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Article(id=1256540740050608925, tenantId=1146029695717560320, journalId=1255847803461844995, issueId=1256540735885665031, articleNumber=null, orderNo=null, doi=10.13346/j.mycosystema.250283, pmid=null, cstr=32115.14.j.mycosystema.250283, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1759766400000, receivedDateStr=2025-10-07, revisedDate=null, revisedDateStr=null, acceptedDate=1762185600000, acceptedDateStr=2025-11-04, onlineDate=1777512257826, onlineDateStr=2026-04-30, pubDate=1769011200000, pubDateStr=2026-01-22, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1777512257826, onlineIssueDateStr=2026-04-30, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1777512257826, creator=13701087609, updateTime=1777512257826, updator=13701087609, issue=Issue{id=1256540735885665031, tenantId=1146029695717560320, journalId=1255847803461844995, year='2026', volume='45', issue='1', pageStart='250201', pageEnd='250283', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1777512256833, creator=13701087609, updateTime=1777512529110, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1256541877973693171, tenantId=1146029695717560320, journalId=1255847803461844995, issueId=1256540735885665031, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1256541877973693172, tenantId=1146029695717560320, journalId=1255847803461844995, issueId=1256540735885665031, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=250283, endPage=, ext={EN=ArticleExt(id=1256540740897858345, articleId=1256540740050608925, tenantId=1146029695717560320, journalId=1255847803461844995, language=EN, title=Cadinane-type sesquiterpenes from Ganoderma subangustisporum and their α-glucosidase inhibitory activities, columnId=1256263562373226548, journalTitle=Mycosystema, columnName=Research paper, runingTitle=null, highlight=null, articleAbstract=

The chemical constituents of Ganoderma subangustisporum and their α-glucosidase inhibitory activity were investigated. Two cadinane-type sesquiterpenes, 17-hydroxy-12-ethoxycarbonyl-α-cadinol (1) and 12-hydroxy-α-cadinol (2), were isolated from the ethyl acetate extract of G. angustisporum mycelial cultures. Their structures were elucidated through high-resolution mass spectrometry, comprehensive nuclear magnetic resonance spectroscopic analysis and quantum chemical calculations. Compound 1 is novel due to the acetylation of its 12-hydroxy group, while compound 2 is reported for the first time from the genus Ganoderma. Both compounds 1 and 2 exhibited α-glucosidase inhibitory activity, with IC50 values of (96.72±3.87) μmol/L and (56.82±4.70) μmol/L, respectively. Molecular docking results indicate that compounds 1 and 2 primarily interact with key amino acid residues in the active site of α-glucosidase through hydrogen bonds.

, correspAuthors=Yuxi WANG, Haisheng YUAN, authorNote=null, correspAuthorsNote=
* WANG Yuxi, ;
YUAN Haisheng,
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ORCID: WANG Yuxi (0000-0002-7665-6474),

YUAN Haisheng (0000-0001-7056-140X)

, authorsList=Shiyuan MA, Yuxi WANG, Yulian WEI, Haisheng YUAN), CN=ArticleExt(id=1256540745494815592, articleId=1256540740050608925, tenantId=1146029695717560320, journalId=1255847803461844995, language=CN, title=亚窄孢灵芝中杜松烷型倍半萜及其α-葡萄糖苷酶抑制活性, columnId=1256263563312771301, journalTitle=菌物学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

本研究聚焦灵芝属物种亚窄孢灵芝Ganoderma subangustisporum的化学成分及其α-葡萄糖苷酶抑制活性分析。从亚窄孢灵芝菌丝体培养物中分离得到2个杜松烷型倍半萜类化合物：17-hydroxy-12-ethoxycarbonyl-α-cadinol (1)和12-hydroxy-α-cadinol (2)。通过高分辨质谱、核磁共振和量子化学计算确定了其结构。其中，化合物1为新化合物，其结构的新颖性在于12位羟基发生了乙酰化。化合物2为首次从灵芝属中分离。化合物1和2均表现出α-葡萄糖苷酶抑制活性，IC50值分别为(96.72±3.87)和(56.82±4.70) μmol/L，分子对接结果揭示化合物1和2主要通过氢键与α-葡萄糖苷酶活性位点的关键氨基酸残基相互作用。

