基于UHPLC-Q-TOF/MS的地榆化学成分分析及大鼠体内代谢研究

裴玉琼; 徐坠成; 王艳天; 顾欣; 盛先杰; 徐艺; 缪志伟

doi:10.14148/j.issn.1672-0482.2021.0897

基于UHPLC-Q-TOF/MS的地榆化学成分分析及大鼠体内代谢研究

doi: 10.14148/j.issn.1672-0482.2021.0897

裴玉琼^1,,
徐坠成¹,
王艳天²,
顾欣²,
盛先杰¹,
徐艺^2, ,,
缪志伟^3, ,

1.
南京中医药大学药学院, 江苏南京 210023
2.
南京中医药大学附属医院, 江苏南京 210029
3.
南京中医药大学附属张家港医院, 江苏张家港 215600

基金项目:

江苏省中医药科技发展计划 RC201903

江苏省“333高层次人才培养工程”科研项目 LGY2018060

苏州市科技发展计划 SYS2020056

南京中医药大学自然科学基金 XZR2020059

详细信息

作者简介:
裴玉琼, 女, 实验师, E-mail: 832002@njucm.edu.cn

通讯作者:
缪志伟, 男, 主治中医师, 主要从事脾胃病的方药研究, E-mail: zjgzy011@njucm.edu.cn

徐艺, 女, 主任中医师, 主要从事脾胃病的中医药防治研究, E-mail: fsyy00638@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: 2021-07-30
- 网络出版日期: 2021-12-21
- 刊出日期: 2021-11-10
- 发布日期: 2021-11-15

Identification of Chemical Composition of Sanguisorba officinalis L. and Its Major Metabolites in Rats by UHPLC-Q-TOF/MS

1.
School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210023, China
2.
The Affiliated Hospital of Nanjing University of Chinese Medicine, Nanjing, 210029, China
3.
Zhangjiagang TCM Hospital Affiliated to Nanjing University of Chinese Medicine, Zhangjiagang, 215600, China

摘要

摘要: 目的采用超高效液相色谱和-四级杆串联飞行时间质谱(UHPLC-Q-TOF/MS)法分析地榆水提物在大鼠血清、尿液及粪便中的原型成分及代谢产物, 探讨地榆中活性成分在大鼠体内的代谢途径。方法采用Thermo Acclaim^TM RSLC 120 C₁₈色谱柱(3.0 mm×100 mm, 2.2 μm), 以0.1%甲酸水溶液(A)-乙腈(B)为流动相进行梯度洗脱, 流速0.4 mL·min^-1, 进样量3 μL, 柱温40 ℃。运用电喷雾离子源(ESI), 扫描范围m/z 50~1 500, 正、负离子模式采集数据。通过比较灌胃地榆水提物后大鼠血清、尿液和粪便样品和空白组样品的差异, 对原型成分及其代谢产物进行鉴定。结果灌胃给予地榆水提物后, 从大鼠血清、尿液及粪便中鉴定出69个外源性成分, 包括24个原型成分和45个代谢产物。其中24个原型成分包括16个酚类成分、7个三萜类成分及1个单萜烯醇苷。地榆水提物在大鼠体内的代谢途径主要包括还原、甲基化、脱水、氧化、硫酸化及葡萄糖醛酸结合等。结论所鉴定出的原型成分和代谢产物可为进一步解析地榆体内代谢过程, 阐明其药效物质基础提供实验依据。
- 地榆 /
- UHPLC-Q-TOF/MS /
- 原型成分 /
- 代谢产物
Abstract: OBJECTIVE To analyze the prototype components and metabolites of aqueous extract of Sanguisorba officinalis L. by UHPLC-Q-TOF/MS in feces, urine and plasma of rats and explore its metabolic pathways.METHODS Chromatographic separation was performed on the Thermo Acclaim^TM RSLC 120 C₁₈ column (3.0 mm×100 mm, 2.2 μm). The mobile phase was consisted of 0.1% formic acid in water (solvent A) and acetonitrile (solvent B). The sample injection volume was 3 μL and the flow rate was set to 0.4 mL·min^-1. The column temperature was maintained at 40 ℃. The detection was carried out over a mass range of m/z 50-1 500 and equipped with an electrospray ionization (ESI) source operating in positive mode and negative mode. Chemical composition on Sanguisorba officinalis L. and its major metabolites were identified by comparing the differences in feces, urine and plasma between adminstration samples and blank samples in rats.RESULTS After intragastric administration of the aqueous extract of Sanguisorba officinalis L., 69 exogenous components were identified from rat plasma, urine and feces, including 24 prototype components and 45 metabolites. 24 prototype components included 16 phenolics, 7 triterpenes, and a monoterpene glycoside. The metabolic pathways of the aqueous extract of Sanguisorba officinalis L. in rats mainly included reduction, methylation, dehydration, oxidation, sulfation, and glucuronidation.CONCLUSION The identified prototype drugs and the metabolites can supply a clear material basis for the further study of efficacy of Sanguisorba officinalis L..
- Sanguisorba officinalis L. /
- UHPLC-Q-TOF/MS /
- prototypes /
- metabolites

