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Article(id=1308840483464508078, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840287129141340, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2025-0951, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1754928000000, receivedDateStr=2025-08-12, revisedDate=1765123200000, revisedDateStr=2025-12-08, acceptedDate=null, acceptedDateStr=null, onlineDate=1789981488338, onlineDateStr=2026-09-21, pubDate=1775923200000, pubDateStr=2026-04-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789981488338, onlineIssueDateStr=2026-09-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789981488338, creator=13701087609, updateTime=1789981488338, updator=13701087609, issue=Issue{id=1308840287129141340, tenantId=1146029695717560320, journalId=1189982191388893191, year='2026', volume='61', issue='4', pageStart='1001', pageEnd='1434', issueExtLink='null', onlineDate='null', pubDate='1775923200000', pubDateStr='2026-04-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789981441528, creator='13701087609', updateTime=1789984228828, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308851977992368434, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840287129141340, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308851977992368435, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308840287129141340, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=1294, endPage=1300, ext={EN=ArticleExt(id=1308840483686806192, articleId=1308840483464508078, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=A new neuroprotective isocoumarin from the marine-derived fungus Phaeosphaeriopsis sp. WP-26, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

To further clarify the neuroprotective active components of the marine-derived fungus Phaeosphaeriopsis sp. WP-26, the extract from its rice medium fermentation product was isolated and purified using various column chromatography techniques and high-performance liquid chromatography (HPLC). Nine compounds, including 5 isocoumarin monomers and 4 isocoumarin dimers, were isolated from the extract of the fermentation product of Phaeosphaeriopsis sp. WP-26. The chemical structures of the compounds were elucidated via NMR experiments, high-resolution mass spectrometry analysis, X-ray diffraction analysis, and comparison with the literature. Their structures were identified as phaeosphaerin F (1), 4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one (2), 6-demethylkigelin (3), (3R)-6, 7-dimethoxymellein (4), lignicol (5), spegazmarin C (6), spegazmarin D (7), spegazmarin E (8), and spegazmarin F (9). Among them, compound 1 is a new isocoumarin derivative, and compounds 2, 6-9 were isolated from fungi of the genus Phaeosphaeriopsis for the first time. Compounds 1-9 exhibited neuroprotective effects to varying degrees against H2O2-induced SH-SY5Y cell damage.

, authors=Ying WANG, Li-man ZHOU, Kun LENG, Cong WANG, Pei WANG*, authorsList=Ying WANG, Li-man ZHOU, Kun LENG, Cong WANG, Pei WANG, authorCompany=null, correspAuthors=Pei WANG, 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=1308840486576681658, articleId=1308840483464508078, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=海洋拟暗球腔菌Phaeosphaeriopsis sp. WP-26中的一个新异香豆素及其神经保护活性, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

为进一步阐明海洋拟暗球腔菌Phaeosphaeriopsis sp. WP-26的神经保护活性成分, 本研究采用多种柱色谱及高效液相色谱技术, 对菌株Phaeosphaeriopsis sp. WP-26的大米培养基发酵产物提取物进行分离纯化。运用核磁共振波谱、高分辨质谱及X射线单晶衍射等结构鉴定方法并结合文献数据比对, 对单体化合物的化学结构进行鉴定。本研究从目标菌株代谢产物中共分离获得了9个单体化合物, 包括5个异香豆素单体和4个异香豆素二聚体, 分别鉴定为: phaeosphaerin F (1)、4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one (2)、6-demethylkigelin (3)、(3R)-6, 7-dimethoxymellein (4)、lignicol (5)、spegazmarin C (6)、spegazmarin D (7)、spegazmarin E (8)、spegazmarin F (9), 其中化合物1为新化合物, 化合物2、6~9为首次分离自拟暗球腔菌属(Phaeosphaeriopsis) 真菌。化合物1~9对H2O2诱导损伤的SH-SY5Y细胞具有不同程度的保护作用。

, authors=王颖, 周丽曼, 冷坤, 王聪, 王佩*, authorsList=王颖, 周丽曼, 冷坤, 王聪, 王佩, authorCompany=null, correspAuthors=王佩, authorNote=

作者贡献:

王颖是本文第一作者, 负责化合物分离、结构鉴定、活性测定和论文撰写; 周丽曼参与本文的活性测定; 冷坤参与菌株的活化与发酵; 王聪参与本文化合物分离部分实验指导; 王佩是本文通讯作者, 负责实验指导和稿件修改工作。

, correspAuthorsNote=
王佩, E-mail:
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PositionδHδC
1169.9, C
34.88 (1H, m)77.3, CH
45.43 (1H, d, J = 2.1 Hz)55.8, CH
5112.4, C
6162.3a, C
76.51 (1H, s)105.0, CH
8163.9a, C
9100.9, C
10140.0, C
3-CH31.59 (3H, d, J = 6.4 Hz)18.0, CH3
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1H (400 MHz) and 13C (100 MHz) NMR data of compound 1 in CD3OD. aInterchangeable

