白菜型油菜硫苷含量与组分分析

doi:10.3864/j.issn.0578-1752.2024.21.011

Abstract

Abstract:

【Objective】 Brassica rapa L. originated from China, whose qualify analysis and evaluation was highly important for its development and utilization. 【Method】 In this study, rapeseed was used as the research object. After grinding extraction and ion exchange column treatment, the glucosinolate extract was obtained. The high performance liquid chromatography (HPLC) was utilized to determine and analyze the content and components of glucosinolates in 323 B. rapa L. accessions. 【Result】 The total content of glucosinolates in 323 B. rapa L. samples ranged from 26.19 to 238.21 µmol∙g^-1, with an average of 137.22 µmol∙g^-1. A total of 9 glucosinolate components were identified, consisting of five aliphatic glucosinolates (progoitrin, glucoraphanin, gluconapoleiferin, gluconapin and glucobrassicanapin), three indole glucosinolates (4-hydroxyglucobrassicin, glucobrassicin, and 4-methoxyglucobrassicin), and one aromatic glucosinolate (gluconasturtiin). The predominant glucosinolate in B. rapa L. was gluconapin, which belonged to the aliphatic glucosinolate group. It had an average concentration of 122.68 µmol∙g^-1, making up 93.71% of the aliphatic glucosinolate content and 89.40% of the overall glucosinolate content. The comparison of the total glucosinolate content in accessions originated from various ecological zones indicated that the Yangtze River basin had the highest glucosinolate content, followed by the Huanghuai region, Xizang, and Gansu accessions. Among accessions, the content of 4-hydroxyglucobrassicin and glucobrassicin in Gansu accessions was more than that in accessions originated from the other three ecological zones. The content of gluconapin in Gansu accessions was the lowest compared to other accessions. The content of indole glucosinolates exhibited significant variations based on their sensitivity to temperature, with the highest levels observed in harsh winter types (11.50 µmol∙g^-1), followed by winter types (7.60 µmol∙g^-1), semi-winter types (6.77 µmol∙g^-1), and spring types (3.87 µmol∙g^-1). The findings demonstrated that, the content of progoitrin and indole glucosinolates differed significantly among the germplasm collection used in this study. Six accessions with high-indolyl glucoside content (ranging from 5.86 to 13.81 µmol∙g^-1) and three accessions with progoitrin content (ranging from 50.14 to 68.38 µmol∙g^-1) were selected by screening. 【Conclusion】 Aliphatic glucosinolates were the primary components of glucosinolates in B. rapa L., with gluconapin being the predominant component. The glucosinolate components exhibited significant variations depending on the genotype of the accessions. Different genotypes were selected based on their concentration of ultra-high glucosinolate, high indole glucosinolate, and high progoitrin.

Key words: Brassica rapa L., rapeseed, glucosinolates, components analyze, HPLC

MA YuHe, PU YuanYuan, WANG JinXiong, WU JunYan, YANG Gang, ZHAO CaiXia, MA Li, LIU LiJun, WANG WangTian, MIAO ChunQing, GUAN ZhouBo, FAN TingTing, WANG XingRong, MA Rui, LIAN YinTao, SUN WanCang. Analysis of Glucosinolate Content and Component in Brassica rapa L.[J].Scientia Agricultura Sinica, 2024, 57(21): 4308-4327.

Figures/Tables 11

Table 1

Table 2

Table 3

Fig. 1

Fig. 2

Table 4

Total amount of glucosinolates and content of various components under different levels of total glucosinolate"

