皂荚与野皂荚刺中次生代谢物的差异

doi:10.11707/j.1001-7488.20220409

摘要/Abstract

摘要：

目的: 皂刺中的许多次生代谢物是药用活性成分。本文旨在探究皂荚与野皂荚刺的差异次生代谢物及进行差异代谢途径富集分析，为皂刺功能性化合物分离鉴定以及研究开发提供理论依据。方法: 以皂荚和野皂荚的1年生棘刺为材料，用UPLC-MS/MS检测平台和自建数据库MWDB4.0进行代谢组分析。结果: 1) 2个种的皂刺中共检测到457种次生代谢物，分为酚酸、生物碱、萜类、黄酮、木脂素、香豆素、鞣质类、其他8大类，酚酸和黄酮占比较大；2)野皂荚刺与皂荚刺相比，共有213种显著差异代谢物，其中121种物质在野皂荚刺中含量较高，包括55种酚酸，54种黄酮，5种木脂素和香豆素，4种生物碱，2种萜类，1种其他；92种物质在皂荚刺中含量较高，包括21种酚酸，19种黄酮，14种鞣质，14种生物碱，8种木脂素和香豆素，16种其他。3)皂荚刺中特有的代谢物有22种，异牡荆素-2″-O-鼠李糖苷、N,N′-二阿魏酰腐胺、香叶木素-8-C-(2″-O-鼠李糖基)葡萄糖苷、紫檀芪、原花青素C2相对含量较高，野皂荚刺中特有的代谢物有27种，松柏苷、5-O-咖啡酰莽草酸、槲皮素-3-O-(2″-对香豆酰)葡萄糖苷的相对含量较高。4)差异代谢物的代谢途径分析表明“茋类、二芳基庚烷类和姜酚的生物合成”途径中显著差异代谢物富集显著，苯丙烷生物合成和类黄酮代谢的差异代谢物富集较多。结论: 皂荚和野皂荚刺中共检测到457种次生代谢物；差异代谢物质主要是黄酮和酚酸类；茋类、二芳基庚烷类和姜酚的生物合成的差异代谢物显著富集(P < 0.05)，苯丙烷生物合成和黄酮类生物合成的差异代谢物富集较多。

关键词: 皂荚, 野皂荚, 皂刺, 代谢组, 差异代谢物, 通路富集分析

Abstract:

Objective: Many secondary metabolites in spina gleditsiae are medicinal active ingredients. This article aims to investigate the differential secondary metabolites in spines of Gleditsia sinensis and Gleditsia microphylla,and analyze the enrichment of the differential metabolic pathway,so as to provide a theoretical basis for the separation and identification of functional compounds from spina gleditsiae and for the research and development of functional compounds. Method: The 1-year-old spines of G. sinensis and G. microphylla were used as materials,the UPLC-MS/MS detection platform was used to determine secondary metabolites,and self-built database MWDB4.0 was used for metabonomic analysis. Results: 1) A total of 457 secondary metabolites were detected in the two species of spina gleditsiae,which were divided into 8 categories: phenolic acids,alkaloids,terpenes,flavonoids,lignans,coumarins,tannins,and others. Among them,phenolic acids and flavonoids accounted for a relatively large proportion; 2) There were significant differences in 213 metabolites in the spines between G. sinensis and G. Microphylla, of which the contents of 121 substances were higher in G. microphylla spines,including 55 phenolic acids and 54 flavonoids,5 kinds of lignans and coumarins,4 alkaloids,2 terpenes,and 1 other substance; The contents of 92 substances in G. microphylla were lower,including 21 phenolic acids,19 flavonoids,14 tannins,14 alkaloids,8 kinds of lignans and coumarins,16 others. 3) There were 22 kinds of unique metabolites in G. sinensis spines, of which isovitexin-2″-O-rhamnoside,N,N′-Diferuloylputrescine,diosmetin-8-C-(2″-O-rhamnosyl) glucoside,pterostilbene,and procyanidin C2 had relatively higher content. There were 27 unique metabolites in G. microphylla spines,of which the relative content of coniferin,5-O-Caffeoylshikimic acid,and quercetin-3-O-(2″-p-Coumaroyl) glucoside was relatively higher. 4) Metabolic pathway analysis of differential metabolites showed that the significantly differential metabolites in the pathways of "stilbene,diarylheptanes and gingerol biosynthesis" were significantly enriched,and the differential metabolites of phenylpropane biosynthesis and flavonoid metabolism were more enriched. Conclusion: There are 457 secondary metabolites detected in G. sinensis spines and G. microphylla spines. The differential metabolites are mainly concentrated in flavonoids and phenolic acids. The stilbenoid,diarylheptanoid and gingerol biosynthesis are significantly enriched in differential metabolites (P < 0.05),and the metabolites of phenylpropanoid biosynthesis and flavonoid biosynthesis are more enriched.