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图 1 地榆水提物和对照品在正、负离子模式下的基峰离子色谱

注: ^*表示化合物与对照品确认。

下载: 全尺寸图片幻灯片

图 2 地榆皂苷Ⅰ(A)、地榆皂苷Ⅱ(B)和地榆皂苷Ⅲ(C)的MS/MS

下载: 全尺寸图片幻灯片

图 3 鞣花酸化合物的代谢途径

下载: 全尺寸图片幻灯片

图 4 地榆皂苷Ⅰ的代谢途径

下载: 全尺寸图片幻灯片

表 1 地榆水提物化学成分鉴定

峰号	t_R/min	化合物	分子式	m/z[M-H/+HCOO]^-			碎片离子	m/z[M+H]⁺			碎片离子
峰号	t_R/min	化合物	分子式	理论值	实测值	δ	碎片离子	理论值	实测值	δ	碎片离子
C1	1.43	没食子酸糖苷 (Gallic acid glycoside)	C₁₃H₁₆O₁₀	331.067 1	331.067 0	-0.3	271.045 1, 211.023 9, 169.013 2，125.023 8	333.081 6	333.081 4	-0.7
C2	1.85	没食子酸^*(Gallic acid)	C₇H₆O₅	169.014 3	169.015 0	4.5	125.023 3	171.028 8	171.028 7	-0.8
C3	3.7	没食子儿茶素(Gallocatechin)	C₁₅H₁₄O₇	305.066 7	305.067 0	1.0	219.064 5，179.033 7, 137.023 5，125.023 8	307.081 2	307.081 5	0.7
C4	3.73	表没食子儿茶素 (Epigallocatechin)	C₁₅H₁₄O₇	305.066 7	305.067 0	1.0	247.023 4	307.081 2	307.081 5	0.7
C5	5.34	没食子酰基-甲基葡萄糖苷 (Methyl-6-O-galloyl-β-D- glucopyranoside)	C₁₄H₁₈O₁₀	345.082 7	345.082 8	0.2	313.054 1，169.013 2	347.097 3	347.097 4	0.4	315.071 1, 171.028 5
C6	5.57	表儿茶素-(4→8)-没食子儿茶素(Epicatechin- (4→8)-gallocatechin)	C₃₀H₂₆O₁₃	593.130 1	593.129 5	-0.9	441.081 8，423.072 6, 305.066 9，283.025 2, 255.029 9	595.144 6	595.144 0	-1.1	455.350 1, 437.338 8
C7	6.71	Sanguiin H4	C₂₇H₂₂O₁₈	633.073 3	633.072 8	-0.9	300.997 6	635.087 9	635.087 3	-0.9
C8	7.32	原花青素B3 (Procyanidin B3)	C₃₀H₂₆O₁₂	577.135 2	577.134 8	-0.7	425.086 8，407.076 2	579.149 7	579.148 8	-1.6	427.102 3, 409.091 9
C9	7.48	6-O-Galloylnorbergerin	C₂₀H₁₈O₁₃					467.082 0	467.081 7	-0.7	315.066 1
C10	7.53	二没食子酰葡萄糖苷 (Bisgalloyl glucoside)	C₂₀H₂₀O₁₄	483.078 0	483.077 3	-1.5	331.064 0，313.055 1, 271.044 6，211.023 4, 193.006 9，169.012 5	485.092 6	485.092 9	0.6
C11	7.63	原花青素C2(Procyanidin C2)	C₄₅H₃₈O₁₈	865.198 5	865.198 8	0.3	695.143 7，577.137 0, 407.075 2	867.213 1	867.212 1	-1.1
C12	7.86	儿茶素^*(Catechin)	C₁₅H₁₄O₆	289.071 8	289.071 9	0.4	441.082 9，245.079 9, 203.070 2	291.086 3	291.086 3	0	165.054 3, 147.044 2, 139.039 0, 123.044 6
C13	7.89	表儿茶素(Epicatechin)	C₁₅H₁₄O₆	289.071 8	289.071 9	0.4	245.080 6，203.070 3, 161.059 6	291.086 3	291.086 3	0
C14	8.66	三没食子酰葡萄糖苷 (Trigalloyl glucoside)	C₂₇H₂₄O₁₈	635.089 0	635.088 2	-1.3	483.076 3，465.066 3, 313.053 9，221.020 2	637.103 5	637.102 3	-1.9
C15	8.95	短叶苏木酚酸 (Brevifolincarboxylic acid)	C₁₃H₈O₈	291.014 6	291.014 8	0.6	247.060 0，203.070 3	293.029 2	293.029 3	0.3	273.073 3
