HPLC-MS结合多元统计分析区分人参产地及筛选皂苷类标志物

doi:10.7503/cjcu20180452

高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (2): 246.doi: 10.7503/cjcu20180452

HPLC-MS结合多元统计分析区分人参产地及筛选皂苷类标志物

赵幻希¹, 王秋颖¹, 孙秀丽¹, 李雪¹, 苗瑞¹, 吴冬雪¹, 刘淑莹^1,²(), 修洋¹()

1. 长春中医药大学吉林省人参科学研究院, 长春 130117
2. 中国科学院长春应用化学研究所, 长春 130022

收稿日期:2018-06-22 出版日期:2019-02-10 发布日期:2018-12-27
作者简介:
联系人简介: 修洋, 男, 博士, 助理研究员, 主要从事中药化学方面的研究. E-mail: ys830805@sina.com;刘淑莹, 女, 博士, 教授, 博士生导师, 主要从事有机质谱方面的研究. E-mail: syliu@ciac.ac.cn
基金资助:
国家自然科学基金(批准号: 21475012)、吉林省科技发展计划项目(批准号: 20160520123JH, 20160309002YY)和长春中医药大学百青计划项目(批准号: 2017073)资助

Discrimination of Ginseng Origins and Identification of Ginsenoside Markers Based on HPLC-MS Combined with Multivariate Statistical Analysis^†

ZHAO Huanxi¹, WANG Qiuying¹, SUN Xiuli¹, LI Xue¹, MIAO Rui¹, WU Dongxue¹, LIU Shuying^1,^2,^*(), XIU Yang^1,^*()

1. Jilin Ginseng Academy, Changchun University of Chinese Medicine, Changchun 130117, China
2. Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

Received:2018-06-22 Online:2019-02-10 Published:2018-12-27
Contact: LIU Shuying,XIU Yang E-mail:syliu@ciac.ac.cn;ys830805@sina.com
Supported by:
† Supported by the National Natural Science Foundation of China(No.21475012), the Science and Technology Development Plan Project of Jilin Province, China(Nos.20160520123JH, 20160309002YY) and the Training Plan of Hundreds of Outstanding Teachers of Changchun University of Chinese Medicine(No.2017073)

摘要/Abstract

摘要：

利用高效液相色谱-质谱联用(HPLC-MS)技术结合多元统计分析方法, 区分中国人参主产区5个不同产地的45个人参样本, 筛选出差异性皂苷类标志物. 根据人参总皂苷在反相C₁₈色谱柱中的洗脱顺序, 结合串联质谱分析和标准品比对, 在提取的人参总皂苷中鉴定出15种原人参三醇型、 24种原人参二醇型和2种齐墩果酸型共41种皂苷. 对人参总皂苷的HPLC-MS全扫描数据进行了多元统计分析. 正交偏最小二乘-判别分析(OPLS-DA)结果表明, 所建立的分析模型具有良好的数据描述能力和预测能力. 所有人参样本能够根据产地被区分, 并筛选得到同时区分5个产地的差异性皂苷类组分18种; 能够区分任意2个产地人参样本的差异性组分主要为在人参中含量较高的人参皂苷Rb1, Rg1, Re, Rc, Rd, Ro和m-Rb1等. 分层聚类分析(HCA)结果显示, 黑龙江和吉林两省的样本能够独自聚类, 但是绥化市的样本更接近于吉林省. 初步推断原因为绥化市地理位置较接近吉林省, 两地人参生长环境相似并可能存在种质资源交换.

关键词: 高效液相色谱-质谱联用, 多元统计分析, 人参产地区分, 人参皂苷

Abstract:

