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Article(id=1222469814338183435, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222469808688451726, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2019-0545, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1562688000000, receivedDateStr=2019-07-10, revisedDate=1567699200000, revisedDateStr=2019-09-06, acceptedDate=null, acceptedDateStr=null, onlineDate=1769389116129, onlineDateStr=2026-01-26, pubDate=1576080000000, pubDateStr=2019-12-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1769389116129, onlineIssueDateStr=2026-01-26, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1769389116129, creator=13701087609, updateTime=1769389116129, updator=13701087609, issue=Issue{id=1222469808688451726, tenantId=1146029695717560320, journalId=1189982191388893191, year='2019', volume='54', issue='12', pageStart='2141', pageEnd='2352', issueExtLink='null', onlineDate='null', pubDate='1576080000000', pubDateStr='2019-12-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1769389114782, creator='13701087609', updateTime=1769389604971, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1222471864748859926, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222469808688451726, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1222471864748859927, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222469808688451726, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=2282, endPage=2285, ext={EN=ArticleExt(id=1222469815000883516, articleId=1222469814338183435, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new furocoumarin from the stems of Clausena lansium, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

One undescribed and two known furocoumarins were isolated from the stems of the Clausena lansium through a series of isolation and purification approaches including HPD-100 macroporous resin column, silica gel, reverse phase C18 and so on. Their structures were determined to be 8-[(2S, 3S, 6E)-2, 3-epoxy-3, 7-dimethyl-oct-6-enyloxy] psoralen (1), 8-(7', 8'-epoxygeranyloxy) psoralen (2) and 8-[(2E)-6-oxo-3, 7-dimethyloct-2-enyloxy] psoralen (3) by spectroscopic methods. Compound 1 is a new furocoumarin. Compound 2 showed cytotoxicity to H460 (IC50=43.94 μmol·L-1) and compound 3 showed cytotoxicity to HeLa (33.76 μmol·L-1) through the cytotoxic tests against five human cancer cell lines (H460, H7402, HCT-8, HeLa and MCF-7) for all compounds.

