经典名方温经汤基准样品HPLC-Q-TOF/MS分析与指纹图谱研究

汤志锋; 张云羽; 石德志; 高武锋; 龚小文; 嵇晶; 黄仕文; 程建明

doi:10.14148/j.issn.1672-0482.2023.0452

经典名方温经汤基准样品HPLC-Q-TOF/MS分析与指纹图谱研究

doi: 10.14148/j.issn.1672-0482.2023.0452

汤志锋^{1, 2,},
张云羽^{1, 2},
石德志^{1, 2},
高武锋^{1, 2},
龚小文^{1, 2},
嵇晶^{1, 2},
黄仕文^3, ,,
程建明^{1, 2, ,}

1.
南京中医药大学药学院, 江苏南京 210023
2.
江苏省经典名方工程研究中心, 江苏南京 210023
3.
南京中医药大学中医学院·中西医结合学院, 江苏南京 210023

基金项目:

江苏省自然科学基金 BK20181424

详细信息

作者简介:
汤志锋, 男, 硕士研究生, E-mail: 20200839@njucm.edu.cn

通讯作者:
黄仕文, 男, 副教授, 主要从事中药新剂型新技术及其产品开发研究, E-mail: hshw_66@163.com

程建明, 男, 研究员, 主要从事中药新剂型新技术及其产品开发研究, E-mail: cjm@njucm.edu.cn

中图分类号: R284
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- 被引次数: 0
出版历程
- 收稿日期: 2022-08-26
- 网络出版日期: 2023-05-19
- 发布日期: 2023-05-10

Study on HPLC-Q-TOF/MS Analysis and Fingerprint of Classic Prescription Wenjing Decoction Substance Benchmarks

TANG Zhi-feng^{1, 2
,},
ZHANG Yun-yu^{1, 2},
SHI De-zhi^{1, 2},
GAO Wu-feng^{1, 2},
GONG Xiao-wen^{1, 2},
JI Jing^{1, 2},
HUANG Shi-wen^{3
, ,},
CHENG Jian-ming^{1, 2
, ,}

1.
School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China
2.
Jiangsu Province Engineering Research Center of Classical Prescription, Nanjing 210023, China
3.
School of Chinese Medicine, School of Chinese Medicine and Intergrative Medicine, Nanjing University of Chinese Medicine, Nanjing 210023, China

摘要

摘要: 目的采用HPLC-Q-TOF/MS技术对温经汤基准样品化学成分进行表征, 同时建立经典名方温经汤基准样品指纹图谱, 并对其共有峰进行指认与归属。方法采用Agilent 5 TC-C₁₈(2)柱(250 mm×4.6 mm, 5 μm)色谱柱, 以乙腈-0.1%甲酸水为流动相进行梯度洗脱, 通过PeakView软件辅助解析, 快速鉴别出温经汤基准样品中化学成分, 并通过HPLC-UV及HPLC-ELSD法建立温经汤基准样品指纹图谱。结果温经汤基准样品中共分析鉴别出122个化合物, 并进行相关药味归属。建立的温经汤基准样品HPLC-UV指纹图谱有19个共有峰, 通过对照品比对, 指认出没食子酸、芍药苷、甘草酸、甘草苷、桂皮醛、丹皮酚、阿魏酸、藁本内酯、β-蜕皮甾酮9个色谱峰; HPLC-ELSD指纹图谱有8个共有峰, 通过对照品比对, 指认出人参皂苷Rg₁、人参皂苷Re和人参皂苷Rb₁。建立的HPLC-UV、HPLC-ELSD两张指纹图谱能够归属全方所有药味。结论通过UV、ELSD建立的指纹图谱方法灵敏度高, 稳定性和准确性良好, 全面反映了温经汤基准样品的整体特征, 为温经汤基准样品质量标准的建立提供了可靠的依据。
- 温经汤 /
- 指纹图谱 /
- HPLC-Q-TOF/MS /
- 化学成分
Abstract: OBJECTIVE To characterize the chemical composition of the benchmark sample of Wenjing Decoction (WJT) by establishing fingerprints of WJT benchmark sample and conduct the common peaks identification and attribution. METHODS Agilent 5 TC-C₁₈ (2) column (250 mm×4.6 mm, 5 μm) was adopted, and acetonitrile (A)-0.1% formic acid aqueous solution (B) was used as the mobile phase for gradient elution. Assisted analysis through PeakView software, the chemical composition in the benchmark sample of the WJT was quickly identified, and the fingerprint of the benchmark sample of WJT was established by HPLC-UV and HPLC-ELSD. RESULTS A total of 122 compounds were analyzed and identified by the benchmark sample of WJT, and the relevant herbs was attributed. The HPLC-UV fingerprint of benchmark sample of WJT had 19 common peaks, and 9 chromatographic peaks of gallic acid, paeoniflorin, glycyrrhizic acid, liquiritin, cinnamaldehyde, paeonol, ferulic acid, ligustilide and β-ecdysone were identified by comparison of reference substance. There were 8 common peaks in the HPLC-ELSD fingerprint, and ginsenoside Rg₁, ginsenoside Re, and ginsenoside Rb₁ were identified by comparison of reference substance. The two fingerprints of HPLC-UV and HPLC-ELSD established could belong to all herbs of the whole prescription. CONCLUSION The method established by UV and ELSD is of high sensitivity, good stability and accuracy, which comprehensively reflects the overall characteristics of the benchmark sample of the WJT. The study provides a reliable basis for the establishment of quality standards for the benchmark sample of WJT.
- Wenjing Decoction /
- fingerprint /
- HPLC-Q-TOF/MS /
- chemical composition