High performance liquid chromatography-mass spectrometry combined with multi-variate statistical analysis was employed to discriminate 45 ginseng samples harvested from 5 different main cultivation areas in Northeast China and to identify the differential ginsenoside markers. A total of 41 ginsenosides, which included 15 protopanaxatriol type, 24 protopanaxadiol type and 2 oleanolic type ginsenosides, were identified based on the elution order of total ginsenosides in the reverse-phase C₁₈ column coupled with the tandem MS analysis and comparison with authentic standard. Multivariate statistical analysis was further used to extract the information of HPLC-MS data sets. Orthogonal partial least squares-discriminate analysis revealed that the established analysis model had high goodness of fit and predictability. All the 45 ginseng samples were discriminated according to their origins. And 18 ginsenosides were identified as the differential markers, which contri-buted most to the simultaneous discrimination of the 5 ginseng origins. In addition, the differential ginsenoside markers which could distinguish any two origins were mainly those of high content in wild ginseng, such as Rb1, Rg1, Re, Rc, Rd, Ro, and m-Rb1. In the results of hierarchical clustering analysis, the ginseng samples of Heilongjiang and Jilin Province gathered separately except for the samples from Suihua city, which showed similarity to those of Jilin Province. This discrepancy may be attributed to the geographical location. Suihua city is relatively closer to Jilin Province and hence results in the similar growth environment of ginseng and the facility to exchange germplasm resources.

Key words: High performance liquid chromatography-mass spectrometry(HPLC-MS), Multivariate statistical analysis, Discrimination of ginseng origin, Ginsenoside

中图分类号:

O657

TrendMD:

赵幻希, 王秋颖, 孙秀丽, 李雪, 苗瑞, 吴冬雪, 刘淑莹, 修洋. HPLC-MS结合多元统计分析区分人参产地及筛选皂苷类标志物. 高等学校化学学报, 2019, 40(2): 246.

ZHAO Huanxi,WANG Qiuying,SUN Xiuli,LI Xue,MIAO Rui,WU Dongxue,LIU Shuying,XIU Yang. Discrimination of Ginseng Origins and Identification of Ginsenoside Markers Based on HPLC-MS Combined with Multivariate Statistical Analysis^†. Chem. J. Chinese Universities, 2019, 40(2): 246.

图/表 9

参考文献 32

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No.	t_R/min	Ginsenoside	Molecular formula	[M-H]^- ion, m/z	Monoisotopic mass	Ref.
1	1.14	Re1	C₄₈H₈₂O₁₉	961.53	962.54	[23]
2	2.63	Re4	C₄₇H₈₀O₁₈	931.41	932.53	[30]
3	2.84	20-Glc-Rf	C₄₈H₈₂O₁₉	961.52	962.54	[23]
4	2.97	NG-R1 isomer	C₄₇H₈₀O₁₈	931.55	932.53	[23]
5	3.34	NG-R1	C₄₇H₈₀O₁₈	931.53	932.53	-
6	4.24	Re	C₄₈H₈₂O₁₈	945.52	946.55	-
7	4.30	Rg1	C₄₂H₇₂O₁₄	845.44	800.49	-
8	5.41	Ac-Rg1 isomer^a	C₄₄H₇₄O₁₅	841.46	842.50	[23]
9	6.00	m-Re	C₅₁H₈₄O₂₁	1031.56	1032.55	[30]
10	6.06	Ac-Re	C₅₀H₈₄O₁₉	987.54	988.56	[23]
11	6.31	Ac-Rg1	C₄₄H₇₄O₁₅	841.51	542.50	[23]
12	10.57	20(S)-Rf	C₄₂H₇₂O₁₄	799.44	800.49	-
13	10.73	Ra3	C₅₉H₁₀₀O₂₇	1239.64	1240.64	[30]
14	11.13	m-Ra3^b	C₆₂H₁₀₂O₃₀	1325.61	1326.65	[30]
15	11.47	20(S)-NG-R2	C₄₁H₇₀O₁₃	769.44	770.48	-
16	11.62	NG-R4	C₅₉H₁₀₀O₂₇	1239.67	1240.64	[30]
17	11.78	Ra2	C₅₈H₉₈O₂₆	1209.66	1210.63	[30]
18	11.81	m-NG-R4	C₆₂H₁₀₂O₃₀	1325.62	1236.65	[30]
19	11.93	NG-Fa	C₅₉H₁₀₀O₂₇	1239.66	1240.64	[30]
20	12.06	Rb1	C₅₄H₉₂O₂₃	1107.55	1108.60	-
No.	t_R/min	Ginsenoside	Molecular formula	[M-H]^- ion, m/z	Monoisotopic mass	Ref.
21	12.21	m-Ra2	C₆₁H₁₀₀O₂₉	1295.62	1296.63	[30]
22	12.33	20(S)-Rg2	C₄₂H₇₂O₁₃	783.47	784.50	-
23	12.40	m-NG-Fa	C₆₂H₁₀₂O₃₀	1325.59	1326.65	[30]
24	12.52	m-Rb1	C₅₇H₉₄O₂₆	1193.56	1194.60	[30]
25	12.71	Ra1	C₅₈H₉₈O₂₆	1209.56	1210.63	[30]
26	12.80	20(S)-Rh1	C₃₆H₆₂O₉	637.47	638.44	-
27	12.83	Rc	C₅₃H₉₀O₂₂	1077.61	1078.59	-
28	13.11	Ro	C₄₈H₇₆O₁₉	955.49	956.50	-
29	13.26	m-Ra1	C₆₁H₁₀₀O₂₉	1295.66	1296.63	[30]
30	13.42	m-Rc	C₅₆H₉₂O₂₅	1163.50	1164.59	[24]
31	13.66	Rb2	C₅₃H₉₀O₂₂	1077.57	1078.59	-
32	13.94	Rb3	C₅₃H₉₀O₂₂	1077.54	1078.59	-
33	14.19	Ra1 isomer	C₅₈H₉₈O₂₆	1209.58	1210.63	[23]
34	14.34	m-Rb2	C₅₆H₉₂O₂₅	1163.53	1164.59	[30]
35	14.65	m-Rb3	C₅₆H₉₂O₂₅	1163.78	1164.59	[30]
36	14.96	Quinquenoside R1	C₅₆H₉₄O₂₄	1149.62	1150.61	[30]
37	16.20	Rs2	C₅₅H₉₂O₂₃	1119.54	1120.60	[23]
38	16.42	Rd	C₄₈H₈₂O₁₈	945.48	946.55	-
39	16.63	Rs1	C₅₅H₉₂O₂₃	1119.72	1120.60	[23]
40	17.06	Chikusetsusaponin Ⅳa	C₄₂H₆₆O₁₄	793.41	794.44	[23]
41	17.56	m-Rd	C₅₁H₈₄O₂₁	1031.51	1032.55	[30]

