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Article(id=1200860517008003574, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1200860506031518620, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2023-1451, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1703606400000, receivedDateStr=2023-12-27, revisedDate=1709395200000, revisedDateStr=2024-03-03, acceptedDate=null, acceptedDateStr=null, onlineDate=1764237058164, onlineDateStr=2025-11-27, pubDate=1715443200000, pubDateStr=2024-05-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1764237058164, onlineIssueDateStr=2025-11-27, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1764237058164, creator=13701087609, updateTime=1764237058164, updator=13701087609, issue=Issue{id=1200860506031518620, tenantId=1146029695717560320, journalId=1189982191388893191, year='2024', volume='59', issue='5', pageStart='1101', pageEnd='1508', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1764237055547, creator=13701087609, updateTime=1764241222263, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1200877982563824311, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1200860506031518620, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1200877982563824312, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1200860506031518620, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=1382, endPage=1390, ext={EN=ArticleExt(id=1200860518153048620, articleId=1200860517008003574, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Identification of cajanonic acid A metabolites in rats by UPLC-Q-TOF-MS/MS, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

This research established a simple, rapid and sensitive ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) method to investigate the metabolic profiles of cajanonic acid A (CAA) in rats. After intragastric administration of CAA (30 mg·kg-1) to rats, the biological samples were detected by UPLC-Q-TOF-MS/MS. Relevant data was collected and processed, the accurate mass and MS2 spectra of the metabolites were compared with the parent compound. As a result, a total of 23 metabolites were detected, including 15 in urine, 11 in bile, 11 in feces, and 9 in plasma. The major metabolic pathways related to CAA included dehydrogenation, reduction, hydroxylation, methylation and glucuronide conjugation. This experiment was approved by Animal Ethics Committee of Guizhou Medical University (approval number: 1603137).

, correspAuthors=Jing HUANG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2024 Acta Pharmaceutica Sinica. All rights reserved., copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=null, magXml=null, pdfUrl=null, pdf=null, pdfFileSize=null, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=null, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=null, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=Yao CHENG, Yu-juan BAN, Rui CHEN, Li ZHANG, Ke-rong HU, Jing HUANG), CN=ArticleExt(id=1200860521483326232, articleId=1200860517008003574, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=UPLC-Q-TOF-MS/MS法鉴定大鼠中树豆酮酸A代谢产物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

本研究建立一种简便、快速、灵敏度高的超高效液相色谱串联四极杆-飞行时间质谱(UPLC-Q-TOF-MS/MS) 法, 研究树豆酮酸A (CAA) 在大鼠体内的代谢特征。通过灌胃给予大鼠CAA (30 mg·kg-1) 后, 收集血浆、尿液、胆汁和粪便采用UPLC-Q-TOF-MS/MS检测生物样品, 收集和处理相关数据, 将代谢产物的精确质量数和MS2质谱与母体化合物进行比较。结果共检测到23种代谢物, 其中尿液中有15种, 胆汁中有11种, 粪便中有11种, 血浆中有9种。与CAA相关的主要代谢途径包括脱氢、还原、羟基化、甲基化和葡萄糖醛酸结合。本实验获得贵州医科大学动物伦理委员会批准(编号: 1603137)。

, correspAuthors=黄静, authorNote=null, correspAuthorsNote=
*黄静, E-mail:
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The names of M0-M23 were listed in <a href="javascript:;" class="mag_content_a mag_xref_table" onclick="clickTabXref(this,'Table1')" rid="Table1">Table 1</a> , figureFileSmall=NyKchr5WJyz4GsUQWEk4Og==, figureFileBig=pkR/y/pCeuNL6y3H3UtJwQ==, tableContent=null), ArticleFig(id=1201106659251810744, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=EN, label=null, caption=null, figureFileSmall=dKyfv2r1p+Y5O3OBhiGYsQ==, figureFileBig=YJNkejRDANcG4s+vGWGF8w==, tableContent=null), ArticleFig(id=1201106659373445568, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=CN, label=Figure 3, caption= The MS<sup>2</sup> spectrum of major metabolite, M5 (A), M8 (B), M10 (C), M12 (D) , figureFileSmall=dKyfv2r1p+Y5O3OBhiGYsQ==, figureFileBig=YJNkejRDANcG4s+vGWGF8w==, tableContent=null), ArticleFig(id=1201106659549606349, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=EN, label=null, caption=null, figureFileSmall=pH5LG5Q+PmXRKBxDiSLw6g==, figureFileBig=DCV4v8VfthX66953mc9Fng==, tableContent=null), ArticleFig(id=1201106659742544343, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=CN, label=Figure 4, caption= Metabolic pathways for CAA in rat , figureFileSmall=pH5LG5Q+PmXRKBxDiSLw6g==, figureFileBig=DCV4v8VfthX66953mc9Fng==, tableContent=null), ArticleFig(id=1201106659868373472, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=EN, label=null, caption=null, figureFileSmall=lpb4JGu7VscX6ONKRRWUUQ==, figureFileBig=7kCKCJc1V+vAYKuCO9eCHA==, tableContent=null), ArticleFig(id=1201106660073894378, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=CN, label=Figure 5, caption= Mass spectrum of CAA , figureFileSmall=lpb4JGu7VscX6ONKRRWUUQ==, figureFileBig=7kCKCJc1V+vAYKuCO9eCHA==, tableContent=null), ArticleFig(id=1201106660262638069, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=EN, label=null, caption=null, figureFileSmall=6yHtXx2Sq2b4GbgpW9M+tw==, figureFileBig=sZu7tMUkPWbpg4Ot71Ny7A==, tableContent=null), ArticleFig(id=1201106660384272901, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=CN, label=Figure 6, caption= Fragmentation pathways of CAA in negative ion mode , figureFileSmall=6yHtXx2Sq2b4GbgpW9M+tw==, figureFileBig=sZu7tMUkPWbpg4Ot71Ny7A==, tableContent=null), ArticleFig(id=1201106660501713423, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=EN, label=null, caption=null, figureFileSmall=null, figureFileBig=null, tableContent=
No.RT /minMetabolite descriptionCalculated (m/z)Measured (m/z)Error (ppm)FormulaMS/MS fragment ionSource
M08.57M0353.138 9353.138 7-0.6C21H22O5311.155 6, 309.152 3, 293.118 1, 251.071 0, 239.070 9P, B, U, F
M15.19M0+H2+O+CH2385.165 1385.167 28.7C22H26O6313.115 8, 214.032 5U
M25.29M0+C6H8O6529.171 0529.170 2-1.7C27H30O11452.146 7, 409.140 6, 385.086 5 353.139 5B, U
M35.41M0+SO3433.095 7433.095 5-0.5C21H22O8S146.996 0U, F
M45.53M0+H2+C6H8O6531.186 6531.186 5-0.1C27H32O11401.087 9, 311.129 0, 269.045 7, 241.050 2, 225.055 1U
M55.65M0+O+O385.128 7385.128 90.6C21H22O7341.139 4, 323.128 7, 311.128 7, 281.117 8, 240.079 0P, B, U, F
M66.01M0+H2-H2O+C6H8O6513.176 1513.175 7-0.8C27H30O10401.087 6U
M76.02M0+H2+CH2369.170 2369.173 28.7C22H26O5351.123 5U
M86.70M0+O369.133 8369.134 10.7C21H22O6351.124 1, 325.144 8, 295.134 0, 251.071 4P, B, U, F
M96.78M0-H2O+CH2349.144 0349.143 4-1.9C22H22O4339.123 8, 295.134 0, 279.102 6U
M106.79M0+O+O-H2383.113 1383.113 40.6C21H20O7339.123 8, 321.113 1, 295.134 0, 279.102 6P, B, U, F
M116.86M0+H2+O371.149 5371.148 7-2.1C21H24O6255.102 3, 146.965 9P, U
M127.30M0+O-H2367.118 2367.118 30.1C21H20O6349.108 0, 334.084 1, 323.128 9, 295.133 8, 251.071 1P, B, U
M137.71M0+H2+H2+C2H2O399.180 8399.180 4-0.9C23H28O6249.149 5P, B, U
M1410.85M0+H2355.154 5355.157 27.6C21H24O5311.167 9, 293.160 5, 146.966 0P, B, U, F
M1511.32M0+H2+H2-O+C2H2O383.185 8383.187 75.0C23H28O5325.183 3, 311.167 5, 265.247 2P, B, U
M1610.51M0+H2-H2O+C2H2O379.154 5379.157 37.3C23H24O5361.147 5P, B, F
M176.20M0+C2H3NO+C3H5NO2S529.164 5529.166 74.2C26H30N2O8S353.139 5B
M185.06M0-H2O+C3H5NOS438.137 5438.136 0-3.5C24H25NO5S425.169 7, 413.162 9, 357.101 2, 343.132 9B
M195.70M0+H2+SO3435.111 4435.111 0-1.0C21H24O8S353.138 5, 341.138 4, 323.127 2, 321.112 3, 307.094 2, 285.112 7, 267.102 0, 241.122 7F
M205.71M0+O-H2+SO3447.075 0447.074 1-2.0C21H20O9S353.138 5, 321.112 3F
M214.95M0+H2+O+SO3451.106 3451.106 60.8C21H24O9S313.108 3, 253.050 6, 149.024 3F
M225.61M0+O+SO3449.090 6449.089 8-1.9C21H22O9S357.060 2, 313.070 7, 269.044 7F
M233.99M0-CH2+C10H15N3O6S644.191 4644.197 39.6C30H35N3O11S601.216 0, 209.045 3F
), ArticleFig(id=1201106660640125463, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200860517008003574, language=CN, label=Table 1, caption=

Results of UPLC-Q-TOF-MS/MS analysis of cajanonic acid A (CAA). M0 denotes the prototype of the compound. P: Plasma; B: Bile; U: Urine; F: Feces

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No.RT /minMetabolite descriptionCalculated (m/z)Measured (m/z)Error (ppm)FormulaMS/MS fragment ionSource
