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1.
J Agric Food Chem ; 71(1): 721-728, 2023 Jan 11.
Artigo em Inglês | MEDLINE | ID: mdl-36592095

RESUMO

In order to analyze the molecular rearrangement of terpenes in wine during aging, the changes in linalool, α-terpineol, nerol, and geraniol in model wine were investigated in the dark at low temperature for 90 days. Headspace-gas chromatograph-mass spectrometer/olfactometry was used for qualitative and relative quantitation of terpenes. Quantum mechanical calculation was used to analyze the Gibbs free energy. The results showed that nerol was converted into d-limonene, terpinolene, linalool, and α-terpineol. Geraniol was converted into ß-ocimene, terpinolene, and linalool. Linalool was converted into terpinolene. The conversion rate of nerol to terpinolene was the highest with 5.94%. α-Terpineol was not converted spontaneously into other terpenes due to its lowest Gibbs free energy, indicating that the cyclization and isomerization could occur spontaneously through an exotherm reaction. However, the dehydroxylation of linalool, nerol, and geraniol required an energy source.


Assuntos
Vitis , Vinho , Terpenos , Vinho/análise , Vitis/genética , Monoterpenos
2.
Int J Mol Sci ; 24(1)2023 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-36614303

RESUMO

Melanoma is deadly, physically impairing, and has ongoing treatment deficiencies. Current treatment regimens include surgery, targeted kinase inhibitors, immunotherapy, and combined approaches. Each of these treatments face pitfalls, with diminutive five-year survival in patients with advanced metastatic invasion of lymph and secondary organ tissues. Polyphenolic compounds, including cannabinoids, terpenoids, and flavonoids; both natural and synthetic, have emerging evidence of nutraceutical, cosmetic and pharmacological potential, including specific anti-cancer, anti-inflammatory, and palliative utility. Cannabis sativa is a wellspring of medicinal compounds whose direct and adjunctive application may offer considerable relief for melanoma suffers worldwide. This review aims to address the diverse applications of C. sativa's biocompounds in the scope of melanoma and suggest it as a strong candidate for ongoing pharmacological evaluation.


Assuntos
Canabinoides , Cannabis , Melanoma , Humanos , Cannabis/química , Canabinoides/farmacologia , Canabinoides/uso terapêutico , Canabinoides/química , Terpenos/farmacologia , Melanoma/tratamento farmacológico , Compostos Fitoquímicos/farmacologia , Compostos Fitoquímicos/uso terapêutico
3.
Molecules ; 28(2)2023 Jan 13.
Artigo em Inglês | MEDLINE | ID: mdl-36677891

RESUMO

Interest in cultivating cannabis for medical and recreational purposes is increasing due to a dramatic shift in cannabis legislation worldwide. Therefore, a comprehensive understanding of the composition of secondary metabolites, cannabinoids, and terpenes grown in different environmental conditions is of primary importance for the medical and recreational use of cannabis. We compared the terpene and cannabinoid profiles using gas/liquid chromatography and mass spectrometry for commercial cannabis from genetically identical plants grown indoors using artificial light and artificially grown media or outdoors grown in living soil and natural sunlight. By analyzing the cannabinoids, we found significant variations in the metabolomic profile of cannabis for the different environments. Overall, for both cultivars, there were significantly greater oxidized and degraded cannabinoids in the indoor-grown samples. Moreover, the outdoor-grown samples had significantly more unusual cannabinoids, such as C4- and C6-THCA. There were also significant differences in the terpene profiles between indoor- and outdoor-grown cannabis. The outdoor samples had a greater preponderance of sesquiterpenes including ß-caryophyllene, α-humulene, α-bergamotene, α-guaiene, and germacrene B relative to the indoor samples.


