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1.
Nat Plants ; 7(10): 1330-1334, 2021 10.
Artigo em Inglês | MEDLINE | ID: mdl-34650264

RESUMO

Analysis of over 100 Cannabis samples quantified for terpene and cannabinoid content and genotyped for over 100,000 single nucleotide polymorphisms indicated that Sativa- and Indica-labelled samples were genetically indistinct on a genome-wide scale. Instead, we found that Cannabis labelling was associated with variation in a small number of terpenes whose concentrations are controlled by genetic variation at tandem arrays of terpene synthase genes.


Assuntos
Alquil e Aril Transferases/genética , Canabinoides/metabolismo , Cannabis/genética , Proteínas de Plantas/genética , Polimorfismo de Nucleotídeo Único , Terpenos/metabolismo , Alquil e Aril Transferases/metabolismo , Cannabis/enzimologia , Cromatografia Gasosa-Espectrometria de Massas , Genótipo , Proteínas de Plantas/metabolismo
2.
Nat Plants ; 7(9): 1239-1253, 2021 09.
Artigo em Inglês | MEDLINE | ID: mdl-34475528

RESUMO

Aristolochia, a genus in the magnoliid order Piperales, has been famous for centuries for its highly specialized flowers and wide medicinal applications. Here, we present a new, high-quality genome sequence of Aristolochia fimbriata, a species that, similar to Amborella trichopoda, lacks further whole-genome duplications since the origin of extant angiosperms. As such, the A. fimbriata genome is an excellent reference for inferences of angiosperm genome evolution, enabling detection of two novel whole-genome duplications in Piperales and dating of previously reported whole-genome duplications in other magnoliids. Genomic comparisons between A. fimbriata and other angiosperms facilitated the identification of ancient genomic rearrangements suggesting the placement of magnoliids as sister to monocots, whereas phylogenetic inferences based on sequence data we compiled yielded ambiguous relationships. By identifying associated homologues and investigating their evolutionary histories and expression patterns, we revealed highly conserved floral developmental genes and their distinct downstream regulatory network that may contribute to the complex flower morphology in A. fimbriata. Finally, we elucidated the genetic basis underlying the biosynthesis of terpenoids and aristolochic acids in A. fimbriata.


Assuntos
Aristolochia/crescimento & desenvolvimento , Aristolochia/genética , Ácidos Aristolóquicos/biossíntese , Evolução Biológica , Flores/crescimento & desenvolvimento , Flores/genética , Magnoliopsida/genética , Terpenos/metabolismo , Ácidos Aristolóquicos/genética , Variação Genética , Genoma de Planta , Genótipo , Filogenia , Plantas Medicinais/genética , Plantas Medicinais/crescimento & desenvolvimento
3.
Mol Genet Genomics ; 296(6): 1177-1202, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34557965

RESUMO

Medicinal plants of the North-Western Himalayan region are known for their unprecedented biodiversity and valuable secondary metabolites that are unique to this dynamic geo-climatic region. From ancient times these medicinal herbs have been used traditionally for their therapeutic potentials. But from the last 2 decades increasing pharmaceutical demand, illegal and unorganized trade of these medicinal plants have accelerated the rate of over-exploitation in a non-scientific manner. In addition, climate change and anthropogenic activities also affected their natural habitat and driving most of these endemic plant species to critically endangered that foresee peril of mass extinction from this eco-region. Hence there is an urgent need for developing alternative sustainable approaches and policies to utilize this natural bioresource ensuring simultaneous conservation. Hither, arise the advent of sequencing-based transcriptomic studies significantly contributes to better understand the background of important metabolic pathways and related genes/enzymes of high-value medicinal herbs, in the absence of genomic information. The use of comparative transcriptomics in conjunction with biochemical techniques in North-Western Himalayan medicinal plants has resulted in significant advances in the identification of the molecular players involved in the production of secondary metabolic pathways over the last decade. This information could be used to further engineer metabolic pathways and breeding programs, ultimately leading to the development of in vitro systems dedicated to the production of pharmaceutically important secondary metabolites at the industrial level. Collectively, successful adoption of these approaches can certainly ensure the sustainable utilization of Himalayan bioresource by reducing the pressure on the wild population of these critically endangered medicinal herbs. This review provides novel insight as a transcriptome-based bioresource repository for the understanding of important secondary metabolic pathways genes/enzymes and metabolism of endangered high-value North-Western Himalayan medicinal herbs, so that researchers across the globe can effectively utilize this information for devising effective strategies for the production of pharmaceutically important compounds and their scale-up for sustainable usage and take a step forward in omics-based conservation genetics.


