Erythrina velutina Willd. alkaloids: Piecing biosynthesis together from transcriptome analysis and metabolite profiling of seeds and leaves

Chacon, Daisy Sotero; Torres, Taffarel Melo; Silva, Ivanice Bezerra da; Araújo, Thiago Ferreira de; Roque, Alan de Araújo; Pinheiro, Francisco Ayrton Senna Domingos; Selegato, Denise Medeiros; Pilon, Alan César; Reginaldo, Fernanda Priscila Santos; Costa, Cibele Tesser da; Vilasboa, Johnatan; Freire, Rafael Teixeira; Voigt, Eduardo Luiz; Zuanazzi, José Ângelo Silveira; Libonati, Renata; Rodrigues, Julia Abrantes; Santos, Filippe L.M.; Scortecci, Kátia Castanho; Lopes, Norberto Peporine; Ferreira, Leandro de Santis; Santos, Leandro Vieira dos; Cavalheiro, Alberto José; Fett-Neto, Arthur Germano; Giordani, Raquel Brandt

doi:10.1016/j.jare.2021.01.017

Cited by 5 publications

(11 citation statements)

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“…Harvesting and processing of plant material, metabolite extraction, and HR-LC-DAD-ESI-MS/AutoMS data acquisition were as described in Chacon et al ( 2021b ). Samples of seeds and leaves were harvested at daytime during the dry season from natural populations ( Supplementary Table 1 ), composed of 5–10 trees of Erythrina velutina Willd in different locations and subjected to a multi-omics analyses approach (transcriptomics, proteomics, and metabolomics).…”

Section: Methodsmentioning

confidence: 99%

“…Although Erythrina metabolites show diversity in chemical structures and biological potential, most of these bioactive natural products (NPs) are present in small amounts, which hampers extraction and detection by analytical techniques, and makes the process a major challenge for development of new products (Feitosa et al, 2012 ; Chacon et al, 2021b ; Phukhatmuen et al, 2021 ). Alternatives to tackle low yields and excess of contaminants include metabolic engineering in microorganisms, semi-synthesis, and combinatorial biosynthesis, which can facilitate large-scale production of NPs (Atanasov et al, 2015 ).…”

Section: Introductionmentioning

confidence: 99%

“…The first transcriptomic study involving Erythrina velutina was recently published by our group. This experimental approach enabled a first look at the genes associated with the chemical diversification process of isoquinoline alkaloids, as well as an overview of their putative biosynthesis pathways in the Erythrina genus, in particular of a medicinal native species of the Caatinga (Chacon et al, 2021b ). Herein, our analysis is focused on flavonoid biosynthesis, another major class of NPs with important in planta roles and significant pharmacological interest.…”

Section: Introductionmentioning

confidence: 99%

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Non-target molecular network and putative genes of flavonoid biosynthesis in Erythrina velutina Willd., a Brazilian semiarid native woody plant

et al. 2022

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Erythrina velutina is a Brazilian native tree of the Caatinga (a unique semiarid biome). It is widely used in traditional medicine showing anti-inflammatory and central nervous system modulating activities. The species is a rich source of specialized metabolites, mostly alkaloids and flavonoids. To date, genomic information, biosynthesis, and regulation of flavonoids remain unknown in this woody plant. As part of a larger ongoing research goal to better understand specialized metabolism in plants inhabiting the harsh conditions of the Caatinga, the present study focused on this important class of bioactive phenolics. Leaves and seeds of plants growing in their natural habitat had their metabolic and proteomic profiles analyzed and integrated with transcriptome data. As a result, 96 metabolites (including 43 flavonoids) were annotated. Transcripts of the flavonoid pathway totaled 27, of which EvCHI, EvCHR, EvCHS, EvCYP75A and EvCYP75B1 were identified as putative main targets for modulating the accumulation of these metabolites. The highest correspondence of mRNA vs. protein was observed in the differentially expressed transcripts. In addition, 394 candidate transcripts encoding for transcription factors distributed among the bHLH, ERF, and MYB families were annotated. Based on interaction network analyses, several putative genes of the flavonoid pathway and transcription factors were related, particularly TFs of the MYB family. Expression patterns of transcripts involved in flavonoid biosynthesis and those involved in responses to biotic and abiotic stresses were discussed in detail. Overall, these findings provide a base for the understanding of molecular and metabolic responses in this medicinally important species. Moreover, the identification of key regulatory targets for future studies aiming at bioactive metabolite production will be facilitated.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Non-target molecular network and putative genes of flavonoid biosynthesis in Erythrina velutina Willd., a Brazilian semiarid native woody plant

et al. 2022

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“…One of these approaches is the concept of spectral similarity networking (so-called molecular networks—MN) which is based on the organization and visualization of MS/MS data via spectral similarity (homologous fragments) [ 24 , 34 , 35 , 36 , 37 , 38 , 39 ]. Structurally related compounds often share similar MS/MS spectra.…”