Assuntos
Canabinoides , Cannabis , Alucinógenos , Canabinoides/análise , Cannabis/química , Terpenos/análise , Cromatografia Gasosa-Espectrometria de Massas/métodos , Alucinógenos/análise , Agonistas de Receptores de Canabinoides/metabolismo
4.
Food Res Int ; 163: 112290, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36596195

RESUMO

Ambelania duckei Markgr is a species of the Apocynaceae family, native to the Amazon region that is unexplored from a nutritional point of view and studied in relation to its chemical constituents. This work presents an unprecedented study of the proximate composition, lipid profile, a chromatographic analysis, and the antioxidant activity of extracts obtained from the pulp, peel and seeds of the fruit. The results showed that potassium, calcium, and magnesium stood out as the most abundant key minerals in the fruit peel and pulp, with an emphasis on the potassium present in the fruit pulp at 1750.0 mg/100 g. The peel had the highest content of total phenolics (374.86 mg/g), flavonoids (15.54 mg/g), tannins (27.45 mg/g) and O-diphenols (379.36 mg/g; 645.71 mg/g). The antioxidant activity (AA) was highest in the peel compared to the pulp in the DPPH, ABTS, and ORAC tests showing: IC50 of 29.82; 43.67; and 407.13 µg/mL, respectively but a lower activity for the Fe2+ chelator. The analysis of the lipid fractions from the peel, pulp, and seeds of the A. duckei fruit resulted in 14 types of fatty acids. The major fatty acids found in the three parts of the fruit were oleic acid (peel, 22.52 %), palmitic acid (pulp, 17.34 %), and linoleic acid (seeds, 47.99 %). The lipid profile and nutritional aspects had a PUFA/SFA ratio (0.4-1.8) in the different parts of the A. duckei fruit; the atherogenic and thrombogenic indexes were higher in the peel (1.23) and pulp (0.62), respectively. The ratio between the hypocholesterolemic and hypercholesterolemic fatty acids (0.5 - 3.8) calculated for the fruit are within the desirable range for a nutritious food. The chromatographic analysis of the volatile organic compounds (VOCs) from the peel and pulp of the fruit, identified 74 VOCs, of which 60.9 % are related to terpenes, and emit notes such as cucumber, green, fatty, floral, and mint, due to the presence of substances with OAVs > 10, especially α-ionone, 1,8-cineole, 2,4-decadienal, and dodecanal. The analysis of the MS and MS/MS spectra of the chromatograms obtained by LC- QTOF-HRMS led to the identification of 26 compounds in the peel, seeds and pulp of A. duckei, such as fatty acids, phenolic acid, flavonoids, proanthocyanidins, alkaloids, and terpenoids. The results show that the pulp of A. duckei has potential as nourishing food and the nutritional and chemical aspects of the peel can be applied to commercial applications.


Assuntos
Apocynaceae , Frutas , Frutas/química , Antioxidantes/análise , Espectrometria de Massas em Tandem , Flavonoides/análise , Ácidos Graxos/análise , Terpenos/análise , Potássio/análise
5.
Philos Trans R Soc Lond B Biol Sci ; 378(1871): 20220033, 2023 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-36633275

RESUMO

Terpenoids represent the largest structural family of natural products (NPs) and have various applications in the pharmaceutical, food and fragrance industries. Their diverse scaffolds are generated via a multi-step cyclization cascade of linear isoprene substrates catalysed by terpene synthases (TPSs). Bisabolene NPs, which are sesquiterpenes (C15), have wide applications in medicines and biofuels and serve as bioactive substances in ecology. Despite the discovery of some canonical class I TPSs that synthesize bisabolenes from plants, bacteria and insects, it remained unknown whether any bisabolene synthases from fungi could produce bisabolenes as a main product. Antrodia cinnamomea, a Basidiomycota fungus, is a medicinal mushroom indigenous to Taiwan and a known prolific producer of bioactive terpenoids, but little is known regarding the enzymes involved in the biosynthetic pathways. Here, we applied a genome mining approach against A. cinnamomea and discovered two non-canonical UbiA-type TPSs that both synthesize (+)-(S,Z)-α-bisabolene (1). It was determined that two tailoring enzymes, a P450 monooxygenase and a methyltransferase, install a C14-methyl ester on the bisabolene scaffold. In addition, four new bisabolene derivatives, 2 and 4-6, were characterized from heterologous reconstitution in Saccharomyces cerevisiae. Our study uncovered enzymatic tools to generate structurally diverse bisabolene NPs. This article is part of the theme issue 'Reactivity and mechanism in chemical and synthetic biology'.


