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Article(id=1308841991488766377, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2026-0205, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1771948800000, receivedDateStr=2026-02-25, revisedDate=1775318400000, revisedDateStr=2026-04-05, acceptedDate=null, acceptedDateStr=null, onlineDate=1789981847879, onlineDateStr=2026-09-21, pubDate=1783785600000, pubDateStr=2026-07-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789981847879, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789981847879, creator=13701087609, updateTime=1789981847879, updator=13701087609, issue=Issue{id=1308841897058198067, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='7', pageStart='2377', pageEnd='2820', issueExtLink='null', onlineDate='null', pubDate='1783785600000', pubDateStr='2026-07-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981825365, creator='13701087609', updateTime=1789984154811, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851667525792021, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851667525792022, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308841897058198067, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=2611, endPage=2617, ext={EN=ArticleExt(id=1308841991706870186, articleId=1308841991488766377, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Isolation and identification of six new compounds from Zingiberis Rhizoma, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Six new compounds including two diarylheptanoids (1, 2), one norlignan (3), and three gingerenols (4-6) were isolated from the rhizoma of Zingiber officinale by column chromatography of Diaion HP-20, MCI Gel CHP-20, Sephadex LH-20, ODS-A gel and semi-preparative HPLC. Structural identification of the isolated compounds was performed via modern spectroscopic methods (1D and 2D NMR, UV, IR, and MS), and they were characterized as 3-keto-5(R)-(6-amino-9H-purin-9-yl)-1, 7-(4-hydroxy-3-methoxyphenyl)-heptane (1), (5α, 6α)1, 5-epoxy-3-one-6-hydroxy-1, 7-(4-dihydroxy-3-methoxyphenyl)-heptane (2), (2S)1-(bis(4-hydroxy-3-methoxyphenyl)methyl)-dihydrofuran-5-(2H)one (3), 1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 6-triol (4), 1-(4-hydroxy-3-methoxyphenyl)-decane-3, 8-diol (5) and 1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 10-triol (6), by using modern spectroscopic methods (1D and 2D NMR, UV, IR, and MS). The absolute configurations of compounds 1 and 3 were determined through the comparisons of optical rotations in references. However, the ECD data of compound 3 were failed to obtain, and only the relative configuration was determined through the NMR calculations. Due to insufficient sample amounts, the absolute configurations of compounds 3-6 were not further determined.

, authors=Wen-xuan ZHAO, Ying-ying SI, Yan-zhi WANG, Xiao-kun LI*, authorsList=Wen-xuan ZHAO, Ying-ying SI, Yan-zhi WANG, Xiao-kun LI, authorCompany=null, correspAuthors=Xiao-kun LI, 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=1308841992298267055, articleId=1308841991488766377, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=干姜中六个新化合物的分离与鉴定, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

运用Diaion HP-20、MCI Gel CHP-20、Sephadex LH-20、ODS-A gel等柱层析方法和半制备高效液相等色谱技术, 从干姜中分离出6个新化合物, 包括2个二苯基庚烷(1, 2)、1个降木脂素(3) 和3个姜烯酚(4~6)。用现代波谱学方法(1D、2D NMR、UV、IR和MS等) 对所分离得到的化合物进行结构鉴定, 分别鉴定为3-keto-5(R)-(6-amino-9H-purin-9-yl)-1, 7-(4-hydroxy-3-methoxyphenyl)-heptane (1)、(5α, 6α)1, 5-epoxy-3-one-6-hydroxy-1, 7-(4-dihydroxy-3-methoxyphenyl)-heptane (2)、(2S)1-(bis(4-hydroxy-3-methoxyphenyl)methyl)-dihydrofuran-5-(2H)one (3)、1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 6-triol (4)、1-(4-hydroxy-3-methoxyphenyl)-decane-3, 8-diol (5) 和1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 10-triol (6)。化合物1和3通过比旋度对比确定了绝对构型, 2未能获得CD数据, 仅通过计算碳谱确定了相对构型; 化合物3~6因样品量较少无法衍生化, 绝对构型暂未进一步确定。

, authors=赵文萱, 司盈盈, 王彦志, 李晓坤*, authorsList=赵文萱, 司盈盈, 王彦志, 李晓坤, authorCompany=null, correspAuthors=李晓坤, authorNote=

作者贡献:

赵文萱负责实验实施、数据处理和论文撰写; 司盈盈参与实验指导; 李晓坤负责论文数据整理; 王彦志负责实验设计及论文的定稿和修改。

, correspAuthorsNote=
李晓坤, Tel: 86-13523408977, E-mail:
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Qualitative analysis on chemical constituents from different polarity extracted fractions of the pulp and peel of ginger rhizomes by ultra-high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry [J]. Rapid Commun Mass Spectrom, 2021, 35: e9029., articleTitle=null, refAbstract=null), Reference(id=1308842000032563685, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841991488766377, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=11, rfOrder=10, authorNames=null, journalName=null, refType=null, unstructuredReference=Araya JJ, Zhang H, Jakobsche CE, et al. Identification of unprecedented purine-containing compounds, the zingerines, from ginger rhizomes (Zingiber officinale Roscoe) using a phase-trafficking approach [J]. 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No.123
δHδCδHδCδHδC
12.64 (2H, m)30.3173.14.39 (1H, d, 5.8)51.4
2Ha: 2.37 (1H, m)
Hb: 3.06 (1H, m)		45.55.98 (1H, m)100.63.50 (1H, td, 8.9, 5.7)45.1
3209.4196.7Ha: 2.45 (1H, m)
Hb: 2.12 (1H, m)		27.7
42.64 (2H, m)47.6Ha: 2.94 (1H, dd, 17.0, 14.8)
Hb: 2.32 (1H, dd, 17.0, 3.2)		38.6Ha: 4.20 (1H, m)
Hb: 3.96 (1H, m)		68.1
54.90 (1H, m)53.64.41 (1H, dt, 14.8, 2.8)81.6181.3
6Ha: 2.47 (1H, m)
Hb: 2.13 (1H, m)		36.23.91(1H, dd, 7.1, 2.8)74.3
7Ha: 2.41 (1H, m)
Hb: 2.18 (1H, m)		32.9Ha: 3.09 (1H, dd, 13.6, 6.8)
Hb: 3.02 (1H, dd, 13.6, 7.6)		40.3
1′133.6125.0135.0
2′6.55 (1H, d, 2.0)112.97.48 (1H, d, 2.0)110.96.81 (1H, d, 2.0)113.4
3′148.8152.2148.9
4′145.7148.9146.4
5′6.62 (1H, d, 8.0)116.06.91 (1H, d, 8.0)116.36.78 (1H, d, 8.0)116.0
6′6.44 (1H, dd, 8.0, 2.0)121.67.47 (1H, dd, 8.0, 2.0)122.26.76 (1H, dd, 8.0, 2.0)121.5
1′′133.1130.8135.7
2′′6.55 (1H, d, 2.0)112.86.85 (1H, d, 1.5)114.06.77 (1H, d, 8.0)113.7
3′′148.8149.2148.8
4′′145.7146.1146.4
5′′6.62 (1H, d, 8.0)116.06.71 (1H, d, 8.0)116.56.70 (1H, d, 1.8)116.0
6′′6.44 (1H, dd, 8.0, 2.0)121.56.72 (1H, dd, 8.0, 1.5)122.96.61 (1H, dd, 8.0, 1.8)121.5
3′-OCH33.74 (3H, s)56.33.71 (3H, s)56.23.78 (3H, s)56.4
3′′-OCH33.73 (3H, s)56.23.92 (3H, s)56.53.76 (3H, s)56.3
), ArticleFig(id=1308841999042707928, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308841991488766377, language=CN, label=Tab.1, caption=

1H (500 MHz) and 13C (125 MHz) data for compounds 1-3 in CD3OD (δ in ppm, J in Hz)

, figureFileSmall=null, figureFileBig=null, tableContent=
No.123
δHδCδHδCδHδC
12.64 (2H, m)30.3173.14.39 (1H, d, 5.8)51.4
2Ha: 2.37 (1H, m)
Hb: 3.06 (1H, m)		45.55.98 (1H, m)100.63.50 (1H, td, 8.9, 5.7)45.1
3209.4196.7Ha: 2.45 (1H, m)
Hb: 2.12 (1H, m)		27.7
42.64 (2H, m)47.6Ha: 2.94 (1H, dd, 17.0, 14.8)
Hb: 2.32 (1H, dd, 17.0, 3.2)		38.6Ha: 4.20 (1H, m)
Hb: 3.96 (1H, m)		68.1
54.90 (1H, m)53.64.41 (1H, dt, 14.8, 2.8)81.6181.3
6Ha: 2.47 (1H, m)
Hb: 2.13 (1H, m)		36.23.91(1H, dd, 7.1, 2.8)74.3
7Ha: 2.41 (1H, m)
Hb: 2.18 (1H, m)		32.9Ha: 3.09 (1H, dd, 13.6, 6.8)
Hb: 3.02 (1H, dd, 13.6, 7.6)		40.3
1′133.6125.0135.0
2′6.55 (1H, d, 2.0)112.97.48 (1H, d, 2.0)110.96.81 (1H, d, 2.0)113.4
3′148.8152.2148.9
4′145.7148.9146.4
5′6.62 (1H, d, 8.0)116.06.91 (1H, d, 8.0)116.36.78 (1H, d, 8.0)116.0
6′6.44 (1H, dd, 8.0, 2.0)121.67.47 (1H, dd, 8.0, 2.0)122.26.76 (1H, dd, 8.0, 2.0)121.5
1′′133.1130.8135.7
2′′6.55 (1H, d, 2.0)112.86.85 (1H, d, 1.5)114.06.77 (1H, d, 8.0)113.7
3′′148.8149.2148.8
4′′145.7146.1146.4
5′′6.62 (1H, d, 8.0)116.06.71 (1H, d, 8.0)116.56.70 (1H, d, 1.8)116.0
6′′6.44 (1H, dd, 8.0, 2.0)121.56.72 (1H, dd, 8.0, 1.5)122.96.61 (1H, dd, 8.0, 1.8)121.5
3′-OCH33.74 (3H, s)56.33.71 (3H, s)56.23.78 (3H, s)56.4
3′′-OCH33.73 (3H, s)56.23.92 (3H, s)56.53.76 (3H, s)56.3
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No.456
δHδCδHδCδHδC
1Ha: 2.71 (1H, m)
Hb: 2.54 (1H, m)		32.72.70 (2H, m)32.6Ha: 2.70 (1H, m)
Hb: 2.53 (1H, m)		32.7
21.74 (2H, m)41.51.71 (2H, m)40.71.72 (2H, m)41.4
33.80 (1H, m)68.73.52 (1H, m)71.73.79 (1H, m)68.7
41.63 (2H, m)41.71.47 (2H, m)38.51.50 (2H, m)45.7
53.69 (1H, m)72.01.43 (2H, m)26.83.79 (1H, m)69.2
63.35 (1H, m)75.91.43 (2H, m)26.81.45 (2H, m)39.1
71.53 (2H, m)33.61.47 (2H, m)37.61.35 (2H, m)27.0
81.48 (2H, m)29.33.42 (1H, m)73.81.35 (2H, m)26.6
91.43 (2H, m)23.81.43 (2H, m)31.01.67 (2H, m)33.6
100.92 (3H, t, 7.0)14.40.92 (3H, t, 7.0)10.33.55 (2H, t, 6.5)62.9
1′135.3135.3135.3
2′6.77 (1H, d, 1.5)113.26.76 (1H, d, 1.5)113.26.77 (1H, d, 1.5)113.2
3′148.8148.8148.8
4′145.4145.4145.5
5′6.68 (1H, d, 8.0)116.16.69 (1H, d, 8.0)116.16.68 (1H, d, 8.0)116.1
6′6.63 (1H, d, 8.0, 1.5)121.86.66 (1H, d, 8.0, 1.5)121.86.63 (1H, d, 8.0, 1.5)121.8
3′-OCH33.82 (3H, s)56.33.82 (3H, s)56.33.82 (3H, s)56.3
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1H (500 MHz) and 13C (125 MHz) data for compounds 4-6 in CD3OD (δ in ppm, J in Hz)

