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Article(id=1222469813088276730, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222469808688451726, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2019-0618, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1564588800000, receivedDateStr=2019-08-01, revisedDate=1567785600000, revisedDateStr=2019-09-07, acceptedDate=null, acceptedDateStr=null, onlineDate=1769389115831, onlineDateStr=2026-01-26, pubDate=1576080000000, pubDateStr=2019-12-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1769389115831, onlineIssueDateStr=2026-01-26, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1769389115830, creator=13701087609, updateTime=1769389115830, 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=2286, endPage=2288, ext={EN=ArticleExt(id=1222469813755171106, articleId=1222469813088276730, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new 2, 3-dioxoflavonoid from the aerial part of Hypericum perforatum, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Phytochemical study of the aerial parts of Hypericum perforatum L. resulted in the isolation of an undescribed compound, which was identified as Rel-(2S, 3R)-2-(3, 4-dihydroxyphenyl)-3, 5, 7-trihydroxy-2-methoxy-3-(2-oxopropyl)chroman-4-one (1) by spectroscopic methods including UV, IR, HR-ESI-MS, 1D and 2D NMR spectra. Compound 1 is a new 2, 3-dioxo-flavone with an acetonyl moiety, rarely found in nature. In addition, a plausible biogenetic pathway of 1 was proposed in this article.

, authors=null, authorsList=Jie MA, Teng-fei JI, Jin TIAN, Yan-gai WANG, Jian-bo YANG, Ya-lun SU, Ai-guo WANG, authorCompany=null, correspAuthors=Ai-guo WANG, 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=1222469814552088917, articleId=1222469813088276730, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=贯叶金丝桃中一个新的2, 3-二氧代黄酮, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用硅胶柱色谱、Sephedax LH-20、制备高效液相色谱等分离、纯化方法，从贯叶金丝桃（Hypericum perforatum L.）中分离得到一个新的黄酮类化合物，其结构经UV、IR、MS、HR-ESI-MS及核磁共振等波谱技术鉴定为：Rel-（2S，3R）-2-（3，4-dihydroxyphenyl）-3，5，7-trihydroxy-2-methoxy-3-（2-oxopropyl）chroman-4-one（1）。化合物1是一个含有一个丙酮基的2，3-二氧代黄酮类化合物，在自然界中较为罕见。此外，还对该化合物的可能生源途径进行了推测。

, authors=null, authorsList=马洁, 吉腾飞, 田晋, 王彦改, 杨建波, 苏亚伦, 王爱国, authorCompany=null, correspAuthors=王爱国, authorNote=null, correspAuthorsNote=
*王爱国, Tel/Fax:86-10-63165327, E-mail:
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Position Type δC δH (J, Hz)
1
2 C 109.1
3 C 79.5
4 C 198.8
5 C 164.0
6 CH 97.7 6.05 (d, 2.1)
7 C 167.4
8 CH 96.9 6.13 (d, 2.1)
9 C 158.5
10 C 101.6
11 CH3 51.2 2.98 s
12 CH2 48.4 2.63 (d, 13.8, Ha)
2.47 (d, 13.8, Hb)
13 C 206.2
14 CH3 32.2 1.99 s
1' C 126.1
2' CH 115.4 7.22 (d, 2.0)
3' C 147.0
4' C 145.3
5' CH 116.8 6.91 (d, 8.4)
6' CH 121.4 7.12 (dd, 8.4, 2.0)
