adducts, as well as the release of glycosidically bound terpene alcohols. These changes serve generally to increase the fruit and floral aromas in beverages. This is particularly the case for the thiol compounds released via yeast β-lyase activity due to their low flavour thresholds. The role of yeast β-glucosidases in increasing terpene alcohols is less clear, at least with respect to fermentation of brewer's wort. Yeast acetyl transferase and acetate esterase also have an impact on the quality and perceptibility of flavour compounds. Isomerization and reduction reactions, e.g. the conversion of geraniol (rose) to β-citronellol (citrus), also have potential to alter significantly flavour profiles. A greater understanding of biotransformation reactions is expected to not only facilitate greater control of beverage flavour profiles, but also to allow for more efficient exploitation of raw materials and thereby greater process sustainability. KEY POINTS: • Yeast can alter and boost grape- and hop-derived flavour compounds in wine and beer • β-lyase activity can release fruit-flavoured thiols with low flavour thresholds • Floral and citrus-flavoured terpene alcohols can be released or interconverted.
Topics: Alcohols; Beer; Biotransformation; Fermentation; Flavoring Agents; Fruit; Lyases; Saccharomyces cerevisiae; Sulfhydryl Compounds; Terpenes; Yeasts
PubMed: 35851416
DOI: 10.1007/s00253-022-12068-w -
Chemical Reviews Sep 2017The year 2017 marks the twentieth anniversary of terpenoid cyclase structural biology: a trio of terpenoid cyclase structures reported together in 1997 were the first to... (Review)
Review
The year 2017 marks the twentieth anniversary of terpenoid cyclase structural biology: a trio of terpenoid cyclase structures reported together in 1997 were the first to set the foundation for understanding the enzymes largely responsible for the exquisite chemodiversity of more than 80000 terpenoid natural products. Terpenoid cyclases catalyze the most complex chemical reactions in biology, in that more than half of the substrate carbon atoms undergo changes in bonding and hybridization during a single enzyme-catalyzed cyclization reaction. The past two decades have witnessed structural, functional, and computational studies illuminating the modes of substrate activation that initiate the cyclization cascade, the management and manipulation of high-energy carbocation intermediates that propagate the cyclization cascade, and the chemical strategies that terminate the cyclization cascade. The role of the terpenoid cyclase as a template for catalysis is paramount to its function, and protein engineering can be used to reprogram the cyclization cascade to generate alternative and commercially important products. Here, I review key advances in terpenoid cyclase structural and chemical biology, focusing mainly on terpenoid cyclases and related prenyltransferases for which X-ray crystal structures have informed and advanced our understanding of enzyme structure and function.
Topics: Alkyl and Aryl Transferases; Carbon-Carbon Lyases; Crystallography, X-Ray; Dimethylallyltranstransferase; Intramolecular Lyases; Protein Structure, Tertiary; Terpenes
PubMed: 28841019
DOI: 10.1021/acs.chemrev.7b00287 -
Pharmacological Reviews Oct 2021Pain prevalence among adults in the United States has increased 25% over the past two decades, resulting in high health-care costs and impacts to patient quality of... (Review)
Review
Pain prevalence among adults in the United States has increased 25% over the past two decades, resulting in high health-care costs and impacts to patient quality of life. In the last 30 years, our understanding of pain circuits and (intra)cellular mechanisms has grown exponentially, but this understanding has not yet resulted in improved therapies. Options for pain management are limited. Many analgesics have poor efficacy and are accompanied by severe side effects such as addiction, resulting in a devastating opioid abuse and overdose epidemic. These problems have encouraged scientists to identify novel molecular targets and develop alternative pain therapeutics. Increasing preclinical and clinical evidence suggests that cannabis has several beneficial pharmacological activities, including pain relief. contains more than 500 chemical compounds, with two principle phytocannabinoids, Δ-tetrahydrocannabinol (Δ-THC) and cannabidiol (CBD). Beyond phytocannabinoids, more than 150 terpenes have been identified in different cannabis chemovars. Although the predominant cannabinoids, Δ-THC and CBD, are thought to be the primary medicinal compounds, terpenes including the monoterpenes -myrcene, -pinene, limonene, and linalool, as well as the sesquiterpenes -caryophyllene and -humulene may contribute to many pharmacological properties of cannabis, including anti-inflammatory and antinociceptive effects. The aim of this review is to summarize our current knowledge about terpene compounds in cannabis and to analyze the available scientific evidence for a role of cannabis-derived terpenes in modern pain management. SIGNIFICANCE STATEMENT: Decades of research have improved our knowledge of cannabis polypharmacy and contributing phytochemicals, including terpenes. Reform of the legal status for cannabis possession and increased availability (medicinal and recreational) have resulted in cannabis use to combat the increasing prevalence of pain and may help to address the opioid crisis. Better understanding of the pharmacological effects of cannabis and its active components, including terpenes, may assist in identifying new therapeutic approaches and optimizing the use of cannabis and/or terpenes as analgesic agents.