Assuntos
Plantas Medicinais/genética , Plantas Medicinais/metabolismo , Metabolismo Secundário/fisiologia , Transcriptoma/genética , Alcaloides/metabolismo , Ásia Ocidental , Metabolismo Energético/genética , Extinção Biológica , Engenharia Genética , Melhoramento Vegetal , Propanóis/metabolismo , Terpenos/metabolismo
4.
Molecules ; 26(15)2021 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-34361835

RESUMO

The present study compared the effects of natural senescence and methyl jasmonate (JA-Me) treatment on the levels of terpene trilactones (TTLs; ginkgolides and bilobalide), phenolic acids, and flavonoids in the primary organs of Ginkgo biloba leaves, leaf blades, and petioles. Levels of the major TTLs, ginkgolides B and C, were significantly higher in the leaf blades of naturally senesced yellow leaves harvested on 20 October compared with green leaves harvested on 9 September. In petioles, a similar effect was found, although the levels of these compounds were almost half as high. These facts indicate the importance of the senescence process on TTL accumulation. Some flavonoids and phenolic acids also showed changes in content related to maturation or senescence. Generally, the application of JA-Me slightly but substantially increased the levels of TTLs in leaf blades irrespective of the difference in its application side on the leaves. Of the flavonoids analyzed, levels of quercetin, rutin, quercetin-4-glucoside, apigenin, and luteolin were dependent on the JA-Me application site, whereas levels of (+) catechin and (-) epicatechin were not. Application of JA-Me increased ferulic acid and p-coumaric acid esters in the petiole but decreased the levels of these compounds in the leaf blade. The content of p-coumaric acid glycosides and caffeic acid esters was only slightly modified by JA-Me. In general, JA-Me application affected leaf senescence by modifying the accumulation of ginkogolides, flavonoids, and phenolic acids. These effects were also found to be different in leaf blades and petioles. Based on JA-Me- and aging-related metabolic changes in endogenous levels of the secondary metabolites in G. biloba leaves, we discussed the results of study in the context of basic research and possible practical application.


Assuntos
Senescência Celular , Ciclopentanos/farmacologia , Flavonoides/metabolismo , Ginkgo biloba/metabolismo , Hidroxibenzoatos/metabolismo , Lactonas/metabolismo , Oxilipinas/farmacologia , Folhas de Planta/metabolismo , Flavonoides/análise , Ginkgo biloba/efeitos dos fármacos , Ginkgo biloba/crescimento & desenvolvimento , Hidroxibenzoatos/análise , Lactonas/análise , Reguladores de Crescimento de Plantas/farmacologia , Folhas de Planta/efeitos dos fármacos , Folhas de Planta/crescimento & desenvolvimento , Terpenos/análise , Terpenos/metabolismo
5.
BMC Plant Biol ; 21(1): 401, 2021 Aug 30.
Artigo em Inglês | MEDLINE | ID: mdl-34461825

RESUMO

BACKGROUND: Timing is everything when it comes to the fitness outcome of a plant's ecological interactions, and accurate timing is particularly relevant for interactions with herbivores or mutualists that are based on ephemeral emissions of volatile organic compounds. Previous studies of the wild tobacco N. attenuata have found associations between the diurnal timing of volatile emissions, and daytime predation of herbivores by their natural enemies. RESULTS: Here, we investigated the role of light in regulating two biosynthetic groups of volatiles, terpenoids and green leaf volatiles (GLVs), which dominate the herbivore-induced bouquet of N. attenuata. Light deprivation strongly suppressed terpenoid emissions while enhancing GLV emissions, albeit with a time lag. Silencing the expression of photoreceptor genes did not alter terpenoid emission rhythms, but silencing expression of the phytochrome gene, NaPhyB1, disordered the emission of the GLV (Z)-3-hexenyl acetate. External abscisic acid (ABA) treatments increased stomatal resistance, but did not truncate the emission of terpenoid volatiles (recovered in the headspace). However, ABA treatment enhanced GLV emissions and leaf internal pools (recovered from tissue), and reduced internal linalool pools. In contrast to the pattern of diurnal terpenoid emissions and nocturnal GLV emissions, transcripts of herbivore-induced plant volatile (HIPV) biosynthetic genes peaked during the day. The promotor regions of these genes were populated with various cis-acting regulatory elements involved in light-, stress-, phytohormone- and circadian regulation. CONCLUSIONS: This research provides insights into the complexity of the mechanisms involved in the regulation of HIPV bouquets, a mechanistic complexity which rivals the functional complexity of HIPVs, which includes repelling herbivores, calling for body guards, and attracting pollinators.


