Extraction and purification of limonene-1,2-diol obtained from the fungal biotransformation of limonene

Medeiros, Tiago Daniel Madureira de; Alexandrino, Thaís Dolfini; Pastore, Gláucia Maria; Bicas, Juliano Lemos

doi:10.1016/j.seppur.2020.117683

Cited by 18 publications

(7 citation statements)

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“…The biotransformation products presented a purity in CG of at least 96.7%, similar to previously published results, 10,20 reaching a purity level appropriated to NMR analysis. 25 Previous studies on the biotransformation of both R-(+)-and S-(À)-limonene by Rhodococcus erythropolis indicated that the original spatial configuration of the substrate (chiral carbon at Position 4) is retained in the products (limonene-1,2-diol), and the two hydroxyls 24 The same results were evidenced in the present study, that is, (+)-(1S,2S,4R)-limonene-1,2-diol produced by the biotransformation of R-(+)-limonene by C. nymphaeae and (À)-(1R,2R,4S)-limonene-1,2-diol produced by the biotransformation of S-(À)-limonene by F. oxysporum or C. nymphaeae (Figure 1), although different microorganisms were used and, at least for C. nymphaeae versus R. erythropolis, the enzymes involved in such biocatalysis were not the same.…”

Section: Discussionsupporting

confidence: 89%

“…The mobile phase was constituted by hexane (30 mL, F1), followed by hexane: ethyl acetate (10 mL, 1:1, v/v, F2), ethyl acetate (10 mL, v/v, F3), and ethanol (30 mL, F4). After organic solvent evaporation (under vacuum, at 45°C), 20 the F3 fraction was kept under refrigeration until spectroscopic (nuclear magnetic resonance [NMR]), chromatographic (gas chromatography [GC]), and biological evaluations.…”

Section: Methodsmentioning

confidence: 99%

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Structural properties and evaluation of the antiproliferative activity of limonene‐1,2‐diol obtained by the fungal biotransformation of R‐(+)‐ and S‐(−)‐limonene

et al. 2022

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Limonene‐1,2‐diol is a limonene oxygenated metabolite that possesses eight different stereoisomers, which could result in different biological properties. Nonetheless, the relation between its spatial configuration and biological function is still little explored. The present study aimed to perform the stereoisomers identification using nuclear magnetic resonance (NMR) investigation of the limonene‐1,2‐diol produced via R‐(+)‐ and S‐(−)‐limonene biotransformation by Colletotrichum nymphaeae and S‐(−)‐limonene biotransformation by Fusarium oxysporum 152B. Besides, in vitro antiproliferative activity was evaluated against human tumor and nontumor cell lines. The NMR analysis showed that R‐(+)‐limonene biotransformation afforded exclusively (+)‐(1S,2S,4R‐limonene‐1,2‐diol), whereas S‐(−)‐limonene biotransformation afforded exclusively (−)‐(1R,2R,4S‐limonene‐1,2‐diol) independent on the fungi used. Despite no significant cytostatic effects, a possible influence of stereogenic center on the antiproliferative activity of these limonene biotransformation products was evidenced. Moreover, the lack of in vitro antiproliferative effect of limonene‐1,2‐diol against nontumor cells suggested a safe dose range for further in vivo evaluations, including food applications.

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Section: Discussionsupporting

confidence: 89%

Section: Methodsmentioning

confidence: 99%

Structural properties and evaluation of the antiproliferative activity of limonene‐1,2‐diol obtained by the fungal biotransformation of R‐(+)‐ and S‐(−)‐limonene

et al. 2022

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“…Recently, a study investigated the extraction and puri cation of limonene-1,2-diol from biotransformation of R-(+)-limonene by C. nymphaeae CBMAI 0864. Results showed that aroma compounds concentrations followed a similar pro le to that observed for incubated both substrates, with an accumulated concentration of 2.65g/L -1 of Limonene-1,2-diol that was obtained after 192 h of biotransformation (Medeiros et al 2021). Table 1 summarizes the screening studies for limonene-1,2-diol production by fungal biotransformation of limonene enantiomers.…”

Section: Fungal Biotransformation Of Limonene For the Production Of Aroma Compoundsmentioning

confidence: 56%

Fungal biotransformation of limonene and pinene as a biotechnological approach for production of aroma compounds

Sevalho

Paulino

Souza

et al. 2021

Preprint

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The number of aroma compounds obtained by biotechnological process has increased tremendously in recent years and, as a result, are now being extensively employed in order to make products more attractive for consumers. In the present review, we inten to assess the wide range of reactions are catalyzed by fungal strains in regards to biotransformation of limonene and pinene for the aroma compounds production, their production rates/maximum concentrations and their biological potential. We comprehensively summarized in this review available data (2000–2021) regarding fungal biotransformation of limonene and pinene as biotechnological processes. Over the past years, has been paid to the biotransformation processes due to mild and environmentally friendly conditions applied. This review has shown that reports on the application of the fungi as a promising source of biocatalysts, mainly for stereoselective reactions such as hydroxylation and epoxidation. Studies have demonstrated the existence of promising monoterpenes used as substrates, which could be important from an industrial standpoint since this increases their importance as starting materials for obtaining aromatic molecules new. Moreover, biological (e.g.,antioxidant, anticancer) activities attributed to some monoterpene biotransformation products are increasingly being reported, indicating that their applications may transcend food, cosmetic and pharmaceutical industry.

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“…Taking multi‐stage extraction and separation of monoterpenes as an example, Medeiros et al. [27] have reported a liquid‐liquid extraction method for separating limonene‐1,2‐diol in fungal biotransformation media containing limonene as the main undesirable product. After media filtration, the supernatant was extracted in four steps by using two different solvents (hexane and ethyl acetate).…”

Section: Common Separation Methodsmentioning

confidence: 99%

Separation and purification of plant terpenoids from biotransformation

Chen

Pang

Luo

et al. 2021

Engineering in Life Sciences

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The production of plant terpenoids through biotransformation has undoubtedly become one of the research hotspots, and the continuous upgrading of the corresponding downstream technology is also particularly important. Downstream technology is the indispensable technical channel for the industrialization of plant terpenoids. How to efficiently separate high‐purity products from complex microbial fermentation broths or enzyme‐catalyzed reactions to achieve high separation rates, high returns and environmental friendliness has become the focus of research in recent years. This review mainly introduces the common separation methods of plant terpenoids based on biotransformation from the perspectives of engineering strain construction, unit separation technology, product properties and added value. Then, further attention was paid to the application prospects of intelligent cell factories and control in the separation of plant terpenoids. Finally, some current challenges and prospects are proposed, which provide possible directions and guidance for the separation and purification of terpenoids and even industrialization.

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Extraction and purification of limonene-1,2-diol obtained from the fungal biotransformation of limonene

Cited by 18 publications

References 28 publications

Structural properties and evaluation of the antiproliferative activity of limonene‐1,2‐diol obtained by the fungal biotransformation of R‐(+)‐ and S‐(−)‐limonene

Structural properties and evaluation of the antiproliferative activity of limonene‐1,2‐diol obtained by the fungal biotransformation of R‐(+)‐ and S‐(−)‐limonene

Fungal biotransformation of limonene and pinene as a biotechnological approach for production of aroma compounds

Separation and purification of plant terpenoids from biotransformation

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