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Article(id=1198628610824302964, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198628599835227075, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2023-0067, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1674748800000, receivedDateStr=2023-01-27, revisedDate=1676822400000, revisedDateStr=2023-02-20, acceptedDate=null, acceptedDateStr=null, onlineDate=1763704930262, onlineDateStr=2025-11-21, pubDate=1686499200000, pubDateStr=2023-06-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1763704930262, onlineIssueDateStr=2025-11-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1763704930262, creator=13701087609, updateTime=1763704930262, updator=13701087609, issue=Issue{id=1198628599835227075, tenantId=1146029695717560320, journalId=1189982191388893191, year='2023', volume='58', issue='6', pageStart='0', pageEnd='1724', issueExtLink='null', onlineDate='null', pubDate='1686499200000', pubDateStr='2023-06-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1763704927643, creator='13701087609', updateTime=1766137690373, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1208832346359468483, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198628599835227075, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1208832346359468484, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198628599835227075, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=1650, endPage=1654, ext={EN=ArticleExt(id=1198628611172430231, articleId=1198628610824302964, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Two new ursane triterpenoids from Agastache rugosa (Fisch. et.Mey.) O. Kuntze, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Two new ursane triterpenoids along with twelve known compounds were isolated from 80% ethanol extract of Agastache rugosa (Fisch. et. Mey.) O. Kuntze by using silica gel column, MCI column, ODS column and HPLC. The structures of the new compounds were identified as 2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13)-dien-28-oic acid (1) and 2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13), 20(30) -trien-28-oic acid (2) by HR-ESI-MS, NMR and ECD spectral data, named agasursacid A and agasursacid B. In addition, compounds 3, 4, 6, 8 showed anti-coxsackievirus B3 (CVB3) activities with a IC50 as 4.77, 1.59, 11.11 and 25.87 μmol·L-1, resepectively.

, authors=null, authorsList=Ya-ting REN, Bei LI, Jie MA, Yu-huan LI, Ying-da ZANG, Chuang-jun LI, Dong-ming ZHANG, authorCompany=null, correspAuthors=Chuang-jun LI, Dong-ming ZHANG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2023 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, fund=null), CN=ArticleExt(id=1198628612392972796, articleId=1198628610824302964, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=藿香中的两个新乌苏烷型三萜, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶、MCI、ODS柱色谱和高效制备液相色谱等方法, 从藿香80%乙醇提取物中分离得到2个新乌苏烷型三萜和12个已知化合物。通过质谱、核磁共振和ECD等波谱学方法鉴定新化合物的结构分别为2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13)-dien-28-oic acid (1)和2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13), 20(30)-trien-28-oic acid (2), 命名为agasursacid A和agasursacid B。对分离得到的部分化合物测定了抗柯萨奇病毒B3型(CVB3)活性, 化合物3、4、6、8对柯萨奇病毒B3型有抑制活性, IC50值分别为4.77、1.59、11.11、25.87 μmol·L-1。

