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Terpenes: Flavors, Fragrances, Pharmaca, Pheromones

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... In this context, the large family of terpenes represents a natural, potentially important source of unsaturated hydrocarbons, useful in producing polymers [7][8][9][10][11]. Terpenes are ubiquitous molecules, characterized by the presence of one or more double bonds, found in many plants (mainly conifers), fungi and even some insect, which have both linear and cyclic structures and share 2methyl-1,4-butadiene (isoprene) (C5) as an elementary unit [12]. Among these compounds, β-myrcene (M)-due to the structural similarity to isoprene (I) and butadiene (B) and large availability-has recently aroused a growing attention as building block for the synthesis presence of a slight excess of NaH with respect to TIBA, in addition to the 1:1 complex, the formation of the 1:2 complex with an active site was postulated. ...
... Head-to-head and tail-to-tail enchainments bridge of 1,4-cis M additions (see Figure S3 in detail, SI), previously observed in the PM, were also visible in all 13 C { 1 H} spectra of PMS copolymers. Glass transition temperatures of PMS (runs [10][11][12][13][14] lie between that of the homopolymers (−76.5 and 105.5 °C for polymyrcene and atactic polystyrene, respectively) and are listed in Table 2. All the copolymers, with the exception of run 21, showed a single Tg value which decreased with increasing amount of M incorporated in the copolymers. ...
... Head-to-head and tail-to-tail enchainments bridge of 1,4-cis M additions (see Figure S3 in detail, SI), previously observed in the PM, were also visible in all 13 C { 1 H} spectra of PMS copolymers. Glass transition temperatures of PMS (runs [10][11][12][13][14] lie between that of the homopolymers (−76.5 and 105.5 • C for polymyrcene and atactic polystyrene, respectively) and are listed in Table 2. All the copolymers, with the exception of run 21, showed a single T g value which decreased with increasing amount of M incorporated in the copolymers. ...
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Soluble heterocomplexes consisting of sodium hydride in combination with trialkylaluminum derivatives have been used as anionic initiating systems at 100 °C in toluene for convenient homo-, co- and ter-polymerization of myrcene with styrene and isoprene. In this way it has been possible to obtain elastomeric materials in a wide range of compositions with interesting thermal profiles and different polymeric architectures by simply modulating the alimentation feed and the (monomers)/(initiator systems) ratio. Especially, a complete study of the myrcene-styrene copolymers (PMS) was carried out, highlighting their tapered microstructures with high molecular weights (up to 159.8 KDa) and a single glass transition temperature. For PMS copolymer reactivity ratios, rmyr = 0.12 ± 0.003 and rsty = 3.18 ± 0.65 and rmyr = 0.10 ± 0.004 and rsty = 3.32 ± 0.68 were determined according to the Kelen–Tudos (KT) and extended Kelen–Tudos (exKT) methods, respectively. Finally, this study showed an easy accessible approach for the production of various elastomers by anionic copolymerization of renewable terpenes, such as myrcene, with commodities.
... In this situation, we have to utilize this period to evaluate and create major pathways to use alternative resources for the production of biobased synthetic elastomers. Terpenes or terpenoids are natural materials built from isoprene and produced by plants and insects [1,2]. Terpenes are readily available in large amounts and with a variety of structures, and therefore can be easily used for synthesis even without modifications. ...
... Ocimene, farnesene [63], and alloocimene [64] have been subjected to redox emulsion polymerization, using tert-butyl hydroperoxide and ammonium persulfate initiators, under ambient conditions. Farnesene has also been statistically copolymerized with glycidyl methacrylate, while its copolymer has been block-copolymerized with styrene, using a N-succinimidyl modified commercial BlocBuilder initiator, via NMP [1]. Polymeric alloocimene via free radical method was found to be amorphous, while the rubbery polyocimene and polyfarnesene formed in low yields because of the hindered double bonds of their monomers. ...
... In earlier days, terpenes were used mainly as solvents in the chemical industry, but these compounds have long been used in human culture, as a component of essential oils. Terpene oils are employed widely as natural flavor additives for food, and as fragrances in perfumery ( Figure 14) [1,88]. The application portfolios of terpenes also extend into conventional and alternative medicines, such as aromatherapy, and they also have anti-fungal, anti-depressant and anti-anxiety properties, as well as antiseptic, anti-bacterial and anti-inflammatory medical benefits [89]. ...
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The limited source of fossil-fuel and the predominance of petroleum-based chemistry in the manufacturing of commodity polymers has generated tremendous interest in replacing the fossil source-based polymers with renewable counterparts. The field of sustainable elastomers has grown in the past three decades, from a few examples to a plethora of reports in modern polymer science and technology. Applications of elastomers are huge and vital for everyday living. The present review aims to portray a birds-eye view of various sustainable elastomers obtained from the wide family of acyclic terpenes (renewable feedstocks from different plant oils) via various polymerization techniques and their properties, as well as plausible developments in the future applications of sustainable polymers. Not only the homopolymers, but also their copolymers with both green and commercial fossil based comonomers, are reviewed.
... They can be easily extracted from different essentials oils that are widely available from biomass. For instance, citronellal is an acyclic monoterpenic aldehyde extensively used as an insect repellant that is found in oil of citronella and obtained from Cymbopogon nardus (Poaceae) fresh grass [18,19]. The citronellal can be involved in some different chemical transformations to obtain other monoterpenic compounds, for example, can be highlighted the cyclization reaction of citronellal to synthesize (-)-isopulegol that is a very important compound in industry. ...
... (-)-Isopulegol is a monoterpenic alcohol that has a very pleasant smell of lilac blossoms and is an relevant raw material in perfumery. Moreover, (-)-isopulegol is synthesis intermediate of (-)-menthol, which is a valuable ingredient of commercial interested used in various pharmaceuticals, cosmetics, toothpaste, among others products [19][20][21][22]. ...
... The cyclization reaction of (+)-citronellal to synthesize (-)-isopulegol is a very relevant chemical transformation of terpenic compounds for the chemical industry [19][20][21][22], especially the fine chemical industry, being, therefore, an attractive route to valorization of ingredient from biomass. (-)-Isopulegol is a versatile product in different segments of the fine chemical and it has high commercial value [19][20][21][22][23], even it produced in small quantities. ...
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In this work, sulfonated expanded polystyrene waste (WEPS), obtaining from recycling of the expanded polystyrene (EPS) waste by low-cost sulfonation reaction, were successfully applied as environmentally benign acid solid in the liquid-phase cyclization of (+)-citronellal (1), under mild reaction conditions. (-)-Isopulegol (2) and (+)-neoisopulegol (3) were obtained with a total yield equal to 80%. Products 2 and 3 have direct industrial application in the composition of fragrances and flavorings. (-)-Isopulegol is also used as a synthesis intermediate of (-)-menthol. It was not observed the leaching of acid sites from WEPS to reaction solution, thereby, this process presented heterogeneuos nature. The WEPS was stable in the reaction medium and presented little significant loss of its performance in consecutive reactions of its reuse. In addition, WEPS showed better performance than commercial resin Amberlyst-15, in the same reaction conditions. The use of WPES as acid solid in reactions of industrial interest is an attractive, low-cost and environmentally friendly alternative for application of this material, obtained by recycling EPS waste, for adding value to natural ingredients obtained from biomass. Graphic Abstract
... Terpenes are involved in the primary metabolism of the plant, as hormones, antioxidants and components of the electron transfer system, but also play an important role in more specialized activities [1]. Terpenes, for example, are also involved in chemical communication with insects, both to attract beneficial insects such as pollinators or to repel herbivores [2]. Apart from their role in plant survival, terpenes also possess biological and pharmacological properties that are beneficial to humans [3]. ...