Section: Introductionmentioning

confidence: 99%

Combination of GC-MS Molecular Networking and Larvicidal Effect against Aedes aegypti for the Discovery of Bioactive Substances in Commercial Essential Oils

et al. 2022

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Dengue is a neglected disease, present mainly in tropical countries, with more than 5.2 million cases reported in 2019. Vector control remains the most effective protective measure against dengue and other arboviruses. Synthetic insecticides based on organophosphates, pyrethroids, carbamates, neonicotinoids and oxadiazines are unattractive due to their high degree of toxicity to humans, animals and the environment. Conversely, natural-product-based larvicides/insecticides, such as essential oils, present high efficiency, low environmental toxicity and can be easily scaled up for industrial processes. However, essential oils are highly complex and require modern analytical and computational approaches to streamline the identification of bioactive substances. This study combined the GC-MS spectral similarity network approach with larvicidal assays as a new strategy for the discovery of potential bioactive substances in complex biological samples, enabling the systematic and simultaneous annotation of substances in 20 essential oils through LC50 larvicidal assays. This strategy allowed rapid intuitive discovery of distribution patterns between families and metabolic classes in clusters, and the prediction of larvicidal properties of acyclic monoterpene derivatives, including citral, neral, citronellal and citronellol, and their acetate forms (LC50 < 50 µg/mL).

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“…Recently, transcriptome analysis and metabolic profiling have been extensively used to explore and identify critical genes related to the biosynthesis and regulation of secondary metabolites in medicinal plants, such as Gloriosa superba ( Nett et al, 2020 ), Cinnamomum camphora ( Chen et al, 2018 ), and Atractylodes macrocephala ( Ruan et al, 2021 ). Using this integrative approach, several crucial genes ((S)-coclaurine N-methyltransferase, (S)-N-methylcoclaurine-3-hydroxylase) have been identified in Corydalis yanhusuo ( Xu et al, 2021 ), Coptis deltoidea ( Zhong et al, 2020 ), and Erythrina velutina Willd ( Chacon et al, 2021 ). These results shed light on the biosynthesis of BIAs in S. tetrandra .…”

Section: Introductionmentioning

confidence: 99%

Transcriptome Analysis of Stephania tetrandra and Characterization of Norcoclaurine-6-O-Methyltransferase Involved in Benzylisoquinoline Alkaloid Biosynthesis

Chen

Zhang

et al. 2022

Front. Plant Sci.

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Stephania tetrandra (S. Moore) is a source of traditional Chinese medicine that is widely used to treat rheumatism, rheumatoid arthritis, edema, and hypertension. Benzylisoquinoline alkaloids (BIAs) are the main bioactive compounds. However, the current understanding of the biosynthesis of BIAs in S. tetrandra is poor. Metabolite and transcriptomic analyses of the stem, leaf, xylem, and epidermis of S. tetrandra were performed to identify candidate genes associated with BIAs biosynthesis. According to the metabolite analysis, the majority of the BIAs accumulated in the root, especially in the epidermis. Transcriptome sequencing revealed a total of 113,338 unigenes that were generated by de novo assembly. Among them, 79,638 unigenes were successfully annotated, and 42 candidate structural genes associated with 15 steps of BIA biosynthesis identified. Additionally, a new (S)-norcoclaurine-6-O-methyltransferase (6OMT) gene was identified in S. tetrandra, named St6OMT2. Recombinant St6OMT2 catalyzed (S)-norcoclaurine methylation to form (S)-coclaurine in vitro. Maximum activity of St6OMT2 was determined at 30°C and pH 6.0 in NaAc-HAc buffer. Its half-life at 50°C was 22 min with the Km and kcat of 28.2 μM and 1.5 s−1, respectively. Our results provide crucial transcriptome information for S. tetrandra, shedding light on the understanding of BIAs biosynthesis and further gene functional characterization.

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Erythrina velutina Willd. alkaloids: Piecing biosynthesis together from transcriptome analysis and metabolite profiling of seeds and leaves

Abstract: Graphical abstract

Cited by 5 publications

References 78 publications

Non-target molecular network and putative genes of flavonoid biosynthesis in Erythrina velutina Willd., a Brazilian semiarid native woody plant

Non-target molecular network and putative genes of flavonoid biosynthesis in Erythrina velutina Willd., a Brazilian semiarid native woody plant

Combination of GC-MS Molecular Networking and Larvicidal Effect against Aedes aegypti for the Discovery of Bioactive Substances in Commercial Essential Oils

Transcriptome Analysis of Stephania tetrandra and Characterization of Norcoclaurine-6-O-Methyltransferase Involved in Benzylisoquinoline Alkaloid Biosynthesis

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