Article(id=1190335350095577304, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1190335347767743264, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2024-0847, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1725206400000, receivedDateStr=2024-09-02, revisedDate=1736697600000, revisedDateStr=2025-01-13, acceptedDate=null, acceptedDateStr=null, onlineDate=1761727662824, onlineDateStr=2025-10-29, pubDate=1744387200000, pubDateStr=2025-04-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1761727662824, onlineIssueDateStr=2025-10-29, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1761727662824, creator=13701087609, updateTime=1761727662824, updator=13701087609, issue=Issue{id=1190335347767743264, tenantId=1146029695717560320, journalId=1189982191388893191, year='2025', volume='60', issue='4', pageStart='843', pageEnd='1182', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1761727662269, creator=13701087609, updateTime=1761729313427, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1190342273276678997, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1190335347767743264, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1190342273276678998, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1190335347767743264, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=1041, endPage=1045, ext={EN=ArticleExt(id=1190335350313681114, articleId=1190335350095577304, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new sesquiterpene from the leaves of Cornus officinalis and their potential neuroprotective activities, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Five sesquiterpenoids were isolated from a 50% acetone extract of Cornus officinalis leaves, a traditional non-medicinal part of Cornus officinalis, using modern column chromatographic techniques such as macroporous adsorbent resins colum, silica gel colum, chromatography gel colum and semi-preparative liquid chromatography techniques. Their structures were identified by modern wave spectroscopy techniques and electronic circular dichroism (ECD) and assigned as cornurtone A (1), cornucadinoside B (2), lacinilene C (3), 3, 12-dihydroxycadalene (4), cornucadinoside C (5). Compound 1 was new compound and compounds 2-5 were first isolated from leaves of Cornus officinalis. Compounds 2 and 3 had potential neuroprotective activities.

, correspAuthors=Xiao-ke ZHENG, Wei-sheng FENG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2025 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=Jing-ke ZHANG, Deng-hui ZHU, Meng LI, Shuang-shuang XIE, Meng-nan ZENG, Xiao-ke ZHENG, Wei-sheng FENG), CN=ArticleExt(id=1190335643336147916, articleId=1190335350095577304, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=山茱萸叶中1个新的倍半萜及其潜在神经保护活性, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用现代柱色谱技术, 如大孔吸附树脂、硅胶、凝胶及半制备液相等, 从山茱萸传统非药用部位山茱萸叶50%丙酮提取物中分离得到5个倍半萜类成分。通过现代波谱学技术以及电子圆二色谱(ECD) 技术鉴定了化合物的结构, 分别为山茱萸新萜苷A (1)、cornucadinoside B (2)、lacinilene C (3)、3, 12-dihydroxycadalene (4)、cornucadinoside C (5)。其中, 化合物1为新化合物, 化合物2~5为首次从山茱萸叶中分离得到, 并且化合物23具有潜在神经保护活性。

, correspAuthors=郑晓珂, 冯卫生, authorNote=null, correspAuthorsNote=
郑晓珂, E-mail:
冯卫生, E-mail:
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Research progress on chemical constituents, bioactivities, formula applications and quality control of Cornus officinalis [J]. Nat Prod Res Dev (天然产物研究与开发), 2020, 32: 1244-1258., articleTitle=null, refAbstract=null), Reference(id=1190349651699139300, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190335350095577304, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=2, rfOrder=1, authorNames=null, journalName=null, refType=null, unstructuredReference=Zhao M, Li L, Cao W, et al. Effects of different drying methods on the properties, stability, and controlled release of Cornus officinalis flavonoids microparticles [J]. 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Chemical structures of compounds 1-5

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The structure and the key HMBC (H→C) correlations of compound 1

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Experimental and calculated electronic circular dichroism (ECD) spectra of compound 1

