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Article(id=1201124483961680071, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1201124478286786612, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2023-1003, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1693152000000, receivedDateStr=2023-08-28, revisedDate=1695312000000, revisedDateStr=2023-09-22, acceptedDate=null, acceptedDateStr=null, onlineDate=1764299992789, onlineDateStr=2025-11-28, pubDate=1710172800000, pubDateStr=2024-03-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1764299992789, onlineIssueDateStr=2025-11-28, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1764299992789, creator=13701087609, updateTime=1764299992789, updator=13701087609, issue=Issue{id=1201124478286786612, tenantId=1146029695717560320, journalId=1189982191388893191, year='2024', volume='59', issue='3', pageStart='493', pageEnd='788', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1764299991434, creator=13701087609, updateTime=1764300490467, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1201126571420639892, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1201124478286786612, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1201126571420639893, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1201124478286786612, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=673, endPage=677, ext={EN=ArticleExt(id=1201124484326584543, articleId=1201124483961680071, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Two new flavonoid glycosides from Diphylleia sinensi, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Five flavonoid glycosides were isolated from the methanol and ethyl acetate fractions of the ethanol extract of Diphylleia sinensi by using various chromatographic methods, including silica gel, MCI gel, Sephadex LH-20, ODS and semi-preparative HPLC. The structures of the isolated compounds were identified as diphyflavonoid A (1), diphyflavonoid B (2), quercetin-3-O-β-D-glucopyranoside (3), kaempferol-3-O-β-D-glucopyranoside (4), kaempferol-3-O-(6″-O-acetyl)-β-D-glucopyranoside (5) by spectroscopy methods (1D NMR, 2D NMR, UV, IR, and MS). Compounds 1 and 2 were two new flavonoid glycosides, and compounds 3 and 5 were isolated from the genus Diphylleia for the first time.

