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Article(id=1308841258823545634, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841198224240856, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2026-0142, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1769961600000, receivedDateStr=2026-02-02, revisedDate=1775145600000, revisedDateStr=2026-04-03, acceptedDate=null, acceptedDateStr=null, onlineDate=1789981673197, onlineDateStr=2026-09-21, pubDate=1781193600000, pubDateStr=2026-06-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789981673197, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789981673197, creator=13701087609, updateTime=1789981673197, updator=13701087609, issue=Issue{id=1308841198224240856, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='6', pageStart='1881', pageEnd='2376', issueExtLink='null', onlineDate='null', pubDate='1781193600000', pubDateStr='2026-06-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981658750, creator='13701087609', updateTime=1789984187230, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851803500933401, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841198224240856, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851803500933402, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841198224240856, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=2241, endPage=2244, ext={EN=ArticleExt(id=1308841259104564003, articleId=1308841258823545634, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Two new cyclic dipeptides with hydroxyisobutyl side chains from Angelica dahurica, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Using various separation and purification techniques including silica gel and recrystallization, two new cyclic dipeptides involving non-proteinogenic amino acids were first isolated and purified from the ethyl acetate fraction of the ethanol (95%) extract of Angelica dahurica. Through the modern spectroscopic methods such as NMR, HR-ESI-MS, IR, OR, UV, and CD, their structures were identified as angelidaphine A (1) and angelidaphine B (2).

, authors=Chun-xia XIAO1, Fan-lin TANG1, Jin-ke LI1, Xiao-xue SUN1, Feng ZHANG1, 2, *, Bao-shun ZHANG1, *, authorsList=Chun-xia XIAO, Fan-lin TANG, Jin-ke LI, Xiao-xue SUN, Feng ZHANG, Bao-shun ZHANG, authorCompany=null, correspAuthors=Feng ZHANG, Bao-shun ZHANG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2026 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=1308841261738586926, articleId=1308841258823545634, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=白芷中两个具有羟基异丁基侧链的新环二肽类化合物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用硅胶柱层析、重结晶等多种分离纯化技术, 对白芷(Angelica dahurica) 95%乙醇提取物的乙酸乙酯部位进行分离纯化, 首次从白芷中分离得到两个新的非蛋白氨基酸组成的环二肽。运用NMR、HR-ESI-MS、IR、OR、UV、CD等现代波谱手段, 结构分别鉴定为angelidaphine A (1) 和angelidaphine B (2)。

, authors=肖春霞1, 唐凡淋1, 李金科1, 孙孝雪1, 张锋1, 2, *, 张保顺1, *, authorsList=肖春霞, 唐凡淋, 李金科, 孙孝雪, 张锋, 张保顺, authorCompany=null, correspAuthors=张锋, 张保顺, authorNote=

作者贡献:

肖春霞负责实验实施、数据分析处理以及论文撰写; 唐凡淋负责实验实施; 李金科参与实验实施; 孙孝雪参与实验实施; 张锋负责实验指导及稿件的修改; 张保顺负责实验设计、文章的审阅和提出论文写作的建议。

, correspAuthorsNote=
张锋, E-mail:
张保顺, E-mail:
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No.12
δHδCδHδC
2177.48169.40
34.68 (1H, d, J = 12.1 Hz)58.96160.28
5173.10173.51
64.50 (1H, dd, J = 8.9, 3.3 Hz)64.885.20 (1H, dd, J = 9.0, 5.0 Hz)64.57
71.98 (1H, ddd, J = 12.1, 9.7, 6.4 Hz)42.84121.84
84.20 (1H, dq, J = 9.8, 6.1 Hz)80.274.99 (1H, m)79.07
91.38 (3H, t, J = 6.9 Hz)17.031.45 (3H, d, J = 6.8 Hz)17.90
10a2.46 (1H, m)22.732.56 (1H, m)22.48
10b2.06 (1H, m)2.00 (1H, m)
112.40 (2H, m)28.462.50 (2H, m)29.30
12206.75204.62
132.25 (3H, s)25.032.19 (3H, s)26.50
7-CH31.14 (3H, d, J = 6.4 Hz)12.492.10 (3H, s)13.15
), ArticleFig(id=1308841266624951141, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841258823545634, language=CN, label=Tab.1, caption=

