植物中苯并噁嗪类化合物的研究进展

doi:10.13560/j.cnki.biotech.bull.1985.2024-0497

摘要/Abstract

摘要：

植物次生代谢物作为调节生长发育的调节剂和防御物质重要组成部分，其化合物种类是极其复杂的。苯并噁嗪类化合物（benzoxazinoids, BXs）作为生物碱家族的次生代谢物之一，具有天然植物活性物质成分，被应用在药物成分和食品添加剂等领域，其药理和保健作用已成为新的研究热点。当前，有关BXs化合物研究都集中在禾本科玉米和小麦中，其调节机制研究还不够深入。本文从BXs化合物的组成、分类及代谢途径，详细介绍了其次生代谢过程，进化特征表明其存在特有生物合成簇结构。归纳总结了BXs化合物在植物生长发育中扮演着防御作用，包括对昆虫的防御作用、微生物的相互作用和竞争植物的化感作用。并且BXs作为信号分子介导植物对金属离子螯合、响应外界环境刺激和参与植物激素的调节剂，揭示了BXs化合物在植物与环境条件相互作用中的重要功能。同时，总结出BXs化合物目前研究所面临的问题及解决办法，相信随着BXs化合物的深入研究必将有力地促进新型农业生产和可持续战略实践的发展，有助于深入挖掘其潜在应用价值，解决当前农林业生产面临的多重挑战。

关键词: 苯并噁嗪, 次生代谢, 生物合成, 防御作用, 化感作用, 信号分子

Abstract:

Plant secondary metabolites are important components of regulators and defense substances that regulate growth and development, and their compound types are extremely complex. Benzoxazinoids (BXs), as one of the secondary metabolites of the alkaloid family, have natural plant active ingredients and are used in the fields of pharmaceutical ingredients and food additives. Their pharmacological and health effects have become a new research hotspot. At present, the study on BXs compounds is concentrated on gramineae corn and wheat, and the research on their regulatory mechanisms is not in-depth enough. In this paper, the secondary metabolic process of BXs compounds is introduced in detail from the composition, classification and metabolic pathways. The evolutionary characteristics indicate that they have a unique biosynthetic cluster structure. It is summarized that BXs compounds play a defensive role in plant growth and development, including defense against insects, microbial interactions and allelopathy in competing plants. Moreover, BXs serve as signaling molecules that mediate plant chelation of metal ions, respond to external environmental stimuli and participate in the regulators of plant hormones, revealing the important function of BXs compounds in the interaction between plants and environmental conditions. Concurrently, it summarizes the issues and solutions faced by BXs compounds in the current research. It is believed that with the in-depth research of BXs compounds, it will surely promote the development of new agricultural production and sustainable strategic practices, help to deeply explore their potential application value, and solve the multiple challenges facing current agricultural and forestry production.

Key words: benzoxazinoids, secondary metabolism, biosynthesis, defense, allelopathy, signaling molecule

李晓明, 尚秀华, 王有霜, 吴志华. 植物中苯并噁嗪类化合物的研究进展[J]. 生物技术通报, 2025, 41(4): 9-20.

LI Xiao-ming, SHANG Xiu-hua, WANG You-shuang, WU Zhi-hua. Research Progress in Benzoxazinoids in Plants[J]. Biotechnology Bulletin, 2025, 41(4): 9-20.

