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Article(id=1308842657426801621, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308842471539442166, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2026-0467, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1776873600000, receivedDateStr=2026-04-23, revisedDate=1780329600000, revisedDateStr=2026-06-02, acceptedDate=null, acceptedDateStr=null, onlineDate=1789982006650, onlineDateStr=2026-09-21, pubDate=1786464000000, pubDateStr=2026-08-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789982006650, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789982006650, creator=13701087609, updateTime=1789982006650, updator=13701087609, issue=Issue{id=1308842471539442166, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='8', pageStart='2821', pageEnd='3220', issueExtLink='null', onlineDate='null', pubDate='1786464000000', pubDateStr='2026-08-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981962332, creator='13701087609', updateTime=1789984137222, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851593773150481, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308842471539442166, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851593773150482, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308842471539442166, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=3129, endPage=3136, ext={EN=ArticleExt(id=1308842657665876950, articleId=1308842657426801621, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Terpenoids isolated from Pteris multifida Poir., columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

The ethanol extract of Pteris multifida was isolated and purified using various column chromatographic methods, including silica gel, Sephdex LH-20 and semi-preparative HPLC. Based on the physicochemical properties of the isolated compounds, their structures were elucidated by spectroscopic data such as MS, NMR, and CD. From the ethyl acetate fraction of P. multifida,18 terpenoids were isolated, including 14 sesquiterpenoids possessing a 1H-inden-1-one nucleus (1-14) and four nortriterpenoids with a megastigmane skeleton (15-18). They were identified as (2S,3S)-2,5,7-trimethyl-3-hydroxyl-6-carboxyl-indan-1-one (ptemulic A) (1), (2S,3S)-2,7-dimethyl-5,6-dihydroxymethyl-indan-1-one (ptemulinol A) (2), dehydropterosin B (3), 6-(1,2-dihydroxyethyl)-2,5,7-trimethyl-indan-1-one (4), pterosin D (5), (3R)-pterosin (6), pterosin D 3-O-β-D-glucopyranoside (7), (3R)-pteroside W (8), (3R)-pteroside D (9), 14-acetyl-pterosin A (10), pterosin A (11), 11-acetyl-pterosin A (12), pterosin A2 (13), (2S,3S)-pterosin C 3-O-β-D-glucopyranoside (14), dearabinosyl pneumonanthoside (15), grasshopper ketone (16), vomifoliol (17), roseoside Ⅰ (18). Compounds 1 and 2 were new compounds, while compounds 3, 4, 10-13, 16 and 18 were isolated from this plant for the first time. New compounds 1 and 2 showed anti-inflammatory activity by inhibiting the production of nitric oxide (NO), with IC50 values of 36.7 and 61.2 μmol·L-1, respectively.

, authors=Cai-ying PENG, Xiao-jun PAN, Jian-qun LIU, Hui-lian HUANG*, Ji-cheng SHU*, authorsList=Cai-ying PENG, Xiao-jun PAN, Jian-qun LIU, Hui-lian HUANG, Ji-cheng SHU, authorCompany=null, correspAuthors=Hui-lian HUANG, Ji-cheng SHU, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2026 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=1308842660371203039, articleId=1308842657426801621, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=井栏边草中萜类成分, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用硅胶柱色谱、凝胶柱色谱和半制备液相色谱等多种方法, 对井栏边草乙醇提取物进行分离与纯化。结合分离单体化合物的理化性质, 通过MS、NMR和CD等波谱数据鉴定其结构。从井栏边草乙酸乙酯部位中分离得到18个萜类化合物, 包括14个1H-茚-1-酮母核的倍半萜(1~14) 和4个四甲基环已烯骨架的降萜(15~18), 分别鉴定为(2S,3S)-2,5,7-三甲基-3-羟基-6-羧基-1-茚-1-酮(井栏边草酸A, 1)、(2S,3S)-2,7-二甲基-5,6-二羟甲基-茚-1-酮(井栏边草醇A) (2)、脱氢蕨素B (3)、6-(1,2-二羟乙基)-2,5,7-三甲基-茚-1-酮(4)、蕨素D (5)、(3R)-蕨素W (6)、蕨素D 3-O-β-D-葡萄糖苷(7)、(3R)-蕨苷W (8)、(3R)-蕨苷D (9)、14-乙酰基-蕨素A (10)、蕨素A (11)、11-乙酰基-蕨素A (12)、蕨素A2 (13)、(2S,3S)-蕨素C 3-O-β-D-葡萄糖苷(14)、dearabinosyl pneumonanthoside (15)、蚱蜢酮(16)、吐叶醇(17)、长寿花糖甙Ⅰ (18)。化合物1和2为新化合物, 3、4、10~13、16和18均为首次从该植物中分离得到。活性筛选结果表明, 新化合物1和2显示出抗炎活性, 能够抑制一氧化氮(NO) 生成, IC50值为36.7和61.2 μmol·L-1。

, authors=彭财英, 潘小军, 刘建群, 黄慧莲*, 舒积成*, authorsList=彭财英, 潘小军, 刘建群, 黄慧莲, 舒积成, authorCompany=null, correspAuthors=黄慧莲, 舒积成, authorNote=

作者贡献:

彭财英负责提取、分离及初稿撰写; 潘小军负责抗炎生物活性测定相关实验; 刘建群参与样品的提取、负责核磁谱图分析及数据归属; 黄慧莲为本文的共同通讯作者, 负责数据分析、参与实验设计和稿件修改; 舒积成为本文通讯作者, 负责实验设计, 提供本文思路, 结构鉴定, 文章修改与定稿。

, correspAuthorsNote=
黄慧莲, Tel: 86-791-87118658, E-mail:
舒积成, E-mail:
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No.12
δHδCδHδC
1-207.6-207.2
22.43 (m)54.62.48 (dq, J = 3.6, 7.3, Hz)54.6
34.69 (d, J = 3.8, Hz)76.24.74 (d, J = 3.6 Hz)75.7
47.32 (s)124.97.69 (s)122.7
5-142.0-149.0
6-131.6-138.6
7-146.0-138.5
8-133.0-133.1
9-154.8-155.8
101.29 (d, J = 7.7 Hz)13.31.31 (d, J = 7.3 Hz)12.9
11----
122.45 (s)20.74.86 (s)63.0
13-177.64.75 (s)-
14---57.0
152.60 (s)15.52.72 (s)13.3
), ArticleFig(id=1308842664691335182, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308842657426801621, language=CN, label=Tab.1, caption=

