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Article(id=1190335352683462890, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1190335347767743264, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2024-1153, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1732118400000, receivedDateStr=2024-11-21, revisedDate=1735920000000, revisedDateStr=2025-01-04, acceptedDate=null, acceptedDateStr=null, onlineDate=1761727663441, onlineDateStr=2025-10-29, pubDate=1744387200000, pubDateStr=2025-04-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1761727663441, onlineIssueDateStr=2025-10-29, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1761727663441, creator=13701087609, updateTime=1761727663441, 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=1064, endPage=1068, ext={EN=ArticleExt(id=1190335352884789483, articleId=1190335352683462890, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Iridoids from the roots and rhizomes of Patrinia scabiosaefolia, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Through several chromatographic methods, such as silica gel, Sephadex LH-20 and high performance liquid chromatography (HPLC), six iridoids were isolated from the roots and rhizomes of Patrinia scabiosaefolia. By means of nuclear magnetic resonance (NMR) spectroscopy, 13C NMR calculation and mass spectrometry (MS), their structures were identified as patrinin A (1), patrinin B (2), loganin aglycone (3), isovillosol (4), 1, 3-dimethoxy-4, 7-dimethyl-octahyhro-cyclopenta[c]pyran-6, 7-diol (5) and viburnshosin A (6). Among them, compounds 1 and 2 were new compounds. Furthermore, the anti-influenza virus and anti-inflammatory activities of the isolates were evaluated.

, correspAuthors=Hong-mei LI, 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=Chun-yan ZHAO, Cong MA, Li PU, Dan LIU, Hong-mei LI), CN=ArticleExt(id=1190335638646915961, articleId=1190335352683462890, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=黄花败酱根和根茎中分离得到的环烯醚萜类化合物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶、Sephadex LH-20和高效液相色谱等色谱分离技术, 从黄花败酱(Patrinia scabiosaefolia) 干燥根和根茎的乙酸乙酯萃取相中分离得到6个环烯醚萜类化合物。通过核磁共振、计算13C NMR和质谱等波谱学方法, 将它们分别鉴定为patrinin A (1)、patrinin B (2)、loganin aglycone (3)、isovillosol (4)、1, 3-dimethoxy-4, 7-dimethyl-octahyhro-cyclopenta[c]pyran-6, 7-diol (5)和viburnshosin A (6)。其中, 化合物1和2为新化合物。此外, 对6个化合物进行了抗流感病毒和抗炎活性评价。

, correspAuthors=李洪梅, authorNote=null, correspAuthorsNote=
李洪梅, Tel: 86-871-65920569, E-mail:
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Chemical structures of compounds 1-6

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1H-1H COSY and key HMBC correlations of compounds 1 and 2

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Key ROESY correlations of compounds 1 and 2

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No. 1 2
δH (J in Hz) δC, mult. δH (J in Hz) δC, mult.
1 4.71 d (2.1) 102.4 d 4.39 dd (11.1, 5.6)
4.09 overlap		 71.0 t
3 4.81 d (8.6) 98.9 d 179.4 s
4 2.22 dd (12.0, 8.6) 52.4 d 2.51 m 39.9 d
5 2.54 m 37.8 d 2.22 overlap 42.6 d
6 1.88 overlap
1.71 ddd (14.3, 8.0, 2.4)		 40.2 t 2.11 dd (13.5, 6.6)
1.57 m		 42.2 t
7 4.12 m 74.8 d 4.10 overlap 77.5 d
8 1.83 overlap 40.7 d 1.75 43.9 d
9 1.83 overlap 47.9 d 2.22 overlap 43.9 d
10 1.01 d (6.3) 12.7 q 1.04 d (6.9) 13.6 q
11 174.9 s 1.12 d (6.4) 14.1 q
1-OCH3 3.46 s 55.8 q
3-OCH3 3.43 s 56.7 q
11-OCH3 3.68 s 52.0 q
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1H (600 MHz) and 13C NMR (150 MHz) data of compounds 1 and 2 (CD3OD)

