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Article(id=1308468486129341165, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308468301072458736, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2025-1025, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1756310400000, receivedDateStr=2025-08-28, revisedDate=1761148800000, revisedDateStr=2025-10-23, acceptedDate=null, acceptedDateStr=null, onlineDate=1789892797262, onlineDateStr=2026-09-20, pubDate=1765468800000, pubDateStr=2025-12-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789892797262, onlineIssueDateStr=2026-09-20, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789892797262, creator=13701087609, updateTime=1789892797262, updator=13701087609, issue=Issue{id=1308468301072458736, tenantId=1146029695717560320, journalId=1189982191388893191, year='2025', volume='60', issue='12', pageStart='3545', pageEnd='3798', issueExtLink='null', onlineDate='null', pubDate='1765468800000', pubDateStr='2025-12-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789892753141, creator='13701087609', updateTime=1789893218933, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308470254842175559, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308468301072458736, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308470254842175560, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308468301072458736, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=3758, endPage=3763, ext={EN=ArticleExt(id=1308468486934647535, articleId=1308468486129341165, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Study on the specialized metabolites from the endophytic fungus Cercophora sp. UJN-EF001 in Vaccinium bracteatum, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Thirteen compounds (1-13) were isolated from the ethanol extract of an endophytic fungus Cercophora sp. UJN-EF001 derived from Vaccinium bracteatum, using normal-phase silica gel column chromatography (CC), reversed-phase C18 CC and high-performance liquid chromatography. The structures of these isolates were elucidated through spectroscopic methods including high-resolution mass spectrometry, nuclear magnetic resonance and electronic circular dichroism. Among them, two (1 and 2) were previously unreported molecules, two (3 and 4) were obtained for the first time as natural products, and nine (5-13) were isolated for the first time from the genus Cercophora. All 13 compounds were evaluated for their inhibitory activities against α-glucosidase and nitric oxide (NO) production. As a result, none of them exhibited significant inhibition toward α-glucosidase, while compound 13 displayed moderate inhibition against lipopolysaccharide-induced release of NO in RAW264.7 macrophages with an IC50 value of 34.3 ± 3.8 μmol·L-1.

, authors=Jun-jiang LI1, Yin-bo PAN1, Jiang-ning ZHAO2, Yin-yin WANG1, Jun-sheng ZHANG1, *, Hua ZHANG1, *, authorsList=Jun-jiang LI, Yin-bo PAN, Jiang-ning ZHAO, Yin-yin WANG, Jun-sheng ZHANG, Hua ZHANG, authorCompany=null, correspAuthors=Jun-sheng ZHANG, Hua ZHANG, 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, fund=null), CN=ArticleExt(id=1308468490785018616, articleId=1308468486129341165, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=南烛内生真菌Cercophora sp. UJN-EF001的次级代谢产物研究, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

利用正相硅胶柱色谱、反相C18柱色谱及高效液相色谱等, 对南烛内生真菌Cercophora sp. UJN-EF001的乙醇浸提物中的小分子化学成分进行分离, 共计得到13个化合物(1~13)。进一步通过高分辨质谱、核磁共振波谱、圆二色谱等谱学方法解析鉴定了这些化合物的结构, 其中包含2个未报道的全新分子(1和2)、2个首次发现的新天然产物(3和4)及9个首次从尾孢菌属真菌中分离得到的化合物(5~13)。对这13个化合物进行了α-葡萄糖苷酶抑制活性及一氧化氮(NO)生成抑制活性评价; 结果显示, 这13个化合物对α-葡萄糖苷酶均无明显抑制活性, 而化合物13对脂多糖诱导的RAW264.7巨噬细胞中的NO生成具有较强的抑制活性, IC50值为34.3 ± 3.8 μmol·L-1。

, authors=李俊江1, 潘银波1, 赵江宁2, 王荫荫1, 张君生1, *, 张华1, *, authorsList=李俊江, 潘银波, 赵江宁, 王荫荫, 张君生, 张华, authorCompany=null, correspAuthors=张君生, 张华, authorNote=

作者贡献:

李俊江负责化学成分的提取分离、结构鉴定、相关数据处理及文章初稿撰写; 潘银波和赵江宁负责活性测试及相关数据处理; 王荫荫负责菌种分离与发酵; 张君生负责研究生指导、数据核实及论文修改; 张华负责经费获取、项目管理、研究生指导、数据核实及论文修改。