, authors=null, authorsList=任雅婷, 李蓓, 马洁, 李玉环, 臧应达, 李创军, 张东明, authorCompany=null, correspAuthors=李创军, 张东明, authorNote=null, correspAuthorsNote=
*李创军, Tel: 86-10-63165702, E-mail: ;
张东明, Tel: 86-10-63165227, E-mail:
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Herbal textual research on huoxiang in famous classical formulas[J]. Chin J Exp Tradit Med Form (中国实验方剂学杂志), 2023, 29: 1-13., articleTitle=Herbal textual research on huoxiang in famous classical formulas, refAbstract=null), Reference(id=1199640573595447603, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198628610824302964, doi=10.3390/antiox8030075, pmid=null, pmcid=null, year=2019, volume=8, issue=null, pageStart=75, pageEnd=null, url=null, language=null, rfNumber=[2], rfOrder=1, authorNames=null, journalName=Antioxidants (Basel), refType=null, unstructuredReference=Park CH, Yeo HJ, Baskar TB, et al. In vitro antioxidant and antimicrobial properties of flower, leaf, and stem extracts of Korean mint[J]. 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No.δCδH
1a2b1a2b
144.243.62.07 (dd, 12.5, 4.1)1.74 (m)
1.87 (t, 11.9)1.37 (m)
269.770.14.12 (m)3.68 (dt, 11.6, 4.3)
376.877.04.68 (d, 3.4)4.15 (d, 3.5)
4153.3152.4--
545.645.92.64 (m)2.20 (m)
621.021.41.48 (m)1.47 (m)
1.41 (m)
732.232.81.53 (m)1.63 (m)
1.33 (m)1.40 (m)
840.440.9--
945.746.31.92 (m)1.82 (m)
1038.338.7--
1124.725.21.99 (m)2.10 (dt, 18.4, 5.2)
1.99 (m)
12126.0127.35.50 (br s)5.30 (t, 3.7)
13139.8139.8--
1443.043.4--
1528.729.12.33 (dt, 13.3, 4.7)1.97 (m)
1.18c
1625.125.32.11 (m)2.26 (m)
1.77 (m)
1748.449.2c--
1854.056.72.64 (m)2.27 (m)
1939.738.51.44 (m)2.41 (m)
2039.7154.51.04 (m)-
2131.333.31.44 (m)2.23 (m)
1.37 (m)2.35 (td, 13.7, 4.6)
2237.740.41.96 (m)1.85 (m)
1.63 (m)
23109.8110.95.14 (br s)5.03 (br s)
4.76 (br s)4.69 (m)
2514.714.60.80 (s)0.79 (s)
2617.717.91.09 (s)0.90 (s)
2724.024.01.15 (s)1.22 (s)
28180.2180.8--
2917.816.81.00 (d, 6.4)1.02 (d, 6.5)
3021.6105.30.95 (d, 6.3)4.69 (m)
4.64 (br s)
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NMR spectral data of compounds 1 and 2. a: 1H NMR (500 MHz in pyridine-d5) and 13C NMR (125 MHz in pyridine-d5); b: 1H NMR (600 MHz in CD3OD) and 13C NMR (100 MHz in CD3OD); c: Overlapped

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No.δCδH
1a2b1a2b
144.243.62.07 (dd, 12.5, 4.1)1.74 (m)
1.87 (t, 11.9)1.37 (m)
269.770.14.12 (m)3.68 (dt, 11.6, 4.3)
376.877.04.68 (d, 3.4)4.15 (d, 3.5)
4153.3152.4--
545.645.92.64 (m)2.20 (m)
621.021.41.48 (m)1.47 (m)
1.41 (m)
732.232.81.53 (m)1.63 (m)
1.33 (m)1.40 (m)
840.440.9--
945.746.31.92 (m)1.82 (m)
1038.338.7--
1124.725.21.99 (m)2.10 (dt, 18.4, 5.2)
1.99 (m)
12126.0127.35.50 (br s)5.30 (t, 3.7)
13139.8139.8--
1443.043.4--
1528.729.12.33 (dt, 13.3, 4.7)1.97 (m)
1.18c
1625.125.32.11 (m)2.26 (m)
1.77 (m)
1748.449.2c--