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1H (600 MHz) and 13C (150 MHz) NMR spectroscopic data of compound 1 in CDCl3

, figureFileSmall=null, figureFileBig=null, tableContent=
位置
Position		 氢化学位移
δH (multi, J in Hz)		 碳化学位移
δC
1 1.28, m 50.2
2a 1.21, m 22.4
2b 1.26, m 22.4
3a 2.09, m, (6.36) 26.6
3b 2.12, m, (4.68) 26.6
4 - 138.9
5 5.72, s 122.9
6 1.82, m 39.1
7 1.80, m 42.0
8a 1.51, m. (3.48) 22.7
8b 1.53, m, (3.59) 22.7
9a 1.32, dt, (12.16, 3.40) 41.9
9b 1.45, m 41.9
10 - 72.2
11 2.35, qd, (7.13, 3.18) 31.3
12 3.96, d, (7.32) 68.5
13 - 171.4
14 1.12, s 20.8
15 0.84, d, (7.00) 10.5
16 2.06, s 21.2
17 4.03, m 67.4
), ArticleFig(id=1256540765174489126, tenantId=1146029695717560320, journalId=1255847803461844995, articleId=1256540740050608925, language=CN, label=表1, caption=

CDCl3中化合物1的1H (600 MHz)和13C (150 MHz) NMR数据

, figureFileSmall=null, figureFileBig=null, tableContent=
位置
Position		 氢化学位移
δH (multi, J in Hz)		 碳化学位移
δC
1 1.28, m 50.2
2a 1.21, m 22.4
2b 1.26, m 22.4
3a 2.09, m, (6.36) 26.6
3b 2.12, m, (4.68) 26.6
4 - 138.9
5 5.72, s 122.9
6 1.82, m 39.1
7 1.80, m 42.0
8a 1.51, m. (3.48) 22.7
8b 1.53, m, (3.59) 22.7
9a 1.32, dt, (12.16, 3.40) 41.9
9b 1.45, m 41.9
10 - 72.2
11 2.35, qd, (7.13, 3.18) 31.3
12 3.96, d, (7.32) 68.5
13 - 171.4
14 1.12, s 20.8
15 0.84, d, (7.00) 10.5
16 2.06, s 21.2
17 4.03, m 67.4
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亚窄孢灵芝中杜松烷型倍半萜及其α-葡萄糖苷酶抑制活性
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马世元 1, 2 , 王雨曦 1, * , 魏玉莲 1 , 袁海生 1, 2, *
菌物学报 | 研究论文 2026,45(1): 250283
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菌物学报 | 研究论文 2026, 45(1): 250283
亚窄孢灵芝中杜松烷型倍半萜及其α-葡萄糖苷酶抑制活性
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马世元1, 2, 王雨曦1, * , 魏玉莲1, 袁海生1, 2, *
作者信息
  • 1 中国科学院沈阳应用生态研究所 中国科学院森林生态与保育重点实验室，辽宁 沈阳 110164
  • 2 辽宁大学生命科学院，辽宁 沈阳 110036
Cadinane-type sesquiterpenes from Ganoderma subangustisporum and their α-glucosidase inhibitory activities
Shiyuan MA1, 2, Yuxi WANG1, * , Yulian WEI1, Haisheng YUAN1, 2, *
Affiliations
  • 1 CAS Key Laboratory of Forest Ecology and Silviculture, Institute of Applied Ecology, Chinese Academy of Sciences, Shenyang 110164, Liaoning, China
  • 2 College of Life Sciences, Liaoning University, Shenyang 110036, Liaoning, China