The 1H NMR (400 MHz) and 13C NMR (100 MHz) data of compound 1 (in CD3OD), and 2 (in CDCl3)

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No.12
δHδCδHδC
2177.48169.40
34.68 (1H, d, J = 12.1 Hz)58.96160.28
5173.10173.51
64.50 (1H, dd, J = 8.9, 3.3 Hz)64.885.20 (1H, dd, J = 9.0, 5.0 Hz)64.57
71.98 (1H, ddd, J = 12.1, 9.7, 6.4 Hz)42.84121.84
84.20 (1H, dq, J = 9.8, 6.1 Hz)80.274.99 (1H, m)79.07
91.38 (3H, t, J = 6.9 Hz)17.031.45 (3H, d, J = 6.8 Hz)17.90
10a2.46 (1H, m)22.732.56 (1H, m)22.48
10b2.06 (1H, m)2.00 (1H, m)
112.40 (2H, m)28.462.50 (2H, m)29.30
12206.75204.62
132.25 (3H, s)25.032.19 (3H, s)26.50
7-CH31.14 (3H, d, J = 6.4 Hz)12.492.10 (3H, s)13.15
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白芷中两个具有羟基异丁基侧链的新环二肽类化合物
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肖春霞 1 , 唐凡淋 1 , 李金科 1 , 孙孝雪 1 , 张锋 1, 2, * , 张保顺 1, *
药学学报 | 研究论文 2026,61(6): 2241-2244
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药学学报 |研究论文 2026 , 61 (6) : 2241 -2244
白芷中两个具有羟基异丁基侧链的新环二肽类化合物
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肖春霞1, 唐凡淋1, 李金科1, 孙孝雪1, 张锋1, 2, * , 张保顺1, *
作者信息
  • 1西南大学药学院 中医药学院, 重庆 400715
  • 2江苏省中医院重庆医院, 重庆 402105
通讯作者:
张锋, E-mail:
张保顺, E-mail:
作者简介:

作者贡献:

肖春霞负责实验实施、数据分析处理以及论文撰写; 唐凡淋负责实验实施; 李金科参与实验实施; 孙孝雪参与实验实施; 张锋负责实验指导及稿件的修改; 张保顺负责实验设计、文章的审阅和提出论文写作的建议。

Two new cyclic dipeptides with hydroxyisobutyl side chains from Angelica dahurica
Chun-xia XIAO1, Fan-lin TANG1, Jin-ke LI1, Xiao-xue SUN1, Feng ZHANG1, 2, * , Bao-shun ZHANG1, *
Affiliations
  • 1College of Pharmaceutical Sciences, Southwest University, Chongqing 400715, China
  • 2Jiangsu Province Hospital of Chinese Medicine Chongqing Hospital, Chongqing 402105, China
出版时间: 2026-06-12 doi: 10.16438/j.0513-4870.2026-0142
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利用硅胶柱层析、重结晶等多种分离纯化技术, 对白芷(Angelica dahurica) 95%乙醇提取物的乙酸乙酯部位进行分离纯化, 首次从白芷中分离得到两个新的非蛋白氨基酸组成的环二肽。运用NMR、HR-ESI-MS、IR、OR、UV、CD等现代波谱手段, 结构分别鉴定为angelidaphine A (1) 和angelidaphine B (2)。

白芷  /  化学成分  /  环二肽

Using various separation and purification techniques including silica gel and recrystallization, two new cyclic dipeptides involving non-proteinogenic amino acids were first isolated and purified from the ethyl acetate fraction of the ethanol (95%) extract of Angelica dahurica. Through the modern spectroscopic methods such as NMR, HR-ESI-MS, IR, OR, UV, and CD, their structures were identified as angelidaphine A (1) and angelidaphine B (2).