, correspAuthors=Yan-jun SUN, Wei-sheng FENG, 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=Hao-jie WANG, Chen ZHAO, Yan-jun SUN, Jian-hong GONG, Hong-yun BAI, Hui CHEN, Wei-sheng FENG), CN=ArticleExt(id=1201124485303857452, articleId=1201124483961680071, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=窝儿七中2个新的黄酮苷类化合物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶、MCI、凝胶、ODS等柱色谱以及半制备液相等现代色谱分离技术对窝儿七(Diphylleia sinensi) 乙醇提取物的乙酸乙酯洗脱部位和甲醇洗脱部位的化学成分进行分离纯化, 得到5个黄酮苷类化合物。运用现代波谱学方法(1D NMR、2D NMR、UV、IR和MS) 鉴定结构, 分别为山荷叶酮苷A (1)、山荷叶酮苷B (2)、槲皮素-3-O-β-D-葡萄糖苷(3)、山柰酚-3-O-β-D-葡萄糖苷(4)、山柰酚-3-O-(6″-O-乙酰)-β-D-葡萄糖苷(5)。化合物1和2为2个新的黄酮苷类化合物, 化合物3和5为首次从山荷叶属中分离得到。

, correspAuthors=孙彦君, 冯卫生, authorNote=null, correspAuthorsNote=
*孙彦君, Tel: 86-371-65962746, E-mail: ;
冯卫生, E-mail:
, copyrightStatement=版权所有©《药学学报》编辑部2024, copyrightOwner=null, extLink=null, articleAbsUrl=null, sourceXml=sYGbIhpTHV4Vi3QE45+xrQ==, magXml=gCznz4DYgb20gTJkJ5iNPA==, pdfUrl=null, pdf=iob46ugCBEQ40Nf+JWisAQ==, pdfFileSize=759346, pdfExtLink=null, richHtmlUrl=null, mobilePdfUrl=null, reviewReport=null, pdfFirstPage=null, abstractGraph=viXYVZfn1qhaSkPzzTwgWg==, abstractGraphContent=null, abstractVideo=null, citation=null, cebUrl=null, magXmlContent=cRy2iIJdhDhWLkq/k3LPOA==, mapNumber=null, authorCompany=null, fund=null, authors=null, authorsList=王浩杰, 赵晨, 孙彦君, 弓建红, 白红云, 陈辉, 冯卫生)}, authors=[Author(id=1201124487405203852, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1201124483961680071, orderNo=0, firstName=null, middleName=null, lastName=null, nameCn=null, orcid=null, stid=null, country=null, authorPic=null, dead=0, email=null, emailSecond=null, emailThird=null, correspondingAuthor=0, authorType=1, ext={EN=AuthorExt(id=1201124487547810206, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1201124483961680071, authorId=1201124487405203852, language=EN, stringName=Hao-jie WANG, firstName=Hao-jie, middleName=null, lastName=WANG, prefix=null, suffix=null, authorComment=null, nameInitials=null, affiliation=null, department=null, xref=1, 2, 3, address=1. Henan University of Chinese Medicine, Co-construction of Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan & Education Ministry of China, Zhengzhou 450046, China
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Henan University of Chinese Medicine, Co-construction of Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan & Education Ministry of China, Zhengzhou 450046, China