    • ORCID: WANG Yuxi (0000-0002-7665-6474),

    YUAN Haisheng (0000-0001-7056-140X)

出版时间: 2026-01-22 doi: 10.13346/j.mycosystema.250283
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摘要
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本研究聚焦灵芝属物种亚窄孢灵芝Ganoderma subangustisporum的化学成分及其α-葡萄糖苷酶抑制活性分析。从亚窄孢灵芝菌丝体培养物中分离得到2个杜松烷型倍半萜类化合物：17-hydroxy-12-ethoxycarbonyl-α-cadinol (1)和12-hydroxy-α-cadinol (2)。通过高分辨质谱、核磁共振和量子化学计算确定了其结构。其中，化合物1为新化合物，其结构的新颖性在于12位羟基发生了乙酰化。化合物2为首次从灵芝属中分离。化合物1和2均表现出α-葡萄糖苷酶抑制活性，IC50值分别为(96.72±3.87)和(56.82±4.70) μmol/L，分子对接结果揭示化合物1和2主要通过氢键与α-葡萄糖苷酶活性位点的关键氨基酸残基相互作用。

亚窄孢灵芝  /  化学成分  /  杜松烷型倍半萜  /  α-葡萄糖苷酶抑制活性  /  分子对接

The chemical constituents of Ganoderma subangustisporum and their α-glucosidase inhibitory activity were investigated. Two cadinane-type sesquiterpenes, 17-hydroxy-12-ethoxycarbonyl-α-cadinol (1) and 12-hydroxy-α-cadinol (2), were isolated from the ethyl acetate extract of G. angustisporum mycelial cultures. Their structures were elucidated through high-resolution mass spectrometry, comprehensive nuclear magnetic resonance spectroscopic analysis and quantum chemical calculations. Compound 1 is novel due to the acetylation of its 12-hydroxy group, while compound 2 is reported for the first time from the genus Ganoderma. Both compounds 1 and 2 exhibited α-glucosidase inhibitory activity, with IC50 values of (96.72±3.87) μmol/L and (56.82±4.70) μmol/L, respectively. Molecular docking results indicate that compounds 1 and 2 primarily interact with key amino acid residues in the active site of α-glucosidase through hydrogen bonds.