C16	9.09	二没食子酰基-D-甲基吡喃葡萄糖苷(Methyl 4，6-di-O- galloyl-β-D-glucopyranoside)	C₂₁H₂₂O₁₄	497.093 7	497.092 8	-1.8	497.093 5，345.082 3	499.108 2	499.107 8	-1
C17	9.31	2, 6-乙酰氧基-5, 7-二羟基-8-甲氧基色原酮(2，6- Acetoxy-5，7-dihydroxy-8- methoxychromone)	C₁₄H₁₂O₉	323.040 9	323.040 6	-0.8		325.055 4	325.055 2	-0.6	293.029 2
C18	9.32	没食子酰鞣花酸 (Galloyl ellagic acid)	C₂₁H₁₀O₁₃	469.004 9	469.004 9	0	316.994 0，300.998 7	471.019 4	471.019 1	-0.8
C19	9.35	地榆酸双内酯 (Dilin dilactone)	C₂₁H₁₀O₁₃	469.004 9	469.004 9	0	314.978 3，300.998 7, 286.983 7，230.992 4	471.019 4	471.019 1	-0.8
C20	9.72	甲氧基没食子酸甲酯-5-O-硫酸酯(Methyl methoxygallate-5-O-sulfate)	C₉H₁₀SO₈	277.002 4	277.002 4	0	197.043 9，182.020 2, 166.996 7，139.002 7, 123.007 4	279.016 9	279.016 7	-0.9	199.059 7
C21	10	3-O-没食子酰基-原花青素B3(3-O-Galloylprocyanidin B3)	C₃₇H₃₀O₁₆	729.146 1	729.146 1	-0.1	577.136 1，407.076 8	731.160 7	731.159 1	-2.1
C22	10.47	非瑟酮醇-(4β-8)-儿茶素(Fisetinol-(4β-8)-catechin)	C₃₀H₂₆O₁₁	561.140 2	561.139 5	-1.3	409.092 7，391.081 7, 289.070 7，245.080 5, 203.069 1	563.154 8	563.153 8	-1.8
C23	10.69	鞣花酸-4-吡喃阿拉伯糖苷(Ellagic acid-4-arabinopyranoside)	C₁₉H₁₄O₁₂	433.041 3	433.040 5	-1.8		435.055 8	435.056 1	0.6	303.013 1
C24	11.02	2, 3, 4, 6-O-四没食子酰基-β-D-葡萄糖苷(2，3，4，6-O-Tetragalloyl-β-D-glucoside)	C₃₄H₂₈O₂₂	787.100 0	787.100 0	0.1	635.089 3，617.077 1, 465.065 9，447.056 6, 313.055 1，295.045 1	789.114 5	789.113 5	-1.3
C25	11.31	鞣花酸^*(Ellagic acid)	C₁₄H₆O₈	300.999 0	300.998 8	-0.7	300.996 3，283.995 6, 229.012 6	303.013 5	303.013 3	-0.9
C26	11.58	三没食子酰基-β-D-甲基葡萄糖苷(Trigalloyl- β-D-Methyl glucoside)	C₂₈H₂₆O₁₈	649.104 6	649.104 1	-0.8	497.094 6，479.085 1, 345.082 1，327.070 6	651.119 2	651.118 2	-1.5
C27	11.63	儿茶素没食子酸酯 (Catechin gallate)	C₂₂H₁₈O₁₀	441.082 7	441.081 7	-2.4	441.082 9，289.071 0, 245.079 9，203.070 2	443.097 3	443.096 6	-1.5
C28	11.69	金丝桃苷(Hyperoside)	C₂₁H₂₀O₁₂	463.088 2	463.087 5	-1.6	463.088 7，301.034 6	465.102 8	465.102 2	-1.2
C29	11.9	五没食子酰葡萄糖苷 (Pentagalloyl glucoside)	C₄₁H₃₂O₂₆	939.110 9	939.110 6	-0.3	769.093 4, 617.081 0, 169.013 2
C30	12.63	2-甲基-3-乙酰氧基-苯并呋喃-5, 6-O-硫酸酯(2-Methyl-3-acetoxy-benzofuran-5，6-O-sulfate)	C₁₂H₁₂O₁₁S₂	394.974 8	394.970 5	-11	315.013 1，299.989 4	396.989 4	396.985 6	-9.5