Assuntos
Polyporales , Sesquiterpenos , Terpenos/metabolismo , Fungos , Polyporales/metabolismo , Saccharomyces cerevisiae/genética , Saccharomyces cerevisiae/metabolismo
6.
Philos Trans R Soc Lond B Biol Sci ; 378(1871): 20220037, 2023 Feb 27.
Artigo em Inglês | MEDLINE | ID: mdl-36633279

RESUMO

Fungal meroterpenoids are important bioactive natural products. Their biosynthetic machineries are highly diverse, and reconstitutions lead to the production of unnatural meroterpenoids. In this study, heterologous gene expression in Aspergillus oryzae and in vitro assays elucidated the biosynthetic pathway of the orthoester-containing fungal meroterpenoid austalide F. Remarkably, the α-ketoglutarate-dependent oxygenase AstB produces the hemiacetal intermediate, and the methyltransferase AstL transfers a methyl group on it to construct the orthoester functionality. This study presents the extraordinary orthoester biosynthetic machinery and provides valuable insights into the creation of unnatural novel bioactive meroterpenoids through engineered biosynthesis. This article is part of the theme issue 'Reactivity and mechanism in chemical and synthetic biology'.


Assuntos
Aspergillus oryzae , Vias Biossintéticas , Terpenos , Terpenos/metabolismo , Aspergillus oryzae/metabolismo , Genes Fúngicos , Regulação Fúngica da Expressão Gênica
7.
Food Microbiol ; 111: 104193, 2023 May.
Artigo em Inglês | MEDLINE | ID: mdl-36681397

RESUMO

Although the impact of nitrogen nutrition on the production of fermentative aromas in oenological fermentation is well known today, one may wonder whether the effects studied are the same when winemaking takes place at high turbidities, specifically for the production of wines intended for cognac distillation. To that effect, a fermentation robot was used to analyze 30 different fermentation conditions at two turbidity levels with several factors tested: (i) initial addition of nitrogen either organic (with a mixture of amino acids - MixAA) or inorganic with di-ammonium phosphate (DAP) at different concentrations, (ii) variation of the ratio of inorganic/organic nitrogen (MixAA and DAP) and (iii) addition of different single amino acids (alanine, arginine, aspartic acid and glutamic acid). A metabolomic analysis was carried out on all resulting wines to have a global vision of the impact of nitrogen on more than sixty aromatic molecules of various families. Then, at the end of the alcoholic fermentation, the wines were micro-distilled. A first interesting observation was that the aroma profiles of both wines and distillates were close, indicating that the concentration factor is rather similar for the different aromas studied. Secondly, the fermentation kinetics and aroma results have shown that the nitrogen concentration effect prevailed over the nature of nitrogen. Although the lipid concentration was in excess, an interaction between the assimilable nitrogen and lipid contents was still observed in wines or in micro-distillates. Alanine is involved in the synthesis of acetaldehyde, isobutanol, isoamyl alcohol and isoamyl acetate. Finally, it was demonstrated that modifying the ratio of assimilable nitrogen in musts is not an interesting technological response to improve the aromatic profile of wines and brandies. Indeed, unbalance the physiological ratio of the must by adding a single source of assimilable nitrogen (organic or inorganic) has been shown to deregulate the synthesis of most of the fermentation aromas produced by the yeast. Wine metabolomic analysis confirmed the results that had been observed in micro-distillates but also in the other aromatic families, especially on terpenes. The contribution of solid particles, but also yeast biosynthesis (via sterol management in must) to wine terpenes is discussed. Indeed, the synthesis of terpenes in this oenological context seems to be favored, especially since the concentration of assimilable nitrogen (in addition to the lipid content) favor their accumulation in the medium. A non-negligible vintage effect on the terpene profile was also demonstrated with variations in their distribution depending on the years. Thus, the present study focuses on the metabolism of wine yeasts under different environmental conditions (nitrogen and lipid content) and on the impact of distillation on the fate of flavor compounds. The results highlight once again the complexity of metabolic fluxes and of the impact of nitrogen source (nature and amount) and of lipids. Furthermore, this study demonstrates that beyond the varietal origin of terpenes, the part resulting from the de novo synthesis by the yeast during the fermentation cannot be neglected in the context of cognac winemaking with high levels of turbidity.