1H NMR (600 MHz, MeOH-d4) and 13C NMR (150 MHz, MeOH-d4) spectral data of compounds 1 and 2

, figureFileSmall=null, figureFileBig=null, tableContent=
No.12
δHδCδHδC
1-207.6-207.2
22.43 (m)54.62.48 (dq, J = 3.6, 7.3, Hz)54.6
34.69 (d, J = 3.8, Hz)76.24.74 (d, J = 3.6 Hz)75.7
47.32 (s)124.97.69 (s)122.7
5-142.0-149.0
6-131.6-138.6
7-146.0-138.5
8-133.0-133.1
9-154.8-155.8
101.29 (d, J = 7.7 Hz)13.31.31 (d, J = 7.3 Hz)12.9
11----
122.45 (s)20.74.86 (s)63.0
13-177.64.75 (s)-
14---57.0
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井栏边草中萜类成分
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彭财英 , 潘小军 , 刘建群 , 黄慧莲 * , 舒积成 *
药学学报 | 研究论文 2026,61(8): 3129-3136
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药学学报 |研究论文 2026 , 61 (8) : 3129 -3136
井栏边草中萜类成分
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彭财英, 潘小军, 刘建群, 黄慧莲* , 舒积成*
作者信息
  • 江西中医药大学, 现代中药制剂教育部重点实验, 江西 南昌 330004
通讯作者:
黄慧莲, Tel: 86-791-87118658, E-mail:
舒积成, E-mail:
作者简介:

作者贡献:

彭财英负责提取、分离及初稿撰写; 潘小军负责抗炎生物活性测定相关实验; 刘建群参与样品的提取、负责核磁谱图分析及数据归属; 黄慧莲为本文的共同通讯作者, 负责数据分析、参与实验设计和稿件修改; 舒积成为本文通讯作者, 负责实验设计, 提供本文思路, 结构鉴定, 文章修改与定稿。

Terpenoids isolated from Pteris multifida Poir.
Cai-ying PENG, Xiao-jun PAN, Jian-qun LIU, Hui-lian HUANG* , Ji-cheng SHU*
Affiliations
  • Key Laboratory of Modern Preparation of TCM, Misnistry of Education, Jiangxi University of Chinese Medicine, Nanchang 330004, China
出版时间: 2026-08-12 doi: 10.16438/j.0513-4870.2026-0467
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摘要
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利用硅胶柱色谱、凝胶柱色谱和半制备液相色谱等多种方法, 对井栏边草乙醇提取物进行分离与纯化。结合分离单体化合物的理化性质, 通过MS、NMR和CD等波谱数据鉴定其结构。从井栏边草乙酸乙酯部位中分离得到18个萜类化合物, 包括14个1H-茚-1-酮母核的倍半萜(1~14) 和4个四甲基环已烯骨架的降萜(15~18), 分别鉴定为(2S,3S)-2,5,7-三甲基-3-羟基-6-羧基-1-茚-1-酮(井栏边草酸A, 1)、(2S,3S)-2,7-二甲基-5,6-二羟甲基-茚-1-酮(井栏边草醇A) (2)、脱氢蕨素B (3)、6-(1,2-二羟乙基)-2,5,7-三甲基-茚-1-酮(4)、蕨素D (5)、(3R)-蕨素W (6)、蕨素D 3-O-β-D-葡萄糖苷(7)、(3R)-蕨苷W (8)、(3R)-蕨苷D (9)、14-乙酰基-蕨素A (10)、蕨素A (11)、11-乙酰基-蕨素A (12)、蕨素A2 (13)、(2S,3S)-蕨素C 3-O-β-D-葡萄糖苷(14)、dearabinosyl pneumonanthoside (15)、蚱蜢酮(16)、吐叶醇(17)、长寿花糖甙Ⅰ (18)。化合物1和2为新化合物, 3、4、10~13、16和18均为首次从该植物中分离得到。活性筛选结果表明, 新化合物1和2显示出抗炎活性, 能够抑制一氧化氮(NO) 生成, IC50值为36.7和61.2 μmol·L-1。

井栏边草  /  化学成分  /  井栏边草酸A  /  井栏边草醇A  /  抗炎活性

The ethanol extract of Pteris multifida was isolated and purified using various column chromatographic methods, including silica gel, Sephdex LH-20 and semi-preparative HPLC. Based on the physicochemical properties of the isolated compounds, their structures were elucidated by spectroscopic data such as MS, NMR, and CD. From the ethyl acetate fraction of P. multifida,18 terpenoids were isolated, including 14 sesquiterpenoids possessing a 1H-inden-1-one nucleus (1-14) and four nortriterpenoids with a megastigmane skeleton (15-18). They were identified as (2S,3S)-2,5,7-trimethyl-3-hydroxyl-6-carboxyl-indan-1-one (ptemulic A) (1), (2S,3S)-2,7-dimethyl-5,6-dihydroxymethyl-indan-1-one (ptemulinol A) (2), dehydropterosin B (3), 6-(1,2-dihydroxyethyl)-2,5,7-trimethyl-indan-1-one (4), pterosin D (5), (3R)-pterosin (6), pterosin D 3-O-β-D-glucopyranoside (7), (3R)-pteroside W (8), (3R)-pteroside D (9), 14-acetyl-pterosin A (10), pterosin A (11), 11-acetyl-pterosin A (12), pterosin A2 (13), (2S,3S)-pterosin C 3-O-β-D-glucopyranoside (14), dearabinosyl pneumonanthoside (15), grasshopper ketone (16), vomifoliol (17), roseoside Ⅰ (18). Compounds 1 and 2 were new compounds, while compounds 3, 4, 10-13, 16 and 18 were isolated from this plant for the first time. New compounds 1 and 2 showed anti-inflammatory activity by inhibiting the production of nitric oxide (NO), with IC50 values of 36.7 and 61.2 μmol·L-1, respectively.