Assuntos
Ritmo Circadiano , Herbivoria/fisiologia , Luz , Tabaco/fisiologia , Compostos Orgânicos Voláteis/metabolismo , Ácido Abscísico/farmacologia , Animais , Regulação da Expressão Gênica de Plantas/efeitos dos fármacos , Regulação da Expressão Gênica de Plantas/fisiologia , Larva/fisiologia , Mariposas/fisiologia , Fitocromo B/genética , Fitocromo B/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Terpenos/metabolismo
6.
Plant Cell Rep ; 40(10): 1923-1946, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34333679

RESUMO

KEY MESSAGE: Combined transcriptomic and metabolic analyses reveal that fruit of Rubus chingii Hu launches biosynthesis of phenolic acids and flavonols at beginning of fruit set and then coordinately accumulated or converted to their derivatives. Rubus chingii Hu (Chinese raspberry) is an important dual functional food with nutraceutical and pharmaceutical values. Comprehensively understanding the mechanisms of fruit development and bioactive components synthesis and regulation could accelerate genetic analysis and molecular breeding for the unique species. Combined transcriptomic and metabolic analyses of R. chingii fruits from different developmental stages, including big green, green-to-yellow, yellow-to-orange, and red stages, were conducted. A total of 89,188 unigenes were generated and 57,545 unigenes (64.52%) were annotated. Differential expression genes (DEGs) and differentially accumulated metabolites (DAMs) were mainly involved in the biosynthesis of secondary metabolites. The fruit launched the biosynthesis of phenolic acids and flavonols at the very beginning of fruit set and then coordinately accumulated or converted to their derivatives. This was tightly regulated by expressions of the related genes and MYB and bHLH transcription factors. The core genes products participated in the biosynthesis of ellagic acid (EA) and kaempferol-3-O-rutinoside (K-3-R), such as DAHPS, DQD/SDH, PAL, 4CL, CHS, CHI, F3H, F3'H, FLS, and UGT78D2, and their corresponding metabolites were elaborately characterized. Our research reveals the molecular and chemical mechanisms of the fruit development of R. chingii. The results provide a solid foundation for the genetic analysis, functional genes isolation, fruit quality improvement and modifiable breeding of R. chingii.


Assuntos
Ácido Elágico , Frutas/crescimento & desenvolvimento , Frutas/metabolismo , Regulação da Expressão Gênica de Plantas , Rubus/crescimento & desenvolvimento , Ácido Elágico/metabolismo , Flavonóis/biossíntese , Flavonóis/genética , Frutas/genética , Perfilação da Expressão Gênica , Hidroxibenzoatos/metabolismo , Quempferóis/genética , Quempferóis/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Controle de Qualidade , Rubus/genética , Rubus/metabolismo , Terpenos/metabolismo , Fatores de Transcrição/genética , Fatores de Transcrição/metabolismo
7.
Chin J Nat Med ; 19(8): 591-607, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34419259

RESUMO

Terpenoid indole (TIAs) and ß-carboline alkaloids (BCAs), such as suppressant reserpine, vasodilatory yohimbine, and antimalarial quinine, are natural compounds derived from strictosidine. These compounds can exert powerful pharmacological effects but be obtained from limited source in nature. the whole biosynthetic pathway of TIAs and BCAs, The Pictet-Spengler reaction catalyzed by strictosidine synthase (STR; EC: 4.3.3.2) is the rate-limiting step. Therefore, it is necessary to investigate their biosynthesis pathways, especially the role of STR, and related findings will support the biosynthetic generation of natural and unnatural compounds. This review summarizes the latest studies concerning the function of STR in TIA and BCA biosynthesis, and illustrates the compounds derived from strictosidine. The substrate specificity of STR based on its structure is also summarized. Proteins that contain six-bladed four-stranded ß-propeller folds in many organisms, other than plants, are listed. The presence of these folds may lead to similar functions among organisms. The expression of STR gene can greatly influence the production of many compounds. STR is mainly applied to product various valuable drugs in plant cell suspension culture and biosynthesis in other carriers.


Assuntos
Alcaloides , Carbolinas/metabolismo , Carbono-Nitrogênio Liases , Indóis/metabolismo , Terpenos , Alcaloides/biossíntese , Terpenos/metabolismo
8.
Nat Commun ; 12(1): 4417, 2021 07 20.
Artigo em Inglês | MEDLINE | ID: mdl-34285212

RESUMO

Endoperoxide-containing natural products are a group of compounds with structurally unique cyclized peroxide moieties. Although numerous endoperoxide-containing compounds have been isolated, the biosynthesis of the endoperoxides remains unclear. NvfI from Aspergillus novofumigatus IBT 16806 is an endoperoxidase that catalyzes the formation of fumigatonoid A in the biosynthesis of novofumigatonin. Here, we describe our structural and functional analyses of NvfI. The structural elucidation and mutagenesis studies indicate that NvfI does not utilize a tyrosyl radical in the reaction, in contrast to other characterized endoperoxidases. Further, the crystallographic analysis reveals significant conformational changes of two loops upon substrate binding, which suggests a dynamic movement of active site during the catalytic cycle. As a result, NvfI installs three oxygen atoms onto a substrate in a single enzyme turnover. Based on these results, we propose a mechanism for the NvfI-catalyzed, unique endoperoxide formation reaction to produce fumigatonoid A.