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PositionδHδC
1169.9, C
34.88 (1H, m)77.3, CH
45.43 (1H, d, J = 2.1 Hz)55.8, CH
5112.4, C
6162.3a, C
76.51 (1H, s)105.0, CH
8163.9a, C
9100.9, C
10140.0, C
3-CH31.59 (3H, d, J = 6.4 Hz)18.0, CH3
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海洋拟暗球腔菌Phaeosphaeriopsis sp. WP-26中的一个新异香豆素及其神经保护活性
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王颖 , 周丽曼 , 冷坤 , 王聪 , 王佩 *
药学学报 | 研究论文 2026,61(4): 1294-1300
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药学学报 |研究论文 2026 , 61 (4) : 1294 -1300
海洋拟暗球腔菌Phaeosphaeriopsis sp. WP-26中的一个新异香豆素及其神经保护活性
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王颖, 周丽曼, 冷坤, 王聪, 王佩*
作者信息
  • 广西民族大学化学化工学院, 林产化学与工程国家民委重点实验室, 广西林产化学与工程重点实验室, 林木生物质低碳高质利用广西高校工程研究中心, 广西 南宁 530006
通讯作者:
王佩, E-mail:
作者简介:

作者贡献:

王颖是本文第一作者, 负责化合物分离、结构鉴定、活性测定和论文撰写; 周丽曼参与本文的活性测定; 冷坤参与菌株的活化与发酵; 王聪参与本文化合物分离部分实验指导; 王佩是本文通讯作者, 负责实验指导和稿件修改工作。

A new neuroprotective isocoumarin from the marine-derived fungus Phaeosphaeriopsis sp. WP-26
Ying WANG, Li-man ZHOU, Kun LENG, Cong WANG, Pei WANG*
Affiliations
  • Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission, Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Engineering Research Center of Low-Carbon and High-Quality Utilization of Forest Biomass, University of Guangxi, School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China
出版时间: 2026-04-12 doi: 10.16438/j.0513-4870.2025-0951
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摘要
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为进一步阐明海洋拟暗球腔菌Phaeosphaeriopsis sp. WP-26的神经保护活性成分, 本研究采用多种柱色谱及高效液相色谱技术, 对菌株Phaeosphaeriopsis sp. WP-26的大米培养基发酵产物提取物进行分离纯化。运用核磁共振波谱、高分辨质谱及X射线单晶衍射等结构鉴定方法并结合文献数据比对, 对单体化合物的化学结构进行鉴定。本研究从目标菌株代谢产物中共分离获得了9个单体化合物, 包括5个异香豆素单体和4个异香豆素二聚体, 分别鉴定为: phaeosphaerin F (1)、4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one (2)、6-demethylkigelin (3)、(3R)-6, 7-dimethoxymellein (4)、lignicol (5)、spegazmarin C (6)、spegazmarin D (7)、spegazmarin E (8)、spegazmarin F (9), 其中化合物1为新化合物, 化合物2、6~9为首次分离自拟暗球腔菌属(Phaeosphaeriopsis) 真菌。化合物1~9对H2O2诱导损伤的SH-SY5Y细胞具有不同程度的保护作用。

海洋真菌  /  拟暗球腔菌属  /  异香豆素  /  异香豆素二聚体  /  神经保护活性

To further clarify the neuroprotective active components of the marine-derived fungus Phaeosphaeriopsis sp. WP-26, the extract from its rice medium fermentation product was isolated and purified using various column chromatography techniques and high-performance liquid chromatography (HPLC). Nine compounds, including 5 isocoumarin monomers and 4 isocoumarin dimers, were isolated from the extract of the fermentation product of Phaeosphaeriopsis sp. WP-26. The chemical structures of the compounds were elucidated via NMR experiments, high-resolution mass spectrometry analysis, X-ray diffraction analysis, and comparison with the literature. Their structures were identified as phaeosphaerin F (1), 4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one (2), 6-demethylkigelin (3), (3R)-6, 7-dimethoxymellein (4), lignicol (5), spegazmarin C (6), spegazmarin D (7), spegazmarin E (8), and spegazmarin F (9). Among them, compound 1 is a new isocoumarin derivative, and compounds 2, 6-9 were isolated from fungi of the genus Phaeosphaeriopsis for the first time. Compounds 1-9 exhibited neuroprotective effects to varying degrees against H2O2-induced SH-SY5Y cell damage.