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Chemical constituents from Potentilla nivea [J]. Chin Tradit Pat Med (中成药), 2022, 44: 456-460., articleTitle=null, refAbstract=null), Reference(id=1201124494690710482, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1201124483961680071, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[6], rfOrder=5, authorNames=null, journalName=null, refType=null, unstructuredReference=Wang JT, Li Y, Hu HP, et al. Chemical constituents from the n-butanol extract of Siegesbeckia pubescens [J]. 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No.δHδCNo.δHδC
2/156.43′, 5′6.87 (2H, d, J = 8.9 Hz)115.1
3/132.94′/161.3
4/177.41″5.44 (1H, d, J = 7.5 Hz)100.6
5/160.02″3.34 (1H, m)74.0
66.20 (1H, d, J = 2.0 Hz)98.73″3.25 (1H, m)76.1
7/164.24″3.09 (1H, m)70.0
86.42 (1H, d, J = 2.0 Hz)93.75″3.19 (1H, m)74.1
9/156.66″4.05 (2H, d, J = 4.5 Hz)63.2
10/104.01‴/174.3
1′/120.82‴3.89 (1H, m)65.4
2′, 6′7.98 (2H, d, J = 8.9 Hz)130.83‴0.87 (3H, d, J = 7.0 Hz)19.8
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1H and 13C NMR data of 1 (DMSO-d6)

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No.δHδCNo.δHδC
2/156.43′, 5′6.87 (2H, d, J = 8.9 Hz)115.1
3/132.94′/161.3
4/177.41″5.44 (1H, d, J = 7.5 Hz)100.6
5/160.02″3.34 (1H, m)74.0
66.20 (1H, d, J = 2.0 Hz)98.73″3.25 (1H, m)76.1
7/164.24″3.09 (1H, m)70.0
86.42 (1H, d, J = 2.0 Hz)93.75″3.19 (1H, m)74.1
9/156.66″4.05 (2H, d, J = 4.5 Hz)63.2
10/104.01‴/174.3
1′/120.82‴3.89 (1H, m)65.4
2′, 6′7.98 (2H, d, J = 8.9 Hz)130.83‴0.87 (3H, d, J = 7.0 Hz)19.8
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No.δHδCNo.δHδC
2/156.41‴/170.8
3/133.02‴2.94 (2H, m)37.1
4/177.33‴5.93 (1H, dt, J = 15.8, 7.1 Hz)120.1
5/161.24‴6.26 (1H, d, J = 15.8 Hz)131.6
66.19 (1H, d, J = 2.0 Hz)98.91‴′/130.4
7/164.72‴′, 6‴′7.26 (2H, d, J = 8.7 Hz)127.2
86.42 (1H, d, J = 2.0 Hz)93.83‴′, 5‴′7.01 (2H, d, J = 8.7 Hz)116.5
9/156.54‴′/156.9
10/103.71‴″4.80 (1H, d, J = 7.4 Hz)100.5
1′/120.82‴″2.95 (1H, m)73.9
2′, 6′8.01 (2H, d, J = 8.9 Hz)130.83‴″3.25 (1H, overlapped)76.5
3′, 5′6.89 (2H, d, J = 8.9 Hz)115.14‴″3.26 (1H, overlapped)69.6
4′/160.15‴″3.52 (1H, m)75.8
1″5.39 (1H, d, J = 7.3 Hz)101.16‴″3.56 (1H, m)
3.96 (1H, d, J = 10.5 Hz)		68.3
2″3.34 (1H, overlapped)73.41‴‴4.18 (1H, d, J = 7.6 Hz)103.9
3″3.15 (1H, m)76.22‴‴3.23 (1H, overlapped)73.2
4″3.15 (1H, m)69.93‴‴3.07 (1H, m)76.6