Angelica dahurica  /  chemical composition  /  cyclic dipeptide
肖春霞, 唐凡淋, 李金科, 孙孝雪, 张锋, 张保顺. 白芷中两个具有羟基异丁基侧链的新环二肽类化合物. 药学学报, 2026 , 61 (6) : 2241 -2244 . DOI: 10.16438/j.0513-4870.2026-0142
Chun-xia XIAO, Fan-lin TANG, Jin-ke LI, Xiao-xue SUN, Feng ZHANG, Bao-shun ZHANG. Two new cyclic dipeptides with hydroxyisobutyl side chains from Angelica dahurica[J]. Acta Pharmaceutica Sinica, 2026 , 61 (6) : 2241 -2244 . DOI: 10.16438/j.0513-4870.2026-0142
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白芷(Angelicae dahurica) 为伞形科植物白芷Angelica dahurica (Fisch. ex Hoffm.) Benth. et Hook. f的干燥根, 主要分布于我国东北、华北地区[1]。白芷味辛, 性温, 具有解表散寒、祛风止痛、宣通鼻窍、燥湿止带、消肿排脓的功效, 临床常用于治疗感冒头痛、眉棱骨痛、鼻塞流涕、疮疡肿痛等病症[2-4]。化学成分研究表明, 白芷富含香豆素、生物碱、挥发油、多糖类化合物[5]。现代药理学研究揭示, 白芷具有抗炎、抗肿瘤、抗菌、镇痛、抗氧化等活性[6-10]。为进一步探索白芷中的化学成分, 并寻找新颖的天然产物, 研究其药效物质基础, 本实验对白芷化学成分进行了分离纯化及结构鉴定, 从乙酸乙酯部位得到2个新的环二肽(图1)。
结果与讨论
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化合物1为白色针晶, HR-ESI-MS给出准分子离子峰m/z 257.149 6 [M+H]+ (计算值为257.149 6), 结合氢谱和碳谱数据(表1), 推测其分子式为C12H20N2O4, 不饱和度为4。IR光谱显示有羟基(3 435 cm-1) 和羰基(1 771、1 688 cm-1) 吸收。1H NMR谱显示三组甲基信号2.25 (3H, s, H-13), 1.38 (3H, t, J = 6.9 Hz, H-9) 和1.14 (3H, d, J = 6.4 Hz, 7-CH3), 此外高场区还有8个质子信号。13C NMR谱中显示有12个碳信号, 其中包括3个羰基碳信号。DEPT-135数据显示有9个碳信号, 包括3个甲基信号、4个次甲基信号和2个亚甲基信号。通过分析HSQC谱图, 将12个碳信号归为酮羰基碳信号δC 177.48 (C-2)、δC 173.10 (C-5) 和δC 206.75 (C-11), 连氧次甲基信号δC 80.27 (C-8), 次甲基信号δC 58.96 (C-3)、δC 64.88 (C-6) 和δC 42.84 (C-7), 亚甲基信号δC 22.73 (C-10) 和δC 28.46 (C-11), 甲基信号δC 12.49 (7-CH3)、δC 17.03 (C-9) 和δC 25.03 (C-13)。HMBC谱中H-3 (δH 4.68) 与C-2 (δC 177.48)、C-5 (δC 173.10) 相关, 且H-6 (δH 4.50) 与C-5 (δC 173.10) 相关。以上波谱数据提示化合物1具有2, 5-哌嗪骨架结构[11]。