1854.056.72.64 (m)2.27 (m)
1939.738.51.44 (m)2.41 (m)
2039.7154.51.04 (m)-
2131.333.31.44 (m)2.23 (m)
1.37 (m)2.35 (td, 13.7, 4.6)
2237.740.41.96 (m)1.85 (m)
1.63 (m)
23109.8110.95.14 (br s)5.03 (br s)
4.76 (br s)4.69 (m)
2514.714.60.80 (s)0.79 (s)
2617.717.91.09 (s)0.90 (s)
2724.024.01.15 (s)1.22 (s)
28180.2180.8--
2917.816.81.00 (d, 6.4)1.02 (d, 6.5)
3021.6105.30.95 (d, 6.3)4.69 (m)
4.64 (br s)
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Compd.IC50/μmol·L-1SI
34.779.0
41.5921.0
611.114.3
825.872.7
), ArticleFig(id=1199640571506684194, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198628610824302964, language=CN, label=Table 2, caption=

Antiviral activity against Coxsackie virus B3 for compounds 3, 4, 6, 8

, figureFileSmall=null, figureFileBig=null, tableContent=
Compd.IC50/μmol·L-1SI
34.779.0
41.5921.0
611.114.3
825.872.7
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藿香中的两个新乌苏烷型三萜
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任雅婷 1 , 李蓓 1 , 马洁 1 , 李玉环 2 , 臧应达 1 , 李创军 1, * , 张东明 1, *
药学学报 | 研究论文 2023,58(6): 1650-1654
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药学学报 |研究论文 2023 , 58 (6) : 1650 -1654
藿香中的两个新乌苏烷型三萜
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任雅婷1, 李蓓1, 马洁1, 李玉环2, 臧应达1, 李创军1, * , 张东明1, *
作者信息
  • 1.中国医学科学院、北京协和医学院药物研究所, 天然药物活性物质与功能国家重点实验室, 北京 100050
  • 2.中国医学科学院、北京协和医学院医药生物技术研究所, 北京 100050
通讯作者:
*李创军, Tel: 86-10-63165702, E-mail: ;
张东明, Tel: 86-10-63165227, E-mail:
Two new ursane triterpenoids from Agastache rugosa (Fisch. et.Mey.) O. Kuntze
Ya-ting REN1, Bei LI1, Jie MA1, Yu-huan LI2, Ying-da ZANG1, Chuang-jun LI1, * , Dong-ming ZHANG1, *
Affiliations
  • 1. State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
  • 2. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
出版时间: 2023-06-12 doi: 10.16438/j.0513-4870.2023-0067
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摘要
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采用硅胶、MCI、ODS柱色谱和高效制备液相色谱等方法, 从藿香80%乙醇提取物中分离得到2个新乌苏烷型三萜和12个已知化合物。通过质谱、核磁共振和ECD等波谱学方法鉴定新化合物的结构分别为2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13)-dien-28-oic acid (1)和2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13), 20(30)-trien-28-oic acid (2), 命名为agasursacid A和agasursacid B。对分离得到的部分化合物测定了抗柯萨奇病毒B3型(CVB3)活性, 化合物3、4、6、8对柯萨奇病毒B3型有抑制活性, IC50值分别为4.77、1.59、11.11、25.87 μmol·L-1。

藿香  /  化学成分  /  乌苏烷型三萜  /  抗柯萨奇病毒B3型

Two new ursane triterpenoids along with twelve known compounds were isolated from 80% ethanol extract of Agastache rugosa (Fisch. et. Mey.) O. Kuntze by using silica gel column, MCI column, ODS column and HPLC. The structures of the new compounds were identified as 2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13)-dien-28-oic acid (1) and 2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13), 20(30) -trien-28-oic acid (2) by HR-ESI-MS, NMR and ECD spectral data, named agasursacid A and agasursacid B. In addition, compounds 3, 4, 6, 8 showed anti-coxsackievirus B3 (CVB3) activities with a IC50 as 4.77, 1.59, 11.11 and 25.87 μmol·L-1, resepectively.