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No. 1 2
δH (J in Hz) δC, mult. δH (J in Hz) δC, mult.
1 4.71 d (2.1) 102.4 d 4.39 dd (11.1, 5.6)
4.09 overlap		 71.0 t
3 4.81 d (8.6) 98.9 d 179.4 s
4 2.22 dd (12.0, 8.6) 52.4 d 2.51 m 39.9 d
5 2.54 m 37.8 d 2.22 overlap 42.6 d
6 1.88 overlap
1.71 ddd (14.3, 8.0, 2.4)		 40.2 t 2.11 dd (13.5, 6.6)
1.57 m		 42.2 t
7 4.12 m 74.8 d 4.10 overlap 77.5 d
8 1.83 overlap 40.7 d 1.75 43.9 d
9 1.83 overlap 47.9 d 2.22 overlap 43.9 d
10 1.01 d (6.3) 12.7 q 1.04 d (6.9) 13.6 q
11 174.9 s 1.12 d (6.4) 14.1 q
1-OCH3 3.46 s 55.8 q
3-OCH3 3.43 s 56.7 q
11-OCH3 3.68 s 52.0 q
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黄花败酱根和根茎中分离得到的环烯醚萜类化合物
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赵春燕 1 , 马聪 2 , 普丽 1 , 刘丹 1 , 李洪梅 1, *
药学学报 | 研究论文 2025,60(4): 1064-1068
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药学学报 | 研究论文 2025, 60(4): 1064-1068
黄花败酱根和根茎中分离得到的环烯醚萜类化合物
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赵春燕1, 马聪2, 普丽1, 刘丹1, 李洪梅1, *
作者信息
  • 1 昆明理工大学生命科学与技术学院, 云南 昆明 650500
  • 2 中检西南计量有限公司工程测量与力学计量检测所, 云南 昆明 650034

通讯作者:

李洪梅, Tel: 86-871-65920569, E-mail:
Iridoids from the roots and rhizomes of Patrinia scabiosaefolia
Chun-yan ZHAO1, Cong MA2, Li PU1, Dan LIU1, Hong-mei LI1, *
Affiliations
  • 1Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, China
  • 2Testing Institute of Engineering Surveying and Mechanical Metrology, CCIC Southwest Metrology Co. Ltd., Kunming 650034, China
出版时间: 2025-04-12 doi: 10.16438/j.0513-4870.2024-1153
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摘要
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采用硅胶、Sephadex LH-20和高效液相色谱等色谱分离技术, 从黄花败酱(Patrinia scabiosaefolia) 干燥根和根茎的乙酸乙酯萃取相中分离得到6个环烯醚萜类化合物。通过核磁共振、计算13C NMR和质谱等波谱学方法, 将它们分别鉴定为patrinin A (1)、patrinin B (2)、loganin aglycone (3)、isovillosol (4)、1, 3-dimethoxy-4, 7-dimethyl-octahyhro-cyclopenta[c]pyran-6, 7-diol (5)和viburnshosin A (6)。其中, 化合物1和2为新化合物。此外, 对6个化合物进行了抗流感病毒和抗炎活性评价。

黄花败酱  /  忍冬科  /  环烯醚萜  /  抗流感病毒  /  抗炎

Through several chromatographic methods, such as silica gel, Sephadex LH-20 and high performance liquid chromatography (HPLC), six iridoids were isolated from the roots and rhizomes of Patrinia scabiosaefolia. By means of nuclear magnetic resonance (NMR) spectroscopy, 13C NMR calculation and mass spectrometry (MS), their structures were identified as patrinin A (1), patrinin B (2), loganin aglycone (3), isovillosol (4), 1, 3-dimethoxy-4, 7-dimethyl-octahyhro-cyclopenta[c]pyran-6, 7-diol (5) and viburnshosin A (6). Among them, compounds 1 and 2 were new compounds. Furthermore, the anti-influenza virus and anti-inflammatory activities of the isolates were evaluated.

