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Lupeol derivative as well as synthesis method and application thereof

A technology for lupin alcohol and derivatives, which is applied in the field of biosynthesis, can solve the problems of restricted drug screening, less oxidation sites of lupin alcohol parent nucleus, difficult chemical synthesis and the like

Pending Publication Date: 2021-04-13
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the lupeol nucleus not only has fewer available oxidation sites, but also is difficult to synthesize chemically, and there are few known oxidation-modified P450 enzymes and biocatalytic sites on the nucleus, which limits the research on drug screening and new drug development.

Method used

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  • Lupeol derivative as well as synthesis method and application thereof
  • Lupeol derivative as well as synthesis method and application thereof
  • Lupeol derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] This embodiment provides a method for synthesizing lupeol, and the specific operation is as follows.

[0082] In this embodiment, the second gene encoding lupeol synthase adopts GgLUS1 gene, the first gene encoding CYP450 enzyme is selected from: CYP51H10, CYP716A83 and CYP88D6; the third gene encoding CPR reductase is selected from: GgCPR1 and AaCPR .

[0083] (1) Acquisition of genes

[0084] Look up the nucleotide sequence required for the construction of recombinant organisms on NCBI, find the CDS sequence of the target sequence, and design the primers shown in Table 1. The primer includes a sequence of the candidate gene and a homology arm sequence on the yeast expression vector pESC-tHMGR-Ura or pESC-His or pESC-Leu, the lowercase letters indicate the homologous sequence of the vector, and the uppercase letters indicate the sequence of the gene.

[0085] Table 1 Primer Sequence

[0086]

[0087]

[0088] In Table 1, F is an upstream primer, and R is a dow...

Embodiment 2

[0136] This example provides a method for synthesizing lupeol derivatives. The general process refers to Example 1. The difference is that this example uses the CYP enzyme gene CYP716A83 to catalyze Lupeol. Specific reference Figure 17 In this study, three plasmids containing GgLUS1, CYP716A83 and GgCPR1 were co-transformed into Saccharomyces cerevisiae microbial hosts, and the yeast products after induced expression were isolated and detected. C-28 performed sequential catalytic oxidations and identified the two products of this combination as betulin and betulinic acid.

Embodiment 3

[0138]This example provides a method for synthesizing lupeol derivatives. The general process refers to Example 1. The difference is that this example uses CYP93E3 to catalyze Lupeol. Specific reference Figure 18 In this study, three plasmids containing GgLUS1, CYP93E3 and GgCPR1 were co-transformed into Saccharomyces cerevisiae microbial hosts, and the yeast products after induced expression were isolated and detected. Through the comparison of blank control standards, it was found that CYP93E3 inhibited Lupeol The oxidative modification was identified, and the product of this combination was deduced to be 24-Hydroxy-lupeol based on the known function of CYP93E3.

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Abstract

The invention discloses a lupeol derivative as well as a synthesis method and application thereof, and relates to the technical field of biosynthesis. According to the synthesis method, a new synthesis pathway is adopted, and CYP450 enzymes from different plant sources are used for modifying lupeol; and by expressing a gene for encoding lupeol synthetase, a gene for encoding CYP450 enzyme and a gene for encoding CPR reductase in exogenous microorganisms capable of generating 2, 3-squalene oxide, various novel lupeol derivatives can be obtained, and a foundation is laid for further development of the lupeol.

Description

technical field [0001] The invention relates to the technical field of biosynthesis, in particular to a lupe alcohol derivative and its synthesis method and application. Background technique [0002] As a kind of plant secondary metabolites, triterpenoids not only have important physiological significance to plants, but also attract much attention because of their wide range of pharmacological activities. Lupeol (Lupeol) is a basic skeleton in triterpenoids, and its C-28 derivative betulinic acid (Betulinic acid) has shown strong anti-tumor, anti-HIV, anti-inflammatory, anti-malarial in vitro and liver protection And other biological activities, and low toxicity, has great application prospects. [0003] However, due to the poor druggability of betulinic acid, low bioavailability and difficulty in structural modification, the further development and utilization of this compound are restricted; the core of lupeol is a 6-6-6-6-5 pentacyclic fused structure It is difficult to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12N15/81C12N15/61C12N15/53C12P33/00C07J63/00A61P35/00A61P29/00A61P31/12C12R1/865
CPCC12N15/81C12N15/52C12N9/90C12N9/0042C12N9/0071C12Y504/99041C12Y106/02004C12P33/00C07J63/008A61P35/00A61P29/00A61P31/12
Inventor 段礼新刘中秋熊文波李钰季爱加梁锦才
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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