Biotransformation of linalool to furanoid and pyranoid linalool oxides by Aspergillus niger

Demyttenaere, Jan; Willemen, Hendra M.

doi:10.1016/s0031-9422(98)80066-6

Cited by 53 publications

(42 citation statements)

References 20 publications

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“…A similar distribution of products have been obtained with Aspergillus strains [8]. In GC-FID spectra, however, traces ( < 1%) of their precursor (i.e., 6,7-epoxylinalool) [7] were present. Together with the mixture of rearranged compounds 7 -10, some fungi (i.e., 2D7, 1F2, 1C5, and 1F9) furnished the 1-methyl-1-(4-methylpentyl)oxiranemethanol (6; 2 -45%), which was, however, the only product obtained with the fungus 1D15 (45%).…”

Section: Results Andsupporting

confidence: 77%

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Rueda

Guerrini

Giovannini

et al. 2013

Chemistry & Biodiversity

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The biotransformations of (RS)-linalool (1), (S)-citronellal (2), and sabinene (3) with fungi isolated from the epicarp of fruits of Citrus genus of the Amazonian forest (i.e., C. limon, C. aurantifolia, C. aurantium, and C. paradisiaca) are reported. The more active strains have been characterized, and they belong to the genus Penicillium and Fusarium. Different biotransformation products have been obtained depending on fungi and substrates. (RS)-Linalool (1) afforded the (E)- and (Z)-furanlinalool oxides (7 and 8, resp.; 39 and 37% yield, resp.) with Fusarium sp. (1D2), 6-methylhept-5-en-2-one (4; 49%) with F. fujikuroi, and 1-methyl-1-(4-methypentyl)oxiranemethanol (6; 42%) with F. concentricum. (S)-Citronellal (2) gave (S)-citronellol (12; 36-76%) and (S)-citronellic acid (11; 5-43%) with Fusarium species, while diastereoisomeric p-menthane-3,8-diols 13 and 14 (20 and 50% yield, resp.) were obtained as main products with Penicillium paxilli. Finally, both Fusarium species and P. paxilli biotransformed sabinene (3) to give mainly 4-terpineol (19; 23-56%), and (Z)- and (E)-sabinene hydrates (17 (3-21%) and 18 (11-17%), resp.).

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Section: Results Andsupporting

confidence: 77%

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Rueda

Guerrini

Giovannini

et al. 2013

Chemistry & Biodiversity

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“…Trans-furanoid linalool oxide was identified as the major product of biotransformation of (R)-linalool in Aspergillus niger [65] . Moreover, in fungus, biotransformation of linalool to furanoid and pyranoid linalool oxides was postulated to have epoxylinalool as an intermediate [66].…”

Section: Discussionmentioning

confidence: 99%

Integrated metabolome and transcriptome analysis of Magnolia champaca identifies biosynthetic pathways for floral volatile organic compounds

et al. 2017

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Background Magnolia champaca, commonly known as champak is a well-known tree due to its highly fragrant flowers. Champak floral scent is attributed to a complex mix of volatile organic compounds (VOCs). These aromatic flowers are widely used in flavors and fragrances industry. Despite its commercial importance, the VOC biosynthesis pathways in these flowers are largely unknown. Here, we combine metabolite and RNA sequencing (RNA-seq) analyses of fully opened champak flowers to discover the active VOC biosynthesis pathways as well as floral scent-related genes.ResultsVolatile collection by headspace method and analysis by gas chromatography-mass spectrometry (GC-MS) identified a total of 43 VOCs from fully opened champak flowers, of which 46.9% were terpenoids, 38.9% were volatile esters and 5.2% belonged to phenylpropanoids/benzenoids. Sequencing and de novo assembly of champak flower transcriptome yielded 47,688 non-redundant unigenes. Transcriptome assembly was validated using standard polymerase chain reaction (PCR) based approach for randomly selected unigenes. The detailed profiles of VOCs led to the discovery of pathways and genes involved in floral scent biosynthesis from RNA-seq data. Analysis of expression levels of many floral-scent biosynthesis-related unigenes in flowers and leaves showed that most of them were expressed higher in flowers than in leaf tissues. Moreover, our metabolite-guided transcriptomics, in vitro and in vivo enzyme assays and transgenic studies identified (R)-linalool synthase that is essential for the production of major VOCs of champak flowers, (R)-linalool and linalool oxides.ConclusionAs our study is the first report on transcriptome analysis of Magnolia champaca, this transcriptome dataset that serves as an important public information for functional genomics will not only facilitate better understanding of ecological functions of champak floral VOCs, but also provide biotechnological targets for sustainable production of champak floral scent.Electronic supplementary materialThe online version of this article (doi:10.1186/s12864-017-3846-8) contains supplementary material, which is available to authorized users.

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“…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]. Although there are indications that P450s are not involved in the transformation of limonene by A. niger, most microorganismmediated conversions of terpenes seem to proceed via cytochrome P450 monooxygenases.…”

Section: Origin and Identification Of Microbialmentioning

confidence: 93%

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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Biotransformation of linalool to furanoid and pyranoid linalool oxides by Aspergillus niger

Cited by 53 publications

References 20 publications

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Biotransformations of Terpenes by Fungi from Amazonian Citrus Plants

Integrated metabolome and transcriptome analysis of Magnolia champaca identifies biosynthetic pathways for floral volatile organic compounds

Terpene Hydroxylation with Microbial Cytochrome P450 Monooxygenases

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