No.	t_R/min	Ginsenoside	Molecular formula	[M-H]^- ion, m/z	Monoisotopic mass	Ref.
1	1.14	Re1	C₄₈H₈₂O₁₉	961.53	962.54	[23]
2	2.63	Re4	C₄₇H₈₀O₁₈	931.41	932.53	[30]
3	2.84	20-Glc-Rf	C₄₈H₈₂O₁₉	961.52	962.54	[23]
4	2.97	NG-R1 isomer	C₄₇H₈₀O₁₈	931.55	932.53	[23]
5	3.34	NG-R1	C₄₇H₈₀O₁₈	931.53	932.53	-
6	4.24	Re	C₄₈H₈₂O₁₈	945.52	946.55	-
7	4.30	Rg1	C₄₂H₇₂O₁₄	845.44	800.49	-
8	5.41	Ac-Rg1 isomer^a	C₄₄H₇₄O₁₅	841.46	842.50	[23]
9	6.00	m-Re	C₅₁H₈₄O₂₁	1031.56	1032.55	[30]
10	6.06	Ac-Re	C₅₀H₈₄O₁₉	987.54	988.56	[23]
11	6.31	Ac-Rg1	C₄₄H₇₄O₁₅	841.51	542.50	[23]
12	10.57	20(S)-Rf	C₄₂H₇₂O₁₄	799.44	800.49	-
13	10.73	Ra3	C₅₉H₁₀₀O₂₇	1239.64	1240.64	[30]
14	11.13	m-Ra3^b	C₆₂H₁₀₂O₃₀	1325.61	1326.65	[30]
15	11.47	20(S)-NG-R2	C₄₁H₇₀O₁₃	769.44	770.48	-
16	11.62	NG-R4	C₅₉H₁₀₀O₂₇	1239.67	1240.64	[30]
17	11.78	Ra2	C₅₈H₉₈O₂₆	1209.66	1210.63	[30]
18	11.81	m-NG-R4	C₆₂H₁₀₂O₃₀	1325.62	1236.65	[30]
19	11.93	NG-Fa	C₅₉H₁₀₀O₂₇	1239.66	1240.64	[30]
20	12.06	Rb1	C₅₄H₉₂O₂₃	1107.55	1108.60	-
No.	t_R/min	Ginsenoside	Molecular formula	[M-H]^- ion, m/z	Monoisotopic mass	Ref.
21	12.21	m-Ra2	C₆₁H₁₀₀O₂₉	1295.62	1296.63	[30]
22	12.33	20(S)-Rg2	C₄₂H₇₂O₁₃	783.47	784.50	-
23	12.40	m-NG-Fa	C₆₂H₁₀₂O₃₀	1325.59	1326.65	[30]
24	12.52	m-Rb1	C₅₇H₉₄O₂₆	1193.56	1194.60	[30]
25	12.71	Ra1	C₅₈H₉₈O₂₆	1209.56	1210.63	[30]
26	12.80	20(S)-Rh1	C₃₆H₆₂O₉	637.47	638.44	-
27	12.83	Rc	C₅₃H₉₀O₂₂	1077.61	1078.59	-
28	13.11	Ro	C₄₈H₇₆O₁₉	955.49	956.50	-
29	13.26	m-Ra1	C₆₁H₁₀₀O₂₉	1295.66	1296.63	[30]
30	13.42	m-Rc	C₅₆H₉₂O₂₅	1163.50	1164.59	[24]
31	13.66	Rb2	C₅₃H₉₀O₂₂	1077.57	1078.59	-
32	13.94	Rb3	C₅₃H₉₀O₂₂	1077.54	1078.59	-
33	14.19	Ra1 isomer	C₅₈H₉₈O₂₆	1209.58	1210.63	[23]
34	14.34	m-Rb2	C₅₆H₉₂O₂₅	1163.53	1164.59	[30]
35	14.65	m-Rb3	C₅₆H₉₂O₂₅	1163.78	1164.59	[30]
36	14.96	Quinquenoside R1	C₅₆H₉₄O₂₄	1149.62	1150.61	[30]
37	16.20	Rs2	C₅₅H₉₂O₂₃	1119.54	1120.60	[23]
38	16.42	Rd	C₄₈H₈₂O₁₈	945.48	946.55	-
39	16.63	Rs1	C₅₅H₉₂O₂₃	1119.72	1120.60	[23]
40	17.06	Chikusetsusaponin Ⅳa	C₄₂H₆₆O₁₄	793.41	794.44	[23]
41	17.56	m-Rd	C₅₁H₈₄O₂₁	1031.51	1032.55	[30]