项目 Item		总硫苷 Total gucosinolate	脂肪族硫苷总量 Total aliphatic glucosinolate	PRO	GRP	GAL	GNA	GBN	吲哚族硫苷总量 Total indole glucosinolate	4-OHGBS	GBS	MGBS	芳香族硫苷总量 Total aromatic glucosinolate	GST
低硫苷菜籽样品（硫苷含量 ≤40 µmol∙g^-1） Low sulfur glucoside rapeseed sample (sulfur glucoside content ≤40 µmol∙g^-1)	平均值(µmol∙g^-1) Glucosinolate mean (µmol∙g^-1)	29.73±3.54	24.58±3.08	6.28±1.38	0.12±0.02	0.83±0.23	17.35±1.45	0.00	5.01±0.43	4.46±0.59	0.33±0.07	0.21±0.09	0.14±0.03	0.14±0.03
	百分比 (%) percentage (%)	100.00	76.90	19.64	0.38	2.60	54.27	0.00	15.67	13.96	1.04	0.67	0.45	0.45
	变异系数 (%) Coefficient of variation (%)	11.91	12.52	21.95	18.37	27.67	8.34	0.00	8.67	13.14	19.91	39.73	22.74	22.74
	硫苷变异范围 Range of variation of glucosinolates	26.19—33.27	21.50—27.65	4.90—7.66	0.10—0.15	0.60—1.06	15.90—18.79	0.00	4.58—5.44	3.88—5.05	0.27—0.40	0.13—0.30	0.11—0.17	0.11—0.17
中硫苷菜籽样品（硫苷含量 41-80 µmol∙g^-1） Medium sulfur glucoside (with a content of 41-80 µmol∙g^-1)	平均值(µmol∙g^-1) Glucosinolate mean (µmol∙g^-1)	72.94±5.91	69.93±5.78	12.67±18.92	0.57±0.76	0.37±0.46	56.12±17.67	0.19±0.39	2.61±1.67	1.20±0.54	1.12±1.08	0.29±0.58	0.40±0.80	0.40±0.80
	百分比 (%) percentage (%)	100.00	95.86	17.38	0.78	0.51	76.94	0.27	3.58	1.65	1.54	0.40	0.55	0.55
	变异系数 (%) Coefficient of variation (%)	8.10	8.27	149.30	134.70	123.02	31.49	0.00	64.03	45.08	96.29	200.00	200.00	200.00
	硫苷变异范围 Range of variation of glucosinolates	61.87—78.83	61.24—76.24	1.86—50.14	0.91—1.92	0.86—1.00	23.19—72.13	0.97—0.97	0.64—5.61	0.40—1.89	0.23—3.23	1.46—1.46	2.01—2.01	2.01—2.01
高硫苷菜籽样品（硫苷含量81-100 µmol∙g^-1） High glucoside (with a content of 81-100 µmol∙g^-1)	平均值(µmol∙g^-1) Glucosinolate mean (µmol∙g^-1)	93.72±5.41	89.22±6.41	7.85±13.33	1.41±1.48	0.38±0.66	79.59±19.97	0.00	4.24±2.23	2.52±1.10	1.68±1.26	0.05±0.18	0.25±0.94	0.25±0.94
	百分比 (%) Percentage (%)	100.00	95.20	8.37	1.50	0.40	84.92	0.00	4.53	2.68	1.79	0.05	0.27	0.27
	变异系数 (%) Coefficient of variation (%)	5.77	7.19	169.83	105.32	173.75	25.09	0.00	52.53	43.56	75.21	374.17	374.17	374.17
	硫苷变异范围 Range of variation of glucosinolates	82.70—99.95	76.85—96.92	0.87—50.16	0.78—4.03	1.00—2.00	23.87—96.61	0.00	1.93—10.49	1.05—5.54	0.40—4.95	0.73—0.73	3.77—3.77	3.77—3.77
超高硫苷菜籽样品（硫苷含量 ≥101 µmol∙g^-1） Ultra high sulfur content (sulfur content ≥101 µmol∙g^-1)	平均值 (µmol∙g^-1) Glucosinolate mean (µmol∙g^-1)	141.17±25.74	134.70±25.79	5.82±5.60	1.39±1.84	0.28±0.64	126.63±27.87	0.59±1.39	5.98±3.87	3.05±1.64	2.79±2.52	0.14±0.46	0.49±1.21	0.49±1.21
	百分比 (%) Percentage (%)	100.00	95.42	4.12	0.99	0.20	89.70	0.42	4.23	2.16	1.97	0.10	0.34	0.34
	变异系数 (%) Coefficient of variation (%)	18.23	19.15	96.18	132.13	226.22	22.01	234.33	64.80	53.78	90.41	327.67	249.16	249.16
	硫苷变异范围 Range of variation of glucosinolates	100.02—238.21	88.68—225.66	0.82—68.38	0.41—8.86	0.47—4.52	56.11—217.77	0.89—7.45	0.91—18.97	0.64—8.38	0.22—14.28	0.14—5.82	0.49—6.96	0.49—6.96