, figureFileSmall=null, figureFileBig=null, tableContent=
No.456
δHδCδHδCδHδC
1Ha: 2.71 (1H, m)
Hb: 2.54 (1H, m)		32.72.70 (2H, m)32.6Ha: 2.70 (1H, m)
Hb: 2.53 (1H, m)		32.7
21.74 (2H, m)41.51.71 (2H, m)40.71.72 (2H, m)41.4
33.80 (1H, m)68.73.52 (1H, m)71.73.79 (1H, m)68.7
41.63 (2H, m)41.71.47 (2H, m)38.51.50 (2H, m)45.7
53.69 (1H, m)72.01.43 (2H, m)26.83.79 (1H, m)69.2
63.35 (1H, m)75.91.43 (2H, m)26.81.45 (2H, m)39.1
71.53 (2H, m)33.61.47 (2H, m)37.61.35 (2H, m)27.0
81.48 (2H, m)29.33.42 (1H, m)73.81.35 (2H, m)26.6
91.43 (2H, m)23.81.43 (2H, m)31.01.67 (2H, m)33.6
100.92 (3H, t, 7.0)14.40.92 (3H, t, 7.0)10.33.55 (2H, t, 6.5)62.9
1′135.3135.3135.3
2′6.77 (1H, d, 1.5)113.26.76 (1H, d, 1.5)113.26.77 (1H, d, 1.5)113.2
3′148.8148.8148.8
4′145.4145.4145.5
5′6.68 (1H, d, 8.0)116.16.69 (1H, d, 8.0)116.16.68 (1H, d, 8.0)116.1
6′6.63 (1H, d, 8.0, 1.5)121.86.66 (1H, d, 8.0, 1.5)121.86.63 (1H, d, 8.0, 1.5)121.8
3′-OCH33.82 (3H, s)56.33.82 (3H, s)56.33.82 (3H, s)56.3
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干姜中六个新化合物的分离与鉴定
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赵文萱 , 司盈盈 , 王彦志 , 李晓坤 *
药学学报 | 研究论文 2026,61(7): 2611-2617
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药学学报 |研究论文 2026 , 61 (7) : 2611 -2617
干姜中六个新化合物的分离与鉴定
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赵文萱, 司盈盈, 王彦志, 李晓坤*
作者信息
  • 河南中医药大学药学院, 河南 郑州 450046
通讯作者:
李晓坤, Tel: 86-13523408977, E-mail:
作者简介:

作者贡献:

赵文萱负责实验实施、数据处理和论文撰写; 司盈盈参与实验指导; 李晓坤负责论文数据整理; 王彦志负责实验设计及论文的定稿和修改。

Isolation and identification of six new compounds from Zingiberis Rhizoma
Wen-xuan ZHAO, Ying-ying SI, Yan-zhi WANG, Xiao-kun LI*
Affiliations
  • School of Pharmacy, Henan University of Chinese Medicine, Zhengzhou 450046, China
出版时间: 2026-07-12 doi: 10.16438/j.0513-4870.2026-0205
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摘要
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运用Diaion HP-20、MCI Gel CHP-20、Sephadex LH-20、ODS-A gel等柱层析方法和半制备高效液相等色谱技术, 从干姜中分离出6个新化合物, 包括2个二苯基庚烷(1, 2)、1个降木脂素(3) 和3个姜烯酚(4~6)。用现代波谱学方法(1D、2D NMR、UV、IR和MS等) 对所分离得到的化合物进行结构鉴定, 分别鉴定为3-keto-5(R)-(6-amino-9H-purin-9-yl)-1, 7-(4-hydroxy-3-methoxyphenyl)-heptane (1)、(5α, 6α)1, 5-epoxy-3-one-6-hydroxy-1, 7-(4-dihydroxy-3-methoxyphenyl)-heptane (2)、(2S)1-(bis(4-hydroxy-3-methoxyphenyl)methyl)-dihydrofuran-5-(2H)one (3)、1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 6-triol (4)、1-(4-hydroxy-3-methoxyphenyl)-decane-3, 8-diol (5) 和1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 10-triol (6)。化合物1和3通过比旋度对比确定了绝对构型, 2未能获得CD数据, 仅通过计算碳谱确定了相对构型; 化合物3~6因样品量较少无法衍生化, 绝对构型暂未进一步确定。