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No. δH δC No. δH δC
1 - 128.0 12 1.26 (3H, d, J = 6.7 Hz) 22.3
2 7.48 (1H, s) 113.0 13 1.29 (3H, d, J = 6.7 Hz) 22.6
3 - 158.6 14 1.47 (3H, s) 32.8
4 - 147.6 15 2.32 (3H, s) 16.3
5 7.50 (1H, s) 129.0 1′ 5.05 (1H, d, J = 7.3 Hz) 101.9
6 - 124.1 2′ 74.9
7 - 164.9 3′ 78.1
8 5.97 (1H, s) 117.3 4′ 3.27-3.75 (4H, m) 71.1
9 - 206.9 5′ 78.2
10 - 77.5 6′ 3.88 (1H, dd, J = 12.1, 2.0 Hz) 62.4
3.73 (1H, dd, J = 12.1, 4.6 Hz)
11 3.28 (1H, s) 30.1
), ArticleFig(id=1190349651325846240, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1190335350095577304, language=CN, label=Table 1, caption=

1H NMR and 13C NMR spectral data of compound 1 (500 MHz/125 MHz, CD3OD)

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No. δH δC No. δH δC
1 - 128.0 12 1.26 (3H, d, J = 6.7 Hz) 22.3
2 7.48 (1H, s) 113.0 13 1.29 (3H, d, J = 6.7 Hz) 22.6
3 - 158.6 14 1.47 (3H, s) 32.8
4 - 147.6 15 2.32 (3H, s) 16.3
5 7.50 (1H, s) 129.0 1′ 5.05 (1H, d, J = 7.3 Hz) 101.9
6 - 124.1 2′ 74.9
7 - 164.9 3′ 78.1
8 5.97 (1H, s) 117.3 4′ 3.27-3.75 (4H, m) 71.1
9 - 206.9 5′ 78.2
10 - 77.5 6′ 3.88 (1H, dd, J = 12.1, 2.0 Hz) 62.4
3.73 (1H, dd, J = 12.1, 4.6 Hz)
11 3.28 (1H, s) 30.1
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山茱萸叶中1个新的倍半萜及其潜在神经保护活性
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张靖柯 1, 2 , 朱登辉 1, 2 , 李孟 1, 2 , 解双双 1, 2 , 曾梦楠 1, 2 , 郑晓珂 1, 2, * , 冯卫生 1, 2, *
药学学报 | 研究论文 2025,60(4): 1041-1045
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药学学报 | 研究论文 2025, 60(4): 1041-1045
山茱萸叶中1个新的倍半萜及其潜在神经保护活性
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张靖柯1, 2, 朱登辉1, 2, 李孟1, 2, 解双双1, 2, 曾梦楠1, 2, 郑晓珂1, 2, * , 冯卫生1, 2, *
作者信息
  • 1 河南中医药大学, 河南 郑州 450046
  • 2 河南省中药开发工程技术研究中心, 河南 郑州 450046

通讯作者:

郑晓珂, E-mail:
冯卫生, E-mail:
A new sesquiterpene from the leaves of Cornus officinalis and their potential neuroprotective activities
Jing-ke ZHANG1, 2, Deng-hui ZHU1, 2, Meng LI1, 2, Shuang-shuang XIE1, 2, Meng-nan ZENG1, 2, Xiao-ke ZHENG1, 2, * , Wei-sheng FENG1, 2, *
Affiliations
  • 1Henan University of Chinese Medicine, Zhengzhou 450046, China
  • 2The Engineering and Technology Center for Chinese Medicine Development of Henan Province, Zhengzhou 450046, China
出版时间: 2025-04-12 doi: 10.16438/j.0513-4870.2024-0847
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利用现代柱色谱技术, 如大孔吸附树脂、硅胶、凝胶及半制备液相等, 从山茱萸传统非药用部位山茱萸叶50%丙酮提取物中分离得到5个倍半萜类成分。通过现代波谱学技术以及电子圆二色谱(ECD) 技术鉴定了化合物的结构, 分别为山茱萸新萜苷A (1)、cornucadinoside B (2)、lacinilene C (3)、3, 12-dihydroxycadalene (4)、cornucadinoside C (5)。其中, 化合物1为新化合物, 化合物2~5为首次从山茱萸叶中分离得到, 并且化合物23具有潜在神经保护活性。

山茱萸叶  /  倍半萜  /  结构鉴定  /  神经保护

Five sesquiterpenoids were isolated from a 50% acetone extract of Cornus officinalis leaves, a traditional non-medicinal part of Cornus officinalis, using modern column chromatographic techniques such as macroporous adsorbent resins colum, silica gel colum, chromatography gel colum and semi-preparative liquid chromatography techniques. Their structures were identified by modern wave spectroscopy techniques and electronic circular dichroism (ECD) and assigned as cornurtone A (1), cornucadinoside B (2), lacinilene C (3), 3, 12-dihydroxycadalene (4), cornucadinoside C (5). Compound 1 was new compound and compounds 2-5 were first isolated from leaves of Cornus officinalis. Compounds 2 and 3 had potential neuroprotective activities.