Assuntos
Aspergillus/enzimologia , Biocatálise , Proteínas Fúngicas/metabolismo , Oxigenases/metabolismo , Peróxidos/metabolismo , Aspergillus/genética , Domínio Catalítico , Cristalografia por Raios X , Compostos Ferrosos/metabolismo , Proteínas Fúngicas/genética , Proteínas Fúngicas/isolamento & purificação , Proteínas Fúngicas/ultraestrutura , Ácidos Cetoglutáricos/metabolismo , Mutagênese Sítio-Dirigida , Oxirredução , Oxigênio/metabolismo , Oxigenases/genética , Oxigenases/isolamento & purificação , Oxigenases/ultraestrutura , Conformação Proteica em Folha beta , Proteínas Recombinantes/genética , Proteínas Recombinantes/isolamento & purificação , Proteínas Recombinantes/metabolismo , Proteínas Recombinantes/ultraestrutura , Terpenos/metabolismo
9.
Int J Biol Macromol ; 185: 949-958, 2021 Aug 31.
Artigo em Inglês | MEDLINE | ID: mdl-34237366

RESUMO

Acyclic terpenes, commonly found in plants, are of high physiological importance and commercial value, and their diversity was controlled by different terpene synthases. During the screen of sesquiterpene synthases from Tripterygium wilfordii, we observed that Ses-TwTPS1-1 and Ses-TwTPS2 promiscuously accepted GPP, FPP, and GGPP to produce corresponding terpene alcohols (linalool/nerolidol/geranyllinalool). The Ses-TwTPS1-2, Ses-TwTPS3, and Ses-TwTPS4 also showed unusual substrate promiscuity by catalyzing GGPP or GPP in addition to FPP as substrate. Furthermore, key residues for the generation of diterpene product, (E, E)-geranyllinalool, were screened depending on mutagenesis studies. The functional analysis of Ses-TwTPS1-1:V199I and Ses-TwTPS1-2:I199V showed that Val in 199 site assisted the produce of diterpene product geranyllinalool by enzyme mutation studies, which indicated that subtle differences away from the active site could alter the product outcome. Moreover, an engineered sesquiterpene high-yielding yeast that produced 162 mg/L nerolidol in shake flask conditions was constructed to quickly identify the function of sesquiterpene synthases in vivo and develop potential applications in microbial fermentation. Our functional characterization of acyclic sesquiterpene synthases will give some insights into the substrate promiscuity of diverse acyclic terpene synthases and provide key residues for expanding the product portfolio.


Assuntos
Alquil e Aril Transferases/genética , Alquil e Aril Transferases/metabolismo , Tripterygium/enzimologia , Alquil e Aril Transferases/química , Domínio Catalítico , Cromatografia Gasosa-Espectrometria de Massas , Regulação Enzimológica da Expressão Gênica , Regulação da Expressão Gênica de Plantas , Mutagênese Sítio-Dirigida , Proteínas de Plantas/química , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo , Especificidade por Substrato , Terpenos/metabolismo , Tripterygium/genética
10.
Nat Commun ; 12(1): 4563, 2021 07 27.
Artigo em Inglês | MEDLINE | ID: mdl-34315897

RESUMO

The emergence and spread of Plasmodium falciparum parasites resistant to front-line antimalarial artemisinin-combination therapies (ACT) threatens to erase the considerable gains against the disease of the last decade. Here, we develop a large-scale phenotypic screening pipeline and use it to carry out a large-scale forward-genetic phenotype screen in P. falciparum to identify genes allowing parasites to survive febrile temperatures. Screening identifies more than 200 P. falciparum mutants with differential responses to increased temperature. These mutants are more likely to be sensitive to artemisinin derivatives as well as to heightened oxidative stress. Major processes critical for P. falciparum tolerance to febrile temperatures and artemisinin include highly essential, conserved pathways associated with protein-folding, heat shock and proteasome-mediated degradation, and unexpectedly, isoprenoid biosynthesis, which originated from the ancestral genome of the parasite's algal endosymbiont-derived plastid, the apicoplast. Apicoplast-targeted genes in general are upregulated in response to heat shock, as are other Plasmodium genes with orthologs in plant and algal genomes. Plasmodium falciparum parasites appear to exploit their innate febrile-response mechanisms to mediate resistance to artemisinin. Both responses depend on endosymbiont-derived genes in the parasite's genome, suggesting a link to the evolutionary origins of Plasmodium parasites in free-living ancestors.