marine-derived fungus  /  Phaeosphaeriopsis  /  isocoumarin  /  isocoumarin dimer  /  neuroprotective activity
王颖, 周丽曼, 冷坤, 王聪, 王佩. 海洋拟暗球腔菌Phaeosphaeriopsis sp. WP-26中的一个新异香豆素及其神经保护活性. 药学学报, 2026 , 61 (4) : 1294 -1300 . DOI: 10.16438/j.0513-4870.2025-0951
Ying WANG, Li-man ZHOU, Kun LENG, Cong WANG, Pei WANG. A new neuroprotective isocoumarin from the marine-derived fungus Phaeosphaeriopsis sp. WP-26[J]. Acta Pharmaceutica Sinica, 2026 , 61 (4) : 1294 -1300 . DOI: 10.16438/j.0513-4870.2025-0951
正文
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海洋作为地球上最大的生态系统, 孕育着地球上80%的生物群落。其高盐高压、低温、缺氧、寡营养等特殊环境及其中不同物种间复杂的生态作用, 使海洋生物进化出了有别于陆地生物的适应机制和代谢途径, 能产生结构新颖、生物活性多样的次级代谢产物, 成为新药发现的重要来源[1-5]。作为海洋生物的重要成员, 海洋真菌广泛分布于海洋动物、植物、沉积物及海水等多种海洋环境中, 因其次生代谢产物具有结构多样性丰富、生物活性广泛等特点, 在活性天然产物的研究与开发中占据重要地位[6]。
拟暗球腔菌属(Phaeosphaeriopsis) 是Câmara等[7]在2003年建立的真菌新属。该属真菌自发现以来, 研究多集中于生物分类学及植物保护等领域[8-11], 而其次生代谢产物的研究相对较少。直至2022年, Zhong等[12]首次报道了该属真菌的次生代谢产物, 截至目前相关研究仅见4篇报道[12-15]。这些研究从该属真菌次生代谢产物中分离得到了多个结构新颖的化合物, 包括聚酮类[12, 13]、倍半萜类[14]、肽类[14]等多种结构类型, 部分化合物表现出α-葡萄糖苷酶抑制活性[12]和神经保护活性[13]。因此, 拟暗球腔菌属真菌的次生代谢产物具有进一步挖掘的价值。课题组前期从分离自南海海螺共附生真菌中筛选获得了一株拟暗球腔菌属真菌Phaeosphaeriopsis sp. WP-26, 从其大米培养基发酵产物提取物中分离鉴定了一系列新的异香豆素类化合物, 且表现出一定的神经保护活性[13]。为了进一步挖掘该菌株的神经保护活性成分, 本次研究在前期研究基础上, 继续对菌株Phaeosphaeriopsis sp. WP-26的大米培养基发酵产物进行研究, 共分离鉴定了1个新异香豆素类化合物(1) 和8个已知化合物(2~9, 图1)。本文将介绍这些化合物的分离纯化、结构鉴定及神经保护活性。
结果与讨论
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1　菌株来源
目标菌株分离自中国南海西沙群岛鸭公岛红娇凤凰螺(Strombus luhuanus Linnaeus)[13]。以引物ITS1 (5′-TCCGTAGGTGAACCTGCGG-3′) 及ITS4 (5′-TCC TCCGCTTATTGATATGC-3′) 对菌株ITS序列进行PCR扩增测序。将序列提交至NCBI中BLAST数据库进行同源比对, 鉴定为拟暗球腔菌属真菌(Phaeosphaeriopsis)[13]。菌种现保藏于广西民族大学, 保存编号为WP-26。
2　化合物结构鉴定
化合物1为无色晶体。高分辨电喷雾电离质谱(HR-ESI-MS) 在m/z 262.987 9 [M+H]⁺(计算值C10H9Cl2O4+, 262.987 2)、264.985 0 [M+2+H]⁺及266.983 9 [M+4+H]⁺处给出准分子离子峰, 其强度比为9∶6∶1, 该同位素分布特征提示化合物1含两个氯原子, 结合1D NMR数据, 推测其分子式为C10H8Cl2O4。分析化合物1的1H NMR、13C NMR及HSQC数据, 提示在δC/H (105.0/6.51) 处存在一个sp2杂化的次甲基信号, 在δC/H (55.8/5.43) 和δC/H (77.3/4.88) 处分别存在一个含氯次甲基和含氧次甲基信号, 在δC/H (18.0/1.59) 处存在一个甲基信号。除此以外, 还存在5个芳香季碳(δC 163.9、162.3、140.0、112.4、100.9) 和一个酯羰基碳(δC 169.9)。