Agastache rugosa (Fisch.et.Mey.) O.Kuntze  /  chemical composition  /  ursane triterpenoid  /  anti-coxsackievirus B3 (CVB3) activities
任雅婷, 李蓓, 马洁, 李玉环, 臧应达, 李创军, 张东明. 藿香中的两个新乌苏烷型三萜. 药学学报, 2023 , 58 (6) : 1650 -1654 . DOI: 10.16438/j.0513-4870.2023-0067
Ya-ting REN, Bei LI, Jie MA, Yu-huan LI, Ying-da ZANG, Chuang-jun LI, Dong-ming ZHANG. Two new ursane triterpenoids from Agastache rugosa (Fisch. et.Mey.) O. Kuntze[J]. Acta Pharmaceutica Sinica, 2023 , 58 (6) : 1650 -1654 . DOI: 10.16438/j.0513-4870.2023-0067
正文
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藿香(Agastache rugosa (Fisch. et. Mey.) O. Kuntze)又称为排香草、大叶薄荷等。为唇形科藿香属多年生草本植物, 主产于我国四川、江苏、浙江、安徽等地, 在韩国及日本也有种植。藿香可作香料、景观植物, 亦可药食兼用, 其全草入药, 主治中暑发热、外感风寒、胸闷腹胀、食欲不振等, 古代经典名方藿朴夏苓汤[1]中所用“杜藿香”即为产于江浙、去除根及老茎的生品藿香。现代研究证明, 藿香提取物具有多种活性, 如抗氧化[2]、抗炎[3]、抗病毒[4]、促进肠胃运动[5]等。藿香是常用芳香化湿药, 对其挥发油部分的成分分析和活性研究报道较多, 但是对于非挥发性成分的研究较少。因此, 本课题对藿香非挥发性成分展开研究, 从藿香80%乙醇提取物中分离得到2个新乌苏烷型三萜类化合物2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13)-dien-28-oic acid (1)和2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13), 20(30)-trien-28-oic acid (2)(图 1)、3个已知黄酮类化合物(3~5)、9个已知三萜类化合物(6~14)。其中, 化合物6、7、9、10、12首次由唇形科首次分离得到, 化合物8、11、13、14首次由藿香属分离得到。对部分化合物进行了抗柯萨奇病毒B3型(CVB3)活性筛选, 结果显示, 化合物3、4、6、8对CVB3有抑制活性。
结果与讨论
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1 结构鉴定
化合物1, 白色无定形粉末, $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ +11 (c 0.10, MeOH), 通过HR-ESI-MS m/z 479.312 0 [M+Na]+ (C29H44O4Na计算值479.313 2)分析, 确定其分子式为C29H44O4, 不饱和度为8。化合物1的红外光谱显示了羟基(3 374 cm-1)、羰基(1 687 cm-1)、甲基(2 972, 2 870, 1 454, 1 378 cm-1)的特征吸收。化合物1的1H NMR (pyridine-d5, 500 MHz, 表 1)显示了3个烯键氢信号δH 5.50 (1H, br s, H-12)、5.14 (1H, br s, H-23)、4.76 (1H, br s, H-23), 5个甲基信号δH 0.80 (3H, s, H-25)、1.09 (3H, s, H-26)、1.15 (3H, s, H-27)、1.00 (3H, d, J = 6.4 Hz, H-29)、0.95 (3H, d, J = 6.3 Hz, H-30)。