C31	15.54	3, 4'-O-二甲基鞣花酸-4-O-β-D-木糖苷(3, 4'-O-Dimethylellagic acid-4-O-β-D-xyloside)	C₂₁H₁₈O₁₂	461.072 6	461.071 5	-2.3	329.029 5，314.006 3, 298.982 0，285.003 0	463.087 1	463.086 2	-2.1
C32	15.61	3, 4'-O-二甲基鞣花酸(3，4'-O-Dimethyl ellagic acid)	C₁₆H₁₀O₈	329.030 3	329.029 6	-2.1	314.004 0，298.980 2, 285.001 5，258.015 0	331.044 8	331.044 6	-0.8
C33	15.63	3, 4'-O-二甲基鞣花酸-4-O-硫酸酯(3，4'-O-Dimethylellagic acid-4-O-sulfate)	C₁₆H₁₀O₁₁S	408.987 1	408.985 8	-3.1	329.027 6，314.004 3, 298.980 0	411.001 7	411.001 3	-1.0	331.044 7, 316.020 3, 300.999 9
C34	15.98	槲皮素^*(Quercetin)	C₁₅H₁₀O₇	301.035 4	301.034 5	-3.0	301.030 9，273.037 7, 178.996 5，151.002 1, 121.029 2	303.049 9	303.049 7	-0.8
C35	16.47	香叶醇-1-O-呋喃阿拉伯糖基-(1→6)-β-D-吡喃葡萄糖苷(Geranyl-1-O-furanyl-arabinose-(1→6)-β-D-glucopyranoside)	C₂₁H₃₆O₁₀	447.223 6	447.222 1	-3.3	447.216 9，315.178 0, 251.075 3，221.061 3, 191.055 2，179.053 5	449.238 1	449.237 4	-1.6
C36	16.48	3, 3', 4'-O-三甲基鞣花酸-4-O-D-木糖苷(3，3'，4'-O-Trimethylellagic acid-4-O-D-xyloside)	C₂₂H₂₀O₁₂	475.088 2	475.086 8	-2.9	343.053 9，328.026 7, 313.001 4	477.102 8	477.102 5	-0.6
C37	16.83	3, 3', 4'-O-三甲基鞣花酸-4-O-硫酸酯(3，3'，4'-O-Trimethylellagic acid-4-O-sulfate)	C₁₇H₁₂O₁₁S	423.002 8	423.001 5	-3.0	343.042 8，328.019 5, 312.996 3	425.017 3	425.016 9	-1.0
C38	18.1	山柰酚^*(Kaempferol)	C₁₅H₁₀O₆	285.040 5	285.039 7	-2.7	285.038 5，239.037 0, 185.061 7，93.035 4	287.055 0	287.054 6	-1.4
C39	19.11	地榆皂苷Ⅰ^* (ZiyuglycosideⅠ)	C₄₁H₆₆O₁₃	811.447 5	811.449 9	3.0	765.444 5，603.389 0, 585.380 2
C40	19.14	3-氧代-12-烯-28-乌苏酸(3-Oxo-12-ene-28-ursic acid)	C₃₀H₄₆O₃	453.337 4	453.335 3	-4.6		455.352 0	455.350 9	-2.5	437.340 8, 409.345 2, 391.335 5
C41	19.96	3, 3', 4'-O-三甲基鞣花酸(3，3'，4'-O-Trimethylellagic acid)	C₁₇H₁₂O₈	343.045 9	343.045 2	-2.2	328.020 2，312.996 6	345.060 5	345.059 8	-1.9
C42	22.22	坡模醇酸(Pomolic acid)	C₃₀H₄₈O₄	471.348 0	471.345 7	-4.8		473.362 5	473.360 9	-3.4	455.350 1, 437.338 8
C43	22.23	地榆皂苷Ⅲ (Ziyuglycoside Ⅲ)	C₃₆H₅₈O₉	679.405 2	679.404 6	-1.3	633.399 2, 471.355 1， 453.335 0
C44	23.11	地榆皂苷Ⅱ^* (Ziyuglycoside Ⅱ)	C₃₅H₅₆O₈	603.389 5	603.390 8	2.2	585.379 8	605.404 8	605.403 0	-3.0
C45	23.72	3, 11-二酮-19α-羟基-乌苏-12-烯-28-酸(3，11-Dioxo-19α-hydroxy-urs-12-en-28-oic acid)	C₃₀H₄₄O₅	483.311 6	483.310 3	-2.7	421.310 7	485.326 2	485.324 5	-3.5	439.318 4
注: ^*表示化合物与对照品确认。