Ganoderma subangustisporum  /  chemical constituent  /  cadinane-type sesquiterpene  /  α-glucosidase inhibitory activity  /  molecular docking
马世元, 王雨曦, 魏玉莲, 袁海生. 亚窄孢灵芝中杜松烷型倍半萜及其α-葡萄糖苷酶抑制活性. 菌物学报, 2026 , 45 (1) : 250283 - . DOI: 10.13346/j.mycosystema.250283
Shiyuan MA, Yuxi WANG, Yulian WEI, Haisheng YUAN. Cadinane-type sesquiterpenes from Ganoderma subangustisporum and their α-glucosidase inhibitory activities[J]. Mycosystema, 2026 , 45 (1) : 250283 - . DOI: 10.13346/j.mycosystema.250283
正文
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灵芝Ganoderma spp.属于担子菌门Basidiomycota、多孔菌目Polyporales、多孔菌科Polyporaceae，是一类全球广泛分布的木生真菌(Cao et al. 2012；Wu et al. 2022；Zhao et al. 2024)。灵芝作为传统药食资源，富含多糖、三萜、倍半萜、甾体、生物碱及核苷类成分(张婧等 2020；董观海等 2022)，具有显著的免疫调节、抗肿瘤、抗糖尿病、抗氧化和血管保护活性(Luo et al. 2002；Fatmawati et al. 2010；Wu et al. 2012, 2019；Liang et al. 2019；滕李铭等2021；Liu et al. 2022；Liu et al. 2024)。这些药用特性使灵芝成为开发功能性食品、药品和保健品的重要原料。目前，灵芝研究主要聚焦于赤芝Ganoderma lucidum和紫芝G. sinense，而对灵芝属其他物种尚未充分挖掘。这些研究相对较少的物种，可能成为新型天然产物的重要来源(戴玉成2022)。亚窄孢灵芝是近年来Sun et al. (2022)发表的新物种，其主要特征为菌盖表面呈暗红色至近黑色，并生有由深色连续斑点构成的同心环带与放射状皱纹，菌盖边缘薄而锐利，担孢子较窄，呈椭球形，顶端平截。目前，关于其化学成分的系统研究及生物活性评价尚未见报道。
当前，灵芝化学成分的研究以三萜和多糖类为主(滕李铭等 2021)，近年来人们逐渐发现灵芝中的其他类型化合物也可能是其发挥生物活性的重要物质基础。如在倍半萜类成分中，杜松烷型倍半萜(cadinane sesquiterpenes)因其复杂的结构(如双环并环构型差异)和显著的生物活性，有望成为药物开发中新型分子的重要来源(姜龙瑜等 2021)。目前在植物和微生物中已鉴定出超过180种杜松烷型倍半萜类化合物，根据氧化修饰与环系重排程度可分为简单杜松醇类、芳环杜松烷类、内酯/内酰胺类、醛酮酸类及复杂衍生物五大类，其中真菌来源约占比26% (Huang et al. 2022；Liang et al. 2022；Cui et al. 2024；魏艳梅等 2024；Moreno-Gutiérrez et al. 2025)。
α-葡萄糖苷酶是小肠中负责水解α-葡萄糖苷键释放葡萄糖的关键酶，其活性直接影响餐后血糖水平(王道滇等 2024)。通过抑制α-葡萄糖苷酶的活性，能够有效延缓碳水化合物的消化与葡萄糖的吸收，从而平稳餐后血糖，这对2型糖尿病的防治具有重要意义(Zheng et al. 2024)。目前临床应用的α-葡萄糖苷酶抑制剂(如阿卡波糖)虽有效，但常伴随胃肠道不适等副作用(王道滇等 2025)。天然产物因其结构多样性和较高的安全性，成为寻找新颖α-葡萄糖苷酶抑制剂的重要来源。值得注意的是，杜松烷型倍半萜的α-葡萄糖苷酶抑制活性已初显潜力。例如，从山茱萸Cornus officinalis中分离的杜松烷苷类化合物cornucadinoside E的抑制活性接近于临床药物阿卡波糖(He et al. 2019)。
本研究对亚窄孢灵芝的化学成分及其α-葡萄糖苷酶抑制活性进行了分析，从中分离得到2个杜松烷型倍半萜类化合物。其中化合物1为新化合物，化合物2为首次从灵芝属中分离。两种化合物均表现出了一定程度的α-葡萄糖苷酶抑制活性。