Key words: Gleditsia sinensis, Gleditsia microphylla, spina gleditsiae, metabolome, differential metabolites, pathway enrichment analysis

中图分类号:

S793.9

耿瑜欣,李红姣,郑建伟,张芹,于丽娜,李佳秋,李保会. 皂荚与野皂荚刺中次生代谢物的差异[J]. 林业科学, 2022, 58(4): 82-94.

Yuxin Geng,Hongjiao Li,Jianwei Zheng,Qin Zhang,Lina Yu,Jiaqiu Li,Baohui Li. Difference of Secondary Metabolites in Spines of Gleditsia sinensis and Gleditsia microphylla[J]. Scientia Silvae Sinicae, 2022, 58(4): 82-94.

图/表 11

图1

图2

图3

图4

图5

表1

皂荚和野皂荚刺差异表达代谢物"

序号 No.	物质 Compounds	分类 Classification	差异倍数 log₂FC
1	松柏苷Coniferin	酚酸Phenolic acid	19.41
2	5-O-咖啡酰莽草酸5-O-Caffeoylshikimic acid	酚酸Phenolic acid	17.65
3	槲皮素-3-O-(2″-对香豆酰)葡萄糖苷Quercetin-3-O-(2″-p-coumaroyl)glucoside	黄酮醇Flavonols	17.62
4	1-羟基松脂醇-1-O-葡萄糖苷1-Hydroxypinoresinol-1-O-glucoside	木脂素Lignans	16.23
5	金圣草黄素-7-O-(6″-阿魏酰)葡萄糖苷Chrysoeriol-7-O-(6″-feruloyl)glucoside	黄酮Flavonoid	15.93
6	苜蓿酸-3-O-葡萄糖醛酸苷-28-O-鼠李糖基(1, 2)-阿拉伯糖苷 Medicagenic acid-3-O-glucuronide-28-O-rhamnosyl(1, 2)-arabinoside	三萜皂苷 Triterpene saponin	15.56
7	4-O-(6′-O-葡萄糖基咖啡酰)-4-羟基苯甲酸4-O-(6′-O-glucosylcaffeoyl)-4-hydroxybenzoic acid	酚酸Phenolic acid	15.18
8	咖啡酰对香豆酰酒石酸Caffeoyl-p-coumaroyltartaric acid	酚酸Phenolic acid	15
9	异杞柳苷-6″-O-对香豆酸Isosalipurposide-6″-O-p-coumaric acid	查耳酮Chalcones	14.33
10	3, 5-二咖啡酰奎宁酸3, 5-Dicaffeoylquinic acid	酚酸Phenolic acid	14.27
……	……	……	……
204	白皮杉醇Piceatannol	茋类Stilbene	-14.84
205	黄颜木素Fustin	二氢黄酮醇Dihydroflavonol	-15.49
206	槟榔鞣质B1 Arecatannin B1	鞣质Tannin	-15.78
207	东莨菪内酯Scopoletin	香豆素Coumarins	-16.33
208	N-对香豆酰-N′-阿魏酰基腐胺N-p-coumaroyl-N′-feruloylputrescine	酚胺Phenolamine	-16.71
209	原花青素C2 Procyanidin C2	原花青素Proanthocyanidins	-16.79
210	紫檀芪Pterostilbene	茋类Stilbene	-17.34
211	香叶木素-8-C-(2″-O-鼠李糖基)葡萄糖苷Diosmetin-8-C-(2″-O-rhamnosyl)glucoside	黄酮碳糖苷 Flavonoid carbonoside	-17.9
212	N, N′-二阿魏酰腐胺N, N′-Diferuloylputrescine	酚胺Phenolamine	-19.39
213	异牡荆素-2″-O-鼠李糖苷Isovitexin-2″-O-rhamnoside	黄酮碳糖苷 Flavonoid carbonoside	-20.32