Assuntos
Vitis , Vinho , Humanos , Vinho/análise , Vitis/química , Saccharomyces cerevisiae/metabolismo , Nitrogênio/metabolismo , Odorantes/análise , Aminoácidos/metabolismo , Fermentação , Lipídeos , Terpenos/análise , Terpenos/metabolismo , Alanina/análise , Alanina/metabolismo
8.
ACS Chem Biol ; 18(1): 134-140, 2023 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-36594743

RESUMO

Milk cap mushrooms in the genus Lactarius are known to produce a wide variety of terpene natural products. However, their repertoire of terpene biosynthetic enzymes has not been fully explored. In this study, several candidate sesquiterpene synthases were identified from the genome of the saffron milk cap mushroom L. deliciosus and expressed in a sesquiterpene-overproducing Escherichia coli strain. In addition to enzymes that produce several known terpenes, we identified an enzyme belonging to a previously unknown clade of sesquiterpene synthases that produces a terpene with a unique spiro-tricyclic scaffold. These findings add to the rich diversity of terpene scaffolds and mushroom terpene synthases and are valuable for biotechnological applications in producing these terpenoids.


Assuntos
Agaricales , Alquil e Aril Transferases , Basidiomycota , Sesquiterpenos , Terpenos , Alquil e Aril Transferases/genética
9.
Mar Drugs ; 21(1)2023 Jan 12.
Artigo em Inglês | MEDLINE | ID: mdl-36662224

RESUMO

Halocynthia roretzi, the edible ascidian, has been demonstrated to be an important source of bioactive natural metabolites. Here, we reported a novel terpenoid compound named Halorotetin A that was isolated from tunic ethanol extract of H. roretzi by silica gel column chromatography, preparative layer chromatography (PLC), and semipreparative-HPLC. 1H and 13C NMRs, 1H-1H COSY, HSQC, HMBC, NOESY, and HRESIMS profiles revealed that Halorotetin A was a novel terpenoid compound with antitumor potentials. We therefore treated the culture cells with Halorotetin A and found that it significantly inhibited the proliferation of a series of tumor cells by exerting cytotoxicity, especially for the liver carcinoma cell line (HepG-2 cells). Further studies revealed that Halorotetin A affected the expression of several genes associated with the development of hepatocellular carcinoma (HCC), including oncogenes (c-myc and c-met) and HCC suppressor genes (TP53 and KEAP1). In addition, we compared the cytotoxicities of Halorotetin A and doxorubicin on HepG-2 cells. To our surprise, the cytotoxicities of Halorotetin A and doxorubicin on HepG-2 cells were similar at the same concentration and Halorotetin A did not significantly reduce the viability of the normal cells. Thus, our study identified a novel compound that significantly inhibited the proliferation of tumor cells, which provided the basis for the discovery of leading compounds for antitumor drugs.


Assuntos
Carcinoma Hepatocelular , Neoplasias Hepáticas , Urocordados , Animais , Humanos , Proteína 1 Associada a ECH Semelhante a Kelch , Urocordados/química , Terpenos/farmacologia , Fator 2 Relacionado a NF-E2 , Proliferação de Células
10.
Nat Commun ; 14(1): 343, 2023 Jan 20.
Artigo em Inglês | MEDLINE | ID: mdl-36670101

RESUMO

The spatial organization of genes within plant genomes can drive evolution of specialized metabolic pathways. Terpenoids are important specialized metabolites in plants with diverse adaptive functions that enable environmental interactions. Here, we report the genome assemblies of Prunella vulgaris, Plectranthus barbatus, and Leonotis leonurus. We investigate the origin and subsequent evolution of a diterpenoid biosynthetic gene cluster (BGC) together with other seven species within the Lamiaceae (mint) family. Based on core genes found in the BGCs of all species examined across the Lamiaceae, we predict a simplified version of this cluster evolved in an early Lamiaceae ancestor. The current composition of the extant BGCs highlights the dynamic nature of its evolution. We elucidate the terpene backbones generated by the Callicarpa americana BGC enzymes, including miltiradiene and the terpene (+)-kaurene, and show oxidization activities of BGC cytochrome P450s. Our work reveals the fluid nature of BGC assembly and the importance of genome structure in contributing to the origin of metabolites.