1 材料与方法
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1.1 材料
1.1.1 实验材料
本研究所用亚窄孢灵芝标本于2019年采集于云南省红河哈尼族彝族自治州屏边县大围山国家森林公园，经形态和ITS序列(GenBank PX473037)鉴定为G. subangustisporum B.K. Cui, J.H. Xing & Y.F. Sun (Sun et al. 2022)，保存于中国科学院沈阳应用生态研究所东北生物标本馆。
1.1.2 试剂
乙腈(色谱纯，天津永大化学试剂公司)；甲醇(色谱纯，天津大茂化学试剂公司)；乙酸乙酯、石油醚、二氯甲烷、甲醇、乙醇(分析纯，天津永大化学试剂公司)；α-葡萄糖苷酶(批号RM20Y1225)、pNPG (批号RM20Y1118)、阿卡波糖(批号RT20U1210) (上海瑞永生物科技有限公司)。
1.1.3 仪器
Bruker 600型超导核磁共振光谱仪(Bruker公司)；LC-20AD岛津制备液相色谱仪、LC-20AT岛津制备液相色谱仪(岛津公司)；Agilent 1260高效液相色谱仪(安捷伦公司)；制备型色谱柱(250 mm × 20 mm, 10 μm)、半制备型色谱柱(250 mm × 10 mm, 5 μm) (YMC公司)；薄层析硅胶(青岛邦凯高新技术材料有限公司)。
1.2 提取和分离
将亚窄孢灵芝菌株在PDA培养基上扩大培养后，转入液体培养基制备种子培养液。取5 mL种子液接种于大米培养基，于28 ℃静置培养40 d，直至菌丝完全覆盖培养基。收集固体发酵物，加入乙酸乙酯，室温下浸泡提取(重复3次)。合并提取液，经旋转蒸发仪减压浓缩，获得灵芝浸膏170 g。该浸膏随后通过减压硅胶柱色谱进行分离，依次采用石油醚-乙酸乙酯(50:1-1:1)和二氯甲烷-甲醇(50:1-1:1)进行梯度洗脱。基于薄层色谱(TLC)和高效液相色谱(HPLC)检测结果合并相似组分，最终得到4个馏分(Fr. A-Fr. D)。
馏分B (35 g)通过ODS反相硅胶柱色谱分离，采用乙醇-水梯度洗脱(20%-100%)，获得馏分Fr. B1-B4。Fr. B2 (2.02 g)经硅胶柱色谱分离(二氯甲烷:甲醇：100:1-5:1)，基于TLC 和HPLC检测结果合并相似组分；进一步通过制备型HPLC (47%甲醇，流速7 mL/min)和半制备型HPLC (27%乙腈，流速2.5 mL/min)纯化，最终分离得到化合物1 (5.5 mg, tR=23.2 min)。Fr. B3 (1.04 g)经硅胶柱色谱分离(二氯甲烷:甲醇：100:1-5:1)，基于TLC和HPLC检测结果合并相似组分；依次采用制备型HPLC (62.5%甲醇，流速7 mL/min)和半制备型HPLC (37%乙腈，流速2.5 mL/min)纯化，最终分离得到化合物2 (5.7 mg, tR=14.7 min)。
1.3 α-葡萄糖苷酶抑制活性
参考Zhang et al. (2014)的报道，待测化合物用PBS稀释至200、100、50、25、5 μmol/L这5个浓度。在96孔板内，分别加入各浓度化合物溶液25 μL、PBS 125 μL以及α-葡萄糖苷酶溶液(0.1 U/mL) 25 μL。37 ℃孵育10 min后，加入2.5 mmol/L的pNPG底物溶液。继续反应30 min，于405 nm测定吸光度值(A1)。为准确计算抑制率，设置如下对照(均设3个平行)，样品空白组(A2)：孔内加入样品、PBS (替代酶)、PBS，反应后测定；对照组(A3)：孔内加入PBS (替代样品)、PBS、酶，反应后测定；对照空白组(A4)：孔内加入PBS (替代样品)、PBS (替代酶)、PBS，反应后测定。阿卡波糖作为阳性对照，按同样浓度梯度进行测试。α-葡萄糖苷酶抑制活性按公式(1)进行计算，最终通过剂量效应曲线拟合求得IC50值。
$\text { 抑制率 }(\%)=\left[\left(A_{3}-A_{4}\right)-\left(A_{1}-A_{2}\right)\right] /\left(A_{3}-A_{4}\right) \times 100 \%$
1.4 分子对接