5-OH 11.17
3-OH 4.93
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1H NMR (300 MHz) and 13C NMR (100 MHz) data for 1 in Me2CO-d6

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Position Type δC δH (J, Hz)
1
2 C 109.1
3 C 79.5
4 C 198.8
5 C 164.0
6 CH 97.7 6.05 (d, 2.1)
7 C 167.4
8 CH 96.9 6.13 (d, 2.1)
9 C 158.5
10 C 101.6
11 CH3 51.2 2.98 s
12 CH2 48.4 2.63 (d, 13.8, Ha)
2.47 (d, 13.8, Hb)
13 C 206.2
14 CH3 32.2 1.99 s
1' C 126.1
2' CH 115.4 7.22 (d, 2.0)
3' C 147.0
4' C 145.3
5' CH 116.8 6.91 (d, 8.4)
6' CH 121.4 7.12 (dd, 8.4, 2.0)
5-OH 11.17
3-OH 4.93
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贯叶金丝桃中一个新的2, 3-二氧代黄酮
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马洁 , 吉腾飞 , 田晋 , 王彦改 , 杨建波 , 苏亚伦 , 王爱国 *
药学学报 | 研究论文 2019,54(12): 2286-2288
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药学学报 |研究论文 2019 , 54 (12) : 2286 -2288
贯叶金丝桃中一个新的2, 3-二氧代黄酮
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马洁, 吉腾飞, 田晋, 王彦改, 杨建波, 苏亚伦, 王爱国*
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:
*王爱国, Tel/Fax:86-10-63165327, E-mail:
A new 2, 3-dioxoflavonoid from the aerial part of Hypericum perforatum
Jie MA, Teng-fei JI, Jin TIAN, Yan-gai WANG, Jian-bo YANG, Ya-lun SU, Ai-guo WANG*
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.0513-4870.2019-0618
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利用硅胶柱色谱、Sephedax LH-20、制备高效液相色谱等分离、纯化方法，从贯叶金丝桃（Hypericum perforatum L.）中分离得到一个新的黄酮类化合物，其结构经UV、IR、MS、HR-ESI-MS及核磁共振等波谱技术鉴定为：Rel-（2S，3R）-2-（3，4-dihydroxyphenyl）-3，5，7-trihydroxy-2-methoxy-3-（2-oxopropyl）chroman-4-one（1）。化合物1是一个含有一个丙酮基的2，3-二氧代黄酮类化合物，在自然界中较为罕见。此外，还对该化合物的可能生源途径进行了推测。

贯叶金丝桃  /  化学成分  /  2, 3-二氧代黄酮

Phytochemical study of the aerial parts of Hypericum perforatum L. resulted in the isolation of an undescribed compound, which was identified as Rel-(2S, 3R)-2-(3, 4-dihydroxyphenyl)-3, 5, 7-trihydroxy-2-methoxy-3-(2-oxopropyl)chroman-4-one (1) by spectroscopic methods including UV, IR, HR-ESI-MS, 1D and 2D NMR spectra. Compound 1 is a new 2, 3-dioxo-flavone with an acetonyl moiety, rarely found in nature. In addition, a plausible biogenetic pathway of 1 was proposed in this article.

Hypericum perforatum  /  chemical constituents  /  2, 3-dioxoflavone
马洁, 吉腾飞, 田晋, 王彦改, 杨建波, 苏亚伦, 王爱国. 贯叶金丝桃中一个新的2, 3-二氧代黄酮. 药学学报, 2019 , 54 (12) : 2286 -2288 . DOI: 10.16438/j.0513-4870.2019-0618
Jie MA, Teng-fei JI, Jin TIAN, Yan-gai WANG, Jian-bo YANG, Ya-lun SU, Ai-guo WANG. A new 2, 3-dioxoflavonoid from the aerial part of Hypericum perforatum[J]. Acta Pharmaceutica Sinica, 2019 , 54 (12) : 2286 -2288 . DOI: 10.16438/j.0513-4870.2019-0618
正文
