Synthesis method of terpenoid and glycosylation products thereof in synthesis route of mogrol

Abstract

The invention discloses a microbial fermentation method for synthesizing triterpene compounds, namely a distillers yeast recombination strain SY2 containing cucurbitane dienol synthetase SgCbQ, P450 CYP87D18 and cytochrome reductase CPR, in the metabolism route of mogrol, which takes dextrose as a substrate to synthesize three new products including 11-oxygen-cucurbitane dienol, 11-hydroxy-cucurbitane dienol and 11-oxygen-24, 25-epoxy-cucurbitane dienol. The invention further discloses a metabolism route for synthesizing mogrol through cucurbitane dienol, namely the cucurbitane dienol is catalyzed through P450 CYP87D18 and synthesized into 11-oxygen-cucurbitane dienol, 11-oxygen-cucurbitane dienol is catalyzed through enzyme and synthesized into 11-hydroxy-cucurbitane dienol and 11-oxygen-24, 25-epoxy-cucurbitane dienol, and 11-hydroxy-cucurbitane dienol and 11-oxygen-24, 25-epoxy-cucurbitane dienol can be synthesized into the mogrol through other P450 or epoxide hydrolase. The invention further discloses a novel thought for obtaining more glycosylation products by catalyzing new products through glycosyl transferase. The method has significance for determining the synthesis route of mogrol and synthesizing relevant intermediate metabolites and glycosylation products through the microbial fermentation method.

Description

technical field [0001] The invention relates to the field of biotechnology, in particular to a method for synthesizing three terpenoid compounds and their glycosylation products in the mogrosanol synthesis pathway. That is, using recombinant Saccharomyces cerevisiae strains containing cucurbitane dienol synthase and cytochrome P450, using glucose as a substrate to synthesize three terpenoids, these three terpenoids were identified by mass spectrometry and NMR as 11-hydroxy-cucurbit Alkadienol, 11-oxo-cucurbitadienol, 11-oxo-24,25-epoxy-cucurbitadienol; these three terpenoids are further glycosylated to produce a variety of glycosylated products . Background technique [0002] Mangosteen ( Siraitia grosvenorii ) is a precious medicinal plant unique to my country, mainly distributed in the Guangxi region of my country. from Siraitia grosvenorii. Molecules. 2014.19: 3669-3680), has been included in the first batch of "list of homologous varieties of medicine and food" by th...

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Problems solved by technology

At present, the synthesis pathways of cucurbitanedienol through 2,3-oxidized squalene and mogroside through glycosylation of mogrosinol have been relatively clear, and related enzymes have been reported. For example, the use of sugar derived from Arabidopsis Functional characterization of cucurbitadienol synthase and triterpene glycosyltransferase involved in biosynthesis of mogrosides from Siraitia grosvenorii. Plant and Cell Physiology. 2015. Yaoquan Liu , Jung Yeop Lee, Monika Khare. Methods and materials for enzymatic synthesis of mogroside compounds. US 20140308698 A1.); However, there are few reports on the cytochrome P450 that catalyzes the synthesis of mogroside compounds from cucurbitane dienol. Alcohol needs to be hydroxylated or oxidized at C-11, and hydroxylated at C-24 and C-25 to obtain mogrosanol. It has been reported that a possible synthetic route for synthesizing mogrosanol from cucurbitanedienol has not been accurately verified (Yaoquan Liu, Jorgen Hansen, Jens Houghton-larsen, Muthuswamy Panchapagesa Murali, Sathish Kumar, Nina Nicoline Rasmussen. Methods and materials for biosynthesis of mogroside compounds. US 20150064743 A1)

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