下载: 导出CSV

表 2 血浆、尿液和粪便中原型成分和代谢产物的鉴定

峰号	t_R/min	鉴定结果	离子模式	分子式	理论值	实测值	δ	碎片离子	来源
C2	1.84	没食子酸, 原型(Gallic acid，parent)	[M-H]^-	C₇H₆O₅	169.014 3	169.015 0	4.5	169.012 6，125.025 1	粪便
C2-1	9.48	1，3-二甲氧基没食子酸(1，3-Dimethoxygallic acid)	[M-H]^-	C₉H₁₀O₅	197.045 6	197.046 3	3.6	123.008 3	粪便
C2-2	7.88	3-甲氧基没食子酸(3-Methoxygallic acid)	[M-H]^-	C₈H₈O₅	183.029 9	183.030 2	1.5	123.077 7	粪便
C2-3	1.84	焦没食子酸(Pyrogallic acid)	[M-H]^-	C₆H₆O₃	125.024 4	125.025 4	8.1	081.035 8	粪便
C2-4	7.87	C2失去2个氧原子(Two oxygen atoms loss of C2)	[M-H]^-	C₇H₆O₃	137.024 4	137.025 3	6.8	93.034 5，65.006 0	粪便
C2-5	9.67	C2甲基化和葡萄糖醛酸化(Methylation and glucuronidation of C2)	[M-H]^-	C₁₅H₁₈O₁₁	373.077 6	373.077 4	-0.7	197.044 9	粪便, 血浆
C2-6	10.21	C2甲基化和硫酸化(Methylation and sulfated of C2)	[M-H]^-	C₉H₁₀O₈S	277.002 4	277.002 5	0.6	166.997 7	粪便, 血浆
C2-7	15.15	C2结合甘氨酸(Glycine conjugated of C2)	[M-H]^-	C₉H₉NO₆	226.035 7	226.028 0	-34	182.043 6	粪便, 血浆
C3	13.33	儿茶素, 原型(Gallocatechin，parent)	[M-H]^-	C₁₅H₁₄O₇	305.066 7	305.063 8	-9.4	305.065 3，125.036 5	粪便
C3-1	14.86	C3甲基化(Methylation of C3)	[M-H]^-	C₁₆H₁₆O₇	319.089 8	319.082 5	0.6	213.068 9，187.055 5	粪便, 尿液
C3-2	7.01	C3氧化(Oxidation of C3)	[M-H]^-	C₁₅H₁₄O₈	321.067 1	321.058 6	-9.5	215.071 3，191.070 9, 147.081 5	粪便
C4-1	12.31	C4甲基化(Methylation of C4)	[M-H]^-	C₁₆H₁₆O₇	319.089 8	319.082 5	0.6	191.070 9，131.049 5	粪便, 尿液
C4-2	6.03	C4氧化(Oxidation of C4)	[M-H]^-	C₁₅H₁₄O₈	321.067 1	321.059 8	-5.6	303.149 6，197.047 0, 119.052 0	粪便
C7	14.73	Sanguiin H4, 原型(Sanguiin H4，parent)	[M-H]^-	C₂₇H₂₂O₁₈	633.073 3	633.067 3	-9.6	465.068 2	粪便
C8	7.37	原花青素B3, 原型(Procyanidin B3，parent)	[M-H]^-	C₃₀H₂₆O₁₂	577.135 2	577.134 5	-1.2	577.135 7，451.100 4, 425.088 8，407.076 4, 289.071 7，245.082 3	粪便
C8-1	11.71	C8甲基化(Methylation of C8)	[M-H]^-	C₃₁H₂₈O₁₂	591.158 9	591.151 6	1.4	381.061 5，230.020 4	粪便
C8-2	6.99	C8氧化(Oxidation of C8)	[M-H]^-	C₃₀H₂₆O₁₃	593.136 6	593.129 3	-1.3	454.135 6，397.094 0, 137.022 1	粪便
C11	7.64	原花青素C2, 原型(Procyanidin C2，parent)	[M-H]^-	C₄₅H₃₈O₁₈	865.198 5	865.198 2	-0.3	695.095 0，577.132 3, 451.097 4，407.081 4	粪便
C11-1	3.67	C11氧化(Oxidation of C11)	[M-H]^-	C₄₅H₃₈O₁₉	881.201 9	881.194 6	1.3	881.188 9	粪便
C12	8.78	儿茶素, 原型(Catechin，parent)	[M-H]^-	C₁₅H₁₄O₆	289.071 8	289.072 0	0.9	289.181 2，137.024 0	粪便
C12-1	11.64	C12甲基化(Methylation of C12)	[M-H]^-	C₁₆H₁₆O₆	303.094 5	303.087 7	1	191.069 8，153.019 5	粪便
C12-2	11.01	C12氧化(Oxidation of C12)	[M-H]^-	C₁₅H₁₄O₇	305.074 6	305.066 1	-8.5	223.098 8，165.065 2, 125.019 7	粪便
C13	8.76	表儿茶素, 原型(Epicatechin，parent)	[M-H]^-	C₁₅H₁₄O₆	289.071 8	289.072 0	0.9	289.072 5，245.046 7, 203.069 7	粪便
C13-1	16.54	C13甲基化(Methylation of C13)	[M-H]^-	C₁₆H₁₆O₆	303.094 5	303.087 3	-0.5	285.077 3，191.069 8, 153.019 5，69.001 0	粪便