HTML全文

图 1 温经汤正(A)、负(B)离子模式下的总离子流图

Figure 1. Total ion chromatogram of WJT in positive (A) and negative (B) ion modes

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图 2 温经汤对照指纹图谱(R)及10批温经汤叠加图谱(S1~S10)

Figure 2. Reference fingerprint (R) and fingerprint of 10 batches of WJT (S1-S10)

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图 3 HPLC-UV混合对照品图(C)及温经汤对照指纹图谱(S1)对比图

注: 1.没食子酸; 3.芍药苷; 4.β-蜕皮甾酮; 6.甘草苷; 7.阿魏酸; 13.桂皮醛; 15.丹皮酚; 16.甘草酸; 19.藁本内酯

Figure 3. Comparison diagram of HPLC-UV mixed reference (C) and WJT reference fingerprint (S1)

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图 4 单味药材共有峰归属

注: S1.全方; S2.牛膝; S3.莪术; S4.肉桂; S5.甘草; S6.川芎; S7.当归; S8.川芎和当归; S9.白芍; S10.牡丹皮; S11.白芍和牡丹皮; S12.人参

Figure 4. Common peak attribution of single medicine materials

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图 5 温经汤对照指纹图谱(R)及10批温经汤ELSD叠加图谱(S1~S10)

Figure 5. HPLC reference fingerprint (R) and ELSD fingerprint of 10 batches of WJT (S1-S10)

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图 6 HPLC-ELSD对照品(Rg₁、Re、Rb₁)图及温经汤对照指纹图谱对比图

注: 2.人参皂苷Rg₁; 3.人参皂苷Re; 5.人参皂苷Rb₁

Figure 6. Comparison diagram of HPLC-ELSD of reference (Rg₁, Re, Rb₁) and WJT reference fingerprint

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表 1 温经汤基准样品饮片来源及批号信息

Table 1. The origin and batch number of herbal pieces from WJT substance benchmarks

饮片	拉丁名	产地	批号
当归(酒)	Angelica sinensis(Oliv.) Diels	甘肃岷县	DG-191204、22012201、22012202、22012203、22012204、22012205
川芎	Ligusticum chuanxiong Hort.	四川彭州市四川眉山市	CX-200901、22022001、22022002、22022003、22022004、22022005
肉桂	Cinnamomum cassia Presl	广西平南县	RG-200901、22022401、22022402、22022403、22022404、22022405
白芍	Paeonia lactiflora Pall.	安徽亳州市	BS-191202、22022701、22022702、22022703、22022704、22022705
牡丹皮	Paeonia suffruticosa Andr.	安徽铜陵市安徽谯城区	MDP-201001、22022301、22022302、22022303、22022304、22022305
莪术(醋)	Curcuma phaeocaulis VaL.	云南红河州	EZ-201001、22030101、22030102、22030103、22030104、22030105
人参	Panax ginseng C. A. Mey.	吉林长白县	RS-200601、22030301、22030302、22030303、22030304、22030305
甘草(炒)	Glycyrrhiza uralensis Fisch.	甘肃岷县	GC-201001、22030501、22030502、22030503、22030504、22030505
牛膝(酒)	Achyranthes bidentata Bl.	河南武陟县	NX-190703、22030201、22030202、22030203、22030204、22030205
注: DG-191204、CX-200901、RG-200901、BS-191202、MDP-201001、EZ-201001、RS-200601、GC-201001、NX-190703批次饮片均购自安徽省万生中药饮片有限公司, 其余批次饮片均由实验室炮制。