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分类 Classification		缩写 Abbreviation	化学全称 Chemical name
分类 Classification		缩写 Abbreviation	化学全称 Chemical name	R1		R2	R3
苯并噁嗪酮	异羟肟酸	DIBOA	2，4-二羟基-1，4苯并噁嗪-3-酮	H	H		H
Benzoxaziones		DIMBOA	2，4-二羟基-7-甲氧基-1，4苯并噁嗪-4-酮	H	OCH₃		H
		TRIBOA	2，4，7-三羟基-1，4苯并噁嗪-3-酮	H	OH		H
		TRIMBOA	2，4，7-三羟基-8-甲氧基-1，4苯并噁嗪-3-酮	H	OH		OCH₃
		DIM₂BOA	2，4-二羟基-7，8-二甲氧基-1，4苯并噁嗪-3-酮	H	OCH₃		OCH₃
	内酰胺	HBOA	2-羟基-2H-1，4-苯并噁嗪-3（4H）-酮	H	H		H
		DHBOA	2，7-二羟基-1，4-苯并噁嗪-3-酮	H	OH		H
		HMBOA	2-羟基-7-甲氧基-2H-1，4-苯并噁嗪-3（4H）-酮	H	OCH₃		H
		HM₂BOA	2-羟基-6，7-二甲氧基-2H-1，4-苯并噁嗪-3（4H）-酮	H	OCH₃		OCH₃
	甲基肟酸	HDMBOA	2-羟基-4，7-二甲氧基-1，4-苯并噁嗪-3-酮	H	OCH₃		H
	甲基肟酸	HDM₂BOA	2-羟基-4，7，8-三甲氧基-1，4-苯并噁嗪-3-酮	H	OCH₃		OCH₃
苯并噁嗪唑啉酮 Benzoxazolinones		BOA	2-苯并噁唑啉-2（3H）酮	H	H		H
		MBOA	6-甲氧基-苯并噁唑啉-2-酮	H	OCH₃		H
		M₂BOA	2-羟基-2H-1，4-苯并噁嗪-3（4）酮	H	OCH₃		OCH₃

分类 Classification		缩写 Abbreviation	化学全称 Chemical name
分类 Classification		缩写 Abbreviation	化学全称 Chemical name	R1		R2	R3
苯并噁嗪酮	异羟肟酸	DIBOA	2，4-二羟基-1，4苯并噁嗪-3-酮	H	H		H
Benzoxaziones		DIMBOA	2，4-二羟基-7-甲氧基-1，4苯并噁嗪-4-酮	H	OCH₃		H
		TRIBOA	2，4，7-三羟基-1，4苯并噁嗪-3-酮	H	OH		H
		TRIMBOA	2，4，7-三羟基-8-甲氧基-1，4苯并噁嗪-3-酮	H	OH		OCH₃
		DIM₂BOA	2，4-二羟基-7，8-二甲氧基-1，4苯并噁嗪-3-酮	H	OCH₃		OCH₃
	内酰胺	HBOA	2-羟基-2H-1，4-苯并噁嗪-3（4H）-酮	H	H		H
		DHBOA	2，7-二羟基-1，4-苯并噁嗪-3-酮	H	OH		H
		HMBOA	2-羟基-7-甲氧基-2H-1，4-苯并噁嗪-3（4H）-酮	H	OCH₃		H
		HM₂BOA	2-羟基-6，7-二甲氧基-2H-1，4-苯并噁嗪-3（4H）-酮	H	OCH₃		OCH₃
	甲基肟酸	HDMBOA	2-羟基-4，7-二甲氧基-1，4-苯并噁嗪-3-酮	H	OCH₃		H
	甲基肟酸	HDM₂BOA	2-羟基-4，7，8-三甲氧基-1，4-苯并噁嗪-3-酮	H	OCH₃		OCH₃
苯并噁嗪唑啉酮 Benzoxazolinones		BOA	2-苯并噁唑啉-2（3H）酮	H	H		H
		MBOA	6-甲氧基-苯并噁唑啉-2-酮	H	OCH₃		H
		M₂BOA	2-羟基-2H-1，4-苯并噁嗪-3（4）酮	H	OCH₃		OCH₃

基因 Gene	定位 Location	编码酶 Encoding enzyme	生化功能 Biochemical function
BX1	叶绿体	吲哚-3-甘油磷酸裂解酶	Indole-3-glycerophosphate→Indole
BX2	内质网	细胞色素P450单加氧酶CYP71C4	Indole→DIBOA
BX3	内质网	细胞色素P450单加氧酶CYP71C2
BX4	内质网	细胞色素P450单加氧酶CYP71C1
BX5	内质网	细胞色素P450单加氧酶CYP71C3
BX6	细胞质	2-酮戊二酸依赖型双加氧酶	GDIBOA→GTRIBOA
BX7	细胞质	O-甲基转移酶	GTRI（M）BOA→GDIMBOA/GDIM₂BOA
BX8	液泡	UDP-葡萄糖基转移酶	DIBOA→GDIBOA
BX9	液泡	UDP-葡萄糖基转移酶	DIBOA→GDIBOA
BX10	细胞质	O-甲基转移酶	GDIMBOA→GHDMBOA
BX11	细胞质	O-甲基转移酶
BX12	细胞质	O-甲基转移酶
BX13	细胞质	2-酮戊二酸依赖型双加氧酶	GDIMBOA→GTRIMBOA
BX14	细胞质	O-甲基转移酶	GDIM₂BOA→GHDM₂BOA