表1

图6

图7

图8

野皂荚刺特有代谢物的相对含量 1：云杉苷Picein；2：柚皮素-4′, 7-二甲醚Naringenin-4′, 7-dimethyl ether；3：5-O-咖啡酰莽草酸5-O-caffeoylshikimic acid；4：松柏苷Coniferin；5：咖啡酰对羟基苯甲酰酒石酸Caffeoyl(p-hydroxybenzoyl)tartaric acid；6: 咖啡酰对香豆酰酒石酸Caffeoyl-p-coumaroyltartaric acid；7：6-O-葡萄糖基-阿魏酰苯甲酸6-O-glucosyl-feruloylbenzoic acid；8：4-O-(6′-O-葡萄糖基咖啡酰)-4-羟基苯甲酸4-O-(6′-O-glucosylcaffeoyl)-4-hydroxybenzoic acid；9：洋丁香苷A Syringalide A；10：4-对香豆酰鼠李糖基-(1→6)-D-葡萄糖4-p-cumaroyl-rhamnosyl-(1→6)-D-glucose；11：3, 4-二没食子酰莽草酸3, 4-digalloylshikimic acid；12：4-O-(6′-O-葡萄糖基咖啡酰)-3, 4-二羟基苯甲酸4-O-(6′-O-glucosylcaffeoyl)-3, 4-dihydroxybenzoic acid；13：4-O-(6′-O-葡萄糖基-阿魏酰)-3, 4-二羟基苄醇4-O-(6′-O-glucosylferuloyl)-3, 4-dihydroxybenzyl alcohol；14：1′-O-(3, 4-二羟基苯乙基)-O-咖啡酰基-葡萄糖苷1′-O-(3, 4-dihydroxyphenethyl)-O-caffeoyl-glucoside；15：阿魏酰阿魏酰酒石酸Feruloylferuloyltartaric acid；16：芥子酰对香豆酰酒石酸Sinapoyl-p-coumaroyltartaric acid；17：对香豆酰奎宁酸-4′-O-葡萄糖醛酸苷p-coumaroylquinic acid-4′-O-glucuronide；18：3, 5-二咖啡酰奎尼酸3, 5-dicaffeoylquinic acid；19：3-O-阿魏酰奎宁酸-O-葡萄糖苷3-O-feruloylquinic acid-O-glucoside；20：1-羟基松脂醇-1-O-葡萄糖苷1-hydroxypinoresinol-1-O-glucoside；21：5′-甲氧基罗汉松脂苷5′-methoxymatairesinoside；22：异杞柳苷-6″-O-对香豆酸Isosalipurposide-6″-O-p-coumaric acid；23：二芥子酰葡萄糖苷Disinapoyl glucoside；24：槲皮素-3-O-(2″-肉桂酰)葡萄糖苷Quercetin-3-O-(2″-cinnamoyl)glucoside；25：槲皮素-3-O-(2″-对香豆酰)葡萄糖苷Quercetin-3-O-(2″-p-Coumaroyl)glucoside；26：金圣草黄素-7-O-(6″-阿魏酰)葡萄糖苷Chrysoeriol-7-O-(6″-feruloyl)glucoside；27：苜蓿酸-3-O-葡萄糖醛酸苷-28-O-鼠李糖基(1, 2)-阿拉伯糖苷Medicagenic acid-3-O-glucuronide-28-O-rhamnosyl(1, 2)-arabinoside."

图8

图9

表2

皂荚和野皂荚刺差异代谢物KEGG通路"