, authors=null, authorsList=Xing-yan SUN, Jie MA, Chuang-jun LI, Ji-wu HUANG, Nan WANG, Cang-jie SHEN, Dong-ming ZHANG, authorCompany=null, correspAuthors=Dong-ming ZHANG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2019 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=1222469815768441193, articleId=1222469814338183435, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=黄皮中的新呋喃香豆素, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用HPD-100大孔树脂柱色谱、硅胶柱色谱、ODS柱色谱等分离纯化方法，从黄皮[Clausena lansium（Lour.）Skeels]中分离得到3个呋喃香豆素化合物，并综合运用波谱学分析方法对化合物进行结构测定。确定其结构分别为：8-[（2S，3S，6E）-2，3-epoxy-3，7-dimethyl-oct-6-enyloxy]psoralen（1）、8-（7'，8'-epoxygeranyloxy）psoralen（2）和8-[（2E）-6-oxo-3，7-dimethyloct-2-enyloxy]psoralen（3）。其中，化合物1为新的呋喃香豆素。对化合物1~3进行肿瘤细胞毒活性测试，结果显示，化合物2对人大细胞肺癌细胞（H460）具有抑制活性（IC50=43.94 μmol·L-1）；化合物3对人宫颈癌细胞（HeLa）具有抑制活性（IC50=33.76 μmol·L-1）。

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*张东明, Tel/Fax:86-10-63165227, E-mail:
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Tetrahedron: Asymmetry, 2014, 25: 591-595., articleTitle=Catalytic asymmetric synthesis of the Colorado potato beetle pheromone and its enantiomer, refAbstract=null), Reference(id=1222469821212648303, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222469814338183435, doi=10.1002/ffj.2730070307, pmid=null, pmcid=null, year=1992, volume=7, issue=null, pageStart=129, pageEnd=139, url=null, language=null, rfNumber=[7], rfOrder=6, authorNames=Ziegler H, Spiteller G, journalName=Flavour Fragr J, refType=null, unstructuredReference= Ziegler H , Spiteller G . Coumarins and psoralens from sicilian lemon oil (Citrus limon (L.) Burm. f.)[J]. Flavour Fragr J, 1992, 7: 129-139., articleTitle=Coumarins and psoralens from sicilian lemon oil (Citrus limon (L.) Burm. f.), refAbstract=null), Reference(id=1222469821397197686, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222469814338183435, doi=10.1248/cpb.46.1939, pmid=null, pmcid=null, year=1998, volume=46, issue=null, pageStart=1939, pageEnd=1940, url=null, language=null, rfNumber=[8], rfOrder=7, authorNames=Kitajima J, Okamura C, Ishikawa T, journalName=Chem Pharm Bull, refType=null, unstructuredReference= Kitajima J , Okamura C , Ishikawa T et al . New glycosides and furocoumarin from the Glenhia littoralis root and rhizoma[J]. Chem Pharm Bull, 1998, 46: 1939-1940., articleTitle=New glycosides and furocoumarin from the Glenhia littoralis root and rhizoma, refAbstract=null), Reference(id=1222469821481083769, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222469814338183435, doi=10.1016/j.phytochem.2019.01.004, pmid=null, pmcid=null, year=2019, volume=160, issue=null, pageStart=48, pageEnd=55, url=null, language=null, rfNumber=[9], rfOrder=8, authorNames=Wang XY, Li CJ, Ma J, journalName=Phytochemistry, refType=null, unstructuredReference= Wang XY , Li CJ , Ma J et al . Cytotoxic 9, 19-cycloartane type triterpenoid glycosides from the roots of Actaea dahurica[J]. 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Compound IC50/μmol·L-1
H460 HeLa
2 43.94 ± 2.17 -
3 - 33.76 ± 7.17
