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Article(id=1222469815827157424, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1222469808688451726, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2019-0535, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1562515200000, receivedDateStr=2019-07-08, revisedDate=1567785600000, revisedDateStr=2019-09-07, acceptedDate=null, acceptedDateStr=null, onlineDate=1769389116484, onlineDateStr=2026-01-26, pubDate=1576080000000, pubDateStr=2019-12-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1769389116484, onlineIssueDateStr=2026-01-26, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1769389116484, creator=13701087609, updateTime=1769389116484, 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=2277, endPage=2281, ext={EN=ArticleExt(id=1222469816422748636, articleId=1222469815827157424, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new sesquiterpene glycoside from Osmanthus fragrans var. aurantiacus, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

The chemical constituents were isolated and purified by column chromatography and semi-preparative reversed-phase high performance liquid chromatography with silica gel, MCI and polyamide in order to study the chemical constituents of dried flowers of Osmanthus fragrans var. aurantiacus. Their structures were identified by the physical and chemical properties and one-dimensional nuclear magnetic resonance (1H-, 13C-NMR, DEPT), two-dimensional nuclear magnetic resonance (1H-1H COSY, non-decoupled HSQC, HSQC, HMBC), UV, IR and high resolution mass spectrometry data. One new compound (1) and five known compounds (2-6) were isolated from 95% ethanol extract of dried broccoli. They were identified as (9S)-9-hydroxymengastigm-5-en-4-one-9-O-primeveroside (1), oleanolic acid (2), forsythiaside (3), 2-(4-hydroxyphenethyl)-ethanol-(6-acetyl)-β-D-glucopyranoside (4), salidroside (5), and acteoside (6). Compounds (2-6) were isolated from this plant for the first time.