M08.57M0353.138 9353.138 7-0.6C21H22O5311.155 6, 309.152 3, 293.118 1, 251.071 0, 239.070 9P, B, U, F
M15.19M0+H2+O+CH2385.165 1385.167 28.7C22H26O6313.115 8, 214.032 5U
M25.29M0+C6H8O6529.171 0529.170 2-1.7C27H30O11452.146 7, 409.140 6, 385.086 5 353.139 5B, U
M35.41M0+SO3433.095 7433.095 5-0.5C21H22O8S146.996 0U, F
M45.53M0+H2+C6H8O6531.186 6531.186 5-0.1C27H32O11401.087 9, 311.129 0, 269.045 7, 241.050 2, 225.055 1U
M55.65M0+O+O385.128 7385.128 90.6C21H22O7341.139 4, 323.128 7, 311.128 7, 281.117 8, 240.079 0P, B, U, F
M66.01M0+H2-H2O+C6H8O6513.176 1513.175 7-0.8C27H30O10401.087 6U
M76.02M0+H2+CH2369.170 2369.173 28.7C22H26O5351.123 5U
M86.70M0+O369.133 8369.134 10.7C21H22O6351.124 1, 325.144 8, 295.134 0, 251.071 4P, B, U, F
M96.78M0-H2O+CH2349.144 0349.143 4-1.9C22H22O4339.123 8, 295.134 0, 279.102 6U
M106.79M0+O+O-H2383.113 1383.113 40.6C21H20O7339.123 8, 321.113 1, 295.134 0, 279.102 6P, B, U, F
M116.86M0+H2+O371.149 5371.148 7-2.1C21H24O6255.102 3, 146.965 9P, U
M127.30M0+O-H2367.118 2367.118 30.1C21H20O6349.108 0, 334.084 1, 323.128 9, 295.133 8, 251.071 1P, B, U
M137.71M0+H2+H2+C2H2O399.180 8399.180 4-0.9C23H28O6249.149 5P, B, U
M1410.85M0+H2355.154 5355.157 27.6C21H24O5311.167 9, 293.160 5, 146.966 0P, B, U, F
M1511.32M0+H2+H2-O+C2H2O383.185 8383.187 75.0C23H28O5325.183 3, 311.167 5, 265.247 2P, B, U
M1610.51M0+H2-H2O+C2H2O379.154 5379.157 37.3C23H24O5361.147 5P, B, F
M176.20M0+C2H3NO+C3H5NO2S529.164 5529.166 74.2C26H30N2O8S353.139 5B
M185.06M0-H2O+C3H5NOS438.137 5438.136 0-3.5C24H25NO5S425.169 7, 413.162 9, 357.101 2, 343.132 9B
M195.70M0+H2+SO3435.111 4435.111 0-1.0C21H24O8S353.138 5, 341.138 4, 323.127 2, 321.112 3, 307.094 2, 285.112 7, 267.102 0, 241.122 7F
M205.71M0+O-H2+SO3447.075 0447.074 1-2.0C21H20O9S353.138 5, 321.112 3F
M214.95M0+H2+O+SO3451.106 3451.106 60.8C21H24O9S313.108 3, 253.050 6, 149.024 3F
M225.61M0+O+SO3449.090 6449.089 8-1.9C21H22O9S357.060 2, 313.070 7, 269.044 7F
M233.99M0-CH2+C10H15N3O6S644.191 4644.197 39.6C30H35N3O11S601.216 0, 209.045 3F
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UPLC-Q-TOF-MS/MS法鉴定大鼠中树豆酮酸A代谢产物
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程瑶 1, 2 , 班玉娟 1 , 陈瑞 1 , 张丽 1 , 胡克荣 1, 2 , 黄静 2, *
药学学报 | 研究论文 2024,59(5): 1382-1390
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药学学报 | 研究论文 2024, 59(5): 1382-1390
UPLC-Q-TOF-MS/MS法鉴定大鼠中树豆酮酸A代谢产物
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程瑶1, 2, 班玉娟1, 陈瑞1, 张丽1, 胡克荣1, 2, 黄静2, *
作者信息
  • 1.贵州医科大学, 贵州省化学合成药物研发利用工程技术研究中心, 贵州 贵阳 550004
  • 2.贵州医科大学药学院, 贵州 贵阳 550004

通讯作者:

*黄静, E-mail:
Identification of cajanonic acid A metabolites in rats by UPLC-Q-TOF-MS/MS
Yao CHENG1, 2, Yu-juan BAN1, Rui CHEN1, Li ZHANG1, Ke-rong HU1, 2, Jing HUANG2, *
Affiliations
  • 1. Guizhou Medical University, Guizhou Provincial Engineering Technology Research Center for Chemical Drug R & D, Guiyang 550004, China
  • 2. School of Pharmacy, Guizhou Medical University, Guiyang 550004, China
出版时间: 2024-05-12 doi: 10.16438/j.0513-4870.2023-1451
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摘要
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本研究建立一种简便、快速、灵敏度高的超高效液相色谱串联四极杆-飞行时间质谱(UPLC-Q-TOF-MS/MS) 法, 研究树豆酮酸A (CAA) 在大鼠体内的代谢特征。通过灌胃给予大鼠CAA (30 mg·kg-1) 后, 收集血浆、尿液、胆汁和粪便采用UPLC-Q-TOF-MS/MS检测生物样品, 收集和处理相关数据, 将代谢产物的精确质量数和MS2质谱与母体化合物进行比较。结果共检测到23种代谢物, 其中尿液中有15种, 胆汁中有11种, 粪便中有11种, 血浆中有9种。与CAA相关的主要代谢途径包括脱氢、还原、羟基化、甲基化和葡萄糖醛酸结合。本实验获得贵州医科大学动物伦理委员会批准(编号: 1603137)。

树豆酮酸A  /  UPLC-Q-TOF-MS/MS  /  代谢产物

This research established a simple, rapid and sensitive ultra-high-performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF-MS/MS) method to investigate the metabolic profiles of cajanonic acid A (CAA) in rats. After intragastric administration of CAA (30 mg·kg-1) to rats, the biological samples were detected by UPLC-Q-TOF-MS/MS. Relevant data was collected and processed, the accurate mass and MS2 spectra of the metabolites were compared with the parent compound. As a result, a total of 23 metabolites were detected, including 15 in urine, 11 in bile, 11 in feces, and 9 in plasma. The major metabolic pathways related to CAA included dehydrogenation, reduction, hydroxylation, methylation and glucuronide conjugation. This experiment was approved by Animal Ethics Committee of Guizhou Medical University (approval number: 1603137).