化合物1的13C NMR (pyridine-d5, 125 MHz)显示了29个碳信号, 包括一个羧基碳信号δC 180.2 (C-28), 两对双键碳信号δC 153.3 (C-4)、109.8 (C-23)、126.0 (C-12)、139.8 (C-13), 5个甲基信号δC 14.7 (C-25)、17.7 (C-26)、24.0 (C-27)、17.8 (C-29)、21.6 (C-30)。通过2D NMR实验进一步确定了化合物1的平面结构, 化合物1的1H-1H COSY谱图中H-1/H-2/H-3、H-5/H-6/H-7、H-11/H-12、H-15/H-16、H-18/H-19/H-29、H-20/H-21/H-22以及H-20/H-30相关, 确定结构中C(1)-C(2)-C(3)、C(5)-C(6)-C(7)、C(11)-C(12)、C(15)-C(16)、C(18)-C(19)-C(29)和C(22)-C(21)-C(20)-C(30)6个片段(图 2)。利用化合物1的HSQC和HMBC谱对上述结构片段连接, 在HMBC谱中, H-1与C-2/C-3/C-5/C-10/C-25相关、H-3与C-2/C-4/C-5/C-23、H-23与C-3/C-4/C-5、H-7与C-8、H-11与C-9、H-12与C-9/C-14/C-18、H-15与C-14/C-17、H-15/H-18/H-22与C-16、H-19/H-29与C-18、H-30与C-20相关(图 2), 确定了化合物1的乌苏烷母核和平面结构。化合物1的平面结构与Ilekudinol B[6]一致, 化合物1与ilekudinol B的主要区别是H-3的偶合常数不同, 推测两者的主要区别是C-2与C-3位羟基相对构型不同。在化合物1的NOESY谱图中, H-2与H-1/H-3/H-25、H-3与H-2/H-23/H-25相关(图 2), 结合H-3的偶合常数(J = 3.4 Hz)表明化合物1的C-2和C-3羟基的相对构型为2α, 3α, 确定化合物1的结构为2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13)-dien-28-oic acid。通过实验ECD及计算ECD确定了化合物1的绝对构型, 采用ECD计算方法[B3LYP/6-311G(2d, p), MeOH] 计算了1a (2R, 3S, 8R, 10R, 14S, 17S, 18S, 19S, 20R)和1b (2S, 3R, 8S, 10S, 14R, 17R, 18R, 19R, 20S)的ECD谱, 化合物1的实验ECD与1a的计算ECD匹配较好(图 3), 因此, 确定化合物1的绝对构型为2R, 3S, 8R, 10R, 14S, 17S, 18S, 19S, 20R, 命名为agasursacid A。
化合物2, 白色无定形粉末, $ {\left[\alpha \right]}_{\mathrm{D}}^{20.6} $ +149 (c 0.10, MeOH), 通过HR-ESI-MS m/z 477.297 5 [M+Na]+ (C29H42O4Na计算值477.298 7)分析, 确定其分子式为C29H42O4, 不饱和度为9。化合物2的红外光谱显示了羟基(3 384 cm-1)、羧基(1 697 cm-1)、双键(1 648 cm-1)、甲基(2 932, 1 453, 1 386 cm-1)的特征吸收。化合物2的1H NMR (CD3OD, 600 MHz, 表 1)谱显示了5个烯键氢信号δH 5.30 (1H, t, J = 3.7 Hz, H-12)、5.03 (1H, br s, H-23)、4.69 (2H, m, H-23, 30)、4.64 (1H, br s, H-30), 4个甲基信号δH 0.79 (3H, s, H-25)、0.90 (3H, s, H-26)、1.22 (3H, s, H-27)、1.02 (3H, d, J = 6.5 Hz, H-29)。化合物2的13C NMR (CD3OD, 100 MHz)也显示了29个碳信号, 包括羧基、双键和甲基等特征信号。以上数据表明化合物2也是一个降碳乌苏烷型三萜, 其波谱数据与patrinolide C[7]相似, 主要区别是化合物2在C-2位多1个羟基取代。进一步通过化合物2的1H-1H COSY谱图中H-1/H-2/H-3相关, 以及HMBC谱中H-1与C-2/C-3/C-25、H-2与C-1/C-3、H-3与C-2/C-4/C-5/C-23的相关, 确定2个羟基分别位于C-2位及C-3位(图 2)。