以上数据结合HMBC谱中H-7 (δH 6.51, s) 与C-5 (δC 112.4)、C-6 (δC 162.3/163.9)、C-8 (δC 162.3/163.9) 和C-9 (δC 100.9) 之间的相关信号, H-4 (δH 5.43, J = 2.1 Hz) 与C-5、C-9和C-10 (δC 140.0) 之间的相关信号, 3-CH3 (δH 1.59, d, J = 6.4 Hz) 与C-3 (δC 77.3) 和C-4 (δC 55.8) 之间的相关信号, 以及H-4和3-CH3与H-3之间的1H-1H COSY相关信号(图2), 提示化合物1含有异香豆素骨架[13]。以上数据与已知化合物4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one[16]的核磁数据十分相似, 二者不同在于化合物1中C-5的sp2杂化的季碳信号(δC 112.4) 取代了化合物4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one中C-5位的sp2杂化的次甲基信号(δC/H 107.4/6.36)[16]。结合H-3和H-4之间的1H-1H COSY相关信号, HMBC谱中H-4和H-7与C-5和C-9之间的相关信号, 及化合物1的分子式, 提示化合物1结构为化合物4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one中H-5被Cl原子取代, X-射线单晶衍射(图3) 结果进一步证实了化合物1的结构, 同时说明化合物1的绝对构型为3R和4R。综上所述, 化合物1的结构被鉴定如图1, 命名为phaeosphaerin F, 通过文献检索其结构未见报道, 因此, 化合物1为新化合物。
通过波谱数据分析结合文献检索, 已知化合物2~9结构分别鉴定为: 4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one (2)[16]、6-demethylkigelin (3)[15]、(3R)-6, 7-dimethoxymellein (4)[17]、lignicol (5)[18]、spegazmarin C (6)[19]、spegazmarin D (7)[19]、spegazmarin E (8)[19]、spegazmarin F (9)[19]。
3　H2O2诱导SH-SY5Y细胞损伤保护作用评价
本次研究对化合物1~9的H2O2诱导SH-SY5Y细胞损伤保护作用进行测试。结果表明(图4), H2O2处理后的细胞存活率明显降低至32% ± 4%, 对照组的细胞存活率为100%。化合物1、2、6~8在所有测试浓度下均对H2O2诱导SH-SY5Y细胞损伤细胞具有保护作用, 其中化合物1的活性与阳性对照Trolox相近, 化合物7和8的活性优于阳性对照。而化合物3~5、9在50.0 μmol·L-1浓度下, 对H2O2诱导SH-SY5Y细胞损伤具有保护作用, 其中化合物4和9分别在25.0和12.5 μmol·L-1也表现出一定的活性。化合物2、4和8对H2O2诱导SH-SY5Y细胞损伤的保护作用具有浓度依赖性。以上结果与模型组(H2O2组) 比较差异有统计学意义(P < 0.05)。
实验部分
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Primaide 1430分析型高效液相色谱仪, 日立仪器(大连) 有限公司; ProStar 210半制备型高效液相, 美国瓦里安医疗系统; HCB-1300V超净工作台, 青岛海尔特种电器有限公司; Bruker AV-400 M型超导核磁仪, 德国布鲁克公司; Cary 60 UV-Vis紫外分析仪, 美国安捷伦科技有限公司; LabServ K3 TOUCH型酶标仪, 美国赛默飞世尔科技公司; Sephadex LH-20 (批号: 20240624) 购自台州市路桥四甲生化塑料厂; C18反相填料(批号: YS250304PLX-H1) 购自麦可旺志(海南) 科技有限公司; 柱色谱硅胶(批号: 0240183) 和薄层色谱硅胶板GF254 (批号: 20250402) 均购自青岛海洋化工集团公司; 分析型C18色谱柱(COSMOSIL C18, 250 mm × 4.6 mm, 5 μm) 和半制备型C18色谱柱(COSMOSIL C18, 250 mm × 10 mm, 5 μm), 日本Nacalai Tesque株式会社; 三氟乙酸试剂(批号: C17882106) 购自上海麦克林生化科技股份有限公司; SH-SY5Y神经细胞(批号: FH0156) 购自上海富衡生物科技有限公司。
1　菌株培养与发酵
在无菌条件下, 用接种环将目标菌株接种于含有PDA培养基(马铃薯200.0 g, 葡萄糖20.0 g, NaCl 33.0 g, 琼脂15.0 g, 去离子水1.0 L) 的无菌培养皿中进行活化, 置于28 ℃恒温培养箱中培养7天。待目标菌株活化完成后, 在无菌条件下, 挑取黄豆大菌落置于含有150 mL PDB培养基(马铃薯200.0 g, 葡萄糖20.0 g, NaCl 33.0 g, 去离子水1.0 L) 的500 mL三角瓶中, 置于28 ℃, 转速为180 r·min-1的摇床中培养3天, 获得菌株发酵种子液。向装有大米培养基(50 g大米, 50 mL自来水) 的无菌发酵袋中接入5 mL发酵种子液, 共发酵500袋, 室温条件静置培养36天。