cajanonic acid A  /  UPLC-Q-TOF-MS/MS  /  metabolite
程瑶, 班玉娟, 陈瑞, 张丽, 胡克荣, 黄静. UPLC-Q-TOF-MS/MS法鉴定大鼠中树豆酮酸A代谢产物. 药学学报, 2024 , 59 (5) : 1382 -1390 . DOI: 10.16438/j.0513-4870.2023-1451
Yao CHENG, Yu-juan BAN, Rui CHEN, Li ZHANG, Ke-rong HU, Jing HUANG. Identification of cajanonic acid A metabolites in rats by UPLC-Q-TOF-MS/MS[J]. Acta Pharmaceutica Sinica, 2024 , 59 (5) : 1382 -1390 . DOI: 10.16438/j.0513-4870.2023-1451
正文
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糖尿病(diabetes mellitus, DM) 是一种由于胰岛素分泌绝对或相对不足, 胰岛素对靶组织的敏感性降低而导致葡萄糖、蛋白质和脂肪代谢紊乱的疾病[1-3]。2019年, 糖尿病约导致420万20~79岁人群死亡, 占全因死亡率的11.3%[4]。此外, 糖尿病患者由于持续高血糖, 伴有肝损害、血脂水平异常、心血管疾病、眼部病变、肾脏疾病等多种并发症[5-10]。这表明, DM正成为威胁人类健康的主要疾病, 因此, 开发更多安全、有效的降糖药具有重要意义。
树豆酮酸A (cajanonic acid A, CAA, 图 1) 是从豆科植物树豆Cajanus cajan (Linn.) Millsp.中提取的一种菧类化合物。已证明CAA具有良好的血糖控制和脂质代谢调节作用。CAA治疗可显著逆转地塞米松诱导和/或蛋白酪氨酸磷酸酶1B (PTP1B) 介导的胰岛素抵抗; CAA通过抑制PTP1B和下调过氧化物酶体增殖物激活受体-γ (PPARγ) 的表达, 抑制激素介导的脂肪形成。同时, PPARγ下调有助于预防典型噻唑烷二酮类PPARγ激活剂引起的不良反应[11-15]。因此, CAA是治疗糖尿病的潜在候选药物, 也是开发更多新型糖尿病药物的有利先导化合物。研究CAA的药代动力学、毒性和疗效变得越来越重要。根据前期研究, CAA在体内可被快速吸收, 但在大鼠尿液、胆汁、粪便中只有5.17%的CAA作为原型被排除, 此外, 据组织分布研究, 在口服CAA12 h后, 各组织中仅有11.86%的CAA原型, 推测CAA可能以代谢物[16]的方式排出。药物代谢可能会导致活性或毒性反应, 药物代谢研究可以帮助识别药物的活性或毒性成分, 在新药的发现和开发中占有重要的地位[17]。关于CAA的代谢数据尚未被报道。因此, 有必要对CAA代谢物进行检测, 以便更好地探索其安全性和有效性。
在众多数据采集和挖掘技术中, UPLC-Q-TOF-MS/MS由于其速度快、检测灵敏度高、分辨率高, 在药物代谢研究中发挥着至关重要的作用[18, 19]。UPLC系统具有峰容量大、分离效率高的特点, 广泛应用于复杂样品的分离。此外, Q-TOF-MS系统能够产生精确的质量数据, 并确定代谢产物的元素组成, 在Q-TOF-MS体系中, MS/MS和MSE获取技术为母体化合物和相应代谢物提供碎片离子, 是推测可能结构的必要数据资源[20-25]。MSE获取技术是Waters质谱独有的数据采集模式, 可以在“无碰撞能”和“高碰撞能”两种功能之间快速切换, 从而在单次分析中无缝收集母离子和碎片离子的全面信息, 具有全面、精准、简单和灵活的特点。
本研究采用UPLC-Q-TOF-MS/MS技术, 建立了一种高效、快速检测和表征大鼠血浆、胆汁、尿液和粪便中CAA代谢物的方法, 为进一步研究CAA的药理作用和机制提供有用的信息, 也为CAA的初步安全性评价提供了必要的数据。
材料与方法
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主要仪器  代谢笼(意大利Tecniplast公司), UPLC-Q-TOF (型号Xevo G2-XS, 美国Waters公司), 氮气吹扫仪(型号JN300-2, 苏州吉米诺仪器有限公司), 高速离心机(型号X1, 香港基因有限公司), 十万分之一电子天平(型号FA805N, 上海菁海仪器有限公司) 等。
化学品和试剂  CAA (贵州医科大学药物化学重点实验室制备, 纯度 > 98%), 水为屈臣氏蒸馏水, HPLC级乙酸乙酯(上海泰坦科技股份有限公司), LC/MS级甲酸(美国赛默飞公司), HPLC级甲醇和乙腈(德国Merck公司), OASIS HLB固相萃取(SPE) 柱(美国Waters公司)。
动物及药物管理  雄性SD大鼠, 体重200~230 g, 由长沙天勤生物技术有限公司(中国长沙) 提供, 实验动物许可证号: SCXK (湘) 2019-0014。实验前7天, 在室温(22 ± 2 ℃) 进行12 h的光照和黑暗循环饲养。实验前禁食12 h, 自由饮水。将18只SD大鼠随机分为3组, 分别为1组(血浆样品)、2组(尿液和粪便样品) 和3组(胆汁样品)。CAA (7.5 mg·mL-1) 溶于N-N-二甲基乙酰胺∶PEG400∶水(2∶4∶1), 以30 mg·kg-1的剂量进行灌胃给药。本实验获得贵州医科大学动物伦理委员会批准(编号: 1603137)。