干姜  /  化学成分  /  二苯基庚烷类  /  姜烯酚类  /  分离鉴定

Six new compounds including two diarylheptanoids (1, 2), one norlignan (3), and three gingerenols (4-6) were isolated from the rhizoma of Zingiber officinale by column chromatography of Diaion HP-20, MCI Gel CHP-20, Sephadex LH-20, ODS-A gel and semi-preparative HPLC. Structural identification of the isolated compounds was performed via modern spectroscopic methods (1D and 2D NMR, UV, IR, and MS), and they were characterized as 3-keto-5(R)-(6-amino-9H-purin-9-yl)-1, 7-(4-hydroxy-3-methoxyphenyl)-heptane (1), (5α, 6α)1, 5-epoxy-3-one-6-hydroxy-1, 7-(4-dihydroxy-3-methoxyphenyl)-heptane (2), (2S)1-(bis(4-hydroxy-3-methoxyphenyl)methyl)-dihydrofuran-5-(2H)one (3), 1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 6-triol (4), 1-(4-hydroxy-3-methoxyphenyl)-decane-3, 8-diol (5) and 1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 10-triol (6), by using modern spectroscopic methods (1D and 2D NMR, UV, IR, and MS). The absolute configurations of compounds 1 and 3 were determined through the comparisons of optical rotations in references. However, the ECD data of compound 3 were failed to obtain, and only the relative configuration was determined through the NMR calculations. Due to insufficient sample amounts, the absolute configurations of compounds 3-6 were not further determined.