... Their basic structure consists of linked units of the five carbons (C5) molecules dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP) [8], that are the building units of isoprenoids. According to the number of linked subunits and carbons (in brackets), terpenes are classified in hemi-(C5) mono-(C10), sesqui-(C15), di-(C20), sester-(C25), tri-(C30), tetraterpenes (C40) and polyterpenes (C5)n with n > 8 [1,2]. Terpene precursors DMAPP and IPP are synthesized through two independent metabolic pathways: the cytosolic mevalonate (MVA) pathway or the chloroplast methylerythritol phosphate (MEP) pathway [9].In general, isoprene, monoterpenes and diterpenes are synthesized in plastids, while the biosynthesis of sesquiterpenes occurs in the cytosol. ...
... The huge structural diversity of terpenes is the result of the different linkage of the subunits, to the activity of terpene synthase (TPS) enzyme family and to the modification of the resulting terpene skeletons [1]. First, DMAPP and 3 IPP units can be linked to each other through the head (the isopropyl part) or the tail (ethyl residue) and form linear chains or cyclic structures [2,5,8]. Second, TPSs enzymes are a vast family that can count up to 150 genes per genome; these enzymes form the basic terpene skeleton utilizing prenyl diphosphates, formed by the condensation of IPP to DMAPP [10], as precursors, and each TPS can produce multiple products from the same substrate [1,8]. ...
Chapter
Terpenes constitute a highly diverse class of chemical compounds produced by the plant and playing a role in many functions, both physiological and ecological. Plants constantly interact with other organisms, from beneficial to detrimental, and evolved sophisticated regulatory mechanisms to control these interactions. The role of terpenes, or more in general of terpenoids, as preformed or induced chemical deterrents to herbivores is known since long, and their complex role in plant defense against pathogens is increasingly present in the scientific literature. The synthesis of terpenes is one of the responses to attack in numerous plant-pathogen binomials, where terpenes act as specialized or generalized pathogen inhibitors. In this chapter, the involvement of terpenes and terpenoids in resistance to plant pathogens, such as fungi, bacteria, and viruses, and, where relevant, their vectors, is described.
... In nature, a series of natural compounds are produced via biological synthetic pathways consisting of sequential transformation reactions in plants, in which terpenoids are among the most versatile in the chemical structures in terms of linear and cyclic structures, stereostructures including chirality, and functional groups, such as olefins, ketones, and alcohols. [1][2][3][4] These natural compounds with specific chemical structures are not only necessary in their biological activities as attractant or repellent substances but also useful in human activities, functioning as natural oils, flavors, fragrances, and key building blocks for biologically active compounds in pharmaceutical and biotechnology industries. ...
... Verbenone is a main constituent of Spanish verbena and rosemary oils obtained from Verbena triphylla and Rosmarinus officinalis and possesses 4-and 6-membered fused rings similar to one of the most abundant terpenes, α-pinene. [1][2][3][4]30 Indeed, another route to verbenone is chemical or biological oxidation of α-pinene. [31][32][33][34][35][36] Piperitone is a dominant component of essential oils obtained from a family of Eucalyptus dives, Mentha, and Cymbopogon and has a structure similar to hydrogenated carvone in terms of substituents, methyl and isopropyl groups on the cyclohexene ring, whereas the substituted positions are different. ...
... [31][32][33][34][35][36] Piperitone is a dominant component of essential oils obtained from a family of Eucalyptus dives, Mentha, and Cymbopogon and has a structure similar to hydrogenated carvone in terms of substituents, methyl and isopropyl groups on the cyclohexene ring, whereas the substituted positions are different. [1][2][3][4]37,38 Piperitone is also obtained by chemical and biological oxidation of limonene and p-menthene. 39,40 Both these α,β-unsaturated carbonyl compounds are used in flavor, fragrance, and medicinal industries. ...
Article
A series of biobased conjugated dienes with exo-methylene and a 6-membered ring was prepared from naturally abundant terpenoids bearing an α,β-unsaturated carbonyl group, such as verbenone, piperitone, or carvone, and cationically polymerized to form novel biobased cycloolefin polymers with characteristic structures originating from natural products. The obtained exo-methylene-conjugated dienes showed high cationic polymerizability comparable to that of vinyl ethers despite the absence of electron-donating heteroatoms. The polymerization proceeded via regioselective 1,4-conjugated addition by initiating systems effective for living cationic polymerization of vinyl ethers, resulting in well-defined polymers with controlled molecular weights and substituted cyclohexenyl rings in the main chain. These polymers showed high glass transition temperatures (Tg) ranging from 110 to 160 °C depending on the substituents. The hydrogenation of the main-chain cyclohexenyl ring resulted in novel biobased cycloolefin polymers with good thermal stability. The reactivity of the exo-methylene-conjugated diene monomers was evaluated by living cationic copolymerizations with a series of vinyl ethers with different reactivities, i.e., isopropyl, isobutyl, and 2-chloroethyl vinyl ether. In particular, the dienes possessing a methyl group at the 4-position, which can generate a conjugated tertiary cation, were more reactive than a representative vinyl ether with an isobutyl substituent. The sequence distribution of the copolymers varied from statistically random to tapered block structures depending on the monomer reactivities. Block copolymerizations of the dienes and vinyl ethers using the same initiating system for sequential monomer addition resulted in well-defined block copolymers bearing high (>100 °C) and low (∼0 °C) Tg segments, of which microphase separation was confirmed by atomic force microscopy of the thin film.
... A number of vinyl compounds are produced in nature and are found in a family of abundant natural compounds, such as terpenoids and phenylpropanoids [22][23][24][25]. As we have proposed, these biobased vinyl compounds can be classified into similar vinyl monomer families, such as nonpolar olefins, styrenes, and acrylic monomers, to those of petroleum-derived monomers, depending on their substituents and structures [26][27][28][29]. ...
... In contrast, among various terpenes [22][23][24][25], the most abundant terpenes are pinene and limonene, which are unconjugated nonpolar olefins without carbonyl or aromatic groups and have difficulty in undergoing radical homopolymerization [49][50][51][52][53][54][55]. However, these unconjugated terpenes are radically copolymerized with electron-deficient polar monomers, such as acrylates and maleimides, resulting in biobased copolymers with a relatively high terpene incorporation ratio of up to 50 mol%. ...
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A series of exo-methylene 6-membered ring conjugated dienes, which are directly or indirectly obtained from terpenoids, such as β-phellandrene, carvone, piperitone, and verbenone, were radically polymerized. Although their radical homopolymerizations were very slow, radical copolymerizations proceeded well with various common vinyl monomers, such as methyl acrylate (MA), acrylonitrile (AN), methyl methacrylate (MMA), and styrene (St), resulting in copolymers with comparable incorporation ratios of bio-based cyclic conjugated monomer units ranging from 40 to 60 mol% at a 1:1 feed ratio. The monomer reactivity ratios when using AN as a comonomer were close to 0, whereas those with St were approximately 0.5 to 1, indicating that these diene monomers can be considered electron-rich monomers. Reversible addition fragmentation chain-transfer (RAFT) copolymerizations with MA, AN, MMA, and St were all successful when using S-cumyl-S’-butyl trithiocarbonate (CBTC) as the RAFT agent resulting in copolymers with controlled molecular weights. The copolymers obtained with AN, MMA, or St showed glass transition temperatures (Tg) similar to those of common vinyl polymers (Tg ~ 100 °C), indicating that biobased cyclic structures were successfully incorporated into commodity polymers without losing good thermal properties.