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Cytotoxicity effects of compounds 2 and 3

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Compound IC50/μmol·L-1
H460 HeLa
2 43.94 ± 2.17 -
3 - 33.76 ± 7.17
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Position δH (J in Hz) δC
2 159.7
3 6.46, d (9.6) 114.3
4 8.17, d (9.6) 145.3
4a 116.5
5 7.74, s 114.7
6 125.8
7 147.5
8 130.5
8a 143.0
2' 7.12, s 107.2
3' 8.14, s 148.0
1'' 4.47, dd (11.5, 6.0) 72.1
4.60, dd (11.5, 4.6)
2'' 3.19, m 59.8
3'' 59.9
4'' 1.94, dd, (15.6, 7.8) 23.2
5'' 1.57, m 37.8
1.37, m
6'' 5.05, t (7.2) 123.6
7'' 131.2
8'' 1.61, s 25.5
9'' 1.16, s 16.5
10'' 1.54, s 17.5
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1H NMR (600 MHz) and 13C NMR (150 MHz) data in DMSO-d6 of compound 1

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Position δH (J in Hz) δC
2 159.7
3 6.46, d (9.6) 114.3
4 8.17, d (9.6) 145.3
4a 116.5
5 7.74, s 114.7
6 125.8
7 147.5
8 130.5
8a 143.0
2' 7.12, s 107.2
3' 8.14, s 148.0
1'' 4.47, dd (11.5, 6.0) 72.1
4.60, dd (11.5, 4.6)
2'' 3.19, m 59.8
3'' 59.9
4'' 1.94, dd, (15.6, 7.8) 23.2
5'' 1.57, m 37.8
1.37, m
6'' 5.05, t (7.2) 123.6
7'' 131.2
8'' 1.61, s 25.5
9'' 1.16, s 16.5
10'' 1.54, s 17.5
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黄皮中的新呋喃香豆素
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孙兴妍 , 马洁 , 李创军 , 黄积武 , 王楠 , 沈苍颉 , 张东明 *
药学学报 | 研究论文 2019,54(12): 2282-2285
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药学学报 |研究论文 2019 , 54 (12) : 2282 -2285
黄皮中的新呋喃香豆素
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address=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, bio=null, bioImg=null, bioContent=null, aboutCorrespAuthor=null)}, companyList=[AuthorCompany(id=1222469816007516534, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222469814338183435, xref=null, ext=[AuthorCompanyExt(id=1222469816011710839, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222469814338183435, companyId=1222469816007516534, language=EN, country=null, province=null, city=null, postcode=null, companyName=null, departmentName=null, remark=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), AuthorCompanyExt(id=1222469816015905144, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222469814338183435, companyId=1222469816007516534, language=CN, country=null, province=null, city=null, postcode=null, 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孙兴妍, 马洁, 李创军, 黄积武, 王楠, 沈苍颉, 张东明*
作者信息
  • 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
通讯作者:
*张东明, Tel/Fax:86-10-63165227, E-mail:
A new furocoumarin from the stems of Clausena lansium
Xing-yan SUN, Jie MA, Chuang-jun LI, Ji-wu HUANG, Nan WANG, Cang-jie SHEN, Dong-ming ZHANG*
Affiliations
  • 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
