Biotransformation of ent -13- epi -manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi

Garcı́a-Granados, Andrés; Fernández, Antonia; Gutiérrez, Marı́a C.; Martı́nez, Antonio; Quirós, Raquel; Rivas, Francisco; Arias, J. M.

doi:10.1016/j.phytochem.2003.09.017

Cited by 17 publications

(13 citation statements)

References 31 publications

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“…28,29 With other filamentous fungi, regioselective oxidation of the hydroxy group has also been found in one of the hydroxy groups of entmanoyl oxides. 30,31 The reduction of the keto group in derivative 4, by action of a dehydrogenase present in R. miehei, would lead to compound 6 with the S-configuration for the 12-hydroxy derivative obtained (Figure 4). Most reductions carried out with yeasts and many microorganisms are consistent with Prelog's rule.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi

Basso

Nicotra

Parra³

et al. 2016

J. Nat. Prod.

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Incubation of salpichrolide A (1) with Rhizomucor miehei produced hydroxylation in rings B and C (C-7 and C-12) and led to C-5-C-6 epoxide opening, while incubation of salpichrolides C (2) and G (3) with R. miehei led to epoxide opening at the C-24-C-25 and C-5-C-6 positions, respectively. Biotransformation of salpichrolide A (1) with Cunninghamella elegans produced stereoselective hydroxylated, oxidized, and reduced derivatives in different positions of the A, B, and C rings and C-5-C-6 epoxide opening. In addition, selective epoxide opening at the C-5-C-6 or C-24-C-25 positions was obtained from the incubation of salpichrolide A (1) with Curvularia lunata.

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Section: Journal Of Natural Productsmentioning

confidence: 99%

Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi

Basso

Nicotra

Parra³

et al. 2016

J. Nat. Prod.

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“…The 12-keto derivative (103) of varodiol was biotransformed with F. moniliforme and R. nigricans [39]. F. moniliforme gave the previously isolated ent-7 -hydroxy derivative (106, 8%), together with an ent-7 ,11 -dyhydroxy derivative (111, 7%).…”

Section: Natural Ent-13-epi-manoyl Oxides and Analoguesmentioning

confidence: 99%

“…This diterpene was incubated with a culture of F. moniliforme [39], yielding two previously isolated metabolites: a 3-keto derivative (71, 16%) and an ent-7 -hydroxy derivative (53, 35%). The regioselective oxidation of varodiol (43) by F. moniliforme gave better yields for 71 (16%) than did biohydroxylation at C-12 of ribenone (61) by G. fujikuroi (6%) [34].…”

Section: Natural Ent-13-epi-manoyl Oxides and Analoguesmentioning

confidence: 99%

“…Incubation of varodione (119) with C. lunata [7d] and C. elegans [30] produced the same polar metabolite, isolated as acetyl derivative, as the result of a 14R,15-dihydroxylation (120, 21% and 11%, respectively). The incubation of the same substrate (119) with F. moniliforme [30] gave ent-11 -(121, 7%), ent-1 -(122, 9%), ent-7 ,11 -(123, 9%), ent-6 ,11 -hydroxylated metabolites (124, 1%), as well as an ent-6 ,12 -dihydroxy-11-oxo derivative (125, 1%), while G. roseum [39] gave rise to mono- hydroxylations only at C-1 (122, 19%) or C-7 (126, 7%), both by the ent-face. R. nigricans [39] yielded a metabolite hydroxylated at C-18 (127, 10%), as well as the ent-7 -hydroxy (126, 4%) and the epoxy derivatives (115, 5%; 116, 6%; 117, 13%; 118, 14%), previously isolated.…”

Section: Natural Ent-13-epi-manoyl Oxides and Analoguesmentioning

confidence: 99%

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Manoyl-Oxide Biotransformations with Filamentous Fungi

Garcı́a-Granados¹,

Martı́nez²,

Parra³

et al. 2007

COC

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Microbial transformations of manoyl oxides by filamentous fungi have been used to introduce hydroxyl groups, regio-and stereoselectively, into substrates at positions difficult to achieve by chemical means. The principal objective of most papers published in this field has been to produce new, highly oxygenated, bioactive manoyl-oxide compounds that present a large diversity of biological properties. The manoyl oxides most frequently studied at present are forskolin and its derivatives, the pharmacological activity of which is related to their ability to activate AC (adenylate cyclase), thus generating an increase in intracellular cAMP (cyclic adenosine monophosphate). The microbial hydroxylation of forskolin and 1,9-dideoxyforskolin has been extensively studied, using the fungi Scopuloriopsis sp., Syncephalastrum sp., Neurospora crassa, Mortierella isabellina and several Aspergillus sp.. Other biotransformation studies of natural manoyl oxides and hemi-synthetic enantio derivatives, carried out via the biomimetic cyclization of ent-8 -hydroxylabda-13(16),14-dienes, have used filamentous fungi Curvularia lunata, Cunninghamella elegans, Fusarium moniliforme, Gibberella fujikuroi, Gliocladium roseum, Mucor plumbeus, Rhizopus nigricans and Neurospora crassa. In some cases, the new hydroxylations were introduced at the same positions as in natural forskolin, yielding some noteworthy products that show biological activities.

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“…Biotransformation reactions show high chemo-, regio-and enantioselectivity, producing a wide variety of fine chemicals, such as, natural flavor (Schrader et al 2004;Berger 2009), pharmaceutical and agrochemical intermediaries (García-Granados et al 2004;Huisman and Gray 2002;Patel 2002;Stewart 2000).…”

Section: Introductionmentioning

confidence: 99%

Biotransformations of cinnamaldehyde, cinnamic acid and acetophenone with Mucor

Liu

Liang

et al. 2011

World J Microbiol Biotechnol

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A strain JX23 was isolated from soil and identified as a species of Mucor according to the morphological characteristics and the nuclear ribosomal internal transcribed spacer sequence and designated as Mucor sp. JX23. Biotransformations of cinnamaldehyde (CMD), cinnamic acid (CMA) and acetophenone (ACP) catalyzed by JX23 were investigated. After JX23 was cultured for 48 h, the substrates CMD, CMA and ACP were added to the growth medium respectively and the products were analyzed by GC-MS and HPLC. Mucor sp. JX23 exhibited considerable redox capability and different catalytic specificity to CMD, CMA and ACP. CMD was selectively hydrogenated to cinnamyl alcohol. CMA was biotransformed to ACP with a, b-oxidation like degradation, and ACP could not be reduced further by JX23. When ACP was added as substrate, it could be asymmetrically reduced to (S)-(-)-1-phenylethyl alcohol (S-PEA) with high stereoselectivity (90%). Further, the biotransformations of different binary mixture substrates with JX23 were also studied. The biocatalytic selectivity depended on the relationship between the binary mixtures in above-mentioned reaction.

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Biotransformation of ent -13- epi -manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi

Cited by 17 publications

References 31 publications

Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi

Biotransformation of Salpichrolides A, C, and G by Three Filamentous Fungi

Manoyl-Oxide Biotransformations with Filamentous Fungi

Biotransformations of cinnamaldehyde, cinnamic acid and acetophenone with Mucor

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