... Some of terpenoids are made only of isoprene units, others contain additional functional groups, such as hydroxyl, ketone or heterocyclic rings. Due to wide range of metabolic pathways in plants, some of mentioned substances can be oxidized or metabolized to their alcohols, esters, aldehydes, ketones and epoxides analogues and can also form glycosydesters (Breitmaier 2006;Hanson and Roberts 1982;Connolly and Hill 1991). ...
... The mevalonate pathway, described in literature data as HMG-CoA (β-Hydroxy βmethylglutaryl-coenzyme A) reductase pathway or as the isoprenoid pathway, is crucial metabolic pathway in plants (Breitmaier 2006, Tarkowská 2017. Its main products are isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP) (Phillips and Croteau 1999), J o u r n a l P r e -p r o o f which might be used to form isoprenoids, some hormones and biomelecules (e.g. ...
Article
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Plants produce a large variety of natural products. Terpenes seem to be the largest and the most important group of secondary metabolites in conifer trees. They protect the plant from invading pathogens and herbivores by representing constitutive or induced defense mechanisms. Moreover, antioxidant properties of some terpenes have also been shown, suggesting their role in overcoming oxidative stress provoked by internal and external stimuli. The abiotic and biotic stress factors such as drought, temperature fluctuations, air and soil pollution or pathogen attack rearrange the biosynthesis and emission of terpenes, however the response may depend on the stressor type and stress intensity. Although the general composition of terpenes is characteristic for each species, it has been shown that it can even differ between two individual trees. Reaching for the available literature data, the review is focused on systematizing the observed changes in terpene quantity and quality in the three most important forest-forming conifer genera of European temperate climate zone – pine (Pinus sp.), spruce (Picea sp.) and fir (Abies sp.). Moreover, in view of progressive climate change, the study emphasize a complex function of these interesting compounds in trees including interplant signaling in forest communities.
... Their main skeleton includes 30 atoms of carbon and they are composed of isoprene units as their building blocks. Taking into consideration the structure, triterpenes may be divided into linear ones -mainly derivatives of squalene, tetracyclic and pentacyclic, consisting respectively of four and five cycles, however, two-and tricyclic ones are also known [25]. Quintessentially, these substances have anticancer properties as well as anti-inflammatory, anti-oxidative, anti-viral, antibacterial, antisepsis, anti-fatigue, anti-hyperlipidemic, antihypertension, anti-hyperglycemia, anti-ulcerogenic, antiplasmodia, analgesic and immunomodulatory and anti-fungal ones [26][27][28][29][30][31][32]. ...
... Substrate 1 and its methyl ester were esterified at the C-3. This process led to the formation of eight ester-type hybrid derivatives (14)(15)(16)(17)(18)(19)(20)(21), while the corresponding terpene oximes were transformed into iminoester-type hybrid derivatives (22)(23)(24)(25)(26)(27)(28)(29). The initial stability tests clearly show that the resulting compounds are stable under the defined conditions. ...
Article
Triterpenes are a wide and important group of compounds that have several promising pharmacological properties, such as hepatoprotective, anti-inflammatory, anti-HIV, antioxidant, or anticancer activities. Such potent substances can be successfully incorporated in more complex chemical systems e.g. codrugs or pro-drugs that have better pharmacological profile. The codrug is connected with a drug formation pathway to chemically cohere at least two drug molecules to improve positive therapeutic efficiency or decrease side effects. The codrug can be cleaved in the organism to generate effective compounds previously used as substrates. This article presents an overview of codrugs that consist of pentacyclic triterpene moiety that is chosen as a basic codrug moiety due to their wide range of vital activities and another drug molecule fragment. It was found that triterpenoid codrugs are characterized by a wide range of biological activities. However, most of them have anticancer potency.
... Ces communications entre plantes voisines sont souvent étudiées en agriculture lors de la mise en place de couverts végétaux ou la création d'herbicides naturels [59]. [60]. Ils sont classés selon le nombre d'unités isopréniques C5 qui les compose : hemi-(C5), mono-(C10), sesqui-(C15), di-(C20), sester-(C25), tri-(C30) et tetraterpènes (C40). ...
... Biosynthèse La biosynthèse des terpénoïdes dans le genre Lavandula a été présentée dans de nombreuses publications et ne sera que brièvement abordée ici (Figure I-10) [4,60,67,68]. La formation des composés terpéniques peut être séparée en trois phases : ...
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En écologie chimique, les composés organiques volatils (COVs) qui interviennent dans la survie des plantes et leur adaptation à l’environnement présentent un intérêt scientifique majeur. Néanmoins, leur étude nécessite de développer des outils analytiques performants en raison des faibles teneurs en métabolites, de la complexité des mélanges à analyser et de la diversité structurale des molécules d’intérêts. Depuis une quinzaine d’années, les cultures de lavande et lavandin subissent un important déclin en raison de la propagation du dépérissement de la lavande due à une bactérie pathogène (Candidatus Phytoplasma mali) transmise par un insecte (Hyalesthes obsoletus). L’objectif de cette thèse a donc consisté à développer des méthodes de piégeage et d’analyse des COVs potentiellement impliqués dans le dépérissement. Ce travail a été réalisé sur plusieurs variétés de lavande et lavandin symptomatiques ou asymptomatiques, et connues pour être sensibles ou tolérantes au dépérissement. Ainsi, une approche métabolomique combinant la microextraction sur phase solide (SPME) et la chromatographie en phase gazeuse couplée à un spectromètre de masse (GC-MS) a permis de caractériser pour la première fois les composés émis par les racines en laboratoire et sur le terrain. Une deuxième partie a consisté à appliquer une méthode d’extraction en espace de tête dynamique (DHS), une désorption thermique automatisée (ATD) ainsi qu’une analyse par GC-MS permettant de piéger et analyser les COVs émis par les parties aériennes des plantes directement dans leur environnement naturel. Les COVs stockés dans ces mêmes parties aériennes (inflorescences et feuilles) ont ensuite été extraits dans l’hexane par extraction assistée aux ultrasons (UAE) et analysés par GC-MS. À la suite du traitement des données par analyses discriminantes (PLS-DA), des marqueurs spécifiques des caractères sensibles/tolérants ainsi que asymptomatiques/symptomatiques ont pu être mis en évidence.
... Vitamin K1 could also be oxidized efficiently, affording the valuable hexahydrofarnesyl acetone 80, a member of sesquiterpenoids and used in jasmine compositions. 18 These reactions and those above are often accompanied by some side products (for examples, see the Supporting Information). ...
... 15c Additional support for the mechanism is found in the 16 O 2 − 18 O 2 tracer experiments. As shown in Scheme S6, when the alkene 62 was oxidized with pure 16 O 2 or 18 O 2 , only 16 Oor 18 O-labeled cleavage product was observed; however, when a mixture of 16 O 2 − 18 O 2 was used, all statistically possible products were formed. The formation of the statistical mixture is consistent with what is expected from the mechanism; that is, the two oxygen atoms in the product 16 originate from two different O 2 molecules, while ruling out a pathway where the cleavage product results from an dioxetane intermediate. ...
Article
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The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn–oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.
... In this article, we present spectroscopic and quantum-chemical evidence for this phenomenon in the monoterpenol α-fenchol ( Figure 1). This compound and its oxidized form fenchone are common natural products produced by many plants [46], including fennel (German: Fenchel), from which they derive their names [47]. α-Fenchol is used as a fragrance in cosmetic products, household cleaners and detergents [48]. ...
