基于广泛靶向代谢组学的葡萄种子代谢物鉴定与比较分析

doi:10.3864/j.issn.0578-1752.2023.07.013

Abstract

Abstract:

【Objective】 Grape seeds have high bioactivity because they are rich in many metabolites. The objective of this study was to comprehensively identify the metabolite components in grape seeds, to compare and to analyze the differences of metabolites among different varieties, and to explore the relationship between metabolites in grape seeds and skin color and variety origin, so as to provide a reference basis for further development and utilization of grape seeds. 【Method】 The mature seeds of purple-skinned Kyoho (V. labruscana: V. labrusca × V. vinifera, JFS), pink-skinned Wink (V. vinifera, WKS), and yellow-skinned Italia (V. vinifera, YDS) were used for widely targeted metabolomics analysis by UPLC-MS/MS. The metabolites were identified and compared by multivariate statistical methods. 【Result】 The quality of metabolomics data was good, and the data of samples within groups was repetitive and the differences in the data of samples among groups were existed. A total of 514 metabolites were identified in the seeds of three grape varieties, including 6 primary metabolites, such as amino acids and lipids, and 20 secondary metabolites, such as proanthocyanidins and resveratrol. Among different varieties, the metabolite components were similar but the metabolite contents were significantly different. The relative contents of most metabolites were high in the dark variety Kyoho, followed by the light variety Wink, but low in the colorless variety Italy, indicating that the metabolite contents in grape seeds might be positively correlated with the skin color. The relative contents of metabolites in the seeds of Wink and Italia were similar, while they were greatly different from those of Kyoho, indicating that the metabolite contents in grape seeds might be related to the variety origin. The differential metabolites among different varieties were mainly involved in phenylpropane biosynthesis, anthocyanin synthesis, lipid metabolism, etc. pathway. There were many phenolic compounds in the differential metabolites and the metabolites with the large difference were mainly flavonoids. Grape seeds were rich in phenols and lipids. In addition to monomeric flavane-3-ols and their polymers, the relative contents of other phenolic compounds such as flavones and flavonols were also high. There was no significant difference in the relative contents of resveratrol among the three varieties. The relative contents of glyceryl phosphatide such as lysophosphatidylcholine were high, while those of linolenic acid were low. There was little difference in the relative contents of lipids among different varieties. 【Conclusion】 The metabolite components in grape seeds of different varieties were similar, while the metabolite contents were related to the skin color and the variety origin. Phenols and lipids were important components of metabolites in grape seeds and could be used as good sources for food and other processing industries.

Key words: grape (Vitis vinifera), seed, metabolomics, metabolite, phenol, lipid

SHENG HongJie, LU SuWen, ZHENG XuanAng, JIA HaiFeng, FANG JingGui. Identification and Comparative Analysis of Metabolites in Grape Seed Based on Widely Targeted Metabolomics[J].Scientia Agricultura Sinica, 2023, 56(7): 1359-1376.

Figures/Tables 14

Fig. 1

Fig. 2

Fig. 3

Table 1

Fig. 4

Fig. 5

Fig. 6

Table 2

The common differential metabolites in the three comparisons"