Pteris multifida  /  chemical constituent  /  ptemulic A  /  ptemulinol A  /  anti-inflammatory activity
彭财英, 潘小军, 刘建群, 黄慧莲, 舒积成. 井栏边草中萜类成分. 药学学报, 2026 , 61 (8) : 3129 -3136 . DOI: 10.16438/j.0513-4870.2026-0467
Cai-ying PENG, Xiao-jun PAN, Jian-qun LIU, Hui-lian HUANG, Ji-cheng SHU. Terpenoids isolated from Pteris multifida Poir.[J]. Acta Pharmaceutica Sinica, 2026 , 61 (8) : 3129 -3136 . DOI: 10.16438/j.0513-4870.2026-0467
正文
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井栏边草(Pteris multifida Poir.) 为凤尾蕨科Pteridaceae凤尾蕨属(Pteris) 植物, 又名凤尾草、凤尾蕨、五叶灵芝等[1], 广泛分布于我国各省区。始载于《本草拾遗》, 药用历史悠久, 具有清热利湿、解毒、凉血、收敛、止血和止痢等功效[2]。现代研究表明, 井栏边草中含有倍半萜(俗称蕨素)、二萜、黄酮、苯丙素等主要类型的次生代谢产物[3], 其提取物及主要成分具有抗肿瘤、抗菌、抗氧化和抗炎等多种药理作用[4-8]。课题组近年来一直致力于蕨类植物的化学物质基础研究[9-14], 本文报道从井栏边草中分离鉴定出18个萜类成分(图1), 包括2个新倍半萜成分—井栏边草酸A (1) 和井栏边草醇A (2), 以及16个已知萜类化合物: 脱氢蕨素B (3)、6-(1,2-二羟乙基)-2,5,7-三甲基-茚-1-酮(4)、蕨素D (5)、(3R)-蕨素W (6)、蕨素D 3-O-β-D-葡萄糖苷(7)、(3R)-蕨苷W (8)、(3R)-蕨苷D (9)、14-乙酰基-蕨素A (10)、蕨素A (11)、11-乙酰基-蕨素A (12)、蕨素A2 (13)、(2S,3S)-蕨素C 3-O-β-D-葡萄糖苷(14)、dearabinosyl pneumonanthoside (15)、蚱蜢酮(16)、吐叶醇(17)、长寿花糖甙Ⅰ (18)。同时, 本研究通过NO生成抑制实验评价了分离新化合物的抗炎活性, 结果显示化合物1和2均具有一定的抗炎活性, IC50值为36.7和61.2 μmol·L-1。
结果与讨论
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1　结构鉴定
化合物1  浅黄色油物(甲醇)。高分辨质谱(HR-ESI-MS) 给出准离子峰[M-H]- m/z 233.082 2 (计算值233.081 9), 由此得出分子式为C13H14O4, 不饱和度为7。UV显示1H-茚-1-酮母核的倍半萜特征吸收(218, 260, 300 nm)[15]。在1H NMR中(表1), 可见一个芳香质子信号[δH 7.32 (1H, s)], 三个甲基信号[δH 2.60 (3H, s), 2.45 (3H, s), 1.29 (3H, d, J = 7.7 Hz)], 以及两个次甲基质子信号[δH 4.69 (1H, d, J = 3.8 Hz), 2.43 (1H, m)]。13C NMR (表1) 结合HSQC谱显示该化合物共有13个碳, 包括8个sp2杂化碳[其中1个酮羰基碳(δC 207.6), 1个羧基碳(δC 177.6), 以及6个芳香碳(δC 124.9、131.6、133.0、142.0、146.0和154.8)], 3个甲基碳(δC 13.3、15.5和20.7), 以及2个sp3杂化次甲基碳(δC 54.6和76.2)。上述波谱特征提示, 化合物1与已知化合物(2S,3S)-pterosin C的NMR数据高度相似[12]。进一步对比两者的NMR数据发现, 主要区别在于: (2S,3S)-pterosin C中连接在C-6位上的羟乙基消失, 而在化合物1中出现了一个羧基(δC 177.6), 表明化合物1为C13骨架的1H-茚-1-酮倍半萜。高分辨质谱结果也支持这一推论。HMBC谱(图2) 进一步确认了化合物1的平面结构: H-10 [δH 1.29 (3H, d, J =1.29 Hz)] 分别与C-1 (δC 207.6)、C-2 (δC 54.6) 和C-3 (δC 76.2) 相关; H-2 [δH 2.43 (1H, m)] 分别与C-1 (δC 207.6)、C-3 (δC 76.2)、C-8 (δC 133.0) 和C-9 (δC 154.8) 相关; H-3 [δH 4.69 (1H, d, J = 3.8 Hz)] 分别与C-1 (δC 207.6)、C-2 (δC 54.6)、C-4 (δC 124.9)、C-8 (δC 133.0)、C-9 (δC 154.8) 和C-10 (δC 13.2) 相关; H-4 [δH 7.32 (1H, s)] 分别与C-3 (δC 76.2)、C-5 (δC 142.0)、C-6 (δC 131.6)、C-8 (δC 133.0)、C-9 (δC 154.8) 和C-12 (δC 20.7) 相关; H-12 [δH 2.45 (3H, s)] 分别与C-4 (δC 124.9)、C-5 (δC 142.0) 和C-6 (δC 131.6) 相关; H-15 [δH 2.60 (3H, s)] 分别与C-6 (δC 131.6)、C-7 (δC 146.0) 和C-8 (δC 133.0) 相关。化合物1的立体构型(2S,3S) 通过NOESY谱(图3)、CD谱(图4)、C-2与C-3的化学位移以及H-3的3J2, 3偶合常数综合确定: 在NOESY谱中, H-10与H-3存在相关信号, 提示C-2位甲基与C-3位氢位于同一侧; CD谱在326 nm处显示正Cotton效应, 表明C-3为S构型[16, 17]; 结合NOESY结果, 可确定C-2也为S构型。此外, C-2和C-3的化学位移分别为54.6和76.2 ppm, H-3的3J2, 3值为3.8 Hz, 这些数据与2S,3S-pterosin C相符, 而与2R,3S-pterosin C有明显差异, 进一步验证C-2为S [17, 18]。综上所述, 化合物1被鉴定为(2S,3S)-2,5,7-trimethyl-3-hydroxy-6-carboxylindan-1-one, 命名为井栏边草酸A。