Article
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Rotational microwave jet spectroscopy studies of the monoterpenol α-fenchol have so far failed to identify its second most stable torsional conformer, despite computational predictions that it is only very slightly higher in energy than the global minimum. Vibrational FTIR and Raman jet spectroscopy investigations reveal unusually complex OH and OD stretching spectra compared to other alcohols. Via modeling of the torsional states, observed spectral splittings are explained by delocalization of the hydroxy hydrogen atom through quantum tunneling between the two non-equivalent but accidentally near-degenerate conformers separated by a low and narrow barrier. The energy differences between the torsional states are determined to be only 16(1) and 7(1) cm−1hc for the protiated and deuterated alcohol, respectively, which further shrink to 9(1) and 3(1) cm−1hc upon OH or OD stretch excitation. Comparisons are made with the more strongly asymmetric monoterpenols borneol and isopinocampheol as well as with the symmetric, rapidly tunneling propargyl alcohol. In addition, the third—in contrast localized—torsional conformer and the most stable dimer are assigned for α-fenchol, as well as the two most stable dimers for propargyl alcohol.
... The various natural vegetable oils extracted from a wide range of plants differ in their presence and availability according to geographical distribution. Additionally, these natural vegetable oils are considered the backbone of possible materials for sustainability due to their chemical and physical properties because most of them possess a microstructure or macrostructure that contains saturated or unsaturated cyclic structures [18][19][20][21][22]. Likewise, there are saturated or unsaturated hydrocarbon chains, in addition to those with carbohydrate structures or fatty acids; thus, these vegetable oils are divided into categories of natural oils that do not need treatment and others that require efforts to ferment biomass or ferment with microorganisms. ...
Article
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The synthesis of copolymers from renewable resources, such as terpenes and a series of methacrylate monomers, was conducted by emulsion polymerization using ammonium persulfate as the initiator. The polymerization of β-myrcene monomers with ethyl methacrylate, benzyl methacrylate and 2-ethyl hexyl methacrylate monomers is described as a simple approach to obtain a wide range of industrial latex that can be used in many industries; additionally, these products can be vulcanized and converted into sustainable semi-synthetic rubber. The optimized reaction conditions of the copolymers were also investigated. Moreover, the obtained copolymer compositions were characterized, and the glass transition temperatures of the produced copolymers were determined by differential scanning calorimetric (DSC) measurements that clearly indicated their rubbery nature. Additionally, the weight losses of the crystallization, melting and degradation phases were examined by thermogravimetric analysis (TGA). The microstructures of the produced copolymers were determined by quantitative 13 C and 1 H nuclear magnetic resonance (NMR) spectra to validate the composition of the copolymers using 50/50 comonomer reactivity ratios.
... Triterpenes are chemically composed of terpene/isoprene units [86]. These compounds are generally found in stem, bark, leaves and fruit peel of olive plants. ...
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can affect replication or protease activity of coronavirus. The clinical testing and regulatory approvals for these drugs will take time. However, currently there is an urgent requirement of treatment strategies which are safe, effective and can be implemented through readily available products in market. Many plant derived products rich in secondary metabolites having potential health benefits and antimicrobial properties. The olive plant leaf extracts and olive oil are rich sources of secondary metabolites such as phenols (oleuropein and hydroxytyrosol) and terpenoids (oleanolic, maslinic and ursolic acid). These compounds have been used as an effective antiviral agents in the past. The phenolics affect the virus attachment and replication. Whereas, the terpenoids mainly affects the membrane fluidity of the virus. In the recent molecular docking studies, it was found that, these compounds effectively bound to Mpro and 3CL pro protease sites of SARS-CoV-2 and were predicted to affect the replication of the SARS-CoV-2. Apart from antiviral properties, these bioactive compounds possess various other pharmacological properties such as anti-inflammatory, anti-modulatory, anti-thrombotic and anti-oxidative. The olive oil is consumed as a source of dietary fat and is the secret behind the good health in Mediterranean people. The consumption of olive oil is safe and is believed to increase the immunity against various infectious microbes. Hence olive products can be explored in management of COVID-19. In this review the various properties of phenolic and terpenoid compounds found in olives were discussed in the context of COVID-19.
... Among all plant secondary metabolites, terpenes are the most diverse [19]. All living organisms including plants produce terpenes as a product of certain essential physiological function. ...
Chapter
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Plant secondary metabolites include bioactive compounds, such as terpenes, alkaloids, polyphenols, glucosinolates, and carotenoids. Apart from conventional extraction methods (e.g., soxhlet and maceration) several novel technologies with basic extraction processes have been developed to extract secondary metabolites from various plant parts and sources. Such extraction methods are high pressure-assisted (HPA), negative pressure cavitation-assisted (NPCA), high-pressure homogenization-assisted (HPHA), high voltage electrical discharge-assisted (HVEDA), microwave-assisted (MA), ultrasound-assisted (UA), moderate electric field-assisted extraction (MEFA) and pulsed electric fields-assisted (PEFA), enzyme-assisted (EA), and chemical pretreatment methods. Therefore, applications of plant secondary metabolites in pharmaceuticals, foods, and cosmetics are noteworthy. This chapter focuses on the characteristics of selected plant secondary metabolites, techniques for their industrial production, and applications.
... The mevalonic acid (MVA) pathway is the first to be formed, later becoming the 2-C-methyl-D-erythritol 4-phosphate (MEP) pathway. Terpenoids are primarily categorized by their number of isoprene units, and then categorized into hemiterpenoids (one isoprene unit with five carbons), monoterpenoids (two isoprene units with 10 carbons), sesquiterpenoids (three isoprene units with 15 carbons), diterpenoids (four isoprene units with 20 carbons), triterpenoids (six isoprene units with 30 carbons), tetraterpenoids (eight isoprene units with 40 carbons), and polyterpenoids ((C 5 )n with n > 8) [7]. Iridoids are derived from monoterpenes, which are typically found in plants as glycosides. ...
Article
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The root of Phlomis umbrosa has traditionally been used as a medicine in South Asian nations to treat colds and bone fractures, to staunch bleeding, and as an anti-inflammatory, and such use continues today. We identified 10 genes that are involved in terpenoid biosynthesis, while using the Illumina/Solexa HiSeq2000 platform. We investigated the transcript levels of the 10 genes using quantitative real-time PCR and quantified the level of terpenoid accumulation in different organs of P. umbrosa while using high-performance liquid chromatography. The transcript levels of PuHDR and PuHMGR1 were the highest among the studied genes. Sesamoside, an iridoid glycoside, appeared in higher quantity than shanzhiside methylester, umbroside (8-O-acetyl shanzhiside methyl ester), and acteoside. We speculate that PuHDR and PuHMGR1 may contribute to terpenoid biosynthesis in P. umbrosa. This study highlights the molecular mechanisms that underlie iridoid glycoside biosynthesis in P. umbrosa.
... Terpenoid adalah modifikasi struktur dari terpena (lima karbon isoprena) yang tidak hanya mengandung hidrokarbon simpel tetapi mengandung berbagai gugus fungsi dan metil teroksidasi. Diantara berbagai metabolit sekunder yang ada, terpena merupakan salah satu golongan metabolit sekunder yang terbesar dan beragam (Breitmaier, 2006). Terpenoid dihasilkan sebagai respons mekanisme pertahanan yang beragam seperti gangguan membran, penginderaan antikuorum, penghambatan sintesis protein dan ATP. ...
Book
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Buku ini berisikan kajian tema-tema sosial ekonomi masyarakat lahan basah, paparan dan teori lingkungan dan ilmu dasar di lahan basah, serta kebencanaan di lahan basah. Paparan kajian-kajian tersebut merupakan hasil studi dan penelitian serta rekomendasi peneliti Universitas Riau (Unri) untuk pengelolaan lahan basah yang lebih ecofriendly dan terjaga sustainabilitinya. Semoga dengan adanya buku referensi ini diharapkan penyampaian materi kuliah akan lebih baik. Tim editor mengucapkan terima kasih kepada kontributor yang telah menyumbangkan materi dari hasil kajian lahan basah. Untuk penyempurnaan di masa yang akan datang, kritik dan saran sangatlah diperlukan.