2　发酵产物的提取与分离
发酵完成后, 将发酵物转移至萃取容器中, 加入2倍发酵物体积乙酸乙酯, 充分混合, 浸提24 h后, 回收乙酸乙酯部分, 相同方法提取3次, 合并乙酸乙酯部分, 浓缩至干, 得到菌株发酵产物乙酸乙酯提取物253.1 g。将粗提物用90%甲醇水溶液悬浮后, 用等体积石油醚进行萃取, 得到石油醚层180.0 g, 甲醇层67.7 g。
甲醇层(67.7 g) 经减压正相硅胶柱色谱, 以氯仿-甲醇(1∶0→0∶1) 为洗脱剂梯度洗脱, 经TLC和HPLC分析后, 合并共得到15个组分(Fr.1~Fr.15)。Fr.1 (3.20 g) 以甲醇-水(1∶4→0∶1) 为洗脱剂, 经反相硅胶柱色谱梯度分离, 经TLC和HPLC分析合并得到17个组分(Fr.1.1~Fr.1.17)。Fr.1.10 (53.1 mg) 经半制备高效液相色谱, 通过C18色谱柱制备, 以45%甲醇水溶液(水相含0.1%三氟乙酸) 为洗脱剂洗脱, 获得化合物1 (7.3 mg, tR = 26.2 min)。Fr.1.7 (103.5 mg) 经半制备高效液相色谱分离, 采用C18色谱柱, 以40%甲醇水溶液(水相含0.1%三氟乙酸) 为洗脱剂洗脱, 得到化合物3 (62.0 mg, tR = 16.2 min)。Fr.1.9 (103.8 mg) 通过C18色谱柱, 经半制备高效液相色谱分离, 以45%甲醇水溶液(水相含0.1%三氟乙酸) 为洗脱剂洗脱, 得到化合物2 (1.5 mg, tR = 20.8 min)、化合物6 (13.5 mg, tR = 29.8 min) 和化合物7 (11.7 mg, tR =14.8 min)。Fr.2 (10.2 g) 经加压反相硅胶柱色谱, 以甲醇-水(1∶3→0∶1) 为洗脱剂梯度洗脱, 经TLC和HPLC分析后, 合并得到19个组分(Fr.2.1~Fr.2.19)。Fr.2.4 (271.0 mg) 经Sephadex LH-20凝胶柱色谱, 以甲醇为洗脱剂, 经TLC分析合并得到4个组分(Fr.2.4.1~Fr.2.4.4)。Fr.2.4.2 (35.2 mg) 经高效液相色谱, 以40%甲醇水溶液(水相含0.1%三氟乙酸) 为洗脱剂, 通过C18半制备色谱柱进行分离, 得到化合物4 (8.3 mg, tR = 20.5 min)。Fr.2.8 (51.5 mg) 经Sephadex LH-20凝胶柱色谱, 以甲醇洗脱后, 合并得到5个组分(Fr.2.8.1~Fr.2.8.5)。Fr.2.8.3 (20.2 mg) 经高效液相色谱, 以20%乙腈水溶液(水相含0.1%三氟乙酸) 为洗脱剂, 通过C18半制备色谱柱进行分离, 得到化合物5 (3.2 mg, tR = 7.2 min)。Fr.2.6 (219.5 mg) 经高效液相色谱C18半制备色谱柱分离, 以30%乙腈水溶液(水相含0.1%三氟乙酸) 为洗脱剂, 获得化合物9 (7.2 mg, tR = 7.5 min)。Fr.3 (8.62 g) 经加压反相柱色谱, 以甲醇-水(1∶3→0∶1) 为洗脱剂梯度洗脱, 经TLC和HPLC分析后, 合并得到12个组分(Fr.3.1~Fr.3.12)。Fr.3.5 (93.5 mg) 经半制备型高效液相色谱, 通过C18半制备色谱柱进行分离, 以50%甲醇水溶液(水相含0.1%三氟乙酸) 为洗脱剂洗脱, 获得化合物8 (14.6 mg, tR = 14.5 min)。
3　化合物结构鉴定
化合物1 (phaeosphaerin F): 无色晶体, 易溶于甲醇; mp 182~183 ℃; [α]$ {}_{\mathrm{D}}^{25} $ 22.67 (c 0.1, CH3OH), UV (MeOH) λmax (log ε) 221 (3.96), 267 (3.53), 323 (3.40) nm; 1H NMR (400 MHz, CD3OD) 和13C NMR (100 MHz, CD3OD) 见表1; HR-ESI-MS: m/z 262.987 9 [M+H]⁺(计算值C10H9Cl2O4+, 262.987 2)、264.985 0 [M+2+H]⁺及266.983 9 [M+4+H]⁺, 其强度比为9∶6∶1。
化合物2 (4-chloro-6, 8-dihydroxy-3-methylisochroman-1-one): 白色粉末, ESI-MS: m/z 229.1 [M+H]+, 231.1 [M+H+2]+, 其强度比为3∶1; 1H NMR (400 MHz, CD3OD): δH 6.43 (1H, d, J = 2.2 Hz, H-5), 6.34 (1H, d, J = 2.2 Hz, H-7), 5.13 (1H, d, J = 1.5 Hz, H-4), 4.60 (1H, br s, H-3), 1.55 (3H, d, J = 6.3 Hz, 3-CH3); 13C NMR (100 MHz, CD3OD): δC 170.3 (C, C-1), 77.6 (CH, C-3), 58.5 (CH, C-4), 108.4 (CH, C-5), 165.7 (C, C-6), 104.3 (CH, C-7), 166.3 (C, C-8), 99.9 (C, C-9), 143.5 (C, C-10), 18.1 (CH3, 3-CH3)。