化合物2  淡黄色油状物(甲醇)。HR-ESI-MS显示准分子离子峰m/z 237.111 9 [M+H]+, 得出分子式为C13H16O4, 不饱和度6。UV显示在215、260、300 nm处具有蕨素类倍半萜成分特征吸收[15]。1H NMR (表1) 显示: 一个芳香质子[δH 7.69 (1H, s)], 两个甲基信号[δH 2.72 (3H, s), 1.31 (3H, d, J = 7.3 Hz)], 两个亚甲基信号[δH 4.86 (2H, s), 4.75 (2H, s)], 以及两个次甲基信号[δH 4.74 (1H, d, J = 3.6 Hz), 2.48 (1H, dq, J = 3.6, 7.3 Hz)]。结合HSQC谱, 13C NMR (表1) 显示13个碳信号, 包括: 1个酮羰基碳信号(δC 207.2), 6个sp2杂化碳(δC 155.8, 149.0, 138.6, 138.5, 133.1, 122.7), 2个亚甲基(δC 63.0, 57.0), 2个甲基(δC 13.3, 12.9), 以及2个次甲基碳(δC 54.6, 75.7)。上述信息与已知化合物(2S,3S)-蕨素T非常相似[12]。主要区别在于, 化合物2缺少一个亚甲基碳(即蕨素T的C-13), 表明该化合物为C13骨架的1H-茚-1-酮倍半萜。HMBC谱(图2) 进一步证实这一推论: H-13 (δH 4.75) 分别与C-5 (δC 149.0)、C-6 (δC 138.6) 和C-7 (δC 138.5) 存在相关信号, 表明该羟甲基连接在C-6位。高分辨质谱结果亦支持上述结论。通过NOESY (图3)、CD谱(图4)、H-3的3J2, 3值及C-2与C-3的化学位移值的综合分析, 确定化合物2的立体构型为2S,3S。在NOESY谱中, H-10与H-3之间存在相关信号, 表明C-2位上的甲基与C-3位上的氢位于同一侧; CD谱在328 nm处显示正Cotton效应, 指示C-3为S构型[16, 17]; 结合NOESY结果, 可推断C-2为S构型。此外, C-2和C-3的化学位移以及H-3的3J2, 3值与(2S,3S) 构型相近, 而与(2R,3S) 构型明显不同, 从而进一步确认了C-2为S构型[17, 18]。基于上述分析, 化合物2的结构被鉴定为(2S,3S)-2,7-dimethyl-5,6-dihydroxymethylindan-1-one, 命名为井栏边草醇A。
2　抗炎活性
新化合物1和2通过体外抑制NO生成实验评估其抗炎活性。为排除细胞毒性对实验结果的干扰, 首先MTT法检测100 μmol·L-1浓度下细胞存活率, 结果显示, 化合物1和2在此浓度下未表现出明显的细胞毒性。活性评价结果表明, 化合物1和2抑制NO生成的半数抑制浓度(IC50) 分别为36.7和61.2 μmol·L-1, 阳性药N-monomethyl-larginine, IC50值为11.7 μmol·L-1, 提示化合物1和2具有一定的抗炎活性。
实验部分
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Agilent1260高效液相色谱仪(美国安捷伦公司); LC-100型制备液相色谱仪(上海伍丰科学仪器有限公司); YMC C18半制备型色谱柱(250 mm× 10 mm, 5 μm, 日本YMC公司); Sephadex LH-20凝胶(美国法玛西亚公司); 国产三菱化学吸附树脂凝胶(75~150 μm; 南京元宝丰制药技术有限公司); 薄层色谱硅胶GF254和柱色谱硅胶(200~300目, 青岛海洋化工有限公司); ZF-20D型暗箱式紫外分析仪(上海宝山顾村电光仪器厂); BS224S型电子天平(北京赛多利斯仪器系统有限公司); AVANCE Ⅲ HD 600 MHz型核磁共振波谱仪(瑞士布鲁克公司); EASY-Nlc1000 LTQ-Orbitrap Elite线性离子阱-串联静电场轨道阱高分辨质谱仪(美国赛默飞世尔公司); 岛津UV-2550紫外可见分光光度计(日本岛津公司); J-1500圆二色光谱仪CD (日本JASCO公司)。试剂均为分析纯或色谱纯(西陇科学股份有限公司); 水为双蒸水。
井栏边草(Pteris multifida Poir.) 全草2021年5月购于中国江西省樟树市, 经江西中医药大学付小梅教授鉴定。凭证标本(编号PM20210501) 已存放在江西中医药大学中药现代制剂重点实验室。
1　提取与分离
将井栏边草自然阴干全草(10 kg) 粗粉后, 采用8倍体积80%乙醇回流提取2次, 每次1 h。合并提取液, 减压浓缩, 得到总浸膏1 520.8 g。将上述浸膏加入适量水捏溶制成悬浮液, 依次用石油醚(PE)、乙酸乙酯(EA) 进行萃取。合并所有EA萃取液, 减压回收溶剂, 得EA萃取部位791.6 g。
取EA部位(约790 g) 经MCI柱层析(5.0 kg, 75~150 μm) 分离, 以乙醇-水(4∶6~1∶0) 梯度洗脱, 得4个组分Fr.E1~E4。取Fr.E2 (153 g) 进一步进行硅胶柱层析, 以二氯甲烷-甲醇(30∶1~3∶1) 梯度洗脱, 薄层色谱(TLC) 检测并合并相似流分, 共获得50个亚组分Fr.E2.1~50。其中, Fr.E2.10 (2.6 g) 经Sephadex LH-20柱色谱(二氯甲烷-甲醇, 1∶1) 分离, TLC检测后合并得到28个流分Fr.E2.10.1~28。Fr.E2.10.7 (218 mg) 经半制备HPLC (甲醇-水, 65∶35) 分离, 得到化合物3 (8.1 mg, tR = 15.4 min)、化合物11 (7.9 mg, tR = 19.7 min) 和化合物13 (11.5 mg, tR = 10.2 min)。Fr.E2.10.15 (176 mg) 经半制备HPLC (甲醇-水, 64∶36) 分离, 得到化合物1 (6.6 mg, tR = 13.9 min) 和化合物2 (12.3 mg, tR = 24.8 min)。Fr.E2.10.21 (204 mg) 经半制备HPLC (甲醇-水, 64∶36) 分离, 得到化合物4 (5.4 mg, tR = 20.3 min)、化合物5 (9.2 mg, tR = 16.4 min) 和6 (7.0 mg, tR = 9.5 min)。
Fr.E2.16 (3.3 g) 经Sephadex LH-20柱色谱(二氯甲烷-甲醇, 1∶1) 分离, TLC检测合并得32个流分Fr.E2.16.1~32。Fr.E2.16.6 (105 mg) 经半制备HPLC (甲醇-水, 60∶40) 分离, 得化合物16 (5.8 mg, tR = 14.3 min) 和化合物17 (7.7 mg, tR = 20.9 min)。Fr.E2.16.11 (217 mg) 经半制备HPLC (甲醇-水, 58∶42) 分离, 得化合物12 (4.3 mg, tR = 25.7 min) 和10 (7.7 mg, tR = 13.4 min)。Fr.E2.16.20 (185 mg) 经半制备HPLC (甲醇-水, 56∶44) 分离, 得化合物7 (6.4 mg, tR = 18.1 min)、8 (13.2 mg, tR = 11.2 min) 和化合物15 (5.2 mg, tR = 26.5 min)。Fr.E2.16.29 (101 mg) 经半制备HPLC (甲醇-水, 55∶45) 分离, 得化合物9 (4.5 mg, tR = 13.5 min)、化合物14 (17.5 mg, tR = 20.4 min) 和化合物18 (3.9 mg, tR = 28.0 min)。
