Rearrangement and oxidation of β-amyrin promoted by growing cells of <i>Lecanicillium muscarinium</i>

Martins, Leonardo Ribeiro; Takahashi, Jacqueline A.

doi:10.1080/14786410903262865

Cited by 13 publications

(3 citation statements)

References 23 publications

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“…For instance, a monoterpene commonly targeted is limonene, due to its wide availability from cheap sources such as waste from the orange juice industry and its great potential as a substrate for the production of fragrances [4]. Functionalized derivatives of sesquiterpenes [5,6] and triterpenes [7] have also been obtained as fungal metabolites. Reports on the biotransformation of many different types of diterpenes, such as labdane [8], trachylobane [9,10], stemodane [11], aphidicolane [12], pimaradiene [13], abietane [14], taxane [15], atisane [16], and beyerane [17] are also very frequently found in the literature.…”

Section: Introductionmentioning

confidence: 99%

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

et al. 2014

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Abstract:The use of biotransformations in organic chemistry is widespread, with highlights of interesting applications in the functionalization of natural products containing unactivated carbons, like the kaurane diterpenes. A number of compounds with kaurane skeletons can be isolated in large amounts from several plant species and a myriad of biological activities has been related to these compounds. Studies on structure versus activity have showed that, in most cases, in kaurane diterpenes, activity increases with the increase of functionalization. Since naturally occurring kaurane diterpenes usually have limited functional groups to be used as targets for semi-synthetic modifications, production of more polar derivatives from kaurane diterpenes have been achieved mostly through the use of fungal biotransformations. In this review, selected examples the wonderful chemical diversity produced by fungi in kaurane diterpenes is presented. This diversity includes mainly hydroxylation of nearly all carbon atoms of the kaurane molecule, many of them carried out stereoselectively, as well as ring rearrangements, among other chemical modifications. Sources of starting materials, general biotransformation protocols employed, OPEN ACCESSMolecules 2014, 19 1857 fungi with most consistent regioselectivity towards kaurane skeleton, as well as biological activities associated with starting materials and products are also described.

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Section: Introductionmentioning

confidence: 99%

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

et al. 2014

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“…On the other hand, biotransformation can be made in aqueous medium, it operate in mild conditions and products with greater enantioselectivity and regioselectivity have been obtained (Perkins et al, 2016). Thus, biotransformation can be considered a useful tool to produce new compounds in ecologically friendly conditions (Vasconcelos et al, 2015) and unusual reactions in classical synthesis can be made (Martins and Takahashi, 2010).…”

Section: Introductionmentioning

confidence: 99%

Bioreduction of α,β-unsaturated carbonyl compounds by Lasiodiplodia pseudotheobromae, endophytic fungus from Morinda citrifolia (RUBIACEAE)

Silva

Anjos

Oliveira

et al. 2020

RSD

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Biotransformations are reactions carried out by microorganisms that lead to changes in the structures of organic compounds, among the biotransformations there are bioreductions. Bioreductions are of great interest to the pharmaceutical and food industries, as they almost always lead to the formation of enantiomerically pure compounds. Thus, this work aimed to verify the ability of the fungus Lasiodiplodia pseudotheobromae in bioreduce α,β-unsaturated carbonyl compounds. Compounds (3E)-4-(2-methoxy-phenyl)-but-3-en-2-one (1), (1E, 4E)-1,5-diphenyl-pent-1,4-dien-3-one (2) and (1E, 4E)-1,5-bis-(2-methoxy-phenyl)-penta-1,4-dien-3-one (3) were used as substrates. The reactions were carried out on an orbital shaker for 8 days at room temperature. The products formed were characterized by analytical thin layer chromatography (ATLC), high performance liquid chromatography (HPLC) and hydrogen nuclear magnetic resonance (1H NMR). For all products formed was observed reduction in double bonds C=C and C=O leading to the formation of the respective alcohols. This is the first report of biotransformation reactions using the fungus Lasiodiplodia pseudotheobromae.

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“…52 The triterpene β-amyrin 34 was also oxidised in the allylic position to give 3β-hydroxyolean-12en-11-one and an unusual rearrangement product, 11α,12αepoxytaraxerol. 53 Di-isophorone 35 was also oxidised in the allylic position to give 8β-hydroxydi-isophorone. 54…”

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confidence: 99%

Microbiological Hydroxylations with Cephalosporium Aphidicola

Hanson

2018

Journal of Chemical Research

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Rearrangement and oxidation of β-amyrin promoted by growing cells of Lecanicillium muscarinium

Cited by 13 publications

References 23 publications

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

The Remarkable Structural Diversity Achieved in ent-Kaurane Diterpenes by Fungal Biotransformations

Bioreduction of α,β-unsaturated carbonyl compounds by Lasiodiplodia pseudotheobromae, endophytic fungus from Morinda citrifolia (RUBIACEAE)

Microbiological Hydroxylations with Cephalosporium Aphidicola

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