, authors=null, authorsList=Hong-yu JIANG, Si-yu ZHONG, Li-ping WU, Ya-rui YU, Shi-hui LU, Ling-rui LI, Cheng-rong LI, Meng-qi AN, Jing HUANG, authorCompany=null, correspAuthors=Jing HUANG, 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=1222469817135780375, articleId=1222469815827157424, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=丹桂中的一个新降倍半萜苷, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

为了对丹桂（Osmanthus fragrans var.aurantiacus）干花进行化学成分研究，利用硅胶、MCI、聚酰胺等柱色谱和半制备反相高效液相色谱从丹桂干花95%乙醇提取物中分离得到1个新化合物（1）和5个已知化合物（2~6），通过理化性质和一维核磁共振（1H-、13C-NMR、DEPT）、二维核磁共振（1H-1H COSY、非去偶HSQC、HSQC、HMBC）、紫外光谱、红外光谱以及高分辨质谱等波谱数据鉴定化合物结构，分别鉴定为（9S）-9-hydroxymengastigm-5-en-4-one-9-O-primeveroside（1）、齐墩果酸（2）、连翘脂素（3）、红景天苷酯（4）、红景天苷（5）和类叶升麻苷（6）。化合物1为新化合物，其他化合物均为首次从该植物中分离得到。

, authors=null, authorsList=江虹雨, 钟思雨, 吴利苹, 俞雅芮, 陆世惠, 李玲蕊, 李成容, 安梦琪, 黄静, authorCompany=null, correspAuthors=黄静, authorNote=null, correspAuthorsNote=
*黄静, Tel:86-28-85503045, E-mail:
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Position δC δH (J in Hz)
1 37.8 -
2 38.6 1.78 (t, 6.8)
3 35.2 2.41 (t, 6.8)
4 201.7 -
5 131.8 -
6 168.7 -
7 27.8 2.26 (m), 2.51 (m)
8 36.7 1.64 (m)
9 77.9 3.89 (sextet)
10 22.2 1.27 (d, 6.4)
11 27.4 1.17 (s)
12 27.4 1.17 (s)
13 12.0 1.73 (s)
Glc-1' 104.4 4.34 (d, 8.0)
Glc-2' 75.4 3.17 (m)
Glc-3' 78.3 3.31 (m)
Glc-4' 71.6 3.41 (m)
Glc-5' 77.1 3.42 (m)
Glc-6' 69.9 3.71 (dd, 11.6, 6.0)
4.03 (dd, 11.6, 2.4)
Xyl-1'' 105.7 4.32 (d, 7.6)
Xyl-2'' 75.0 3.17 (m)
Xyl-3'' 77.8 3.28 (m)
Xyl-4'' 71.3 3.47 (m)
Xyl-5'' 67.1 3.16 (m)
3.83 (dd, 11.2, 5.2)
), ArticleFig(id=1222469822068282216, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1222469815827157424, language=CN, label=Table 1, caption=

1H (400 MHz) and 13C NMR (100 MHz) data of 1 in methanol-d4

, figureFileSmall=null, figureFileBig=null, tableContent=
Position δC δH (J in Hz)
1 37.8 -
2 38.6 1.78 (t, 6.8)
3 35.2 2.41 (t, 6.8)
4 201.7 -
5 131.8 -
6 168.7 -
7 27.8 2.26 (m), 2.51 (m)
8 36.7 1.64 (m)
9 77.9 3.89 (sextet)
10 22.2 1.27 (d, 6.4)
11 27.4 1.17 (s)
12 27.4 1.17 (s)
13 12.0 1.73 (s)
Glc-1' 104.4 4.34 (d, 8.0)
Glc-2' 75.4 3.17 (m)
Glc-3' 78.3 3.31 (m)
Glc-4' 71.6 3.41 (m)
Glc-5' 77.1 3.42 (m)
Glc-6' 69.9 3.71 (dd, 11.6, 6.0)
4.03 (dd, 11.6, 2.4)
Xyl-1'' 105.7 4.32 (d, 7.6)
Xyl-2'' 75.0 3.17 (m)
Xyl-3'' 77.8 3.28 (m)
Xyl-4'' 71.3 3.47 (m)
Xyl-5'' 67.1 3.16 (m)
3.83 (dd, 11.2, 5.2)