出版时间: 2019-12-12 doi: 10.16438/j.0513-4870.2019-0545
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摘要
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利用HPD-100大孔树脂柱色谱、硅胶柱色谱、ODS柱色谱等分离纯化方法，从黄皮[Clausena lansium（Lour.）Skeels]中分离得到3个呋喃香豆素化合物，并综合运用波谱学分析方法对化合物进行结构测定。确定其结构分别为：8-[（2S，3S，6E）-2，3-epoxy-3，7-dimethyl-oct-6-enyloxy]psoralen（1）、8-（7'，8'-epoxygeranyloxy）psoralen（2）和8-[（2E）-6-oxo-3，7-dimethyloct-2-enyloxy]psoralen（3）。其中，化合物1为新的呋喃香豆素。对化合物1~3进行肿瘤细胞毒活性测试，结果显示，化合物2对人大细胞肺癌细胞（H460）具有抑制活性（IC50=43.94 μmol·L-1）；化合物3对人宫颈癌细胞（HeLa）具有抑制活性（IC50=33.76 μmol·L-1）。

黄皮  /  化学成分  /  呋喃香豆素  /  细胞毒活性

One undescribed and two known furocoumarins were isolated from the stems of the Clausena lansium through a series of isolation and purification approaches including HPD-100 macroporous resin column, silica gel, reverse phase C18 and so on. Their structures were determined to be 8-[(2S, 3S, 6E)-2, 3-epoxy-3, 7-dimethyl-oct-6-enyloxy] psoralen (1), 8-(7', 8'-epoxygeranyloxy) psoralen (2) and 8-[(2E)-6-oxo-3, 7-dimethyloct-2-enyloxy] psoralen (3) by spectroscopic methods. Compound 1 is a new furocoumarin. Compound 2 showed cytotoxicity to H460 (IC50=43.94 μmol·L-1) and compound 3 showed cytotoxicity to HeLa (33.76 μmol·L-1) through the cytotoxic tests against five human cancer cell lines (H460, H7402, HCT-8, HeLa and MCF-7) for all compounds.

Clausena lansium  /  chemical constituents  /  furocoumarin  /  cytotoxicity
孙兴妍, 马洁, 李创军, 黄积武, 王楠, 沈苍颉, 张东明. 黄皮中的新呋喃香豆素. 药学学报, 2019 , 54 (12) : 2282 -2285 . DOI: 10.16438/j.0513-4870.2019-0545
Xing-yan SUN, Jie MA, Chuang-jun LI, Ji-wu HUANG, Nan WANG, Cang-jie SHEN, Dong-ming ZHANG. A new furocoumarin from the stems of Clausena lansium[J]. Acta Pharmaceutica Sinica, 2019 , 54 (12) : 2282 -2285 . DOI: 10.16438/j.0513-4870.2019-0545
正文
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黄皮[Clausena lansium (Lour.) Skeels]为芸香科(Rutaceae)黄皮属(Clausena)小乔木, 主要分布在热带、亚热带地区。其果、叶、根均有药用价值。现代研究表明, 黄皮中的主要化学成分为香豆素、生物碱、萜类、挥发油等, 其活性成分具有抗癌、抗炎、保肝、神经保护等活性[1-4]。本课题组已从黄皮中分离得到生物碱、香豆素、萜类等成分, 部分化合物具有良好生物活性[3-5], 为了进一步寻找黄皮中更多的生物活性成分, 对黄皮的枝条进行化学成分研究, 分离得到3个化合物, 鉴定其结构分别为8-[(2S, 3S, 6E)-2, 3-epoxy-3, 7-dimethyl-oct-6-enyloxy] psoralen (1)、8-(7', 8'-epoxygeranyloxy) psoralen (2)和8-[(2E)-6-oxo-3, 7-dimethyloct-2-enyloxy] psoralen (3)。其中化合物1为新化合物, 结构如图 1所示。化合物2为首次从该属植物中分离得到的化合物, 化合物3为首次从该植物中分离得到的化合物。化合物1~3均进行了对五株肿瘤细胞系(H460、H7402、HCT-8、HeLa、MCF-7)的细胞毒活性筛选实验, 结果显示, 化合物2对H460 (人大细胞肺癌细胞)具有抑制作用(IC50 = 43.94 μmol·L-1); 化合物3对HeLa (人宫颈癌细胞)具有抑制作用(IC50 = 33.76 μmol·L-1)。
结果与讨论
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1 结构鉴定
