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Article(id=1308467730751967802, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308467640138227885, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2025-0323, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1742745600000, receivedDateStr=2025-03-24, revisedDate=1753113600000, revisedDateStr=2025-07-22, acceptedDate=null, acceptedDateStr=null, onlineDate=1789892617166, onlineDateStr=2026-09-20, pubDate=1760198400000, pubDateStr=2025-10-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789892617166, onlineIssueDateStr=2026-09-20, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789892617166, creator=13701087609, updateTime=1789892617166, updator=13701087609, issue=Issue{id=1308467640138227885, tenantId=1146029695717560320, journalId=1189982191388893191, year='2025', volume='60', issue='10', pageStart='2913', pageEnd='3262', issueExtLink='null', onlineDate='null', pubDate='1760198400000', pubDateStr='2025-10-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789892595562, creator='13701087609', updateTime=1789893273356, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308470483071033443, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308467640138227885, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308470483071033444, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308467640138227885, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=3131, endPage=3138, ext={EN=ArticleExt(id=1308467732391940667, articleId=1308467730751967802, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Study on the alkaloids of Corydalis delicatula D. G. Long and their urease inhibitory activity, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Fifteen compounds were successfully isolated from the total alkaloid content of Corydalis delicatula D. G. Long using a variety of chromatographic techniques, including silica gel, basic alumina, MCI, Sephadex LH-20 column chromatography, and HPLC. The structures of the isolated compounds were identified as (-)-tetrahydrocorysamine (1), corysamine (2), berberrubine (3), (-)-scoulerine (4), bicuculline (5), (-)-corlumine (6), scoulerine-β-N-oxide (7), salutaridine N-oxide (8), allocryptopine (9), protopine (10), coryximine (11), cryptopine (12), cis-N-methylstylopine (13), hunnemannine (14), and corlicatine A (15) through spectroscopic methods such as MS, NMR, and UV. These compounds were isolated for the first time from C. delicatula, and corlicatine A (15) is a new compound. Pharmacological testing revealed that compound 1 demonstrated excellent inhibition against Jack bean urease (JBU), with an IC50 value of 1.28 µmol‧L-1, surpassing the effectiveness of the positive control AHA. The synergistic inhibitory influence on JBU activity by compounds 1, 6, 11, 12 and inorganic reagents NaF and BA were proved by addition of competitive inhibitors NaF or BA. The molecular docking experiment between the most active alkaloid (-)-tetrahydrocorysamine (1) and the urease protein of the JBU was not found to interact with Ni2+, which is recognized as the active site of urease. Consequently, considering the impact of inorganic reagents on the inhibitory properties of alkaloids against JBU, it is hypothesized that the inhibitory effect of isoquinoline alkaloids on urease may involve targets or mechanisms other than Ni2+.

, authors=Jia CUI, Shao-wen XIONG, Yu-chen JIANG, Xin-yue HUANG, Li-mei LI*, authorsList=Jia CUI, Shao-wen XIONG, Yu-chen JIANG, Xin-yue HUANG, Li-mei LI, authorCompany=null, correspAuthors=Li-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, fund=null), CN=ArticleExt(id=1308467733906084420, articleId=1308467730751967802, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=娇嫩黄堇生物碱成分及脲酶抑制活性研究, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶、碱性氧化铝、MCI、葡聚糖凝胶Sephadex LH-20柱色谱和高效液相色谱等多种色谱技术, 从娇嫩黄堇(Corydalis delicatula D. G. Long) 总生物碱中分离得到15个生物碱化合物。通过质谱、核磁共振波谱、紫外可见光谱等方法分别鉴定为(-)-tetrahydrocorysamine (1)、corysamine (2)、berberrubine (3)、(-)-scoulerine (4)、bicuculline (5)、(-)-corlumine (6)、scoulerine-β-N-oxide (7)、salutaridine N-oxide (8)、allocryptopine (9)、protopine (10)、coryximine (11)、cryptopine (12)、cis-N-methylstylopine (13)、hunnemannine (14) 和corlicatine A (15)。所有化合物均首次从娇嫩黄堇中分离得到, 其中corlicatine A (15) 为新化合物。药理活性研究表明, 1对洋刀豆脲酶(JBU) 的抑制活性最强, IC50值为1.28 µmol‧L-1, 优于阳性对照物乙酰氧肟酸(AHA)。通过无机试剂对生物碱抑制JBU的影响实验, 发现四个生物碱(1、6、11、12) 与无机试剂氟化钠(NaF) 及丙烯酸丁酯(BA) 之间存在协同抑制作用。将活性最好的生物碱(1) 与JBU蛋白进行分子对接实验, 未发现与JBU公认的活性中心位点Ni2+发生作用。结合无机试剂对生物碱抑制JBU活性的影响, 推测异喹啉类生物碱对脲酶的抑制作用可能涉及Ni2+以外的其他靶点或机制。

