Microbiological Transformation of Terpenes: Hydroxylation of α-Pinene

Bhattacharyya, P.; Prema, B. R.; Kulkarni, Bhaskar D.; Pradhan, Suresh K.

doi:10.1038/187689b0

Cited by 67 publications

(29 citation statements)

References 2 publications

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“…Transformation of -pinene to verbenols by microorganisms (fungi or bacteria) has been reported in the literature, [5][6][7][8][9][10][11] but not many examples exist of the use of plant cells for the conversion of -pinene. 3,12,13) The main transformation products have proved similar regardless of the plant cell or microorganism used for the different studies.…”

Section: Resultsmentioning

confidence: 99%

Formation oftrans-Verbenol and Verbenone from α-Pinene Catalysed by ImmobilisedPicea abiesCells

Vaněk

Halík

Vankova

et al. 2005

Bioscience, Biotechnology, and Biochemistry

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Both enantiomers and the racemate of -pinene were transformed by Picea abies cells immobilised on alginate. The main products were cis-and trans-verbenol, the later being further transformed to verbenone. The enantiomeric purity of each product more or less corresponded to that of the substrate. Transformation by free cells was faster than that by the immobilised cells. The ratio of products differed to some extent between the transformation by free and immobilised cells.

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Section: Resultsmentioning

confidence: 99%

Formation oftrans-Verbenol and Verbenone from α-Pinene Catalysed by ImmobilisedPicea abiesCells

Vaněk

Halík

Vankova

et al. 2005

Bioscience, Biotechnology, and Biochemistry

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“…For example, Bhattacharyya et al [29] reported that Aspergillus niger formed verbenone, cis-verbenol, and trans-sobrerol from α-pinene. Busmann and Berger [30] described verbenone and trans-verbenol, together with myrtenol and transpinocarveol, as major biotransformation products of α-pinene formed by basidiomycetes fungi.…”

Section: Pre-screening Experimentsmentioning

confidence: 98%

Microbial Oxidation of (-)-α-pinene to Verbenol Production by Newly Isolated Strains

Rottava¹,

Cortina

Zanella

et al. 2010

Appl Biochem Biotechnol

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Verbenol is a bicyclicbicycle secondary allylic alcohol, with pronounced camphor and mint flavor notes, mainly used as food flavoring. This compound is also used to control harmful insects, and hence has potential for using in agriculture, and is an intermediate in the synthesis of valuable perfume and medicinal substances. This work is focused on the microbial oxidation of (-)-α-pinene to verbenol production. To carry out the present study, 405 microorganisms were tested for their ability to bioconvert the substrate. From the isolated microorganisms, 193 were selected in the pre-screening using mineral medium for limonene degradation. At the screening step, 31 strains were able to convert (-)-α-pinene in verbenol. The highest concentration in verbenol from (-)-α-pinene was about 125.6 mg/L for yeast isolated from orange juice industrial residue.

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“…The responsible enzyme for the initial hydroxylation of camphor was later identified as CYP101A1 (P450 cam ) [16,17], the first described P450s of bacterial origin. Similarly, the oxidation of terpenes by fungi was reported in the same period with the discovery of α-pinene conversion into several oxygenated products by Aspergillus niger [18]. Further monoterpenoid substrates of different A. niger strains include, for instance, linalool and limonene [19,20].…”

Section: Origin and Identification Of Microbialmentioning

confidence: 95%

Terpene Hydroxylation with Microbial Cytochrome P450 Monooxygenases

Janocha

Schmitz

Bernhardt

2015

Biotechnology of Isoprenoids

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Terpenoids comprise a highly diverse group of natural products. In addition to their basic carbon skeleton, they differ from one another in their functional groups. Functional groups attached to the carbon skeleton are the basis of the terpenoids' diverse properties. Further modifications of terpene olefins include the introduction of acyl-, aryl-, or sugar moieties and usually start with oxidations catalyzed by cytochrome P450 monooxygenases (P450s, CYPs). P450s are ubiquitously distributed throughout nature, involved in essential biological pathways such as terpenoid biosynthesis as well as the tailoring of terpenoids and other natural products. Their ability to introduce oxygen into nonactivated C-H bonds is unique and makes P450s very attractive for applications in biotechnology. Especially in the field of terpene oxidation, biotransformation methods emerge as an attractive alternative to classical chemical synthesis. For this reason, microbial P450s depict a highly interesting target for protein engineering approaches in order to increase selectivity and activity, respectively. Microbial P450s have been described to convert industrial and pharmaceutically interesting terpenoids such as ionones, limone, valencene, resin acids, and triterpenes (including steroids) as well as vitamin D3. Highly selective and active mutants have been evolved by applying classical site-directed mutagenesis as well as directed evolution of proteins. As P450s usually depend on electron transfer proteins, mutagenesis has also been applied to improve the interactions between P450s and their respective redox partners. This chapter provides an overview of terpenoid hydroxylation reactions catalyzed by bacterial P450s and highlights the achievements made by protein engineering to establish productive hydroxylation processes.

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Microbiological Transformation of Terpenes: Hydroxylation of α-Pinene

Cited by 67 publications

References 2 publications

Formation oftrans-Verbenol and Verbenone from α-Pinene Catalysed by ImmobilisedPicea abiesCells

Formation oftrans-Verbenol and Verbenone from α-Pinene Catalysed by ImmobilisedPicea abiesCells

Microbial Oxidation of (-)-α-pinene to Verbenol Production by Newly Isolated Strains

Terpene Hydroxylation with Microbial Cytochrome P450 Monooxygenases

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