2　结构鉴定
化合物1  浅黄色粉末(甲醇), [α]$ {}_{\mathrm{D}}^{20} $ 19.8 (c 0.11, MeOH); UV (MeOH, HPLC-DAD) λmax: 218, 260, 300 nm; HR-ESI-MS [M-H]- m/z: 233.082 2 (Calcd. 233.081 9), 分子式C13H13O4。1H NMR (600 MHz, MeOH-d4) 和13C NMR (150 MHz, MeOH-d4) 数据见表1。
化合物2  淡黄色油状物(甲醇), [α]$ {}_{\mathrm{D}}^{20} $ 12.6 (c 0.16, MeOH); UV (MeOH, HPLC-DAD) λmax: 215, 260, 300 nm; HR-ESI-MS [M+H]+ m/z: 237.111 9 (Calcd. 237.112 1), 分子式C13H17O4。1H NMR (600 MHz, MeOH-d4) 和13C NMR (150 MHz, MeOH-d4) 数据见表1。
化合物3  淡黄色粉末(甲醇), ESI-MS m/z: 217.1 [M+H]+, 分子式C14H16O2。1H NMR (600 MHz, MeOH-d4) δH: 7.07 (1H, d, J = 1.9 Hz, H-3), 6.66 (1H, s, H-4), 3.57 (1H, t, J = 7.8 Hz, H-14), 2.87 (1H, t, J = 7.8 Hz, H-13), 2.49 (3H, s, H-15), 2.30 (3H, s, H-12), 1.77 (3H, d, J = 1.9 Hz, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 201.5 (C-1), 123.1 (C-2), 143.3 (C-3), 126.7 (C-4), 143.9 (C-5), 137.3 (C-6), 138.2 (C-7), 136.9 (C-8), 144.9 (C-9), 9.9 (C-10), 20.8 (C-12), 32.9 (C-13), 61.7 (C-14), 13.2 (C-15)。对照文献[19], 鉴定化合物3为脱氢蕨素B。
化合物4  淡黄色粉末(甲醇), ESI-MS m/z: 233.1 [M+H]+, 分子式C14H16O3。1H NMR (600 MHz, MeOH-d4) δH: 7.11 (1H, d, J = 1.8 Hz, H-3), 6.69 (1H, s, H-4), 5.20 (1H, dd, J = 5.0, 8.5 Hz, H-13), 3.92 (1H, dd, J = 8.5, 11.5 Hz, H-14a), 3.62 (1H, dd, J = 5.0, 11.5 Hz, H-14b), 2.61 (3H, s, H-15), 2.44 (3H, s, H-12), 1.81 (3H, d, J = 1.8 Hz, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 201.3 (C-1), 124.2 (C-2), 142.9 (C-3), 127.0 (C-4), 144.5 (C-5), 137.6 (C-6), 139.4 (C-7), 137.6 (C-8), 145.8 (C-9), 10.0 (C-10), 21.7 (C-12), 72.6 (C-13), 65.6 (C-14), 14.2 (C-15)。对照文献[20], 鉴定化合物4为6-(1,2-二羟乙基)-2,5,7-三甲基-1-茚-1-酮。
化合物5  淡黄色粉末(甲醇), ESI-MS m/z: 249.1 [M+H]+, 分子式C15H20O3。1H NMR (600 MHz, MeOH-d4) δH: 7.34 (1H, s, H-4), 4.73 (1H, s, H-3), 3.60 (2H, t, J = 7.7 Hz, H-14), 3.00 (2H, t, J = 7.7 Hz, H-13), 2.63 (3H, s, H-15), 2.47 (3H, s, H-12), 1.16 (3H, s, H-11), 1.02 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 211.6 (C-1), 52.4 (C-2), 77.6 (C-3), 126.2 (C-4), 146.3 (C-5), 138.38 (C-6), 138.41 (C-7), 131.2 (C-8), 153.8 (C-9), 23.5 (C-10), 20.7 (C-11), 21.4 (C-12), 33.1 (C-13), 61.6 (C-14), 14.1 (C-15)。对照文献[15], 鉴定化合物5为蕨素D。
化合物6  淡黄色粉末(甲醇), ESI-MS m/z: 265.1 [M+H]+, 分子式C15H20O4。1H NMR (600 MHz, MeOH-d4) δH: 7.41 (1H, s, H-4), 4.97 (1H, d, J = 11.9 Hz, H-15a), 4.92 (1H, d, J = 11.9 Hz, H-15b), 4.69 (1H, s, H-3), 3.60 (2H, t, J = 7.5 Hz, H-14), 3.01 (2H, t, J = 7.5 Hz, H-13), 2.41 (3H, s, H-12), 1.17 (3H, s, H-11), 0.96 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 211.6 (C-1), 52.7 (C-2), 77.6 (C-3), 128.3 (C-4), 147.2 (C-5), 139.1 (C-6), 139.9 (C-7), 131.5 (C-8), 154.2 (C-9), 23.3 (C-10), 20.8 (C-11), 21.4 (C-12), 32.7 (C-13), 62.5 (C-14), 57.1 (C-15)。对照文献[21], 鉴定化合物6为(3R)-蕨素W。
