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Search for "terpenoids" in Full Text gives 73 result(s) in Beilstein Journal of Organic Chemistry.
Terpenoids from Glechoma hederacea var. longituba and their biological activities
Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58
- , lignans, flavonoids, and phenolic compounds that show anti-inflammatory, cytotoxic, and/or cytoprotective effects [3][4][5][6][7]. However, bioactive terpenoids of G. hederacea var. longituba with antineurodegenerative effects remain largely unknown. In this study, nine terpenoids (1–9) including five new
Targeting active site residues and structural anchoring positions in terpene synthases
Beilstein J. Org. Chem. 2021, 17, 2441–2449, doi:10.3762/bjoc.17.161
- mechanisms; isotopes; site-directed mutagenesis; terpenes; Introduction Terpenoids now span more than 90,000 known compounds, which makes them by far the largest class of natural products [1]. Despite this fact, all compounds are made from only two C5 building blocks, dimethylallyl diphosphate (DMAPP) and
Volatile emission and biosynthesis in endophytic fungi colonizing black poplar leaves
Beilstein J. Org. Chem. 2021, 17, 1698–1711, doi:10.3762/bjoc.17.118
- volatile blends of plants consist of different compound classes, including green leaf volatiles, benzenoids, terpenoids, and nitrogen-containing compounds [5][6][7]. Among these, terpenoids represent the largest and most diverse group of compounds. In poplar trees, large amounts of terpenoids can be
- emitted constitutively [8][9] and facilitate protection against thermal and oxidative stresses [10]. In addition, terpenoids are also produced in response to biological stresses such as herbivory [9][11] and can fulfill different functions in plant–insect interactions. For instance, together with other
- volatiles, some terpenoids are known to attract natural enemies of insect herbivores [2][12][13] or attract insects as shown for the sesquiterpene (E)-β-caryophyllene (1) [14][15]. Another sesquiterpene, (E)-β-farnesene (2), an aphid alarm pheromone, is also produced by plant species like Arabidopsis
A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries
Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90
- applied on terpenoids are abundant in the literature. As terpenoids are one of the most important odorants in the F&F industry. Schütz et al. developed an aldol condensation of citral (79, 63:37 mixture of geranial (Z)-79/neral (E)-79) with acetone to prepare ψ-Ionone or pseudoionone (80) in good yield
Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones
Beilstein J. Org. Chem. 2021, 17, 1048–1085, doi:10.3762/bjoc.17.84
- enantioselectivities (85–99% ee; entry 1; Table 25) and used in the total synthesis of terpenoids (Scheme 14) [10]. In the same year, these terpenoids were also prepared by the Stoltz group [11]. Arylboronic acids bearing the appropriate functional groups were identified and the addition reactions to 3-methyl-2
- -cyclohexenone were studied (entries 2–6, Table 25) [11]. The product, which was obtained in an almost quantitative yield and practically maximal possible enantioselectivity (entry 5 in Table 25), was subsequently converted to suitable intermediates for the synthesis of naturally occurring terpenoids (Scheme 14
- syntheses of the natural products (−)-caesalpinnone A and (−)-caesalpinflavan B [9]. Plausible catalytic cycle for the addition of phenylboronic acid to 3-methyl-2-cyclohexenone catalysed by L9/Pd(TFA)2 [48][49]. Total syntheses of naturally occurring terpenoids [10][11]. Use of the L9/Pd(TFA)2 catalytic
Stereoselective synthesis and transformation of pinane-based 2-amino-1,3-diols
Beilstein J. Org. Chem. 2021, 17, 983–990, doi:10.3762/bjoc.17.80
- the regioisomers of potential monoterpenic 2-amino-1,3-diols [29][30][31][32][33]. These trifunctionalized terpenoids may also possess diverse biological activities and could successfully applied as chiral catalysts in enantioselective transformations [34]. In the present study, our aim was to
Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)
Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132
- study. Sesterterpenes are a rare terpene class, accounting for less than 2% of all known terpenoids, with only a few reports on their biosynthesis [72][73][74][75][76]. However, their frequent occurrence in marine organisms is striking and sponges are considered as the prime source of these terpenoids
- for a wide chemodiversity of terpenoid natural products [14][81]. Besides, the marine fungi Penicillium spp. and Aspergillus spp. are often associated with sponge hosts and were found to produce various terpenoids as well [15][82][83]. Hence, if sponges are not the origin of these metabolites, it is