Topics: Adult; Analgesics; Cannabinoids; Cannabis; Humans; Quality of Life; Terpenes
PubMed: 34663685
DOI: 10.1124/pharmrev.120.000046 -
Molecules (Basel, Switzerland) Oct 2022Differences between therapeutic effects of medical cannabis inflorescences and those of their extracts are generally attributed to the differences in administration form...
Optimal Treatment with Cannabis Extracts Formulations Is Gained via Knowledge of Their Terpene Content and via Enrichment with Specifically Selected Monoterpenes and Monoterpenoids.
Differences between therapeutic effects of medical cannabis inflorescences and those of their extracts are generally attributed to the differences in administration form and in the resultant pharmacokinetics. We hypothesized that difference may further extend to the composition of the actually consumed drug. Cannabinoid and terpene contents were compared between commercial cannabis inflorescences ( = 19) and decarboxylated extracts ( = 12), and between inflorescences and decarboxylated extracts produced from them ( = 10). While cannabinoid content was preserved in the extracts, a significant loss of terpenes was evident, mainly in the more volatile monoterpenes and monoterpenoids (representing a loss of about 90%). This loss changes the total terpene content, the proportion of monoterpenes out of the total terpenes, and the monoterpene/cannabinoid ratio. Terpene deficiency might impair extracts' pharmacological efficacy and might contribute to the patients' preference to inflorescences-smoking. This argues against the validity of terms such as "whole plant" and "full spectrum" extracts and creates a misleading assumption that extracts represent the pharmacological profile of the sourced inflorescences. Furthermore, it reduces the diversity in extracts, such as loss of differences between sativa-type and indica-type. Enriching cannabis extracts with selected terpenes may provide a suitable solution, generating a safe, precise, and reproducible drug with tailored cannabinoid and terpene contents. Careful selection of terpenes to be added enables tailor-made extracts, adjusted for various medicinal aims and for different populations.
Topics: Humans; Cannabis; Terpenes; Monoterpenes; Medical Marijuana; Cannabinoids; Hallucinogens; Cannabinoid Receptor Agonists; Plant Extracts
PubMed: 36296511
DOI: 10.3390/molecules27206920 -
The Journal of Antibiotics Jul 2017Terpenoids are a large and highly diverse group of natural products. All terpenoids are biosynthesized from isoprenyl diphosphate formed by the consecutive condensation... (Review)
Review
Terpenoids are a large and highly diverse group of natural products. All terpenoids are biosynthesized from isoprenyl diphosphate formed by the consecutive condensation of the five-carbon monomer isopentenyl diphosphate (IPP) to its isomer dimethylallyl diphosphate (DMAPP). Two distinct biosynthetic pathways produce the essential primary metabolites IPP and DMAPP: the 2-C-methylerythritol 4-phosphate pathway and the mevalonate pathway. The isoprenyl substrates can be cyclized by terpene cyclase into single-ring or multi-ring products, which can be further diversified by subsequent modification reactions, such as hydroxylation and glycosylation. This review article describes the biosynthetic pathways of terpenoids produced by Streptomyces and their related novel enzymes.