样品采集  口服CAA, 给药前取空白血, 给药后0.1、0.25、0.5、1、2、4、6、8、10、12、16、20、24 h从肝门静脉取实验血浆样品放入肝素化的聚乙烯管内, 立即在3 000 r·min-1, 4 ℃下离心10 min, 分离血浆。
将2组6只大鼠置于代谢笼中, 于给药前12 h采集空白尿液和粪便样品, 在给药后4、8、12、24、36、48 h分别采集尿液和粪便样品。采集的粪便样品在37 ℃下干燥, 粉碎成粉末, 再将所得粉末以冰甲醇/水(7∶3, v/v) 按1∶10的比例(w/v) 均质, 20 000 r·min-1离心10 min, 收集粪便上清液。
三组6只大鼠在给药前腹腔注射10%水合氯醛溶液。腹部切开, 用聚乙烯管连接胆总管收集胆汁, 然后缝合切口, 采用加热灯保持大鼠体温。给药前2 h获得空白胆汁, 给药后1、2、4、6、8、10、12、24、36 h取大鼠胆管胆汁。所有采集的样品均保存在-80 ℃下, 以备后续使用。
样品制备  采用HLB固相萃取柱对粪便、尿液和胆汁样本进行预处理。首先, 取HLB固相萃取柱, 向其加1 mL甲醇, 再加1 mL水进行活化小柱后备用。然后将1 mL尿样加入到HLB固相萃取柱中, 用3倍柱体积水淋洗, 而后加3倍柱体积甲醇进行洗脱, 收集甲醇洗脱液, 将其置于37 ℃氮气下吹干, 用200 μL甲醇溶解残渣, 20 000 r·min-1离心10 min。取2 μL上清液用于UPLC-Q-TOF-MS/MS分析。粪便和胆汁样本(1 mL) 采用相同的方法处理。
采用液-液萃取法从大鼠血浆中提取CAA。用800 μL乙酸乙酯沉淀100 μL的血浆样品, 涡旋震荡5 min, 20 000 r·min-1离心10 min。收集上清液, 加入离心管(1.5 mL), 将其置于37 ℃氮气下吹干。用200 μL甲醇溶解残渣, 20 000 r·min-1离心10 min。取2 μL上清液用于UPLC-Q-TOF-MS/MS分析。
色谱条件  采用Waters ACQUITY UPLC® BEH C18色谱柱(50 mm × 2.1 mm, 1.7 μm)。梯度洗脱采用溶剂A (由0.01%甲酸和水组成, v/v) 和溶剂B (由0.01%甲酸和乙腈组成, v/v), 梯度洗脱过程为0~2 min 5% B, 2~3 min 5%~35% B, 3~6.5 min 35%~48% B, 6.5~12 min 48%~95% B, 12~13 min 95%~98% B, 13~15 min 98%~5% B。进样量2 μL, 流速0.4 mL·min-1, 柱温40 ℃。
质谱条件  电喷雾离子源(ESI), 负模式采集, 毛细管电压-1.5 kV, 溶剂气温度400 ℃, 离子源温度120 ℃, 脱溶剂气(N2) 流量800 L·h-1, 锥孔气流量50 L·h-1, 质量范围为m/z 50~1 200。使用亮氨酸脑啡肽作为校正液, 在4 eV恒定碰撞能量下, 获得低能MSE模式下的所有MS数据, 得到母离子数据。然后, 利用20~25 eV碰撞能量在高能MSE模式下获得最佳碎裂数据。同时, 采用美国Waters公司的MassLynx V 4.1进行系统控制。
数据处理  数据采集由MasslynxTM v4.1软件以负离子模式执行, 并由UNIFITMv1.8软件进行处理。MSE模式下的参数设置如下: 加合物的选择, 负模式为H-、Cl-、HCOO-。保留时间范围: 0~15 min; 保留时间容差为0.1 min; 目标质量匹配容差为2.0 mDa; 结构预测片段的匹配容差为5.0 mDa; 在高能量下≥ 100个计数的强度阈值, 在低能量下≥ 500个计数的强度阈值; 质量缺陷过滤器, 50 mDa。将不同类型的特征片段和中性分子设置为普通片段和普通中性损失模式, 质量容差在2.0 mDa以内。预期使用的潜在生物转化规则为去饱和、还原、氧化、脱水、水合、葡萄糖醛酸化、甲基化、乙酰化、硫酸化、去甲基化、脱羧、脱羟基、谷胱甘肽结合、甘氨酸结合、半胱氨酸结合和乙酰半胱氨酸结合。基于精确的质量离子和碎片离子, 在UNIFI平台上进行了自动匹配分析。
结果
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采用UPLC-Q-TOF-MS/MS和MSE模式对每个生物样品进行检测, 可在一个质谱周期内同时对高、低碰撞能量进行全扫描。该方法可简单、快速地获得了该组分的母离子和子离子信息, 将获得的质谱数据与UNIFI软件结合, 对CAA代谢产物进行分析。在UNIFI软件中, 首先从样品色谱图中减去空白基质色谱图, 由原型化合物CAA建立的专属数据库显示了特有的质谱信息。结果表明, 口服CAA后, 在大鼠血浆、尿液、粪便和胆汁样本中测定了23种代谢物。主要代谢物的基峰强度(base peak intensity, BPI) 色谱图和MS2质谱分别如图 2、3所示。图 4所示为大鼠尿液、粪便、胆汁、血浆中CAA的代谢途径。保留时间、元素组成、MS/MS片段、计算的m/z值和质量误差见表 1。