从蛋白质数据库(PDB代码：2QMJ)中获取蛋白质晶体结构后，采用薛定谔Maestro软件进行分子对接研究。首先通过Maestro平台的蛋白质预处理向导(protein preparation wizard)对受体结构进行制备与优化，随后使用Glide模块的受体网格生成工具(receptor grid generation)基于优化后的受体模型生成网格。以各受体结构中原始原位配体为参照定义网格尺寸与空间位置，并在网格生成过程中排除配体自身的影响。
目标配体通过ChemDraw绘制二维结构，并经由LigPrep应用程序进行对接前预处理。所有配体互变异构体均通过Glide的配体对接工具(ligand docking)与刚性受体模型进行对接。对接结果根据DockScore进行排序，最终通过二维相互作用图示呈现对接构象，重点展示配体与受体氨基酸残基间的特异性相互作用(Shimmin et al. 2024)。所有分子对接结果最终通过PyMOL软件进行可视化呈现(Delano 2002；Xu et al. 2022)。
2 结果与分析
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基于现代波谱学技术，对从亚窄孢灵芝提取物中分离获得的2个化合物进行了结构鉴定(图1)，分别是17-hydroxy-12-ethoxycarbonyl-α- cadinol (1)和12-hydroxy-α-cadinol (2)，其中杜松烷型倍半萜化合物1为新化合物，化合物2首次在灵芝属物种中发现。
2.1 化合物的结构鉴定
化合物1：HR-ESI-MS显示准分子离子峰为m/z 319.187 9 [M+Na]+ (计算C17H28O4Na，319.188 0)，确定化合物1分子式为C17H28O4 (不饱和度4)。1H-NMR、13C-NMR (表1)及HSQC光谱显示17个碳信号：一个酯羰基[δC 171.37 (C-13)]，2个烯烃信号[δC 138.95 (C-4), δC/H 122.89 (C-5) / 5.72 (1H, s)]，2个连氧亚甲基[δC/H 68.42/3.96 (2H, d, J = 7.32 Hz), 67.39/4.03 (2H, m)]，3个甲基信号[δC/H 20.84/2.06 (3H, s), 10.54/0.84 (3H, d, J = 7.00 Hz), 21.20/1.12 (3H, s)]，4个亚甲基[δC/H 22.38/1.21 (1H, m), 1.26 (1H, m); 26.22/2.09 (1H, m, J = 6.36 Hz), 2.12 (1H, m, J = 4.68); 22.71/1.51 (1H, m, J = 3.59 Hz), 1.53 (1H, m, J = 3.59 Hz); 41.94/1.45 (1H, m), 1.32(1H, dt, J = 12.16, 3.40 Hz)]，5个次甲基[δC/H 50.17/1.28 (1H, m), 122.89/5.72(1H, s), 39.13/1.82 (1H, m), 42.01/1.80(1H, m), 31.30/2.35 (1H, qd, J = 7.13, 3.18)]，3个季碳(δC 138.95, 72.22, 171.37)。以上数据与化合物15-hydroxy-α-cadinol相似(朱云芳和王宜海 2024)，不同之处在于化合物1 的碳谱中存在2个额外的碳信号δC 171.4, 20.8，氢谱中多出一个甲基信号，推测结构中可能存在一个乙酰氧基片段。HMBC谱(图2)中，H-12和H-14与C-13有相关，证明乙酰氧基与C-12相连。
NOESY谱(图2)中，Me-16/H-6/Me-15/H-12/ H-8的相关性表明，H-6、Me-15、Me-16、H-12、H-8b均为β；H-5/H-11的相关性提示H-5和H-11的构型为α；此外，H-11的小耦合常数(J = 3.18 Hz)表明H-11和H-7为顺式构型，说明H-7的构型为α；C-1的相对构型由计算NMR证实(图3)，结果表明化合物1与1α的计算结果吻合度最高，R2值为0.996 4，DP4+ (all data)为100%，从而确定了C-1位的相对构型。化合物1的绝对构型通过计算ECD确定。通过对比计算所得与实验测得的ECD图谱(图4)，发现1S, 6R, 7R, 11S, 16S的计算ECD值与实验值高度一致，在200 nm处存在正Cotton效应，据此判定化合物1的绝对构型为1S, 6R, 7R, 11S, 16S。经Scifinder检索，化合物1为一种新化合物，命名为17- hydroxy-12-ethoxycarbonyl-α-cadinol。