, authors=崔佳, 熊邵文, 姜雨辰, 黄昕玥, 李丽梅*, authorsList=崔佳, 熊邵文, 姜雨辰, 黄昕玥, 李丽梅, authorCompany=null, correspAuthors=李丽梅, authorNote=

作者贡献:

崔佳负责完成论文的撰写与修改; 熊邵文、姜雨辰、黄昕玥负责完成所有实验研究; 李丽梅对本文选题与设计、实验思路及文章修改提供了支持。

, correspAuthorsNote=
李丽梅, E-mail:
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No.δHδC
17.56 (s, 1H)110.1
2146.4
3150.3
47.14 (s, 1H)108.2
4a135.2
53.07 (m, 2H)26.6
64.67 (m, 2H)55.3
89.20 (s, 1H)144.9
8a133.7
10a149.7
11130.2
12147.5
12a119.4
2-OCH2O-36.18 (s, 2H)102.3
-CH32.51 (s, 3H)18.3
-COOH160.9
-COOCH33.86 (s, 3H)52.5
-COOCH3167.0
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1H NMR (600 MHz) and 13C NMR (150 MHz) data of compound 15 in DMSO-d6

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No.δHδC
17.56 (s, 1H)110.1
2146.4
3150.3
47.14 (s, 1H)108.2
4a135.2
53.07 (m, 2H)26.6
64.67 (m, 2H)55.3
89.20 (s, 1H)144.9
8a133.7
10a149.7
11130.2
12147.5
12a119.4
2-OCH2O-36.18 (s, 2H)102.3
-CH32.51 (s, 3H)18.3
-COOH160.9
-COOCH33.86 (s, 3H)52.5
-COOCH3167.0
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CompoundIC50 / µmol‧L-1
11.28 ± 0.02
245.67 ± 0.13
415.04 ± 0.32
524.23 ± 0.32
661.95 ± 0.29
722.92 ± 0.03
970.44 ± 0.38
1094.83 ± 0.28
1139.28 ± 0.23
128.21 ± 0.13
1332.29 ± 0.48
AHA41.96 ± 0.02
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Inhibitory activity of major compounds from C. delicatula on Jack bean urease (JBU). AHA: Acetohydroxamic acid

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CompoundIC50 / µmol‧L-1
11.28 ± 0.02
245.67 ± 0.13
415.04 ± 0.32
524.23 ± 0.32
661.95 ± 0.29
722.92 ± 0.03
970.44 ± 0.38
1094.83 ± 0.28
1139.28 ± 0.23
128.21 ± 0.13
1332.29 ± 0.48
AHA41.96 ± 0.02
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娇嫩黄堇生物碱成分及脲酶抑制活性研究
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崔佳 , 熊邵文 , 姜雨辰 , 黄昕玥 , 李丽梅 *
药学学报 | 研究论文 2025,60(10): 3131-3138
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药学学报 |研究论文 2025 , 60 (10) : 3131 -3138
娇嫩黄堇生物碱成分及脲酶抑制活性研究
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崔佳, 熊邵文, 姜雨辰, 黄昕玥, 李丽梅*
作者信息
  • 西南民族大学药学与食品学院, 四川 成都 610041
通讯作者:
李丽梅, E-mail:
作者简介:

作者贡献:

崔佳负责完成论文的撰写与修改; 熊邵文、姜雨辰、黄昕玥负责完成所有实验研究; 李丽梅对本文选题与设计、实验思路及文章修改提供了支持。

Study on the alkaloids of Corydalis delicatula D. G. Long and their urease inhibitory activity
Jia CUI, Shao-wen XIONG, Yu-chen JIANG, Xin-yue HUANG, Li-mei LI*
Affiliations
  • College of Pharmacy and Food, Southwest Minzu University, Chengdu 610041, China
出版时间: 2025-10-12 doi: 10.16438/j.0513-4870.2025-0323
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摘要
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采用硅胶、碱性氧化铝、MCI、葡聚糖凝胶Sephadex LH-20柱色谱和高效液相色谱等多种色谱技术, 从娇嫩黄堇(Corydalis delicatula D. G. Long) 总生物碱中分离得到15个生物碱化合物。通过质谱、核磁共振波谱、紫外可见光谱等方法分别鉴定为(-)-tetrahydrocorysamine (1)、corysamine (2)、berberrubine (3)、(-)-scoulerine (4)、bicuculline (5)、(-)-corlumine (6)、scoulerine-β-N-oxide (7)、salutaridine N-oxide (8)、allocryptopine (9)、protopine (10)、coryximine (11)、cryptopine (12)、cis-N-methylstylopine (13)、hunnemannine (14) 和corlicatine A (15)。所有化合物均首次从娇嫩黄堇中分离得到, 其中corlicatine A (15) 为新化合物。药理活性研究表明, 1对洋刀豆脲酶(JBU) 的抑制活性最强, IC50值为1.28 µmol‧L-1, 优于阳性对照物乙酰氧肟酸(AHA)。通过无机试剂对生物碱抑制JBU的影响实验, 发现四个生物碱(1、6、11、12) 与无机试剂氟化钠(NaF) 及丙烯酸丁酯(BA) 之间存在协同抑制作用。将活性最好的生物碱(1) 与JBU蛋白进行分子对接实验, 未发现与JBU公认的活性中心位点Ni2+发生作用。结合无机试剂对生物碱抑制JBU活性的影响, 推测异喹啉类生物碱对脲酶的抑制作用可能涉及Ni2+以外的其他靶点或机制。