化合物7  淡黄色粉末(甲醇), ESI-MS m/z: 411.19 [M+H]+, 分子式C21H30O8。1H NMR (600 MHz, MeOH-d4) δH: 7.44 (1H, s, H-4), 4.75 (1H, s, H-3), 4.48 (1H, d, J = 7.8 Hz, H-1′), 3.85 (1H, like d, J =11.3 Hz, H-6′a), 3.65 (1H, dd, J = 4.9, 11.3 Hz, H-6′b), 3.53 (2H, t, J = 7.6 Hz, H-14), 3.19~3.34 (4H, m, H-2′, 3′, 4′, 5′), 2.91 (2H, t, J = 7.6 Hz, H-13), 2.54 (3H, s, H-15), 2.39 (3H, s, H-12), 1.19 (3H, s, H-11), 0.99 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 211.4 (C-1), 52.6 (C-2), 86.2 (C-3), 126.8 (C-4), 146.1 (C-5), 138.3 (C-6), 138.6 (C-7), 131.0 (C-8), 151.9 (C-9), 22.9 (C-10), 22.0 (C-11), 21.4 (C-12), 33.1 (C-13), 62.8 (C-14), 14.1 (C-15), 105.6 (C-1′), 75.3 (C-2′), 78.0 (C-3′), 71.7 (C-4′), 78.3 (C-5′), 62.8 (C-6′)。对照文献[15], 鉴定化合物7为蕨素D 3-O-β-D-葡萄糖苷。
化合物8  白色粉末(甲醇), ESI-MS m/z: 427.20 [M+H]+, 分子式C21H30O9。1H NMR (600 MHz, MeOH-d4) δH: 7.52 (1H, s, H-4), 5.09 (1H, d, J = 12.0 Hz, H-15a), 5.03 (1H, d, J = 12.0 Hz, H-15b), 4.81 (1H, s, H-3), 4.28 (1H, d, J = 7.8 Hz, H-1′), 4.05 (1H, m, H-14a), 3.88 (1H, like d, J =12.0 Hz, H-6′a), 3.66 (1H, dd, J = 5.0, 12.0 Hz, H-6′b), 3.70 (1H, m, H-14b), 3.22~3.37 (4H, m, H-2′, 3′, 4′, 5′), 3.20 (2H, m, H-13), 2.54 (3H, s, H-12), 1.24 (3H, s, H-11), 1.08 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 211.9 (C-1), 52.8 (C-2), 77.6 (C-3), 128.2 (C-4), 147.4 (C-5), 138.6 (C-6), 140.1 (C-7), 131.7 (C-8), 154.5 (C-9), 23.2 (C-10), 21.5 (C-11), 20.9 (C-12), 30.0 (C-13), 62.7 (C-14), 57.8 (C-15), 104.5 (C-1′), 71.6 (C-2′), 77.9 (C-3′), 70.2 (C-4′), 78.0 (C-5′), 62.7 (C-6′)。对照文献[22], 鉴定化合物8为(3R)-蕨苷W。
化合物9  白色无定形粉末(甲醇), ESI-MS m/z: 411.19 [M+H]+, 分子式C21H30O8。1H NMR (600 MHz, MeOH-d4) δH: 7.12 (1H, s, H-4), 4.87 (1H, s, H-3), 4.31 (1H, d, J = 7.8 Hz, H-1′), 4.13 (1H, m, H-14a), 3.91 (1H, dd, J = 5.0, 12.1 Hz, H-6′a), 3.84 (1H, dd, J = 1.9, 12.1 Hz, H-6′b), 3.66 (1H, m, H-14b), 3.25~3.34 (4H, m, H-2′, 3′, 4′, 5′), 3.18 (1H, m, H-13a), 3.09 (1H, m, H-13b), 2.65 (3H, s, H-15), 1.15 (6H, s, H-10, 11); 13C NMR (150 MHz, MeOH-d4) δC: 214.5 (C-1), 51.4 (C-2), 75.1 (C-3), 127.0 (C-4), 146.5 (C-5), 136.4 (C-6), 139.3 (C-7), 131.8 (C-8), 153.1 (C-9), 25.8 (C-10), 25.8 (C-11), 21.4 (C-12), 30.1 (C-13), 63.9 (C-14), 13.9 (C-15), 104.4 (C-1′), 71.6 (C-2′), 78.0 (C-3′), 69.2 (C-4′), 79.2 (C-5′), 62.7 (C-6′)。对照文献[23], 鉴定化合物9为(3R)-蕨苷D。
化合物10  淡黄色无定形粉末(甲醇), ESI-MS m/z: 291.16 [M+H]+, 分子式C17H22O4。1H NMR (600 MHz, MeOH-d4) δH: 7.21 (1H, s, H-4), 4.17 (2H, d, J = 7.6 Hz, H-14), 3.72 (1H, d, J = 10.5 Hz, H-11a), 3.47 (1H, d, J = 10.5 Hz, H-11b), 3.26 (1H, d, J = 16.9 Hz, H-3a), 3.10 (2H, t, J = 7.6 Hz, H-13), 2.75 (1H, d, J = 16.9 Hz, H-3b), 2.68 (3H, s, H-15), 2.47 (3H, s, H-12), 2.04 (3H, s, H-2′), 1.10 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 212.8 (C-1), 52.6 (C-2), 37.5 (C-3), 127.1 (C-4), 146.3 (C-5), 135.4 (C-6), 139.0 (C-7), 130.8 (C-8), 154.4 (C-9), 21.3 (C-10), 68.2 (C-11), 21.3 (C-12), 28.7 (C-13), 63.9 (C-14), 13.9 (C-15), 172.8 (C-1′), 20.8 (C-2′)。对照文献[24], 鉴定化合物10为14-乙酰基-蕨素A。
化合物11  白色无定形粉末(甲醇), ESI-MS m/z: 249.15 [M+H]+, 分子式C15H20O3。1H NMR (600 MHz, MeOH-d4) δH: 7.18 (1H, s, H-4), 3.72 (1H, d, J = 10.6 Hz, H-11a), 3.63 (2H, t, J = 7.7 Hz, H-14), 3.47 (1H, d, J = 10.6 Hz, H-11b), 3.25 (1H, d, J = 17.0 Hz, H-3a), 3.01 (2H, t, J = 7.7 Hz, H-13), 2.73 (1H, d, J = 17.0 Hz, H-3b), 2.67 (3H, s, H-15), 2.46 (3H, s, H-12), 1.11 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 212.9 (C-1), 52.6 (C-2), 37.5 (C-3), 126.9 (C-4), 146.2 (C-5), 136.3 (C-6), 138.8 (C-7), 133.1 (C-8), 154.0 (C-9), 21.3 (C-10), 68.3 (C-11), 21.2 (C-12), 32.9 (C-13), 61.7 (C-14), 13.9 (C-15)。对照文献[25], 鉴定化合物11为蕨素A。