Zingiber officinale Rosc  /  chemical composition  /  diphenylheptane glycosides  /  gingerol  /  isolation and identification
赵文萱, 司盈盈, 王彦志, 李晓坤. 干姜中六个新化合物的分离与鉴定. 药学学报, 2026 , 61 (7) : 2611 -2617 . DOI: 10.16438/j.0513-4870.2026-0205
Wen-xuan ZHAO, Ying-ying SI, Yan-zhi WANG, Xiao-kun LI. Isolation and identification of six new compounds from Zingiberis Rhizoma[J]. Acta Pharmaceutica Sinica, 2026 , 61 (7) : 2611 -2617 . DOI: 10.16438/j.0513-4870.2026-0205
正文
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干姜(Zingiberis Rhizoma) 是姜科植物姜(Zingiber officinale Rosc.) 的干燥根茎, 是最受欢迎的香料之一, 也是传统温里类中药[1]。现代药理学活性研究表明, 干姜具有抗氧化、抗炎、解热、抗癌和抑制血小板聚集等多种药理作用[2-8], 其中的挥发油、二苯基庚烷、姜烯酚和萜类等化学成分均具有生物活性[9]。目前, 关于干姜的化学成分研究主要集中在挥发油和姜烯酚等非极性成分上。为了进一步阐明干姜的物质基础, 我们对干姜的中等极性成分进行了深入研究。本文报道了从干姜乙酸乙酯部位中分离出的2个新二苯基庚烷类化合物(1, 2)、1个新的降木脂素(3) 和3个新的姜烯酚衍生物(4~6), 见图1。其中, 化合物1和2曾在前期的LC-MS分析中被检测到[10], 本次经实验成功分离鉴定并归属其波谱数据。
结果与讨论
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化合物1为白色固体, [α]$ {}_{\mathrm{D}}^{20} $ -14.62 (c 0.03, MeOH), HR-ESI-MS给出准分子离子峰m/z 492.225 5 [M+H]+, 计算值为492.224 1, 推测分子式为C26H29N5O5, 不饱和度为15。在1H NMR (CD3OD, 500 MHz) 谱(表1) 中, 芳香区有6个氢质子信号[δH 6.62 (2H, d, J = 8.0 Hz, H-5′, 5″), 6.55 (2H, d, J = 2.0 Hz, H-2′, 2″), 6.44 (2H, dd, J = 8.0, 2.0 Hz, H-6′, 6″)], 提示结构中含有两个苯环, 均为ABX偶合系统; δH 3.74 (3H, s, 3′-OCH3), 3.73 (3H, s, 3″-OCH3) 为2个甲氧基氢信号。13C NMR (CD3OD, 125 MHz) 谱中, 高场区出现了6个碳信号, 包括5个亚甲基[δC 47.6 (C-4), 45.5 (C-2), 36.2 (C-6), 32.9 (C-7), 30.3 (C-1)], 1个次甲基[δC 53.6 (C-5)] 和1个酮羰基碳信号δC 209.4 (C-3), 结合[δC 148.8 (C-3′, 3″), 145.7 (C-4′, 4″), 133.6 (C-1′), 133.1 (C-1″), 121.6 (C-6′), 121.5 (C-6″), 116.0 (C-5′, 5″), 112.9 (C-2′), 112.8 (C-2″)] 之间两个苯环的12个碳信号, 推测该化合物为二苯基庚烷类化合物; δC 56.3 (3′-OCH3), 56.2 (3″-OCH3) 为2个甲氧基碳信号。除了以上碳信号外, 13C NMR谱中还有5个不饱和碳原子(δC 157.2, 153.3, 150.5, 142.4, 120.3), 与文献[11]中描述的嘌呤片段信号一致。在HMBC谱(图2) 中, H-1与C-1′、C-2′、C-2、C-3相关, H-2与C-1′、C-3、C-4相关, H-6与C-1″、C-5相关, H-7与C-1″、C-2″、C-5、C-6相关; 证明有一个庚烷片段存在, 并且两个ABX系统的苯环分别与庚烷片段的C-1和C-7相连。H-5与C-3、C-4、C-7、C-4‴、C-8‴的相关信号, 再结合C-5较大的化学移值(δC 53.6), 推测嘌呤片段连接在C-5位上。化合物1的旋光值与文献[12]中鼠尾草姜黄素的旋光值([α]$ {}_{\mathrm{D}}^{20} $ -8.1) 接近, 推测化合物1与鼠尾草姜黄素的绝对构型相同。综上所述, 确定化合物1的结构为3-keto-5(R)-(6-amino-9H-purin-9-yl)-1, 7-(4-hydroxy-3-methoxyphenyl)-heptane。
化合物2为浅黄色固体。[α]$ {}_{\mathrm{D}}^{20} $ -127.57 (c 0.03, MeOH), HR-ESI-MS给出准分子离子峰m/z 387.143 5 [M+H]+, 计算值为387.143 8, 推测其分子式为C21H22O7, 不饱和度为11。在1H NMR (CD3OD, 500 MHz) 谱(表1) 显示两组ABX偶合系统的苯环氢信号[δH 7.48 (1H, d, J = 2.0 Hz, H-2′), 7.47 (1H, dd, J = 8.0, 2.0 Hz, H-6′), 6.91 (1H, d, J = 8.0 Hz, H-5′), 6.85 (1H, d, J = 1.5 Hz, H-2″), 6.72 (1H, d, J = 8.0, 1.5 Hz, H-6″), 6.71 (1H, d, J = 8.0 Hz, H-5″)], δH 5.98 (1H, s, H-2) 处为双键上氢信号, δH 3.92 (3H, s, 3″-OCH3), 3.71 (3H, s, 3′-OCH3) 为2个甲氧基氢信号。在13C NMR (CD3OD, 125 MHz) 谱(表1) 中, 除了芳香区的12个碳信号外, 还有2个甲氧基碳信号[δC 56.5 (3″-OCH3), 56.2 (3′-OCH3)], 以及1个羰基碳信号[δC 196.7 (C-3)], 2个不饱和碳信号[(δC 173.1 (C-1), 100.6 (C-2)], 2个连氧次甲基碳信号[δC 81.6 (C-5), 74.3 (C-6)], 2个亚甲基碳信号[δC 40.3 (C-7), 38.6 (C-4)], 以上数据表明化合物2也是一个二苯基庚烷类化合物。在HMBC谱(图2) 中, H-2与C-1′、C-1、C-3、C-4相关, 提示双键位于C-1、C-2位。