5″3.21 (1H, overlapped)74.14‴‴3.26 (1H, overlapped)69.9
6″4.14 (1H, d, J = 11.8 Hz)
4.02 (1H, dd, J = 11.8, 6.2 Hz)		63.15‴‴2.95 (1H, m)
3.67 (1H, dd, J = 11.2, 5.3 Hz)		65.7
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1H and 13C NMR data of 2 (DMSO-d6)

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No.δHδCNo.δHδC
2/156.41‴/170.8
3/133.02‴2.94 (2H, m)37.1
4/177.33‴5.93 (1H, dt, J = 15.8, 7.1 Hz)120.1
5/161.24‴6.26 (1H, d, J = 15.8 Hz)131.6
66.19 (1H, d, J = 2.0 Hz)98.91‴′/130.4
7/164.72‴′, 6‴′7.26 (2H, d, J = 8.7 Hz)127.2
86.42 (1H, d, J = 2.0 Hz)93.83‴′, 5‴′7.01 (2H, d, J = 8.7 Hz)116.5
9/156.54‴′/156.9
10/103.71‴″4.80 (1H, d, J = 7.4 Hz)100.5
1′/120.82‴″2.95 (1H, m)73.9
2′, 6′8.01 (2H, d, J = 8.9 Hz)130.83‴″3.25 (1H, overlapped)76.5
3′, 5′6.89 (2H, d, J = 8.9 Hz)115.14‴″3.26 (1H, overlapped)69.6
4′/160.15‴″3.52 (1H, m)75.8
1″5.39 (1H, d, J = 7.3 Hz)101.16‴″3.56 (1H, m)
3.96 (1H, d, J = 10.5 Hz)		68.3
2″3.34 (1H, overlapped)73.41‴‴4.18 (1H, d, J = 7.6 Hz)103.9
3″3.15 (1H, m)76.22‴‴3.23 (1H, overlapped)73.2
4″3.15 (1H, m)69.93‴‴3.07 (1H, m)76.6
5″3.21 (1H, overlapped)74.14‴‴3.26 (1H, overlapped)69.9
6″4.14 (1H, d, J = 11.8 Hz)
4.02 (1H, dd, J = 11.8, 6.2 Hz)		63.15‴‴2.95 (1H, m)
3.67 (1H, dd, J = 11.2, 5.3 Hz)		65.7
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窝儿七中2个新的黄酮苷类化合物
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王浩杰 1, 2, 3 , 赵晨 1 , 孙彦君 1, 2, 3, * , 弓建红 2, 3 , 白红云 2, 3 , 陈辉 2, 3 , 冯卫生 1, 3, *
药学学报 | 研究论文 2024,59(3): 673-677
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药学学报 | 研究论文 2024, 59(3): 673-677
窝儿七中2个新的黄酮苷类化合物
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王浩杰1, 2, 3, 赵晨1, 孙彦君1, 2, 3, * , 弓建红2, 3, 白红云2, 3, 陈辉2, 3, 冯卫生1, 3, *
作者信息
  • 1.河南中医药大学, 呼吸疾病中医药防治省部共建协同创新中心, 河南 郑州 450046
  • 2.河南中医药大学药学院, 河南 郑州 450046
  • 3.河南省中药开发工程技术中心, 河南 郑州 450046

通讯作者:

*孙彦君, Tel: 86-371-65962746, E-mail: ;
冯卫生, E-mail:
Two new flavonoid glycosides from Diphylleia sinensi
Hao-jie WANG1, 2, 3, Chen ZHAO1, Yan-jun SUN1, 2, 3, * , Jian-hong GONG2, 3, Hong-yun BAI2, 3, Hui CHEN2, 3, Wei-sheng FENG1, 3, *
Affiliations
  • 1. Henan University of Chinese Medicine, Co-construction of Collaborative Innovation Center for Chinese Medicine and Respiratory Diseases by Henan & Education Ministry of China, Zhengzhou 450046, China
  • 2. School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China