Cornus officinalis leaf  /  sesquiterpene  /  structure identification  /  neuroprotective activity
张靖柯, 朱登辉, 李孟, 解双双, 曾梦楠, 郑晓珂, 冯卫生. 山茱萸叶中1个新的倍半萜及其潜在神经保护活性. 药学学报, 2025 , 60 (4) : 1041 -1045 . DOI: 10.16438/j.0513-4870.2024-0847
Jing-ke ZHANG, Deng-hui ZHU, Meng LI, Shuang-shuang XIE, Meng-nan ZENG, Xiao-ke ZHENG, Wei-sheng FENG. A new sesquiterpene from the leaves of Cornus officinalis and their potential neuroprotective activities[J]. Acta Pharmaceutica Sinica, 2025 , 60 (4) : 1041 -1045 . DOI: 10.16438/j.0513-4870.2024-0847
山茱萸为山茱萸科(Cornaceae) 山茱萸属(Cornus) 植物山茱萸(Cornus officinalis Sieb. et Zucc.) 的干燥成熟果实, 我国传统名贵中药材之一, 始载于《神农本草经》, 列为中品, 具有补益肝肾、涩精固脱的作用。临床上用于治疗眩晕耳鸣、腰膝酸痛、阳痿遗精、崩漏带下、大汗虚脱、内热消渴等。现代研究表明山茱萸的化学成分主要包括萜类、鞣质类、黄酮类、木脂素类[1-3]等, 药理活性主要有抗骨质疏松、降血糖、抗肿瘤、神经保护、抗氧化、保肝[4-6]等方面的作用。
山茱萸为药食同源中药材, 其使用量和开发力度也在逐日增加, 寻找山茱萸有效资源的开发利用显得尤为重要。而作为传统非药用部位的山茱萸叶在山茱萸资源利用过程中, 多作为废弃物, 造成严重资源浪费现象, 查阅文献发现, 对于山茱萸叶的研究鲜有报道。基于此, 本实验以山茱萸叶为研究对象, 对其倍半萜类化学成分进行研究, 从中共分离得到5个化合物, 分别为山茱萸新萜苷A (1)、cornucadinoside B (2)、lacinilene C (3)、3, 12-dihydroxycadalene (4)、cornucadinoside C (5), 结构见图 1。其中, 化合物1为新化合物, 化合物2~5为首次从山茱萸叶中分离得到, 对化合物1~5进行Aβ25-35诱导N9细胞损伤的保护作用筛选, 结果显示: 化合物23对Aβ25-35诱导N9细胞损伤细胞活力显著提高, EC50值分别为: 22.7、40.6 μmol·L-1, 为山茱萸资源的进一步开发和利用奠定了物质基础。
化合物1, 白色无定形粉末, 易溶于甲醇、丙酮等溶剂。$ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ -45.127 (c 0.01, CH3OH); HR-ESI-MS m/z 431.167 9 [M+Na]+ (calcd. for C21H28O8Na), 确定化合物的分子式为C21H28O8。红外光谱中, 存在甲基(2 968 cm-1) 和羰基(1 660 cm-1) 等特征吸收峰。在 1H NMR (500 MHz, CD3OD) 中, 低场芳香区中δH 7.50 (1H, s)、7.48 (1H, s)、5.97 (1H, s) 三组质子信号。δH 5.05 (1H, d, J = 7.3 Hz) 结合δH 3.88 (1H, dd, J = 12.1, 2.0 Hz), 3.73 (1H, dd, J = 12.1, 4.6 Hz) 以及δH 3.27~3.75 (4H, m) 推测结构中存在一个葡萄糖的结构片段, 根据其端基氢的偶合常数J = 7.3 Hz, 确定葡萄糖为β。经酸水解, 确定葡萄糖的绝对构型为D-葡萄糖(tR = 18.3 min)。除此之外, 在高场区δH 2.32 (3H, s), 1.47 (3H, s), 1.29 (3H, d, J = 6.7 Hz), 1.26 (3H, d, J = 6.7 Hz)提示该化合物中存在四个甲基取代基。