Assuntos
Apicoplastos/metabolismo , Artemisininas/farmacologia , Resistência a Medicamentos , Febre/parasitologia , Malária Falciparum/parasitologia , Parasitos/fisiologia , Animais , Apicoplastos/efeitos dos fármacos , Resistência a Medicamentos/efeitos dos fármacos , Regulação da Expressão Gênica/efeitos dos fármacos , Resposta ao Choque Térmico/efeitos dos fármacos , Mutação/genética , Parasitos/efeitos dos fármacos , Fenótipo , Plasmodium falciparum/genética , Transdução de Sinais/efeitos dos fármacos , Temperatura , Terpenos/metabolismo , Transcrição Genética/efeitos dos fármacos , Resposta a Proteínas não Dobradas/efeitos dos fármacos
11.
Biomolecules ; 11(6)2021 06 16.
Artigo em Inglês | MEDLINE | ID: mdl-34208762

RESUMO

Interactions between plant-associated fungi and their hosts are characterized by a continuous crosstalk of chemical molecules. Specialized metabolites are often produced during these associations and play important roles in the symbiosis between the plant and the fungus, as well as in the establishment of additional interactions between the symbionts and other organisms present in the niche. Serendipita indica, a root endophytic fungus from the phylum Basidiomycota, is able to colonize a wide range of plant species, conferring many benefits to its hosts. The genome of S. indica possesses only few genes predicted to be involved in specialized metabolite biosynthesis, including a putative terpenoid synthase gene (SiTPS). In our experimental setup, SiTPS expression was upregulated when the fungus colonized tomato roots compared to its expression in fungal biomass growing on synthetic medium. Heterologous expression of SiTPS in Escherichia coli showed that the produced protein catalyzes the synthesis of a few sesquiterpenoids, with the alcohol viridiflorol being the main product. To investigate the role of SiTPS in the plant-endophyte interaction, an SiTPS-over-expressing mutant line was created and assessed for its ability to colonize tomato roots. Although overexpression of SiTPS did not lead to improved fungal colonization ability, an in vitro growth-inhibition assay showed that viridiflorol has antifungal properties. Addition of viridiflorol to the culture medium inhibited the germination of spores from a phytopathogenic fungus, indicating that SiTPS and its products could provide S. indica with a competitive advantage over other plant-associated fungi during root colonization.


Assuntos
Alquil e Aril Transferases/isolamento & purificação , Basidiomycota/enzimologia , Sesquiterpenos/metabolismo , Alquil e Aril Transferases/genética , Alquil e Aril Transferases/metabolismo , Basidiomycota/metabolismo , Endófitos/metabolismo , Regulação da Expressão Gênica de Plantas/genética , Lycopersicon esculentum/metabolismo , Raízes de Plantas/metabolismo , Simbiose/genética , Terpenos/química , Terpenos/metabolismo
12.
Biomolecules ; 11(7)2021 06 29.
Artigo em Inglês | MEDLINE | ID: mdl-34209734

RESUMO

Meroterpenoids are secondary metabolites formed due to mixed biosynthetic pathways which are produced in part from a terpenoid co-substrate. These mixed biosynthetically hybrid compounds are widely produced by bacteria, algae, plants, and animals. Notably amazing chemical diversity is generated among meroterpenoids via a combination of terpenoid scaffolds with polyketides, alkaloids, phenols, and amino acids. This review deals with the isolation, chemical diversity, and biological effects of 452 new meroterpenoids reported from natural sources from January 2016 to December 2020. Most of the meroterpenoids possess antimicrobial, cytotoxic, antioxidant, anti-inflammatory, antiviral, enzyme inhibitory, and immunosupressive effects.


Assuntos
Terpenos/química , Terpenos/isolamento & purificação , Terpenos/metabolismo , Alcaloides , Animais , Antibacterianos/metabolismo , Anti-Infecciosos/metabolismo , Antineoplásicos/metabolismo , Antioxidantes/metabolismo , Bactérias/metabolismo , Benzopiranos , Benzoquinonas , Produtos Biológicos/química , Vias Biossintéticas , Fungos/metabolismo , Humanos , Metabolismo Secundário/fisiologia , Sesquiterpenos
13.
Int J Mol Sci ; 22(13)2021 Jul 02.
Artigo em Inglês | MEDLINE | ID: mdl-34281238