1 CAA标准品的碎裂
为鉴定CAA代谢物, 本实验首先研究了其母体化合物的质量碎裂行为。质谱检测采用电喷雾离子源, 负离子模式采集。图 5为CAA的质谱, 图 6为CAA的碎裂路径。全扫描质谱分析显示, 在m/z 353.138 9处检测到准分子离子峰[M-H]-。从质谱图上可以看出, 主要的碎片离子有m/z 311.155 6、m/z 309.152 3、m/z 293.118 1、m/z 251.071 0和m/z 239.070 9。推测m/z 311.155 6处的碎片离子是由于异戊烯基上的双键断裂。而CAA中羧基的缺失导致了m/z 309.152 3处的碎片离子, m/z 293.118 1处的碎片离子则是进一步失去一个羟基而生成的, m/z 251.071 0处的碎片离子是由m/z 293.118 1上的异戊烯基双键断裂引起的, m/z 239.070 9处的碎片离子是由进一步失去一个CH3分子而得到的。
2 CAA代谢产物的结构解析
M1、M7、M14: 代谢物M14在10.85 min洗脱, 在m/z 355.154 5处观察到准分子离子峰, 元素组成为C21H24O5, 比CAA多2 Da (+H2)。从其MS2质谱中可以观察到典型的碎片离子在m/z 146.966 0 (异戊基苯) 处, 推测M14是通过CAA的异戊基上的双键还原得到的。此外, 如果CAA的酮羰基被还原, 应提高其极性, 缩短保留时间。但M14的保留时间比CAA长(RT = 8.57 min), 证明在酮羰基上没有发生还原反应。在m/z 369.170 2处检测到M7的[M-H]-离子(RT = 6.02 min), 比CAA多16 Da。M7的元素组成为C22H26O5, 相当于CAA+H2+CH2。结合UNIFI数据库分析, 推断M7为CAA的C=C双键还原和甲基化代谢产物。M1的保留时间为5.19 min, [M-H]-离子在m/z 385.165 1处, M1比CAA多32 Da, 元素组成为C22H26O6, MS2质谱中, 在m/z 313.115 8 ([M0-C3H6]-) 和214.035 2 ([M0-C5H10-CH3-OH-COOH]-) 处观察到产物离子。结合UNIFI数据库分析, 初步鉴定M1为CAA的还原、甲基化、羟基化代谢产物, 为M7的羟基化产物。在CAA结构中, 羰基双键与相邻的苯环形成共轭键, 比异戊烯基的孤立双键更稳定。因此, 还原可能首先发生在异戊烯基的双键上。由于苯环上的羰基是一个吸电子基团, 使得苯环上的羟基化反应更难发生。相比之下, 烯丙基更容易发生羟基化, 推测是在异戊烯基末端的一个甲基上发生羟基化。
M2、M4、M6、M16: m/z 529.171 0 ([M-H]-) 代谢物M2在5.29 min洗脱, 元素成分为C27H30O11, 比CAA多176 Da。M2在m/z 353.139 5处有特征产物离子, 与CAA的[M-H]-相同。因此, 它可能来源于CAA的葡萄糖醛酸结合反应。此外, m/z 452.146 7 ([M2-OCH3-COOH]-)、409.140 6 ([M2-C8H8O]-) 和385.086 5 ([M2-C5H10-C6H6]-) 的典型碎片离子表明, 葡萄糖醛酸结合反应发生在CAA的酚羟基上。M4 (RT = 5.53 min) 在m/z 531.186 6处有[M-H]-离子, 元素组成为C27H32O11, 比M2多2 Da (+H2), 比CAA多178 Da (+C6H8O6、+H2)。因此, M4被确定为CAA的葡萄糖醛酸结合反应和还原代谢物。从MS2质谱中观察到, 在m/z 269.045 7 ([M0-CH3-C5H10]-) 处检测到一个产物离子, 推测还原反应发生在异戊烯基的双键上。此外, 还发现了m/z 401.087 9 ([M4-CH3-C5H10-COOH]-) 和225.055 1 ([M0-CH3-C5H10-COOH]-) 两种典型的产物离子, 表明葡萄糖醛酸结合反应发生在CAA的酚羟基上。M6 (RT = 6.01 min) 在m/z 513.176 1处有一个[M-H]-离子, 分子式为C27H30O10, 比M2少一个O元素。由此推测, M6可能是CAA的葡萄糖醛酸结合和脱氧代谢物。结合UNIFI数据库分析, 通过氢化还原、葡萄糖醛酸结合得到M6。根据文献[11], 在CAA合成的最后一步, 不饱和内酯水解得到最终产物CAA。由此推断CAA是通过脱水得到不饱和内酯, 并通过对异戊烯基的氢化还原和对酚羟基的葡萄糖醛酸结合得到M6。M16 (RT = 10.51 min) 在m/z 379.154 5处检测到[M-H]-离子, 元素组成为C23H24O5。结合UNIFI数据库分析, M16被鉴定为CAA的乙酰化和脱氧代谢产物。与M6一样, M16也经历了相同的脱水和加氢还原反应。