在13C NMR (125 MHz, CD3OD) 中共显示21个碳信号, 其中δC 206.9为酮羰基碳信号, 8个不饱和碳信号(δC 164.9, 158.6, 147.8, 129.0, 128.0, 124.1, 117.3, 113.0), 一组葡萄糖碳信号(δC 101.9, 78.2, 77.5, 74.9, 71.1, 62.4), 4个甲基碳信号(δC 16.4, 22.3, 22.6, 32.8)。在HMBC谱中, δH 3.28 (1H, s) 与δC 22.3, 22.6, 117.3, 124.1, 164.9具有远程相关关系, 提示δH 3.28/30.1次甲基连接在结构的C-7 (δC 164.9) 位上; δH 5.97与δC 22.3, 30.3, 77.3, 124.5, 147.8, 164.9, 206.9具有远程相关关系; δH 1.47与δC 77.5, 147.8, 207.3具有远程相关关系, 提示存在不饱和六元酮的结构片段。根据δH 5.05与δC 158.8具有远程相关关系, 提示葡萄糖连接苷元的位置在C-3位上。综合以上信息可以推测出化合物1的平面结构, 其主要HMBC相关关系见图 2
为进一步明确化合物1的绝对构型, 测定了其ECD图谱(图 3), 采用[B3LYP/6-31G (d), MeOH] 水平上的TDDFT方法计算。通过模拟计算ECD, 当C-10位为R构型时, 化合物的理论计算ECD谱与实际测试图一致, 进而确定化合物1的立体构型。综合以上NMR数据分析, 确定化合物的结构类型为倍半萜烯苷类化合物。查阅国内外文献[7], 未见相关报道, 确定化合物为新化合物, 命名为山茱萸新萜苷A。其NMR数据归属见表 1
称取化合物1 (2.3 mg), 加入2 mol·L-1 HCl溶液2 mL, 封闭, 80 ℃水浴加热3 h, 静置放冷, 氮吹仪吹干样品。然后加入蒸馏水(2 mL), 加入等体积乙酸乙酯萃取3次, 合并水相层, 采用高效液相色谱分析, 分析条件为: Chiralpak AD-H色谱柱(250 mm × 4.6 mm), 正己烷-乙醇-三氟乙酸(750∶250∶0.25) 为流动相(0.5 mL·min-1), 蒸发光散射检测器(ELSD, 漂移管温度为75 ℃, 气体压力为20.0 psi, 柱温为30 ℃) 对化合物1的水解产物进行分析, 通过比较相同液相条件下D-葡萄糖标准品水溶液的保留时间, 两者保留时间一致(tR = 18.3 min), 确定化合物1中所含葡萄糖为D-葡萄糖。
采用MTT法对化合物神经保护活性进行筛选, 与正常组相比, Aβ25-35模型组细胞活力显著降低(P < 0.01), 在10 μmol·L-1浓度下, 化合物23对Aβ25-35诱导N9细胞损伤细胞活力显著提高, 化合物145没有明显活性。经测定, 化合物23的EC50值分别为: 22.7、40.6 μmol·L-1
核磁共振仪(Bruker AVANCE Ⅲ 500) 和高分辨质谱仪(Bruker maxis HD型飞行时间), 德国布鲁克公司; OSB-2000型旋转蒸发仪、N-1111型冷冻水循环装置和NVP-1000型隔膜真空泵, 上海埃朗科技有限公司; LC-52型半制备高效液相色谱仪和UV-200型紫外检测器, 北京世安有限公司; 高效液相色谱仪和蒸发光检测器(美国安捷伦公司)。
色谱柱填料: Sephadex LH-20 (GE Pharmacia Biotech, 美国); Diaion HP-20和MCI Gel CHP-20 (三菱化学公司, 日本); Toyopearl HW-40 (TOSON, 日本); ODS (40~60 μm) 和YMC-Pack ODS-A色谱柱(250 mm × 20 mm, 5 μm, 日本YMC有限公司)。
甲醇(色谱纯, 天津致远化学试剂有限公司); 乙腈(色谱纯) 和氘代溶剂购买于美国天地有限公司; 其他所用试剂正丁醇、甲醇、二氯甲烷、石油醚、乙酸乙酯、乙醇均为分析纯(天津富宇化学试剂有限公司); N9小鼠小胶质细胞(HTX1877) 购自欧特生物科技(深圳) 有限公司; 胎牛血清(杭州四季青公司); DMEM培养基(Gibco Invitrogen, 2082064); 氨苄青霉素(批号: A6920)、链霉素(批号: S8290) 和MTT (批号: M8180, 纯度≥ 98%) 购自于北京索莱宝科技有限公司; Aβ25-35 (批号: P14872) 购买于上海生工生物工程有限公司; PBS缓冲液(浓度: KH2PO4 2 mmol·L-1、Na2HPO4-12H2O 8 mmol·L-1、NaCl 136.0 mmol·L-1、KCl 2.6 mmol·L-1)、所有实验所用蒸馏水及超纯水,均为实验室自制。