  • 3. Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou 450046, China
出版时间: 2024-03-12 doi: 10.16438/j.0513-4870.2023-1003
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摘要
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采用硅胶、MCI、凝胶、ODS等柱色谱以及半制备液相等现代色谱分离技术对窝儿七(Diphylleia sinensi) 乙醇提取物的乙酸乙酯洗脱部位和甲醇洗脱部位的化学成分进行分离纯化, 得到5个黄酮苷类化合物。运用现代波谱学方法(1D NMR、2D NMR、UV、IR和MS) 鉴定结构, 分别为山荷叶酮苷A (1)、山荷叶酮苷B (2)、槲皮素-3-O-β-D-葡萄糖苷(3)、山柰酚-3-O-β-D-葡萄糖苷(4)、山柰酚-3-O-(6″-O-乙酰)-β-D-葡萄糖苷(5)。化合物1和2为2个新的黄酮苷类化合物, 化合物3和5为首次从山荷叶属中分离得到。

窝儿七  /  化学成分  /  黄酮苷类化合物  /  提取分离  /  山荷叶属

Five flavonoid glycosides were isolated from the methanol and ethyl acetate fractions of the ethanol extract of Diphylleia sinensi by using various chromatographic methods, including silica gel, MCI gel, Sephadex LH-20, ODS and semi-preparative HPLC. The structures of the isolated compounds were identified as diphyflavonoid A (1), diphyflavonoid B (2), quercetin-3-O-β-D-glucopyranoside (3), kaempferol-3-O-β-D-glucopyranoside (4), kaempferol-3-O-(6″-O-acetyl)-β-D-glucopyranoside (5) by spectroscopy methods (1D NMR, 2D NMR, UV, IR, and MS). Compounds 1 and 2 were two new flavonoid glycosides, and compounds 3 and 5 were isolated from the genus Diphylleia for the first time.

Diphylleia sinensi  /  chemical constituent  /  flavonoid glycoside  /  extraction and isolation  /  Diphylleia
王浩杰, 赵晨, 孙彦君, 弓建红, 白红云, 陈辉, 冯卫生. 窝儿七中2个新的黄酮苷类化合物. 药学学报, 2024 , 59 (3) : 673 -677 . DOI: 10.16438/j.0513-4870.2023-1003
Hao-jie WANG, Chen ZHAO, Yan-jun SUN, Jian-hong GONG, Hong-yun BAI, Hui CHEN, Wei-sheng FENG. Two new flavonoid glycosides from Diphylleia sinensi[J]. Acta Pharmaceutica Sinica, 2024 , 59 (3) : 673 -677 . DOI: 10.16438/j.0513-4870.2023-1003
正文
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窝儿七为小檗科(Berberidaceae) 鬼臼亚科(Podophylloideae) 多年生草本植物中华山荷叶(Diphylleia sinensis) 的干燥根茎, 别名山荷叶、窝儿参、阿儿七等, 主要分布于我国西北和西南地区的陕西、甘肃、四川和云南等地[1, 2], 是陕西太白传统中药之一。具有清热败毒、破血祛瘀的功效, 主治风湿性关节炎、腰腿疼痛、骨蒸劳热、月经不调等症。药理活性研究表明, 其主要有抗肿瘤、抗病毒、抗氧化、抗菌、杀虫等作用[3]。化学成分研究表明窝儿七中主要含有木脂素、黄酮、甾醇、酚酸等类型化合物[3], 并且多集中于以鬼臼毒素为代表的木脂素类化合物。为寻找窝儿七中结构新颖的天然产物, 并为其应用开发提供理论依据, 本实验对窝儿七中的黄酮类化合物进行研究, 分离并鉴定了5个黄酮苷类化合物(1~5) (图 1), 其中化合物1和2为新化合物, 化合物3和5为首次从山荷叶属中分离得到。
结果与讨论