化合物1  白色粉末。HR-ESI-MS m/z: 355.154 0 [M+H]+ (计算值: 355.154 4), 确定分子式为C21H22O5, 不饱和度为11。1H NMR (600 MHz, DMSO-d6)谱中显示化合物1具有典型的呋喃香豆素母核, δH 6.46 (1H, d, J = 9.6 Hz, H-3)与δH 8.17 (1H, d, J = 9.6 Hz, H-4)为香豆素特征的3, 4位氢信号; δH 7.74 (1H, s, H-5)为苯环质子信号; δH 7.12 (1H, s, H-2')、δH 8.14 (1H, s, H-3')为呋喃环质子信号。此外, δH 5.05 (1H, t, J = 7.2 Hz, H-6'')、δH 1.57 (1H, m, H-5a'')、δH 1.37 (1H, m, H-5b'')以及两甲基信号δH 1.54 (3H, s, H-8'')、δH 1.61 (3H, s, H-10'')提示结构中存在异戊烯基片段。13C NMR (150 MHz, DMSO-d6)谱显示共有21个碳信号, 结合HSQC谱数据分析, 完成了碳氢信号的归属。δH 5.05 (1H, t, J = 7.2 Hz, H-6'')与δC 123.6 (C-6'')直接相关, 说明其为双键信号; δH 4.60 (1H, dd, J = 11.5, 4.6 Hz, H-1''a)和δH 4.47 (1H, dd, J = 11.5, 6.0 Hz, H-1''b)均与δC 72.1 (C-1'')直接相关, 说明其为亚甲氧基信号; δH 3.19 (1H, m, H-2'')与δC 59.8 (C-2'')直接相关, 说明结构中存在次甲氧基; δC 59.9 (C-3'')为连氧季碳信号, 结合分子式推测C-2''和C-3''与同一个氧原子相连, 成三元氧环。1H-1H COSY谱显示, δH 4.60 (1H, dd, J = 11.5, 4.6 Hz, H-1''a)和δH 4.47 (1H, dd, J = 11.5, 6.0 Hz, H-1''b)均与δH 3.19 (1H, m, H-2'')直接相关, 说明亚甲氧基与次甲氧基相连; H-4''与H-5''直接相关, 说明亚甲基与异戊烯基相连。HMBC谱显示, H-1''和C-8存在远程相关, 说明亚甲氧基连接在8位上; 此外, H-9''与C-2''和C-4''均存在远程相关, 说明C-9''与C-3''相连。一维NOE谱显示, 照射H-1''的两个氢, 均出现H-9''的增益, 说明二者位于同侧, 因此最终确定化合物1的平面结构如图 1所示。
化合物1没有Cotton效应, 后经手性柱HPLC进行分析, 显示为单峰。因此, 其绝对构型只能通过与文献数据比对来确定。化合物1的结构与3-methyl-3-(4-methylpent-3-en-1-yl) oxiran-2-yl) methanol相似, 查阅文献[6]得知, 后者绝对构型为(2R, 3R)时, 旋光值为正数{[α]D25+4.5 (c 3.00, CHCl3)}; 绝对构型为(2S, 3S)时, 旋光值为负数{[α]D25-4.2 (c 3.00, CHCl3)}。相同条件下, 化合物1的旋光值为[α]D25-2.2 (c 0.10, CHCl3)。因此, 通过比对文献, 化合物1的绝对构型确定为(2''S, 3''S)。化合物1系统命名为8-[(2S, 3S, 6E)-2, 3-epoxy-3, 7-dimethyl-oct-6-enyloxy] psoralen。
2 细胞毒活性评价
化合物1~3进行了5种肿瘤细胞毒活性筛选实验, 仅化合物2和3表现出抑制作用, 具体数据见表 2。
实验部分
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紫外可见分光光度仪(JASCO V-650型); 旋光测定仪(JASCO P-2000型, 日本); 高效液相色谱仪(Aglient 1100安捷伦科技有限公司); 核磁共振仪(WNMR-I 500、Bruker AVIIIHD 600、VNS-600);中压制备液相色谱系统(Büchi Gradient Former B-687, RP C18), 制备液相色谱仪(LC-6AD, 日本岛津公司); 反相填料(YMC-ODS C18 50 μm, 日本YMC公司); Sephadex LH-20 (美国GE公司); 制备色谱柱(YMC-pack, ODS-A C18, 250 mm×20 mm); 薄层色谱用硅胶GF254和柱色谱用硅胶(100~200、200~300、300~400目, 青岛海洋化工有限公司); HPD-100型大孔树脂(天津海光化工厂有限公司)。色谱纯试剂(美国Fisher公司); 分析纯试剂(北京化工厂)。
药材于2016年10月采自广西省柳州市, 由柳州林业局工程师龙光日鉴定为芸香科(Rutaceae)黄皮属(Clausena)植物黄皮[Clausena lansium (Lour.) Skeels]的枝条部分。
1 提取分离
干燥的黄皮枝条175 kg, 粉碎后用95%乙醇(4倍量)加热回流提取两次, 每次2 h。提取液经减压浓缩得到5.9 kg浸膏, 采用HPD-100吸附树脂柱色谱分离, 依次经过纯水、30%乙醇、60%乙醇、80%乙醇、95%乙醇洗脱, 弃去水部分, 另外4个部分经减压浓缩, 分别得到30%乙醇部分(2.83 kg)、60%乙醇(1.18 kg)、80%乙醇(1.4 kg)、95%乙醇(0.5 kg)。80%乙醇部分(1.4 kg)经硅胶柱色谱(100~200目)分离, 依次经过石油醚、石油醚-二氯甲烷(1:1)、二氯甲烷、乙酸乙酯、95%乙醇洗脱, 得到了6个部分:石油醚部分(Fr1, 16.4 g)、石油醚-二氯甲烷(1:1)部分[Fr2, 138 g; Fr3, 740 g (依据保留体积和薄层色谱结果而区分)]、二氯甲烷部分(Fr4, 162 g)、乙酸乙酯部分(Fr5, 210 g)、95%乙醇部分(Fr6, 290 g)。Fr3 (740 g)经过石油醚-乙酸乙酯(5:1~3:1)梯度洗脱, 每梯度洗脱4个保留体积(9 L/保留体积), 得到12个组分(Fr3.1~3.12)。Fr3.2~Fr3.4均析出大量结晶, 根据薄层色谱分析, 合并Fr2~Fr4的母液(FrA, 105 g)。将组分(FrA, 105 g)使用硅胶柱色谱(200~300目)分离, 经过石油醚-丙酮(10:1、7:1~1:1)、丙酮梯度洗脱, 每梯度洗脱3~4个保留体积(4 L/保留体积)。得到18个组分(FrA.1~A.18), FrA.7 (13 g)通过中压制备液相色谱分离, 以甲醇-水溶液(60%~70%)梯度洗脱, 再经过一系列制备及半制备液相色谱分离得到了化合物1~3。