Topics: Biological Products; Biosynthetic Pathways; Erythritol; Mevalonic Acid; Streptomyces; Sugar Phosphates; Terpenes
PubMed: 28196976
DOI: 10.1038/ja.2017.12 -
The New Phytologist Dec 2019Conifers have evolved complex oleoresin terpene defenses against herbivores and pathogens. In co-evolved bark beetles, conifer terpenes also serve chemo-ecological... (Review)
Review
Conifers have evolved complex oleoresin terpene defenses against herbivores and pathogens. In co-evolved bark beetles, conifer terpenes also serve chemo-ecological functions as pheromone precursors, chemical barcodes for host identification, or nutrients for insect-associated microbiomes. We highlight the genomic, molecular and biochemical underpinnings of the large chemical space of conifer oleoresin terpenes and volatiles. Conifer terpenes are predominantly the products of the conifer terpene synthase (TPS) gene family. Terpene diversity is increased by cytochromes P450 of the CYP720B class. Many conifer TPS are multiproduct enzymes. Multisubstrate CYP720B enzymes catalyse multistep oxidations. We summarise known terpenoid gene functions in various different conifer species with reference to the annotated terpenoid gene space in a spruce genome. Overall, biosynthesis of terpene diversity in conifers is achieved through a system of biochemical radiation and metabolic grids. Expression of TPS and CYP720B genes can be specific to individual cell types of constitutive or traumatic resin duct systems. Induced terpenoid transcriptomes in resin duct cells lead to dynamic changes of terpene composition and quantity to fend off herbivores and pathogens. While terpenoid defenses have contributed much to the evolutionary success of conifers, under new conditions of climate change, these defences may become inconsequential against range-expanding forest pests.
Topics: Alkyl and Aryl Transferases; Animals; Climate Change; Coleoptera; Cytochrome P-450 Enzyme System; Gene Expression Regulation, Plant; Herbivory; Phylogeny; Plant Extracts; Terpenes; Tracheophyta
PubMed: 31179548
DOI: 10.1111/nph.15984 -
Nature Chemical Biology Jun 2022Octocorals are major contributors of terpenoid chemical diversity in the ocean. Natural products from other sessile marine animals are primarily biosynthesized by...
Octocorals are major contributors of terpenoid chemical diversity in the ocean. Natural products from other sessile marine animals are primarily biosynthesized by symbiotic microbes rather than by the host. Here, we challenge this long-standing paradigm by describing a monophyletic lineage of animal-encoded terpene cyclases (TCs) ubiquitous in octocorals. We characterized 15 TC enzymes from nine genera, several of which produce precursors of iconic coral-specific terpenoids, such as pseudopterosin, lophotoxin and eleutherobin. X-ray crystallography revealed that coral TCs share conserved active site residues and structural features with bacterial TCs. The identification of coral TCs enabled the targeted identification of the enzyme that constructs the coral-exclusive capnellane scaffold. Several TC genes are colocalized with genes that encode enzymes known to modify terpenes. This work presents an example of biosynthetic capacity in the kingdom Animalia that rivals the chemical complexity generated by plants, unlocking the biotechnological potential of octocorals for biomedical applications.
Topics: Animals; Anthozoa; Bacteria; Terpenes
PubMed: 35606558
DOI: 10.1038/s41589-022-01026-2 -
Nature Communications May 2022Pericyclases, enzymes that catalyze pericyclic reactions, form an expanding family of enzymes that have biocatalytic utility. Despite the increasing number of...
Pericyclases, enzymes that catalyze pericyclic reactions, form an expanding family of enzymes that have biocatalytic utility. Despite the increasing number of pericyclases discovered, the Diels-Alder cyclization between a cyclopentadiene and an olefinic dienophile to form norbornene, which is among the best-studied cycloadditions in synthetic chemistry, has surprisingly no enzymatic counterpart to date. Here we report the discovery of a pathway featuring a norbornene synthase SdnG for the biosynthesis of sordaricin-the terpene precursor of antifungal natural product sordarin. Full reconstitution of sordaricin biosynthesis reveals a concise oxidative strategy used by Nature to transform an entirely hydrocarbon precursor into the highly functionalized substrate of SdnG for intramolecular Diels-Alder cycloaddition. SdnG generates the norbornene core of sordaricin and accelerates this reaction to suppress host-mediated redox modifications of the activated dienophile. Findings from this work expand the scopes of pericyclase-catalyzed reactions and P450-mediated terpene maturation.
Topics: Biocatalysis; Biosynthetic Pathways; Cycloaddition Reaction; Norbornanes; Terpenes
PubMed: 35546152
DOI: 10.1038/s41467-022-30288-6