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化合物1, 淡黄色无定形粉末。HR-ESI-MS给出准分子离子峰m/z 543.110 4 [M+Na]+, 计算值为543.111 5 [M+Na]+, 推测分子式为C24H24O13。化合物1的IR光谱数据显示该化合物具有羟基(3 265 cm-1), 羰基(1 767, 1 656 cm-1), 苯环(1 607, 1 507 cm-1)。UV光谱中264和348 nm处的吸收峰提示含有黄酮醇结构片段。化合物1的1H NMR (500 MHz, DMSO-d6, 表 1) 显示存在1个葡萄糖端基氢信号[δH 5.44 (1H, d, J = 7.5 Hz)], 1个甲基氢信号[δH 0.87 (3H, d, J = 7.0 Hz)], 1组AA′BB′偶合系统的芳香质子信号[δH 7.98 (2H, d, J = 8.9 Hz)、6.87 (2H, d, J = 8.9 Hz)] 和1组黄酮醇6位和8位的特征质子信号[δH 6.42 (1H, d, J = 2.0 Hz), 6.20 (1H, d, J = 2.0 Hz)]。化合物1的13C NMR (125 MHz, DMSO-d6) 显示共计24个碳信号, 除了1组吡喃葡萄糖基碳信号[δC 100.6, 74.0, 76.1, 70.0, 74.1, 63.2] 和1组2-羟基丙酰基碳信号[δC 174.3, 65.4, 19.8] 之外, 还含有1个黄酮醇骨架碳信号, 其中包括1个羰基碳信号[δC 177.4], 12个芳香碳信号和2个连氧烯碳信号[δC 156.4, 132.9]。通过将其NMR数据与文献[4]报道的数据进行对比分析, 确定化合物1的苷元为山柰酚。
HMBC谱中, 由葡萄糖上H-6″ (δH 4.05) 及2-羟基丙酰基上H-3‴ (δH 0.87) 均与酯羰基碳C-1‴ (δC 174.3) 远程相关(图 2), 表明吡喃葡萄糖基6″上的羟基被2-羟基丙酸酯化。葡萄糖的端基氢质子H-1″ (δH 5.44) 与黄酮醇C-3 (δC 132.9) 的远程相关(图 2), 提示山柰酚3位羟基被葡萄糖糖苷化。糖端基碳的化学位移(δC 100.6) 以及氢的偶合常数(7.5 Hz), 表明葡萄糖基的端基氢的相对构型为β型。通过酸水解和HPLC分析, 检测到D-葡萄糖的存在。综上所述, 确定化合物1的结构为5, 7, 4′-三羟基黄酮3-O-[6″-O-(2‴-羟基-丙酰基)]-β-D-吡喃葡萄糖苷, 命名为山荷叶酮苷A。
化合物2, 淡黄色无定形粉末。HR-ESI-MS给出准分子离子峰m/z 925.237 0 [M+Na]+, 计算值为925.237 8 [M+Na]+, 推测分子式为C42H46O22。化合物2的IR光谱数据显示该化合物具有羟基(3 358 cm-1), 羰基(1 726, 1 656 cm-1), 苯环(1 607, 1 509 cm-1)。UV光谱中262和349 nm处的吸收峰提示含有黄酮醇结构片段。化合物2的1H NMR (500 MHz, DMSO-d6, 表 2) 显示存在1组AA′BB′偶合系统的芳香质子信号[δH 8.01 (2H, d, J = 8.9 Hz), 6.89 (2H, d, J = 8.9 Hz)], 1组1, 2, 3, 5四取代的芳香质子信号[δH 6.42 (1H, d, J = 2.0 Hz), 6.19 (1H, d, J = 2.0 Hz)], 3个糖端基氢信号[δH 5.39 (1H, d, J = 7.3 Hz), 4.80 (1H, d, J = 7.4 Hz), 4.18 (1H, d, J = 7.6 Hz)], 1个亚甲基氢信号[δH 2.94 (2H, m)], 以及2个烯氢质子信号[δH 6.26 (1H, d, J = 15.8 Hz), 5.93 (1H, dt, J = 15.8, 7.1 Hz)]。化合物2的13C NMR (125 MHz, DMSO-d6) 显示42个碳信号, 除了2组吡喃葡萄糖基碳信号(δC 101.1, 73.4, 76.2, 69.9, 74.1, 63.1, 100.5, 73.9, 76.5, 69.6, 75.8, 68.3), 1组木糖基碳信号(δC 103.9, 73.2, 76.6, 69.9, 65.7), 以及1组4-(4-羟基苯基)-3-丁烯酰基碳信号[δC 130.4, 127.2 (×2), 116.5 (×2), 156.9, 131.6, 120.1, 37.1, 170.8] 之外, 还有1个羰基碳信号(δC 177.3), 12个芳香碳信号和2个连氧烯碳信号(δC 156.4, 133.0)。通过将其NMR数据与文献[4]报道的数据进行对比分析, 确定化合物2苷元为山柰酚。根据糖端基质子偶合常数(2个葡萄糖, JH-1″ = 7.3 Hz, JH-1‴″ = 7.4 Hz, 1个木糖, JH-1‴‴ = 7.6 Hz) 及端基碳信号的化学位移(2个葡萄糖, δC 101.1, 100.5, 1个木糖, δC 103.9), 可以判断3个糖基的相对构型为β构型。3个糖的绝对构型采用与化合物1相同的方法, 确定为D型。
由木糖基的端基氢质子H-1‴‴ (δH 4.18) 与葡萄糖基C-6‴″ (δC 68.3) 的HMBC相关(图 2), 以及葡萄糖基H-1‴″ (δH 4.80) 与4-(4-羟基苯基)-3-丁烯酰基C-4‴′ (δC 156.9) 的HMBC相关(图 2), 表明β-D-木糖与β-D-葡萄糖是1→6相连, 且4-(4-羟基苯基)-3-丁烯酰基上的羟基被该糖链上的葡萄糖糖苷化。葡萄糖基上的亚甲基氢信号[δH 4.02 (1H, dd, J = 11.8, 6.2 Hz), 4.14 (1H, d, J = 11.8 Hz)] 与端基氢信号δH 5.39 (1H, d, J = 7.3 Hz, H-1″) 分别与4-(4-羟基苯基)-3-丁烯酰基上的酯羰基碳信号C-1‴ (δC 170.8), 苷元上烯碳信号C-3 (δC 133.0) 的HMBC相关(图 2), 提示吡喃葡萄糖基的6″-羟基被4-(4-羟基苯基)-3-丁烯酸酯化, 苷元3位羟基被葡萄糖糖苷化。综上所述, 确定化合物2的结构为5, 7, 4′-三羟基黄酮3-O-(6″-O-{4‴-[4‴′-O-β-D-木糖基-(1‴‴→6‴″)-β-D-吡喃葡萄糖基-苯基]}-3‴-丁烯酰基)-β-D-吡喃葡萄糖苷, 命名为山荷叶酮苷B。