根据H-3位(δH 4.15)偶合常数为3.5 Hz推断羟基的相对构型为2α, 3α[8]。观察化合物2的NOESY谱图, 发现H-2与H-1/H-3/H-25相关、H-3与H-2/H-23/H-25相关(图 2), 进一步表明C-2位、C-3位羟基的相对构型为2α, 3α。因此, 化合物2的结构确定为2α, 3α-dihydroxy-24-nor-urs-4(23), 12(13), 20(30)-trien-28-oic acid。通过实验ECD及计算ECD进一步确定了化合物2的绝对构型, 对2a (2R, 3S, 8R, 10R, 14S, 17S, 18S, 19S)和2b (2S, 3R, 8S, 10S, 14R, 17R, 18R, 19R)进行ECD计算[B3LYP/6-311G(2d, p), MeOH], 化合物2的实验ECD与2a的计算ECD匹配较好(图 3), 因此, 确定化合物2的绝对构型为2R, 3S, 8R, 10R, 14S, 17S, 18S, 19S, 命名为agasursacid B。
通过谱学数据与文献对照, 确定12个已知化合物分别为滨蓟黄素(3)[9]、刺槐素(4)[9]、香叶木素(5)[9]、2α, 3β-二羟基-23-去甲-4(24)-12-二烯-齐墩果酸(6)[10]、2α, 3α-二羟基熊果酸(7)[10]、2α, 3α-dihydroxy-24-nor-4(23), 12-oleanadien-28-oic acid (8)[11]、2α, 3β-dihydrox-yolean-13(18)-en-28-oic acid (9)[12]、psiguanins A (10)[13]、2α, 3α-2, 3-dihydroxyursa-12, 20(30)-dien-28-oic acid (11)[14]、3β-acetoxy-olean-11, 13(18)-dien-28-oic acid (12)[15]、3β-acetoxyurs-11-en-28, 13-olide (13)[16]、3β-O-乙酰熊果酸(14)[17]。其中, 化合物6、7、9、10、12首次由唇形科首次分离得到, 化合物8、11、13、14首次由藿香属分离得到。
2 化合物活性检测
对化合物3、4、6、8、9、11测定了其抗柯萨奇病毒B3型(CVB3)活性, 结果显示: 化合物3、4、6、8对柯萨奇病毒B3型有抑制活性, IC50值分别为4.77、1.59、11.11、25.87 μmol·L-1, 化合物相应SI值为2.7~21.0 (表 2), 阳性对照药利巴韦林IC50值为95.45 μmol·L-1, SI值为16.3。
实验部分
收起
紫外可见分光光度仪(JASCO V-650型, 日本); 旋光测定仪(Rhdolph Autopol V型, 美国); 红外光谱仪(Thermo Nicolet 57000型, 美国); 高分辨质谱仪(Themo Q Exactive Focus组合型四级杆Orbitrap质谱仪, 美国); 核磁共振波谱仪(Bruker AVANCE-Ⅲ 400 MHz, 德国; 中科牛津WNMR-I 500 MHz, 中国; Bruker AVANCE-Ⅲ HD 600 MHz, 德国); 圆二色谱测定仪(JASCO J-815型, 日本); 高效液相色谱仪(Aglient1100)(安捷伦科技有限公司, 美国); 制备液相色谱仪(LC-6AD, 日本岛津公司); 中压制备液相色谱系统(Büchi Gradient Former B-687, RP C18, 瑞士); 硅胶柱色谱填料和薄层色谱用硅胶GF254 (100~200目, 200~300目, 青岛海洋化工有限公司); MCI柱色谱填料(CHP20/P120, 日本三菱化学公司); ODS柱色谱填料(YMC-ODS C18 50 μm, 日本); 薄层显色(10%硫酸乙醇溶液显色)。
药材于2020年7月采摘自安徽省亳州市涡阳县, 经上海中医药大学侴桂新研究员鉴定为藿香(Agastache rugosa (Fisch. et Mey.) O. Ktze)。标本储存在中国医学科学院药物研究所标本室(ID-25092)。
1 提取与分离