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贯叶金丝桃Hypericum perforatum L.为藤黄科金丝桃属多年生草本植物, 又名贯叶连翘、圣约翰逊草[1]。我国贯叶金丝桃资源十分丰富, 有55种、8个亚种, 分布于甘肃、陕西、四川、安徽、贵州、河南、湖北等地[2]。2005年中国药典收录其中[3]。贯叶金丝桃中的化学成分主要包括黄酮类、间苯三酚类及萘骈二蒽酮类等, 具有抗乙肝病毒、抗AIDS、抗菌、伤口愈合及治疗轻中度抑郁等广泛活性[4]。在欧洲用于治疗轻中度抑郁, 已有数百年历史。其开发应用在国际上引起了广泛关注, 现在对该植物的研究仍然是热点之一。前期研究已从中分离得到多个黄酮及酚酸类化合物[5], 为了进一步寻找和明确该植物中的活性成分, 本文采用硅胶柱色谱、凝胶色谱及制备液相色谱等多种分离技术从贯叶金丝桃地上部分的95%乙醇提取物中分离得到1个新的较罕见的2, 3-二氧代黄酮类化合物。通过UV、IR、MS、HR-ESI-MS及核磁共振等波谱技术鉴定为: Rel-(2S, 3R)-2-(3, 4-dihydroxyphenyl)-3, 5, 7-trihydroxy-2-methoxy-3-(2-oxopropyl)chroman-4-one (图 1)。结构中含有一个丙酮基片段, 在自然界中较为罕见存在。此外, 还对化合物1的可能生源途径进行了推测(图 2)。
结构解析
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化合物1
淡黄色固体。正离子ESI-MS在m/z 391.1处给出了[M+H]+峰, 413.2处给出了[M+Na]+峰, 负离子ESI-MS在m/z 389.2处给出了[M-H]-峰, 以及779.2处的[2M-H]-峰, 提示分子量为390, HR-ESI-MS给出了准分子离子峰m/z: 413.083 8 [M+Na]+, (计算值为413.084 3, C19H18NaO9), 确定分子式为C19H18O9, 不饱和度为11。IR光谱给出了羰基(1 637、1 701 cm-1), 苯环(1 511、1 471 cm-1)的特征吸收峰。紫外光谱显示UV (MeOH) λmax (logε): 209 (3.75)、290 (3.47)、331 (2.94) nm。提示该化合物属于黄酮类结构骨架。
在1H NMR谱中, 低场区显示一组ABX系统质子信号[δH 7.22 (1H, d, J = 2.0 Hz, H-2')、7.12 (1H, dd, J = 8.4, 2.0 Hz, H-6')、6.91 (1H, d, J = 8.4 Hz, H-5')], 一组AB自旋质子信号[δH 6.13 (1H, d, J = 2.1 Hz, H-8)、6.05 (1H, d, J = 2.1 Hz, H-6)], 4个活泼羟基信号(δH 11.17、9.92、8.27、8.11), 一个羟基信号δH 4.93, 2个甲基信号δH 2.98 (3H, s, H3-11)、1.99 (3H, s, H3-14), 两个偕偶AB偶合特征质子信号[δH 2.63 (1H, d, J = 13.8 Hz, 12-Ha)和2.47 (1H, d, J = 13.8 Hz, 12-Hb)]。
13C NMR谱中, 显示了18个碳信号, DEPT谱将这些碳信号区分为2个甲基(1个连氧甲基碳, 1个与酮羰基相连碳)、1个亚甲基、5个次甲基(均为sp2杂化碳)和11个季碳(包括7个sp2杂化碳, 1个羰基碳)。根据以上数据, 推断化合物1为黄酮类化合物。
1H NMR谱中特征的AB自旋质子信号说明A环为5, 7-二羟基取代, ABX系统质子信号提示B环为3', 4'-二取代。AB自旋质子信号准确归属[δH 6.13 (H-8), 6.05 (H-6)]。并且在HMBC图谱中, H-6与C-8、C-10, H-8与C-6、C-10相关, H-2'与C-4'、C-6', H-5'与C-1'、C-3', H-6'与C-2'、C-5'的远程相关进一步得到证实。H3-14与C-13相关, 同时结合化学位移说明C-14连在C-13上; H2-12与C-13、H3-14与C-12相关表明C-13所在的乙酰基与C-12相连; 同时H2-12还与C-2、C-4、C-13相关, 3-OH与C-2、C-3、C-4、C-12相关提示C-12连在季碳C-3上; 甲氧基H3-11仅与C-2相关说明C-11所在的甲氧基与C-2相连; 最后通过H-2'与C-2相关确定了B环芳香环连接在C-2上。这样化合物1的平面结构就确定了, 如图 1所示。
在化合物1的NOESY谱中, H2-12与H-2'、H-6'相关, 表明H2-12和B环处于母核结构的同侧, 推测连在C-2的甲氧基和连在C-3位的羟基处于母核结构的另外一侧。由此, 确定其相对构型如图所示。[α]D20≈0 (c 0. 2, MeOH), 结合ECD谱, 未出现明显的Cotton吸收, 推测可能为一对对映异构体。但是因为分离的量较少无法进行手性拆分。故最后确定化合物1的结构为Rel-(2S, 3R)-2-(3, 4-dihydroxyphenyl)-3, 5, 7-trihydroxy-2-methoxy-3-(2-oxopropyl)chroman-4-one。
对化合物1的生源途径进行了推测[6]:前体化合物是在贯叶金丝桃中已经分离到的含量丰富的槲皮素(quercetin), 通过迈克尔加成反应得到醌类中间体1a, 再经过甲基转移酶获得甲基化的中间体1b, 然后和乙酰辅酶A经过亲核反应生成1c, 再经与丙二酸单酰辅酶A缩合等途径得到乙酰乙酸类中间体1d。1d通过分子内的消除, 生成一分子的CO2后得到烯醇类中间体1e, 最后通过烯醇转化得到最终产物1。
实验部分
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Agilent1100系列LC/MSD Trap-SL型质谱仪(Agilent, Waldbronn, Germany); QSTAR Elite四极杆-飞行时间质谱仪(AB SCIEX, USA)测定质谱; Mercury-300、Mercury-400和SYS-600核磁共振仪(美国Varian公司)测定NMR; 测定温度: 297 K, 以溶剂峰信号作为内标; JASCO P2000自动数码旋光仪(JASCO, Tokyo, Japan)测定旋光; JASCO V-650分光光度计测定UV (JASCO); Nicolet 5700傅里叶变换红外光谱仪(显微透射法)测定IR (Thermo Electron, Madison, WI, USA); 薄层色谱硅胶GF254和柱色谱用硅胶(100~200目, 200~300目)均为青岛海洋化工厂产品; 葡聚糖凝胶Sephadex LH-20为Pharmacia公司产品; Agilent 1100和Shimadzu LC-6AD高效液相色谱仪(YMC公司Pack ODS-A C18制备柱, 20 mm×250 mm, 5 µm); 所用分析纯和色谱纯试剂为北京化工厂生产。
