木质素的生物降解和生物利用

doi:10.12211/2096-8280.2023-062

合成生物学

• 特约评述 •

木质素的生物降解和生物利用

刘宽庆, 张以恒

中国科学院天津工业生物技术研究所体外合成中心，天津 300308

收稿日期:2023-08-28 修回日期:2023-11-01 出版日期:2023-11-02
通讯作者: 刘宽庆,张以恒
作者简介:刘宽庆（1984—），男，博士，中国科学院天津工业生物技术研究所研究员。2007年本科毕业于中国农业大学，2009年获得美国宾夕法尼亚州立大学硕士学位，2015年获得美国贝勒医学院博士学位。曾在美国德克萨斯大学西南医学中心从事博士后研究。主要研究方向为微生物生理代谢、核酸化学、蛋白合成调控。E-mail：liukq@tib.cas.cn
张以恒（1971—），男，博士，中国科学院天津工业生物技术研究所研究员，低碳合成工程生物学（全国）重点实验室主任，曾是美国弗吉尼亚理工大学终身正教授。1993年和1996年获得华东理工大学生物工程专业学士和硕士学位；2002年获得美国达特茅斯学院化学工程专业博士学位。主要研究方向为体外生物转化、体外合成生物学、生物制造、生物炼制和淀粉储能。 E-mail：xw_zhang@tib.cas.cn
基金资助:
科技部重点项目(2022YFC3401700);天津市合成生物技术创新能力提升行动创新人才/团队发展项目(TSBICIP-CXRC-068)

Biological degradation and utilization of lignin

Kuanqing LIU, Yiheng ZHANG

In Vitro Synthetic Biology Center，Tianjin Institute of Industrial Biotechnology，Chinese Academy of Sciences，Tianjin 300308，China

Received:2023-08-28 Revised:2023-11-01 Online:2023-11-02
Contact: Kuanqing LIU, Yiheng ZHANG

摘要/Abstract

摘要：

木质素是木质纤维素的一个主要成分，按干重计约占15%-30%，全球年产量在200亿吨。木质素是由苯丙烷单元通过多种不同的碳-碳和碳-氧键构成的一类芳香族高聚化合物，是高等陆生植物次生细胞壁的主要成分，赋予了植物的刚性和保护植物体免受微生物的入侵。由于木质素产量巨大、可再生，近些年全球对木质素利用的兴趣持续升高。但是木质素的成分复杂，无论是其降解还是后续的利用都充满了挑战，因此目前多用作燃料。在众多木质素降解利用的方法中，生物法反应条件温和、绿色环保，近些年在绿色可持续发展的大背景下受到广泛关注。本文首先总结了自然界中催化木质素降解的关键酶：漆酶、锰过氧化物酶、木质素过氧化物酶、染料脱色过氧化物酶、多功能过氧化物酶等，并简要介绍了其催化机制。其次，本文总结了生物利用木质素类芳香族化合物过程中涉及的四个主要反应：O-脱甲基、脱羧、羟基化和双加氧酶介导的开环反应，相关的酶和催化机制。最后，本文简要介绍了利用合成生物学手段构建细胞工厂实现木质素高值利用的案例。木质素的生物降解和利用是一个极具潜力的领域，但同时也存在诸多的挑战，例如转化效率低、反应时间长等。但本文作者相信随着合成生物学的迅猛发展，利用高效基因编辑和代谢工程改造提高关键酶的反应速率和代谢通路的效率、提高底盘细胞对有毒芳香族化合物的低抗能力、维持还原力的平衡等将有效提高木质素生物降解利用的效率，其工业应用也许在不久的将来就可能会实现。

关键词: 木质素, 生物降解, 生物利用

Abstract:

Lignin is a major component of lignocellulose, accounting for 15%-30% on a dry weight basis, with an annual yield estimated to be 20 billion tonnes. Lignin is a heterogenous aromatic polymer of phenylpropanoids linked by various C-C and C-O bonds. It is an integral component of the secondary cell wall from terrestrial plants, providing plants with rigidness and fending off microbial pathogens. The abundance and renewability of lignin has recently attracted ample interest in valorizing this readily available polymer. However, the complex nature of lignin presents a significant challenge for lignin breakdown and utilization, and at present the majority of lignin is simply burned as a fuel. Among the different methods, biological utilization of lignin has emerged as a highly attractive approach, since it proceeds under mild conditions and is generally considered environmentally friendly, especially considering that environmental sustainability is trending worldwide. This review comprises three major sections. First, we will summarize key enzymes that Nature has created to break down lignin, including laccase, manganese peroxidase, lignin peroxidase, dye-decolorizing peroxidase, and versatile peroxidase etc. Relevant enzymes and their catalytic mechanisms will also be briefly discussed. Second, we will review key reactions in priming and processing lignin derived aromatics before they enter microbial metabolic pathways: O-demethylation, hydroxylation, decarboxylation, and ring opening, as well as representative enzymes and their catalytic mechanisms. Finally, we will present engineering efforts toward biological valorization of lignin and lignin derived aromatics, which is largely driven by synthetic biology approaches. Biological valorization of lignin is undoubtedly a field full of potential, however its realization still faces several major hurdles, such as low conversion efficiency and long processing time. Nevertheless, as synthetic biology is developing rapidly, harnessing the power of genetic and metabolic engineering to improve the efficiency of lignin breakdown and utilization, microbial tolerance to toxic aromatics, and redox balance will certainly be a promising path forward, paving the way for industrial application in the near future.