通过1H-1H COSY和HMBC谱进一步确认化合物1的平面结构(图2)。HMBC谱中H-3 (δH 4.68) 与C-7-CH3 (δC 12.49) 和C-7 (δC 42.84); H-8 (δH 4.20) 与C-7-CH3 (δC 12.49) 有相关信号。同时, 1H-1H COSY谱图中H-7 (δH 1.98)、H-3 (δH 4.68) 和H-8 (δH 4.20) 的相关信号, 提示存在异丁基结构且与2, 5-哌嗪骨架结构的C-3相连。此外H-7 (δH 1.98) 与C-8 (δC 80.27) 相关, H-9 (δH 1.38) 与C-8 (δC 80.27) 相关, 并且DEPT-135显示C-8为次甲基, 因此证实存在8位羟基取代的异丁基结构。结合H-10a (δH 2.46) 同时与H-6 (δH 4.50) 和H-11 (δH 2.40) 的1H-1H COSY相关, 以及H-10a (δH 2.46)、H-11 (δH 2.40)、H-13 (δH 2.25) 与C-12 (δC 206.75) 的HMBC相关, 证实了化合物1中存在12号位羰基取代的正丁基结构, 且与2, 5-哌嗪骨架结构的C-6相连。
H-7与H-3和H-8的NOESY相关(图3) 说明H-7与H-3和H-8位于同侧, H-6与H-3的NOESY相关说明H-6与H-3位于哌嗪环同侧, 由此确定了化合物1的相对构型。通过比对化合物1的实测CD谱与计算CD谱(图4), 进而确定了化合物1的绝对构型为3R, 6R, 7R, 8R。综上, 确定了化合物1的结构并将其命名为angelidaphine A。
化合物2为淡黄色针晶, HR-ESI-MS给出准分子离子峰m/z 255.134 5 [M+H]+ (计算值为255.133 9), 结合氢谱和碳谱数据(表1), 推测其分子式为C12H18N2O4, 不饱和度为5。IR光谱显示有羟基(3 501 cm-1) 和羰基(1 752、1 714、1 673 cm-1) 吸收。化合物2的核磁数据与化合物1高度相似, 主要差异体现在化合物2新增两个季碳信号δC 160.28 (C-3) 和δC 121.84 (C-7), 而化合物1中的两个次甲基C-3 (δC 58.96) 和C-7 (δC 42.84) 在化合物2中消失。此外, 在化合物2的1H NMR和1H-1H COSY中, 未观察到化合物1中H-3与H-7的相关信号(图2)。HMBC谱进一步显示, H-7-CH3 (δH 2.10) 和H-8 (δH 4.99) 均与C-3 (δC 160.28) 和C-7 (δC 121.84) 存在远程相关。结合化合物2的分子质量较化合物1减少2 Da, 因此确定化合物2为C-3和C-7位形成双键的脱氢衍生物。关键的NOESY相关信号出现在H-6与H-8之间(图3), 表明二者位于哌嗪环的同侧, 并进一步确认C-3/C-7双键为Z构型; 反之, 在E构型中, H-6与H-8的空间距离较远, 将导致该NOESY信号缺失。由此, 化合物2的相对构型得到了确定。通过比对化合物2的实测CD谱与计算CD谱(图5), 进而确定了化合物2的绝对构型为3Z, 6R, 8R。综上, 化合物2的结构得到确定, 并将其命名为angelidaphine B。
实验部分
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AVANCE III HD 400 MHz核磁共振仪(瑞士布鲁克拜厄斯宾); 半制备高效液相色谱仪(北京赛谱锐思科技有限公司); UniSil 10-120 C18色谱柱(250 mm × 10 mm; 5 μm; 纳微科技有限公司); Chirascan V100圆二色光谱仪(英国应用光物理公司); Impact Ⅱ高分辨质谱仪(德国布鲁克公司); 1200分析型高效液相色谱仪(美国安捷伦科技有限公司); RV-131旋转蒸发仪(德国艾卡仪器设备有限公司); ZF-2型三用紫外线分析仪(上海嘉鹏科技有限公司); 柱层析硅胶、薄层色谱硅胶GF254 (重庆川东化工有限公司); 常用有机试剂均购自川东化工有限公司。
白芷干燥根购买于四川养殖基地, 由擎科生物科技有限公司成都分公司对其DNA进行提取、扩增和测序, 鉴定其为伞形科白芷属白芷Angelica dahurica (Fisch. ex Hoffm.) Benth. et Hook. f的根。样本(20230425) 存放于西南大学药学院实验室。
1　提取与分离
