Fungal hydroxylation of (−)-santonin and its analogues

Lamm, Andrew S.; Chen, Avril R.M.; Reynolds, William F.; Reese, Paul B.

doi:10.1016/j.molcatb.2008.11.004

Cited by 15 publications

(6 citation statements)

References 23 publications

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“…The characteristic 13 C shifts of C-6 and C-12 were similar to those of the already reported 6,7dehydrosantonin and 6-deoxy-2-hydroxydesmotroposantonin with ring-opened carboxylic acid moiety, respectively. [145] Furthermore, the 1 H and 13 C NMR data fitted perfectly those of the (7S,10S,11R)enantiomer, [86] excluding the (7S,10S,11S)-enantiomer as the product. [146] papaverine (4, C 20 H 21 NO 4 , white crystals, 39 mg, 33 %): 1 4'-desmethylpapaverine (18, C 19 H 19 NO 4 , white solid, 2 mg, 2 %): 1 H NMR (300 MHz, CDCl 3 ): δ = 8.36 (1H, d, J = 5.8 Hz, 3-H), 7.55 (1H, d, J = 5.8 Hz, 4-H), 7.43 (1H, s, 8-H), 7.10 (1H, s, 5-H), 6.94 (1H, br, 2'-H), 6.82 (2H, s, 5'-, 6'-H), 4.64 (2H, br, 10-H), 4.03 (3H, s, 6-Hs), 3.94 (3H, s, 7-Hs), 3.80 (3H, s, 3'-H).…”

Section: (+)-(4r5s7r11s)-mentioning

confidence: 63%

Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4

et al. 2021

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Efficient synthetic techniques for the diversification of natural products are incremental for drug discovery processes of the pharmaceutical industry because these complex bioactive compounds often require an adjustment of properties. Human liver P450 3A4, key player of the body's detoxification system and decisive factor of a drug's metabolic fate, is renowned for its broad substrate scope including many natural products. In this study, we investigated the synthetic potential of human P450 3A4 for the diversification of natural product classes and isolated the produced metabolites of six selected natural products at a preparative 100-mg scale. Aided by efficient expression levels in P. pastoris, this whole-cell biocatalyst was found to be highly effective at the intended job allowing the identification of a total of 31 authentic human metabolites, many of them for the first time. By revealing an unprecedented degree of diversification, this study extends the synthetic repertoire for efficient enzymatic natural product modification in a one-step fashion and adds a completely new view to an old enzyme traditionally used for inhibition and toxicology studies.

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Section: (+)-(4r5s7r11s)-mentioning

confidence: 63%

Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4

et al. 2021

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“…It is transformed by one strain of A. niger to 1,2-dihydro-␣-santonin [51] and by a different strain to 1-hydroxy-␣-santonin, 13-hydroxy-␣-santonin, 3,6,9-trihydroxy-9,10-seco-selina-1,3,5(10)-trien-12-oic acid-12,6-lactone (CVIII), and the photoproduct lumisantonin (CIX) [42]. Another strain, A. niger ATCC 9142, transforms (−)-␣-santonin (CVII) to 11␤-hydroxy-␣-santonin, 14-hydroxy-␣-santonin, and 3,6-dihydroxy-9-keto-9,10-seco-selina-1,3,5(10)-trien-12-oic acid-12,6-lactone (CX) [52]: Myli-4(15)-en-9-one (CXV) and myliol (CXVI), two sesquiterpenoids derived from a liverwort, are hydroxylated by A. niger IFO 4407 at the 12-methyl group [56]: Artemisia annua, the sweet wormwood, produces several sesquiterpenoids that have been used for experimental drugs. The tricyclic endoperoxide artemisitene (CXVIII, with positions numbered according to the scheme used by Parshikov et al [4]) is transformed by A. niger NRRL 599 to 9␣-artemisinin (CXIX), 7␤-hydroxydeoxy-9␣-artemisinin (CXX), and to 7␤-hydroxy-9␣-artemisinin (CXXI), which has antimalarial activity [ The important antimalarial drug artemisinin (CXXII) is transformed by A. niger AS 3.795 to 4␣-hydroxydeoxyartemisinin (CXXIII, yield 15% in 4 days [59]).…”

Section: Homentioning

confidence: 99%

The use of Aspergillus niger cultures for biotransformation of terpenoids

Parshikov

Sutherland

2014

Process Biochemistry

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“…Transformation of one of them, 3-amino-4-hydroxybenzenesulfonic acid (AHBS), by a laccase purified from Cerrena unicolor , resulted in the biosynthesis of a novel phenoxazinone dye [ 7 , 9 ]. The use of fungal cultures to transform various chemical compounds has already been reported in several studies [ 15 - 17 ] and fungal biomass immobilized on Scotch-Brite™[ 18 ], alginate beads [ 19 ], and stainless steel sponge [ 20 ] was utilized for decolouration of textile dyes. This is the first paper on the use of immobilized white rot fungal strains for synthesis of dyes.…”

Section: Introductionmentioning

confidence: 99%

Whole-cell fungal transformation of precursors into dyes

Polak

Jarosz-Wilkołazka

2010

Microb Cell Fact

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BackgroundChemical methods of producing dyes involve extreme temperatures and unsafe toxic compounds. Application of oxidizing enzymes obtained from fungal species, for example laccase, is an alternative to chemical synthesis of dyes. Laccase can be replaced by fungal biomass acting as a whole-cell biocatalyst with properties comparable to the isolated form of the enzyme. The application of the whole-cell system simplifies the transformation process and reduces the time required for its completion. In the present work, four fungal strains with a well-known ability to produce laccase were tested for oxidation of 17 phenolic and non-phenolic precursors into stable and non-toxic dyes.ResultsAn agar-plate screening test of the organic precursors was carried out using four fungal strains: Trametes versicolor, Fomes fomentarius, Abortiporus biennis, and Cerrena unicolor. Out of 17 precursors, nine were transformed into coloured substances in the presence of actively growing fungal mycelium. The immobilized fungal biomass catalyzed the transformation of 1 mM benzene and naphthalene derivatives in liquid cultures yielding stable and non-toxic products with good dyeing properties. The type of fungal strain had a large influence on the absorbance of the coloured products obtained after 48-hour transformation of the selected precursors, and the most effective was Fomes fomentarius (FF25). Whole-cell transformation of AHBS (3-amino-4-hydroxybenzenesulfonic acid) into a phenoxazinone dye was carried out in four different systems: in aqueous media comprising low amounts of carbon and nitrogen source, in buffer, and in distilled water.ConclusionsThis study demonstrated the ability of four fungal strains belonging to the ecological type of white rot fungi to transform precursors into dyes. This paper highlights the potential of fungal biomass for replacing isolated enzymes as a cheaper industrial-grade biocatalyst for the synthesis of dyes and other commercially important products. The use of immobilized fungal biomass limits free migration of cells and facilitates their reuse in a continuous system for precursor transformation.

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Fungal hydroxylation of (−)-santonin and its analogues

Cited by 15 publications

References 23 publications

Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4

Natural Product Diversification by One‐Step Biocatalysis using Human P450 3A4

The use of Aspergillus niger cultures for biotransformation of terpenoids

Whole-cell fungal transformation of precursors into dyes

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