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丹桂中的一个新降倍半萜苷
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江虹雨 , 钟思雨 , 吴利苹 , 俞雅芮 , 陆世惠 , 李玲蕊 , 李成容 , 安梦琪 , 黄静 *
药学学报 | 研究论文 2019,54(12): 2277-2281
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药学学报 |研究论文 2019 , 54 (12) : 2277 -2281
丹桂中的一个新降倍半萜苷
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江虹雨, 钟思雨, 吴利苹, 俞雅芮, 陆世惠, 李玲蕊, 李成容, 安梦琪, 黄静*
作者信息
  • 四川大学华西药学院, 四川 成都 610041
通讯作者:
*黄静, Tel:86-28-85503045, E-mail:
A new sesquiterpene glycoside from Osmanthus fragrans var. aurantiacus
Hong-yu JIANG, Si-yu ZHONG, Li-ping WU, Ya-rui YU, Shi-hui LU, Ling-rui LI, Cheng-rong LI, Meng-qi AN, Jing HUANG*
Affiliations
  • West China School of Pharmacy, Sichuan University, Chengdu 610041, China
出版时间: 2019-12-12 doi: 10.16438/j.0513-4870.2019-0535
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摘要
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为了对丹桂（Osmanthus fragrans var.aurantiacus）干花进行化学成分研究，利用硅胶、MCI、聚酰胺等柱色谱和半制备反相高效液相色谱从丹桂干花95%乙醇提取物中分离得到1个新化合物（1）和5个已知化合物（2~6），通过理化性质和一维核磁共振（1H-、13C-NMR、DEPT）、二维核磁共振（1H-1H COSY、非去偶HSQC、HSQC、HMBC）、紫外光谱、红外光谱以及高分辨质谱等波谱数据鉴定化合物结构，分别鉴定为（9S）-9-hydroxymengastigm-5-en-4-one-9-O-primeveroside（1）、齐墩果酸（2）、连翘脂素（3）、红景天苷酯（4）、红景天苷（5）和类叶升麻苷（6）。化合物1为新化合物，其他化合物均为首次从该植物中分离得到。

木犀科  /  桂花  /  丹桂  /  降倍半萜苷

The chemical constituents were isolated and purified by column chromatography and semi-preparative reversed-phase high performance liquid chromatography with silica gel, MCI and polyamide in order to study the chemical constituents of dried flowers of Osmanthus fragrans var. aurantiacus. Their structures were identified by the physical and chemical properties and one-dimensional nuclear magnetic resonance (1H-, 13C-NMR, DEPT), two-dimensional nuclear magnetic resonance (1H-1H COSY, non-decoupled HSQC, HSQC, HMBC), UV, IR and high resolution mass spectrometry data. One new compound (1) and five known compounds (2-6) were isolated from 95% ethanol extract of dried broccoli. They were identified as (9S)-9-hydroxymengastigm-5-en-4-one-9-O-primeveroside (1), oleanolic acid (2), forsythiaside (3), 2-(4-hydroxyphenethyl)-ethanol-(6-acetyl)-β-D-glucopyranoside (4), salidroside (5), and acteoside (6). Compounds (2-6) were isolated from this plant for the first time.