... Monoterpen ve seskiterpenlerdir, birçok bitkide bulunur. Doğada var olan 30000' den fazla bilinen terpen vardır (Breitmaier, 2006;Tholl, 2015). Kannabinoidlerin ve/veya terpenlerin, bilinen Kenevirin tad ve aromasına katkıda bulunan terpenler çoğunlukla monoterpen ve seskiterpenlerdir (Andre vd., 2016). ...
... The parental skeleton of monoterpenoids are generally classified as acyclic, monocyclic and bicyclic terpenoids (Pfander and Stoll 1991), while the monoterpenes found in the aglycone fraction of fruits are derivatives from different chemical classes including hydrocarbons, alcohols, acids, aldehyde and polyols. Acyclic hydrocarbon monoterpenes mainly comprise b-myrcene and trans-b-ocimene in the oils of petitgrain, hops, bay and basil (Breitmaier 2006). Beta-myrcene is octa-1,6-diene attached to methylene and methyl substituents, appearing as a yellow oily liquid with a pleasant odor, while b-ocimene consists of octa-1,3,6-triene bearing two methyl substituents, producing pleasant odor . ...
Article
Fruit aroma is mainly contributed by free and glycosidically bound aroma compounds, in which glycosidically bound form can be converted into free form during storage and processing, thereby enhancing the overall aroma property. In recent years, the bound aroma precursors have been widely used as flavor additives in the food industry to enhance, balance and recover the flavor of products. This review summarizes the fruit-derived aroma glycosides in different aspects including chemical structures, enzymatic hydrolysis, biosynthesis and occurrence. Aroma glycosides structurally involve an aroma compound (aglycone) and a sugar moiety (glycone). They can be hydrolyzed to release free volatiles by endo- and/or exo-glucosidase, while their biosynthesis refers to glycosylation process using glycosyltransferases (GTs). So far, aroma glycosides have been found and studied in multiple fruits such as grapes, mangoes, lychees and so on. Additionally, their importance in flavor perception, their utilization in food flavor enhancement and other industrial applications are also discussed. Aroma glycosides can enhance flavor perception via hydrolyzation by β-glucosidase in human saliva. Moreover, they are able to impart product flavor by controlling the liberation of active volatiles in industrial applications. This review provides fundamental information for the future investigation on the fruit-derived aroma glycosides.
... An in-depth discussion on terpenoids' biosynthetic pathway and structural diversity is covered by Aharoni et al. (2005) and Song et al. (2014) in their review [31,32]. More than 30,000 terpenes have been reported to date [33]. They are mostly phytohormones (e.g., gibberellins), photosynthetic pigments (e.g., phytol, carotenoids such as α-carotene and β-carotene), and carriers (e.g., ubiquinone, plastoquinone) in the electron chain transport systems [34,35]. ...
Article
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Plant secondary metabolites (PSMs) are vital for human health and constitute the skeletal framework of many pharmaceutical drugs. Indeed, more than 25% of the existing drugs belong to PSMs. One of the continuing challenges for drug discovery and pharmaceutical industries is gaining access to natural products, including medicinal plants. This bottleneck is heightened for endangered species prohibited for large sample collection, even if they show biological hits. While cultivating the pharmaceutically interesting plant species may be a solution, it is not always possible to grow the organism outside its natural habitat. Plants affected by abiotic stress present a potential alternative source for drug discovery. In order to overcome abiotic environmental stressors, plants may mount a defense response by producing a diversity of PSMs to avoid cells and tissue damage. Plants either synthesize new chemicals or increase the concentration (in most instances) of existing chemicals, including the prominent bioactive lead compounds morphine, camptothecin, catharanthine, epicatechin-3-gallate (EGCG), quercetin, resveratrol, and kaempferol. Most PSMs produced under various abiotic stress conditions are plant defense chemicals and are functionally anti-inflammatory and antioxidative. The major PSM groups are terpenoids, followed by alkaloids and phenolic compounds. We have searched the literature on plants affected by abiotic stress (primar-ily studied in the simulated growth conditions) and their PSMs (including pharmacological activities) from PubMed, Scopus, MEDLINE Ovid, Google Scholar, Databases, and journal websites. We used search keywords: "stress-affected plants," "plant secondary metabolites, "abiotic stress," "climatic influence," "pharmacological activities," "bioactive compounds," "drug discovery," and "medicinal plants" and retrieved published literature between 1973 to 2021. This review provides an overview of variation in bioactive phytochemical production in plants under various abiotic stress and their potential in the biodiscovery of therapeutic drugs. We excluded studies on the effects of biotic stress on PSMs.
... They are commonly mixed with other oils to make them more easily absorbed by human skin. This supports the moisturizing process, which explains the oil's presence in skin products like a natural sunscreen [2,12]. ...
... Terpenes are characterized by the isoprene unit (C 5 ) and form a large group of phytochemicals as the sources of pleasant smell, spicy taste and numerous pharmacological activities [17]. Monoterpenes have a carbon skeleton of two isoprene units (C 10 skeleton), and some have one or two cycloalkane units such as cyclopropane, cyclobutane and cyclohexane. ...
Article
Ginger (Zingiber officinale Roscoe) has been used as a food, spice, supplements, flavoring agent and in traditional medicines due to its beneficial characteristics such as pungency, aroma, nutrients and pharmacological activity. Ginger and ginger extracts were reported to have numerous effects, such as those on diabetes and metabolic syndrome, cholesterol levels and lipid metabolism, and inflammation, revealed by epidemiological studies. To understand the beneficial characteristics of ginger, especially its physiological and pharmacological activities at the molecular level, the biological effects of ginger constituents, such as monoterpenes (cineole, citral, limonene and α/β-pinenes), sesquiterpenes (β-elemene, farnesene and zerumbone), phenolics (gingerols, [6]-shogaol, [6]-paradol and zingerone) and diarylheptanoids (curcumin), and the associated signaling pathways are summarized. Ginger constituents are involved in biological activities, such as apoptosis, cell cycle/DNA damage, chromatin/epigenetic regulation, cytoskeletal regulation and adhesion, immunology and inflammation, and neuroscience, and exert their effects through specific signaling pathways associated with cell functions/mechanisms such as autophagy, cellular metabolism, mitogen-activated protein kinase (MAPK) and other signaling, and development/differentiation. Estrogens, such as phytoestrogens, are one of the most important bioactive materials in nature, and the molecular mechanisms of estrogen actions and the assays to detect them have been discussed. The molecular mechanisms of estrogen actions induced by ginger constituents and related applications, such as the chemoprevention of cancers, and the improvement of menopausal syndromes, osteoporosis, endometriosis, prostatic hyperplasia, polycystic ovary syndrome and Alzheimer's disease, were summarized by a comprehensive search of references to understand more about their health benefits and associated health risks.
... Repetitive joining of isoprene units produce C10 family which considered the smallest, named the monoterpenes, by continuing addition of isoprene unit sesquiterpenes (C15), diterpenes (C20), sesterterpenes (C25), triterpenes (C30), tetraterpenes (C40), and polyterpenes produced that is (>C40). They demonstrate huge number of compounds in nature and intensively in plant kingdom (75,76) . Terpenoids are terpenes that have been modified with oxygen containing functional groups. ...