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表 2 温经汤基准样品HPLC-Q-TOF-MS分析

Table 2. HPLC-Q-TOF-MS analysis results of WJT substance benchmarks

峰号	分子式	t_R/min	加合离子类型	m/z (理论值)	m/z (实测值)	误差/×10^-6	主要碎片离子	化合物	来源
1	C₁₈H₂₈O₉	3.28	[M-H]^-	387.166 1	387.168 9	7.4	341.112 1, 179.058 0, 161.047 0, 119.036 5, 101.025 6, 89.026 0	川芎苷A	CX
2	C₆H₁₃NO₂	3.46	[M+H]⁺	132.101 9	132.101 8	-0.6	132.103 0, 58.070 8	异亮氨酸	DG
3	C₆H₁₂O₆	3.55	[M-H]^-	179.056 1	179.056 4	1.7	179.057 7, 161.047 3, 141.022 7, 99.010 2	葡萄糖	RS
4	C₁₂H₂₂O₁₁	4.06 4.05	[M+H]⁺ [M-H]^-	343.123 5 341.108 9	343.123 9 341.108 0	1.1 -2.7	163.061 8, 145.050 2, 73.031 3 341.111 8, 179.057 1, 119.036 1, 101.025 6, 89.025 6, 71.015 9, 59.016 8	麦芽糖	RS
5	C₅H₅N₅	4.22	[M+H]⁺	136.061 8	136.061 5	-2.0	136.063 0, 119.037 2, 92.027 5	腺嘌呤	CX
6	C₆H₈O₇	6.71	[M-H]^-	191.019 7	191.019 7	-0.2	191.021 7, 129.019 9, 87.010 5	枸橼酸	RS
7	C₉H₁₂N₂O₆	7.19	[M-H]^-	243.062 3	243.062 2	-0.1	243.063 3, 200.058 2, 110.026 6	尿苷	GC
8	C₁₀H₁₃N₅O₄	7.63	[M+H]⁺	268.104 0	268.103 9	-0.6	136.062 6, 119.036 4	腺苷	RS
9	C₁₃H₁₆O₁₀	8.35	[M-H]^-	331.067 1	331.066 7	-1.0	331.071 0, 271.050 4, 211.027 2, 169.015 6, 151.004 3, 125.026 0	没食子酰葡萄糖	MDP
10	C₇H₆O₅	10.04 10.07	[M+H]⁺ [M-H]^-	171.028 8 169.014 3	171.028 6 169.014 7	-1.0 2.5	171.029 3, 153.019 9, 125.024 7, 107.014 6 169.017 1, 125.026 4, 124.018 7	没食子酸^*	MDP
11	C₇H₆O₄	14.39	[M-H]^-	153.019 3	153.019 6	1.8	153.021 1, 109.031 0, 91.020 6	原儿茶酸	GC
12	C₁₈H₂₄O₈	16.49	[M+H]⁺	369.154 4	369.152 7	-4.7	369.152 6	Celephthalide A	CX
13	C₂₃H₂₈O₁₂	17.00 17.02	[M+NH₄]⁺ [M-H]^-	514.191 9 495.150 8	514.192 4 495.147 7	1.0 -6.2	197.081 5, 179.070 5, 139.039 8 301.074 7, 191.036 9, 150.033 8, 121.031 0	氧化芍药苷	BS
14	C₁₆H₁₈O₉	17.67	[M+Na]⁺	377.084 3	377.084 4	0.2	377.084 6, 215.053 2	绿原酸	DG
15	C₇H₆O₃	17.72	[M-H]^-	137.024 4	137.024 7	2.0	137.025 9, 92.028 0	对羟基苯甲酸	MDP
16	C₁₅H₁₄O₆	18.06 18.09	[M+H]⁺ [M-H]^-	291.086 3 289.071 8	291.086 6 289.071 4	1.0 -1.2	207.066 0, 165.054 7, 139.039 7, 123.045 7, 111.045 8 289.075 6, 205.053 1, 179.037 7, 163.041 7, 149.026 8, 137.026 1, 125.026 4, 109.031 0	儿茶素	BS, MDP
17	C₈H₈O₅	18.36	[M-H]^-	183.029 9	183.030 1	0.9	183.031 6, 168.008 1, 140.012 6, 124.018 5	没食子酸甲酯	MDP
18	C₂₇H₃₀O₁₅	19.53 19.54	[M+H]⁺ [M-H]^-	595.165 8 593.151 2	595.165 8 593.148 3	0.5 -4.9	595.166 4, 577.1547, 559.144 2, 433.093 3, 283.054 7 593.156 8, 503.123 3, 473.115 8, 353.070 3	山柰酚-3-O-芸香糖苷	GC
19	C₇H₆O₂	19.79	[M-H]^-	121.029 5	121.030 1	4.6	121.033 1, 77.041 4	苯甲酸	BS, MDP
20	C₈H₆O₄	19.79	[M-H]^-	165.019 3	165.019 5	0.9	121.032 0, 77.042 2	邻苯二甲酸	DG
21	C₂₀H₂₈O₁₂	20.18	[M-H]^-	459.150 8	459.148 7	-4.5	459.153 4, 165.057 4, 147.044 1	牡丹酚原苷	MDP
22	C₈H₈O₄	20.20	[M-H]^-	167.035 0	167.035 4	2.7	167.038 5, 152.011 6, 123.047 1, 121.030 4	香荚兰酸	CX
23	C₉H₈O₄	20.44	[M-H]^-	179.035 0	179.035 3	1.5	179.038 2, 135.046 8, 134.039 1	咖啡酸	CX
24	C₂₁H₂₂O₁₁	20.95	[M-H]^-	449.108 9	449.106 3	-6.0	413.939 2, 160.843 0	二氢槲皮素-7-O-鼠李糖苷	GC
25	C₂₃H₂₈O₁₁	21.06	[M-H]^-	479.155 9	479.154 2	-3.5	479.156 5, 121.029 6, 77.988 0	芍药内酯苷	BS