Patrinia scabiosaefolia  /  Caprifoliaceae  /  iridoid  /  anti-influenza virus  /  anti-inflammatory
赵春燕, 马聪, 普丽, 刘丹, 李洪梅. 黄花败酱根和根茎中分离得到的环烯醚萜类化合物. 药学学报, 2025 , 60 (4) : 1064 -1068 . DOI: 10.16438/j.0513-4870.2024-1153
Chun-yan ZHAO, Cong MA, Li PU, Dan LIU, Hong-mei LI. Iridoids from the roots and rhizomes of Patrinia scabiosaefolia[J]. Acta Pharmaceutica Sinica, 2025 , 60 (4) : 1064 -1068 . DOI: 10.16438/j.0513-4870.2024-1153
正文
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忍冬科(Caprifoliaceae) 败酱属(Patrinia) 植物有20余种, 广泛分布于亚洲和北美, 并有十余种生长在中国大陆。其中, 许多在中药或民间草药中都有应用, 可以治疗发热、血瘀和炎症, 以及排毒和活血化瘀。败酱属的化学成分包括三萜、环烯醚萜、黄酮和甾体等。其中, 五环三萜是该属的主要成分[1]。
黄花败酱(Patrinia scabiosaefolia Fisch.) 是我国传统常用中药“败酱”的重要来源之一, 始载于《神农本草经》, 列为中品[2], 主产于黑龙江、河北和湖南等省[3]。黄花败酱性辛、苦, 微寒, 具有清热解毒、消肿排脓、活血化瘀的功效, 为临床常用中药, 它的根或全草已被用于治疗各种炎症相关疾病, 如阑尾炎、结肠炎、子宫内膜炎、胰腺炎和皮肤炎症等[4-10], 还可用于治疗病毒感染引起的传染病[6, 9, 11], 对流感病毒、呼吸道合胞病毒和柯萨奇病毒等均有抑制作用[12]。然而, 黄花败酱在抗炎和抗病毒方面的研究大多基于其醇提取物或水提取物, 单体化合物的研究相对较少, 发挥抗炎和抗病毒作用的药效物质基础尚不明确。
近年来, 环烯醚萜类化合物因其显著的生物活性, 如抗菌、抗炎、抗病毒、抗癌、抗氧化和神经保护等, 受到越来越多的关注[7, 11]。课题组前期从黄花败酱的近缘植物岩败酱(Patrinia rupestris)、蜘蛛香(Valeriana jatamansi)、欧缬草(Valeriana officinalis) 和宽叶缬草(Valeriana officinalis var. latifolia) 中得到了一系列具有抗炎和抗流感病毒活性的环烯醚萜[13-20]。作为课题组研究工作的延续, 进一步寻找具有抗炎和抗流感病毒活性的环烯醚萜类成分, 本文从黄花败酱根和根茎的乙酸乙酯相中分离鉴定了6个环烯醚萜类化合物(图 1), 分别为patrinin A (1)、patrinin B (2)、loganin aglycone (3)、isovillosol (4)、1, 3-dimethoxy-4, 7-dimethyl-octahyhro-cyclopenta[c]pyran-6, 7-diol (5) 和viburnshosin A (6)。其中, 化合物1和2为新化合物。此外, 本文对上述环烯醚萜类化合物进行了抗流感病毒和抗炎活性评价。
结果与讨论
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1 结构鉴定
化合物1为无色油状物, 通过HR-ESI-MS的准分子离子峰m/z 297.130 7 [M+Na]+ (计算值297.130 9, C13H22O6Na) 确定其分子式为C13H22O6, 不饱和度为3。化合物1的1H NMR谱(表 1) 显示了1个甲基二重峰信号[δH 1.01 (3H, d, J = 6.3 Hz, Me-10)], 3个甲氧基信号[δH 3.43 (3H, s)、3.46 (3H, s) 和3.68 (3H, s)], 以及3个含氧次甲基信号[δH 4.71 (d, J = 2.1 Hz, H-1), 4.81 (d, J = 8.6 Hz, H-3), 4.12 (m, H-7)]。除了3个甲氧基的碳信号(δC 55.8, 56.7和52.0) 外, 化合物1的13C NMR谱(表 1) 中可以观察到环烯醚萜骨架上的10个碳信号, 包括1个甲基[δC 12.7 (q, C-10)], 1个亚甲基[δC 40.2 (t, C-6)], 7个次甲基[包括3个含氧次甲基δC 102.4 (d, C-1), 98.9 (d, C-3), 74.8 (d, C-7)] 和1个酯羰基信号[δC 174.9 (s, C-11)]。