Understanding the role of active site residues in CotB2 catalysis using a cluster model
Beilstein J. Org. Chem. 2020, 16, 50–59, doi:10.3762/bjoc.16.7
- comprise the largest and structurally most diverse family of natural products, currently representing over 80,000 reported structures from all kingdoms of life [3]. The largest diversity of terpenoids is reported for the plant kingdom where higher terpenes represent secondary metabolic products, which are
Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering
Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283
- Abstract Terpenoids are the largest and structurally most diverse class of natural products. They possess potent and specific biological activity in multiple assays and against diseases, including cancer and malaria as notable examples. Although the number of characterized terpenoid molecules is huge, our
- knowledge of how they are biosynthesized is limited, particularly when compared to the well-studied thiotemplate assembly lines. Bacteria have only recently been recognized as having the genetic potential to biosynthesize a large number of complex terpenoids, but our current ability to associate genetic
- functional promiscuity of terpene biosynthetic pathways renders terpene biosynthesis susceptible to rational pathway engineering using the latest developments in the field of synthetic biology. These engineered pathways will not only facilitate the rational creation of both known and novel terpenoids, their
Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum
Beilstein J. Org. Chem. 2019, 15, 2872–2880, doi:10.3762/bjoc.15.281
- investigated Physarum polycephalum, a plasmodial slime mold also known as acellular amoeba. Plasmodia of P. polycephalum grown on agar plates were found to release a mixture of volatile terpenoids consisting of four major sesquiterpenes (α-muurolene, (E)-β-caryophyllene, two unidentified sesquiterpenoids) and
- relatedness to bacterial TPSs. The biological role of the volatile terpenoids produced by the plasmodia of P. polycephalum is discussed. Keywords: amoebae; evolution; terpene synthases; volatiles; Introduction Volatile organic compounds (VOCs) are used by many living organisms as chemical languages for
- diverse VOCs, terpenoids are the largest group. Terpenoids are biosynthesized from two C5 diphosphate compounds isopentenyl diphosphate (IPP) and its isomer dimethylallyl diphosphate (DMAPP), which are produced by either the mevalonate (MVA) pathway or the methylerythritol phosphate (MEP) pathway [9][10
Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256
- : Aspergillus; biosynthesis; drimane; secondary metabolites; sesquiterpenoid; terpenes; Introduction The fungal genus Aspergillus is well recognised as a source of structurally diverse terpenoids comprising monoterpenoids [1], sesquiterpenoids [2][3][4][5], diterpenoids [6], sesterterpenoids [7][8][9
- production of terpenoids as the dominant biosynthetic class of secondary metabolites. Results and Discussion Purification and identification The metabolite profile of A. nanangensis was examined on a limited range of solid and liquid media suitable for fungal metabolite production. The metabolite profile
- column bed (55 × 250 mm). The column was eluted with CHCl3 (500 mL) containing increasing concentrations of MeOH. The fractions containing terpenoids (0-2% MeOH, 3.0 g) were pooled and fractionated using isocratic preparative HPLC (Zorbax C18, 65% MeCN/H2O, 60 mL min–1) to give five fractions containing
Synthetic terpenoids in the world of fragrances: Iso E Super® is the showcase
Beilstein J. Org. Chem. 2019, 15, 2590–2602, doi:10.3762/bjoc.15.252
- and terpenoids. For thousands of years mankind mainly used plant extracts to collect ingredients for the creation of perfumes. Many of these extracts contain complex mixtures of terpenes, that show distinct olfactoric properties as pure compounds. When organic synthesis appeared on the scene, the
- : asymmetric synthesis; fragrances; odorants; sandalwood; scents; terpenes; terpenoids; Review “Iso E Super® is to perfume what Tango Nuevo is to Tango Argentino” [1] Introduction – classical terpenes in perfumes Perfumes (Latin “per fumus”, which means “through smoke”) have accompanied mankind for thousands
- ]. Following this invention, many derivatives were produced to find new viable targets. These studies mostly focused on Diels–Alder cycloadditions to create structures that resemble terpenoids readily available from easily accessible and affordable starting materials like myrcene (1). One of the newly found