No.	Variable	m/z@t_R	VIP	Molecular ion	Identity
1	2	1107.55@12.06	6.42	[M-H]^-	Rb1
2	3	955.47@13.11	6.03	[M-H]^-	Ro
3	7	1077.61@12.96	5.58	[M-H]^-	Rc
4	4	991.46@4.29	4.70	[M+HCOO]^-	Re
5	1	845.46@4.36	4.62	[M-H]^-	Rg1
6	9	991.49@16.43	4.45	[M+HCOO]^-	Rd
7	6	1123.50@12.56	4.10	[M+HCOO]^-	Rc
8	14	1193.53@12.52	3.87	[M-H]^-	m-Rb1
9	16	1163.49@13.43	3.73	[M-H]^-	m-Rc
10	15	945.52@16.41	3.56	[M-H]^-	Rd
11	12	1209.58@12.71	3.50	[M-H]^-	Ra1
12	5	799.49@10.57	3.27	[M-H]^-	20(S)-Rf
13	20	835.43@4.35	3.02	[M+Cl]^-	Rg1
14	34	1143.57@12.08	2.74	[M+Cl]^-	Rb1
15	18	1239.63@11.96	2.65	[M-H]^-	NG-Fa
16	32	1113.64@12.85	2.58	[M+Cl]^-	Rc
17	11	769.44@11.50	2.48	[M-H]^-	20(S)-NG-R2
18	8	1153.51@12.09	2.38	[M+HCOO]^-	Rb1
19	19	1255.63@11.76	2.34	[M+HCOO]^-	Ra2
20	39	981.41@16.66	2.25	[M+Cl]^-	Rd
21	36	793.41@17.00	2.20	[M-H]^-	Chikusetsusaponin Ⅳa
22	26	1285.55@11.98	2.19	[M+HCOO]^-	NG-Fa
23	10	945.50@4.28	2.14	[M-H]^-	Re
24	31	981.43@4.25	2.09	[M+Cl]^-	Re
25	37	1031.49@17.61	2.05	[M-H]^-	m-Rd
26	52	835.41@10.57	1.81	[M+Cl]^-	20(S)-Rf
27	54	1008.49@2.69	1.72	-	Unknown