, correspAuthorsNote=
张君生, E-mail:
张华, E-mail:
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No.1No.2
δCδH (J in Hz)δCδH (J in Hz)
1157.01173.1
2119.5269.35.04, s
3116.51′165.5
4118.26.99, brd (7.6)3′144.67.28, s
5129.07.15, dd (8.1, 7.6)4′116.0
6116.16.79, brd (8.1)5′100.86.61, d (2.4)
768.64.85, s6′167.1
1′128.76.64, d (15.3)7′101.36.55, d (2.4)
2′131.86.59, dd (15.3, 9.7)8′164.5
3′132.06.32, dd (15.1, 9.7)4a′136.3
4′136.15.68, dd (15.1, 7.8)8a′100.6
5′81.83.66, m1-OEt63.24.24, dq (10.8, 7.1)
6′28.71.65, m4.30, dq (10.8, 7.1)
1.54, m14.21.22, t (7.1)
7′10.00.92, t (7.4)2-OH3.39, brs
1-OH8.18, brs6-OMe55.93.86, s
7-OEt66.73.64, m (2H)8′-OH11.27, s
15.21.29, t (7.0)
5′-OEt64.03.57, m
3.37, m
15.51.21, t (7.0)
), ArticleFig(id=1308498530130559066, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308468486129341165, language=CN, label=Tab.1, caption=

1H and 13C NMR data of 1 and 2 in CDCl3

, figureFileSmall=null, figureFileBig=null, tableContent=
No.1No.2
δCδH (J in Hz)δCδH (J in Hz)
1157.01173.1
2119.5269.35.04, s
3116.51′165.5
4118.26.99, brd (7.6)3′144.67.28, s
5129.07.15, dd (8.1, 7.6)4′116.0
6116.16.79, brd (8.1)5′100.86.61, d (2.4)
768.64.85, s6′167.1
1′128.76.64, d (15.3)7′101.36.55, d (2.4)
2′131.86.59, dd (15.3, 9.7)8′164.5
3′132.06.32, dd (15.1, 9.7)4a′136.3
4′136.15.68, dd (15.1, 7.8)8a′100.6
5′81.83.66, m1-OEt63.24.24, dq (10.8, 7.1)
6′28.71.65, m4.30, dq (10.8, 7.1)
1.54, m14.21.22, t (7.1)
7′10.00.92, t (7.4)2-OH3.39, brs
1-OH8.18, brs6-OMe55.93.86, s
7-OEt66.73.64, m (2H)8′-OH11.27, s
15.21.29, t (7.0)
5′-OEt64.03.57, m
3.37, m
15.51.21, t (7.0)
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南烛内生真菌Cercophora sp. UJN-EF001的次级代谢产物研究
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李俊江 1 , 潘银波 1 , 赵江宁 2 , 王荫荫 1 , 张君生 1, * , 张华 1, *
药学学报 | 研究论文 2025,60(12): 3758-3763
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药学学报 |研究论文 2025 , 60 (12) : 3758 -3763
南烛内生真菌Cercophora sp. UJN-EF001的次级代谢产物研究
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李俊江1, 潘银波1, 赵江宁2, 王荫荫1, 张君生1, * , 张华1, *
作者信息
  • 1济南大学生物科学与技术学院, 山东 济南 250022
  • 2青岛市市立医院, 山东 青岛 266011
通讯作者:
张君生, E-mail:
张华, E-mail:
作者简介:

作者贡献:

李俊江负责化学成分的提取分离、结构鉴定、相关数据处理及文章初稿撰写; 潘银波和赵江宁负责活性测试及相关数据处理; 王荫荫负责菌种分离与发酵; 张君生负责研究生指导、数据核实及论文修改; 张华负责经费获取、项目管理、研究生指导、数据核实及论文修改。