Oleaceae  /  Osmanthus fragrans  /  Osmanthus fragrans var. aurantiacus  /  sesquiterpene glycoside
江虹雨, 钟思雨, 吴利苹, 俞雅芮, 陆世惠, 李玲蕊, 李成容, 安梦琪, 黄静. 丹桂中的一个新降倍半萜苷. 药学学报, 2019 , 54 (12) : 2277 -2281 . DOI: 10.16438/j.0513-4870.2019-0535
Hong-yu JIANG, Si-yu ZHONG, Li-ping WU, Ya-rui YU, Shi-hui LU, Ling-rui LI, Cheng-rong LI, Meng-qi AN, Jing HUANG. A new sesquiterpene glycoside from Osmanthus fragrans var. aurantiacus[J]. Acta Pharmaceutica Sinica, 2019 , 54 (12) : 2277 -2281 . DOI: 10.16438/j.0513-4870.2019-0535
正文
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木犀科(Oleaceae)木犀属(Osmanthus)植物全世界共有30种, 主要分布于亚洲东部和北美洲东南部。桂花(Osmanthus fragrans)属于木犀属植物, 主要分布在我国大陆长江以南地区, 故我国是桂花的分布中心。桂花是深受我国人民喜爱的一种观赏性植物, 被评为中国十大名花。经过上千年的引种和人工培育, 桂花已经形成了多达上百个品种。根据桂花的开花季节以及花色, 桂花被分为金桂、银桂、丹桂和四季桂等4个品种群[1]。除观赏外, 桂花还被用于制作风味食品以及被用于化妆品。近年来, 对桂花的化学成分及药理活性有一些研究, 结果发现桂花中含有木脂素、苯丙素和环烯醚萜等类型的成分[2, 3], 其中一些成分显示有抗氧化、抑制β-分泌酶或NO释放等活性[4-6]。丹桂(Osmanthus fragrans var. aurantiacus)为桂花的一个变种, 其花色呈丹红色, 是桂花各品种中花色最深的品种, 是丹桂品种群的代表品种。本课题组长期对不同品种桂花、不同部位等开展化学成分及药理活性研究[7-10]。由于丹桂的资源非常丰富, 为了进一步开发丹桂资源, 同时, 为了发现丹桂中的活性成分, 课题组对丹桂干花进行了较为系统的化学成分研究。结果从丹桂干花的95%乙醇提取物中分离并鉴定了6个成分(1~6), 其中1为新化合物, 所有化合物均为首次从丹桂中得到(图 1)。
结果与讨论
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化合物1:无固形粉末, Molish反应呈阳性; [α] -27.3 (c 0.116, MeOH); mp 115.5~120.0 ℃; 紫外光谱λmaxMeOH nm (logε): 250 (2.81);红外光谱νmaxnear cm-1: 3 363 (-OH)、2 923 (-CH2-)、1 645 (C=O)、1 421 (C=C), 提示1中含有羟基、羰基和双键。HR-ESI-MS显示1的准分子离子峰m/z 527.246 8 [M+Na]+, (计算值527.246 8), 确定1的分子式为C24H40O11, 不饱和度Ω = 5。
1的1H NMR谱中显示了4个甲基信号δΗ 1.17 (6H, s), 1.73 (3H, s), 1.27 (3H, d, J = 6.4 Hz); 4个亚甲基信号δΗ 1.64 (2H, m), 1.78 (2H, t, J = 6.8 Hz), 2.41 (2H, t, J = 6.8 Hz), 2.26、2.51 (2H, m); 2个糖的端基氢信号δΗ 4.32 (1H, d, J = 7.6 Hz)和4.34 (1H, d, J = 8.0 Hz)。1的13C NMR谱、DEPT谱、结合HSQC显示13个苷元碳信号, 包括4个甲基碳信号δC 12.0、22.2、27.4和27.4; 4个亚甲基碳信号δC 27.8、35.2、36.7和38.6; 10个含氧取代叔碳信号δC 78.3、77.9、77.8、77.1、75.4、75.0、71.6、71.3、69.9、67.1; 1个季碳信号δC 37.8, 1个酮羰基碳信号δC 201.7, 以及2个烯碳信号δC 131.8、168.7; 2个糖的端基碳信号δC 104.4和105.7。上述1H、13C NMR数据提示1可能为含有两个单糖基的苷类化合物。