Table 4

Fig. 3

Fig. 4

Table 5

Table 6

Total amount and content of various components of glucosinolates in winter and spring rapeseed"

	项目 Item	总硫苷 Total gucosinolate	脂肪族硫苷总量 Total aliphatic glucosinolate	PRO	GRP	GAL	GNA	GBN	吲哚族硫苷总量 Total indole glucosinolate	4-OHGBS	GBS	MGBS	芳香族硫苷总量 Total aromatic glucosinolate	GST
强冬性 Strong winter	硫苷均值 Glucosinolate mean (µmol∙g^-1)	133.51±21.97	121.14±21.02	9.30±3.96	3.63±1.30	0.89±0.77	105.15±20.33	2.18±1.90	11.50±2.10	5.23±0.98	6.01±1.64	0.25±0.35	0.87±1.17	0.87±1.17
	百分比 Percentage (%)	100.00	90.74	6.97	2.72	0.67	78.76	1.63	8.61	3.92	4.50	0.19	0.65	0.65
	变异系数 Coefficient of variation (%)	16.45	17.35	42.54	35.81	87.16	19.33	87.38	18.27	18.65	27.23	137.12	133.42	133.42
	极差 MAX-MIN	164.82	148.50	25.63	8.76	2.68	145.30	6.56	14.39	5.52	12.03	1.17	4.79	4.79
	硫苷变异范围 Range of variation of glucosinolates	26.19—191.00	21.50—170.00	4.34—29.96	0.10—8.86	0.60—3.28	15.90—161.20	0.89—7.45	4.58—18.97	2.48—8.00	0.40—12.43	0.14—1.31	0.11—4.90	0.11—4.90
冬性 Winter	硫苷均值 Glucosinolate mean (µmol∙g^-1)	142.81±41.63	135.06±40.92	6.86±2.73	2.29±1.00	0.79±0.66	124.36±40.77	0.75±1.26	7.60±1.93	3.07±0.77	4.41±1.59	0.11±0.39	0.15±0.54	0.15±0.54
	百分比 Percentage (%)	100.00	94.57	4.81	1.60	0.55	87.08	0.53	5.32	2.15	3.09	0.08	0.11	0.11
	变异系数 Coefficient of variation (%)	29.15	30.29	39.73	43.54	83.28	32.79	167.76	25.33	25.02	36.06	346.41	346.41	346.41
	极差 MAX-MIN	131.31	131.60	9.60	2.65	0.90	139.04	2.54	6.36	3.32	4.96	0.00	0.00	0.00
	硫苷变异范围 Range of variation of glucosinolates	72.59—203.90	64.98—196.57	2.29—11.90	0.91—3.57	0.86—1.76	54.13—193.17	0.97—3.51	4.88—11.24	0.91—4.24	2.23—7.19	1.46—1.46	2.01—2.01	2.01—2.01
半冬性 Semi- Winter	硫苷均值 Glucosinolate mean (µmol∙g^-1)	185.48±31.90	178.25±30.14	2.80±2.22	0.89±1.19	0.00	174.25±29.62	0.35±0.85	6.77±4.32	1.41±0.81	5.08±4.64	0.28±0.75	0.46±1.22	0.46±1.22
	百分比 Percentage (%)	100.00	96.10	1.51	0.48	0.00	93.94	0.19	3.65	0.76	2.74	0.15	0.25	0.25
	变异系数 Coefficient of variation (%)	17.20	16.91	78.99	133.16	0.00	17.00	244.95	63.80	57.19	91.37	264.58	264.58	264.58
	极差 MAX-MIN	99.59	90.79	6.41	3.10	0.00	84.99	0.00	12.94	2.50	12.88	0.00	0.00	0.00
	硫苷变异范围 Range of variation of glucosinolates	138.62—238.21	134.87—225.66	0.82—7.23	0.41—3.51	0.00	132.78—217.77	2.42—2.42	2.36—15.30	0.89—3.39	1.40—14.28	2.25—2.25	3.70—3.70	3.70—3.70
春性 Spring	硫苷均值 Glucosinolate mean (µmol∙g^-1)	136.41±28.89	132.18±28.51	5.03±7.18	0.59±1.29	0.08±0.42	126.46±30.47	0.03±0.41	3.87±1.97	2.34±1.12	1.43±1.18	0.10±0.46	0.36±1.20	0.36±1.20
	百分比 Percentage (%)	100.00	96.90	3.68	0.44	0.06	92.71	0.02	2.84	1.71	1.05	0.07	0.26	0.26
	变异系数 Coefficient of variation (%)	21.18	21.57	142.96	217.61	532.31	24.10	1506.65	50.77	47.82	82.11	474.54	332.84	332.84
	极差 MAX-MIN	188.30	182.87	67.51	8.68	4.04	185.59	0.00	18.32	7.97	10.36	5.69	6.79	6.79
	硫苷变异范围 Range of variation of glucosinolates	33.27—221.57	27.65—210.52	0.87—68.38	0.15—8.83	0.47—4.52	18.79—204.38	6.14—6.14	0.64—18.96	0.40—8.38	0.22—10.58	0.13—5.82	0.17—6.96	0.17—6.96