Study on the specialized metabolites from the endophytic fungus Cercophora sp. UJN-EF001 in Vaccinium bracteatum
Jun-jiang LI1, Yin-bo PAN1, Jiang-ning ZHAO2, Yin-yin WANG1, Jun-sheng ZHANG1, * , Hua ZHANG1, *
Affiliations
  • 1School of Biological Science and Technology, University of Jinan, Jinan 250022, China
  • 2Qingdao Municipal Hospital, Qingdao 266011, China
出版时间: 2025-12-12 doi: 10.16438/j.0513-4870.2025-1025
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摘要
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利用正相硅胶柱色谱、反相C18柱色谱及高效液相色谱等, 对南烛内生真菌Cercophora sp. UJN-EF001的乙醇浸提物中的小分子化学成分进行分离, 共计得到13个化合物(1~13)。进一步通过高分辨质谱、核磁共振波谱、圆二色谱等谱学方法解析鉴定了这些化合物的结构, 其中包含2个未报道的全新分子(1和2)、2个首次发现的新天然产物(3和4)及9个首次从尾孢菌属真菌中分离得到的化合物(5~13)。对这13个化合物进行了α-葡萄糖苷酶抑制活性及一氧化氮(NO)生成抑制活性评价; 结果显示, 这13个化合物对α-葡萄糖苷酶均无明显抑制活性, 而化合物13对脂多糖诱导的RAW264.7巨噬细胞中的NO生成具有较强的抑制活性, IC50值为34.3 ± 3.8 μmol·L-1。

内生真菌  /  尾孢菌属  /  南烛  /  抗炎活性

Thirteen compounds (1-13) were isolated from the ethanol extract of an endophytic fungus Cercophora sp. UJN-EF001 derived from Vaccinium bracteatum, using normal-phase silica gel column chromatography (CC), reversed-phase C18 CC and high-performance liquid chromatography. The structures of these isolates were elucidated through spectroscopic methods including high-resolution mass spectrometry, nuclear magnetic resonance and electronic circular dichroism. Among them, two (1 and 2) were previously unreported molecules, two (3 and 4) were obtained for the first time as natural products, and nine (5-13) were isolated for the first time from the genus Cercophora. All 13 compounds were evaluated for their inhibitory activities against α-glucosidase and nitric oxide (NO) production. As a result, none of them exhibited significant inhibition toward α-glucosidase, while compound 13 displayed moderate inhibition against lipopolysaccharide-induced release of NO in RAW264.7 macrophages with an IC50 value of 34.3 ± 3.8 μmol·L-1.