M3、M19、M21、M22: M3在5.41 min洗脱, 在m/z 433.095 7处检测到[M-H]-离子, 分子式为C21H22O8S, 比CAA多80 Da (+SO3)。因此, M3被鉴定为CAA的硫酸盐结合代谢物。M19 (RT = 5.70 min) 在m/z 435.111 4处有一个[M-H]-离子, 其元素组成为C21H24O8S, 比CAA多82 Da (+H2、+SO3), 比M3多2 Da (+H2)。因此, 初步确定M19为CAA的还原和硫酸盐结合代谢物。代谢物M21在m/z 451.106 3处有[M-H]-离子, 元素组成为C21H24O9S, 在4.95 min检测到, 比M19多16 Da (+O), 推测M21比M19多进行了一次羟基化。5.61 min洗脱产物M22, 在m/z 449.090 6处检测到[M-H]-离子, 分子式为C21H22O9S, 比M3多16 Da (+O)。因此, M22被确定为CAA的羟基化和硫酸盐结合产物。
M5、M10: M5在5.65 min检测到, [M-H]-离子在m/z 385.128 7处。M5的分子式为C21H22O7, 比CAA多了两个O原子。同时, 其典型的碎片离子包括m/z 341.139 4 ([M5-COOH]-)、323.128 7 ([M5-OH-COOH]-)、311.128 7 ([M5-(CH2OH)2-CH3]-)、281.117 8 ([M5-OH-COOH-C2H2(CH2OH)2]-) 和240.079 0 ([M5-OH-COOH-C2H2(CH2OH)2]-), 判断是在异戊烯基末端的两个甲基上羟基化。此外, 代谢产物M10 (RT = 6.79 min) 在m/z 383.113 1处出现[M-H]-离子, 比M5少2 Da, 比CAA多30 Da。从MS2质谱中可以看出, M10在m/z 339.123 8和321.113 1处出现了产物离子, 均比M5少2 Da, 说明它是M5的脱氢代谢物。M10的其他产物离子在m/z处分别为295.134 0 ([M10-OH-COOH-CH2OH]-) 和279.102 6 ([M10-OH-COOH-CH2OH]-)。因此, 判断M10是由M5的一个醇羟基氧化成醛而来的。
M8、M12、M20: M8 (RT = 6.70 min), [M-H]-离子在m/z 369.133 8处检测到。M8的元素组成为C21H22O6, 比CAA多1个O元素。此外, 其典型的碎片离子包括m/z 351.124 1 ([M8-OH]-)、325.144 8 ([M8-COOH]-)、295.134 0 ([M8-COOH-OCH3]-) 和251.071 4 ([M8-COOH-OH-C3H5OH]-), 这表明它是在CAA的异戊烯基末端的一个甲基上被羟基化的。M12 (RT = 7.30 min) 在m/z 367.118 2处有[M-H]-离子, 元素组成为C21H20O6, 比M8少2 Da (-H2)。同时在m/z 295.133 8和251.071 1处检测到M12的典型碎片离子, 与M8相同。在m/z 349.108 0处检测到另一个碎片离子, 比M8少2 Da。因此, 可以推断M12是由M8的醇羟基氧化生成醛而来的。M20在5.71 min检测到, [M-H]-离子在m/z 447.070 5检测到, 元素组成为C21H20O9S, 比M12多80 Da (+SO3)。因此, 确定M20为M12的硫酸盐结合产物。
M9: 代谢产物M9在6.78 min洗脱, 在m/z 349.144 0处观察到[M-H]-离子, 其元素组成为C22H22O4。M9的MS2质谱中, 在m/z处分别检测到339.123 8 ([M9-CH2]-)、295.134 0 ([M9-CH2-C3H6]-) 和279.102 6 ([M9-CH2-C4H9]-) 的典型碎片离子。结合UNIFI数据库分析, 推断M9为CAA脱水和甲基化代谢产物。推测脱水反应包括两个步骤, 羰基酮-烯醇互变反应, 然后脱水形成不饱和内酯。
M11: 代谢产物M11在6.86 min洗脱, 在m/z 371.149 5处观察到[M-H]-离子, 其元素组成为C21H24O6, 比CAA多18 Da (+H2、+O)。因此, 初步推测M11来源于CAA的还原和羟基化。
M13、M15: M13和M15分别在7.71和11.32 min检测到。M13在m/z 399.180 8处观察到[M-H]-离子, 其元素组成为C23H28O6。结合UNIFI数据库分析, 推测M13是通过两个双键上的还原反应和乙酰化反应得到的。由于CAA的两个苯环相对稳定, 可能会在异戊烯基和羰基的双键上发生还原反应。M15在m/z 383.185 8处观察到[M-H]-离子。M15的元素组成为C23H28O5, 比M13少1个O原子。同时, 在m/z 325.183 3 ([M15-COOH-CH3]-) 和265.247 2 ([M15-OH-COOH-OCH3-(CH3)2]-) 处检测到其碎片离子, 推测M15比M13多进行了一次脱羟基反应。
M17: M17在6.20 min洗脱, M17在m/z 529.165 4处有[M-H]-离子, 元素组成为C26H30N2O8S。比CAA多176 Da (+C2H3NO、+C3H5NO2S)。在m/z 353.139 5处发现了主要的碎片离子, 与母体化合物的准分子离子相同。因此, 初步确定M17为CAA的甘氨酸结合和S-半胱氨酸结合代谢物。