对比发现, 化合物1的上述数据与文献[21]报道的lonicerin数据非常相似, 区别在于化合物1多了一个甲氧基信号, 这导致化合物1的HR-ESI-MS增加了14个质量单位。H-3和H-4 [δH 2.22 (dd, J = 12.0, 8.6 Hz)] 与酯羰基的HMBC相关(图 2) 说明酯羰基位于C-11位。化学位移为δH 3.46、3.43和3.68的3个甲氧基分别与C-1、C-3和C-11存在HMBC相关, 说明3个甲氧基分别连于C-1、C-3和C-11位。C-3位化学位移的变化(δC 91.0→98.9) 也进一步说明了C-3位甲氧基的存在。1H-1H COSY谱(图 2) 中, H-3/H-4/H-5/H2-6/H-7/H-8/H-9/H-1、H/5/H-9以及H-8/Me-10的质子自旋系统充分证实了化合物1平面结构的正确性。化合物1的相对构型是通过生源和ROESY实验(图 3) 确定的。从生源的角度考虑, 天然存在的环烯醚萜H-5和H-9通常为β构型, H-1为α构型[14]。ROESY谱(图 3) 中, H-3/H-5和H-5/Me-10之间的NOE相关说明H-8和3-OCH3均为α构型。H-4与H-3 (J3, 4 = 8.6 Hz) 和H-5 (J4, 5 = 12.0 Hz) 之间的偶合常数说明H-3, H-4和H-5均为β构型[21, 22]。另外, 根据与lonicerin在相同溶剂(CD3OD) 中进行化学位移比较[lonicerin: δH-7 4.18, δC-7 74.4; 1: δH-7 4.12, δC-7 74.8], 初步推测化合物1的7-OH为β构型。为了进一步验证7-OH的构型, 计算了1a (7-OH为β构型) 和1b (7-OH为α构型) 的13C NMR化学位移, 并做了13C NMR化学位移计算值与实验值之间的线性相关和DP4+概率分析。结果表明, 1a的 13C NMR化学位移计算值与实验值之间表现出良好的线性相关(R2 = 0.992 3), 且DP4+值为99.99%, 充分说明化合物1的7-OH为β构型。所以化合物1的结构得以确定, 并命名为patrinin A。
化合物2为无色油状物, 通过HR-ESI-MS的准分子离子峰m/z 207.099 5 [M+Na]+ (计算值207.099 2, C10H16O3Na) 确定其分子式为C10H16O3, 不饱和度为3。化合物2的1H NMR谱(表 1) 显示了2个甲基信号[δH 1.04 (3H, d, J = 6.9 Hz, Me-10) 和1.12 (3H, d, J = 6.4 Hz, Me-11)]。13C NMR谱(表 1) 显示了10个碳信号, 包括2个甲基[δC 13.6 (q, C-10) 和14.1 (q, C-11)], 2个亚甲基[71.0 (t, C-1) 和δC 42.2 (t, C-6)], 5个次甲基[δC 39.9 (d, C-4), 42.6 (d, C-5), 77.5 (d, C-7), 43.9 (d, C-8) 和43.9 (d, C-9)], 以及1个酯羰基信号[δC 179.4 (s, C-3)]。将化合物2的上述数据与糙叶败酱(Patrinia scabra) 中得到的环烯醚萜patriscabrol的数据[23]进行比较, 发现二者结构非常相似, 区别在于化合物2的C-8位没有羟基取代, 这导致了化合物2的C-8 (δC 82.0→43.9) 和C-10位(δC 22.2→13.6) 的高场位移。Me-10在 1H NMR谱中以二重峰出现(d, J = 6.9 Hz), 同时与C-7, C-8和C-9存在HMBC相关(图 2), 充分证实了以上结论。1H-1H COSY谱(图 2) 中, Me-11/H-4/H-5/H2-6/H-7/H-8/H-9/H2-1、H/5/H-9以及H-8/Me-10的质子自旋系统进一步证实了化合物2平面结构的正确性。ROESY谱中, H-5/Me-11、H-9/Me-10和H-4/H-7的NOE相关充分说明Me-10和Me-11为β构型, H-4和H-7为α构型。所以, 化合物2的结构得以确定, 并命名为patrinin B。
化合物3~6的结构是通过与文献报道的光谱数据进行比较来确定的, 它们的结构分别被确定为loganin aglycone (3)[21], isovillosol (4)[24], 1, 3-dimethoxy-4, 7-dimethyl-octahyhro-cyclopenta[c]pyran-6, 7-diol (5)[24]和viburnshosin A (6)[25]。
2 抗流感病毒和抗炎活性评价