26	C₂₃H₂₈O₁₁	21.06 22.24	[M+H]⁺ [M-H]^-	481.170 4 479.155 9	481.170 9 479.152 6	0.9 -6.9	319.118 4, 301.107 5, 197.081 6, 105.035 7 479.163 9, 449.147 6, 327.111 5, 165.057 5, 121.031 0, 77.041 7	芍药苷^*	BS
27	C₃₀H₃₂O₁₆	21.23 21.25	[M+Na]⁺ [M-H]^-	671.158 3 647.161 8	671.159 1 647.158 7	1.3 -4.8	503.153 9, 341.101 4 647.167 9, 629.155 8, 509.134 0, 491.125 7, 399.096 4, 313.058 8, 271.027 7, 211.027 7	没食子酰氧化芍药苷	BS, MDP
28	C₂₇H₂₄O₁₈	21.33 21.34	[M+Na]⁺ [M-H]^-	659.096 3 635.089 0	659.086 6 635.085 6	1.6 -5.3	659.087 1, 489.067 3 635.095 7, 483.082 8, 465.072 0, 313.059 9, 169.015 9, 125.024 9	1, 3, 6-三没食子酰葡萄糖	MDP
29	C₂₆H₂₈O₁₄	21.49 21.50	[M+H]⁺ [M-H]^-	565.155 2 563.140 6	565.155 6 563.137 3	0.7 -6.0	565.154 5, 547.143 3, 409.093 0, 309.080 0 563.145 6, 473.114 2, 443.102 6, 383.081 1	芹菜苷	GC
30	C₉H₁₀O₂	22.24	[M+H]⁺	151.075 4	151.074 9	-2.9	95.088 0, 81.035 0, 67.057 2	3-甲氧基-4-羟基苯乙烯	CX
31	C₁₀H₁₀O₃	22.24	[M+H]⁺	179.063 0	179.070 3	-0.8	179.071 6, 161.060 7, 133.066 6	松柏醛	RG
32	C₂₄H₃₀O₁₃	22.27	[M-H]^-	525.161 4	525.157 5	-7.4	525.166 4, 327.110 6, 165.057 1	牡丹皮苷E	MDP
33	C₂₇H₃₂O₁₄	23.17 22.58	[M+H]⁺ [M-H]^-	581.186 5 579.171 9	581.186 7 579.167 9	0.5 -7.0	581.186 2, 257.080 4 579.176 8, 255.068 5, 135.011 1, 119.051 6	柚皮苷	GC
34	C₂₁H₂₀O₉	23.31	[M+H]⁺	417.118 0	417.118 2	0.4	417.116 8, 255.065 1	异黄酮苷	GC
35	C₂₇H₃₀O₁₄	23.51 23.52	[M+H]⁺ [M-H]^-	579.170 8 577.156 3	579.170 6 577.152 6	-0.5 -6.3	579.170 6, 561.160 3, 543.152 1 577.160 4, 457.116 3, 413.088 8, 383.079 5	野漆树苷	MDP
36	C₃₄H₂₈O₂₂	23.89 23.91	[M+Na]⁺ [M-H]^-	811.096 4 787.100 0	811.097 2 787.095 8	0.9 -5.3	811.098 4, 641.077 5, 471.053 0, 301.032 5 787.108 0, 635.094 3, 617.084 3, 465.072 2, 169.016 0	1, 2, 3, 6-四没食子酰葡萄糖	MDP
37	C₂₇H₄₄O₇	24.19	[M+H]⁺	481.316 0	481.315 9	-0.1	481.313 9, 463.307 4, 445.296 3, 301.180 7	β-蜕皮甾酮^*	NX
38	C₂₇H₃₂O₁₆	24.35	[M-H]^-	611.161 8	611.157 9	-6.3	611.168 3, 445.103 4, 169.016 7, 165.057 1, 125.025 4	牡丹苷A/C	MDP
39	C₁₅H₁₂O₄	24.70	[M+H]⁺	257.080 8	257.080 9	0.2	257.080 8, 147.044 7, 137.023 8, 119.050 8	甘草素	GC
40	C₂₆H₃₀O₁₃	24.74	[M-H]^-	549.161 4	549.157 3	-7.5	549.165 8, 255.068 1, 135.010 1, 119.051 8	芹糖甘草苷	GC
41	C₁₅H₂₂O₄	25.00	[M+H]⁺	267.159 1	267.159 0	-0.3	249.149 1, 231.129 8, 69.071 7	Verrucarol	EZ
42	C₂₁H₂₂O₉	25.30 25.34	[M+H]⁺ [M-H]^-	419.133 7 417.119 1	419.134 2 417.116 6	1.3 -6.0	257.081 2, 239.070 4, 147.044 3, 137.024 2 417.122 1, 254.068 3, 135.010 3, 119.051 9, 91.021 0	甘草苷^*	GC
43	C₁₅H₁₂O₄	25.32	[M+H]⁺	257.080 8	257.080 7	-0.7	257.081 3, 147.044 3, 137.0241, 119.049 9, 91.056 4	乔松素	GC
44	C₄₁H₃₂O₂₆	25.78 25.80	[M+NH₄]⁺ [M-H]^-	958.152 0 939.110 9	958.153 2 939.105 1	1.2 -6.2	771.1031, 153.0190, 125.0241 939.120 5, 769.096 6, 617.085 0, 601.088 3, 169.016 2	五没食子酰葡萄糖	BS, MDP
45	C₃₀H₃₂O₁₅	25.81 25.84	[M+NH₄]⁺ [M-H]^-	650.208 0 631.166 8	650.207 6 631.162 6	-0.5 -6.7	493.135 3, 315.072 2, 297.062 8, 153.019 5, 127.041 4 297.078 8, 255.068 1	没食子酰芍药苷	BS, MDP
46	C₁₀H₁₀O₄	26.37 26.38	[M+H]⁺ [M-H]^-	195.065 2 193.050 6	195.065 1 193.050 6	-0.6 0.0	177.055 8, 149.060 0, 145.028 3, 134.036 5, 117.034 3 193.052 8, 178.029 4, 149.061 8, 134.038 8	阿魏酸^*	CX, DG