Table 6

Table 7

Statistical analysis of various sulfur glycoside contents in different ecological regions"

	项目 Item	总硫苷 Total gucosinolates	脂肪族硫苷总量 Total aliphatic glucosinolates	PRO	GRP	GAL	GNA	GBN	吲哚族硫苷总量 Total indole glucosinolate	4-OHGBS	GBS	MGBS	芳香族硫苷总量 Total aromatic glucosinolate	GST
长江流域 Yangtze river basin	硫苷均值 Glucosinolate mean (µmol∙g^-1)	162.00±32.61	154.75±32.79	3.87±6.28	1.21±1.87	0.17±0.57	149.36±36.52	0.14±0.57	7.17±3.37	2.73±1.80	4.33±3.38	0.11±0.43	0.09±0.37	0.09±0.37
	百分比 percentage (%)	100.00	95.52	2.39	0.74	0.10	92.20	0.09	4.42	1.68	2.67	0.07	0.06	0.06
	变异系数 Coefficient of variation (%)	20.13	21.19	162.28	154.86	336.32	24.45	400.00	47.06	65.99	77.99	400.00	400.00	400.00
	极差 MAX-MIN	125.95	118.98	26.99	4.38	1.91	143.24	0.00	12.09	5.18	13.56	0.00	0.00	0.00
	硫苷变异范围 Range of variation of glucosinolates	112.26—238.21	106.68—225.66	0.82—27.81	1.48—5.87	0.47—2.39	74.53—217.77	2.42—2.42	3.20—15.30	0.89—6.08	0.72—14.28	1.82—1.82	1.55—1.55	1.55—1.55
黄淮区 Huang- Huai Region	硫苷均值 Glucosinolate mean (µmol∙g^-1)	157.24±39.67	149.96±39.16	6.14±3.04	2.07±1.14	0.63±0.69	140.54±40.32	0.59±1.21	7.03±2.32	2.86±0.92	4.03±1.78	0.15±0.56	0.25±0.92	0.25±0.92
	百分比 Percentage (%)	100.00	95.37	3.91	1.31	0.40	89.38	0.37	4.47	1.82	2.56	0.10	0.16	0.16
	变异系数 Coefficient of variation (%)	25.23	26.11	49.44	54.93	109.68	28.69	205.90	32.99	32.11	44.20	374.17	374.17	374.17
	极差 MAX-MIN	133.81	131.24	10.82	3.16	0.66	136.92	1.47	8.88	3.28	5.79	0.00	0.00	0.00
	硫苷变异范围 Range of variation of glucosinolates	87.43—221.25	81.39—212.63	1.07—11.90	0.41—3.57	1.10—1.76	74.64—211.56	2.04—3.51	2.36—11.24	0.96—4.24	1.40—7.19	2.25—2.25	3.70—3.70	3.70—3.70
甘肃 Gansu	硫苷均值 Glucosinolate mean (µmol∙g^-1)	134.13±22.73	121.77±21.98	10.00±7.74	3.63±1.39	0.94±0.87	105.14±22.53	2.07±1.91	11.50±2.27	5.23±1.05	5.95±1.85	0.32±0.72	0.86±1.16	0.86±1.16
	百分比 Percentage (%)	100.00	90.79	7.46	2.70	0.70	78.38	1.54	8.57	3.90	4.43	0.24	0.64	0.64
	变异系数 Coefficient of variation (%)	16.95	18.05	77.32	38.44	92.77	21.43	92.67	19.77	20.08	31.10	220.49	135.09	135.09
	极差 MAX-MIN	172.48	166.68	64.99	8.76	3.92	167.69	6.56	14.39	5.89	12.03	5.68	4.79	4.79
	硫苷变异范围 Range of variation of glucosinolates	26.19—198.67	21.50—188.18	3.39—68.38	0.10—8.86	0.60—4.52	15.90—183.59	0.89—7.45	4.58—18.97	2.48—8.38	0.40—12.43	0.14—5.82	0.11—4.90	0.11—4.90
西藏 Xizang	硫苷均值 Glucosinolate mean (µmol∙g^-1)	135.76±27.79	131.86±27.32	4.70±5.78	0.48±1.09	0.03±0.19	126.67±28.58	0.00	3.53±1.27	2.20±0.89	1.26±0.80	0.06±0.25	0.37±1.23	0.37±1.23
	百分比 Percentage (%)	100.00	97.13	3.46	0.35	0.02	93.30	0.00	2.60	1.62	0.93	0.05	0.27	0.27
	变异系数 Coefficient of variation (%)	20.47	20.72	123.06	225.35	748.02	22.56	0.00	35.86	40.34	63.18	379.19	335.11	335.11
	极差 MAX-MIN	159.70	149.28	49.29	8.25	1.00	181.19	0.00	7.88	5.72	4.98	1.51	5.80	5.80
	硫苷变异范围 Range of variation of glucosinolates	61.87—221.57	61.24—210.52	0.87—50.16	0.58—8.83	1.00—2.00	23.19—204.38	0.00	0.64—8.52	0.40—6.12	0.22—5.20	0.36—1.87	1.16—6.96	1.16—6.96