基因 Gene	定位 Location	编码酶 Encoding enzyme	生化功能 Biochemical function
BX1	叶绿体	吲哚-3-甘油磷酸裂解酶	Indole-3-glycerophosphate→Indole
BX2	内质网	细胞色素P450单加氧酶CYP71C4	Indole→DIBOA
BX3	内质网	细胞色素P450单加氧酶CYP71C2
BX4	内质网	细胞色素P450单加氧酶CYP71C1
BX5	内质网	细胞色素P450单加氧酶CYP71C3
BX6	细胞质	2-酮戊二酸依赖型双加氧酶	GDIBOA→GTRIBOA
BX7	细胞质	O-甲基转移酶	GTRI（M）BOA→GDIMBOA/GDIM₂BOA
BX8	液泡	UDP-葡萄糖基转移酶	DIBOA→GDIBOA
BX9	液泡	UDP-葡萄糖基转移酶	DIBOA→GDIBOA
BX10	细胞质	O-甲基转移酶	GDIMBOA→GHDMBOA
BX11	细胞质	O-甲基转移酶
BX12	细胞质	O-甲基转移酶
BX13	细胞质	2-酮戊二酸依赖型双加氧酶	GDIMBOA→GTRIMBOA
BX14	细胞质	O-甲基转移酶	GDIM₂BOA→GHDM₂BOA

序号 Serial No.	昆虫 Insect	功能描述 Functional description	参考 Reference
1	蚜虫	利用蚜虫侵染玉米自交系后转录和代谢水平均发生显著变化，其中ZmBX1、ZmBX2和ZmBX6基因的突变增加了蚜虫的繁殖	［38］［39］
2	玉米螟虫	玉米中4个转录因子ZmWRKY75、ZmMYB61、ZmNAC35和ZmGRAS37的表达与ZmBX1的表达模式相关，可能解释蚜虫侵染后苯并噁嗪类水平的变化；叶片摄食抗性与羟肟酸浓度呈正相关，DIMBOA具有与羟肟酸浓度相当的摄食威慑作用，影响幼虫神经系统酶和解毒酶的活性；西南玉米螟的抗性与HDMBOA的存在相关，对饲料中的幼虫具有毒性作用； DIMBOA和MBOA均增加了幼虫的死亡率和化蛹的发育时间，且与浓度水平呈正相关	［40-41］［42］［43］
3	甜菜夜蛾	甜菜夜蛾侵染玉米后基因表达和代谢图谱在1 h内发生迅速改变，ZmBX1和ZmBX2的突变显著改善了幼虫的生长	［44］
4	斜纹夜蛾	经过DIMBOA预处理的幼虫对各类杀虫剂产生高抗性，转录组分析发现解毒酶对斜纹夜蛾基因表达发挥重要作用	［45］
5	玉米根虫	玉米根中施加DIMBOA会增加玉米根虫的死亡率，根系BXs含量与抗毒性呈显著正相关	［46］
6	玉米线虫	玉米根中BXs化合物的浓度与线虫序列读数的相对丰度呈负相关，但与线虫类群之间存在正相关	［47］
7	草地贪夜蛾	草地贪夜蛾通过UDP-葡萄糖基转移酶进行立体选择性重新葡萄糖基化，对DIMBOA进行解毒； UGT33和UGT40参与苯并噁嗪的糖基化，并参与对草地贪夜蛾幼虫的解毒；模拟草地贪夜蛾取食后BXs含量增加，启动子和共表达分析表明，转录因子ZmbHLH57与ZmWRKY34调控系统叶片中的BXs生物合成基因	［48］［49］［50］
8	小麦球茎蝇	MBOA对幼虫的吸引呈剂量依赖性，并可能促进分泌物活性，而DIMBOA引起的反应较弱，因为土壤中MBOA比DIMBOA更稳定	［51］