Assuntos
Diterpenos , Lamiaceae , Lamiaceae/genética , Lamiaceae/metabolismo , Diterpenos/metabolismo , Terpenos/metabolismo , Família Multigênica , Vias Biossintéticas/genética
11.
Water Res ; 229: 119486, 2023 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-36535088

RESUMO

Wastewater (WW) treatment in anaerobic membrane bioreactors (AnMBR) is considered more sustainable than in aerobic reactors. However, outputs from AnMBR are a mixed methane and carbon dioxide gas stream as well as ammonium- (N) and phosphate- (P) containing waters. Using AnMBR outputs as inputs for photoautotrophic algal cultivation can strip the CO2 while removing N and P from effluent which feed algal biomass generation. Recent advances in algal engineering have generated strains that produce high-value side products concomitant with biomass, although only shown in heavily domesticated, lab-adapted strains. Here, it was investigated whether engineered Chlamydomonas reinhardtii could be grown directly in AnMBR effluent with CO2 concentrations found in AnMBR off-gas. The strain was found to proliferate over bacteria in the non-sterile effluent, consume N and P to levels that meet general discharge or reuse limits, and tolerate cultivation in modelled (extreme) outdoor environmental conditions prevalent along the central Red Sea coast. In addition to ∼2.4 g CDW L-1 biomass production in 96 h, a high-value heterologous sesquiterpene co-product could be obtained from 'milking' up to 837 µg L-1 culture in 96 h. This is the first demonstration of a combined bio-process that employs a heavily engineered algal strain to enhance the product generation potentials from AnMBR effluent treatment. This study shows it is possible to convert waste into value through use of engineered algae while also improving wastewater treatment economics through co-product generation.


Assuntos
Microalgas , Anaerobiose , Dióxido de Carbono , Biomassa , Terpenos , Reatores Biológicos/microbiologia , Metano , Eliminação de Resíduos Líquidos
12.
Phytochemistry ; 206: 113548, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36481317

RESUMO

Antiosteoclastogenic-guided screening was conducted with 120 extracts of the medicinal plants collected in Egypt that led to the selection of Artemisia judaica L. (Asteraceae). Three undescribed davanone-related terpenoids, arteperoxides A-C, were isolated from the extract with two known derivatives, hydroxydavanone and davana acid. Structural analysis revealed that arteperoxides A-C were tris-normonoterpene-sesquiterpene conjugates with peroxide bridges. Although davanone derivatives with peroxides, such as a hydroperoxyl and peroxyhemiketal groups, have been isolated from Artemisia species, arteperoxides A-C are the first variations observed to contain peroxide bridges between two terpene-derived units. The absolute configurations of arteperoxides A and B were studied based on their spectroscopic data compared with those of the semisynthetic analogs that have ether linkages. The natural and synthetic compounds were tested for the antiosteoclastogenic activity, and arteperoxide C and hydroxydavanone were more potent than other compounds at 20 µM.


Assuntos
Artemisia , Plantas Medicinais , Sesquiterpenos , Artemisia/química , Peróxidos , Sesquiterpenos/farmacologia , Sesquiterpenos/química , Terpenos , Extratos Vegetais/farmacologia , Extratos Vegetais/química
13.
J Ethnopharmacol ; 303: 115989, 2023 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-36509259