序号 No.	代谢通路(差异代谢物个数) KEGG pathway (quantity of differential metabolites)	P值 P-value
1	茋类、二芳基庚烷类和姜酚的生物合成Stilbenoid, diarylheptanoid and gingerol biosynthesis(7)	0.027 6
2	黄酮类生物合成Flavonoid biosynthesis(29)	0.054 9
3	异黄酮生物合成Isoflavonoid biosynthesis(7)	0.363 4
4	精氨酸和脯氨酸代谢Arginine and proline metabolism(5)	0.383 2
5	叶酸生物合成Folate biosynthesis(1)	0.437 9
6	硫胺代谢Thiamine metabolism(1)	0.437 9
7	苯丙烷生物合成Phenylpropanoid biosynthesis(20)	0.547 2
8	柠檬酸盐循环(TCA循环)Citrate cycle (TCA cycle)(4)	0.591 1
9	泛醌和其他萜类-醌生物合成Ubiquinone and other terpenoid-quinone biosynthesis(4)	0.591 1
10	乙醛酸和二羧酸代谢Glyoxylate and dicarboxylate metabolism(4)	0.591 1
11	碳代谢Carbon metabolism(4)	0.591 1
12	甘油磷脂代谢Glycerophospholipid metabolism(4)	0.591 1
13	2-氧代羧酸代谢2-oxocarboxylic acid metabolism(4)	0.591 1
14	次生代谢物的生物合成Biosynthesis of secondary metabolites(56)	0.639 7
15	植物激素信号转导Plant hormone signal transduction(2)	0.685 9
16	丙氨酸、天冬氨酸和谷氨酸代谢Alanine, aspartate and glutamate metabolism(2)	0.685 9
17	花青素生物合成Anthocyanin biosynthesis(2)	0.685 9
18	糖酵解/糖异生Glycolysis/gluconeogenesis(2)	0.685 9
19	黄酮和黄酮醇的生物合成Flavone and flavonol biosynthesis(17)	0.686 4
20	色氨酸代谢Tryptophan metabolism(11)	0.796 3
21	苯丙氨酸、酪氨酸和色氨酸生物合成Phenylalanine, tyrosine and tryptophan biosynthesis(3)	0.825 5
22	异喹啉生物碱生物合成Isoquinoline alkaloid biosynthesis(3)	0.825 5
23	氨基酸的生物合成Biosynthesis of amino acids(6)	0.826 9
24	烟酸和烟酰胺代谢Nicotinate and nicotinamide metabolism(4)	0.903 6
25	各种次级代谢产物的生物合成-第2部分Biosynthesis of various secondary metabolites-part 2(6)	0.971 1
26	苯丙氨酸代谢Phenylalanine metabolism(6)	0.971 1
27	酪氨酸代谢Tyrosine metabolism(10)	0.997 6
28	代谢途径Metabolic pathways(78)	0.999 6