化合物12  浅黄色无定形粉末(甲醇), ESI-MS m/z: 291.15 [M+H]+, 分子式C17H22O4。1H NMR (600 MHz, MeOH-d4) δH: 7.20 (1H, s, H-4), 4.18 (1H, d, J = 10.7 Hz, H-11a), 4.13 (1H, d, J = 10.7 Hz, H-11b), 3.64 (2H, t, J = 7.6 Hz, H-14), 3.16 (1H, d, J = 16.8 Hz, H-3a), 3.02 (2H, t, J = 7.6 Hz, H-13), 2.82 (1H, d, J = 16.8 Hz, H-3b), 2.66 (3H, s, H-15), 2.47 (3H, s, H-12), 1.90 (3H, s, H-2′), 1.17 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 210.7 (C-1), 50.2 (C-2), 37.7 (C-3), 127.0 (C-4), 146.6 (C-5), 136.8 (C-6), 139.0 (C-7), 132.4 (C-8), 153.2 (C-9), 21.6 (C-10), 69.6 (C-11), 21.3 (C-12), 32.9 (C-13), 61.7 (C-14), 13.9 (C-15), 172.5 (C-1′), 20.4 (C-2′)。对照文献[26], 鉴定化合物12为11-乙酰基-蕨素A。
化合物13  浅黄色无定形粉末(甲醇), ESI-MS m/z: 411.19 [M+H]+, 分子式C21H30O8。1H NMR (600 MHz, MeOH-d4) δH: 7.07 (1H, s, H-4), 4.11 (1H, d, J = 7.9 Hz, H-1′), 4.03 (1H, d, J = 9.4 Hz, H-11a), 3.68 (1H, dd, J = 1.6, 12.1 Hz, H-glc-6a), 3.51 (3H, m, H-glc-6b, H-14), 3.38 (1H, d, J = 9.4 Hz, H-11b), 3.33 (1H, d, J = 17.0 Hz, H-3a), 2.93~3.22 (4H, m, H-glc-2, 3, 4, 5), 2.89 (2H, t, J = 7.7 Hz, H-13), 2.62 (1H, d, J = 17.0 Hz, H-3b), 2.55 (3H, s, H-15), 2.35 (3H, s, H-12), 1.04 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 212.4 (C-1), 51.4 (C-2), 37.5 (C-3), 127.1 (C-4), 146.4 (C-5), 136.4 (C-6), 138.9 (C-7), 132.6 (C-8), 154.1 (C-9), 22.0 (C-10), 75.0 (C-11), 21.3 (C-12), 32.9 (C-13), 61.7 (C-14), 13.9 (C-15), 104.7 (C-1′), 74.9 (C-2′), 77.8 (C-3′), 71.5 (C-4′), 78.1 (C-5′), 62.7 (C-6′)。对照文献[24], 鉴定化合物13为蕨素A2。
化合物14  白色无定形粉末(甲醇), ESI-MS m/z: 397.18 [M+H]+, 分子式C20H28O8。1H NMR (600 MHz, MeOH-d4) δH: 7.56 (1H, s, H-4), 4.79 (1H, d, J = 4.0 Hz, H-3), 4.63 (1H, d, J = 7.9 Hz, H-1′), 3.93 (1H, d, J = 12.1 Hz, H-6′a), 3.75 (1H, dd, J = 3.8, 12.1 Hz, H-6′b), 3.63 (2H, t, J = 7.9 Hz, H-14), 3.26~3.47 (4H, m, H-2′, 3′, 4′, 5′), 3.02 (2H, t, J = 7.9 Hz, H-13), 2.76 (1H, m, H-2), 2.66 (3H, s, H-15), 2.49 (3H, s, H-12), 1.35 (3H, s, H-10); 13C NMR (150 MHz, MeOH-d4) δC: 208.3 (C-1), 53.0 (C-2), 84.9 (C-3), 126.9 (C-4), 146.2 (C-5), 137.8 (C-6), 138.7 (C-7), 132.5 (C-8), 152.1 (C-9), 14.0 (C-10), 21.3 (C-12), 33.1 (C-13), 61.6 (C-14), 14.0 (C-15), 105.5 (C-1′), 75.3 (C-2′), 78.0 (C-3′), 71.4 (C-4′), 78.1 (C-5′), 62.6 (C-6′)。对照文献[12], 鉴定化合物14为(2S,3S)-蕨素C 3-O-β-D-葡萄糖苷。
化合物15  浅黄色粉末(甲醇), ESI-MS m/z: 371.21 [M+H]+, 分子式C19H30O7。1H NMR (600 MHz, MeOH-d4) δH: 5.90 (1H, s, H-4), 5.78 (1H, dd, J = 6.5, 15.4 Hz, H-8), 5.65 (1H, dd, J = 9.3, 15.4 Hz, H-7), 4.38 (1H, m, H-9), 4.36 (1H, d, J = 7.9 Hz, H-1′), 3.83 (1H, dd, J = 2.4, 12.0 Hz, H-6′a), 3.68 (3H, dd, J = 5.4, 12.0 Hz, H-6′b), 3.17~3.37 (4H, m, H-2′, 3′, 4′, 5′), 2.69 (1H, d, J = 9.3 Hz, H-6), 2.44 (1H, d, J = 16.7 Hz, H-2a), 2.06 (1H, d, J = 16.7 Hz, H-2b), 1.98 (3H, s, H-13), 1.32 (3H, d, J = 6.4 Hz, H-10), 1.05 (3H, s, H-11), 0.99 (3H, s, H-12); 13C NMR (150 MHz, MeOH-d4) δC: 37.2 (C-1), 48.6 (C-2), 202.1 (C-3), 126.1 (C-4), 166.0 (C-5), 56.8 (C-6), 128.9 (C-7), 138.4 (C-8), 76.9 (C-9), 21.1 (C-10), 27.4 (C-11), 28.0 (C-12), 23.9 (C-13), 102.5 (C-1′), 75.3 (C-2′), 78.0 (C-3′), 71.5 (C-4′), 78.1 (C-5′), 62.6 (C-6′)。对照文献[27], 鉴定化合物15为dearabinosyl pneumonanthoside。