endophytic fungi  /  Cercophora  /  Vaccinium bracteatum  /  anti-inflammatory activity
李俊江, 潘银波, 赵江宁, 王荫荫, 张君生, 张华. 南烛内生真菌Cercophora sp. UJN-EF001的次级代谢产物研究. 药学学报, 2025 , 60 (12) : 3758 -3763 . DOI: 10.16438/j.0513-4870.2025-1025
Jun-jiang LI, Yin-bo PAN, Jiang-ning ZHAO, Yin-yin WANG, Jun-sheng ZHANG, Hua ZHANG. Study on the specialized metabolites from the endophytic fungus Cercophora sp. UJN-EF001 in Vaccinium bracteatum[J]. Acta Pharmaceutica Sinica, 2025 , 60 (12) : 3758 -3763 . DOI: 10.16438/j.0513-4870.2025-1025
正文
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南烛(Vaccinium bracteatum Thunb.)最早记载于《开宝本草》, 之后在《图经本草》等本草著作中均有记载[1]。其枝叶在江南一带被用于榨汁浸泡米饭, 煮制成乌饭直接食用[1]; 其果实可入药, 具有强筋益气、固精的功效[2]。本课题组在前期对南烛枝叶活性化学成分进行研究的基础上[3, 4], 又对其内生真菌的代谢成分进行了研究; 从一株毛壳菌属真菌Chaetomium sp. UJN-EF006中分离鉴定了一系列具有抗炎活性的链状聚酮[5]、具有细胞毒活性的新骨架球毛壳菌素[6]及具有优良抗植物灰霉病菌活性的球毛壳菌素[7]类成分。
受上述南烛内生真菌活性成分的研究工作鼓舞, 作者近期对其另一株内生的尾孢菌属真菌Cercophora sp. UJN-EF001进行了放大发酵, 随后对得到的提取物中代谢产物进行了系统研究。本次工作共计分离得到13个化合物, 并利用波谱学方法鉴定了它们的结构(1~13, 图1), 通过圆二色谱(ECD)技术确定了部分化合物的绝对构型; 其中包括2个新化合物1和2、2个首次从天然资源中得到的化合物3和4、9个首次从尾孢菌属真菌得到的已知化合物(5~13)。对这13个化合物进行了α-葡萄糖苷酶抑制活性及一氧化氮(NO)生成抑制活性评价; 结果显示, 这13个化合物对α-葡萄糖苷酶均无明显抑制活性, 而化合物13对脂多糖诱导的RAW264.7巨噬细胞中的NO生成具有较强的抑制活性, IC50值为34.3 ± 3.8 μmol·L-1。
结果与讨论
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1　化合物结构鉴定
化合物1为白色固体。根据其HR-ESI-MS数据(m/z 313.177 8 [M+Na]+, 计算值313.177 4)及核磁共振波谱(NMR)数据(表1), 确定其分子式为C18H26O3, 不饱和度为6。仔细分析其1H和13C NMR数据, 结合HSQC二维核磁谱, 可以推测该分子结构中含有1个1,2,3-三取代苯[δH 6.79 (brd, J = 8.1 Hz), 6.99 (brd, J = 7.6 Hz), 7.15 (dd, J = 8.1, 7.6 Hz); δC 116.1, 116.5, 118.2, 119.5, 129.0, 157.0]、2个共轭反式双键[δH 5.68 (dd, J = 15.1, 7.8 Hz), 6.32 (dd, J = 15.1, 9.7 Hz), 6.59 (dd, J = 15.3, 9.7 Hz), 6.64 (d, J = 15.3 Hz); δC 136.1, 132.0, 131.8, 128.7]、1个连氧次甲基[δH 3.66 (m); δC 81.8]、3个连氧亚甲基[δH 3.37 (m), 3.57 (m), 3.64 (m, 2H), 4.85 (s, 2H); δC 64.0, 66.7, 68.6] 及3个t峰甲基[δH 0.92 (J = 7.4 Hz), 1.21 (J = 7.0 Hz), 1.29 (J = 7.0 Hz); δC 10.0, 15.2, 15.5]; 此外在其氢谱中还观察到1个活泼氢信号(δH 8.18, brs)。上述的共轭双键和苯环占用了全部6个不饱和度, 说明化合物1的结构中没有额外的环系存在。