47	C₃₀H₃₂O₁₄	27.42 27.43	[M+NH₄]⁺ [M-H]^-	634.213 0 615.171 9	634.212 8 615.167 5	-0.4 -7.2	283.083 0, 265.072 5, 139.040 1, 121.027 5 615.178 0, 281.069 4, 137.026 8	牡丹皮苷H	MDP
48	C₂₁H₂₀O₁₀	28.85	[M+H]⁺	433.112 9	433.112 9	-0.1	271.060 2, 153.018 4	牡荆素	GC
49	C₁₅H₁₂O₅	29.16	[M+H]⁺	273.075 8	273.075 7	-0.4	273.077 7, 153.018 5, 147.045 0, 119.052 7, 69.034 7	柚皮素	GC
50	C₁₅H₁₀O₅	29.20	[M-H]^-	269.045 6	269.044 7	-3.3	269.047 2, 133.031 4	芹菜素	GC
51	C₂₄H₃₀O₁₂	29.43	[M-H]^-	509.166 5	509.162 5	-7.8	509.172 3, 341.128 1, 121.031 5, 77.039 8	牡丹皮苷D	MDP
52	C₁₆H₁₄O₆	29.59 29.60	[M+H]⁺ [M-H]^-	303.790 4 301.071 8	303.086 2 301.070 4	-0.2 -4.7	303.087 1, 261.075 9, 193.049 9, 178.026 9, 163.038 9, 150.031 8, 139.039 9, 137.024 1, 123.044 4 301.074 7, 286.051 4, 161.026 4, 150.033 8	橙皮素	GC
53	C₉H₁₆O₄	29.88	[M-H]^-	187.097 6	187.097 4	-1.1	187.098 5, 169.089 2, 125.098 5	壬二酸	DG
54	C₄₈H₈₂O₁₈	29.97	[M+Na]⁺	969.539 3	969.538 5	0.5	969.536 5	人参皂苷Re^*	RS
55	C₈H₈O₃	30.50	[M-H]^-	151.040 1	151.040 2	0.6	151.038 1, 135.009 9, 109.030 7, 91.020 6	香草醛	CX
56	C₂₂H₂₆O₁₁	30.93	[M+Na]⁺	489.136 7	489.138 4	3.5	285.076 5, 270.053 2	仙茅苷	GC
57	C₁₂H₁₄O₃	31.31	[M+H]⁺	207.101 6	207.101 3	-1.5	207.101 2, 189.090 9, 165.054 7, 123.044 1, 95.052 6, 67.058 1	4-羟基-3-丁基苯酞	CX
58	C₂₂H₂₂O₉	31.58	[M+H]⁺	431.133 7	431.133 3	-0.8	269.081 1, 254.058 1, 237.055 2	芒柄花苷	GC
59	C₃₀H₃₂O₁₃	31.80	[M+NH₄]⁺	618.218 1	618.217 9	-0.3	283.080 3, 265.070 6, 179.070 0, 139.038 9, 121.029 9	牡丹皮苷C	MDP
60	C₃₁H₃₄O₁₄	31.88	[M+NH₄]⁺	648.228 7	648.228 8	0.2	313.093 0, 295.082 5, 169.050 7, 151.039 8	牡丹皮苷J	MDP
61	C₁₅H₁₀O₄	32.82 32.83	[M+H]⁺ [M-H]^-	255.065 2 253.050 6	255.065 0 253.049 5	-0.9 -4.3	255.065 0, 145.028 8, 137.024 1 253.052 3, 135.009 5, 117.036 0, 91.019 8	7, 4′-二羟基黄酮	GC
62	C₃₀H₃₂O₁₃	33.17	[M+NH₄]⁺	618.218 1	618.216 6	-2.5	445.156 2, 317.103 3, 267.087 1, 249.076 9, 179.070 3, 105.035 6	苯甲酰氧化芍药苷	BS
63	C₁₆H₁₄O₅	33.84 33.86	[M+H]⁺ [M-H]^-	287.091 4 285.076 9	287.091 2 285.075 6	-0.6 -4.3	287.091 6, 245.081 3, 193.049 1, 150.032 0, 121.029 8 285.079 4, 270.055 6, 177.021 5, 150.033 8, 121.023 3	甘草查尔酮B	GC
64	C₁₆H₁₂O₆	35.06 35.06	[M+H]⁺ [M-H]^-	301.070 7 299.056 1	301.070 6 299.054 8	-0.2 -4.4	301.071 4, 273.104 7, 258.057 0, 139.041 9, 123.043 8 299.058 6, 284.035 6, 256.040 2	3-(2, 4-二羟基苯基)-7-羟基-5-甲氧基-2H-1-苯并吡喃-2-酮	GC
65	C₁₅H₁₂O₄	35.14	[M-H]^-	255.066 3	255.065 6	-2.8	255.067 8, 135.010 6, 119.051 8, 91.021 1	异甘草素	GC
66	C₁₆H₁₂O₅	35.81 35.83	[M+H]⁺ [M-H]^-	285.075 8 283.061 2	285.076 1 283.059 5	0.5 -5.9	285.075 8, 270.053 4, 269.043 2, 253.048 8, 213.055 5, 137.023 6 283.062 8, 268.038 8, 267.031 2, 239.036 8, 211.042 2	毛蕊异黄酮	GC
67	C₁₅H₁₀O₇	36.22	[M-H]^-	301.035 4	301.034 1	-4.2	301.037 8, 273.037 5, 151.005 6, 121.030 4, 107.016 2, 93.034 8	槲皮素	GC
68	C₄₂H₇₂O₁₄	37.62	[M-H]^-	799.484 9	499.478 0	-8.7	799.493 4, 637.438 5, 475.387 0	人参皂苷Rg₁^*	RS
69	C₃₀H₃₂O₁₂	37.69 37.70	[M+NH₄]⁺ [M-H]^-	602.223 2 583.182 1	602.222 4 583.177 5	-1.3 -7.8	445.152 0, 301.105 2, 267.086 8, 249.076 3, 179.071 2, 151.076 4, 105.035 9 583.185 3, 553.164 1, 431.144 9, 121.030 9	苯甲酰芍药苷	BS
70	C₅₄H₉₂O₂₃	38.18	[M+Na]⁺	1131.592 2	1131.589 9	-2.0	1 131.588 4, 365.104 9	人参皂苷Rb₁^*	RS