山茱萸叶采自河南省南阳市西峡县太平镇山茱萸种植基地, 晒干, 备用。经河南中医药大学董诚明教授鉴定为山茱萸科(Cornaceae) 山茱萸属(Cornus) 山茱萸(Cornus officinalis Sieb. et Zucc) 植物的干燥叶, 留样样品(NO.20180907) 存放于河南中医药大学药学院河南省工程技术研究中心提取与分离实验室。
取干燥山茱萸叶10 kg, 粉碎后, 采用室温下组织破碎提取, 提取溶剂为50%丙酮, 提取3次, 成分提取充分, 滤液沉降1周过滤, 减压浓缩得到总提取物(2.4 kg)。总浸膏加水溶解后, 按照溶剂极性大小分别进行萃取, 得到石油醚部位(50.2 g) 脂溶性成分、乙酸乙酯部位(255.0 g) 中等极性成分、正丁醇部位(334.0 g) 偏大极性成分及水溶性部位(1.71 kg)。
正丁醇部位(334.0 g) 加水溶解充分搅拌, 尽量溶解充分, 上Diaion HP-20大孔吸附树脂柱色谱, 依次用水、10%、20%、30%、50%、70%、95%的乙醇-水系统进行梯度洗脱, 各部位洗脱液经减压浓缩, 冷冻干燥, 得到水洗脱组分Fr. 1 (20.4 g)、10%乙醇洗脱组分Fr. 2 (26.7 g)、20%乙醇洗脱组分Fr. 3 (63.2 g)、30%乙醇洗脱组分Fr. 4 (52.6 g)、50%乙醇洗脱组分Fr. 5 (72.7 g)、70%乙醇洗脱组分Fr. 6 (79.1 g)、95%乙醇洗脱组分Fr. 7 (19.0 g)。Fr. 3上Toyopear HW-40C凝胶柱, 以甲醇-水(0∶100、10∶90、20∶80、30∶70、100∶0) 梯度洗脱, 得到10个组分Fr.3-1~Fr. 3-10。Fr. 3-3 (10.9 g) 上Sephadex凝胶色谱柱, 以甲醇-水(5∶95~50∶50) 梯度洗脱分别得到6个组分(Fr.3-3-1~Fr. 3-3-6), Fr. 3-3-1 (57.4 mg) 经HPLC制备液相分离得到化合物5 (乙腈-水14∶86, tR = 16.6 min, 11.5 mg)。Fr. 3-3-2 (2.9 g) 上ODS反相硅胶柱, 甲醇-水(5∶95~50∶50) 梯度洗脱得到4个组分(Fr.3-3-2-1~Fr. 3-3-2-4), 其中Fr. 3-3-2-2 (28.3 mg) 经HPLC制备液相分离得到化合物1 (乙腈-水15∶85, tR = 18.6 min, 5.8 mg), 2 (乙腈-水17∶83, tR = 20.9 min, 8.9 mg); Fr. 3-3-2-3经HPLC制备液相分离得到化合物3 (乙腈-水22∶78, tR = 23.6 min, 4.6 mg), 4 (乙腈-水19∶81, tR = 20.5 min, 9.7 mg)。
化合物1, 白色无定形粉末, 易溶于甲醇、丙酮等溶剂。$ {\left[\alpha \right]}_{\mathrm{D}}^{20} $ -45.127 (c 0.01, CH3OH); HR-ESI-MS m/z 431.167 9 [M+Na]+ (calcd. for C21H28O8Na), 化合物的分子式为C21H28O8。ECD光谱显示在212 nm处具有一个正Cotton效应, 在330 nm处具有一个负Cotton效应; UV (CH3OH) λmax (logε): 205 (8.27), 220 (5.44), 247 (5.07), 330 (3.01); IR (iTR) νmax cm-1: 3 391, 2 968, 2 926, 1 660, 1 559, 1 076等吸收。1H NMR (500 MHz, CD3OD) 和13C NMR (125 MHz, CD3OD) 见表 1