表2

参考文献 0

	陈向阳. 薄荷酚类部位化学成分及抗炎活性研究. 北京: 北京中医药大学, 2016.
	Chen X Y . Study on the chemical constituents and anti-inflammatory activity of Mentha canadensis Linnaeus. Beijing: Beijing University of Chinese Medicine, 2016.
	陈永芬, 申琳, 鱼泳泳, 等. 低聚原花青素方剂对小鼠肝脏、血清中相关抗氧化酶活性及MDA、活性氧含量的影响. 食品科学, 2004, 25 (S1): 164- 167.
	Chen Y F , Shen L , Yu Y Y , et al. Effect of oligomeric proanthocyanidin prescription on the activity of related antioxidant enzymes, MDA and reactive oxygen species in liver and serum of mice. Food Chemistry, 2004, 25 (S1): 164- 167.
	刁红星, 易燕群, 戚辉, 等. 石斛酚与丁香酸联合抗白内障作用及其机制研究. 中国中药杂志, 2012, 37 (16): 2429.
	Diao H X , Yi Y Q , Qi H , et al. Study on the anti-cataract effect and mechanism of the combination of dendrobol and syringic acid. China Journal of Chinese Materia Medica, 2012, 37 (16): 2429.
	范理璋. 皂荚种子育苗技术. 中国种业, 2008, 11 (11): 58- 58. doi: 10.3969/j.issn.1671-895X.2008.11.032
	Fan L Z . Seed breeding technology of Gleditsia sinensis Lam. China Seed Industry, 2008, 11 (11): 58- 58. doi: 10.3969/j.issn.1671-895X.2008.11.032
	范金波, 蔡茜彤, 冯叙桥, 等. 咖啡酸体外抗氧化活性的研究. 中国食品学报, 2015, 15 (3): 65- 73.
	Fan J B , Cai X T , Feng X Q , et al. Studies on the antioxidant activity in vitro of caffeic acid. Journal of Chinese Institute of Food Science and Technology, 2015, 15 (3): 65- 73.
	顾万春, 兰彦平, 孙翠玲. 世界皂荚(属)的研究与开发利用. 林业科学, 2003, 39 (4): 127- 133. doi: 10.3321/j.issn:1001-7488.2003.04.021
	Gu W C , Lan Y P , Sun C L . Research, development and utilization of Gleditsia sinensis Lam.(Genus) in the world. Scientia Silvae Sinicae, 2003, 39 (4): 127- 133. doi: 10.3321/j.issn:1001-7488.2003.04.021
	国家药典委员会. 中华人民共和国药典. 北京: 中国医药科技出版社, 2020.
	Chinese Pharmacopoeia Commission . Pharmacopoeia of the People's Republic of China. Beijing: China Medical Science Press, 2020.
	何光志, 何前松, 李世军, 等. 皂角刺总黄酮对体内外人肝癌细胞株HepG2作用活性的研究. 内蒙古中医药, 2012, 31 (4): 47- 48. 47-48+119 doi: 10.3969/j.issn.1006-0979.2012.04.053
	He G Z , He Q S , Li S J , et al. Study on flavone components from spina gleditsiae of anti-Hepatocellular carcinoma HepG2 activity in vivo and in vitro. Nei Mongol Journal of traditional Chinese medicine, 2012, 31 (4): 47- 48. 47-48+119 doi: 10.3969/j.issn.1006-0979.2012.04.053
	黄云剑, 廖立生. 阿魏酸钠和维拉帕米对庆大霉素肾毒性的保护作用. 中国药理学通报, 1998, 14 (1): 77- 79.
	Huang Y J , Liao L S . Protective effects of sodium ferulate and verapamil on gentamicin nephrotoxicity. Chinese Pharmacological Bulletin, 1998, 14 (1): 77- 79.
	孔玉珊, 黄少兰, 谢明霞, 等. 排风藤提取物中东莨菪苷对神经细胞的抗氧化活性研究. 天然产物研究与开发, 2014, 26 (6): 943- 946.
	Kong Y S , Huang S L , Xie M X , et al. Antioxidant activity of scopolin from Solanum cathayanum to SH-SYSY cells. Natural Product Research and Development, 2014, 26 (6): 943- 946.
	兰彦平, 顾万春. 北方地区皂荚种子及荚果形态特征的地理变异. 林业科学, 2006, 42 (7): 47- 51.
	Lan Y P , Gu W C . Geographical variation of morphologic characteristics of Gleditsia sinensis seeds and legumes in the north region. Scientia Silvae Sinicae, 2006, 42 (7): 47- 51.
	梁晓天, 刘春雪, 姬政, 等. 莨菪亭及异莨菪亭的合成. 医药工业, 2013, 3 (4): 6- 7.
	Liang X T , Liu C X , Ji Zheng , et al. Synthesis of scopoltin and iso-scopoltin. Chinese Journal of Pharmaceuticals, 2103, 3 (4): 6- 7.
	刘伟杰, 杜钢军, 李佳桓, 等. 皂角刺总黄酮对肺癌的防治作用及其机制研究. 中草药, 2013, 44 (20): 2878- 2883.
	Liu W J , Du G J , Li J H , et al. Study on the preventive and therapeutic effects of total flavonoids of Gleditsia sinensis Lam. spine on lung cancer. Chinese Traditional and Herbal Drugs, 2013, 44 (20): 2878- 2883.
	刘云海, 方建国, 贡雪破, 等. 板蓝根中丁香酸的抗内毒素作用. 中草药, 2003, 34 (10): 926- 928. doi: 10.3321/j.issn:0253-2670.2003.10.030
	Liu Y H , Fang J G , Gong X P , et al. Anti-endotoxic effects of syringic acid in Radix Isatidis. Chinese Traditional and Herbal Drugs, 2003, 34 (10): 926- 928. doi: 10.3321/j.issn:0253-2670.2003.10.030
	龙玲. 2006. 皂刺抗宫颈癌活性及其作用机理的研究. 陕西: 西北农林科技大学.
	Long L. 2006. Study on the anti-cervical cancer activity of Gleditsia sinensis Lam. stings and its mechanism. Shanxi: Northwest A&F University. [in Chinese]
	彭钰芳, 邹文韬, 许传莲. 杭白菊中黄酮类化合物及其抑制人源肿瘤细胞增殖活性的研究. 中国药学杂志, 2010, 45 (19): 1454- 1459.
	Peng Y F , Zou W T , Xu C L . Evaluation of flavonoids from flos chrysanthemi on cell proliferation in human cancer cells. Chinese Pharmaceutical Journal, 2010, 45 (19): 1454- 1459.
	邱立友, 戚元成, 王明道, 等. 植物次生代谢物的自毒作用及其与连作障碍的关系. 土壤, 2010, 42 (1): 1- 7.