C13-2	3.75	C13氧化(Oxidation of C13)	[M-H]^-	C₁₅H₁₄O₇	305.074 6	305.067 4	2.2	167.038 6，139.037 8	粪便
C15	8.37	短叶叶酸, 原型(Brevifolincarboxylic acid，parent)	[M-H]^-	C₁₃H₈O₈	291.014 6	291.014 8	0.5	247.023 5，219.028 0, 191.033 4	粪便
C17	10.73	2，6-乙酰氧基-5，7-二羟基-8-甲氧基色酮, 原型(2，6-Acetoxy-5，7-dihydroxy-8-methoxychromone，parent)	[M-H]^-	C₁₄H₁₂O₉	323.040 9	323.040 7	-0.4	232.040 9，219.028 4	粪便
C20	10.21	甲氧基没食子酸甲酯-5-O-硫酸盐, 原型(Methyl methoxygallate-5-O-sulfate，parent)	[M-H]^-	C₉H₁₀SO₈	277.002 4	277.002 5	0.6	197.045 2，182.021 9, 166.997 7	粪便, 血浆
C21	10	3-O-没食子酰原花青素B3, 原型(3-O-Galloyl-procyanidin B3，parent)	[M-H]^-	C₃₇H₃₀O₁₆	729.146 1	729.146 2	0.1	729.150 3，577.137 8, 559.120 7，425.089 0, 407.077 7，289.071 6, 269.045 1	粪便
C22	10.48	非瑟酮醇-(4β-8)-儿茶素，原型(Fisetinol-(4β-8)-catechin，parent)	[M-H]^-	C₃₀H₂₆O₁₁	561.140 2	561.139 7	-0.9	561.139 8，289.071 4	粪便
C25-1	15.17	尿石素A(Urolithin A)	[M-H]^-	C₁₃H₈O₄	227.035 0	227.035 5	2.5	227.032 2，198.030 5	粪便
C25-2	12.31	C25-1甲基化和硫酸化(Methylation and sulfated of C25-1)	[M-H]^-	C₁₃H₈O₇S	306.991 8	306.991 7	-0.3	227.034 5，198.032 2, 183.045 2	粪便, 血浆, 尿液
C25-3	20.31	C25-1甲基化(Methylation of C25-1)	[M-H]^-	C₁₄H₁₀O₄	241.050 6	241.052 0	5.5	198.027 0, 154.042 9	血浆
C25-4	13.12	C25-1葡萄糖醛酸化(Glucuronidation of C25-1)	[M-H]^-	C₁₉H₁₆O₁₀	403.067 1	403.067 0	-0.3	227.119 5	粪便, 血浆, 尿液
C25-5	12.76	尿石素C(Urolithin C)	[M-H]^-	C₁₃H₈O₅	243.029 9	243.030 4	2.2	215.033 7	粪便
C25-6	13.15	C25-5氧化(Oxidation of C25-5)	[M-H]^-	C₁₃H₆O₅	241.014 3	241.014 6	1.5	213.019 2，198.033 2, 185.024 5，169.027 9, 157.028 9，129.034 5	粪便
C25-7	12.09	尿石素D(Urolithin D)	[M-H]^-	C₁₃H₈O₆	259.024 8	259.025 6	3.2	241.013 5, 213.018 4	粪便, 尿液
C25-8	10.25	C25-7还原(Reduction of C25-7)	[M-H]^-	C₁₃H₁₀O₆	261.040 5	261.040 7	1	246.017 2，217.013 8, 189.019 1	粪便, 尿液
C25-9	10.12	尿石素M5(Urolithin M5)	[M-H]^-	C₁₃H₈O₇	275.019 7	275.020 1	1.4	257.009 2，229.014 0, 203.034 1，173.024 5, 145.029 5	粪便, 尿液
C25-10	13.78	C25甲基化(Methylation of C25)	[M-H]^-	C₁₅H₈O₈	315.021 8	315.014 5	-0.3	300.994 4, 245.002 7	粪便, 血浆
C27	12.65	儿茶素没食子酸, 原型(Catechin gallate，parent)	[M-H]^-	C₂₂H₁₈O₁₀	441.082 7	441.082 0	-1.6	289.187 1	粪便
C27-1	11.82	C27还原(Hydrogenation of C27)	[M-H]^-	C₂₂H₂₀O₁₀	443.104 4	443.097 1	-2.9	381.141 9，275.091 3, 123.009 8	粪便，血浆
C27-2	9.77	C27甲基化(Methylation of C27)	[M-H]^-	C₂₃H₂₀O₁₀	455.108 2	455.101 0	5.7	373.207 5，178.027 5, 80.996 1	粪便, 尿液
C27-3	2.56	C27氧化(Oxidation of C27)	[M-H]^-	C₂₂H₁₈O₁₁	457.086 0	457.078 8	2.4	287.032 8，275.054 5, 257.047 2	粪便, 血浆
C28-1	12.17	C28甲基化(Methylation of C28)	[M-H]^-	C₂₂H₂₂O₁₂	477.111 0	477.103 7	-0.2	395.151 3，269.045 9	粪便, 尿液
C28-2	6.37	C28还原(Hydrogenation of C28)	[M-H]^-	C₂₁H₂₂O₁₂	465.110 3	465.103 0	-1.9	357.066 2，289.068 7, 151.040 5	粪便