RESUMO

ETHNOPHARMACOLOGICAL RELEVANCE: The Aconitum genus plants as a natural pesticide for insecticide and rodent control has been recorded in Chinese folk. However, the insecticide effect, mechanism, and active composition of Aconitum polycarpum Chang ex W.T.Wang have not been studied further. AIM OF THE STUDY: This study was designed to analyze the chemical composition, evaluate contact toxicity of petroleum ether extracts (PEEs) and essential oils (EOs) of A. polycarpum, and further explore their possible insecticidal mechanism. MATERIALS AND METHODS: The roots of A. polycarpum were extracted with 90% methanol, and then extracted with petroleum ether to obtain PEEs; the EOs was extracted by distillation. The chemical compositions of PEEs and EOs were analyzed by GC-MS. Contact toxicity was evaluated by the immersion method. Exploring insecticidal mechanisms through in vitro enzyme inhibitory activity. RESULTS: 12 compounds were identified from PEEs by GC-MS, mainly including aliphatic (94.8%), the main compositions were Octadecadienol (ODO) (aliphatic, 53.2%) and L-Ascorbyl dipalmitate (LADP) (aliphatic, 36.1%). 24 compounds were identified in EOs. About 44.6% of the identified components were terpenoids and their derivatives, and the rest were mainly aliphatic (34.7%) and phenols (3.0%). The main chemical components were L (-)-Borneol (LB) (terpenoid, 28.3%), LADP (aliphatic, 19.1%), and Isoborneol (terpenoid, 9.1%). The contact toxicity indicated that the PEEs showed great contact toxicity against Spodoptera exigua (LC50 = 126.2 mg/L). Meanwhile, LADP (LC50 = 128.1 mg/L) and ODO (LC50 = 121.3 mg/L) was similar to that of Cyhalothrin (LC50 = 124.2 mg/L) in contact toxicity. In addition, we found that LADP and ODO exhibited excellent inhibitory activity against CarE (IC50 = 58.0, 56.1 mg/L, respectively) by measuring in vitro enzyme inhibitory activity, which was superior than Cyhalothrin (IC50 = 68.1 mg/L). CONCLUSIONS: The chemical compositions and contact toxicity of EOs and PEEs of A. polycarpum were analyzed and evaluated, and their insecticidal mechanisms were preliminarily discussed for the first time. It proved PEEs of A. polycarpum and its main components (LADP and ODO) exhibited excellent contact toxicity against S. exigua, and CarE was identified as a potential target for contact toxicity. This study indicated that the insecticidal activity of petroleum ether extracts from A. polycarpum is quite promising, and provides a practical and scientific basis for the development and application of botanical pesticides.


Assuntos
Aconitum , Inseticidas , Óleos Voláteis , Inseticidas/farmacologia , Óleos Voláteis/toxicidade , Óleos Voláteis/química , Terpenos
14.
Fitoterapia ; 164: 105390, 2023 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-36513292

RESUMO

Four novel epimeric meroterpenoids, ganadone A (1), 3',10'-di-epi-ganadone A (2), 10'-epi-ganadone A (3), and 3'-epi-ganadone A (4) as well as another pairs of epimers, ganadone B (5) and 10'-epi-ganadone B (6), with a same basic skeleton compound ganadone C (7), together with two lactonized meroterpenoids, ganadones D and E (8 and 9) were isolated from the fruiting bodies of Ganoderma cochlear. Compounds 1-7 were constructed with fascinating adjacent 6',7'-bifuran ring system. Fortunately, we have revised our previously reported structure cochlearol Q, which was proposed pyrano[6',7'-b]pyran ring system into 6',7'-bifuran motif. All the isolates were characterized by analysis of HRESIMS, NMR spectroscopy and 1 was supported by X-ray crystallography analysis. The absolute stereochemistry of 1-9 were assigned by quantum chemical calculations. Biological evaluation of 1-9 showed that 5, 6, and 9 have significant anti-inflammatory potentials.


Assuntos
Ganoderma , Terpenos , Terpenos/química , Estrutura Molecular , Ciclo-Oxigenase 2 , Carpóforos/química , Ganoderma/química
15.
Proc Natl Acad Sci U S A ; 120(1): e2207680120, 2023 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-36577077

RESUMO

Engineering microbes for the production of valuable natural products is often hindered by the regulation of native competing metabolic networks in host. This is particularly evident in the case of terpenoid synthesis in yeast, where the canonical terpenoid precursors are tightly coupled to the biosynthesis of sterols essential for yeast viability. One way to circumvent this limitation is by engineering product pathways less connected to the host native metabolism. Here, we introduce a two-step isopentenol utilization pathway (IUP) in Saccharomyces cerevisiae to augment the native mevalonate pathway by providing a shortcut to the synthesis of the common terpenoid precursors, isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP). As such, the IUP was capable of elevating the IPP/DMAPP pool by 147-fold compared with the native pathway. We further demonstrate that cofeeding isoprenol and prenol enhances geranyl diphosphate (GPP) content for monoterpene biosynthesis. More importantly, we established a synthetic three-step route for efficient synthesis of di-and tetraterpene precursor geranylgeranyl diphosphate (GGPP), circumventing the competition with farnesyl diphosphate (FPP) for sterol biosynthesis and elevating the GGPP level by 374-fold. We combine these IUP-supported precursor-forming platforms with downstream terpene synthases to harness their potential and improve the production of industrially relevant terpenoids by several fold. Our exploration provides a universal and effective platform for supporting terpenoid synthesis in yeast.