	Qiu L Y , Qi Y C , Wang M D , et al. Relationship between secondary metabolite autotoxic to plant and continuous cropping obstacles. Soils, 2010, 42 (1): 1- 7.
	宋忠兴, 唐志书, 严邑萍, 等. 皂角刺中总黄酮含量测定及其抗氧化活性研究. 中国药业, 2019, 28 (6): 1- 3. doi: 10.3969/j.issn.1006-4931.2019.06.001
	Song Z X , Tang Z S , Yan Y P , et al. Determination of total flavonoids in Gleditsia sinensis Lam.thorn and its antioxidant activity. China Pharmaceuticals, 2019, 28 (6): 1- 3. doi: 10.3969/j.issn.1006-4931.2019.06.001
	苏文华, 张光飞, 李秀华, 等. 植物药材次生代谢产物的积累与环境的关系. 中草药, 2005, 36 (9): 1415- 1418. doi: 10.3321/j.issn:0253-2670.2005.09.052
	Su W H , Zhang G F , Li X H , et al. Relationship between accumulation of secondary metabolism in medicinal plant and environmental condition. Chinese Traditional and Herbal Drugs, 2005, 36 (9): 1415- 1418. doi: 10.3321/j.issn:0253-2670.2005.09.052
	陶鑫, 许枬, 王秀兰, 等. 兴安毛连菜中有机酸化学成分及其抗氧化活性的研究. 中草药, 2016, 47 (4): 544- 548.
	Tao X , Xu D , Wang X L , et al. Organic acids derived from Picris davurica and their anti-oxidative activity. Chinese Traditional and Herbal Drugs, 2016, 47 (4): 544- 548.
	田京伟, 杨建雄. 白藜芦醇苷的体外抗氧化活性. 中草药, 2001, 32 (10): 918- 920. doi: 10.3321/j.issn:0253-2670.2001.10.023
	Tian J W , Yang J X . In vitro antioxidative effect of polydatin. Chinese Traditional and Herbal Drugs, 2001, 32 (10): 918- 920. doi: 10.3321/j.issn:0253-2670.2001.10.023
	王慧, 张红歧, 邬昊洋, 等. 筒鞘蛇菰提取物及松柏苷的抗氧化作用研究. 三峡大学学报(自然科学版), 2009, 31 (3): 99- 101.
	Wang H , Zhang H Q , Wu H Y , et al. Study of anti-oxidation effects of extracts of balanophora involucrate and trans-coniferin. Journal of China Three Gorges University(Natural Sciences Edition), 2009, 31 (3): 99- 101.
	王世依, 王梦凡. 不同皂荚品种外部形态内部结构的比较. 科技经济导刊, 2016, (18): 138- 138. 138-138, 137
	Wang S Y , Wang M F . Comparison of external morphology and internal structure of different Gleditsia Linn varieties. Technology and Economic Guide, 2016, (18): 138- 138. 138-138, 137
	王晓丽. 2014. 光皮木瓜黄酮类物质的提取及抗氧化性研究. 山东: 山东农业大学.
	Wang X L. 2014. Study on the extraction and antioxidant activity of flavonoids in Chaenomeles sinensis (Thouin) Koehne. Shandong: Shandong Agricultural University. [in Chinese]
	王晓梅, 奚宇, 范新光, 等. 绿原酸的生物利用率和抗氧化活性研究进展. 中国食品学报, 2019, 19 (1): 271- 279.
	Wang X M , Xi Y , Fan X G , et al. Research progress on bioavailability and antioxidant activity of chlorogenic acid. Journal of Chinese Institute of Food Science and Technology, 2019, 19 (1): 271- 279.
	王月华, 杨红英, 付崇罗, 等. 香叶木素和香叶木素-7-O-β-D-吡喃葡萄糖苷的生物活性比较. 天然产物研究与开发, 2017, 29 (7): 113- 118.
	Wang Y H , Yang H Y , Fu C L , et al. Comparison of biological activities of diosmetin and.diosmetin-7-O-β-d-glucopyranoside. Natural Product Research and Development, 2017, 29 (7): 113- 118.
	徐哲, 赵晓頔, 王漪檬, 等. 皂角刺抗肿瘤活性成分的分离鉴定与活性测定. 沈阳药科大学学报, 2008, 25 (2): 108- 111. 108-111+162 doi: 10.3969/j.issn.1006-2858.2008.02.007
	Xu Z , Zhao X D , Wang Y M , et al. Identification and anti-tumor activity determination about anti-tumor components of Gleditsia sinensis Lam.stings. Journal of Shenyang Pharmaceutical University, 2008, 25 (2): 108- 111. 108-111+162 doi: 10.3969/j.issn.1006-2858.2008.02.007
	杨军, 宋硕林, Castro-PerezJ, 等. 代谢组学及其应用. 生物工程学报, 2005, 21 (1): 1- 5. doi: 10.3321/j.issn:1000-3061.2005.01.001
	Yang J , Song S L , Castro-Perez J , et al. Metabolomics and its applications. Chinese Journal of Biotechnology, 2005, 21 (1): 1- 5. doi: 10.3321/j.issn:1000-3061.2005.01.001
	赵雪飞. 2018. 玛咖的化学成分和活性研究. 山东: 济南大学.
	Zhao X F. 2018. Studies on the chemical constituents and activities of Lepidium meyenii Walp. Shandong: University of Jinan. [in Chinese]
	张妍, 阮连国, 曾友玲, 等. 皂刺粗黄酮对小鼠移植U14宫颈癌细胞生长的影响及机制. 中国老年学杂志, 2017, 37 (22): 5553- 5555. doi: 10.3969/j.issn.1005-9202.2017.22.029
	Zhang Y , Ruan L G , Zeng Y L , et al. The effect of crude flavonoids from Gleditsia sinensis Lam.on the growth of transplanted U14 cervical cancer cells in mice and its mechanism. Chinese Journal of Gerontology, 2017, 37 (22): 5553- 5555. doi: 10.3969/j.issn.1005-9202.2017.22.029
	郑新恒. 2018. 云南枸杞根中化学成分及其生物活性研究. 广东: 暨南大学.
	Zheng X H. 2018. Studies on constituents from the root of Lycium yunnanense Kuang and their biological activity. guangdong: Jinan University. [in Chinese]