根据1H-1H COSY谱中H-6与H-7a、H-5、H-4a、H-4b的相关信号, HMBC谱中H-5和C-1相关, 证明存在C1-O-C5吡喃环。HMBC谱中还出现H-7a与C-1″、C-2″、C-6″、C-5和C-6相关; H-2′, H-6′与C-1、C-1′、C-3′、C-4′相关; 提示两组ABX偶合系统的苯环分别和C-1和C-7相连。由此确定了化合物2的平面结构。其相对构型是通过其偶合常数以及计算NMR确定的, 由JH-5/H-6 (2.8 Hz) 推测C-5和C-6两个邻位次甲基片段可能为赤式构型, 同时运用计算NMR的方法, 计算了(5S*, 6S*) 和(5S*, 6R*) 两种构型, 采用R2分析以及DP4+分析发现(5S*, 6S*) 显示出更高的概率99.93%。因此, 化合物2被推断为(5α, 6α)1, 5-epoxy-3-one-6-hydroxy-1, 7-(4-dihydroxy-3-methoxyphenyl)-heptane。
化合物3为白色固体, [α]$ {}_{\mathrm{D}}^{20} $ +17.34 (c 0.01, MeOH), HR-ESI-MS给出准分子离子峰m/z 367.115 5 [M+Na]+, 计算值为367.115 2, 推测分子式为C19H20O6, 不饱和度为10。在1H NMR (CD3OD, 500 MHz) 谱(表1) 中, 有两组ABX偶合系统苯环氢信号[δH 6.81 (1H, d, J = 2.0 Hz, H-2′), 6.78 (1H, d, J = 8.0 Hz, H-5′), 6.77 (1H, d, J = 8.0 Hz, H-2″), 6.76 (1H, dd, J = 8.0, 2.0 Hz, H-6′), 6.70 (1H, d, J = 1.8 Hz, H-5″), 6.61(1H, dd, J = 8.0, 1.8 Hz, H-6″)]。在13C NMR (CD3OD, 125 MHz) 谱中, 除了12个芳碳信号之外, 还有2个亚甲基碳信号[δC 68.1 (C-4), 27.7 (C-3)], 2个次甲基碳信号[δC 51.4 (C-1), 45.1 (C-2)], 1个羰基碳信号δC 181.3 (C-5) 以及2个甲氧基碳信号[δC 56.4 (3′-OCH3), 56.3 (3″-OCH3)]。在1H-1H COSY谱中, H-3a、H-3b与H-2、H-4a、H-4b相关, H-2与H-1、H-3a、H-3b相关。HMBC谱(图2) 中, H-1与C-1′、C-2′、C-6′、C-1″、C-2″、C-6″相关, 提示两个苯环连在C-1位; 根据H-4与C-3、C-2、C-5的HMBC相关信号, 推断出有一个五元内酯环[δC 181.3 (C-5), 68.1 (C-4), 45.1 (C-2), 27.7 (C-3)], 再结合H-1与C-3、C-2、C-5的HMBC相关, 证明内酯环连在C-1位, 最终确定了化合物3的平面结构。通过与文献[13]中芳基丁内酯类化合物noreucol B的旋光值([α]$ {}_{\mathrm{D}}^{20} $ -21.0) 进行对比, 确定化合物3的绝对构型为2S。综上, 确定了化合物3的结构为(2S) 1-(bis(4-hydroxy-3-methoxyphenyl)methyl)-dihydrofuran-5-(2H)one。
化合物4为白色固体, [α]$ {}_{\mathrm{D}}^{20} $ +8.70 (c 0.03, MeOH), 根据HR-ESI-MS显示的准分子离子峰m/z 335.182 3 [M+Na]+, 计算值为335.182 8, 推测分子式为C17H28O5, 不饱和度为4。在1H NMR (CD3OD, 500 MHz) 谱(表2) 中, 芳香区有一个ABX偶合系统的苯环上3个氢质子信号[δH 6.77 (1H, d, J = 1.5 Hz, H-2′), 6.68 (1H, d, J = 8.0 Hz, H-5′), 6.63 (1H, dd, J = 8.0, 1.5 Hz, H-6′)], 1个甲氧基氢信号[δH 3.82 (3H, s, 3′-OCH3)], 3个次甲基氢信号[δH 3.80 (1H, m, H-3), 3.69 (1H, m, H-5), 3.35 (1H, m, H-6)], 6个亚甲基氢信号[δH 2.71, 2.54 (each 1H, m, H-1), 1.74 (2H, m, H-2), 1.63 (2H, m, H-4), 1.53 (2H, m, H-7), 1.48 (2H, m, H-8), 1.43 (2H, m, H-9)] 和1个甲基氢信号[δH 0.92 (3H, t, J = 7.0 Hz, H-10)]。13C NMR谱(CD3OD, 125 MHz) 数据(表2) 共显示出17个碳信号, 包括苯环上6个碳信号[δC 148.8 (C-3′), 145.4 (C-4′), 135.3 (C-1′), 121.8 (C-6′), 116.1 (C-5′), 113.2 (C-2′)], 1个甲氧基碳信号δC 56.3 (3-OCH3), 3个连氧次甲基碳信号[δC 75.9 (C-6), 72.0 (C-5), 68.7 (C-3)], 6个亚甲基碳信号[δC 41.7 (C-4), 41.5 (C-2), 33.6 (C-7), 32.7 (C-1), 29.3 (C-8), 23.8 (C-9)] 和1个末端甲基碳信号δC 14.4 (C-10)。在1H-1H COSY谱中, H-2与H2-1、H-3相关, H-4与H-3、H-5相关, H-6与H-5、H2-7相关, H2-8与H2-7、H2-9相关, H3-10与H2-9相关, 以上信号表明存在一个10碳链。通过HMBC相关分析(图2), H-1与C-2、C-3、C-1′、C-2′、C-6′相关, H-2与C-1′、C-1、C-3相关, 表明3位有羟基取代, 且10碳链连在C-1位; H-5与C-4、C-3、C-6、C-7有HMBC相关, H-6与C-4、C-7、C-8也有HMBC相关, 由此确定了5-OH和6-OH的取代位置。综上确定化合物4的结构为1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 6-triol。