M18: M18在5.06 min洗脱, 在m/z 438.137 5处有[M-H]-离子, 分子式为C24H25NO5S。比CAA多85 Da (+C3H5NOS、-H2O)。因此, 初步确定M18为CAA的脱水和半胱氨酸结合代谢物, 脱水反应过程与M9相同。
M23: 在3.99 min洗脱, M23在m/z 644.191 4处有[M-H]-离子, 分子式为C30H35N3O11S。与CAA相比, M23的[M-H]-离子增加了291 Da (+C10H15N3O6S、-CH2), 在m/z 601.216 0 ([M23-OH-(CH3)2]-) 和209.045 3 ([M23-OH-COOH-C5H10-C10H15N3O6S]-) 处可见典型的碎片离子。因此, 初步确定M23为CAA的去甲基化和S-谷胱甘肽结合代谢物。根据文献[26], 当甲氧基附着在苯环上时, 很容易失去一个甲基, 推测CAA的甲氧基失去了一个甲基分子。
讨论
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本研究建立了一种快速、高效、可靠的UPLC-Q-TOF-MS/MS方法, 并结合UNIFI软件对口服CAA后大鼠血浆、尿液、粪便和胆汁样本中的代谢物进行鉴定。基于精确的质量测量、相关药物转化数据和特征碎片离子, 本文方法共检测了23个代谢物。与CAA相关的代谢途径包括Ⅰ相(羟基化、水解和还原) 和Ⅱ相(硫酸盐结合、葡萄糖醛酸结合、半胱氨酸结合、甘氨酸结合和S-谷胱甘肽结合) 代谢途径。基底峰强度(BPI) 谱图显示, 代谢产物M5、M8、M10和M12的反应明显高于CAA。说明在体内, 脱氢和羟基化是CAA的主要代谢途径。结合既往研究, 只有5.17%的CAA以原型[16]的形式排出, 推测CAA主要以代谢物的形式排出。本实验结果为了解CAA在大鼠体内的代谢和安全性提供了研究基础。关于菧类化合物的报道较少, 本研究有助于了解该类化合物在体内的生物转化规律, 可为该类化合物的进一步研究和开发提供参考。
作者贡献: 程瑶、班玉娟完成数据收集、分析及文章撰写; 张丽、胡克荣协助完成动物实验; 陈瑞设计实验并提供学术指导; 黄静协助指导实验并审核文章。
利益冲突: 本文不存在任何利益冲突。
基金
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  • 国家自然科学基金资助项目(81660573)
  • 贵州省科技计划项目(黔科合支撑[2017]2842)
  • 贵州省科技计划项目(黔科中引地[2022]4017)
  • 贵州省教育厅服务“四新”“四化”科技攻关项目(黔教技[2022]004)
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2024年第59卷第5期
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文章信息
doi: 10.16438/j.0513-4870.2023-1451
  • 接收时间：2023-12-27
  • 首发时间：2025-11-27
  • 出版时间：2024-05-12
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  • 收稿日期：2023-12-27
  • 修回日期：2024-03-03
基金
国家自然科学基金资助项目(81660573)
贵州省科技计划项目(黔科合支撑[2017]2842)
贵州省科技计划项目(黔科中引地[2022]4017)
贵州省教育厅服务“四新”“四化”科技攻关项目(黔教技[2022]004)
作者信息
    1.贵州医科大学, 贵州省化学合成药物研发利用工程技术研究中心, 贵州 贵阳 550004
    2.贵州医科大学药学院, 贵州 贵阳 550004

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2种不同金属材料的力学参数
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species		 占总种数比例
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鹅膏菌科Amanitaceae 2 11 5.26 鹅膏菌属 Amanita 10 4.78
小菇科 Mycenaceae 2 12 5.74 丝盖伞属 Inocybe 5 2.39
多孔菌科 Polyporaceae 8 14 6.70 蜡蘑属 Laccaria 5 2.39
红菇科 Russulaceae 3 23 11.00 小皮伞属 Marasmius 6 2.87
小菇属 Mycena 11 5.26
光柄菇属 Pluteus 5 2.39
红菇属 Russula 17 8.13
栓菌属 Trametes 5 2.39
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