化合物2, 白色无定形粉末, 1H NMR (500 MHz, CD3OD) δH: 7.52 (1H, s, H-2), 7.76 (1H, s, H-5), 3.50 (1H, m, H-11), 1.34 (3H, d, J = 6.4 Hz, H-12), 1.32 (3H, d, J = 6.4 Hz, H-13), 2.40 (3H, s, H-14), 2.42 (3H, s, H-15), 5.05 (1H, d, J = 7.6 Hz, H-1′), 3.39~3.70 (4H, m, H-2′~H-5′), 3.95 (1H, dd, J = 12.1, 2.3 Hz, H-6′a), 3.74 (1H, dd, J = 12.1, 6.5 Hz, H-6′b); 13C NMR (125 MHz, CD3OD) δC: 122.3 (C-1), 107.8 (C-2), 156.1 (C-3), 125.5 (C-4), 125.7 (C-5), 136.1 (C-6), 144.0 (C-7), 113.6 (C-8), 152.7 (C-9), 113.2 (C-10), 29.3 (C-11), 24.0 (C-12), 24.0 (C-13), 10.8 (C-14), 17.2 (C-15), 102.8 (C-1′), 75.1 (C-2′), 78.4 (C-3′), 71.6 (C-4′), 78.5 (C-5′), 62.7 (C-6′)。以上NMR数据分析并结合参考文献[8], 确定化合物的结构为cornucadinoside B。
化合物3, 白色粉末, 1H NMR (500 MHz, DMSO-d6) δH: 7.15 (1H, s, H-2), 7.38 (1H, s, H-5), 5.77 (1H, s, H-8), 3.22 (1H, m, H-11), 1.17 (3H, t, J = 7.1 Hz, H-12), 1.32 (3H, t, J = 7.1 Hz, H-13), 2.13 (3H, s, H-14), 1.28 (3H, s, H-15); 13C NMR (125 MHz, DMSO-d6) δC: 119.7 (C-1), 112.4 (C-2), 157.3 (C-3), 122.5 (C-4), 127.6 (C-5), 146.9 (C-6), 162.1 (C-7), 115.0 (C-8), 204.0 (C-9), 75.4 (C-10), 28.1 (C-11), 22.1 (C-12), 21.8 (C-13), 28.1 (C-14), 15.7 (C-15)。综上结合文献[7]数据, 确定该化合物的结构为lacinilene C。
化合物4, 白色粉末, 1H NMR (500 MHz, DMSO-d6) δH: 7.22 (1H, s, H-2), 7.87 (1H, s, H-5), 7.02 (1H, d, J = 7.3 Hz, H-8), 7.11 (1H, d, J = 7.3 Hz, H-9), 3.68 (1H, m, H-11), 3.84 (1H, dd, J = 10.6, 5.0 Hz, H-12a), 3.54 (1H, dd, J = 10.6, 8.4 Hz, H-12b), 1.38 (3H, d, J = 6.8 Hz, H-13), 2.52 (3H, s, H-14), 2.32 (3H, s, H-15); 13C NMR (125 MHz, DMSO-d6) δC: 127.0 (C-1), 105.9 (C-2), 154.1 (C-3), 133.6 (C-4), 125.6 (C-5), 126.6 (C-6), 137.5 (C-7), 119.7 (C-8), 124.8 (C-9), 130.3 (C-10), 36.6 (C-11), 67.9 (C-12), 17.4 (C-13), 18.6 (C-14), 16.2 (C-15)。以上NMR数据分析, 结合参考文献[9], 确定该化合物为3, 12-dihydroxycadalene。
化合物5, 白色粉末, 1H NMR (500 MHz, CD3OD) δH: 7.74 (1H, s, H-5), 7.18 (1H, d, J = 7.2 Hz, H-8), 7.10 (1H, d, J = 7.2 Hz, H-9), 3.62 (1H, m, H-11), 1.34 (3H, d, J = 6.5 Hz, H-12), 1.32 (3H, d, J = 6.5 Hz, H-13), 2.49 (3H, s, H-14), 2.91 (3H, s, H-15), 5.71 (1H, d, J = 7.9 Hz, H-1′), 3.16~3.69 (6H, m, H-2′~H-5′), 5.37 (1H, d, J = 7.7 Hz, H-1′′), 3.16~3.69 (6H, m, H-2′′~H-5′′); 13C NMR (125 MHz, CD3OD) δC: 