物质 Compound	物质类别 Class	比较组 Comparison group
物质 Compound	物质类别 Class	JFS vs WKS	WKS vs YDS	JFS vs YDS
肌醇 Inositol	其他 Other	上调 Up	上调 Up	上调 Up
羟基金雀异黄素 2'-Hydroxygenistein	黄酮 Flavone	上调 Up	上调 Up	上调 Up
肌酸 Creatine	有机酸 Organic acid	上调 Up	上调 Up	上调 Up
紫丁香苷 Syringin	羟基肉桂酰 Hydroxycinnamoyl	上调 Up	下调 Down	上调 Up
N-芥子酰腐胺 N-Sinapoyl putrescine	酚胺 Phenolamide	上调 Up	下调 Down	上调 Up
对香豆酰五羟色胺己糖苷 N-hexosyl-p-coumaroyl serotonin	色胺 Tryptamine	上调 Up	下调 Down	上调 Up
3-羟基-3-甲基谷氨酸 3-Hydroxy-3-methylpentane-1,5-dioic acid	氨基酸 Amino acid	上调 Up	下调 Down	下调 Down
矢车菊素 3-O-葡萄糖苷 Cyanidin 3-O-glucoside	花青素 Anthocyanin	上调 Up	下调 Down	下调 Down
花青素苷 Cyanidin 3,5-O-diglucoside	花青素 Anthocyanin	上调 Up	下调 Down	下调 Down
迷迭香酸 Rosmarinic acid	有机酸 Organic acid	下调 Down	上调 Up	上调 Up
2'-脱氧鸟苷 Deoxyguanosine	核苷酸 Nucleotide	下调 Down	上调 Up	上调 Up
2-脱氧肌苷2'-Deoxyinosine	核苷酸 Nucleotide	下调 Down	上调 Up	上调 Up
2-脱氧腺苷 Deoxyadenosine	核苷酸 Nucleotide	下调 Down	上调 Up	上调 Up
毡毛美洲茶素 Velutin	黄酮 Flavone	下调 Down	上调 Up	下调 Down
麦黄酮 4'-O-丁香醇醚7-O-己糖苷 Tricin 4'-O-(syringyl alcohol) ether 7-O-hexoside	黄酮 Flavone	下调 Down	上调 Up	下调 Down
反式-4-羟基-3-甲氧基肉桂酸 Hydroxy-methoxycinnamate	羟基肉桂酰 Hydroxycinnamoyl	下调 Down	上调 Up	下调 Down
单酰甘油酯(酰基18:3)异构3 MAG (18:3) isomer3	脂质 Lipid	下调 Down	上调 Up	下调 Down
壬二酸 Azelaic Acid	有机酸 Organic acid	下调 Down	下调 Down	下调 Down
2-(甲酰氨基)苯甲酸 2-(Formylamino) benzoic acid	有机酸 Organic acid	下调 Down	下调 Down	下调 Down
DL-高半胱氨酸 DL-homocysteine	氨基酸 Amino acid	下调 Down	下调 Down	下调 Down
N-乙酰-L-谷氨酸 N-Acetyl-L-glutamic acid	氨基酸 Amino acid	下调 Down	下调 Down	下调 Down
蛋氨酸亚砜 Methionine sulfoxide	氨基酸 Amino acid	下调 Down	下调 Down	下调 Down
香兰素 Vanillin	苯甲酸 Benzoic acid	下调 Down	下调 Down	下调 Down
黄苷 Xanthosine	核苷酸 Nucleotide	下调 Down	下调 Down	下调 Down
杨梅苷 Myricetin 3-O-rhamnoside	黄酮醇 Flavonol	下调 Down	下调 Down	下调 Down
乔松素 Pinocembrin	黄烷酮 Flavanone	下调 Down	下调 Down	下调 Down
5-O-对香豆酰莽草酸 5-O-p-Coumaroyl shikimic acid	奎宁酸 Quinate	下调 Down	下调 Down	下调 Down
3,4-二甲氧基肉桂酸 3,4-Dimethoxycinnamic acid	羟基肉桂酰 Hydroxycinnamoyl	下调 Down	下调 Down	下调 Down
4-甲氧基肉桂酸 4-Methoxycinnamic acid	羟基肉桂酰 Hydroxycinnamoyl derivatives	下调 Down	下调 Down	下调 Down
阿魏酸 Ferulic acid	羟基肉桂酰 Hydroxycinnamoyl	下调 Down	下调 Down	下调 Down
松柏醛 Coniferylaldehyde	羟基肉桂酰 Hydroxycinnamoyl	下调 Down	下调 Down	下调 Down
松柏醇 Coniferyl alcohol	羟基肉桂酰 Hydroxycinnamoyl	下调 Down	下调 Down	下调 Down

Table 2

Fig. 7

Table 3

Fig. 8

Fig. 9

Table 4

Important polyphenols in grape seeds"