通过谱学数据与文献对照, 确定3个已知化合物, 分别为槲皮素-3-O-β-D-葡萄糖苷(3)[5]、山柰酚-3-O-β-D-葡萄糖苷(4)[6]、山柰酚-3-O-(6″-O-乙酰)-β-D-葡萄糖苷(5)[7]。
实验部分
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Bruker AM-500 MHz核磁共振谱用超导核磁共振仪(TMS做内标, 德国Bruker公司); TripleTOF 6600型高效液相色谱-高分辨质谱联用仪(美国ABSCIEX公司); 赛谱锐思LC-52型半制备液相色谱仪(中国赛谱锐思北京科技有限公司); Anton Paar MCP 5100型旋光仪(奥地利Anton Paar); Thermo EVO300紫外分光光度计和Thermo Nicolet IS10红外光谱仪(美国Thermo Scientific); N-1100型旋转蒸发仪和EYELACA-3310型低温冷凝循环泵(日本东京理化器械株式会社); 原子型1820C型纯水机(重庆摩尔水处理设备有限公司); MCI Gel CHP-20柱色谱材料(日本三菱化学公司); Sephadex LH-20柱色谱材料(瑞典Parmacia Biotech); AB-8大孔吸附树脂(中国郑州勤实科技有限公司); 硅藻土和正相硅胶柱色谱材料(200~300目, 青岛海洋化工厂); YMC-Pack ODS-A色谱柱(250 mm × 20 mm, 5 μm) 和C18 ODS柱色谱材料(50 μm, 日本YMC有限公司), 色谱纯及分析纯试剂(天津四友精细化学品有限公司), D-葡萄糖和D-木糖标准品(德国Sigma公司)。
窝儿七药材于2019年7月采集于四川省, 经河南中医药大学药学院董诚明教授鉴定为山荷叶属植物中华山荷叶(Diphylleia sinensis) 的干燥根茎。凭证样品(DS 20190728) 存放于河南中医药大学药学院标本室。
1 提取分离
取干燥的窝儿七根茎40.00 kg, 用95%乙醇、50%乙醇各回流提取3次, 每次2 h, 滤过, 合并提取液, 减压浓缩, 得浸膏5.20 kg。浸膏用甲醇溶解后, 将其分散在2倍量的硅藻土中, 再用不同极性的有机溶剂洗脱, 得到以下3个洗脱部位: 二氯甲烷洗脱部位(1 942.00 g)、乙酸乙酯洗脱部位(690.00 g)、甲醇洗脱部位(1 808.00 g)。甲醇洗脱部位(1 808.00 g) 采用硅胶柱色谱分离, 使用二氯甲烷-甲醇(100∶0~0∶100) 系统洗脱, 得到7个组分(M1~M7)。M4 (117.50 g) 分离沉淀与母液, 母液使用Sephadex LH-20凝胶柱色谱分离, 甲醇洗脱, 得到3个组分(M4-1~M4-3)。M4-2 (39.20 g) 使用硅胶柱色谱分离, 以二氯甲烷-甲醇(100∶1~3∶1) 系统梯度洗脱, 得到3个组分(M4-2-1~M4-2-3)。M4-2-3 (1.40 g) 采用半制备高效液相色谱分离纯化, 以48%甲醇洗脱, 流速为6 mL·min-1, 得到化合物1 (tR = 35.20 min, 3.00 mg)。M4-3 (10.50 g) 经Sephadex LH-20凝胶柱色谱分离, 甲醇洗脱, 得到化合物4 (35.00 mg)。M5 (120.60 g) 采用AB-8大孔吸附树脂, 乙醇-水(0%~90%) 梯度洗脱, 得到4个组分(M5-1~M5-4)。M5-2 (32.80 g) 采用MCI柱色谱, 以甲醇-水(10%~70%) 梯度洗脱, 得到3个组分(M5-2-1~M5-2-3), 将M5-2-2 (3.50 g) 经半制备高效液相色谱(6 mL·min-1) 分离纯化, 以50%甲醇洗脱, 得到化合物2 (tR = 31.34 min, 4.30 mg)。乙酸乙酯洗脱部位(690.00 g) 采用硅胶柱色谱分离, 二氯甲烷-甲醇(100∶0~0∶100) 系统梯度洗脱, 得到5个组分(E1~E5)。E3分离沉淀与母液, 将母液(100.60 g) 采用ODS柱色谱分离, 甲醇-水(10%~70%) 进行洗脱, 得到3个组分(E3-1~E3-3)。E3-3 (24.00 g) 通过硅胶柱色谱分离, 采用石油醚-乙酸乙酯(100∶3~1∶1) 洗脱, 得到7个组分(E3-3-1~E3-3-7)。E3-3-4 (5.50 g) 经Sephadex LH-20凝胶柱色谱分离, 甲醇洗脱, 得到6个组分(E3-3-4-1~E3-3-4-6)。E3-3-4-5 (0.50 g) 经半制备高效液相色谱分离, 流速为3 mL·min-1, 70%甲醇为流动相, 得到化合物5 (tR = 15.52 min, 3.00 mg)。E3-3-5 (2.80 g) 经Sephadex LH-20凝胶柱色谱分离, 甲醇洗脱, 得到7个组分(E3-3-5-1~E3-3-5-7)。E3-3-5-3 (95.8 mg) 经半制备高效液相色谱分离纯化, 以62%甲醇洗脱, 流速为3 mL·min-1, 得到化合物3 (tR = 10.30 min, 3.00 mg)。