Assuntos
Saccharomyces cerevisiae , Terpenos , Saccharomyces cerevisiae/genética , Saccharomyces cerevisiae/metabolismo , Terpenos/metabolismo , Engenharia Metabólica
16.
Talanta ; 254: 124182, 2023 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-36527912

RESUMO

Isoprenoids give rise to many functional products used today such as flavours, fragrances and even pharmaceutical compounds. Mevalonate pathway metabolites are the key intermediates that affect the production yield of isoprenoids. With increasing demand and benefit of isoprenoids, the present study adopts Analytical Quality-by-Design (AQbD) approach to establish an efficacious extraction protocol prior to the determination of mevalonate pathway metabolites in an engineered Escherichia coli model. The statistical experimental design approach, described in this work, has successfully validated an optimised sample preparation method i.e., using acetonitrile: 50 mM ammonium formate (pH 9.5) (7:3) (ACN73) at -20 °C for 10 min without solvent evaporation to retain the targeted mevalonate metabolites in engineered E. coli strain. The study also demonstrates the use of liquid chromatography paired with a Time-of-Flight Mass Spectrometer (LC-ToF-MS) for the quantitative analysis of the mevalonate pathway metabolites in E. coli. The analytical method was validated in accordance with guidelines in Metabolomics Standards Initiative and ICH Q2 (R1) with analyte spike recoveries at 80% and above. In short, the present study overcomes the one-variable-at-a-time (OVAT) limitations in analytical development, minimises metabolite losses and gives better cost and time efficiencies by eliminating the solvent evaporation and swapping process. This work highlights the importance of analytical methods development in microbial metabolomics studies.


Assuntos
Escherichia coli , Ácido Mevalônico , Escherichia coli/metabolismo , Ácido Mevalônico/metabolismo , Projetos de Pesquisa , Cromatografia Líquida/métodos , Terpenos , Solventes
17.
Artigo em Inglês | MEDLINE | ID: mdl-36481725

RESUMO

Ultra-performance liquid chromatography coupled with time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) combined with multivariate statistical analysis was applied to the study of plant metabolomics to reveal the factors affecting the content of ginkgo leaf compounds. As a follow-up analysis, the terpene lactones and ginkgolic acids were quantified simultaneously using ultra-performance liquid chromatography coupled with triple quadrupole mass spectrometry (UPLC-QqQ-MS/MS), and subsequently total flavonol glycosides were quantified by high-performance liquid chromatography (HPLC). The results revealed that a total of 52 compounds were potentially identified by establishing a database, and 10 compounds were verified by reference standards; terpene lactones, ginkgolic acids, and flavonoids were the differential compounds; and ginkgolide A was identified as an important indicator compound for tree age. In addition, quantitative analysis showed that the contents of total flavonol glycosides and terpene lactones were highest during April and August in young ginkgo leaves, and differed based on origin. In summary, numerous compounds were rapidly detected by liquid chromatography coupled with MS, the ginkgo leaf samples were compared, and the differential metabolites were screened out. The content changing rules of the target compounds in ginkgo leaves from different regions with different tree ages and harvesting periods were clarified.


Assuntos
Ginkgo biloba , Espectrometria de Massas em Tandem , Espectrometria de Massas em Tandem/métodos , Folhas de Planta/química , Flavonóis/análise , Glicosídeos/análise , Cromatografia Líquida de Alta Pressão/métodos , Terpenos/análise , Lactonas/química , Extratos Vegetais/química
18.
Curr Opin Microbiol ; 71: 102255, 2023 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-36563485

RESUMO

The apicoplast of Plasmodium falciparum is the only source of essential isoprenoid precursors and Coenzyme A (CoA) in the parasite. Isoprenoid precursor synthesis relies on the iron-sulfur cluster (FeS) cofactors produced within the apicoplast, rendering FeS synthesis an essential function of this organelle. Recent reports provide important insights into the roles of FeS cofactors and the use of isoprenoid precursors and CoA both inside and outside the apicoplast. Here, we review the recent insights into the roles of these metabolites in blood-stage malaria parasites and discuss new questions that have been raised in light of these discoveries.