	Bourgaud F , Gravot A , Milesi S , et al. Production of plant secondary metabolites: a historical perspective. Plant Science, 2001, 161 (5): 839- 851. doi: 10.1016/S0168-9452(01)00490-3
	Fraga C G , Clowers B H , Moore R J , et al. Signature-discovery approach for sample matching of a nerve-agent precursor using liquid chromatography-mass spectrometry, XCMS, and chemometrics. Analytical Chemistry, 2010, 82 (10): 4165- 4173. doi: 10.1021/ac1003568
	Griffiths L A . Studies on flavonoid metabolism. Identification of the metabolites of (+)-catechin in rat urine. Biochemical Journal, 1964, 92 (1): 173- 179. doi: 10.1042/bj0920173
	Hsieh M T , Tsai F H , Lin Y C , et al. Effects of ferulic acid on the impairment of inhibitory avoidance performance in rats. Planta Medica, 2002, 68 (8): 754- 756. doi: 10.1055/s-2002-33800
	Jiang J , Zhu L , Wang L , et al. Studies on modification of polysaccharide gum from Gleditsia sinensis Lam.seeds with α-galactosidase. Chemistry & Industry of Forest Products, 2007, 27 (5): 44- 48.
	Kawabata K , Yamamoto T , Hara A , et al. Modifying effects of ferulic acid on azoxymethane-induced colon carcinogenesis in F344 rats. Cancer Letters, 2000, 157 (1): 15- 21. doi: 10.1016/S0304-3835(00)00461-4
	Lee S H , Zhou B , Kim J K , et al. Scopoletin and scopolin isolated from Artemisia iwayomogi suppress differentiation of osteoclastic macrophage RAW 264.7 cells via scavenging reactive oxygen species. Journal of Natural Products, 2013, 76 (4): 615- 620. doi: 10.1021/np300824h
	Li H Y , Lü Q Y , Ma C , et al. Metabolite profiling and transcriptome analyses provide insights into the flavonoid biosynthesis in the developing seed of tartary buckwheat (Fagopyrum tataricum). Journal of Agricultural and Food Chemistry, 2019, 67 (40): 11262- 11276. doi: 10.1021/acs.jafc.9b03135
	Li K K , Zhou X L , Wong H K , et al. In vivo and in vitro anti-inflammatory effects of Zao-Jiao-Ci (the spine of Gleditsia sinensis Lam.) aqueous extract and its mechanisms of action. Journal of Ethnopharmacology, 2016, 6 (9): 39- 48.
	Maher P , Akaishi T , Abe K . Flavonoid fisetin promotes ERK-dependent long-term potentiation and enhances memory. Proceedings of the National Academy of Sciences, 2006, 103 (44): 16568- 16573. doi: 10.1073/pnas.0607822103
	Meng J , Wang B , He G , et al. Metabolomics integrated with transcriptomics reveals redirection of the phenylpropanoids metabolic flux in Ginkgo biloba. Journal of Agricultural and Food Chemistry, 2019, 67 (25): 3284- 3291.
	Park S S , Kim W J , Moon S K . Gleditsia sinensis Lam.thorn extract inhibits the proliferation and migration of PDGF induced vascular smooth muscle cells. Molecular Medicine Reports, 2014, 10 (4): 2031- 2038. doi: 10.3892/mmr.2014.2422
	Russo M , Spagnuolo C , Tedesco I , et al. The flavonoid quercetin in disease prevention and therapy: facts and fancies. Biochemical Pharmacology, 2012, 83 (1): 6- 15. doi: 10.1016/j.bcp.2011.08.010
	Seo C , Lim H , Ha H , et al. Quantitative analysis and anti-inflammatory effects of Gleditsia sinensis thorns in RAW 264.7 macrophages and HaCaT keratinocytes. Molecular Medicine Reports, 2015, 12 (3): 4773- 4781. doi: 10.3892/mmr.2015.3936
	Suzuki A , Kagawa D , Fujii A , et al. Short- and long-term effects of ferulic acid on blood pressure in spontaneously hypertensive rats. American Journal of Hypertension, 2002, 15 (4): 351- 357. doi: 10.1016/S0895-7061(01)02337-8
	Vinale F , Ghisalberti E L , Sivasithamparam K , et al. Factors affecting the production of Trichoderma harzianum secondary metabolites during the interaction with different plant pathogens. Letters in Applied Microbiology, 2010, 48 (6): 705- 711.
	Wang F , Chen L , Chen H , et al. Analysis of flavonoid metabolites in citrus peels (Citrus reticulata "Dahongpao") using UPLC-ESI-MS/MS. Molecules, 2019, 24 (15): 2680- 2692. doi: 10.3390/molecules24152680
	Yan J J , Cho J Y , Kim H S , et al. Protection against beta-amyloid peptide toxicity in vivo with long-term administration of ferulic acid. British Journal of Pharmacology, 2001, 133 (1): 89- 96. doi: 10.1038/sj.bjp.0704047
	Zhou L , Li D , Jiang W , et al. Two ellagic acid glycosides from Gleditsia sinensis Lam.with antifungal activity on Magnaporthe grisea. Natural Product Research, 2007, 21 (4): 303- 309. doi: 10.1080/14786410701192702