RESUMO

This study evaluated the effects of different light spectra (white light; WL, blue light; BL and red light; RL) on the root morphological traits and metabolites accumulation and biosynthesis in Sarcandra glabra. We performed transcriptomic and metabolomic profiling by RNA-seq and ultra-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UPLC-ESI-MS/MS), respectively. When morphological features were compared to WL, BL substantially increased under-ground fresh weight, root length, root surface area, and root volume, while RL inhibited these indices. A total of 433 metabolites were identified, of which 40, 18, and 68 compounds differentially accumulated in roots under WL (WG) vs. roots under BL (BG), WG vs. roots under RL (RG), and RG vs. BG, respectively. In addition, the contents of sinapyl alcohol, sinapic acid, fraxetin, and 6-methylcoumarin decreased significantly in BG and RG. In contrast, chlorogenic acid, rosmarinyl glucoside, quercitrin and quercetin were increased considerably in BG. Furthermore, the contents of eight terpenoids compounds significantly reduced in BG. Following transcriptomic profiling, several key genes related to biosynthesis of phenylpropanoid-derived and terpenoids metabolites were differentially expressed, such as caffeic acid 3-O-methyltransferase) (COMT), hydroxycinnamoyl-CoA shikimate hydroxycinnamoyl transferase (HCT), O-methyltransferase (OMT), and 1-deoxy-D-xylulose-5-phosphate synthetase (DXS). In summary, our findings showed that BL was suitable for growth and accumulation of bioactive metabolites in root tissue of S. glabra. Exposure to a higher ratio of BL might have the potential to improve the production and quality of S. glabra seedlings, but this needs to be confirmed further.


Assuntos
Cor , Magnoliopsida/efeitos da radiação , Raízes de Plantas/efeitos da radiação , Metabolismo Secundário/efeitos da radiação , Plântula/efeitos da radiação , Magnoliopsida/crescimento & desenvolvimento , Magnoliopsida/metabolismo , Raízes de Plantas/crescimento & desenvolvimento , Raízes de Plantas/metabolismo , Plântula/crescimento & desenvolvimento , Plântula/metabolismo , Terpenos/metabolismo
14.
Int J Mol Sci ; 22(11)2021 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-34071919

RESUMO

Biodiversity is adversely affected by the growing levels of synthetic chemicals released into the environment due to agricultural activities. This has been the driving force for embracing sustainable agriculture. Plant secondary metabolites offer promising alternatives for protecting plants against microbes, feeding herbivores, and weeds. Terpenes are the largest among PSMs and have been extensively studied for their potential as antimicrobial, insecticidal, and weed control agents. They also attract natural enemies of pests and beneficial insects, such as pollinators and dispersers. However, most of these research findings are shelved and fail to pass beyond the laboratory and greenhouse stages. This review provides an overview of terpenes, types, biosynthesis, and their roles in protecting plants against microbial pathogens, insect pests, and weeds to rekindle the debate on using terpenes for the development of environmentally friendly biopesticides and herbicides.


Assuntos
Vias Biossintéticas , Resistência à Doença , Fenômenos Fisiológicos Vegetais , Terpenos/metabolismo , Alelos , Anti-Infecciosos , Suscetibilidade a Doenças , Predisposição Genética para Doença , Interações Hospedeiro-Patógeno , Estrutura Molecular , Doenças das Plantas/etiologia , Doenças das Plantas/microbiologia , Terpenos/química , Terpenos/farmacologia
15.
BMC Plant Biol ; 21(1): 279, 2021 Jun 19.
Artigo em Inglês | MEDLINE | ID: mdl-34147088

RESUMO

BACKGROUND: 3-Hydroxy-3-methylglutaryl-CoA reductase (HMGR) is a key enzyme in the mevalonate (MVA) pathway, which regulates the metabolism of terpenoids in the cytoplasm and determines the type and content of downstream terpenoid metabolites. RESULTS: Results showed that grapevine HMGR family has three members, such as VvHMGR1, VvHMGR2, and VvHMGR3. The expression of VvHMGRs in 'Kyoho' has tissue specificity, for example, VvHMGR1 keeps a higher expression, VvHMGR2 is the lowest, and VvHMGR3 gradually decreases as the fruit development. VvHMGR3 is closely related to CsHMGR1 and GmHMGR9 and has collinearity with CsHMGR2 and GmHMGR4. By the prediction of interaction protein, it can interact with HMG-CoA synthase, MVA kinase, FPP/GGPP synthase, diphosphate mevalonate decarboxylase, and participates in the synthesis and metabolism of terpenoids. VvHMGR3 have similar trends in expression with some of the genes of carotenoid biosynthesis and MEP pathways. VvHMGR3 responds to various environmental and phytohormone stimuli, especially salt stress and ultraviolet (UV) treatment. The expression level of VvHMGRs is diverse in grapes of different colors and aroma. VvHMGRs are significantly higher in yellow varieties than that in red varieties, whereas rose-scented varieties showed significantly higher expression than that of strawberry aroma. The expression level is highest in yellow rose-scented varieties, and the lowest in red strawberry scent varieties, especially 'Summer Black' and 'Fujiminori'. CONCLUSION: This study confirms the important role of VvHMGR3 in the process of grape fruit coloring and aroma formation, and provided a new idea to explain the loss of grape aroma and poor coloring during production. There may be an additive effect between color and aroma in the HMGR expression aspect.