Thesis
Certificate I certify that this thesis entitled (Phytochemical Investigation, isolation of new medicinal compounds and evaluation of anti-inflammatory activity of Parthenocissus quinquefolia L. cultivated in Iraq) was prepared under our supervision at the Certificate We, the Examining Committee after reading this thesis entitled (Phytochemical Investigation, isolation of new medicinal compounds and evaluation of anti-inflammatory activity of Parthenocissus quinquefolia L. cultivated in Iraq) and examining the student (Nour Rasim Esmail) in its content, found it adequate as a partial fulfillment of the requirements for the
... Volatile aromatic compounds vary with cultivars due to which various basils have distinct scents (Simon, 1998). Linalool and methyl chavicol are found in high concentration (3:1 ratio) in essential oils from Europium basil (Simon, 1998;Lee et al., 2005) while 1,8-cineole, eugenol and myrcene are other constituents (Simon, 1998;Breitmaier, 2006). Sweet basil based clove scent is derived from eugenol (Islam, 2011) while 1,8-cineole (Johnson et al., 1999;Baritaux et al., 1992) and methyl eugenol (Johnson et al., 1999;Miele et al., 2001) are included in aroma profile of basil (Basil, https://en.wikipedia.org/wiki/Basil). ...
Chapter
Essential oils are plant based hydrophobic liquids. They are also called as volatile oils due to the presence of volatile compounds. Every essential oil has its characteristic fragrance specific of that plant from which it is extracted. Essential oils have varieties of valuable applications due to their individual specific fragrances. They have wide roles in giving savory properties and different flavors to food materials, in making specific beverages, in making perfumes, cosmetics and scents, in giving specific fragrances to various man made materials for their daily uses and in many other applications. Besides the above properties and uses of essential oils, they have also the valuable roles in the field of traditional medications and Ayurveda. Specific therapy based on essential oils is called as aromatherapy. On the basis of recent researches and scientific updates, this chapter describes about the different uses and effective roles of some essential oils that may be due to their specific properties, compositions and odor.
... Terpene and terpenoid groups are a large and diverse class of organic compounds, produced by a variety of medicinal and aromatic plants [70]. Terpenes such as (+)delta-cadinene (C06394), phytol (C05427), ascaridole (EMBL-EBI: CHEBI:2866) play important roles in various pathways such as (sesquiterpenoid and triterpenoid biosynthesis; KEGG: map00909, Biosynthesis of terpenoids and steroids; KEGG: map01062, metabolic pathways; KEGG: map01100, biosynthesis of secondary metabolites; KEGG: map01110, ubiquinone and other terpenoid-quinone biosynthesis; KEGG: map00130, terpenoid backbone biosynthesis; KEGG: map00900 and biosynthesis of plant secondary metabolites; KEGG: map01060) through different biochemical reactions such as (KEGG: R02311, R08371, R02063, R04795, R06284, R07500, R08756, R09067 and R12255) (KEGG: https://www.genome.jp/dbget-bin/www_bget?C06394; https://www.kegg.jp/dbgetbin/www_bget?C05427; EMBL-EBI: https://www.ebi.ac.uk/chebi/searchId.do?chebiId= CHEBI:2866 (accessed on 1 January 2020)). ...
Article
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Available information associated with Calotropis procera posted its phytotoxic effect as bio-herbicide scarce works studied its stimulatory/nutritive effect. A pot experiment was performed to assess the validity of using Calotropis procera (C. procera) leaves extract as a bio-stimulant for the growth and quality of a medicinal plant Catharanthus roseus (C. roseus) evaluated by some physio-biochemical indices. Different types of C. procera leaves extracts (CLEs) (methanolic, cold water and autoclaved water extracts) were delivered by two different modes of application. The results revealed that application of CLEs as irrigation or foliar spraying caused a stimulation effect on C. roseus plant. Root and shoot length, dry and fresh weight were significantly improved due to CLEs applications. C. roseus bioactive molecules such as anthocyanins, phenolics, flavonoids, alkaloids, ascorbic acid, reduced glutathione and α-tocopherol were abundance increased significantly with CLEs applications. Reactive oxygen species (ROS) decreased explaining the involvement of CLEs in induction of antioxidant enzymes catalase, ascorbate peroxidase, polyphenol oxidase, guaiacol peroxidase and glutathione-S-transferase for modifying cell oxidative status witnessed by lower lipid peroxidation that kept below the untreated plants’ baseline reflected the improvement of growth and quality rather than phytotoxic effect. The promotion of wholesome-promoting secondary metabolites by CLEs was closely correlated to elevated phenylalanineammonialyase activity. The comparable efficient effect induced by all treatments might be judged by the relation between C. procera phytochemicals and C. roseus metabolism (donor-receiver relation). It is concluded that application of CLEs can be a promising approach for improving the yield and quality of plants despite using polluting fertilizers. The current investigation may provide a matrix for coming studies to seek illustration of numerous plants’ response to C. procera extracts.
... Pinene is a bicyclic monoterpene that consists of two isoprene units and has the molecular formula C 10 H 16 (63). Differentiated by their physical structure, α-pinene is recognised for the alkene located inside the six-membered ring and β-pinene for its placement on the outside of the ring ( Figure 5). ...
Article
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“Medicinal cannabis” is defined as the use of cannabis-based products for the treatment of an illness. Investigations of cannabis compounds in psychiatric and neurological illnesses primarily focus on the major cannabinoids, cannabidiol (CBD) and Δ ⁹ -tetrahydrocannabinol (Δ ⁹ -THC), which are hypothesised to benefit multiple illnesses manifesting cognitive impairment, neurodegeneration and neuro-inflammation, as well as chronic pain, epilepsy and post-traumatic stress disorder, respectively. The cannabis plant contains >500 compounds, including terpenes responsible for the flavour and fragrance profiles of plants. Recently, research has begun providing evidence on the potential use of certain plant-derived terpenes in modern medicine, demonstrating anti-oxidant, anti-inflammatory, and neuroprotective effects of these compounds. This review examined the effects of two key terpenes, pinene and linalool, on parameters relevant to neurological and psychiatric disorders, highlighting gaps in the literature and recommendations for future research into terpene therapeutics. Overall, evidence is mostly limited to preclinical studies and well-designed clinical trials are lacking. Nevertheless, existing data suggests that pinene and linalool are relevant candidates for further investigation as novel medicines for illnesses, including stroke, ischemia, inflammatory and neuropathic pain (including migraine), cognitive impairment (relevant to Alzheimer's disease and ageing), insomnia, anxiety, and depression. Linalool and pinene influence multiple neurotransmitter, inflammatory and neurotrophic signals as well as behaviour, demonstrating psycho-activity (albeit non-intoxicating). Optimising the phytochemical profile of cannabis chemovars to yield therapeutic levels of beneficial terpenes and cannabinoids, such as linalool, pinene and CBD, could present a unique opportunity to discover novel medicines to treat psychiatric and neurological illnesses; however, further research is needed.
... They constitute a family of low molecular weight compounds with an important influence on human life, due to their applications in medicine, food, and cosmetics. Essential oils are terpene-related secondary metabolites responsible of the fragrance of plants [80]. Terpenes are polymers of isoprene (C5H8) and can be classified in 8 classes-hemiterpenes, monoterpenes, sesquiterpenes, diterpenes, sesterterpenes, triterpenes, tetraterpenes, and polyterpenes, which differ in the number of isoprene units. ...