采用流感病毒A/WSN/1933 (H1N1) 感染犬肾(Madin-Darby canine kidney, MDCK) 细胞建立病毒感染模型, 以nucleozin作为阳性对照(EC50 = 0.37 μmol·L-1), 对化合物1~6进行抗流感病毒活性评价。结果, 6个化合物均未表现出抗流感病毒活性。
此外, 采用Griess法检测化合物1~6的抗炎活性, L-NMMA作为阳性对照(IC50 = 15.19 μmol·L-1)。结果表明, 6个化合物对脂多糖诱导的小鼠巨噬细胞RAW 264.7中一氧化氮生成并无明显的抑制作用。
3 讨论
本实验从黄花败酱根和根茎的乙酸乙酯相中分离鉴定了6个环烯醚萜类化合物, 包括2个新化合物(化合物1和2)。其中, 化合物1、3和5或保留1位半缩醛羟基或该羟基进一步甲基化, 化合物2和4具有六元环内酯结构, 化合物6为1, 3-开环的裂环环烯醚萜。活性评价结果表明, 上述化合物均未表现出抗流感病毒和抗炎活性。后续研究中, 除环烯醚萜外, 应更加深入系统地开展黄花败酱中其他类型化学成分的研究, 拓宽目标化合物的类型, 以阐明其发挥抗炎和抗病毒作用的药效物质基础, 为黄花败酱的进一步开发利用提供理论依据。
实验部分
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Autopo VI全自动控温型高精度旋光仪(美国Rudolph Research Analytical公司); Bruker AVANCE-III型核磁共振波谱仪(600 MHz, 德国Bruker公司); Agilent 6200系列TOF和6500系列Q-TOF LC/MS系统、Agilent 1260型高效液相色谱仪、ZORBAX SB-C18反相柱(分析型: 4.6 mm × 250 mm, 1 mL·min-1; 半制备型: 9.4 mm × 250 mm, 3 mL·min-1) 和二极管阵列检测器(美国Agilent公司); Hei-VAP Value G3型旋转蒸发仪(德国Heidolph公司); ODS-C18反相填充材料(75 μm, 日本东京理化器械株式会社); GF254薄层色谱硅胶板, 80~100目和200~300目柱层析硅胶(中国青岛海洋化工有限公司); MTT和DMSO (中国Solarbio公司); nucleozin (美国MedChemExpress公司); 胰蛋白酶(中国Roche公司); DMEM细胞培养基(美国Invitrogen公司); 小鼠单核巨噬细胞RAW 264.7 (中国科学院昆明细胞库, 编号KCB200603YJ); 左旋单甲基精氨酸(L-NMMA, 中国碧云天生物技术有限公司)。
黄花败酱根和根茎于2022年7月采自吉林省磐石市烟筒山镇高丽炕山, 并由吉林省磐石市烟筒山镇海成药材花卉苗木专业合作社安海成老师鉴定, 凭证标本(KUST20220704) 存放于昆明理工大学生命科学与技术学院资源药物化学实验室。
1 提取与分离
黄花败酱干燥的根和根茎(13 kg) 经适当粉碎后, 在室温下用95%乙醇浸渍提取3次(每次24 h), 合并提取液, 减压浓缩回收乙醇得到浸膏。将浸膏与适量水混悬后, 依次用石油醚、乙酸乙酯和正丁醇进行萃取, 分别得到石油醚相(79 g)、乙酸乙酯相(670 g) 和正丁醇相(390 g)。乙酸乙酯相用聚酰胺拌样后利用中压液相色谱(ODS) 进行划段, 之后用10%→100%甲醇水进行梯度洗脱, 经薄层色谱(TLC) 检识合并相同馏分, 得到8个段位, Frs. 1~8。
Fr.2 (4.77 g) 利用硅胶柱色谱, 二氯甲烷-甲醇(100∶1→10∶1) 作为流动相进行梯度洗脱, 得到5个组分, Frs.2-1~2-5。Fr.2-1 (516.1 mg) 依次经过Sephadex-LH 20 (甲醇) 和硅胶柱色谱(二氯甲烷-甲醇80∶1和二氯甲烷-乙酸乙酯20∶1) 洗脱, 得到化合物1 (3.1 mg) 和2 (4.2 mg)。Fr.2-2 (743.7 mg) 经Sephadex-LH 20 (甲醇) 除去色素, 并划分为3个组分, Frs.2-2-1~Frs.2-2-3。Frs.2-2-3 (125.1 mg) 经过硅胶柱色谱(石油醚-乙酸乙酯2∶1和二氯甲烷-甲醇50∶1) 洗脱, 然后再用半制备HPLC (50%甲醇水) 纯化, 得到化合物3 (12.6 mg, tR = 8.6 min)、4 (5.8 mg, tR = 10.3 min) 和5 (2.8 mg, tR = 15.8 min)。
Fr.3 (2.47 g) 先用Sephadex-LH 20 (甲醇) 除去色素, 然后用半制备HPLC (40%甲醇水) 纯化, 得到化合物6 (3.8 mg, tR = 8.9 min)。
2 结构鉴定