No.	Variable	m/z@t_R	VIP	Molecular ion	Identity
1	2	1107.55@12.06	6.42	[M-H]^-	Rb1
2	3	955.47@13.11	6.03	[M-H]^-	Ro
3	7	1077.61@12.96	5.58	[M-H]^-	Rc
4	4	991.46@4.29	4.70	[M+HCOO]^-	Re
5	1	845.46@4.36	4.62	[M-H]^-	Rg1
6	9	991.49@16.43	4.45	[M+HCOO]^-	Rd
7	6	1123.50@12.56	4.10	[M+HCOO]^-	Rc
8	14	1193.53@12.52	3.87	[M-H]^-	m-Rb1
9	16	1163.49@13.43	3.73	[M-H]^-	m-Rc
10	15	945.52@16.41	3.56	[M-H]^-	Rd
11	12	1209.58@12.71	3.50	[M-H]^-	Ra1
12	5	799.49@10.57	3.27	[M-H]^-	20(S)-Rf
13	20	835.43@4.35	3.02	[M+Cl]^-	Rg1
14	34	1143.57@12.08	2.74	[M+Cl]^-	Rb1
15	18	1239.63@11.96	2.65	[M-H]^-	NG-Fa
16	32	1113.64@12.85	2.58	[M+Cl]^-	Rc
17	11	769.44@11.50	2.48	[M-H]^-	20(S)-NG-R2
18	8	1153.51@12.09	2.38	[M+HCOO]^-	Rb1
19	19	1255.63@11.76	2.34	[M+HCOO]^-	Ra2
20	39	981.41@16.66	2.25	[M+Cl]^-	Rd
21	36	793.41@17.00	2.20	[M-H]^-	Chikusetsusaponin Ⅳa
22	26	1285.55@11.98	2.19	[M+HCOO]^-	NG-Fa
23	10	945.50@4.28	2.14	[M-H]^-	Re
24	31	981.43@4.25	2.09	[M+Cl]^-	Re
25	37	1031.49@17.61	2.05	[M-H]^-	m-Rd
26	52	835.41@10.57	1.81	[M+Cl]^-	20(S)-Rf
27	54	1008.49@2.69	1.72	-	Unknown

Origin		Identity	Origin		Identity
XK	HL	Rb1, Rc, Rd, Rg1, Ro	HL	WQ	Rg1, Rb1, m-Rc, m-Rb1
	SH	Rd, Rc, Ro, Rg1		CB	Rg1, Rb1, Rc, Re, m-Rc, m-Rb1
	WQ	Rb1, Rc, Rf, Ra1, Re, m-Rb1	SH	WQ	Rb1, Rc, Rg1, Ro, Ra1, Re
	CB	Rc, Rb1, Rd, Rg1, m-Rc, m-Rb1, Ro		CB	Rb1, Rc, Rd, Rg1, Ra1, Rc, m-Rc
HL	SH	Rg1, Rb1, Rc, Re, m-Rb1	WQ	CB	Re, Rd, Rg1, m-Rc, Ro

HPLC-MS结合多元统计分析区分人参产地及筛选皂苷类标志物

Discrimination of Ginseng Origins and Identification of Ginsenoside Markers Based on HPLC-MS Combined with Multivariate Statistical Analysis^†

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HPLC-MS结合多元统计分析区分人参产地及筛选皂苷类标志物

Discrimination of Ginseng Origins and Identification of Ginsenoside Markers Based on HPLC-MS Combined with Multivariate Statistical Analysis†

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摘要/Abstract

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图/表 9

参考文献 32

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Discrimination of Ginseng Origins and Identification of Ginsenoside Markers Based on HPLC-MS Combined with Multivariate Statistical Analysis^†