将1的1H、13C NMR数据与文献对照, 发现1与(9R)- 9-hydroxymengastigman-5-en-4-one-9-O-primeveroside (A)[11]的NMR数据相似。进一步比较两者的NMR数据, 发现1的C-8 (δC 36.7)的信号较A的C-8 (δC 37.3)向高场移动了0.6个化学位移值单位, C-9 (δC 77.9)、C-10 (δC 22.2)和Glc-1' (δC 104.4)的信号较A的C-9 (δC 76.0)、C-10 (δC 20.0)和Glc-1' (δC 102.5)分别向低场移动了1.9、2.2和1.9个化学位移值单位。提示1的C-9构型可能与A不一致。将1进行酸水解, 得到1的苷元(B), B的比旋光度[α] +5.6 (c 0. 35, CHCl3), 与文献[12] [α] +8.1 (c 0.4, CHCl3)接近, 证明B为9S-构型。最终确定1的苷元为单环降倍半萜(9S)-9-hydroxymengastigman-5-en-4-one。
1经酸水解、中和后的水液部分, 经薄层色谱分析, 确定含有D-葡萄糖和D-木糖。进一步将获得的中和后的水液部分蒸馏除水, 然后乙酰化。乙酰化产物与乙酰化D-葡萄糖和乙酰化D-木糖标准品进行气相色谱分析比较, 进一步证实1中所含有的单糖为D-葡萄糖和D-木糖。1的1H NMR显示, 两个单糖的端基氢偶合常数分别为7.6 Hz和8.0 Hz, 提示两个单糖的端基碳构型均为β-构型。在1的非去偶HSQC谱中, 观察到D-葡萄糖和D-木糖的端基碳氢偶合常数JC-H均为162 Hz, 进一步证实D-葡萄糖和D-木糖的端基碳构型均为β-构型。通过1的HMBC谱(图 2), 可观察到δH 4.32 (1H, d, J = 7.6 Hz, 1-H of D-Xyl)与δC 69.9 (C-6' of D-Glc)存在远程相关, 证实D-木糖的C-1''应与D-葡萄糖的C-6'相连, 即为β-D-木糖基-(1→6)-β-D-葡萄糖双糖(樱草糖, primeverose)。
1的HMBC谱中, δH 4.34 (1H, d, J = 8.0 Hz, 1-H of D-Glc)与δC 77.9 (C-9)存在远程相关, 表明D-葡萄糖的C-1'应连接在苷元的C-9。
综上分析, 确定1为降倍半萜双糖苷(9S)-9-hydroxymengastigman-5-en-4-one-9-O-primeveroside, 该化合物为一新化合物。
根据1的1H、13C NMR, 1H-1H COSY, HSQC以及HMBC谱, 对1的1H和13C信号全部进行了归属(表 1)。
实验部分
收起
Bruker AV-400和AV-600核磁共振仪(美国Varian, 以CD3OD、CDCl3、DMSO-d6为溶剂, TMS为内标); Nicolet 6700红外分光光度计(Thermo Electron Corporation, Waltham, USA); AmaZon SL质谱仪(Bruker Corporation, USA); GL-3000半制备高效液相色谱仪(Gelai Precision Instruments Co., Ltd., Chengdu China); 薄层色谱硅胶GF254和柱色谱用硅胶G (青岛海洋化工有限公司, 100~200目、200~300目); MCI CHP-20P (75~150 μm, 日本Mitsubishi公司); GC-2010 (HP-1:17 m×0.2 mm×0.11 μm, Agilent, Santa Clara, CA); 丹桂干花, 2017年10月采自四川成都都江堰市, 经四川大学华西药学院天然药物化学黄静教授鉴定为丹桂Osmanthus fragrans var. aurantiacus, 凭证标本(GH20171008)保存于四川大学华西药学院天然药物学系(药学科教大楼806室)。
1 提取与分离
取丹桂干花4.7 kg, 用95%乙醇浸润10 min后, 用95%乙醇连续回流提取1.5 h, 过滤, 滤液减压浓缩回收溶剂后, 得到乙醇浸膏410 g; 乙醇浸膏在室温下用甲醇复溶, 过滤、浓缩得到甲醇浸膏360 g。甲醇浸膏经硅胶(200~300目)柱色谱, 用二氯甲烷-甲醇(30:1、20:1、10:1、5:1、1:1、0:1)梯度洗脱, 薄层色谱检查后合并相同部分, 得到Frs.1~8。Fr.3 (15.6 g)经反复硅胶柱色谱得到化合物2 (6 mg)。Fr.4 (121.7 g)经反复硅胶柱色谱得到化合物3 (160 mg)。Fr.5 (60 g)经反复硅胶柱色谱得到化合物4 (10 mg)。Fr.7 (50.8 g)经反复硅胶柱色谱、MCI、半制备反相高效液相色谱分离, 得到化合物1 (40 mg)、5 (30 mg)和6 (40 mg)。
2 化合物的酸水解、衍生化及GC分析
称取20 mg化合物1, 加入10% H2SO4, 95 ℃条件下加热3 h, 用10% NaOH调pH = 7后, 用CHCl3萃取3次, 每次3 mL。水层减压浓缩, 再用MeOH溶解过滤得到单糖。分别取单糖、D-葡萄糖对照品1 mg和D-木糖对照品1 mg, 分别加入1 mL无水吡啶、1 mL乙酸酐和0.5 mg DMAP, 室温下搅拌3 h, 加水终止反应。反应液用CH2Cl2萃取3次, 每次1 mL, 得到单糖样品及对照品的乙酰化衍生物。然后进行气相色谱分析, 色谱条件如下。色谱柱: HP-1色谱柱, 进样器和检测器温度均为250 ℃。程序升温:从150到250 ℃, 升温速率: 3 ℃·min-1。单糖样品中D-木糖的保留时间为14.609 min, 与D-木糖对照品的保留时间(tR 14.603 min)基本一致; D-葡萄糖的保留时间为22.071 min, 与D-葡萄糖对照品的保留时间(tR 22.126 min)基本一致。