[1]	陈新,王敏,傅茂润,王贵芳,相昆,刘庆忠,焦文晓,张美勇,许海峰. 核桃炭疽病发生相关的酚类物质代谢分析[J]. 林业科学, 2021, 57(10): 71-80.
[2]	闫海冰,张慧芳,冯帆,于兆友,杨秀清. 2种白刺对盐胁迫的代谢响应机制[J]. 林业科学, 2021, 57(1): 20-29.
[3]	陆小雨,陈竹,唐菲,傅松玲,任杰. 转录组与代谢组联合解析红花槭叶片中花青素苷变化机制[J]. 林业科学, 2020, 56(1): 38-53.
[4]	刘果, 陈鸿鹏, 吴志华, 彭彦, 谢耀坚. 南美油藤种子发育过程的代谢组学和转录组学联合分析[J]. 林业科学, 2019, 55(5): 169-179.
[5]	候亚会, 严善春, 李志强. 对苯二酚对台湾乳白蚁诱食效果及其诱导代谢的响应[J]. 林业科学, 2018, 54(9): 97-103.
[6]	曹亚兵, 翟晓巧, 邓敏捷, 赵振利, 范国强. 泡桐丛枝病发生与代谢组变化的关系[J]. 林业科学, 2017, 53(6): 85-93.
[7]	王艳梅, 何山林, 尚铁军, 赵晓斌, 李灵会. 皂荚良种‘嵩刺1号’[J]. 林业科学, 2016, 52(10): 170-170.
[8]	兰彦平顾万春. 北方地区皂荚种子及荚果形态特征的地理变异[J]. 林业科学, 2006, 42(7): 47-51.
[9]	顾万春兰彦平孙翠玲. 世界皂荚(属)的研究与开发利用[J]. 林业科学, 2003, 39(4): 127-133.