化合物5为无色油状物, [α]$ {}_{\mathrm{D}}^{20} $ +10.04 (c 0.04, MeOH), HR-ESI-MS给出准分子离子峰m/z 319.187 4 [M+Na]+, 推测其分子式为C17H28O4, 不饱和度为4。分析1H NMR (CD3OD, 500 MHz) 数据(表2), 芳香区有3个氢质子信号[δH 6.77 (1H, d, J = 1.5 Hz, H-2′), 6.68 (1H, d, J = 8.0 Hz, H-5′), 6.63 (1H, dd, J = 8.0, 1.5 Hz, H-6′)], 提示有一个ABX偶合系统的苯环, 1个甲氧基氢信号[δH 3.82 (3H, s, 3′-OCH3)], 2个次甲基氢信号[δH 3.52 (1H, m, H-3), 3.42 (1H, m H-8)], 7个亚甲基氢信号[δH 2.70 (2H, m, H-1), 1.71 (2H, m, H-2), 1.47 (4H, m, H-4, H-7), 1.43 (6H, m, H-5, H-6, H-9)] 和1个甲基氢信号[δH 0.92 (3H, t, J = 7.0 Hz, H-10)]。13C NMR (CD3OD, 125 MHz) 谱数据共给出17个碳信号, 包括苯环上6个碳信号[δC 148.8 (C-3′), 145.4 (C-4′), 135.3 (C-1′), 121.8 (C-6′), 116.1 (C-5′), 113.2 (C-2′)], 2个连氧次甲基碳信号[δC 73.8 (C-8), 71.7 (C-3)], 7个亚甲基碳信号[δC 40.7 (C-2), 38.5 (C-4), 37.6 (C-7), 32.6 (C-1), 26.8 (C-5, C-6), 31.0 (C-9)], 1个末端甲基碳信号[δC 10.3 (C-10)]。分析以上数据, 发现化合物5也是一种姜烯酚类化合物, 主要区别在于化合物5仅有2个醇羟基, 且有1个醇羟基的位置与化合物4不同。在1H-1H COSY谱中, H-8与H2-7、H2-9; H-10与H2-9的相关; 结合HMBC谱(图2) 中, 末端甲基上的氢信号(H-10) 与C-9、C-8有相关信号, 推断化合物5的羟基位于C-8位而不是C-5位和C-6位。综上, 确定了化合物5的结构为1-(4-hydroxy-3-methoxyphenyl)-decane-3, 8-diol。
化合物6为无色油状物, [α]$ {}_{\mathrm{D}}^{20} $ +6.80 (c 0.01, MeOH), HR-ESI-MS给出准分子离子峰m/z 335.182 1 [M+Na]+, 计算值为335.182 8, 推测其分子式为C17H28O5, 不饱和度为4。分析1H NMR (CD3OD, 500 MHz) 谱和13C NMR (CD3OD, 125 MHz) 谱数据(表2), 发现化合物6与化合物4相似, 区别在于6-OH移至碳链末端(C-10位), 推断依据是末端甲基的消失以及羟甲基的出现, 同时在HMBC谱(图2) 中H-10与C-8、C-9; H-9与C-10、C-8有相关信号。由此确定化合物6的平面结构为1-(4-hydroxy-3-methoxyphenyl)-decane-3, 5, 10-triol。
实验部分
收起
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); Triple TOF 6600型高效液相色谱-高分辨质谱联用仪(美国AB SCIEX公司); Thermo EVO300紫外分光光度计和Nicolet IS10红外光谱仪(美国Thermo Scientific公司); Rudolph AP-IV型旋光仪(美国Rudolph公司); 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); RE-5210A型旋转蒸发仪(上海亚荣生化仪器厂); N-1100型旋转蒸发仪; EYEL4 CA-1116A型低温冷凝循环泵(东京理化仪器有限公司); 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公司); 正相硅胶色谱填料(青岛海洋化工厂); YMC ODS-A gel (12 nm S-50 μm) 和YMC-Pack ODS-A半制备柱(250 mm × 20 mm; 10 μm; 日本YMC化学工业公司); 色谱纯及分析纯试剂(天津四友精细化学品有限公司)。
干姜(Z. Rhizoma) 购自安徽亳州, 产地为四川省宜宾市, 经河南中医药大学董诚明教授鉴定为姜科植物姜Z. offccinale Rosc.的干燥根茎, 保存于河南中医药大学中药化学提取分离实验室, 标本号: BS631005。
1　提取分离
将干燥的姜根茎(50 kg) 用乙酸乙酯回流提取3次(400 L/1.5 h), 提取后剩余的药渣再用50%乙醇回流提取3次(100 L/2 h)。将3次50%乙醇提取液浓缩后, 将浓缩物上Diaion HP-20大孔吸附树脂, 用水、含水乙醇梯度洗脱并减压浓缩干燥得到10%、30%、50%、70%、95%乙醇5个部位。取50%部位浸膏(80g) 用少量50%乙醇分散后上Diaion HP-20柱, 并用乙醇-水系统(50∶50、60∶40、70∶30、80∶20、95∶5) 进行梯度洗脱, 得到5个部分(Fr.A~Fr.E)。Fr.C (60.0 g) 上MCI Gel CHP-20柱, 依次用甲醇-水(0∶100、30∶70、50∶50、70∶30、95∶5) 梯度洗脱, 得到5个部分(Fr.C.1~Fr.C.5)。Fr.C.3 (25 g) 进一步通过YMC ODS-A gel柱, 以甲醇-水为洗脱剂, 分离得到8个组分(Fr.C.3.1~Fr.C.3.8)。Fr.C.3.2 (3.0 g) 随后经过Sephadex LH-20柱, 依次用甲醇-水梯度洗脱, 得到5个部分(Fr.C.3.2.1~Fr.C.3.2.5)。Fr.C.3.2.2 (55.0 mg) 经半制备高效液相(甲醇-水, 56∶44, 流速3 mL·min-1) 得到化合物4 (tR = 25.12 min, 2.7 mg)。Fr.C.3.2.3 (102.0 mg) 经半制备高效液相色谱(甲醇-水, 52∶48, 流速3 mL·min-1) 得到化合物5 (tR = 28.07 min, 4.0 mg)。Fr.C.3.5 (4.5 g) 经过Sephadex LH-20柱层析, 依次用甲醇-水梯度洗脱, 得到6个部分(Fr.C.3.5.1~Fr.C.3.5.6)。Fr.C.3.5.2 (98.0 mg) 经半制备高效液相色谱(甲醇-水, 42∶58, 流速3 mL·min-1) 得到化合物6 (tR = 23.56 min, 1.4 mg) 和化合物3 (tR = 18.15 min, 1.2 mg)。Fr.C.3.6 (3.4 g) 随后经过Sephadex LH-20柱, 依次用甲醇-水梯度洗脱, 得到5个部分(Fr.C.3.6.1~Fr.C.3.6.5)。Fr.C.3.6.2 (332.0 mg) 经制备/半制备型高效液相色谱(甲醇-水, 52∶48, 流速7和3 mL·min-1) 进行纯化, 得到化合物2 (tR = 30.61 min, 2.7 mg)。Fr.C.4 (20 g) 进一步通过ODS-A gel柱层析, 以甲醇-水为洗脱剂, 分离得到8个组分(Fr.C.4.1~Fr.C.4.8)。Fr.C.4.3 (3.0 g) 随后经过Sephadex LH-20柱, 依次用甲醇-水梯度洗脱, 得到6个部分(Fr.C.4.3.1~Fr.C.4.3.6)。Fr.C.4.3.2 (830.0 mg) 进一步通过制备/半制备型高效液相色谱(流速: 7和3 mL·min-1) 以甲醇-水(66∶34) 进行纯化, 得到化合物1 (tR = 27.42 min, 4.6 mg)。