2 结构鉴定
化合物1   白色粉末。[α]D25-2.2 (c 0.1, CHCl3), UV (MeOH) λmax (logε): 203 (3.38)、217 (3.43)、248 (3.43)、298 (3.12) nm; IR (microscope) νmax: 2 970、2 912、1 762、1 588 cm-1; 1H NMR (600 MHz, DMSO-d6)和13C NMR (150 MHz, DMSO-d6)数据参见表 1。
化合物2   白色粉末。HR-ESI-MS m/z: 355.154 0 [M+H]+ (计算值: 355.153 8), 确定分子式为C21H22O5, 不饱和度为11。1H NMR (600 MHz, DMSO-d6) δ 8.15 (1H, d, J= 9.6 Hz, H-4), 8.12 (1H, s, H-2'), 7.69 (1H, s, H-5), 7.09 (1H, s, H-3'), 6.43 (1H, d, J = 9.6 Hz, H-3), 5.52 (1H, t, J = 7.2 Hz, H-2''), 4.94 (2H, d, J = 7.2 Hz, H-1''), 2.52 (1H, overlapped, H-6''), 2.06 (2H, q, J= 7.2 Hz, H-4''), 1.61 (3H, s, H-8''), 1.44 (2H, q, J = 7.2 Hz, H-5''), 1.16 (3H, s, H-9''), 1.14 (3H, s, H-10'')。13C NMR (150 MHz, DMSO-d6) δ 159.8 (C-2), 114.1 (C-3), 145.3 (C-4), 116.3 (C-4a), 114.3 (C-5), 125.6 (C-6), 147.8 (C-7), 130.3 (C-8), 143.4 (C-8a), 107.1 (C-2'), 147.9 (C-3'), 69.1 (C-1''), 119.6 (C-2''), 142.1 (C-3''), 35.6 (C-4''), 26.7 (C-5''), 62.5 (C-6''), 57.6 (C-7''), 16.1 (C-8''), 24.7 (C-9''), 18.5 (C-10'')。以上数据与文献[7]对照数据一致, 确定该化合物为8-(7', 8'-epoxygeranyloxy) psoralen。
化合物3   白色粉末。HR-ESI-MS m/z: 355.154 0 [M+H]+ (计算值: 355.153 7), 确定分子式为C21H22O5, 不饱和度为11。1H NMR (500 MHz, CDCl3) δ 7.77 (1H, d, J = 9.5 Hz, H-4), 7.69 (1H, s, H-2'), 7.37 (1H, s, H-5), 6.82 (1H, s, H-3'), 6.37 (1H, d, J = 9.5 Hz, H-3), 5.60 (1H, s, H-2''), 5.01 (2H, d, J = 5.5 Hz, H-1''), 2.56 (1H, overlapped, H-6''), 2.27 (2H, m, H-5''), 1.09 (3H, s, H-9''), 1.07 (3H, s, H-10'')。13C NMR (125 MHz, CDCl3) δ: 160.5 (C-2), 114.7 (C-3), 144.4 (C-4), 116.5 (C-4a), 113.3 (C-5), 125.9 (C-6), 148.7 (C-7), 131.5 (C-8), 143.9 (C-8a), 106.8 (C-2'), 146.6 (C-3'), 70.0 (C-1''), 119.7 (C-2''), 142.0 (C-3''), 33.1 (C-4''), 38.4 (C-5''), 214.0 (C-6''), 40.9 (C-7''), 16.8 (C-8''), 18.3 (C-9''), 18.3 (C-10'')。以上数据与文献[8]对照数据一致, 确定该化合物为8-[(2E)-6-oxo-3, 7-dimethyloct-2-enyloxy] psoralen。
3 细胞毒实验
采用MTT比色法对化合物1~3进行细胞毒活性测试, 所用肿瘤细胞株如下:人大细胞肺癌细胞H460、人肝癌细胞H7402、人结肠癌细胞HCT-8、人宫颈癌细胞HeLa以及人乳腺癌细胞MCF-7。具体实验方法参见文献[9]。
基金
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  • 北京市自然科学基金青年项目(7194299)
  • 国家自然科学基金资助项目(NNSFC81730093)
文献
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参考文献 引证文献
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2019年第54卷第12期
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doi: 10.16438/j.0513-4870.2019-0545
  • 接收时间：2019-07-10
  • 首发时间：2026-01-26
  • 出版时间：2019-12-12
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  • 收稿日期：2019-07-10
  • 修回日期：2019-09-06
基金
北京市自然科学基金青年项目(7194299)
国家自然科学基金资助项目(NNSFC81730093)
作者信息
    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

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*张东明, Tel/Fax: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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