130.4 (C-1), 145.6 (C-2), 145.6 (C-3), 134.2 (C-4), 122.1 (C-5), 131.7 (C-6), 142.6 (C-7), 121.7 (C-8), 129.5 (C-9), 133.8 (C-10), 29.6 (C-11), 24.0 (C-12), 23.9 (C-13), 25.8 (C-14), 18.6 (C-15), 102.6 (C-1′), 76.1 (C-2′), 78.2 (C-3′), 71.8 (C-4′), 78.4 (C-5′), 62.5 (C-6′), 103.3 (C-1′′), 76.1 (C-2′′), 78.4 (C-3′′), 72.0 (C-4′′), 78.4 (C-5′′), 62.6 (C-6′′)。经过以上数据分析, 结合参考文献[10], 确定化合物为cornucadinoside C。
取液氮冻存的N9细胞于37 ℃水浴锅融化至冰水共存状态, 1 000 r·min-1离心5 min, 弃上清后将细胞转入含有10% FBS的DMEM培养基的培养皿中(青、链霉素均为100 u·mL-1), 于5% CO2的37 ℃恒温培养箱培养, 待细胞长至布皿80%~90%进行传代。
N9细胞于37℃、5% CO2培养箱中培养至对数生长期, 按照细胞密度为每毫升2×104个, 每孔200 μL接种于96孔板中, 24 h后分为正常组(CON)、模型组(Aβ25-35, 5 μmol·L-1) 和给药组(10 μmol·L-1 + Aβ25-35, 5 μmol·L-1), 培养24 h后, 每孔加入MTT溶液(5 mg·mL-1) 20 μL, 继续培养4 h, 小心吸净培养液, 每孔加入DMSO 150 μL, 振荡10 min使其完全溶解。酶标仪490 nm测定各孔吸光度值(OD), 计算细胞活力。
实验数据采用SPSS 26.0进行统计学分析, 以均值±标准差($ \overline{x} $ ± s) 表示。P < 0.05表示具有显著性差异, P < 0.01表示具有极显著性差异。
  • 中央引导地方科技发展专项资助项目(豫财科[2016]149)
  • 河南省高等学校重点科研项目(24A360017)
参考文献 引证文献
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Zhao M, Li L, Cao W, et al. Effects of different drying methods on the properties, stability, and controlled release of Cornus officinalis flavonoids microparticles [J]. J Food Sci, 2023, 88: 2313-2324.
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doi: 10.16438/j.0513-4870.2024-0847
  • 接收时间:2024-09-02
  • 首发时间:2025-10-29
  • 出版时间:2025-04-12
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  • 收稿日期:2024-09-02
  • 修回日期:2025-01-13
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中央引导地方科技发展专项资助项目(豫财科[2016]149)
河南省高等学校重点科研项目(24A360017)
作者信息
    1 河南中医药大学, 河南 郑州 450046
    2 河南省中药开发工程技术研究中心, 河南 郑州 450046

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2种不同金属材料的力学参数

Family
属数
Number of
genus
种数
Number of
species
占总种数比例
Percentage of
total species (%)

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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