藿香全草30 kg经粉碎后, 用80%乙醇加热回流提取两次, 两次提取液合并后减压浓缩, 浓缩液经乙酸乙酯重复萃取3次, 乙酸乙酯层合并后减压浓缩蒸干, 得到乙酸乙酯部位浸膏(409.8 g)。浸膏用硅胶拌样并装柱, 采用石油醚∶乙酸乙酯= 5∶1~2∶1, 石油醚∶乙酸乙酯∶甲醇= 11∶4∶1, 95%乙醇作为流动相洗脱得到41个组分: A1~A41。其中的A28~A34 (29 g)经MCI柱以40%甲醇(2 L)、50%甲醇(2 L)、60%甲醇(2 L)、70%甲醇(4 L)、80%甲醇(4 L)、90%甲醇(2 L)洗脱及甲醇冲柱得到B1~B28; 选择B18~B23 (4.9 g)经中压液相色谱以60%~100%甲醇-水进行梯度洗脱, 得到M1~M48; M8经40%乙腈-水纯化(ODS制备柱, 8 mL·min-1)得到化合物3 (35.12 mg); M18经55%乙腈-水纯化(ODS制备柱, 8 mL·min-1)得到化合物4 (16.33 mg); M21经55%乙腈-水分离(ODS制备柱, 8 mL·min-1), 70%甲醇-水纯化(ODS半制备柱, 4 mL·min-1)得到化合物1 (4.67 mg)和化合物8 (5.10 mg); M19经55%乙腈-水分离(ODS制备柱, 8 mL·min-1), 70%甲醇-水纯化(ODS半制备柱, 4 mL·min-1)得到化合物2 (4.08 mg); M25经55%乙腈-水分离(ODS制备柱, 8 mL·min-1), 得到化合物6 (25.16 mg)和M25-4, M25-4再经52.5%乙腈-水纯化(ODS半制备柱, 8 mL·min-1), 得到化合物11 (4.58 mg); M27经62.5%乙腈-水分离(ODS制备柱, 8 mL·min-1), 得到M27-4、M27-5, M27-4经75%甲醇-水纯化(ODS半制备柱, 4 mL·min-1)得到化合物9 (4.14 mg), M27-5经80%甲醇-水纯化(ODS半制备柱, 4 mL·min-1)得到化合物7 (42.99 mg)、10 (8.72 mg)。A3~A6 (37.6 g)经MCI柱以70%甲醇(3 L)、80%甲醇(4 L)、90%甲醇(4 L)、甲醇(4 L)洗脱及甲醇∶二氯甲烷= 1∶1 (2 L)冲柱得到3B1~3B28; 选择3B24~3B28 (8.9 g)经硅胶柱以石油醚∶二氯甲烷= 1∶1 (2 L)、石油醚∶二氯甲烷= 1∶2 (2 L)、甲醇(1 L)进行洗脱得到BG1~BG26; BG6~BG9合并(1.2 g)经开放ODS柱以80%~100%甲醇-水进行梯度洗脱, 得到BG6-1~BG6-15; BG6-12经95%乙腈-水纯化(ODS半制备柱, 4 mL·min-1)得到化合物12 (2.58 mg); BG18经92.5%乙腈-水分离(ODS制备柱, 8 mL·min-1), 得到化合物14 (281.13 mg), 93%甲醇-水纯化(ODS半制备柱, 4 mL·min-1)得到化合物13 (13.44 mg)。A35~38 (102.0 g)经MCI柱以20%甲醇(4 L)、40%甲醇(4 L)、50%甲醇(2 L)、60%甲醇(6 L)、70%甲醇(8 L)、80%甲醇(10 L)、90%甲醇(8 L)、94%甲醇(4 L)及甲醇冲柱, 得到C1~C38, 选择C20~C21 (3.5 g)经开放ODS柱以50%~100%乙腈进行梯度洗脱, 得到CO1~CO40; CO6经60%~90%甲醇-水分离(ODS制备柱, 8 mL·min-1)得到CO6-4, 再经85%甲醇-水纯化(纤维素-4手性半制备柱, 4 mL·min-1)得到化合物5。
2 结构鉴定
化合物1    白色无定形粉末, $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ +11 (c 0.10, MeOH); UV (MeOH) λmax (log ε)/nm: 203 (6.54); CD (MeOH): Δε224.5 nm -1.76; IR/cm-1: 3 374、1 687、2 972、2 870、1 454、1 378; 1H NMR (pyridine-d5, 500 MHz)、13C NMR (pyridine-d5, 125 MHz)数据见表 1; (+)-(HR-ESI-MS: m/z 479.312 0 [M+Na]+ (C29H44O4Na计算值479.313 2)。