化合物3 (6-demethylkigelin): 黄色粉末, ESI-MS m/z 247.0 [M+Na]+, 分子式C11H12O5, [α]$ {}_{\mathrm{D}}^{25} $ -22.4 (c 0.1, CH3OH)。1H NMR (400 MHz, CD3OD): δH 6.28 (1H, s, H-5), 4.65 (1H, m, H-3), 3.81 (3H, s, 7-OCH3), 2.81 (2H, m, H-4), 1.45 (3H, d, J = 6.3 Hz, 3-CH3); 13C NMR (100 MHz, CD3OD): δC 171.9 (C, C-1), 77.6 (CH, C-3), 35.1 (CH2, C-4), 107.8 (CH, C-5), 157.6 (C, C-6), 135.0 (C, C-7), 158.3 (C, C-8), 102.2 (C, C-9), 137.5 (C, C-10), 60.9 (CH3, 7-OCH3), 20.8 (CH3, 3-CH3)。
化合物4 [(3R)-6, 7-dimethoxymellein]: 黄色粉末, ESI-MS m/z 261.1 [M+Na]+, 分子式C12H14O5, [α]$ {}_{\mathrm{D}}^{25} $ 76.3 (c 0.7, CH3OH); 1H NMR (400 MHz, CD3OD): δH 6.53 (1H, s, H-5), 4.70 (1H, m, H-3), 3.91 (3H, s, 7-OCH3), 3.79 (3H, s, 6-OCH3), 2.98 (1H, dd, J = 16.5, 3.6 Hz, H-4a), 2.87 (1H, dd, J = 16.5, 11.3 Hz, H-4b), 1.48 (3H, d, J = 6.3 Hz, 3-CH3); 13C NMR (100 MHz, CD3OD): δC 171.6 (C, C-1), 77.7 (CH, C-3), 35.3 (CH2, C-4), 103.7 (CH, C-5), 160.1 (C, C-6), 136.0 (C, C-7), 156.9 (C, C-8), 101.4 (C, C-9), 138.0 (C, C-10), 60.9 (CH3, 7-OCH3), 56.7 (CH3, 6-OCH3), 20.8 (CH3, 3-CH3)。
化合物5 (lignicol): 白色形粉末, ESI-MS m/z 263.0 [M+Na]+, 分子式为C11H12O6; 1H NMR (400 MHz, CD3OD): δH 6.60 (1H, s, H-5), 4.45 (1H, m, H-3), 4.44 (1H, m, H-4), 3.83 (3H, s, 7-OCH3), 1.44 (3H, d, J = 6.1 Hz, 3-CH3); 13C NMR (100 MHz, CD3OD): δC 170.5 (C, C-1), 81.4 (CH, C-3), 69.5 (CH, C-4), 106.6 (CH, C-5), 158.9 (C, C-6/8), 135.7 (C, C-7), 157.5 (C, C-6/8), 100.9 (C, C-9), 140.3 (C, C-10), 60.9 (CH3, 7-OCH3), 18.2 (CH3, 3-CH3)。
化合物6 (spegazmarin C): 无色晶体, ESI-MS m/z 519.1 [M+Na]+, 521.1 [M+Na+2]+, 其强度比为3∶1; 分子式为C22H21ClO11, [α]$ {}_{\mathrm{D}}^{25} $ +159 (c 0.01, CH3OH); 1H NMR (400 MHz, CDCl3): δH 11.45 (1H, s, 8′-OH), 11.40 (1H, s, 8-OH), 6.44 (1H, s, H-5), 5.34 (1H, d, J = 1.8 Hz, H-4), 5.09 (1H, qd, J = 6.8, 1.8 Hz, H-3), 4.83 (1H, J = 1.8 Hz, H-4′), 4.61 (1H, qd, J = 6.6, 1.7 Hz, H-3′), 4.01 (3H, s, 7-OCH3), 3.95 (3H, s, 7′-OCH3), 1.62 (3H, d, J = 6.5 Hz, 3′-CH3), 1.36 (3H, d, J = 6.9 Hz, 3-CH3); 13C NMR (100 MHz, CDCl3): δC 167.6 (C, C-1), 77.6 (CH, C-3), 78.2 (CH, C-4), 108.1 (CH, C-5), 154.9 (C, C-6), 135.2 (C, C-7), 155.4 (C, C-8), 101.7 (C, C-9), 130.1 (C, C-10), 61.0 (CH3, 7-OCH3), 17.8 (CH3, 3-CH3), 168.8 (C, C-1′), 78.1 (CH, C-3′), 64.1 (CH, C-4′), 118.1 (C, C-5′), 151.7 (C, C-6′), 142.6 (C, C-7′), 156.0 (C, C-8′), 105.1 (C, C-9′), 133.3 (C, C-10′), 61.3 (CH3, 7′-OCH3), 16.1 (CH3, 3′-CH3)。