白芷(26.7 kg) 切片粉碎后, 用95%的乙醇回流提取3次, 每次2 h。滤液合并后减压浓缩得浸膏2.79 kg。将浸膏悬浮于水中, 依次采用等体积的石油醚、乙酸乙酯、正丁醇萃取3次, 萃取液浓缩后分别得到石油醚部位(702 g), 乙酸乙酯部位(227 g), 正丁醇部位(337 g)。乙酸乙酯部位经硅胶柱色谱分离, 以二氯甲烷-甲醇(100∶0→0∶100) 进行梯度洗脱, 分段收集洗脱液, 经TLC分析合并, 得到16个组分Fr. A~Fr. I。Fr. E (7.7 g) 经硅胶柱层析分离, 以二氯甲烷-甲醇(100∶0→20∶1) 梯度洗脱, 根据TLC分析合并得到5个组分(Fr. E1~Fr. E5), 其中Fr. E5经石油醚-乙酸乙酯(10∶1→5∶1) 洗脱后, Fr. E54再通过石油醚-乙酸乙酯(5∶1) 等度洗脱后利用石油醚-乙酸乙酯混合溶剂重结晶得到化合物1 (2.1 mg), Fr. E55组分利用甲醇重结晶得到化合物2 (2.4 mg)。
2　结构鉴定
化合物1白色针晶, [α]$ {}_{\mathrm{D}}^{20} $ +45.0 (c 0.3, MeOH); UV (MeOH) λmax (log ε): 210 nm (4.56); IR (KBr) νmax: 3 435.91、2 922.53、1 711.12、1 688.73、1 447.88、666.19 cm-1; HR-ESI-MS m/z: 257.149 6 [M+H]+ (calcd. 257.149 6); 1H NMR (CD3OD, 400 MHz) 和13C NMR (CD3OD, 100 MHz) 数据如表1。
化合物2淡黄色针晶, [α]$ {}_{\mathrm{D}}^{20} $ +35.0 (c 0.3, MeOH); UV (MeOH) λmax (log ε): 210 nm (4.60)、260 nm (4.06); IR (KBr) νmax: 2 924.64、1 752.11、1 714.08、1 411.97 cm-1; HR-ESI-MS m/z: 255.134 5 [M+H]+ (calcd. 255.133 9); 1H NMR (CDCl3, 400 MHz) 和13C NMR (CDCl3, 100 MHz) 数据如表1。
3　ECD计算
化合物1和2的绝对构型均是通过计算ECD确定。利用SYBYL-X 2.0软件, 采用MMFF94s力场进行构象搜索设置能量截断值为5 kcal·mol-1。基于CPCM甲醇溶剂模型, 在B3LYP/6-31G(d) 水平上用ORCA5.0.3程序完成几何优化与频率分析, 所有构象异构体经确认均为势能面上的稳定点且无虚频。采用TDDFT方法, 在RSX-QIDH/def2-TZVP理论水平下, 采用CPCM模型计算前60个激发态的激发能、振子强度及旋转强度(速度形式)。ECD通过高斯函数叠加法模拟(半峰宽参数σ为0.30)。各构象的吉布斯自由能通过B3LYP-D3 (BJ) /6-31G水平的热力学校正与wB97M-V/def2-TZVP水平的电子能量计算获得。最终光谱由各构象的模拟光谱基于Boltzmann分布理论及其相对吉布斯自由能(ΔG) 加权平均生成。

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2026年第61卷第6期
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doi: 10.16438/j.0513-4870.2026-0142
  • 接收时间：2026-02-02
  • 首发时间：2026-09-21
  • 出版时间：2026-06-12
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  • 收稿日期：2026-02-02
  • 修回日期：2026-04-03
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    1西南大学药学院 中医药学院, 重庆 400715
    2江苏省中医院重庆医院, 重庆 402105

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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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