3 结构鉴定
化合物1:无固形粉末, Molish反应呈阳性; [α] -27.3 (c 0.116, MeOH); mp 115.5~120.0 ℃; 紫外光谱λmaxMeOH nm (logε): 250 (2.81);红外光谱νmaxnear cm-1: 3 363 (-OH)、2 923 (-CH2-)、1 645 (C=O)、1 421 (C=C); HR-ESI-MS显示1的准分子离子峰m/z 527.246 8 [M+Na]+ (计算值527.246 8)。1H NMR (400 MHz, CD3OD)和13C NMR (100 MHz, CD3OD)数据见表 1。
化合物2 (齐墩果酸):白色粉末, Liebermann-Burchard反应呈阳性, 1H NMR (400 MHz, DMSO-d6) δH 5.16 (1H, brs, 12-H), 1.09, 0.89, 0.87, 0.88, 0.85, 0.71, 0.67 (3H each, s, 23, 27, 29, 30, 25, 24, 26-H)。13C NMR (100 MHz, DMSO-d6) δC 179.0 (C-28), 144.3 (C-13), 122.0 (C-12), 77.3 (C-3), 55.2 (C-5), 44.5 (C-9), 46.1 (C-17), 46.0 (C-19), 41.8 (C-14), 41.2 (C-18), 39.3 (C-8), 38.8 (C-4), 38.5 (C-1), 37.0 (C-10), 33.8 (C-21), 33.3 (C-29), 32.9 (C-7), 32.5 (C-22), 30.8 (C-20), 28.7 (C-23), 27.6 (C-15), 27.4 (C-2), 26.1 (C-27), 23.8 (C-30), 23.4 (C-16), 23.0 (C-11), 18.5 (C-6), 17.3 (C-26), 16.5 (C-24), 15.6 (C-25)。
化合物3 (连翘脂素):白色粉末, FeCl3-K3[Fe(CN)6]反应呈阳性, 提示化合物3中含有酚羟基。1H NMR (400 MHz, CDCl3) δH 6.85~6.95 (1H, m, Ar-H), 4.87 (1H, d, J = 5.6 Hz, 7'-H), 4.43 (1H, d, J = 7.2 Hz, 7-H), 4.12, 3.83 (2H, m, 9-H), 3.86, 3.37 (2H, m, 9'-H), 3.33 (1H, m, 8'-H), 2.90 (1H, m, 8-H), 三个甲氧基信号: 3.89 (3H, s, -OCH3), 3.90 (3H, s, -OCH3), 3.91 (3H, s, -OCH3); 13C NMR (100 MHz, CDCl3) δC 148.8 (C-3'), 148.0 (C-3), 146.7 (C-4'), 145.3 (C-4), 133.0 (C-1), 130.9 (C-1'), 119.1 (C-6), 117.1 (C-6'), 114.2 (C-5), 111.0 (C-5'), 108.9 (C-2), 108.5 (C-2'), 87.7 (C-7), 82.0 (C-7'), 71.0 (C-9'), 69.7 (C-9), 56.0, 55.9, 55.9 (OMe-3, 3', 4'), 54.5 (C-8), 50.1 (C-8')。
化合物4 (红景天苷酯):白色粉末, FeCl3-K3[Fe(CN)6]反应呈阳性, 提示化合物4中含有酚羟基。1H NMR (400 MHz, DMSO-d6) δH 7.03 (2H, d, J = 8.4 Hz, 2, 6-H), 6.66 (2H, d, J = 8.4 Hz, 3, 5-H), 5.15 (1H, d, J = 5.2 Hz, 1'-H), 5.04 (2H, m, 8-H), 4.24 (2H, m, 7-H), 3.61~4.24 (4H, m, 2'~5'-H), 2.97~3.16 (3H, m, 2'~4'-OH), 2.73 (2H, m, 6'-H), 2.01 (3H, s, COCH3); 13C NMR (400 MHz, DMSO-d6)δC 170.8 (CO), 156.1 (C-4), 130.2 (C-2), 130.2 (C-6), 129.0 (C-1), 115.5 (C-3), 115.5 (C-5), 103.1 (C-1'), 76.9 (C-3'), 74.0 (C-2'), 73.8 (C-5'), 70.8 (C-8), 70.4 (C-4'), 64.1 (C-6'), 35.3 (C-7), 21.1 (CH3)。