Article
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The vegetal world constitutes the main factory of chemical products, in particular secondary metabolites like phenols, phenolic acids, terpenoids, and alkaloids. Many of these compounds are small molecules with antibacterial activity, although very few are actually in the market as antibiotics for clinical practice or as food preservers. The path from the detection of antibacterial activity in a plant extract to the practical application of the active(s) compound(s) is long, and goes through their identification, purification, in vitro and in vivo analysis of their biological and pharmacological properties, and validation in clinical trials. This review presents an update of the main contributions published on the subject, focusing on the compounds that showed activity against multidrug-resistant relevant bacterial human pathogens, paying attention to their mechanisms of action and synergism with classical antibiotics.
... The most important terpenes in rosemary belong to mono-, -di, and triterpenes. Terpenes can also contain different functional groups within their structure, which in rosemary predominantly belong to alcohols (e.g., borneol), ketones (e.g., verbenone), ethers (e.g., 1,8-cineol), esters (e.g., carnosol) or carboxylic acids (e.g., carnosic acid) (Breitmaier 2006). ...
Article
Full-text available
Rosemary (Rosmarinus officinalis L.) of the Lamiaceae family represents an evergreen medicinal plant with various health-promoting pharmacological effects. This paper provides a complete overview of diverse biological activities of rosemary extracts, essential oils as well as their numerous bioactive compounds, ranging from antioxidative, anti-inflammatory, and antimicrobial over cognitive enhancing to their anticarcinogenic effects. In addition, state of the art extraction, distillation, fractionation, and characterization techniques for obtaining high-quality rosemary extracts and essential oils as well as methods for determining their antioxidative, antimicrobial, anti-inflammatory, and anticarcinogenic potentials are also presented. Finally, new ideas for future computational studies on chemical reactivities and binding affinities of health-promoting rosemary compounds together with suggestions for their improved bioavailability through diverse encapsulation techniques are introduced.
... Terpenes are a large, diverse class of organic compounds, made by various plants, especially conifers, and by some insects (75,76). Terpenes are hydrocarbons. ...
Article
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The research focused on the biochemistry and the medicinal uses of alkaloids, terpenes,polyphenols, and glycosides. Several parts of plants such as bark, root, leaf, stem, etc. are being used torevert abnormalities back to normal, prevent illnesses, or allay symptoms. These plant parts containbioactive compounds such as terpenes, glycosides, polyphenols, and alkaloids. Alkaloids have a rangeof pharmacological activities such as antiasthma (e.g. ephedrine), anticancer (e.g. homoharringtonine),antimalarial (e.g. quinine). Other alkaloids possess stimulant (e.g. cocaine, caffeine, theobromine, nicotine)and psychotropic activities (e.g. psilocin), and have been widely used as recreational drugs orin entheogenic rituals. Alkaloids can be toxic too (e.g. tubocurarine, atropine). Although alkaloids act ondiverse metabolic systems in humans and animals, they almost uniformly induce a bitter taste. Thecharacteristics and number of the structures of phenol in polyphenols underlie the unique chemical,physical, and biological (metabolic, therapeutic, toxic, etc.) properties of specific members of the class;e.g. ellagitannin and tannic acid. Generally, foods often contain complex mixtures of polyphenols. Severalpolyphenolic extracts, such as from grape seeds, olive pulp, maritime pine bark, or grape skin, are sold asingredients for functional foods, cosmetics, and dietary supplements. Terpenoids and terpenes are theprimary components of the essential oils of most types of flowers plants. Essential oils are used widely asscents and fragrances in perfumery and also in traditional medicine, such as aromatherapy. Similarly,many plant glycosides are used as medicines. Amygdalin and laetrile (a synthetic derivative) wereinvestigated as potential drugs for cancer treatment and were promoted as alternative medicine;nevertheless, they are ineffective and dangerous. Pharmacologically active phytochemicals can haveuseful applications, as well as safety concerns.
... Diterpenes are a class of chemical compounds which are biosynthesized by plants, animals and fungi (19). Diterpenes form the basis for two biologically important compounds, retinol (Vitamin A1) and phytol (20). ...
Article
Cancer stem cells (CSCs), a subgroup of cancer cells, have self-renewal capacity and differentiation potential and drive tumor growth. CSCs are highly-resistant to conventional chemo-radio therapy. Phytochemicals were shown to be able to eliminate CSCs. Phytol is a diterpene alcohol with demonstrated anticancer effects. The current study compared the effect of phytol with retinoic acid (RA) as a well-known inducers of CSC differentiation and cisplatin, a common chemotherapy drug, on CSC markers in human embryonic carcinoma NCCIT cells. NCCIT cells were exposed to 10 mM RA for 14 day to induce differentiation. Moreover, NCCIT cells were treated with IC50 dose of cisplatin (12 µM) and phytol (40 µM) for 7 day. Real-time PCR showed that phytol was more effective that RA and cisplatin in down-regulating the CSC markers OCT4, NANOG, SOX2, ALDH1, ABCB1, CD44 and CD133. Percentage of SP (13%) and ABCB1⁺ (0.34%) in NCCIT cells decreased to 7% and 0.1% respectively after treatment with phytol. A very small proportion of NCCIT cells were positive for CD44 (0.2%) and CD133 (0.48%) and this fraction did not change significantly after treatment with three agents. In conclusion, phytol has the greatest inhibitory effect on CSC population and markers than RA and cisplatin.
... 32 There are two possible isomers of myrcene, α and β, but the natural occurring one is the β-isomer. β-Myrcene is a readily available terpene that can be obtained from various essential oils, such as ylang-ylang, hops, bay, thyme or cannabis, but in fact it is more economical to produce it from the pyrolysis of β-pinene, 9,33 since β-pinene is more abundant and can be easily isolate from turpentine oils. The isomer ocimene is produced from the thermal cracking of α-pinene and can isomerize at high temperature to give alloocimene. ...
Chapter
Terpenes and their oxygenated derivatives, terpenoids, are synthesized mainly by plants and are found in flowers, fruits, trees and spices. They are one of the largest family of natural products synthesized as secondary metabolites. A remarkable structurally different terpenes can be found, including acyclic, monocyclic, bicyclic and polycyclic structures. In all cases, they present functional groups which render them as interesting precursors for the synthesis of new added-value chemicals. From a chemical point of view, terpenes are hydrocarbon units with double bonds, hence there are suitable natural substitutes of oil-derived monomers; however, terpene polymerization is an area that has been little explored. In this chapter, an overview of the most commonly studied terpenes and terpenoids in polymerization processes catalyzed by metal compounds is given. In some cases, such as the copolymerization of 1,2-limonene-oxide with CO2 to give polycarbonates, polymers that can compete with the oil-derived ones have been produced which shown the great potential that this family of natural products entails. The polymerization of terpenes and terpenoids is an exciting area that is only now awakening.
... Terpenoids are the most essential, common worldwide, and major group of secondary metabolites among the main plant species. The name terpenoid has originated from turpentine acquired from pine resins (Breitmaier 2006). Around 25,000 terpenoids are derived biosynthetically from five-carbon precursor isopentenyl diphosphate (IPP) by mevalonic acid biosynthetic pathway (Rodney et al. 2000;Thirumurugan et al. 2018). ...
Chapter
Nature, the supreme artist, and scientists have designed almost an infinite range of plant molecular bioactive molecules for drugs operative for the remedy of innumerable human disorders in the biosynthetic laboratory of plants. From 250,000 to 300,000 plant species which exist on Earth, only about 5000 were investigated for chemical compounds with pharmacological and biological activities. More than 25% of pharmaceutical molecules are plant based through sequestration of the novel bioactive compounds. The 200,000 known secondary metabolites with widespread chemical structures are manly categorized into phenolics, terpenoids or terpenes, and steroids and alkaloids. Secondary metabolites perform significant functions in plants including role as signaling molecules, chemical defense mechanism and adaptation, pollination and seed dispersal, protection from predators, herbivores, pathogens, and allelopathic agents. Medicinal and aromatic plants (MAPs) are bestowed with both the aromatic and medicinal properties and contain bioactive secondary metabolites with a broad range of pharmacological and therapeutic potentials such as antioxidant, antitumor, anticancer, antiviral, antimicrobial, anti-inflammatory, antiatherosclerotic, antidepressant, antidiabetic, hepatoprotective, antithrombotic, vasoprotective, and immunoprotective effects, cardiovascular improver, memory enhancer, anti-AIDS, anti-Alzheimer’s, anti-Parkinson’s disease, and anti-cognitive impairment.