71	C₁₂H₁₂O₂	39.09	[M+H]⁺	189.091 0	189.091 0	0.1	189.094 0, 171.079 2, 161.057 4, 143.050 8, 105.035 9, 77.041 4	丁烯基苯酞	DG
72	C₄₁H₇₀O₁₂	39.11	[M+Na]⁺	777.476 0	777.476 1	0.2	777.474 8, 335.095 4	人参皂苷CY	RS
73	C₄₂H₇₂O₁₃	39.87	[M+Na]⁺	807.486 5	807.485 1	-1.7	807.487 2, 349.114 6	人参皂苷F₂	RS
74	C₁₆H₁₄O₄	39.99 40.01	[M+H]⁺ [M-H]^-	271.096 5 269.081 9	271.096 4 269.080 4	0.5 -5.9	271.094 7, 229.086 9, 177.054 5, 134.036 7, 121.029 4, 107.050 7, 93.035 7 269.084 1, 237.056 1, 175.041 9, 161.025 9, 133.031 1, 120.0226, 92.028 3	刺甘草查尔酮	GC
75	C₄₈H₇₆O₁₉	40.26	[M+Na]⁺	979.487 3	979.485 5	-1.9	979.485 3, 641.400 7	人参皂苷Ro	RS
76	C₉H₈O	40.94	[M+H]⁺	133.064 8	133.064 5	-2.1	133.068 4, 103.056 2, 77.042 2	桂皮醛^*	RG
77	C₁₅H₁₆O₃	41.02	[M+H]⁺	245.117 2	245.117 0	-0.8	245.117 3, 229.086 2, 225.089 7, 201.090 0, 169.063 4	Kwangsiensis A	EZ
78	C₁₆H₁₂O₅	41.23	[M-H]^-	283.061 2	283.059 5	-5.9	283.062 8, 268.038 9, 224.048 2, 135.010 3	樱黄素	GC
79	C₃₀H₄₆O₅	41.97	[M+H]⁺	487.341 8	487.340 7	-2.3	487.341 7, 317.210 4	24-羟基甘草次酸	GC
80	C₃₀H₄₄O₄	41.97	[M+H]⁺	491.313 2	491.311 8	-2.3	469.330 9, 451.321 1, 439.319 8, 235.168 8	光甘草内酯	GC
81	C₁₆H₁₂O₆	42.78 42.81	[M+H]⁺ [M-H]^-	301.070 7 299.056 1	301.070 8 299.053 4	0.5 -9.1	301.072 4, 286.046 5, 285.038 9, 258.052 7, 229.048 0, 136.016 2, 121.029 9 299.056 8, 284.034 5, 255.031 2, 227.036 7	金圣草(黄) 素	GC
82	C₅₅H₉₂O₂₃	43.01	[M+Na]⁺	1143.592 2	1143.590 8	-1.2	1 143.589 6, 831.487 5	人参皂苷Rs₂	RS
83	C₉H₁₀O₃	43.90	[M+H]⁺	167.070 3	167.070 1	-0.9	167.071 5, 149.061 3, 125.061 2, 121.066 8	丹皮酚^*	MDP
84	C₃₀H₄₆O₄	44.21	[M+H]⁺	471.346 9	471.346 5	-0.9	471.346 2, 317.211 6, 235.169 1	甘草次酸	GC
85	C₄₂H₆₂O₁₆	44.23	[M+H]⁺	823.411 1	823.410 1	-1.2	823.406 5, 647.377 6, 471.347 6, 453.335 4, 435.324 2, 407.329 5	甘草酸^*	GC
86	C₁₀H₁₀O₂	44.76	[M+H]⁺	163.075 4	163.075 2	-1.2	163.077 4, 135.079 8, 131.048 1, 107.051 0, 103.054 5, 77.042 0	邻甲氧基肉桂醛	RG
87	C₉H₁₀O	44.76	[M+H]⁺	135.073 2	135.080 3	-0.9	103.055 1, 77.042 3	肉桂醇	RG
88	C₁₂H₁₄O₃	44.87	[M-H]^-	205.087 0	205.085 7	-6.4	161.097 4, 119.947 3, 83.052 1	4-羟基-3-丁基苯酞	DG
89	C₁₆H₁₂O₄	45.03 45.04	[M+H]⁺ [M-H]^-	269.080 8 267.066 3	269.080 4 267.064 5	-1.6 -6.8	269.080 8, 254.056 2, 253.049 0, 237.054 0, 226.062 1 267.066 9, 252.043 8, 223.040 4, 135.009 1	刺芒柄花素	GC
90	C₁₂H₁₄O₃	47.03 47.06	[M+H]⁺ [M-H]^-	207.101 6 205.087 0	207.100 7 205.086 2	-4.2 -4.2	191.004 2, 151.038 7, 147.044 3, 105.035 2, 77.041 9 205.088 8, 161.098 8, 106.044 5	洋川芎内酯F	DG
91	C₁₆H₂₂O₄	48.69	[M+H]⁺	279.159 1	279.158 8	-1.0	279.160 7, 149.023 6, 121.030 1, 105.033 7, 79.054 1	邻苯二甲酸二丁酯	CX
92	C₁₆H₁₄O₄	49.36	[M+H]⁺	271.096 5	271.095 6	0.5	271.099 5, 161.060 8, 109.066 6	美迪紫檀素	GC
93	C₁₂H₁₂O₃	49.64	[M-H]^-	203.071 4	203.070 7	-3.4	203.073 2, 173.025 6, 160.017 9, 145.031 1	3-丁烯基-7-羟基苯酞	CX
94	C₂₀H₂₂O₆	51.91	[M-H]^-	357.134 4	357.130 8	-8.9	357.135 5, 232.075 0, 149.025 7, 109.031 4	松脂素	GC
95	C₂₀H₂₀O₆	52.58	[M-H]^-	355.118 7	355.115 5	-9.1	355.120 6, 229.088 4, 174.033 4, 83.015 7	阿魏酸松柏酯	DG
96	C₁₅H₂₀O	52.67	[M+H]⁺	217.158 7	217.158 1	-2.5	176.116 2, 162.099 3	莪术烯	EZ
97	C₁₅H₂₂O₂	52.69	[M+Na]⁺	257.151 2	257.151 0	-0.8	257.150 9	羟基雅槛蓝酮	EZ