进一步分析其二维1H-1H COSY数据(图2)可以得到CH3CH2CH(O)CH=CHCH=CH-(C-1′至C-7′)的链状结构片段, 并确定了上述三取代苯(CH-4/CH-5/CH-6)和2个乙氧基基团的存在; 再根据H-6与C-1和C-2, H2-7与C-1、C-2和C-3及H-1′与C-2、C-3和C-4的HMBC相关信号(图2), 确定了苯环上的取代基位置; 最后, 2个乙氧基的位置通过H-5′和H2-7分别与2个连氧亚甲基碳的HMBC相关信号得到确认, 从而完成了化合物1的平面结构的鉴定。该化合物有1个手性中心, 然而其比旋光值却接近0, 圆二色谱(ECD)中也没有明显Cotton效应, 因此推断其为消旋体[8]。由于样品量较少, 为保证后续活性测试的顺利进行, 未对其进行手性拆分。综上, 化合物1被鉴定为rac-3-((1E,3E)-5-ethoxyhepta-1,3-dien-1-yl)-2-(ethoxymethyl)phenol。
化合物2为无色胶状固体。根据其HR-ESI-MS数据(m/z 295.081 6 [M+H]+, 计算值295.081 2)与NMR数据(表1)确定其分子式为C14H14O7, 不饱和度为8。仔细分析其1H和13C NMR数据, 结合HSQC二维核磁谱, 可以得出以下结构片段(或基团)的存在: 2个酯羰基(δC 165.5, 173.1)、1个1,2,3,5-四取代苯[δH 6.55, 6.61, 均为d峰(J = 2.4 Hz); δC 100.6, 100.8, 101.3, 136.3, 164.5, 167.1]、1个双键[δH 7.28 (s); δC 116.0, 144.6]、1个乙氧基[δH 4.24, 4.30, 均为dq峰(J = 10.8, 7.1 Hz); δC 63.2]、1个甲氧基[δH 3.86 (s); δC 55.9] 和2个活泼氢[δH 11.27 (s), 3.39 (brs)]。上述核磁数据解释了8个不饱和度中的7个, 最后1个不饱和度则被归因于化合物2的结构中还有额外1个环。二维1H-1H COSY谱给出的有用信息较少(图2), 只能确认乙氧基基团。进一步分析二维HMBC谱, 根据8′-OH与C-7′、C-8′和C-8a′, H-5′与C-6′、C-7′和C-8a′以及H3-6′-OMe与C-6′的HMBC相关信号(图2), 可以确认1,2,3,5-四取代苯的结构片段; 而8′-OH的化学位移则说明氢键的存在, 进而确定了C-1′在苯环上的取代位置为C-8a′; H′-5与C-4′, H-2与C-3′、C-4′、C-4a′和C-1以及乙氧基中亚甲基氢与C-1的HMBC相关信号则确定了C-4a′位置的取代结构单元; 最后, 根据C-1′和C-3′的化学位移, 结合上述未指认的不饱和度, 可以确定C-1′和C-3′之间的酯键链接; 最后1个活泼氢则基于C-2的化学位移被定为2-OH。化合物2也只有1个手性中心, 通过比较其实验ECD谱与2个可能对映异构体的计算ECD谱(图3), 确定其绝对构型为R。因此化合物2被鉴定为ethyl (R)-2-hydroxy-2-(8-hydroxy-6-methoxy-1-oxo-1H-isochromen-4-yl)acetate。
化合物3为白色固体。根据其HR-ESI-MS数据(m/z 179.070 7 [M+H]+, 计算值179.070 3)及NMR数据推断其分子式为C10H10O3。仔细分析其1H和13C NMR数据, 可以确认以下结构片段(或基团)的存在: 1个酯羰基(δC 170.9)、1个1,2,3-三取代苯[δH 7.09 (d, J = 8.3 Hz), 7.10 (d, J = 7.6 Hz), 7.70 (dd, J = 8.3, 7.6 Hz); δC 112.0, 113.7, 114.7, 138.1, 155.8, 159.9]、1个连氧次甲基[δH 5.55 (q, J = 6.6 Hz); δC 78.6]、1个甲氧基[δH 3.96 (s); δC 56.4] 和1个d峰甲基[δH 1.58 (J = 6.6 Hz); δC 20.6]。根据二维1H-1H COSY数据(图2), 可以得到-CH=CH=CH-与-CH(O)CH3 2个含氢的结构单元; 再通过H-3与C-1、C-3a和C-7a、H-4与C-3和C-3a、H-6与C-7和C-7a以及H3-7-OMe与C-7的HMBC相关信号, 确定了化合物3的平面结构。化合物3只有1个手性中心, 通过比较其实验ECD谱与两个可能对映异构体的计算ECD谱(图3), 确定其绝对构型为S。通过查阅文献, 发现3与2009年Phan等[9]所报道的合成化合物(S)-7-methoxy-3-methylisobenzofuran-1(3H)-one一致, 且只有这1篇文献, 本次工作首次报道其天然存在, 并对其核磁数据进行了详细归属(见实验部分)。