Table 7

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硫苷类别 Aliphatic glucosinolate	硫苷名称 Name of glucosinolate	相对校正系数 Response facto (ƒ)	缩写 Abbreviation
脂肪族硫苷 Aliphatic glucosinolate	2-羟基-3-丁烯基硫苷 Progoitrin	1.09	PRO
	4-甲亚砜丁基硫苷 Glucoraphanin	1.07	GRP
	2-羟基-4-戊烯基硫苷 Gluconapoleiferin	1.00	GAL
	3-丁烯基硫苷 Gluconapin	1.11	GNA
	4-戊烯基硫苷 Glucobrassicanapin	1.15	GBN
吲哚族硫苷 Indole glucosinolate	4-羟基-3-吲哚甲基硫苷 4-hydroxyglucobrassicin	0.28	4-OHGBS
	3-吲哚甲基硫苷 Glucobrassicin	0.29	GBS
	4-甲氧基-3-吲哚甲基硫苷 4-methoxyglucobrassicin	0.25	MGBS
芳香族硫苷 Aromatic glucosinolate	苯乙基硫苷 Gluconasturtiin	0.95	GST

硫苷 Glucosinolate	硫苷变异范围 Variation range of glucosinolate	硫苷均值 Glucosinolate mean (µmol∙g^-1)	占总硫苷含量的百分比 Percentage (%)	变异系数 Coefficient of variation (%)	极差 MAX-MIN
总硫苷 Total gucosinolate	26.19—238.21	137.22±29.28	100.00	21.34	212.02
脂肪族硫苷总量 Total aliphatic glucosinolate	21.50—225.66	130.91±29.05	95.40	22.19	204.16
2-羟基-3-丁烯基硫苷Progoitrin	0.82—68.38	6.02±6.63	4.39	109.98	67.56
4-甲亚砜丁基硫苷Glucoraphanin	0.10—8.86	1.37±1.81	1.00	132.07	8.76
2-羟基-4-戊烯基硫苷Gluconapoleiferin	0.47—4.52	0.29±0.63	0.21	218.54	4.04
3-丁烯基硫苷 Gluconapin	15.90—217.77	122.68±31.39	89.40	25.59	201.87
4-戊烯基硫苷Glucobrassicanapin	0.89—7.45	0.56±1.35	0.40	243.37	6.56
吲哚族硫苷总量 Total indole glucosinolate	0.64—18.97	5.84±3.82	4.26	65.39	18.33
4-羟基-3-吲哚甲基硫苷 4-hydroxyglucobrassicin	0.40—8.38	3.01±1.63	2.19	54.13	7.97
3-吲哚甲基硫苷 Glucobrassicin	0.22—14.28	2.69±2.48	1.96	91.94	14.06
4-甲氧基-3-吲哚甲基硫苷 4-methoxyglucobrassicin	0.13—5.82	0.14 ±0.45	0.10	325.73	5.69
芳香族硫苷总量 Total aromatic glucosinolates	0.11—6.96	0.47±1.19	0.34	252.70	6.85