Current understanding and biotechnological application of the bacterial diterpene synthase CotB2
Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228
- ]. Yet another approach is the use of heteroatom-modified farnesyl diphosphates that could be still cyclized by TPSs yielding unnatural terpenoids [105]. CotB1 synthesizes geranylgeranyl diphosphate (GGDP) 3 from the substrates dimethylallyl diphosphate (DMAPP) 1 and isopentenyl diphosphate (IPP) 2. The
Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups
Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218
- hydrocarbons, substituted cyclic molecules, terpenoids, and steroid derivatives, were selectively fluorinated at some otherwise inaccessible sites, however, in low to moderate yields. On the other hand, the same group [83] developed Mn(salen)Cl as a catalyst for the direct C–H fluorination at benzylic
Isolation of fungi using the diffusion chamber device FIND technology
Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216
- of them being the marine-adapted fungal strain Heydenia cf. alpina. The latter produced two new terpenoids, which are the first secondary metabolites from this genus. Keywords: FIND; fungal one-step isolation device; Heydenia cf. alpina; natural products; terpenes; Introduction Natural products
Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids
Beilstein J. Org. Chem. 2019, 15, 2184–2190, doi:10.3762/bjoc.15.215
- synthesised in amorphadiene synthase-catalysed reactions from 8- and 12-methoxyfarnesyl diphosphates due to the highly plastic yet tightly controlled carbocationic chemistry of this sesquiterpene cyclase. Keywords: artemisinin; amorphadiene synthase; oxygenated terpenoids; sesquiterpenoids; substrate
- and functional groups to generate unnatural sesquiterpenoids that are not easily accessible by conventional organic synthesis [10][11][12][13][14][15][16][17][18][19]. Creating novel sesquiterpenoids, not normally found in nature, is of great interest due to the important applications of terpenoids in
Genome mining in Trichoderma viride J1-030: discovery and identification of novel sesquiterpene synthase and its products
Beilstein J. Org. Chem. 2019, 15, 2052–2058, doi:10.3762/bjoc.15.202
- synthases in Trichoderma viride have been seldom studied, despite the efficiency of filamentous fungi for terpenoid production. Using the farnesyl diphosphate-overexpressing Saccharomyces cerevisiae platform to produce diverse terpenoids, we herein identified an unknown sesquiterpene synthase from T. viride
- . viride to date. Keywords: genome mining; metabolic engineering; natural products; sesquiterpene synthase; terpenes; Trichoderma viride J1-030; Introduction Terpenoids represent the most diverse group of natural products, with a wide distribution in microorganisms, plants, insects and various marine
- invertebrates [1][2]. More than 80,000 terpenoids have been identified and characterised [3][4][5]. These diverse and complex natural products are mostly derived from carbocation cyclisation with linear C5 isoprene precursors, which are catalysed by terpene synthases (TPSs) [6]. TPSs can be classified into
Phylogenomic analyses and distribution of terpene synthases among Streptomyces
Beilstein J. Org. Chem. 2019, 15, 1181–1193, doi:10.3762/bjoc.15.115
- remarkable genetic potential to produce a large variety of secondary metabolites with different functions including antibiotics, antifungals, pigments or immunosuppressants [1][2][3]. These are compounds of diverse chemical nature such as polyketides, peptides, aminoglycosides or terpenoids [4][5
- ]. Terpenoids are the largest and the most diverse class of natural compounds known to date and include the initial products of terpene synthases and all derivatives made from them in tailoring steps. This very diverse class of organic compounds is best known as plant metabolites. However, recent studies
- revealed that terpenoids can be produced by all kingdoms of life including bacteria, fungi and protists [6][7][8][9][10]. The ability of an organism to produce terpenoids relies on whether the organism contains terpene synthase genes. Biosynthetically, the production of the different types of terpenes
New terpenoids from the fermentation broth of the edible mushroom Cyclocybe aegerita
Beilstein J. Org. Chem. 2019, 15, 1000–1007, doi:10.3762/bjoc.15.98
- secondary metabolite profiles of C. aegerita, we found several terpenoids in submerged cultures. Aside from the main metabolite, bovistol (1), two new bovistol derivatives B and C (2, 3) and pasteurestin C as a new protoilludane (4) were isolated by preparative HPLC. Their structures were elucidated by mass
