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Keywords = ambradiol

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19 pages, 1491 KiB  
Article
Untargeted Metabolomics Exploration of the Growth Stage-Dependent Chemical Space of the Sclareol-Converting Biocatalyst Hyphozyma roseonigra
by Efficient N. Ncube, Lungile Sitole, Paul A. Steenkamp, Lucia H. Steenkamp and Ian A. Dubery
Catalysts 2022, 12(10), 1225; https://doi.org/10.3390/catal12101225 - 13 Oct 2022
Viewed by 2110
Abstract
Hyphozyma roseonigra is a dimorphic yeast used as a biocatalyst to convert sclareol, a plant diterpenoid to ambradiol. The latter is an intermediate in the synthesis of ambrafuran, a high-value chemical in the fragrance industry. Unfortunately, little is known about the underlying biochemistry [...] Read more.
Hyphozyma roseonigra is a dimorphic yeast used as a biocatalyst to convert sclareol, a plant diterpenoid to ambradiol. The latter is an intermediate in the synthesis of ambrafuran, a high-value chemical in the fragrance industry. Unfortunately, little is known about the underlying biochemistry of this microorganism. In this study, the integration of multi-platform-based metabolomics was used to better comprehend H. roseonigra from a biochemical perspective. The focus on metabolomic changes during growth and development was accomplished using untargeted LC–MS and NMR analyses. Cell suspensions were grown in batch culture over a 14-day period, and cells from the early-, log-, and stationary phases were harvested every second day using platform-compatible extraction procedures. Following chemometric analysis of LC–MS and NMR data acquired from both intra- and extracellular extracts, the identified discriminatory ions annotated from the endo- and exometabolomes (metabo-fingerprinting and metabo-footprinting) were found to fall predominantly in the primary metabolism class. Pathway mapping and feature-based network correlation analysis assisted in gaining insights into the active metabolic pathways during growth and development and did not flag terpene synthesis. This study provides novel insights into the basic metabolic capabilities of H. roseonigra and suggests that sclareol is metabolized as the detoxification of a hydrophobic xenobiotic compound. Full article
(This article belongs to the Special Issue Biocatalysis and Whole-Cell Biotransformation in Biomanufacturing)
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16 pages, 4203 KiB  
Article
Metabolomics-Guided Analysis of the Biocatalytic Conversion of Sclareol to Ambradiol by Hyphozyma roseoniger
by Efficient N. Ncube, Paul A. Steenkamp, Chris W. van der Westhuyzen, Lucia H. Steenkamp and Ian A. Dubery
Catalysts 2022, 12(1), 55; https://doi.org/10.3390/catal12010055 - 4 Jan 2022
Cited by 8 | Viewed by 3041
Abstract
The biocatalytic conversion of sclareol to ambradiol, a valuable component in the fragrance industry, using whole-cell biotransformation by the dimorphic yeast Hyphozyma roseoniger, was investigated using metabolomics tools. An integrated approach was used to identify and quantify the participating intermediates in this [...] Read more.
The biocatalytic conversion of sclareol to ambradiol, a valuable component in the fragrance industry, using whole-cell biotransformation by the dimorphic yeast Hyphozyma roseoniger, was investigated using metabolomics tools. An integrated approach was used to identify and quantify the participating intermediates in this bioconversion using both nuclear magnetic resonance (NMR) spectroscopy and liquid chromatography coupled to mass spectrometry (LC–MS). This study entailed growth stage-dependent analysis of H. roseoniger suspensions grown in batch culture over a 14-day period, beginning with a three-day induction period using 20 mg/200 mL sclareol, followed by a further 1 g/200 mL sclareol dose to enable ambradiol production. The progress of the bioconversion and the resulting dynamic changes to the metabolome were monitored using NMR analysis and semi-targeted LC–MS metabolomics. This outlined the molecular conversions occurring within the matrix and no novel intermediates participating in the sclareol to ambradiol conversion could be identified. This study presents new findings about the transformative capabilities of H. roseoniger as a whole cell biocatalyst, highlighting its potential utility in similar applications. Full article
(This article belongs to the Special Issue Biocatalysis and Whole-Cell Biotransformation in Biomanufacturing)
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13 pages, 5022 KiB  
Review
Ambrafuran (AmbroxTM) Synthesis from Natural Plant Product Precursors
by Efficient N. Ncube, Lucia Steenkamp and Ian A. Dubery
Molecules 2020, 25(17), 3851; https://doi.org/10.3390/molecules25173851 - 25 Aug 2020
Cited by 20 | Viewed by 7333
Abstract
Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components: 40–46% cholestanol type steroids and approximately 25–45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition [...] Read more.
Ambergris, an excretion product of sperm whales, has been a valued agent in the formulation of perfumes. The composition of ambergris consists of two major components: 40–46% cholestanol type steroids and approximately 25–45% of a triterpenoid known as ambrein. Ambergris undergoes oxidative decomposition in the environment to result in odorous compounds, such as ambraoxide, methylambraoxide, and ambracetal. Its oxidized form, ambrafuran (IUPAC name: 3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran), is a terpene furan with a pleasant odor and unique olfactive and fixative properties. The current state of the fragrance industry uses ambrafuran materials entirely from synthetic or semisynthetic sources. However, natural compounds with the potential to be converted to ambergris-like odorants have been extracted from several different types of plants. Here we review plant terpenoids suitable as starting materials for the semisyntheses of ambrafuran or intermediates, such as ambradiol, that can be used in biocatalytic transformations to yield ambrafuran. Full article
(This article belongs to the Section Natural Products Chemistry)
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