物质 Compound	葡萄种子 Grape seed			比较组 Comparison group
物质 Compound	JFS	WKS	YDS	JFS vs WKS	WKS vs YDS	JFS vs YDS
花青素 Anthocyanin
矢车菊素 3-O-葡萄糖苷 Cyanidin 3-O-glucoside	7.86E+06	3.66E+07	1.91E+06	2.22	-4.26	-2.04
矢车菊素 3-O-芸香糖苷 Cyanidin 3-O-rutinoside	2.27E+06	5.78E+06	3.68E+06	1.35	—	—
天竺葵素-3-O-葡萄糖苷 Pelargonidin 3-O-glucoside	9.00E+00	1.09E+07	9.00E+00	20.21	-20.21	—
花青素苷 Cyanidin 3,5-O-diglucoside	4.78E+05	1.63E+06	9.00E+00	1.77	-17.47	-15.70
芍药花青素O-己糖苷 Peonidin O-hexoside	1.98E+05	1.64E+06	9.00E+00	—	-17.48	—
天竺葵色素苷 Pelargonin	9.00E+00	7.50E+05	7.63E+05	16.35	—	16.37
儿茶素 Catechin
原儿茶醛 Protocatechuic aldehyde	1.51E+07	1.48E+07	1.12E+07	—	—	—
三儿茶素 Catechin-catechin-catechin	1.33E+07	9.29E+06	5.89E+06	—	—	—
原儿茶酸 Protocatechuic acid	8.58E+06	4.22E+06	5.53E+06	—	—	—
原花青素 Proanthocyanidin
原花青素B2 Procyanidin B2	1.47E+07	1.80E+07	1.70E+07	—	—	—
原花青素A2 Procyanidin A2	1.07E+07	7.82E+06	1.21E+07	—	—	—
原花青素A3 Procyanidin A3	9.21E+06	2.73E+07	2.37E+07	1.57	—	1.37
黄酮 Flavone
木犀草苷 Luteolin 7-O-glucoside	4.98E+07	8.40E+07	8.14E+07	—	—	—
紫铆素 Butin	5.04E+06	6.04E+06	3.32E+06	—	—	—
物质 Compound	葡萄种子 Grape seed			比较组 Comparison group
物质 Compound	JFS	WKS	YDS	JFS vs WKS	WKS vs YDS	JFS vs YDS
圣草酚 C-己糖 Eriodictyol C-hexoside	3.80E+07	4.05E+07	5.22E+07	—	—	—
金圣草黄素 7-O-芸香糖苷 Chrysoeriol 7-O-rutinoside	2.38E+05	7.82E+04	9.00E+00	—	-13.08	-14.69
麦黄酮 7-O-己糖苷 Tricin 7-O-hexoside	1.47E+05	8.46E+04	9.00E+00	—	-13.20	-14.00
麦黄酮 5-O-己糖苷 Tricin 5-O-hexoside	1.40E+05	9.00E+00	2.76E+04	-13.93	—	—
菠叶素 Spinacetin	8.48E+04	9.00E+00	9.00E+00	-13.20	—	-13.20
麦黄酮 7-O-己糖基-O-己糖苷 Tricin 7-O-hexosyl-O-hexoside	9.00E+00	1.55E+05	2.70E+04	14.07	—	—
麦黄酮 4'-O-丁香醇醚 7-O-己糖苷 Tricin 4'-O-(syringyl alcohol) ether 7-O-hexoside	1.25E+05	9.00E+00	1.21E+04	-13.76	10.39	-3.37
6-C-己糖苷-芹菜素 O-阿魏酰己糖苷 6-C-hexosyl-apigenin O-feruloylhexoside	1.34E+06	9.00E+00	9.00E+00	-17.19	—	-17.19
氧甲基柚皮素 C-戊糖苷 O-methylnaringenin C-pentoside	2.35E+05	9.00E+00	9.00E+00	-14.67	—	-14.67
异黄酮 Isoflavone
染料木苷 Genistein 7-O-Glucoside	1.61E+06	2.71E+06	3.31E+06	—	—	1.04
黄酮醇 Flavonol
三叶豆甙 Kaempferol 3-O-galactoside	4.13E+07	7.39E+07	6.62E+07	—	—	—
黄颜木素 Fustin	1.02E+07	1.22E+07	2.09E+07	—	—	1.03
绣线菊甙 Quercetin 4'-O-glucoside	8.10E+06	1.46E+07	1.56E+07	—	—	—
异鼠李素-3-O-新橙皮糖苷 Isorhamnetin 3-O-neohesperidoside	8.53E+05	9.00E+00	9.67E+04	-16.53	—	—
3,7-二-O-甲基槲皮素 3,7-Di-O-methylquercetin	4.01E+04	9.00E+00	6.98E+04	-12.12	12.92	—
黄烷酮 Flavanone
橙皮素 5-O-葡萄糖苷 Hesperetin 5-O-glucoside	8.39E+06	1.55E+07	1.66E+07	—	—	—
柚皮素 Naringenin	5.20E+06	6.70E+06	3.76E+06	—	—	—
柚皮苷查尔酮 Naringenin chalcone	4.98E+06	5.16E+06	2.76E+06	—	—	—
新橙皮苷 Hesperetin 7-O-neohesperidoside	2.77E+05	1.20E+05	9.00E+00	—	-13.70	—
7-氧甲基圣草酚 7-O-Methyleriodictyol	9.00E+00	9.00E+00	1.89E+04	—	11.04	11.04
苯甲酸 Benzoic acid
2,5-二羟基苯甲酸 O-己糖苷 2,5-dihydroxy benzoic acid O-hexside	2.92E+07	3.39E+07	5.05E+07	—	—	—
对-氨基苯甲酸 p-Aminobenzoate	1.71E+07	9.05E+06	8.87E+06	—	—	—
没食子酸甲酯 Methyl gallate	6.47E+06	7.47E+06	1.36E+07	—	—	1.07
奎宁酸 Quinate
奎宁酸 Quinic acid	1.67E+06	1.56E+06	9.13E+05	—	—	—
5-O-对香豆酰莽草酸 5-O-p-Coumaroyl shikimic acid	1.27E+05	4.34E+04	9.00E+00		-12.24	-13.78
O-阿魏酰奎尼酸 O-Feruloyl quinic acid	9.00E+00	2.08E+04	5.65E+04	—	—	12.62
羟基肉桂酰 Hydroxycinnamoyl
松柏醛 Coniferylaldehyde	1.93E+07	1.08E+06	2.31E+05	-4.16	-2.23	-6.39
松脂醇 Pinoresinol	1.21E+07	3.84E+05	4.33E+05	-4.97	—	-4.80
高香草酸 Homovanillic acid	5.95E+06	1.10E+06	1.18E+06	-2.44	—	-2.34
芥子酸吡喃葡萄糖苷 1-O-beta-D-Glucopyranosyl sinapate	9.00E+00	3.54E+04	3.63E+04	11.94	—	11.98
白藜芦醇 Resveratrol	8.71E+05	6.19E+05	5.17E+05	—	—	—

