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通过大肠杆菌代谢工程从木质素衍生的肉桂酸高效生物合成松脂素。

Efficient biosynthesis of pinosylvin from lignin-derived cinnamic acid by metabolic engineering of Escherichia coli.

作者信息

Hu Yueli, Zhang Chen, Zou Lihua, Zheng Zhaojuan, Ouyang Jia

机构信息

Jiangsu Co-Innovation Centre of Efficient Processing and Utilization of Forest Resources, Nanjing Forestry University, Nanjing, 210037, People's Republic of China.

College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, People's Republic of China.

出版信息

Biotechnol Biofuels Bioprod. 2022 Dec 12;15(1):136. doi: 10.1186/s13068-022-02236-5.

DOI:10.1186/s13068-022-02236-5
PMID:36503554
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9743564/
Abstract

BACKGROUND

The conversion of lignin-derived aromatic monomers into valuable chemicals has promising potential to improve the economic competitiveness of biomass biorefineries. Pinosylvin is an attractive pharmaceutical with multiple promising biological activities.

RESULTS

Herein, Escherichia coli was engineered to convert the lignin-derived standard model monomer cinnamic acid into pinosylvin by introducing two novel enzymes from the wood plant: stilbene synthase from Pinus pinea (PpSTS) and 4-Coumarate-CoA ligase from Populus trichocarpa (Ptr4CL4). The expression of Ptr4CL4 drastically improved the production of pinosylvin (42.5 ± 1.1 mg/L), achieving values 15.7-fold higher than that of Ptr4CL5 (another 4-Coumarate-CoA ligase from Populus trichocarpa) in the absence of cerulenin. By adjusting the expression strategy, the optimized engineered strain produced pinosylvin at 153.7 ± 2.2 mg/L with an extremely high yield of 1.20 ± 0.02 mg/mg cinnamic acid in the presence of cerulenin, which is 83.9% ± 1.17 of the theoretical yield. This is the highest reported pinosylvin yield directly from cinnamic acid to date.

CONCLUSION

Our work highlights the feasibility of microbial production of pinosylvin from cinnamic acid and paves the way for converting lignin-related aromatics to valuable chemicals.

摘要

背景

将木质素衍生的芳香单体转化为有价值的化学品,对于提高生物质生物精炼厂的经济竞争力具有广阔的潜力。松白木素是一种具有多种潜在生物活性的有吸引力的药物。

结果

在此,通过引入来自木本植物的两种新酶,对大肠杆菌进行工程改造,使其将木质素衍生的标准模型单体肉桂酸转化为松白木素:来自欧洲赤松的芪合酶(PpSTS)和来自毛果杨的4-香豆酸辅酶A连接酶(Ptr4CL4)。Ptr4CL4的表达显著提高了松白木素的产量(42.5±1.1毫克/升),在没有浅蓝菌素的情况下,其产量比Ptr4CL5(来自毛果杨的另一种4-香豆酸辅酶A连接酶)高15.7倍。通过调整表达策略,优化后的工程菌株在浅蓝菌素存在的情况下,以153.7±2.2毫克/升的产量生产松白木素,肉桂酸的产率极高,为1.20±0.02毫克/毫克,达到理论产率的83.9%±1.17%。这是迄今为止报道的直接从肉桂酸生产松白木素的最高产量。

结论

我们的工作突出了从肉桂酸微生物生产松白木素的可行性,并为将木质素相关芳烃转化为有价值的化学品铺平了道路。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/8c9cbb387330/13068_2022_2236_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/ce084d085043/13068_2022_2236_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/69b11d4f9f06/13068_2022_2236_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/afbf58b4f13b/13068_2022_2236_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/08da70295804/13068_2022_2236_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/f26f75250adc/13068_2022_2236_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/8c9cbb387330/13068_2022_2236_Fig6_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/ce084d085043/13068_2022_2236_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/69b11d4f9f06/13068_2022_2236_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/afbf58b4f13b/13068_2022_2236_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/08da70295804/13068_2022_2236_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/f26f75250adc/13068_2022_2236_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f088/9743564/8c9cbb387330/13068_2022_2236_Fig6_HTML.jpg

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2
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Plants (Basel). 2022 Jun 9;11(12):1541. doi: 10.3390/plants11121541.
3
Enhanced production of pinosylvin stilbene with aging of Pinus strobus callus and nematicidal activity of callus extracts against pinewood nematodes.
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Sci Rep. 2022 Jan 14;12(1):770. doi: 10.1038/s41598-022-04843-6.
4
Microbial assimilation of lignin-derived aromatic compounds and conversion to value-added products.微生物对木质素衍生芳香族化合物的同化作用及转化为高附加值产品的过程。
Curr Opin Microbiol. 2022 Feb;65:64-72. doi: 10.1016/j.mib.2021.10.014. Epub 2021 Nov 11.
5
Construction of a p-coumaric and ferulic acid auto-regulatory system in Pseudomonas putida KT2440 for protocatechuate production from lignin-derived aromatics.在恶臭假单胞菌 KT2440 中构建对香豆酸和阿魏酸的自动调节系统,以从木质素衍生芳烃生产原儿茶酸。
Bioresour Technol. 2022 Jan;344(Pt B):126221. doi: 10.1016/j.biortech.2021.126221. Epub 2021 Oct 30.
6
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J Agric Food Chem. 2021 Oct 13;69(40):11804-11815. doi: 10.1021/acs.jafc.1c03087. Epub 2021 Oct 1.
7
A Computational Metabolic Model for Engineered Production of Resveratrol in .用于白藜芦醇工程化生产的计算代谢模型。
ACS Synth Biol. 2021 Aug 20;10(8):1992-2001. doi: 10.1021/acssynbio.1c00163. Epub 2021 Jul 8.
8
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