98	C₂₀H₁₈O₇	53.59	[M-H]^-	369.098 0	369.094 7	-8.8	369.098 9, 300.029 8, 151.005 3, 107.017 7	乌拉尔醇	GC
99	C₁₂H₁₆O₂	53.61	[M+H]⁺	193.122 3	193.121 8	-2.9	193.121 6, 137.060 3, 77.042 3	洋川芎内酯A	CX
100	C₁₇H₁₄O₆	53.76	[M-H]^-	313.071 8	313.069 5	-7.2	313.073 0, 298.049 1, 283.026 2, 255.031 1	华良姜素	GC
101	C₂₀H₁₈O₆	54.23	[M+H]⁺	355.117 6	355.118 3	1.9	355.118 2, 337.106 6, 299.056 0, 243.064 2, 179.034 0, 151.039 8	甘草黄酮醇	GC
102	C₂₀H₂₀O₅	54.88 54.91	[M+H]⁺ [M-H]^-	341.138 4 339.122 2	341.137 6 339.120 8	-2.1 -8.8	341.136 0, 285.075 6, 272.068 9, 257.082 3 325.104 3, 282.050 0, 270.050 6, 254.054 1	鳞叶甘草素B	GC
103	C₁₅H₁₄O	55.06	[M+H]⁺	211.111 7	211.111 4	-1.5	211.110 6, 196.089 5, 195.079 5, 181.066 2, 152.062 2, 151.055 4	乌药薁	EZ
104	C₇H₆O₃	55.07	[M+H]⁺	139.039 0	139.038 6	-2.7	139.039 1, 121.029 1, 93.035 9	水杨酸	BS
105	C₂₀H₁₈O₆	55.69	[M+H]⁺	355.117 6	355.117 4	-0.6	355.118 2, 337.106 6, 229.085 9, 201.091 5, 189.091 0, 179.034 0, 153.018 7	甘草异黄烷酮	GC
106	C₂₁H₂₂O₄	56.08	[M+H]⁺	339.159 1	339.158 4	-2.0	339.159 6, 297.150 7, 271.096 9, 121.029 7, 93.036 2	甘草查尔酮A	GC
107	C₂₀H₁₈O₅	57.13	[M+H]⁺	339.122 7	339.122 5	-0.6	339.122 8, 283.060 5	黄羽扇豆魏特酮	GC
108	C₁₂H₁₄O₂	57.16	[M+H]⁺	191.106 7	191.105 2	-7.6	191.106 9, 161.060 5, 149.060 8, 79.057 6	正丁基苯酞	DG
109	C₂₀H₁₈O₅	57.34 57.36	[M+H]⁺ [M-H]^-	339.122 7 337.108 2	339.122 1 337.105 5	-1.9 -7.8	355.121 0, 299.060 8, 287.055 3, 271.060 9, 229.086 5, 69.074 6 337.110 1, 281.047 8, 145.030 5	鳞叶甘草素A	GC
110	C₁₅H₂₂O	58.13	[M+H]⁺	219.174 3	219.173 9	-2.0	176.119 3, 149.100 1, 133.067 3, 121.102 5, 119.087 1, 109.102 0, 105.070 4, 97.068 1	莪术酮	EZ
111	C₁₅H₂₄O₂	58.18	[M+H]⁺	237.184 9	237.184 2	-3.1	237.106 9, 107.087 5, 93.072 7	莪术二酮	EZ
112	C₁₂H₁₈O₂	58.57	[M+H]⁺	195.138 0	195.137 7	-1.4	81.073 4, 79.057 8	新蛇床内酯	CX
113	C₂₀H₂₀O₄	58.63	[M+H]⁺	325.143 4	325.143 1	-1.1	325.141 2, 149.060 2, 147.040 1, 121.192 8, 103.053 4, 77.041 8	光甘草宁	GC
114	C₁₂H₁₄O₂	59.21	[M+H]⁺	191.106 7	191.106 3	-1.9	191.106 6, 173.096 1, 145.100 9	Z-藁本内酯^*	CX, DG
115	C₂₀H₁₈O₆	59.46	[M+H]⁺	355.117 6	355.117 1	-1.5	355.120 3, 299.055 6, 121.030 3	甘草异黄酮A	GC
116	C₁₅H₂₀O	60.04	[M+H]⁺	217.158 7	217.158 5	-0.9	217.158 9, 202.137 5, 189.127 4, 175.112 9, 161.096 0, 149.096 7, 135.082 1, 119.086 7, 109.102 1	呋喃二烯	EZ
117	C₉H₈O₂	60.07	[M+H]⁺	149.059 7	149.059 2	-3.6	149.062 3, 121.032 5	肉桂酸	RG
118	C₁₅H₁₈O₂	60.10	[M+H]⁺	231.138 0	231.137 6	-1.8	231.138 1, 175.077 1, 173.096 2, 163.073 5, 161.060 0, 147.080 9, 135.081 4, 119.086 5, 105.071 2, 83.087 7	表莪术烯酮	EZ
119	C₂₀H₁₆O₅	60.42 60.43	[M+H]⁺ [M-H]^-	337.107 1 335.092 5	337.106 8 335.089 4	-0.9 -9.3	337.106 4, 319.096 2, 295.058 0 335.094 0, 320.069 0, 319.063 5, 317.082 1, 305.045 4	光甘草酮	GC
120	C₂₅H₂₆O₆	61.19	[M+H]⁺	423.180 2	423.178 9	-3.2	423.180 6, 367.117 4, 311.057 4, 299.054 0	粗毛甘草素A	GC
121	C₂₅H₃₂O₅	62.38	[M+H]⁺	413.232 3	413.231 7	-1.4	191.106 4, 149.060 2, 135.043 6	Wallichilide	CX
122	C₂₄H₂₈O₄	62.62	[M+H]⁺	381.206 0	381.205 8	-0.8	191.106 8, 149.060 0, 135.044 6	欧当归内酯A	DG
注: CX、DG、NX、EZ、GC、RG、RS、BS、MDP为川芎、当归、牛膝、莪术、甘草、肉桂、人参、白芍和牡丹皮; ^*表示化合物10、26、37、42、46、54、68、70、76、83、85、114在图谱中均有较高的峰, 且与对照品在图谱的相应位置出峰。