贯叶金丝桃全草于2008年采自新疆维吾尔自治区乌孙山, 经新疆药物所刘发教授鉴定为贯叶金丝桃Hypericum perforatum L., 标本现存于中国医学科学院药物研究所植物标本室, 标本号为No. ID-S-2250。
1 提取分离
干燥的贯叶金丝桃地上部分20 kg, 粉碎后用10倍量的95%乙醇加热回流提取3次, 每次2 h, 提取液减压回收溶剂得浸膏3.5 kg。将浸膏分散于10 L水中混悬, 过滤后得到水溶(HP-W)和水不溶(HP-WN)两部分。水不溶部位(170 g)经硅胶柱(200~300目, 400 g)色谱分离, 依次用石油醚、乙酸乙酯、丙酮和甲醇洗脱, 回收溶剂得到相应的洗脱部分(HP-PE, HP-EtOAc, HP-A, HP-MeOH)。HP-EtOAc (50 g)经硅胶柱色谱(200~300目, 1000 g)石油醚-丙酮为洗脱剂进行梯度洗脱, 得到41个组分(HPE1-HPE41)。组分HPE30 (4 g)通过Sephadex LH-20柱色谱, 石油醚-氯仿-甲醇(5:5:1)为洗脱剂得到10个亚组分(HPE30a-HE30j)。HPE30h部分(260 mg)分离纯化, 通过HPLC制备(YMC, 甲醇-水=55:45, 7 mL·min-1, λ= 254 nm)分离得到化合物1 (3 mg)。
2 结构鉴定
化合物1 淡黄色固体。UV (MeOH) λmax (logε): 209 (3.75)、290 (3.47)、331 (2.94) nm; IR νmax 3 354 (br s)、1 701、1 637、1 511、1 471、1 293、1 163、829、784 cm-1; 1H NMR (CD3COCD3, 300 MHz) and 13C NMR (CD3COCD3, 100 MHz)见表 1; (+)-ESI-MS m/z 391.1 [M+H]+, 413.2 [M+Na]+, (-)-ESI-MS m/z 389.2 [M-H]-, 779.2 [2M-H]-; 分子式为C19H18O9; (+)-HR-ESI-MS m/z: 413.083 8 [M+Na]+ (计算值413.084 3, C19H18NaO9)。
基金
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  • 北京市自然科学基金青年项目(7194299)
  • 中国医学科学院医学与健康科技创新工程(CAMS-I2M-1-010)
文献
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参考文献 引证文献
排序方式：
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Editorial Committee of Flora of China . Flora of China (中国植物志)[M]. Beijing, Science Press, 1990, 21.
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Xie ZW , Yu YQ . Name of Chinese Herbal Medicine (全国中草药名鉴上册)[M]. Beijing, People's Medical Publishing House, 1996, 350.
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Barnes J , Anderson LA , Phillipson JD . St John's wort (Hypericum perforatum L.): a review of its chemistry, pharmacology and clinical properties[J]. J Pharm Pharmacol, 2001, 53: 583-600.
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Ma J , Yang JB , Ji TF et al . Chemical constituents from Hypericum perforatum[J]. China J Chin Mater Med (中国中药杂志), 2012, 37: 2408-2412. http://d.old.wanfangdata.com.cn/Periodical/zgyaokdxxb200204005
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Dewick PM. Medicinal Natural Products: A Biosynthetic Approach[M]. 3rd Ed. Chichester: John Wiley and Sons, 2009.
2019年第54卷第12期
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doi: 10.16438/j.0513-4870.2019-0618
  • 接收时间：2019-08-01
  • 首发时间：2026-01-26
  • 出版时间：2019-12-12
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  • 收稿日期：2019-08-01
  • 修回日期：2019-09-07
基金
北京市自然科学基金青年项目(7194299)
中国医学科学院医学与健康科技创新工程(CAMS-I2M-1-010)
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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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
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