化合物4为无色胶状固体。根据其HR-ESI-MS数据(m/z 237.076 0 [M+H]+, 计算值237.075 7)及NMR数据推断其分子式为C12H12O5。仔细分析其1H和13C NMR数据, 发现其结构与3的结构有很多相似之处, 区别在于4的核磁谱中少了甲氧基和双峰甲基的信号, 但却多了乙酯[δH 1.23 (t, J = 7.1 Hz), 4.16 (q, J = 7.1 Hz); δC 14.4, 62.0, 171.3] 和亚甲基的信号[δH 2.80 (dd, J = 16.5, 7.8 Hz), 3.08 (dd, J = 16.5, 4.6 Hz); δC 40.2]。通过分析其二维1H-1H COSY和HMBC数据(图2), 尤其是H-3、H2-8和乙氧基中亚甲基氢与C-9的关键HMBC相关信号, 确定了化合物4的平面结构。通过比较其实验ECD谱与2个可能对映异构体的计算ECD谱(图3), 确定其绝对构型与3一致, 同为S。通过查阅文献, 发现4与1986年Yeola等[10]所报道的合成化合物ethyl (±)-2-(4-hydroxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate一致, 且只有这1篇文献, 本次工作首次报道其天然光学纯异构体的存在, 并对其核磁数据进行了详细归属(见实验部分)。
除了上述四个化合物, 本次工作中还分离鉴定了9个其他已知化合物, 通过分析其波谱学数据并与文献中数据对比, 分别鉴定为1-acetyl-β-carboline (5)[11]、polygonolide (6)[12]、5-hydroxymethyl-furaldehyde (7)[13]、p-hydroxyphenethyl alcohol (8)[14]、p-hydroxybenzaldehyde (9)[15]、(-)-regiolone (10)[16]、4-ethoxy benzoic acid (11)[17]、8-hydroxy-6-methoxyisochroman-1-one (12)[18]和ethyl ferulate (13)[19]。
2　活性评价
本课题对1~13进行了α-葡萄糖苷酶抑制活性检测, 以阿卡波糖(acarbose)为阳性药(IC50 = 55.0 ± 2.5 μmol·L-1)。在100 μmol·L-1初筛浓度下, 所有化合物对α-葡萄糖苷酶均无显著抑制活性(抑制率 < 50%)。
随后, 通过测试化合物1~13对脂多糖(lipopolysaccharide, LPS)刺激的RAW264.7巨噬细胞中NO生成抑制的活性来评价其抗炎潜力, 以地塞米松(dexamethasone)作为阳性对照(IC50 = 2.2 ± 1.0 μmol·L-1)。在20和40 μmol·L-1 2个初筛浓度下, 化合物13显示了最好的抑制活性, 进一步测试得到13的IC50值为34.3 ± 3.8 μmol·L-1 (图4)。
实验部分
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Bruker Avance DRX600核磁共振波谱仪[瑞士布鲁克公司, 化学位移δ, 耦合常数J, 使用氘代溶剂残留峰定标: CDCl3 (δH 7.26, δC 77.16), CD3OD (δH 3.31, δC 49.00)]; 安捷伦6545四极杆-飞行时间高分辨质谱仪(德国安捷伦科技有限公司); Rudolph Ⅵ高精旋光仪(美国鲁道夫公司); Heidolph Hei-VAPG3旋转蒸发仪(德国海道尔夫公司); Chirascan圆二色谱仪(英国应用光物理公司); DLSK-10/20循环冷凝泵(郑州科泰试验设备有限公司); Agilent 1260高效液相色谱仪(安捷伦科技中国有限公司); LA104/A分析天平(济南东仪实验室设备有限公司); Spark 10M型多功能酶标仪(Tecan公司); Nicolet 380傅立叶变换红外光谱仪(美国Thermo公司)。
正相硅胶(H、200~300目、300~400目, 青岛海洋化工有限公司); 反相C18硅胶和氘代溶剂(德国默克科技有限公司); Agilent SB-C18色谱柱(9.4 mm × 250 mm, 美国安捷伦科技有限公司); 薄层色谱(TLC)硅胶板(青岛海洋化工有限公司); 色谱纯溶剂(瑞典欧普森化工有限公司); 分析纯试剂(天津富宇精细化工有限公司)。如无特殊说明, 化合物分离过程中使用的溶剂体系均为体积比; 高效液相设置流速3.00 mL·min-1。
菌种是从南烛(Vaccinium bracteatum Thunb.)的新鲜叶子[5]中分离得到的优势菌株, 经DNA提取、扩增、测序和序列对比后, 鉴定为尾孢菌属(Cercophora)真菌, 现存于济南大学生物科学与技术学院(保藏号: Cercophora sp. UJN-EF001)。
1　菌种发酵
将Cercophora sp. UJN-EF001接种于马铃薯葡萄糖琼脂(PDA)培养基中, 在180 r·min-1的摇床上于28 ℃培养3天作为后续发酵种子培养液。取20 mL种子培养液接种至装有固体大米培养基的1 L锥形瓶中(每瓶含市售大米80 g、酵母提取物0.4 g、蛋白胨0.5 g、葡萄糖0.4 g及120 mL水)。将锥形瓶在28 ℃静置条件下培养发酵35天。发酵结束后, 用95%乙醇对大米培养基进行3次浸泡提取, 所得提取溶液经减压浓缩后用乙酸乙酯萃取5次, 最终获得147 g粗提物。