C31	15.54	3, 4'-O-二甲基鞣花酸-4-O-β-D木糖苷, 原型(3, 4'-O-Dimethylellagic acid-4-O-β-D-xyloside，parent)	[M-H]^-	C₂₁H₁₈O₁₂	461.072 6	461.070 6	-4.2	329.032 6	粪便, 血浆
C33	16.01	3, 4'-O-二甲基鞣花酸-4-O-硫酸酯, 原型(3，4'-O-Dimethylellagic acid-4-O-sulfate，parent)	[M-H]^-	C₁₆H₁₀O₁₁S	408.987 1	408.986 2	-2.2	329.032 6，314.006 7, 298.984 7	粪便, 血浆
C34-1	10.53	C34甲基化(Methylation of C34)	[M-H]^-	C₁₆H₁₂O₇	315.060 9	315.051 4	1.3	315.045 0，271.168 7, 183.105 3	粪便, 尿液
C34-2	16.91	C34还原(Hydrogenation of C34)	[M-H]^-	C₁₅H₁₂O₇	303.061 1	303.053 8	9.1	223.096 1，123.081 2	血浆
C34-3	8.76	C34氧化(Oxidation of C34)	[M-H]^-	C₁₅H₁₀O₈	317.039 1	317.031 8	4.8	237.075 8，172.075 1, 80.965 1	血浆
C35	16.44	Geranyl-1-O-furanyl-arabinose(1→6)-β-D-glucopyranoside, 原型	[M-H]^-	C₂₁H₃₆O₁₀	471.219 6	471.220 1	1.1	471.217 2，335.091 3	血浆
C37	17.03	3, 3', 4'-O-三甲基鞣花酸-4-O-硫酸酯, 原型(3，3'，4'-O-Trimethylellagic acid-4-O-sulfate，parent)	[M-H]^-	C₁₇H₁₂O₁₁S	423.002 8	423.001 4	-3.2	343.044 7，328.021 5, 312.997 9	粪便, 血浆
C38-1	21.75	C38甲基化(Methylation of C38)	[M-H]^-	C₁₆H₁₂O₆	299.063 3	299.056 0	-0.5	256.035 6，183.044 1, 159.043 6	粪便
C38-2	13.95	C38还原(Hydrogenation of C38)	[M-H]^-	C₁₅H₁₂O₆	287.065 8	287.058 5	8.3	207.101 6，149.058 1, 80.966 3	血浆
C38-3	9.33	C38氧化(Oxidation of C38)	[M-H]^-	C₁₅H₁₀O₇	301.045 4	301.038 2	9.3	177.091 5，123.007 9, 79.958 8	血浆
C39	19.14	地榆皂苷Ⅰ, 原型(ZiyuglycosideⅠ, parent)	[M-H]^-	C₄₁H₆₆O₁₃	765.442 3	765.444 2	2.4	603.389 2	粪便, 血浆
C39-1	23.13	C39-Glu	[M-H]^-	C₃₅H₅₆O₈	603.390 2	603.388 2	-3.4	585.380 7	粪便
C39-2	24.46	C39-Glu-Ara	[M-H]^-	C₃₀H₄₈O₄	471.348 0	471.346 3	-3.6	453.335 6	粪便
C39-3	22.25	C39-Ara	[M+Cl]^-	C₃₆H₅₈O₉	669.376 4	669.375 8	-0.8	471.347 7，453.339 1	粪便
C39-4	24.88	C39-Glu-Ara-2H	[M-H]^-	C₃₀H₄₆O₄	469.332 3	469.330 2	-4.6	451.320 8，407.330 7	粪便
C39-5	22.4	C39-Glu-Ara-O	[M-H]^-	C₃₀H₄₈O₃	455.353 1	455.348 9	-9.1	437.336 0	尿液
C40	24.44	3-氧代-12-烯-28-乌苏酸, 原型(3-oxo-12-ene-28-ursic acid，parent)	[M+H]⁺	C₃₀H₄₆O₃	455.352 0	455.350 2	-3.8	437.348 9，409.329 3, 391.286 4	粪便, 血浆
C41	19.99	3, 3', 4'-O-三甲基鞣花酸, 原型(3，3'，4'-O-Trimethylellagic acid, parent)	[M-H]^-	C₁₇H₁₂O₈	343.045 9	343.045 5	-1.3	328.020 7，312.997 0	粪便, 血浆
C42	24.45	坡模醇酸, 原型(Pomolic acid，parent)	[M+H]⁺	C₃₀H₄₈O₄	473.362 5	473.360 6	-4	455.351 8，437.347 1	粪便, 血浆
C42-1	21.94	C42氧化(Oxidation of C42)	[M+H]⁺	C₃₀H₄₈O₅	489.348 1	489.355 4	-4.2	453.333 6，281.171 0, 191.177 6，159.116 5	粪便
C43	22.25	地榆皂苷Ⅲ, 原型(Ziyuglycoside Ⅲ，parent)	[M-H]^-	C₃₆H₅₈O₉	633.400 1	633.402 7	4.1	471.346 4	粪便
C44	23.13	地榆皂苷Ⅱ, 原型(Ziyuglycoside Ⅱ，parent)	[M-H]^-	C₃₅H₅₆O₈	603.389 5	603.391 5	-3.3	585.380 3	粪便, 尿液
C45	21.76	3, 11-二酮-19α-羟基-乌苏-12-烯-28-酸, 原型(3，11-Dioxo-19α-hydroxy-urs-12-en-28-oic acid, parent)	[M+H]⁺	C₃₀H₄₄O₅	485.326 2	485.325 3	-1.8	439.321 5	粪便