化合物1无色油状物, [α]$ {}_{\mathrm{D}}^{20.0} $ -5.56 (c 0.18, MeOH); HR-ESI-MS (pos.): m/z 297.130 7 [M+Na]+ (计算值297.130 9, C13H22O6Na); 1H NMR (CD3OD, 600 MHz) 和13C NMR (CD3OD, 150 MHz) 见表 1。
化合物2无色油状物, [α]$ {}_{\mathrm{D}}^{20.0} $ -19.40 (c 0.10, MeOH); HR-ESI-MS (pos.): m/z 207.099 5 [M+Na]+ (计算值207.099 2, C10H16O3Na); 1H NMR (CD3OD, 600 MHz) 和13C NMR (CD3OD, 150 MHz) 见表 1。
3 NMR计算和DP4+分析
NMR计算参照文献[26]报道的方法进行。在CONFLEX 8中进行优化和构象搜索后, 利用Gaussian 16软件在DET-B3LYP/6-31G(d) 气相水平上对构象进行优化。然后, 使用PCM模型在CHCl3的mPW1PW91/6-311+G(2d, p) 水平上使用GIAO (规范无关原子轨道) 方法计算优化后的构型。采用相同的方法, 计算TMS的化学位移值, 并作为参考标准。根据吉布斯自由能计算每种构象的玻尔兹曼平均值。通常, 实验和计算的 13C NMR化学位移之间的线性相关R2较高, 表明结构正确的可能性较高[27]。同时, 对未标定化学位移进行DP4+概率分析[28]。
4 化合物的活性评价
4.1 抗流感病毒活性评价
抗流感病毒活性实验参照文献[29]中描述的方法。利用流感病毒A/WSN/1933 (H1N1) 感染MDCK细胞, 构建体外抗流感病毒活性评价模型。具体操作为: 将MDCK细胞以每孔1.0×104个的密度接种到96孔板中, 并在培养箱中培养24 h后进行药物处理。含有与药物等体积DMSO的病毒维持液、仅含100TCID50病毒量的维持液及nucleozin给药组分别设置为空白对照组、阴性对照组和阳性对照组。实验组为化合物1~6, 终浓度为50 μmol·L-1。给药后在35 ℃、5% CO2的条件下继续培养48 h后, 采用MTT法检测细胞活度。若化合物的保护率超过50%, 则进一步设置不同的浓度梯度进行重复实验, 并利用IBM SPSS Statistics软件计算出EC50值。
4.2 抗炎活性评价
抗炎实验参照文献[30]中描述的方法进行。采用Griess法测定培养基中NO含量的变化。RAW264.7细胞以每孔8×104个的密度接种于96孔板。设置对照组(DMSO)、LPS刺激组(DMSO+1 μg·mL-1 LPS) 及化合物干预组(DMSO+LPS+不同浓度化合物)。设置化合物浓度梯度为3.125、6.25、12.5、25和50 μmol·L-1, 药物处理24 h, L-NMMA为阳性对照。随后, 使用Griess试剂处理并测量吸光值(OD540)。通过MTT法评估化合物对细胞活力的影响。NO生成抑制率= (ODLPS刺激组-OD干预组) / (ODLPS刺激组-OD空白组) ×100%。
基金
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  • 国家自然科学基金资助项目(32060106)
文献
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doi: 10.16438/j.0513-4870.2024-1153
  • 接收时间：2024-11-21
  • 首发时间：2025-10-29
  • 出版时间：2025-04-12
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  • 收稿日期：2024-11-21
  • 修回日期：2025-01-04
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国家自然科学基金资助项目(32060106)
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    1 昆明理工大学生命科学与技术学院, 云南 昆明 650500
    2 中检西南计量有限公司工程测量与力学计量检测所, 云南 昆明 650034

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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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