化合物2：1H-NMR: 0.81 (3H, d, J = 6.97), 1.11 (3H, s), 1.20 (1H, dd, J = 12.45, 3.67 Hz), 1.25 (3H, m), 1.34 (2H, tt, J = 11.62, 3.34 Hz), 1.45 (1H, dd, J = 12.86, 4.20 Hz), 1.49 (1H, m), 1.67 (3H, s), 1.76 (1H, m), 1.78 (1H, m), 2.01 (3H, m), 2.19 (1H, qd, J = 7.09, 3.20 Hz), 3.53 (2H, m), 5.47 (1H, s). 13C-NMR: 135.5, 122.0, 72.4, 67.3, 50.2, 42.1, 41.9, 39.4, 34.7, 31.1, 24.0, 22.8, 22.6, 20.9, 10.4。以上数据与化合物12-hydroxy-α-cadinol (Zhao et al. 2013)一致。
2.2 α-葡萄糖苷酶抑制活性研究
对化合物1和2进行了α-葡萄糖苷酶的酶抑制活性测试(图5)，化合物1和2都表现出α-葡萄糖苷酶抑制活性，IC50值分别为(96.72±3.87)和(56.82±4.70) μmol/L；阳性对照为临床上用于控制血糖水平的阿卡波糖，其IC50为(39.88± 5.57) μmol/L。
为了深入了解活性化合物1和2与α-葡萄糖苷酶之间的相互作用，进行了分子对接研究。对接模型见图6，化合物1和2都能够通过氢键的相互作用进入MGAM (maltase-glucoamylase，麦芽糖酶-葡萄糖淀粉酶)腔。化合物1的C-13位羰基通过氢键与Ash-327相互作用，化合物2的C-12位羟基与Arg-526和Asp-542形成氢键。因此，推测氨基酸残基Ash-327、Arg-526和Asp-542可能在抑制α-葡萄糖苷酶的活性中发挥重要的作用。此外，化合物1具有与化合物2相似的结构，但表现出较低的抑制活性。这可能是侧链中C12位取代基不同，与MGAM形成的氢键强度不同，导致活性降低。
3 讨论
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本研究首次从亚窄孢灵芝中分离得到2个杜松烷型倍半萜类化合物，其中化合物1为新化合物，其结构的新颖性在于12位羟基发生了乙酰化。化合物2在灵芝属内首次发现。二者均表现出α-葡萄糖苷酶抑制活性，但化合物1活性强度[IC50=(96.72±3.87) μmol/L]弱于化合物2 [IC50=(56.82±4.70) μmol/L]和阳性对照阿卡波糖[IC50=(39.88±5.57) μmol/L]。这种活性差异可能源于结构特征：分子对接结果显示，MGAM的活性口袋与C12位氧取代基(乙酰氧基和羟基)形成氢键，表明该化合物骨架的C12位基团对活性影响很大，且羟基取代的活性效果强于乙酰氧基，推测C12位的羟基化可能是影响活性的关键修饰。此外，复杂杜松烷衍生物cornucadinoside A-E在低浓度下均具有显著的α-葡萄糖苷酶抑制活性，其中cornucadinoside E的抑制效果甚至比阳性对照阿卡波糖更有效，在结构上它们都具有糖苷基团(多羟基支链)，在与α-葡萄糖苷酶活性口袋的紧密结合上可能至关重要。α-葡萄糖苷酶的活性口袋是亲水的，其用于结合糖类底物(如麦芽糖、蔗糖) (Sim et al. 2010)。因此，阿卡波糖上的多个羟基(-OH)可以完美地模拟天然底物，与活性口袋中的氨基酸残基(如Ser、Arg、His、Tyr等)形成作用力较强的氢键网络，从而更紧密地结合，产生强效抑制(Jiang et al. 2020)。这也解释了山茱萸来源的糖苷化杜松烷cornucadinoside A-E具有高效的α-葡萄糖苷酶抑制活性，进一步说明羟基可能与α-葡萄糖苷酶相互作用至关重要(姜龙瑜等 2021)。