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表 3 10批温经汤基准样品HPLC-UV指纹图谱相似度

Table 3. Similarity of fingerprint of 10 batches of WJT substance benchmarks

批号	S1	S2	S3	S4	S5	S6	S7	S8	S9	S10	对照
S1	1.000	0.979	0.994	0.994	0.984	0.963	0.987	0.972	0.991	0.966	0.989
S2	0.979	1.000	0.991	0.990	0.995	0.995	0.990	0.996	0.990	0.993	0.997
S3	0.994	0.991	1.000	0.998	0.992	0.980	0.994	0.987	0.996	0.983	0.997
S4	0.994	0.990	0.998	1.000	0.994	0.980	0.993	0.986	0.996	0.983	0.997
S5	0.984	0.995	0.992	0.994	1.000	0.990	0.988	0.992	0.990	0.989	0.996
S6	0.963	0.995	0.980	0.980	0.990	1.000	0.987	0.994	0.984	0.992	0.991
S7	0.987	0.990	0.994	0.993	0.988	0.987	1.000	0.989	0.999	0.986	0.997
S8	0.972	0.996	0.987	0.986	0.992	0.994	0.989	1.000	0.988	0.999	0.995
S9	0.991	0.990	0.996	0.996	0.990	0.984	0.999	0.988	1.000	0.986	0.998
S10	0.966	0.993	0.983	0.983	0.989	0.992	0.986	0.999	0.986	1.000	0.992
对照	0.989	0.997	0.997	0.997	0.996	0.991	0.997	0.995	0.998	0.992	1.000

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表 4 10批温经汤基准样品共有峰相对保留时间

Table 4. Relative shift of retention time of characteristic peaks in transfer among 10 batches of WJT

峰号	S1	S2	S3	S4	S5	S6	S7	S8	S9	S10	RSD/%
1	0.387	0.387	0.387	0.386	0.390	0.388	0.388	0.387	0.387	0.386	0.28
2	0.655	0.655	0.655	0.655	0.658	0.655	0.655	0.655	0.654	0.655	0.15
3	0.850	0.850	0.849	0.848	0.850	0.848	0.848	0.849	0.849	0.849	0.07
4	0.927	0.927	0.927	0.927	0.927	0.927	0.927	0.927	0.927	0.926	0.04
5	0.940	0.940	0.942	0.941	0.940	0.939	0.941	0.940	0.941	0.939	0.08
6	0.962	0.962	0.963	0.962	0.962	0.962	0.962	0.962	0.962	0.962	0.02
7	1.000	1.000	1.000	1.000	1.000	1.000	1.000	1.000	1.000	1.000	0.00
8	1.149	1.150	1.149	1.150	1.148	1.151	1.150	1.151	1.150	1.151	0.08
9	1.198	1.197	1.198	1.198	1.195	1.198	1.199	1.198	1.198	1.198	0.08
10	1.381	1.381	1.382	1.384	1.376	1.382	1.382	1.382	1.381	1.383	0.15
11	1.465	1.464	1.465	1.467	1.459	1.465	1.465	1.465	1.465	1.467	0.16
12	1.478	1.479	1.479	1.481	1.472	1.478	1.479	1.479	1.478	1.481	0.16
13	1.539	1.538	1.539	1.539	1.533	1.538	1.538	1.539	1.538	1.540	0.12
14	1.591	1.591	1.592	1.595	1.584	1.591	1.590	1.591	1.591	1.593	0.17
15	1.649	1.648	1.648	1.649	1.642	1.648	1.648	1.649	1.648	1.650	0.13
16	1.675	1.675	1.675	1.679	1.667	1.675	1.674	1.675	1.674	1.676	0.17
17	1.763	1.763	1.763	1.767	1.754	1.763	1.762	1.763	1.762	1.764	0.18
18	1.981	1.981	1.981	1.981	1.972	1.980	1.980	1.980	1.980	1.982	0.15
19	2.226	2.225	2.225	2.224	2.213	2.224	2.223	2.223	2.224	2.226	0.17

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经典名方温经汤基准样品HPLC-Q-TOF/MS分析与指纹图谱研究

doi: 10.14148/j.issn.1672-0482.2023.0452

作者简介: 汤志锋, 男, 硕士研究生, E-mail: 20200839@njucm.edu.cn

通讯作者: 黄仕文, 男, 副教授, 主要从事中药新剂型新技术及其产品开发研究, E-mail: hshw_66@163.com 程建明, 男, 研究员, 主要从事中药新剂型新技术及其产品开发研究, E-mail: cjm@njucm.edu.cn

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Study on HPLC-Q-TOF/MS Analysis and Fingerprint of Classic Prescription Wenjing Decoction Substance Benchmarks

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作者简介:
汤志锋, 男, 硕士研究生, E-mail: 20200839@njucm.edu.cn

通讯作者:
黄仕文, 男, 副教授, 主要从事中药新剂型新技术及其产品开发研究, E-mail: hshw_66@163.com

程建明, 男, 研究员, 主要从事中药新剂型新技术及其产品开发研究, E-mail: cjm@njucm.edu.cn