化合物7 (spegazmarin D): 白色无定形粉末, 分子式为C22H21ClO11, [α]$ {}_{\mathrm{D}}^{25} $ -227.0 (c 0.10, MeOH), ESI-MS m/z 519.1 [M+Na]+, 521.1 [M+Na+2]+, 其强度比为3∶1; 1H NMR (400 MHz, CD3OD): δH 6.03 (1H, s, H-5), 5.49 (1H, d, J = 1.5 Hz, H-4), 4.90 (1H, m, H-3), 4.69 (1H, d, J = 1.8 Hz, H-4′), 4.57 (1H, qd, J = 6.5, 1.8 Hz, H-3′), 3.92 (3H, s, 7′-OCH3), 3.79 (3H, s, 7-OCH3), 1.76 (3H, d, J = 6.6 Hz, 3-CH3), 1.48 (3H, d, J = 6.6 Hz, 3′-CH3); 13C NMR (100 MHz, CD3OD): δC 170.9 (C, C-1), 78.9 (CH, C-3), 77.1 (CH, C-4), 109.5 (CH, C-5), 156.5 (C, C-6), 137.2 (C, C-7), 157.7 (C, C-8), 102.2 (C, C-9), 133.6 (C, C-10), 61.5 (CH3, 7-OCH3), 16.9 (CH3, 3-CH3), 170.5 (C, C-1′), 79.7 (CH, C-3′), 64.6 (CH, C-4′), 119.5 (C, C-5′), 152.5 (C, C-6′), 143.8 (C, C-7′), 157.5 (C, C-8′), 106.6 (C, C-9′), 135.2 (C, C-10′), 60.9 (CH3, 7′-OCH3), 16.4 (CH3, 3′-CH3)。
化合物8 (spegazmarin E): 黄色粉末, ESI-MS m/z 519.1 [M+Na]+, 521.1 [M+Na+2]+, 其强度比为3∶1; 分子式为C22H21ClO11。1H NMR (400 MHz, CDCl3): δH 11.51 (1H, s, 8′-OH), 11.36 (1H, s, 8-OH), 6.06 (1H, s, H-5), 5.36 (1H, br s, H-4), 4.94 (1H, q, J = 6.9 Hz, H-3′), 4.85 (1H, q, J = 6.6 Hz, H-3), 4.80 (1H, br s, H-4′), 3.95 (6H, s, 7/7′-OCH3), 1.80 (3H, d, J = 6.6 Hz, 3-CH3), 1.27 (3H, d, J = 6.7 Hz, 3′-CH3); 13C NMR (100 MHz, CDCl3): δC 169.2 (C, C-1), 77.3 (CH, C-3), 76.2 (CH, C-4), 107.1 (CH, C-5), 154.5 (C, C-6), 135.4 (C, C-7), 156.0 (C, C-8), 102.1 (C, C-9), 131.9 (C, C-10), 61.4 (CH3, 7-OCH3), 16.7 (CH3, 3-CH3), 167.3 (C, C-1′), 80.5 (CH, C-3′), 65.5 (CH, C-4′), 119.7 (C, C-5′), 151.8 (C, C-6′), 143.1 (C, C-7′), 155.7 (C, C-8′), 105.0 (C, C-9′), 130.9 (C, C-10′), 61.1 (CH3, 7′-OCH3), 18.2 (CH3, 3′-CH3)。
化合物9 (spegazmarin F): 粉色油状, ESI-MS m/z 519.1 [M+Na]+, 521.1 [M+Na+2]+, 其强度比为3∶1; 分子式为C22H21ClO11, [α]$ {}_{\mathrm{D}}^{25} $ 113.6 (c 0.20, CH3OH); 1H NMR (400 MHz, CDCl3): δH 11.47 (1H, s, 8′-OH), 11.39 (1H, s, 8-OH), 6.36 (1H, s, H-5), 5.33 (1H, br s, H-4), 5.12 (1H, q, J = 6.8 Hz, H-3), 4.95 (1H, q, J = 6.4 Hz, H-3′), 4.85 (1H, br s, H-4′), 