2　结构鉴定
化合物1为白色固体, [α]$ {}_{\mathrm{D}}^{20} $ -14.62 (c 0.03, MeOH); UV (MeOH) λmax (log ε) nm: 203 (4.93)、265 (4.22); IR (MeOH) vmax: 3 342、2 932、1 711、1 642、1 599、1 515、1 452、1 419、1 367、1 332、1 273、1 237、1 154、1 124、1 032、798 cm-1; HR-ESI-MS m/z 492.225 5 [M+H]+ (计算值为C26H30O5N5, 492.224 1), 1H NMR (CD3OD, 500 MHz) 和13C NMR (CD3OD, 125 MHz) 数据见表1。
化合物2为浅黄色固体, [α]$ {}_{\mathrm{D}}^{20} $ +127.57 (c 0.03, MeOH); UV (MeOH) λmax (log ε) nm: 202 (4.60)、233 (4.04)、334 (4.06); IR (MeOH) vmax: 3 362、2 924、1 572、1 511、1 430、1 378、1 341、1 252、1 203、1 126、1 031、906、801 cm-1; HR-ESI-MS m/z 387.143 5 [M+H]+ (计算值为C21H22O7Na, 387.143 8), 1H NMR (CD3OD, 500 MHz) 和13C NMR (CD3OD, 125 MHz) 数据见表1。
化合物3为白色固体, [α]$ {}_{\mathrm{D}}^{20} $ +17.34 (c 0.01, MeOH); UV (MeOH) λmax (log ε) nm: 203 (4.59)、230 (3.88)、284 (3.62); IR (MeOH) vmax: 3 421、2 931、2 849、1 755、1 680、1 601、1 513、1 452、1 430、1 376、1 266、1 204、1 128、1 026、941、861、805、753、722 cm-1; HR-ESI-MS m/z 367.115 5 [M+Na]+ (计算值为C19H20O6Na, 367.115 2), 1H NMR (CD3OD, 500 MHz) 和13C NMR (CD3OD, 125 MHz) 数据见表1。
化合物4为白色固体, [α]$ {}_{\mathrm{D}}^{20} $ +8.70 (c 0.03, MeOH); UV (MeOH) λmax (log ε) nm: 203 (4.63)、230 (3.89)、282 (3.55); IR (MeOH) vmax: 3 511、3 552、2 935、2 855、1 607、1 516、1 433、1 846、1 278、1 235、1 153、1 092、1 048、1 028、999、936、896、852、829、807、723、631、469、461、433 cm-1; HR-ESI-MS m/z 335.182 3 [M+Na]+ (计算值为C17H28O5Na, 335.182 8), 1H NMR (CD3OD, 500 MHz) 和13C NMR (CD3OD, 125 MHz) 数据见表2。
化合物5为无色油状物, [α]$ {}_{\mathrm{D}}^{20} $ +10.04 (c 0.04, MeOH); UV (MeOH) λmax (log ε) nm: 202 (4.47)、230 (3.67)、282 (3.33); IR (MeOH) vmax: 3 371、2 931、1 515、1 455、1 270、1 152、1 124、1 032、528、510、481、467、438 cm-1; HR-ESI-MS m/z 319.187 4 [M+Na]+ (计算值为C17H28O4Na, 319.187 9), 1H NMR (CD3OD, 500 MHz) 和13C NMR (CD3OD, 125 MHz) 数据见表2。
化合物6为无色油状物, [α]$ {}_{\mathrm{D}}^{20} $ +6.80 (c 0.01, MeOH); UV (MeOH) λmax (log ε) nm: 202 (4.53)、230 (3.78)、282 (3.44); IR (MeOH) vmax: 3 359、2 931、2 856、1 670、1 602、1 515、1 453、1 429、1 271、1 152、1 125、1 032、817 cm-1; HR-ESI-MS m/z 335.182 1 [M+Na]+ (计算值为C17H28O5Na, 335.182 8), 1H NMR (CD3OD, 500 MHz) 和13C NMR (CD3OD, 125 MHz) 数据见表2。
以上6个化合物在确定立体构型时, 发现化合物1~3因样品保存不当不幸遗失或分解导致结构改变, 未能测定ECD, 最终化合物1和3通过旋光度对比的方法确定了绝对构型, 而化合物2仅确定了相对构型未能进一步确定其绝对构型。化合物3~6受限于样品量无法做衍生化如Mosher反应, 其绝对构型也未能确定。

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doi: 10.16438/j.0513-4870.2026-0205
  • 接收时间：2026-02-25
  • 首发时间：2026-09-21
  • 出版时间：2026-07-12
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  • 收稿日期：2026-02-25
  • 修回日期：2026-04-05
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    河南中医药大学药学院, 河南 郑州 450046

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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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