2　提取与分离
使用200~300目正相硅胶色谱柱对乙酸乙酯相萃取物进行分离, 以石油醚-乙酸乙酯体系(1∶0~1∶5)进行梯度洗脱, 得到7段样品(A~G)。
取B段样品(6.99 g)进行反相C18色谱柱层析分离, 以甲醇-水作流动相进行梯度洗脱(75%~100%), 得到6段样品(B1~B6)。B1段样品使用高效液相色谱进行纯化(45% MeCN-H2O)得到化合物5 (0.8 mg, tR = 20.0 min)和6 (2.2 mg, tR = 36.0 min); B2段样品同样使用高效液相色谱进行纯化(55% MeCN-H2O)得到化合物1 (0.6 mg, tR = 14.0 min)。
取D段样品(0.8 g)使用300~400目正相硅胶色谱柱进行分离, 以二氯甲烷-甲醇作为流动相进行梯度洗脱(1∶0~50∶1), 得到D1~D4段样品。再用反相C18色谱柱对D3段样品进行分离(60%~100%甲醇-水), 得到19段样品(D3-1~D3-19)。使用高效液相色谱对D3-1进行分离(15% MeCN-H2O), 得到化合物7 (7.5 mg, tR = 7.0 min)、8 (4.2 mg, tR = 13.0 min)、9 (0.9 mg, tR = 23.0 min)和10 (2.6 mg, tR = 45.0 min); 同样用高效液相色谱对D3-4进行分离(15%~35% 乙腈-水), 得到化合物3 (1.3 mg, tR = 33.0 min)、4 (5.5 mg, tR = 38.5 min)、11 (1.5 mg, tR = 51.0 min)、12 (1.1 mg, tR = 57.0 min)、2 (2.0 mg, tR = 61.0 min)和13 (0.5 mg, tR = 72.0 min)。
3　化合物1~4理化数据
化合物1: 白色固体; 无明显旋光值; UV (MeOH) λmax (log ε) 283 (4.74), 224 (4.78) nm; ECD无明显Cotton效应; IR (film) νmax 3 353, 2 920, 2 848, 1 736, 1 660, 1 631, 1 577, 1 465, 1 371, 1 270, 1 219, 1 088, 987 cm-1; 1H和13C NMR (in CD3OD)见表1; HR-ESI-MS m/z 313.177 8 [M + Na]+ (计算值C18H26O3Na+, 313.177 4)。
化合物2: 无色胶状固体; [α]$ {}_{\mathrm{D}}^{28} $ -39 (c 0.20 MeOH); UV (MeOH) λmax (log ε) 244 (5.48) nm; ECD (0.13 mg·mL-1, MeOH) λ (Δε) 238 (-12.62), 218 (8.35), 201 (-0.73), 192 (3.87) nm; IR (film) νmax 3 418, 3 003, 3 916, 1 738, 1 678, 1 642, 1 620, 1 566, 1 510, 1 434, 1 404, 1 313, 1 236, 1 207, 1 165, 1 023, 951, 842, 799, 705 cm-1; 1H和13C NMR (in CD3OD)见表1; HR-ESI-MS m/z 295.081 6 [M+H]+ (计算值C14H15O7+, 295.081 2)。
化合物3: 白色固体; [α]$ {}_{\mathrm{D}}^{28} $ -6.2 (c 0.13 MeOH); ECD (0.13 mg·mL-1, MeOH) λ (Δε) 248 (-0.66), 237 (0.44), 220 (-0.37), 211 (0.23), 195 (3.90) nm; IR (film) νmax 3 427, 3 003, 2 920, 1 743, 1 651, 1 485, 1 436, 1 407, 1 315, 1 281, 1 245, 1 207, 1 019, 951, 709 cm-1; 1H NMR (600 MHz, CD3OD) δH 7.70 (dd, J = 8.3, 7.6 Hz, H-5), 7.10 (d, J = 7.6 Hz, H-4), 7.09 (d, J = 8.3 Hz, H-6), 5.55 (q, J = 6.6 Hz, H-3), 3.96 (s, 3H, OCH3), 1.58 (d, J = 6.6 Hz, H-8); 13C NMR (151 MHz, CD3OD) δC 170.9 (C-1), 159.9 (C-7), 155.8 (C-3a), 138.1 (C-5), 113.7 (C-7a), 114.7 (C-4), 112.0 (C-6), 78.6 (C-3), 56.4 (OCH3), 20.6 (C-8); HR-ESI-MS m/z 179.070 7 [M+H]+ (计算值C10H11O3+, 179.070 3)。