Assuntos
Genes de Plantas , Hidroximetilglutaril-CoA Redutases/genética , Vitis/enzimologia , Vitis/genética , Antocianinas/metabolismo , Evolução Molecular , Frutas/genética , Frutas/crescimento & desenvolvimento , Frutas/fisiologia , Perfilação da Expressão Gênica , Variação Genética , Genótipo , Família Multigênica , Pressão Osmótica , Reguladores de Crescimento de Plantas/fisiologia , Terpenos/metabolismo , Vitis/crescimento & desenvolvimento
16.
Eur J Med Chem ; 223: 113665, 2021 Nov 05.
Artigo em Inglês | MEDLINE | ID: mdl-34192642

RESUMO

New types of antidiabetic agents are continually needed with diabetes becoming the epidemic in the world. Indole alkaloids play an important role in natural products owing to their variable structures and versatile biological activities like anticonvulsant, anti-inflammatory, antidiabetic, antimicrobial, and anticancer activities, which are a promising source of novel antidiabetic drugs discovery. The synthesized indole derivatives possess similar properties to natural indole alkaloids. In the last two decades, more and more indole derivatives have been designed and synthesized for searching their bioactivities. This present review describes comprehensive structures of indole compounds with the potential antidiabetic activity including natural indole alkaloids and the synthetic indole derivatives based on the structure classification, summarizes their approaches isolated from natural sources or by synthetic methods, and discusses the antidiabetic effects and the mechanisms of action. Furthermore, this review also provides briefly synthetic procedures of some important indole derivatives.


Assuntos
Hipoglicemiantes/química , Indóis/química , Carbolinas/química , Carbolinas/metabolismo , Carbolinas/uso terapêutico , Diabetes Mellitus/tratamento farmacológico , Humanos , Hipoglicemiantes/síntese química , Hipoglicemiantes/metabolismo , Hipoglicemiantes/uso terapêutico , Indóis/metabolismo , Indóis/uso terapêutico , PPAR alfa/química , PPAR alfa/metabolismo , PPAR gama/química , PPAR gama/metabolismo , Terpenos/química , Terpenos/metabolismo , Terpenos/uso terapêutico
17.
Elife ; 102021 06 23.
Artigo em Inglês | MEDLINE | ID: mdl-34161230

RESUMO

Volatile organic compounds (VOCs) from 'emitting' plants inform the 'receiving' (listening) plants of impending stresses or simply of their presence. However, the receptors that allow receivers to detect the volatile cue are elusive. Most likely, plants (as animals) have odorant-binding proteins (OBPs), and in fact, a few OBPs are known to bind 'stress-induced' plant VOCs. We investigated whether these and other putative OBPs may bind volatile constitutive and stress-induced isoprenoids, the most emitted plant VOCs, with well-established roles in plant communication and defense. Molecular docking simulation experiments suggest that structural features of a few plant proteins screened in databases could allow VOC binding. In particular, our results show that monoterpenes may bind the same plant proteins that were described to bind other stress-induced VOCs, while the constitutive hemiterpene isoprene is unlikely to bind any investigated putative OBP and may not have an info-chemical role. We conclude that, as for animal, there may be plant OBPs that bind multiple VOCs. Plant OBPs may play an important role in allowing plants to eavesdrop messages by neighboring plants, triggering defensive responses and communication with other organisms.


Assuntos
Arabidopsis/metabolismo , Oryza/metabolismo , Proteínas de Plantas/metabolismo , Receptores Odorantes/metabolismo , Terpenos/metabolismo , Tabaco/metabolismo , Compostos Orgânicos Voláteis/metabolismo , Proteínas de Arabidopsis/metabolismo , Simulação por Computador
18.
mBio ; 12(3): e0088121, 2021 06 29.
Artigo em Inglês | MEDLINE | ID: mdl-34182781