Key words: lignin, biological degradation, biological utilization

中图分类号:

Q819

刘宽庆, 张以恒. 木质素的生物降解和生物利用[J]. 合成生物学, DOI: 10.12211/2096-8280.2023-062.

Kuanqing LIU, Yiheng ZHANG. Biological degradation and utilization of lignin[J]. Synthetic Biology Journal, DOI: 10.12211/2096-8280.2023-062.

图/表 6

图1 木质素的成分和利用

Fig. 1 Composition and application of lignin

表1 具有木质素降解能力的微生物列表

Table 1 List of lignin degrading microbes

真菌	信息来源	细菌	信息来源
Aspergillus flavus	[34]	Acinetobacter sp.	[33]
Aspergillus terreus	[33]	Amycolatopsis sp.	[33]
Bjerkandera	[34]	Aneurinibacillus aneurinilyticus	[33]
Ceriporiopsis subvermispora	[34]	Arthrobacter globiformis	[33]
Cyathus stercoreus	[34]	Bacillus atrophaeus	[33-34]
Dichomitus squalens	[33]	Bacillus pumilus	[34]
Fusarium oxysporum	[33]	Cupriavidus necator	[33]
Gloeophyllum trabeum	[34]	Enterobacter lignolyticus	[33]
Lepista nuda	[33]	Klebsiella pneumoniae	[33]
Penicillium citrinum	[33]	Mycobacterium smegmatis	[34]
Perenniporia medulla-panis	[34]	Nocardia autotrophica	[33]
Phanerochaete chrysosporium	[33-34]	Oceanimonas doudoroffii	[33]
Phlebia radiata	[34]	Ochrobactrum tritici	[33]
Pleurotus eryngii	[34]	Pantoea ananatis	[34]
Pleurotus ostreatus	[34]	Pseudomonas putida	[33-34]
Porodaedalea pini	[34]	Rhodococcus erythropolis	[33]
Pycnoporus cinnabarinus	[34]	Rhodococcus jostii	[33-34]
Schizophyllum commune	[33]	Sphingomonas paucimobilis	[33-34]
Serpula lacrymans	[33-34]	Streptomyces coelicolor	[33]
Trametes versicolor	[34]	Streptomyces viridosporus	[33-34]
Tramtes hirsute	[34]
Wolfiporia cocos	[34]

图2 自然界木质素降解涉及的主要酶反应

图3 自然界利用木质素类芳香族化合物所涉及的酶反应及其进入微生物代谢途径的示意图（O-脱甲基化、羟基化、脱羧和开环反应主要参考了Erickson 等［12］和Vaillancourt等［53］。木质素类芳香族化合物进入微生物代谢途径展示了丁香酸（syringate）和儿茶酚（catechol）。代谢途径中的酶并非一定来自同一微生物：DesA［54］和LigM［55］来自少动鞘氨醇单胞菌（Sphingomonas paucimobilis SYK-6），Dmts［12］来自Novosphingobium aromaticivorans DSM12444，GalA，B，C，D［56-57］、CatB［58］、CatC［58］、PcaI［59］、PcaJ［59］、以及PcaF ［59-61］来自恶臭假单胞菌，CatA［62］来自贝氏不动杆菌（Acinetobacter baylyi），PcaD［63］来自浑浊红球菌（Rhodococcus opacus）1CP，PaaJ ［64］来自大肠杆菌（Escherichia coli）。）

Fig. 3 Primary reactions for utilizing lignin derived aromatics and schematic of assimilating syringate and catechol into microbial metabolic pathways(Enzymatic reactions are mainly based off Erickson et al.[12] and Vaillancourt et al.[53]. Enzymes for assimilating lignin into microbial metabolic pathways may not come from the same species: DesA[54] and LigM[55] from Sphingomonas paucimobilis SYK-6, Dmts[12] from Novosphingobium aromaticivorans DSM 12444, GalA, B, C, D[56-57], CatB[58], CatC[58], PcaI[59], PcaJ[59], and PcaF[59-61] from Pseudomonas putida, CatA[62] from Acinetobacter baylyi, PcaD[63] from Rhodococcus opacus 1CP, and PaaJ [64] from Escherichia coli.)

表2 生物法转化木质素（类芳香族化合物）生产高值产品

Table 2 Valorization of lignin and its derived aromatics

底物	产物	底盘细胞	参考文献
异丁香酚、丁香酚、香草醇、阿魏酸	香兰素	Bacillus pumilus Escherichia coli	[83-84]
苯甲酸、4-羟基肉桂酸、木质素	丙酮酸、乳酸、琥珀酸、衣康酸、酮己二酸	Phanerochaete chrysosporium Pseudomonas putida	[85-88]
香兰素、香草酸、苯甲酸、儿茶酚	顺,顺-己二烯二酸	Arthrobacter sp. Brevibacterium flavum Corynebacterium acetoacidophilum Corynebacterium glutamicum Corynebacterium lilium Corynebacterium pseudodiphtheriticum Pseudomonas sp. Pseudomonas putida Sphingobacterium sp.	[89-101]
儿茶酚	聚对苯二甲酸乙二醇酯	Pseudomonas putida	[102]
木质素	脂质	Rhodococcus opacus	[103-106]
木质素	聚羟基烷酯	Cupriavidus basilensis Pandoraea sp. Pseudomonas putida	[107-110]

图4 构建木质素降解利用微生物的策略

Fig. 4 Engineering strategies for microbial degradation and utilization of lignin

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木质素的生物降解和生物利用

Biological degradation and utilization of lignin

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