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[5]	许维桐, 霍志鹏, 雷磊, 等. HPLC-IT-TOF/MS分析地榆水煎液的化学成分群[J]. 中草药, 2018, 49(6): 1277-1288. https://www.cnki.com.cn/Article/CJFDTOTAL-ZCYO201806008.htm
[6]	LACHOWICZ S, OSZMIA AN' SKI J, RAPAK A, et al. Profile and content of phenolic compounds in leaves, flowers, roots, and stalks of Sanguisorba officinalis L. determined with the LC-DAD-ESI-QTOF-MS/MS analysis and their in vitro antioxidant, antidiabetic, antiproliferative potency[J]. Pharmaceuticals, 2020, 13(8): 191. doi: 10.3390/ph13080191
[7]	王森业, 殷博迪, 王玉宁, 等. 不同方法提取地榆总三萜含量的比较及其抗氧化活性研究[J]. 食品研究与开发, 2019, 40(6): 111-115. doi: 10.3969/j.issn.1005-6521.2019.06.020
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基于UHPLC-Q-TOF/MS的地榆化学成分分析及大鼠体内代谢研究

doi: 10.14148/j.issn.1672-0482.2021.0897

作者简介:
裴玉琼, 女, 实验师, E-mail: 832002@njucm.edu.cn

通讯作者:
缪志伟, 男, 主治中医师, 主要从事脾胃病的方药研究, E-mail: zjgzy011@njucm.edu.cn

徐艺, 女, 主任中医师, 主要从事脾胃病的中医药防治研究, E-mail: fsyy00638@njucm.edu.cn

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Identification of Chemical Composition of Sanguisorba officinalis L. and Its Major Metabolites in Rats by UHPLC-Q-TOF/MS

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基于UHPLC-Q-TOF/MS的地榆化学成分分析及大鼠体内代谢研究

doi: 10.14148/j.issn.1672-0482.2021.0897

作者简介: 裴玉琼, 女, 实验师, E-mail: 832002@njucm.edu.cn

通讯作者: 缪志伟, 男, 主治中医师, 主要从事脾胃病的方药研究, E-mail: zjgzy011@njucm.edu.cn 徐艺, 女, 主任中医师, 主要从事脾胃病的中医药防治研究, E-mail: fsyy00638@njucm.edu.cn

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Identification of Chemical Composition of Sanguisorba officinalis L. and Its Major Metabolites in Rats by UHPLC-Q-TOF/MS

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出版历程

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作者简介:
裴玉琼, 女, 实验师, E-mail: 832002@njucm.edu.cn

通讯作者:
缪志伟, 男, 主治中医师, 主要从事脾胃病的方药研究, E-mail: zjgzy011@njucm.edu.cn

徐艺, 女, 主任中医师, 主要从事脾胃病的中医药防治研究, E-mail: fsyy00638@njucm.edu.cn