化合物4: 无色胶状固体; [α]$ {}_{\mathrm{D}}^{28} $ -15 (c 0.55 MeOH); ECD (0.14 mg·mL-1, MeOH) λ (Δε) 297 (2.35), 248 (-2.54), 236 (1.85), 220 (-3.10), 200 (5.77) nm; IR (film) νmax 3 424, 2 996, 3 918, 1 752, 1 606, 1 472, 1 436, 1 404, 1 375, 1 313, 1 189, 1 019, 951, 799, 693 cm-1; 1H NMR (600 MHz, CD3OD) δH 7.55 (dd, J = 8.2, 7.5 Hz, H-5), 7.00 (d, J = 7.5 Hz, H-4), 6.89 (d, J = 8.2 Hz, H-6), 5.82 (dd, J = 7.8, 4.6 Hz, H-3), 4.16 (q, J = 7.1 Hz, 2H, OCH2CH3), 3.08 (dd, J = 16.5, 4.6 Hz, Ha-8), 2.80 (dd, J = 16.5, 7.8 Hz, Hb-8), 1.23 (t, J = 7.1 Hz, 3H, OCH2CH3); 13C NMR (151 MHz, CD3OD) δC 171.3 (C-1), 171.0 (C-9), 158.4 (C-7), 152.3 (C-3a), 137.7 (C-5), 117.1 (C-6), 113.8 (C-4), 112.6 (C-7a), 78.4 (C-3), 62.0 (OCH2CH3), 40.2 (C-8), 14.4 (OCH2CH3); HR-ESI-MS m/z 237.076 0 [M+H]+ (计算值C12H13O5+, 237.075 7)。
4　ECD计算
化合物2~4首先用ChemDraw 14.0软件进行MM2力场分析初步确认化合物的初始构象并保存为‘.mol2’格式的文件, 再利用Maestro 10.2软件在3.01 kcal·mol-1的能量窗口中使用MMFFs力场进行构象搜索。化合物2通过Gaussian 16软件在B3LYP/6-311G(d, p)水平上对优化后的构象进行重新优化和含时密度泛函理论(TD-DFT)计算, 3和4同样利用Gaussian 16软件在CAM-B3LYP/6-311G(d, p)水平上对优化后的构象进行重新优化和TD-DFT计算, 以确认重新优化的各构象能量处于最低。最后使用SpecDis 1.71软件获得理论ECD谱图。
5　活性测试
5.1　 α-葡萄糖苷酶抑制活性测试
α-葡萄糖苷酶抑制活性测试实验步骤参考本课题组近期发表论文中的流程[20]。
5.2　NO生成抑制活性测试
对分离化合物NO生成抑制活性的测试采用经典的LPS诱导的RAW264.7巨噬细胞模型, 详细实验流程和步骤见前述报道[21]。简述如下: 取处于对数生长期的细胞进行消化、离心及重悬后, 按每孔细胞数1×105个接种于96孔板中, 培养12 h后加入待测化合物。设置空白对照组、模型对照组(LPS 0.5 μg·mL-1)和给药组(不同浓度的单体化合物+ LPS 0.5 μg·mL-1)。加药24 h后, 通过Griess反应测定化合物对巨噬细胞产生NO的抑制作用, 用酶标仪于540 nm波长处检测各孔吸光度值, 并计算抑制率。

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doi: 10.16438/j.0513-4870.2025-1025
  • 接收时间：2025-08-28
  • 首发时间：2026-09-20
  • 出版时间：2025-12-12
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  • 收稿日期：2025-08-28
  • 修回日期：2025-10-23
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    1济南大学生物科学与技术学院, 山东 济南 250022
    2青岛市市立医院, 山东 青岛 266011

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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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