化合物16  浅黄色粉末(甲醇), ESI-MS m/z: 225.15 [M+H]+, 分子式C13H20O3。1H NMR (600 MHz, MeOH-d4) δH: 5.85 (1H, s, H-8), 4.23 (1H, m, H-3), 2.22 (1H, m, H-4a), 2.21 (3H, s, H-10), 1.95 (1H, m, H-2a), 1.43 (1H, m, H-2b), 1.39 (6H, s, H-12, 13), 1.36 (1H, m, H-4b), 1.17 (3H, s, H-11); 13C NMR (150 MHz, MeOH-d4) δC: 37.0 (C-1), 50.0 (C-2), 64.4 (C-3), 49.7 (C-4), 72.4 (C-5), 120.0 (C-6), 211.5 (C-7), 101.1 (C-8), 200.8 (C-9), 26.5 (C-10), 29.3 (C-11), 32.3 (C-12), 30.8 (C-13)。对照文献[28], 鉴定化合物16为蚱蜢酮。
化合物17  浅黄色粉末(甲醇), ESI-MS m/z: 225.15 [M+H]+, 分子式C13H20O3。1H NMR (600 MHz, MeOH-d4) δH: 5.88 (m, 1H, H-4), 5.80 (d, J = 4.8 Hz, 1H, H-8), 5.79 (s, 1H, H-7), 4.32 (qd, J = 6.4, 4.8 Hz, 1H, H-9), 2.48 (d, J = 16.9 Hz, 1H, H-2a), 2.16 (d, J = 16.9 Hz, 1H, H-2b), 1.91 (d, J = 1.4 Hz, 3H, H-13), 1.24 (d, J = 6.5 Hz, 3H, H-10), 1.04 (s, 3H, H-11), 1.02 (s, 3H, H-12)。13C NMR (150 MHz, MeOH-d4) δC: 42.4 (C-1), 50.7 (C-2), 201.2 (C-3), 127.1 (C-4), 136.9 (C-7), 130.0 (C-8), 68.6 (C-9), 24.5 (C-10), 23.4 (C-11), 23.8 (C-12), 19.6 (C-13)。对照文献[29], 鉴定化合物17为吐叶醇。
化合物18  白色固体(甲醇), ESI-MS m/z: 387.20 [M+H]+, 分子式为C19H30O8。1H NMR (600 MHz, MeOH-d4) δH: 5.87 (1H, m, H-4), 5.86 (2H, d, J = 4.3 Hz, H-7, 8), 4.46 (1H, m, H-9), 4.34 (1H, d, J = 7.8 Hz, H-1′), 3.85 (1H, dd, J = 11.8, 2.1 Hz, H-6′a), 3.63 (1H, dd, J = 11.7, 5.4 Hz, H-6′b), 3.29~3.22 (3H, m, H-3′, 4′, 5′), 3.17 (1H, dd, J = 9.2, 7.8 Hz, H-2′), 2.52 (1H, d, J = 16.9 Hz, H-2a), 2.15 (1H, d, J = 17.0 Hz, H-2b), 1.92 (3H, d, J = 1.4 Hz, H-13), 1.29 (3H, d, J = 6.4 Hz, H-10), 1.04 (3H, s, H-12), 1.03 (s, 3H, H-11)。13C NMR (150 MHz, MeOH-d4) δC: 42.4 (C-1), 50.7 (C-2), 201.2 (C-3), 127.2 (C-4), 167.2 (C-5), 80.0 (C-6), 131.5 (C-7), 135.3 (C-8), 77.3 (C-9), 21.2 (C-10), 23.4 (C-11), 24.7 (C-12), 19.6 (C-13), 102.7 (C-1′), 75.2 (C-2′), 78.0 (C-3′), 71.6 (C-4′), 78.1 (C-5′), 62.8 (C-6′)。对照文献[30], 确定化合物18为长寿花糖甙Ⅰ。
3　抗炎活性实验
参照文献[31]方法, 以小鼠巨噬细胞RAW264.7为模型, 通过检测NO生成量评价新化合物1和2的抗炎活性。简要实验步骤如下: 用含10%胎牛血清的培养液配制浓度约2×105个/100 μL的单个小鼠巨噬细胞悬液, 取100 μL置于96孔板。预孵育24 h后, 每孔分别加入最高浓度为100 μmol·L-1的受试化合物(梯度稀释为50、25、12.5和6.25 μmol·L-1) 以及1 μg·mL-1的LPS。37 ℃培养18 h后, 取100 μL经LPS或受试化合物处理后的细胞上清液(每组设3个复孔), 加入100 μL Griess试剂A和B, 继续孵育5 min。在570 nm波长处测定吸光度(A) 值, 并以浓度为横坐标(X), NO抑制率为纵坐标(Y) 绘制曲线, 计算化合物的IC50值。

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doi: 10.16438/j.0513-4870.2026-0467
  • 接收时间：2026-04-23
  • 首发时间：2026-09-21
  • 出版时间：2026-08-12
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  • 收稿日期：2026-04-23
  • 修回日期：2026-06-02
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    江西中医药大学, 现代中药制剂教育部重点实验, 江西 南昌 330004

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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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