RESUMO

Understanding carbon flux controlling mechanisms in a tangled metabolic network is an essential question of cell metabolism. Secondary metabolism, such as terpene biosynthesis, has evolved with low carbon flux due to inherent pathway constraints. Thraustochytrids are a group of heterotrophic marine unicellular protists and can accumulate terpenoids under the high-salt conditions in their natural environment. However, the mechanism behind terpene accumulation is not well understood. Here, we show that terpene biosynthesis in Thraustochytrium sp. ATCC 26185 is constrained by local thermodynamics in the mevalonate pathway. Thermodynamic analysis reveals metabolite limitation in the nondecarboxylative Claisen condensation of acetyl-coenzyme A (CoA) to the acetoacetyl-CoA step, catalyzed by the acetyl-CoA acetyltransferase (ACAT). Through a sodium-elicited mechanism, higher respiration leads to increased ATP investment into the mevalonate pathway, providing a strong thermodynamic driving force for enhanced terpene biosynthesis. Proteomic and metabolomic analyses further show that the increased ATP demands are fulfilled by shifting energy generation from carbohydrate to lipid oxidation. This study demonstrates a unique strategy in nature that uses ATP to drive a low-flux metabolic pathway, providing an alternative solution for efficient terpene metabolic engineering. IMPORTANCE Terpenoids are a large class of lipid molecules with important biological functions and diverse industrial and medicinal applications. Metabolic engineering for terpene production has been hindered by the low-flux distribution to its biosynthesis pathway. In practice, a high substrate load is generally required to reach high product titers. Here, we show that mevalonate-derived terpene biosynthesis is constrained by local pathway thermodynamics, which can only be partially relieved by increasing substrate levels. Through comparative omics and biochemical analyses, we discovered a unique mechanism for high terpene accumulation in marine protist thraustochytrids. Through a sodium-induced mechanism, thraustochytrids shift their energy metabolism from carbohydrate to lipid oxidation for enhanced ATP production, providing a strong thermodynamic driving force for efficient terpene biosynthesis. This study reveals an important mechanism in eukaryotes to overcome the thermodynamic constraint in low-flux pathways by increased ATP consumption. Engineering energy metabolism thus provides an important alternative to relieve flux constraints in low-flux and energy-consuming pathways.


Assuntos
Trifosfato de Adenosina/metabolismo , Vias Biossintéticas , Ácido Mevalônico/metabolismo , Metabolismo Secundário , Estramenópilas/metabolismo , Terpenos/metabolismo , Organismos Aquáticos/genética , Organismos Aquáticos/metabolismo , Engenharia Metabólica , Estramenópilas/genética
19.
Chem Pharm Bull (Tokyo) ; 69(5): 444-446, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33952854

RESUMO

Structurally diverse fungal meroterpenoids are promising drug seed compounds. To obtain unnatural, novel meroterpene scaffolds, we tested combinatorial biosynthesis by co-expressing functionally distinct terpene cyclase (TPC) genes, pyr4, ascF, andB, or cdmG, with the biosynthetic genes for the production of a TPC substrate, (10'R)-epoxyfarnesyl-dimethylorsellinic acid-3,5-methyl ester, in Aspergillus oryzae NSAR1 as a heterologous host. As a result, all of the tested TPCs afforded the same two novel mono-cyclization products. This study provides important information on the substrate scope of the TPCs, and will contribute to the production of unnatural, novel molecules for future drug discovery.


Assuntos
Alquil e Aril Transferases/metabolismo , Ciclopentanos/metabolismo , Terpenos/metabolismo , Alquil e Aril Transferases/genética , Aspergillus oryzae/enzimologia , Biocatálise , Ciclopentanos/química , Estrutura Molecular , Terpenos/química
20.
Microb Cell Fact ; 20(1): 106, 2021 May 27.
Artigo em Inglês | MEDLINE | ID: mdl-34044821

RESUMO

BACKGROUND: ß-Caryophyllene is a plant terpenoid with therapeutic and biofuel properties. Production of terpenoids through microbial cells is a potentially sustainable alternative for production. Adaptive laboratory evolution is a complementary technique to metabolic engineering for strain improvement, if the product-of-interest is coupled with growth. Here we use a combination of pathway engineering and adaptive laboratory evolution to improve the production of ß-caryophyllene, an extracellular product, by leveraging the antioxidant potential of the compound. RESULTS: Using oxidative stress as selective pressure, we developed an adaptive laboratory evolution that worked to evolve an engineered ß-caryophyllene producing yeast strain for improved production within a few generations. This strategy resulted in fourfold increase in production in isolated mutants. Further increasing the flux to ß-caryophyllene in the best evolved mutant achieved a titer of 104.7 ± 6.2 mg/L product. Genomic analysis revealed a gain-of-function mutation in the a-factor exporter STE6 was identified to be involved in significantly increased production, likely as a result of increased product export. CONCLUSION: An optimized selection strategy based on oxidative stress was developed to improve the production of the extracellular product ß-caryophyllene in an engineered yeast strain. Application of the selection strategy in adaptive laboratory evolution resulted in mutants with significantly increased production and identification of novel responsible mutations.


Assuntos
Evolução Biológica , Engenharia Metabólica , Sesquiterpenos Policíclicos/metabolismo , Saccharomyces cerevisiae/metabolismo , Adaptação Biológica , Biotecnologia/métodos , Fermentação , Microbiologia Industrial , Laboratórios , Terpenos/metabolismo
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