... their structures is responsible for diverse functions, such as photosynthetic pigments (phytol, carotenoids), hormones (gibberellins), electron carriers (ubiquinone, plastoquinone), communication, defense mechanisms, etc. Different terpene derivatives (terpenoids) possess anticancer, antifungal, antimicrobial, antiviral, antiparasitic, anti-inflammatory, antihyperglycemic, and immunomodulatory properties (2). Monoterpenes (geraniol, limonene, and menthol), sequiterpenes (valencene, humulene, artemisinin, zerumbone, and nootkatone), and diterpenes (paclitaxel and sclareol) are currently in use in therapeutic (artemisinin, zerumbone, paclitaxel, etc.) and flavor/fragrance (menthol, nootkatone, linalool, and sclareol) industries (1). Ever-increasing knowledge about their properties related to health and well-being have continued to increase the demand for them. ...
Article
Full-text available
To date, the major host organisms used for the heterologous production of terpenoids, i.e., E. coli and S. cerevisiae , do not have high-flux isoprenoid pathways and involve tedious metabolic engineering to increase the precursor pool. Since carotenoid-producing bacteria carry endogenous high-flux isoprenoid pathways, we used a carotenoid-producing mutant of A. brasilense as a host to show its suitability for the heterologous production of geraniol and amorphadiene as a proof-of-concept. The advantages of using A. brasilense as a model system include (i) dispensability of carotenoids and (ii) the possibility of overproducing carotenoids through a single mutation to exploit high carbon flux for terpenoid production.
... Cembrane is one of the largest and most structurally diverse diterpenoids; it has a 14-membered macrocyclic backbone and is biogenetically derived from the cyclization of a precursor, geranylgeranyl pyrophosphate (GGPP) (Breitmaier, 2006). A large number of cembranoids have been obtained from marine organisms and terrestrial plants in recent years. ...
Article
Ten undescribed cembrane-type diterpenes boscartins AL-AU, as well as five known analogues were isolated from Boswellia sacra Flueck. The relative configurations of these boscartins were established by extensive spectroscopic analysis of NMR spectra, IR and MS. The absolute configurations of boscartin AL, boscartin AN and isoincensole oxide were unequivocally assigned by single crystal X-ray diffraction. Meanwhile, the absolute configurations of boscartin AM, boscartin AP and boscartin AQ were determined by an empirical in situ formed Rh-complex ECD method. Biological evaluations showed that four compounds exhibited obvious hepatoprotective activities against paracetamol-induced HepG2 cell damage at 10 μM. Regarding neuroprotective activity, some isolates displayed moderate to evident protective effects against glutamate-induced toxicity in primary cultured fetal rat cortical neurons or oxygen-glucose deprivation toxicity in SK-N-SH Cells at 10 μM.
... Sesquiterpene lactones (SQLs) constitute a family of bioactive natural products isolated from various plants. 1 Members of this family containing an α-methylene-γ-lactone moiety have recently attracted significant attention because of their promising anticancer properties, especially in the context of leukemias. 2−4 Previous studies indeed showed that parthenolide (PTL) and semisynthetic derivatives thereof are capable of targeting and killing acute myeloid leukemia (AML) cells as well as leukemia stem cells (LSCs). ...
Article
Full-text available
The plant-derived sesquiterpene lactone micheliolide was recently found to possess promising antileukemic activity, including the ability to target and kill leukemia stem cells. Efforts toward improving the biological activity of micheliolide and investigating its mechanism of action have been hindered by the paucity of preexisting functional groups amenable for late-stage derivatization of this molecule. Here, we report the implementation of a probe-based P450 fingerprinting strategy to rapidly evolve engineered P450 catalysts useful for the regio- and stereoselective hydroxylation of micheliolide at two previously inaccessible aliphatic positions in this complex natural product. Via P450-mediated chemoenzymatic synthesis, a broad panel of novel micheliolide analogs could thus be obtained to gain structure–activity insights into the effect of C2, C4, and C14 substitutions on the antileukemic activity of micheliolide, ultimately leading to the discovery of “micheliologs” with improved potency against acute myelogenic leukemia cells. These late-stage C–H functionalization routes could be further leveraged to generate a panel of affinity probes for conducting a comprehensive analysis of the protein targeting profile of micheliolide in leukemia cells via chemical proteomics analyses. These studies introduce new micheliolide-based antileukemic agents and shed new light onto the biomolecular targets and mechanism of action of micheliolide in leukemia cells. More broadly, this work showcases the value of the present P450-mediated C–H functionalization strategy for streamlining the late-stage diversification and elucidation of the biomolecular targets of a complex bioactive molecule.
... Triterpenes, a group of terpenes consisting of six isoprene units, have been identified in more than 200 skeletons, with about 20,000 different terpenes reported to date [30]. Triterpenes contain 30 carbons and can be found in linear, dicyclic, tricyclic, tetracyclic, and pentacyclic forms that are mainly derived from squalene [31]. The prominent members of this group show antiviral, antibacterial, antifungal, antioxidant, anticancer, and anti-inflammatory activities [32]. ...
Article
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Plant secondary metabolites (SMs) play important roles in plant survival and in creating ecological connections between other species. In addition to providing a variety of valuable natural products, secondary metabolites help protect plants against pathogenic attacks and environmental stresses. Given their sessile nature, plants must protect themselves from such situations through accumulation of these bioactive compounds. Indeed, secondary metabolites act as herbivore deterrents , barriers against pathogen invasion, and mitigators of oxidative stress. The accumulation of SMs are highly dependent on environmental factors such as light, temperature, soil water, soil fertility , and salinity. For most plants, a change in an individual environmental factor can alter the content of secondary metabolites even if other factors remain constant. In this review, we focus on how individual environmental factors affect the accumulation of secondary metabolites in plants during both biotic and abiotic stress conditions. Furthermore, we discuss the application of abiotic and biotic elicitors in culture systems as well as their stimulating effects on the accumulation of secondary metabolites. Specifically, we discuss the shikimate pathway and the aromatic amino acids produced in this pathway, which are the precursors of a range of secondary metabolites including terpenoids, alkaloids, and sulfur-and nitrogen-containing compounds. We also detail how the biosynthesis of important metabolites is altered by several genes related to secondary metabolite biosynthesis pathways. Genes responsible for secondary metabolite biosynthesis in various plant species during stress conditions are regulated by transcriptional factors such as WRKY, MYB, AP2/ERF, bZIP, bHLH, and NAC, which are also discussed here.
... Terpenoid adalah modifikasi struktur dari terpena (lima karbon isoprena) yang tidak hanya mengandung hidrokarbon simpel tetapi mengandung berbagai gugus fungsi dan metil teroksidasi. Diantara berbagai metabolit sekunder yang ada, terpena merupakan salah satu golongan metabolit sekunder yang terbesar dan beragam (Breitmaier, 2006). Terpenoid dihasilkan sebagai respons mekanisme pertahanan yang beragam seperti gangguan membran, penginderaan antikuorum, penghambatan sintesis protein dan ATP. ...
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