Oxidative functionalization of a halimane diterpenoid achieved by fungal transformation

Monteiro, A. F. M.; Righetto, Gabriela Marinho; Simões, Laura Vilar; Almeida, Larissa Costa de; Costa-Lotufo, Letı́cia V.; Camargo, Ilana Lopes Baratella da Cunha; Castro‐Gamboa, Ian

doi:10.1016/j.bioorg.2019.02.021

Cited by 3 publications

(4 citation statements)

References 24 publications

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“…The assay was conducted essentially as described by Monteiro et al . 34 . The HCT-116 and MCF-7 cells (1 × 10 4 cells well −1 ) were seeded in 96-well plates and, after 24 h, different concentrations (5 µM and 50 µM) of the compounds were added and incubated for 72 h. Doxorubicin (0.003 to 10 µM) and DMSO (0.5%) were used as a positive and negative controls, respectively.…”

Section: Methodsmentioning

confidence: 99%

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Medina

Araújo

Batista

et al. 2019

Sci Rep

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A chemical study of the EtOAc extract of Nemania bipapillata (AT-05), an endophytic fungus isolated from the marine red alga Asparagopsis taxiformis - Falkenbergia stage, led to the isolation of five new botryane sesquiterpenes, including the diastereomeric pair (+)-(2 R ,4 S ,5 R ,8 S )-( 1 ) and (+)-(2 R ,4 R ,5 R ,8 S )-4-deacetyl-5-hydroxy-botryenalol ( 2 ), (+)-(2 R ,4 S ,5 R ,8 R )-4-deacetyl-botryenalol ( 3 ), one pair of diastereomeric botryane nor sesquiterpenes bearing an unprecedented degraded carbon skeleton, (+)-(2 R ,4 R ,8 R )-( 4 ) and (+)-(2 R ,4 S ,8 S )-( 5 ), which were named nemenonediol A and nemenonediol B, respectively, in addition to the known 4β-acetoxy-9β,10β,15α-trihydroxyprobotrydial ( 6 ). Their structures were elucidated using 1D and 2D NMR, HRESIMS and comparison with literature data of similar known compounds. The absolute configurations of 2 , 3 and 4 were deduced by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, while those of 1 and 5 were assigned from vibrational circular dichroism (VCD) data. Compound 4 weakly inhibited acetylcholinesterase, whereas compound 1 inhibited both acetylcholinesterase and butyrylcholinesterase. Compounds 1 , 3 , 5 and 6 were tested against two carcinoma cell lines (MCF-7 and HCT-116), but showed no significant citotoxicity at tested concentrations (IC 50 > 50 µM).

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Section: Methodsmentioning

confidence: 99%

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Medina

Araújo

Batista

et al. 2019

Sci Rep

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“…Seven derivatives from diterpene (86) were identified, including four previously known compounds (92-95) (Monteiro et al, 2017) and three new compounds (89,90,91). Compound 86 presented a moderate reduction of a biofilm generated by Staphylococcus epidermidis ATCC35984, being this effect also observed in 91 and 95 (Monteiro et al, 2019). These studies led to the conclusion that important structural modifications, such as oxidations of inactive carbon sp 3 , yielded analogous compounds with new reactive sites, showcasing the capacity of endophytic fungi to serve as versatile catalysts for a wide variety of reactions.…”

Section: Natural Products From Microorganismsmentioning

confidence: 73%

“…Another line of research explored in NuBBE is the biotransformation method, which uses endophytic fungi to carry out chemical modifications in compounds (Zhang et al, 2021). Studies conducted with three different fungi strains demonstrated the feasibility of obtaining labdane (85) and halimane (86) derivatives (Monteiro et al, 2017;Monteiro et al, 2019) (Figure 6). The incubation of diterpene 85 (0.2 mg/mL) with Fusarium oxysporum resulted in the production of 7α-hydroxylabdane (87).…”

Section: Natural Products From Microorganismsmentioning

confidence: 99%

Twenty-five years of natural products research in NuBBE

Mannochio-Russo,

Pires dos Santos,

Bueno

et al. 2023

Front. Nat. Prod.

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The richness of Brazilian biodiversity translates into a valuable collection of molecules with biological properties that range from ecological functions to pharmacological properties. For over 25 years, the Nucleus of Bioassays, Biosynthesis, and Ecophysiology of Natural Products (NuBBE) has conducted extensive investigations into the chemical entities of numerous plant and microorganism species, resulting in the discovery of over a thousand natural compounds spanning various chemical classes (such as shikimate derivatives, phenylpropanoids, terpenoids, alkaloids, and peptides). The research goals within the natural products field encompass phytochemical studies, investigations of endophytic fungi and marine organisms, biosynthetic studies, medicinal chemistry, and the development of innovative methodologies. This comprehensive review article aims to offer valuable insights into the multifaceted research endeavors conducted in NuBBE. In this way, accomplishments, perspectives, and opportunities for advancing natural products research in Brazil are highlighted, seeking to inspire and motivate other research groups in the field of natural products–especially those located in emerging countries with rich biodiversity.

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“…Microorganisms and their enzymes have proven to be versatile biocatalysts and are extensively used for biotransformations of various terpenoids (Chatterjee & Bhattacharyya, 2001). Biocatalysis has been shown to have more potential advantages over traditional synthesis methods in the past decades as an alternative method (Monteiro et al., 2019). These biochemical reactions usually have high regional and stereospecificity (Parshikov & Sutherland, 2015).…”

Section: Introductionmentioning

confidence: 99%

Catalytic condition optimization in the conversion of nootkatone from valencene byYarrowia lipolytica

Xiao

Ren

Fan

et al. 2021

J. Food Process. Preserv.

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Yarrowia lipolytica was a widespread and promising object in biotechnology, which was used to increase the biotransformation of valencene into nootkatone in shake flasks in this study. The main objective of this work is to determine the optimum combination of transformation conditions in shake flasks on the basis of single factor process optimization experiment. The results showed that Y. lipolytica was cultured in medium for 36 hr (exponential phase) and the amount of added Y. lipolytica was 5% (v/v). The concentration of substrate valencene was 920 mg·L−1, and the transformation time was 36 hr after adding substrates. Dimethyl sulfoxide, a water‐soluble organic solvent, was used as a co‐solvent with a concentration of 0.8% (v/v). The maximum production of nootkatone was 628.41 ± 18.60 mg·L−1 and the conversion rate was 68.30 ± 2.02% at cultivation conditions of 32°C, 150 rpm, and PH 5.30. The results showed that optimizing the catalytic conditions can significantly increase the yield of nootkatone by Y. lipolytica. Practical applications Recently, natural nootkatone is increasingly important due to its flavoring and physiological effects, but the amount of nootkatone in plants is low and cannot meet the demand. Also, there were few studies about microbial transformation of valencene by Yarrowia lipolytica under certain catalytic conditions. We demonstrated that optimizing the catalytic conditions can significantly increase the yield of nootkatone. Therefore, it provides a basis for the subsequent use of genetic engineering to transform Y. lipolytica to produce nootkatone.

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Oxidative functionalization of a halimane diterpenoid achieved by fungal transformation

Cited by 3 publications

References 24 publications

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Botryane terpenoids produced by Nemania bipapillata, an endophytic fungus isolated from red alga Asparagopsis taxiformis - Falkenbergia stage

Twenty-five years of natural products research in NuBBE

Catalytic condition optimization in the conversion of nootkatone from valencene byYarrowia lipolytica

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