化合物2    白色无定形粉末, $ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ +149 (c 0.10, MeOH); UV (MeOH) λmax (log ε)/nm: 204 (4.02); CD (MeOH): Δε200 nm +23.6; IR/cm-1: 3 384、1 697、1 648、2 932、1 453、1 386; 1H NMR (CD3OD, 600 MHz)、13C NMR (CD3OD, 100 MHz)数据见表 1; (+)-(HR-ESI-MS: m/z 477.297 5 [M+Na]+ (C29H42O4Na计算值477.298 7)。
3 ECD计算
化合物三维结构采用Chem3D 19.0获取, 用分子力学方法在MM2力场下进行粗略优化; 使用Conflex 8B进行构象搜索; 采用Gaussian16, 在导体极化连续模型(CPCM)中, MeOH为溶剂, 以时间依赖密度泛函理论(TDDFT)方法在B3LYP/6-311G(2d, p)水平对主要构象进行计算优化, 在计算优化的构象基础上采用相同的基组与方法计算谱学性质; 采用SpecDis 1.70.1软件根据玻尔兹曼分布加权拟合出ECD谱图。
4 抗柯萨奇病毒B3型活性测定
以Vero (非洲绿猴肾)细胞为病毒宿主, 利巴韦林为阳性对照药, 采用细胞病变效应法(cytopathic effect, CPE)评价。Vero细胞种96孔培养板, 24 h后感染柯萨奇病毒B3型10-5, 吸附2 h, 弃病毒液, 加入含有不同稀释度样品及阳性对照药的维持液, 同时设细胞对照孔和病毒对照孔, 5% CO2、37 ℃培养。待病毒对照组CPE达4+时观察各组细胞CPE, 用Reed-Muench法分别计算样品对细胞的半数有毒浓度(TC50)和对病毒的半数抑制浓度(IC50)。
作者贡献: 任雅婷是本文的第一作者, 负责成分分离、结构鉴定和论文撰写; 李蓓、马洁、臧应达协助提取分离工作; 李玉环进行化合物抗柯萨奇病毒B3型活性的测定; 李创军和张东明是本文的通讯作者, 设计和组织了整个研究, 并对论文进行了修改。
利益冲突: 所有作者声明不存在任何利益冲突。
基金
收起
  • 国家重点研发计划资助项目(2019YFC1711000)
  • 中国医学科学院创新工程资助项目(2021-I2M-1-028)
文献
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2023年第58卷第6期
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doi: 10.16438/j.0513-4870.2023-0067
  • 接收时间：2023-01-27
  • 首发时间：2025-11-21
  • 出版时间：2023-06-12
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  • 收稿日期：2023-01-27
  • 修回日期：2023-02-20
基金
国家重点研发计划资助项目(2019YFC1711000)
中国医学科学院创新工程资助项目(2021-I2M-1-028)
作者信息
    1.中国医学科学院、北京协和医学院药物研究所, 天然药物活性物质与功能国家重点实验室, 北京 100050
    2.中国医学科学院、北京协和医学院医药生物技术研究所, 北京 100050

通讯作者:

*李创军, Tel: 86-10-63165702, E-mail: ;
张东明, Tel: 86-10-63165227, E-mail:
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2种不同金属材料的力学参数
科
Family		 属数
Number of
genus		 种数
Number of
species		 占总种数比例
Percentage of
total species (%)		 属
Genus		 种数
Number of
species		 占总种数比例
Percentage of total
species (%)
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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