苯乙基硫苷 Gluconasturtiin	0.11—6.96	0.47±1.19	0.34	252.70	6.85

Analysis of Glucosinolate Content and Component in Brassica rapa L.

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项目 Item	总硫苷 Total gucosinolate	2-羟基-3- 丁烯基硫苷Progoitrin	4-甲亚砜丁基硫苷Glucoraphanin	2-羟基-4- 戊烯基硫苷Glucon- apoleiferin	3-丁烯基硫苷 Gluconapin	4-羟基-3- 吲哚甲基硫苷 4-hydroxyglu- cobrassicin	4-戊烯基硫苷Glucobrassi- canapin	3-吲哚甲基硫苷 Gluco- brassicin	苯乙基硫苷 Gluconas- turtiin	4-甲氧基-3- 吲哚甲基硫苷 4-methoxyglu- cobrassicin	脂肪族硫苷总量 Total aliphatic glucosinolates	吲哚族硫苷总量 Total indole glucosinolate
2-羟基-3-丁烯基硫苷Progoitrin	-0.06
4-甲亚砜丁基硫苷Glucoraphanin	-0.05	0.35
2-羟基-4-戊烯基硫苷Gluconapoleiferin	-0.07	0.62	0.54
3-丁烯基硫苷 Gluconapin	0.93**	-0.36	-0.32	-0.35
4-羟基-3-吲哚甲基硫苷4-hydroxyglucobrassicin	0.02	0.29	0.63	0.54	-0.22
4-戊烯基硫苷Glucobrassicanapin	0.05	0.19	0.57	0.48	-0.16	0.53
3-吲哚甲基硫苷 Glucobrassicin	0.12	0.28	0.83**	0.56	-0.16	0.64	0.62
苯乙基硫苷 Gluconasturtiin	0.11	0.10	0.19	0.19	0.00	0.14	0.15	0.13
4-甲氧基-3-吲哚甲基硫苷4-methoxyglucobrassicin	0.15	0.07	0.16	0.17	0.06	0.13	0.13	0.11	0.49
脂肪族硫苷总量 Total aliphatic glucosinolates	0.99**	-0.11	-0.17	-0.16	0.96**	-0.09	-0.04	-0.01	0.04	0.10
吲哚族硫苷总量 Total indole glucosinolate	0.10	0.32	0.82**	0.61	-0.19	0.86**	0.65	0.93**	0.20	0.24	-0.03
芳香族硫苷总量 Total aromatic glucosinolates	0.11	0.10	0.19	0.19	0.00	0.14	0.15	0.13	1.00**	0.49	0.04	0.20

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时间 Time (min)	流量 Flow rate (mL·min^-1)	流动相A Mobile phase A (%)	流动相B Mobile phase B (%)
0	1	85.0	15.0
10	1	0.0	100.0
12	1	0.0	100.0
15	1	85.0	15.0
20	1	85.0	15.0