Table 4

Table 5

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物质 Compound	葡萄种子 Grape seed			比较组 Comparison group
物质 Compound	JFS	WKS	YDS	JFS vs WKS	WKS vs YDS	JFS vs YDS
脂质-甘油磷脂 Lipids-Glycerophospholipids
溶血磷脂酰胆碱 16:0 LysoPC 16:0	2.57E+08	1.98E+08	1.61E+08	—	—	—
溶血磷脂酰胆碱 16:0 LysoPC 16:0	2.46E+08	1.88E+08	1.51E+08	—	—	—
溶血磷脂酰胆碱 18:1 LysoPC 18:1	7.60E+07	1.17E+08	1.14E+08	—	—	—
脂质-甘油酯 Lipids-Glycerolipids
单酰甘油酯 (酰基 18:3) MAG (18:3)	2.19E+06	9.92E+05	8.17E+05	-1.14	—	-1.42
单酰甘油酯单糖 (18:2) MGMG (18:2)	7.71E+05	3.62E+05	3.84E+05	-1.09	—	-1.01
单酰甘油酯二糖 (18:2) DGMG (18:2)	7.52E+05	2.67E+05	2.64E+05	-1.49	—	-1.51
脂质-脂肪酸 Lipids-Fatty acids
十八碳-三烯酸 Octadeca-trienoic acid	6.76E+07	3.64E+07	3.28E+07	—	—	-1.05
4-羟基鞘氨醇 4-Hydroxysphinganine	2.71E+07	7.94E+06	6.55E+06	-1.77	—	-2.05
石榴酸 Punicic acid	1.27E+07	1.77E+07	6.12E+06	—	-1.53	—