2 酸水解
取化合物1 (1.5 mg), 加少量甲醇溶解后加入0.025 mol·L-1硫酸溶液1.0 mL, 搅拌均匀后在90 ℃的水浴锅上放置3 h, 冷却后加入5.0 mL水稀释, 并用10.0 mL二氯甲烷萃取, 水层中加入饱和的Ba(OH)2溶液, 中和至中性, 过滤, 滤液减压浓缩, 得到糖部分。将糖部分加入L-半胱氨酸甲酯(1.5 mg) 和吡啶(1.0 mL), 在60 ℃水浴锅上加热1.5 h。向混合溶液中加入邻甲苯异硫氰酸酯(15.0 μL), 在60 ℃下加热1.5 h。用半制备高效液相直接分析混合物, 以30%乙腈-水(含0.2% CF3COOH) 为流动相, 流速为3 mL·min-1, 色谱柱使用YMC (250 mm × 20 mm) 反相色谱制备柱, 在紫外检测器250 nm下检测。通过比较样品保留时间(18.63 min) 与D-葡萄糖标准品的保留时间, 确定化合物1中葡萄糖的绝对构型为D型。化合物2采用同样方法水解确定葡萄糖绝对构型为D型, 通过比较样品保留时间(25.34 min) 与D-木糖标准品的保留时间, 确定化合物2中木糖的绝对构型为D型, 由D-葡萄糖和D-木糖的峰面积之比, 确定它们摩尔比为2∶1[8]。
3 结构鉴定
化合物1   淡黄色无定形粉末, 易溶于甲醇; HR-ESI-MS m/z 543.110 4 [M+Na]+ (计算值为C24H24O13Na+, 543.111 5); 旋光值为[α]$ {}_{\mathrm{D}}^{20} $ -8.90 (c 0.10, MeOH); UV (MeOH) λmax (log ε) 202 (4.16), 264 (3.96), 348 (3.90) nm; IR νmax 3 265, 2 926, 2 882, 1 767, 1 656, 1 607, 1 571, 1 507, 1 445, 1 361, 1 307, 1 286, 1 212, 1 180, 1 117, 1 070 cm-1; 1H NMR (500 MHz, DMSO-d6) 和13C NMR (125 MHz, DMSO-d6) 数据见表 1。
化合物2    淡黄色无定形粉末, 易溶于甲醇; HR-ESI-MS m/z 925.237 0 [M+Na]+ (计算值为C42H46O22Na+, 925.237 8); 旋光值为[α]$ {}_{\mathrm{D}}^{20} $ -40.70 (c 0.07, MeOH); UV (MeOH) λmax (log ε) 202 (4.74), 262 (4.55), 349 (4.21) nm; IR νmax 3 358, 2 921, 2 851, 1 726, 1 656, 1 607, 1 575, 1 509, 1 455, 1 361, 1 305, 1 287, 1 235, 1 211, 1 180, 1 073, 1 040 cm-1; 1H NMR (500 MHz, DMSO-d6) 和 13C NMR (125 MHz, DMSO-d6) 数据见表 2。
作者贡献: 孙彦君和冯卫生负责实验设计; 王浩杰、赵晨负责实验实施、数据处理; 弓建红、白红云、陈辉参与实验实施; 王浩杰负责论文撰写; 孙彦君负责文章的审阅和提出论文写作的建议。
利益冲突: 作者声明无利益冲突。
基金
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  • 河南中医药大学省属高校基本科研业务专项(2014KYYWF-QN26)
  • 河南中医药大学科技创新人才(2016XCXRC01)
  • 河南省科技攻关(192102310438)
  • 河南省中医药科学研究专项(20-21ZY1039)
文献
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doi: 10.16438/j.0513-4870.2023-1003
  • 接收时间：2023-08-28
  • 首发时间：2025-11-28
  • 出版时间：2024-03-12
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  • 收稿日期：2023-08-28
  • 修回日期：2023-09-22
基金
河南中医药大学省属高校基本科研业务专项(2014KYYWF-QN26)
河南中医药大学科技创新人才(2016XCXRC01)
河南省科技攻关(192102310438)
河南省中医药科学研究专项(20-21ZY1039)
作者信息
    1.河南中医药大学, 呼吸疾病中医药防治省部共建协同创新中心, 河南 郑州 450046
    2.河南中医药大学药学院, 河南 郑州 450046
    3.河南省中药开发工程技术中心, 河南 郑州 450046

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*孙彦君, Tel: 86-371-65962746, E-mail: ;
冯卫生, 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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