New derivatives of the iridoid specioside from fungal biotransformation

Cassemiro, Nadla Soares; Sanches, Luana Bonifácio; Kato, Natália Naomi; Ruller, Roberto; Carollo, Carlos Alexandre; Mello, João Carlos Palazzo de; Anjos, Edson dos Santos dos; Silva, Denise Brentan

doi:10.1007/s00253-021-11504-7

Cited by 5 publications

(3 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The overaccumulation of metabolites in yeast may cause metabolic or environmental stress-related problems 26 , 46 . To survive in complex environments, some self-protection mechanisms have evolved, such as the secretion of secondary metabolites by efflux pumps 47 . Here, because the secondary metabolites rubusoside was secreted out of the cell by an unknown active efflux mechanism (Fig.…”

Section: Discussionmentioning

confidence: 99%

De novo biosynthesis of rubusoside and rebaudiosides in engineered yeasts

Wang

Zhang

et al. 2022

Nat Commun

View full text Add to dashboard Cite

High-sugar diet causes health problems, many of which can be addressed with the use of sugar substitutes. Rubusoside and rebaudiosides are interesting molecules, considered the next generation of sugar substitutes due to their low-calorie, superior sweetness and organoleptic properties. However, their low abundance in nature makes the traditional plant extraction process neither economical nor environmental-friendly. Here we engineer baker’s yeast Saccharomyces cerevisiae as a chassis for the de novo production of rubusoside and rebaudiosides. In this process, we identify multiple issues that limit the production, including rate-liming steps, product stress on cellular fitness and unbalanced metabolic networks. We carry out a systematic engineering strategy to solve these issues, which produces rubusoside and rebaudiosides at titers of 1368.6 mg/L and 132.7 mg/L, respectively. The rubusoside chassis strain here constructed paves the way towards a sustainable, large-scale fermentation-based manufacturing of diverse rebaudiosides.

show abstract

Section: Discussionmentioning

confidence: 99%

De novo biosynthesis of rubusoside and rebaudiosides in engineered yeasts

Wang

Zhang

et al. 2022

Nat Commun

View full text Add to dashboard Cite

show abstract

“…Microbial biotransformation is simpler and more efficient than chemical synthesis [ 25 , 26 ]. Bacteria and fungi have highly specific enzyme systems that can produce specific structural modifications such as glycosylation, succination, isopentenylation, and other modifications [ 27 ]. Highly efficient enzymatic biotransformation can be carried out in nonaqueous systems by organic solvent-resistant bacterial strains.…”

Section: Discussionmentioning

confidence: 99%

Efficient Synthesis and In Vitro Hypoglycemic Activity of Rare Apigenin Glycosylation Derivatives

Zhao¹,

Pei²,

Zhang³

et al. 2023

Molecules

View full text Add to dashboard Cite

Apigenin is a natural flavonoid with significant biological activity, but poor solubility in water and low bioavailability limits its use in the food and pharmaceutical industries. In this paper, apigenin-7-O-β-(6″-O)-d-glucoside (AG) and apigenin-7-O-β-(6″-O-succinyl)-d-glucoside (SAG), rare apigenin glycosyl and succinyl derivatives formed by the organic solvent-tolerant bacteria Bacillus licheniformis WNJ02 were used in a 10.0% DMSO (v/v) system. The water solubility of SAG was 174 times that of apigenin, which solved the application problem. In the biotransformation reaction, the conversion rate of apigenin (1.0 g/L) was 100% at 24 h, and the yield of SAG was 94.2%. Molecular docking showed that the hypoglycemic activity of apigenin, apigenin-7-glucosides (AG), and SAG was mediated by binding with amino acids of α-glucosidase. The molecular docking results were verified by an in vitro anti-α-glucosidase assay and glucose consumption assay of active compounds. SAG had significant anti-α-glucosidase activity, with an IC50 of 0.485 mM and enhanced glucose consumption in HepG2 cells, which make it an excellent α-glucosidase inhibitor.

show abstract

“…5MP2F4 ( Figure S1, Supporting Information ) was isolated in May 2019 from leaves of Bromelia balansae Mez (Bromeliaceae), a bromeliad species occurring in the ironstone outcrops of the Pantanal biome in Brazil. The fungal strain was identified according to morphological traits and ITS rDNA sequence analysis, as reported by Cassemiro et al [ 13 ]. The sequence data were submitted to GenBank with accession n° OP879817.…”

Section: Methodsmentioning

confidence: 99%

Metabolomic Strategies to Improve Chemical Information from OSMAC Studies of Endophytic Fungi

et al. 2023

Self Cite

View full text Add to dashboard Cite

Metabolomics strategies are important tools to get holistic chemical information from a system, but they are scarcely applied to endophytic fungi to understand their chemical profiles of biosynthesized metabolites. Here Penicillium sp. was cultured using One Strain Many Compounds (OSMAC) conditions as a model system to demonstrate how this strategy can help in understanding metabolic profiles and determining bioactive metabolites with the application of metabolomics and statistical analyses, as well as molecular networking. Penicillium sp. was fermented in different culture media and the crude extracts from mycelial biomass (CEm) and broth (CEb) were obtained, evaluated against bacterial strains (Staphylococcus aureus and Pseudomonas aeruginosa), and the metabolomic profiles by LC-DAD-MS were obtained and chemometrics statistical analyses were applied. The CEm and CEb extracts presented different chemical profiles and antibacterial activities; the highest activities observed were against S. aureus from CEm (MIC = 16, 64, and 128 µg/mL). The antibacterial properties from the extracts were impacted for culture media from which the strain was fermented. From the Volcano plot analysis, it was possible to determine statistically the most relevant features for the antibacterial activity, which were also confirmed from biplots of PCA as strong features for the bioactive extracts. These compounds included 75 (13-oxoverruculogen isomer), 78 (austalide P acid), 87 (austalide L or W), 88 (helvamide), 92 (viridicatumtoxin A), 96 (austalide P), 101 (dihydroaustalide K), 106 (austalide k), 110 (spirohexaline), and 112 (pre-viridicatumtoxin). Thus, these features included diketopiperazines, meroterpenoids, and polyketides, such as indole alkaloids, austalides, and viridicatumtoxin A, a rare tetracycline.

show abstract

New derivatives of the iridoid specioside from fungal biotransformation

Cited by 5 publications

References 41 publications

De novo biosynthesis of rubusoside and rebaudiosides in engineered yeasts

De novo biosynthesis of rubusoside and rebaudiosides in engineered yeasts

Efficient Synthesis and In Vitro Hypoglycemic Activity of Rare Apigenin Glycosylation Derivatives

Metabolomic Strategies to Improve Chemical Information from OSMAC Studies of Endophytic Fungi

Contact Info

Product

Resources

About