- strains, targeting both volatile and non-volatile compounds. The present paper will describe the discovery of one known and three new non-volatile terpenoids (Figure 1) that were isolated from liquid cultures of C. aegerita and their physicochemical and preliminary biological characterisation. Results and
Iodine(III)-mediated halogenations of acyclic monoterpenoids
Beilstein J. Org. Chem. 2018, 14, 1103–1111, doi:10.3762/bjoc.14.96
- potential of the latter two vicinal difunctionalizations of terpenoids by not only expanding their substrate scope but also by trying to achieve other bromo-oxylations as well as analogous chloro- and/or iodofunctionalizations of linear terpenoids. For this purpose, five monoterpene derivatives – bearing
- Discussion Optimizations In order to carry out the exploration of the various halogenations that could be performed, geranyl acetate (1a) was chosen as the model substrate. In our study on terpenoids [16], the reaction conditions for the dibromination of the distal double bond were easily established from
- formation of allylic chloride 6. Conclusion Overall, we have further extended the scope of the iodine(III)-mediated oxidative halogenation of terpenoids which now includes dibromination, bromo(trifluoro)acetoxylation, bromohydroxylation, iodo(trifluoro)acetoxylation and allylic ene-chlorination. The
Herpetopanone, a diterpene from Herpetosiphon aurantiacus discovered by isotope labeling
Beilstein J. Org. Chem. 2017, 13, 2458–2465, doi:10.3762/bjoc.13.242
- resemblance to cadinane-type sesquiterpenes from plants, but is structurally entirely unprecedented in bacteria. Based on its molecular architecture, a possible biosynthetic pathway is postulated. Keywords: genome mining; herpetopanone; Herpetosiphon; isotope labeling; terpene; Introduction Terpenoids
- represent the largest group of natural products with about 60,000 different compounds being known. They occur in all three domains of life and are known to fulfill a variety of different functions, e.g., as membrane constituents, chemical attractants or feeding deterrents [1]. Over a long period, terpenoids
- were mainly reported from plants and, to a lesser degree, also from fungi and marine invertebrates. In recent years, however, the discovery of terpenoids from prokaryotes has gained momentum. The ease of DNA sequencing has strongly favored this development, contributing to the identification of
Biosynthetic origin of butyrolactol A, an antifungal polyketide produced by a marine-derived Streptomyces
Beilstein J. Org. Chem. 2017, 13, 441–450, doi:10.3762/bjoc.13.47
- diverse secondary metabolites with pharmaceutically useful bioactivities. Importantly, members of the genus Streptomyces have been the main source of drug discovery programs due to their high capacity in secondary metabolism including polyketides, peptides, terpenoids, alkaloids, and amino acid
A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus
Beilstein J. Org. Chem. 2016, 12, 2317–2324, doi:10.3762/bjoc.12.225
- complexity is reached within the largest, the terpenoids. An estimated number of 75,000 different compounds are known from all kinds of organisms including plants [1], bacteria [2][3][4][5], fungi [6] and, as recently shown, even social amoebae [7]. These molecules are all made from only a handful of linear
- representing various stereoisomers and constitutional isomers with different positioning of olefinic double bonds or alcohol functions are known just for sesquiterpenes [11]. The structural diversity of terpenoids can be further increased by the action of tailoring enzymes such as cytochrome P450
The direct oxidative diene cyclization and related reactions in natural product synthesis
Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200
- , polyketides, amino acids, fatty acids as well as acetogenins and terpenoids) are summarized in this review article. Putative structures of geraniol 1a (R = H) or 1b (R = H) (in 1924), their expected dihydroxylation products 2a or 2b and the true structure 3 as determined by Klein and Rojahn in 1965 [8
Mechanistic investigations on six bacterial terpene cyclases
Beilstein J. Org. Chem. 2016, 12, 1839–1850, doi:10.3762/bjoc.12.173
- much later, with the first described compounds being geosmin [3] and 2-methylisoborneol [4], two irregular terpenoids that represent a degraded sesquiterpene [5] and a methylated monoterpene [6], respectively. These compounds have a musty or earthy aroma and are responsible for the smell of freshly
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