Assuntos
Apicoplastos , Malária , Parasitos , Animais , Humanos , Apicoplastos/metabolismo , Malária/parasitologia , Plasmodium falciparum/genética , Plasmodium falciparum/metabolismo , Terpenos/metabolismo , Proteínas de Protozoários/metabolismo
19.
Zhongguo Zhong Yao Za Zhi ; 47(21): 5849-5854, 2022 Nov.
Artigo em Chinês | MEDLINE | ID: mdl-36472003

RESUMO

Eight terpenoids were isolated from the fruits of Amomum villosum by silica gel, Sephadex LH-20, Rp-C_(18), MCI GEL CHP20 P column chromatography, preparative TLC, and HPLC. Their structures were identified by HR-ESI-MS, ~1H and ~(13)C-NMR, IR, UV, [α]_D, and ECD spectroscopic data as kravanhin A 3-O-ß-D-glucopyranoside(1), kravanhin B(2), 6-eudesmene-1ß,4ß-diol(3), oplodiol(4), vicodiol(5),(1R,2S,4R,7S)-vicodiol 9-O-ß-D-glucopyranoside(6),(1R,2S,4S,5R)-angelicoidenol 2-O-ß-D-glucopyranoside(7), and(1S,2S,4R,6S)-bornane-2,6-diol 2-O-ß-D-glucopyranoside(8). Compound 1 was a new compound, and compounds 2-5 were isolated from A. villosum for the first time. Their hypoglycemic activity was tested based on STC-1 cell model and two enzymatic models(GPa and PTP1 B). The results showed that compounds 1, 7, and 8 could stimulate GLP-1 with the secretion rates of 692.8%, 398.6%, and 483.3% at 25.0 µmol·L~(-1), and compound 6 showed inhibitory activity against GPa with an IC_(50) value of 78.6 µmol·L~(-1).


Assuntos
Amomum , Frutas , Frutas/química , Terpenos/análise , Hipoglicemiantes/farmacologia , Hipoglicemiantes/análise , Cromatografia Líquida de Alta Pressão
20.
Curr Microbiol ; 80(1): 17, 2022 Dec 02.
Artigo em Inglês | MEDLINE | ID: mdl-36460935

RESUMO

Due to the great threat of chemical pesticides to the ecosystem environment, it is a long-term goal to find environmentally friendly green pesticides. Essential oils (EOs) are considered weapons in plant chemical defense and are important sources of green pesticides. Therefore, the antifungal effects and action mechanisms of Cymbopogom citratus (C. citratus) EOs against seven kinds of Panax notoginseng (P. notoginseng) pathogenic fungi were investigated. Oxford Cup results showed that C. citratus EOs had an excellent detraction effects against seven fungi of P. notoginseng. Gas chromatography-mass spectrometry (GC-MS) was used to construct the chemical profiles of C. citratus EOs, disclosed that the main categories are terpenes and oxygenated terpenes. In addition, compared with the hymexazol, the minimum inhibitory concentration (MIC) showed that EOs and their main components had strong antifungal activities. Besides, EOs had a synergistic effect with hymexazol (a chemical pesticide). The antifungal mechanism of C. citratus EOs was studied by using Fusarium oxysporum (F. oxysporum) as the dominant pathogen. C. citratus EOs may affect the metabolism of fungi and induce mycotoxins to destroy the cell wall to achieve antifungal effects. Finally, EOs were found to significantly retard P. notoginseng infection by F. oxysporum. According to our research, C. citratus EOs are potential green antifungal agent that can be used in the cultivation of P. notoginseng.


Assuntos
Óleos Voláteis , Panax notoginseng , Praguicidas , Antifúngicos/farmacologia , Óleos Voláteis/farmacologia , Ecossistema , Fungos , Terpenos
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