Identification and Comparative Analysis of Metabolites in Grape Seed Based on Widely Targeted Metabolomics

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物质类别 Class	巨峰 JFS	魏可 WKS	黄意大利 YDS	总计 Total
氨基酸 Amino acid	78	79	78	79
脂类 Lipid	65	64	65	65
有机酸Organic acid	55	55	51	58
核苷酸Nucleotide	57	57	58	58
糖类 Carbohydrate	16	19	18	19
醇类Alcohol	7	7	7	7
黄酮 Flavone	35	32	31	38
黄酮醇 Flavonol	29	26	28	30
黄烷酮 Flavanone	14	14	14	15
儿茶素Catechin	11	11	11	11
花青素 Anthocyanin	6	8	5	8
异黄酮 Isoflavone	5	5	5	6
原花青素 Proanthocyanidin	4	4	4	4
羟基肉桂酰 Hydroxycinnamoyl	21	22	22	23
苯甲酸 Benzoic acid	12	12	12	12
奎宁酸 Quinate	4	5	4	5
香豆素 Coumarin	3	4	4	4
维生素 Vitamin	13	13	13	13
酚胺 Phenolamide	11	12	12	12
吲哚 Indole	5	4	4	5
生物碱 Alkaloid	3	4	3	4
色胺 Tryptamine	3	4	4	4
胆碱 Choline	3	3	3	3
吡啶 Pyridine	2	2	2	2
烟酸 Nicotinic acid	3	3	3	3
萜类 Terpenoid	2	2	2	2
其他 Other	24	23	24	24
总计 Total	491	494	487	514

物质类别 Class	JFS vs WKS			WKS vs YDS			JFS vs YDS
物质类别 Class	总数 Total	上调 Up	下调 Down	总数 Total	上调 Up	下调 Down	总数 Total	上调 Up	下调 Down
总数目 Total numbers	170	71	99	121	40	81	189	70	119
氨基酸 Amino acid	18	9	9	16	3	13	34	13	21
脂类 Lipid	18	7	11	9	1	8	27	6	21
有机酸 Organic acid	16	8	8	17	7	10	15	9	6
核苷酸 Nucleotide	17	5	12	16	8	8	16	8	8
糖类 Carbohydrate	6	5	1	3	1	2	3	2	1
醇类 Alcohol	3	2	1	1	1	0	2	2	0
黄酮 Flavone	18	4	14	13	7	6	15	2	13
黄酮醇 Flavonol	14	2	12	7	5	2	16	4	12
黄烷酮 Flavanone	2	1	1	6	1	5	5	1	4
儿茶素 Catechin	3	3	0	2	0	2	2	1	1
花青素 Anthocyanin	5	5	0	4	0	4	3	1	2
异黄酮 Isoflavone	4	2	2	2	2	0	4	3	1
原花青素 Proanthocyanidin	1	1	0	0	0	0	2	2	0
羟基肉桂酰 Hydroxycinnamoyl	14	2	12	9	1	8	13	2	11
苯甲酸 Benzoic acid	3	1	2	3	0	3	3	1	2
奎宁酸 Quinate	2	1	1	1	0	1	3	2	1
香豆素 Coumarin	0	0	0	0	0	0	0	0	0
维生素 Vitamin	2	1	1	3	1	2	4	2	2
酚胺 Phenolamide	7	4	3	4	1	3	4	3	1
吲哚 Indole	1	0	1	0	0	0	1	0	1
生物碱 Alkaloid	1	1	0	1	0	1	0	0	0
色胺 Tryptamine	2	1	1	2	0	2	3	1	2
胆碱 Choline	0	0	0	0	0	0	0	0	0
吡啶 Pyridine	0	0	0	0	0	0	0	0	0
烟酸 Nicotinic acid	1	0	1	0	0	0	2	0	2
萜类 Terpenoid	2	0	2	0	0	0	2	0	2
其他 Other	10	6	4	2	1	1	10	5	5

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