3.98 (3H, s, 7-OCH3), 3.96 (3H, s, 7′-OCH3), 1.35 (3H, d, J = 6.7 Hz, 3-CH3), 1.24 (3H, d, J = 6.4 Hz, 3′-CH3); 13C NMR (100 MHz, CDCl3): δC 167.8 (C, C-1), 77.9 (CH, C-3), 78.1 (CH, C-4), 108.3 (CH, C-5), 154.8 (C, C-6), 135.3 (C, C-7), 155.5 (C, C-8), 101.9 (C, C-9), 130.1 (C, C-10), 61.3 (CH3, 7-OCH3), 17.9 (CH3, 3-CH3), 167.4 (C, C-1′), 80.5 (CH, C-3′), 65.5 (CH, C-4′), 119.2 (C, C-5′), 151.7 (C, C-6′), 142.9 (C, C-7′), 156.0 (C, C-8′), 105.1 (C, C-9′), 131.0 (C, C-10′), 61.0 (CH3, 7′-OCH3), 18.0 (CH3, 3′-CH3)。
化合物1的晶体结构数据: 化合物1的晶体数据通过XtaLAB Synergy系列单晶衍射仪收集, 采用Cu Kα辐射(λ = 1.541 84 Å), 并经石墨单色器单色化。化合物1在甲醇中培养获得晶体, 为无色针状晶体, 分子式为C10H8Cl2O4, 正交晶系, 空间群为C2221; 晶胞参数a = 6.566 7 (1) Å, b = 15.536 0 (2) Å, c = 21.602 6 (3), α = 90.00°, β = 90.00 (15)°, γ = 90.00°; 体积V = 2 203.92 (7) Å3, Z = 8; Dcalc = 1.586 g·cm-3; μ (Cu Kα) = 5.300 mm-1; F (000) = 1 072.0; 晶体尺寸0.3×0.2×0.1 mm3; T = 293.00 K; R1 = 0.035 6 (I > 2σ (I)), wR2 = 0.091 5 (all data); 收集的衍射点为11 341; 独立衍射点2 195 (Rint = 0.048 8, Rsigma = 0.028 5); GOOF值为1.075; Flack参数为-0.001 (8)。本文中化合物1的晶体学数据已存放在剑桥晶体数据库中心, 存储编号为CCDC 2479010。
4　H2O2诱导SH-SY5Y细胞损伤保护作用评价
实验参照MTT[20]法, 将待测试样品用DMSO溶解, 配置成浓度为20.0 mmol·L-1的溶液, 在此基础上用细胞培养液将其稀释分别至50.0、25.0和12.5 μmol·L-1。用含10%胎牛血清的培养液培养人神经母细胞瘤SH-SY5Y细胞, 取对数期细胞以每毫升2.5×104个浓度接种于96孔板, 设置对照组、H2O2模型组、阳性对照(Trolox) 及样品组, 置于CO2培养箱中培养36 h后弃去上清, 样品组与阳性对照组分别加入不同浓度的含药培养液, 其余组加入正常培养液, 培养12 h后, 除对照组外, 各组均加入终浓度为2 000 μmol·L-1 H2O2溶液, 继续培养12 h后, 每孔加入5.0 mg·mL-1 MTT溶液20 μL, 37 ℃避光孵育4 h, 弃培养基上清, 加入100 μL的DMSO, 振荡10 min, 在酶标仪492 nm波长下检测吸光度并计算存活率。实验组细胞存活率(%) = (OD实验组-OD空白) / (OD对照组-OD空白) × 100%。
5　统计学分析
本次研究活性实验数据采用SPSS 19.0软件进行分析, 所有数据均以3个独立实验的平均值± SD (标准差) 表示, 两组间数据的比较采用单因素方差分析(ANOVA) 进行差异分析, 当P < 0.05时, 差异具有统计显著性。

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doi: 10.16438/j.0513-4870.2025-0951
  • 接收时间：2025-08-12
  • 首发时间：2026-09-21
  • 出版时间：2026-04-12
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  • 收稿日期：2025-08-12
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    广西民族大学化学化工学院, 林产化学与工程国家民委重点实验室, 广西林产化学与工程重点实验室, 林木生物质低碳高质利用广西高校工程研究中心, 广西 南宁 530006

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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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