化合物5 (红景天苷):白色块晶, FeCl3-K3[Fe(CN)6]反应呈阳性, 提示化合物5中含有酚羟基。1H NMR (400 MHz, DMSO-d6) δH 7.04 (2H, d, J = 8.4 Hz, 2, 6-H), 6.67 (2H, d, J = 8.4 Hz, 3, 5-H), 4.88~4.97 (3H, m, 2'~4'-OH), 4.48 (1H, t, J = 5.7 Hz, 6'-OH), 4.18 (1H, d, J = 8.0 Hz, 1'-H), 2.95~3.89 (8H, m, 2'~6'-H), 2.75 (2H, m, 7-H); 13C NMR (100 MHz, DMSO-d6) δC 156.0 (C-4), 130.2 (C-2), 130.2 (C-6), 129.1 (C-1), 115.5 (C-3), 115.5 (C-5), 103.3 (C-1'), 77.3 (C-5'), 77.3 (C-3'), 73.9 (C-2'), 70.6 (C-8), 70.4 (C-4'), 61.6 (C-6'), 36.3 (C-7)。
化合物6 (类叶升麻苷):黄色粉末, FeCl3-K3[Fe(CN)6]反应呈阳性, 提示化合物6中含有酚羟基。1H NMR (400 MHz, MeOH-d4):咖啡酰单元: δH 7.40 (1H, d, J = 16.0 Hz, 7-H), 6.92 (1H, d, J = 2.0 Hz, 2-H), 6.82 (1H, dd, J = 8.4, 2.0 Hz, 6-H), 6.65 (1H, d, J = 8.4 Hz, 5-H), 6.13 (1H, d, J = 16.0 Hz, 8-H); 苯乙醇单元: δH 6.55 (1H, d, J = 2.0 Hz, 2-H), 6.53 (1H, d, J = 8.0 Hz, 5-H), 6.42 (1H, dd, J = 8.0, 2.0 Hz, 6-H), 2.64 (2H, m, 7-H), 3.56 (1H, m, 8a-H), 3.87 (1H, m, 8b-H); 葡萄糖单元: δH 4.23 (1H, d, J = 8.0 Hz, 1-H); 鼠李糖单元: δH 0.93 (3H, d, J = 6.0 Hz, 6-H), 5.03 (1H, br s, 1-H); 13C NMR (100 MHz, MeOH-d4):咖啡酰单元: δC 167.5 (CO), 149.3 (C-4), 147.2 (C-3), 146.4 (C-7), 127.1 (C-1), 122.7 (C-6), 116.2 (C-5), 114.8 (C-2), 114.4 (C-8);苯乙醇单元: δC 145.7 (C-3), 144.7 (C-4), 130.9 (C-1), 120.8 (C-6), 116.8 (C-2), 116.0 (C-5), 71.7 (C-8), 36.1 (C-7);葡萄糖单元: δC 103.7 (C-1), 80.9 (C-3), 75.7 (C-2), 75.6 (C-6), 70.1 (C-4), 61.8 (C-6);鼠李糖单元: δC 102.4 (C-1), 73.2 (C-4), 71.8 (C-2), 71.5 (C-3), 69.9 (C-5), 18.2 (C-6)。
化合物2~6:分别与对照品进行共薄层色谱分析, 或与文献比较, 最终确定为齐墩果酸(2)[13]、连翘脂素(3)[14]、红景天苷酯(4)[15]、红景天苷(5)[16]和类叶升麻苷(6)[17]。

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2019年第54卷第12期
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doi: 10.16438/j.0513-4870.2019-0535
  • 接收时间：2019-07-08
  • 首发时间：2026-01-26
  • 出版时间：2019-12-12
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  • 收稿日期：2019-07-08
  • 修回日期：2019-09-07
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    四川大学华西药学院, 四川 成都 610041

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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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