此外，在其他药用真菌中也发现了杜松烷型倍半萜，它们多数属于简单杜松烷型倍半萜。例如，从Ganoderma capense中发现的ganodermanol F (Tan et al. 2017)以及源自Montagnula donacina的donacinol B (Zhao et al. 2018)，它们均在杜松烷骨架上发生多位点羟基化，形成了不同的氧化模式，并展现出多样化的生物活性。其中，ganodermanol F 表现出对HCT116等癌细胞的细胞毒性。除上述大型真菌外，植物内生真菌如拟青霉属Paecilomyces、木霉属Trichoderma等也是杜松烷类成分的重要来源。例如，从烟草内生拟青霉TE-540中分离得到2个具有分子内醚键的新颖杜松烷型倍半萜paecilacadinol A和B (Xu et al. 2020)。从药用植物艾蒿内生绿木霉Trichoderma virens QA-8中分离的trichocadinins B-G等化合物(Shi et al. 2019)，在C-14位发生羧基取代，其中trichocadinins B和C含有苯并呋喃环且显示出较强的抗菌和抗真菌活性。在另一株海藻内生棘孢木霉Trichoderma asperelloides中亦分离得到杜松烷衍生物cadin-4-en-11-ol (Zou et al. 2021)，其结构在C-11位含羟基，且对海洋浮游植物Amphidinium carterae和Chattonella marina显示出强抑制活性。
灵芝属Ganoderma真菌化学成分的研究长期以来高度集中于三萜和多糖类化合物，这两类成分被认为是其免疫调节、抗肿瘤等核心药理活性的物质基础(Liu et al. 2022；Liu et al. 2024)。相比之下，该属真菌中的倍半萜类成分则研究较少，其化学多样性与生物学功能均未得到充分探索。本研究从亚窄孢灵芝中成功分离并鉴定2个杜松烷型倍半萜类化合物，揭示了其α-葡萄糖苷酶抑制活性，为亚窄孢灵芝在治疗糖尿病方面的潜在应用提供了科学依据。
作者贡献
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马世元：实验操作、数据处理与分析、图片绘制、论文构思与撰写；王雨曦：研究思路、实验设计、论文修改与审核；魏玉莲：论文修改与审核；袁海生：提供实验材料和菌种、项目管理与监督。
利益冲突声明
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该研究不存在任何潜在利益冲突的商业或财务关系。
基金
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  • 国家自然科学基金(32100013)
  • 辽宁省联合基金项目博士科研启动项目(2023-BSBA-328)
  • 中国科学院沈阳应用生态研究所森林生态与保育重点实验室项目(KLFES-2028)
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doi: 10.13346/j.mycosystema.250283
  • 接收时间：2025-10-07
  • 首发时间：2026-04-30
  • 出版时间：2026-01-22
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  • 收稿日期：2025-10-07
  • 录用日期：2025-11-04
基金
National Natural Science Foundation of China(32100013)
国家自然科学基金(32100013)
Liaoning Provincial Joint Fund Program - Doctoral Research Initiation Project(2023-BSBA-328)
辽宁省联合基金项目博士科研启动项目(2023-BSBA-328)
Fund of CAS Key Laboratory of Forest Ecology and Silviculture, Institute of Applied Ecology, Chinese Academy of Sciences(KLFES-2028)
中国科学院沈阳应用生态研究所森林生态与保育重点实验室项目(KLFES-2028)
作者信息
    1 中国科学院沈阳应用生态研究所 中国科学院森林生态与保育重点实验室，辽宁 沈阳 110164
    2 辽宁大学生命科学院，辽宁 沈阳 110036

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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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