娇嫩黄堇  /  生物碱  /  corlicatine A  /  脲酶抑制剂  /  分子对接

Fifteen compounds were successfully isolated from the total alkaloid content of Corydalis delicatula D. G. Long using a variety of chromatographic techniques, including silica gel, basic alumina, MCI, Sephadex LH-20 column chromatography, and HPLC. The structures of the isolated compounds were identified as (-)-tetrahydrocorysamine (1), corysamine (2), berberrubine (3), (-)-scoulerine (4), bicuculline (5), (-)-corlumine (6), scoulerine-β-N-oxide (7), salutaridine N-oxide (8), allocryptopine (9), protopine (10), coryximine (11), cryptopine (12), cis-N-methylstylopine (13), hunnemannine (14), and corlicatine A (15) through spectroscopic methods such as MS, NMR, and UV. These compounds were isolated for the first time from C. delicatula, and corlicatine A (15) is a new compound. Pharmacological testing revealed that compound 1 demonstrated excellent inhibition against Jack bean urease (JBU), with an IC50 value of 1.28 µmol‧L-1, surpassing the effectiveness of the positive control AHA. The synergistic inhibitory influence on JBU activity by compounds 1, 6, 11, 12 and inorganic reagents NaF and BA were proved by addition of competitive inhibitors NaF or BA. The molecular docking experiment between the most active alkaloid (-)-tetrahydrocorysamine (1) and the urease protein of the JBU was not found to interact with Ni2+, which is recognized as the active site of urease. Consequently, considering the impact of inorganic reagents on the inhibitory properties of alkaloids against JBU, it is hypothesized that the inhibitory effect of isoquinoline alkaloids on urease may involve targets or mechanisms other than Ni2+.

Corydalis delicatula D. G. Long  /  alkaloid  /  corlicatine A  /  urease inhibitor  /  molecular docking
崔佳, 熊邵文, 姜雨辰, 黄昕玥, 李丽梅. 娇嫩黄堇生物碱成分及脲酶抑制活性研究. 药学学报, 2025 , 60 (10) : 3131 -3138 . DOI: 10.16438/j.0513-4870.2025-0323
Jia CUI, Shao-wen XIONG, Yu-chen JIANG, Xin-yue HUANG, Li-mei LI. Study on the alkaloids of Corydalis delicatula D. G. Long and their urease inhibitory activity[J]. Acta Pharmaceutica Sinica, 2025 , 60 (10) : 3131 -3138 . DOI: 10.16438/j.0513-4870.2025-0323
正文
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脲酶(urease) 作为一些植物、细菌和真菌中发现的镍依赖性金属酶, 被证实是多物种的有效毒力因子[1], 在幽门螺杆菌代谢中, 其毒力是胃黏膜定植所必须的, 并且是引发强烈免疫应答的有效免疫原[2], 而乙酰氧肟酸(AHA) 作为临床实践中被美国食品和药物管理局批准的标准药物, 其不良反应严重影响了临床使用[3]。研究和开发不良反应小、效果更好的脲酶抑制剂在药物化学中一直是活跃领域。
本课题组对多种植物提取物进行了抑制脲酶活性筛选, 发现罂粟科(Papaveraceae) 紫堇属(Corydalis) 植物娇嫩黄堇(Corydalis delicatula D. G. Long) 的总生物碱对洋刀豆脲酶(JBU)具有明显的抑制活性, 其IC50为0.19 µg‧mL-1。娇嫩黄堇是多年生草本, 高26~45 cm。须根多数, 细长。茎直立, 具少数分枝。产自西藏中南部(朗县), 生于海拔274~3 200 m的林下, 不丹有分布[4]。国内外未见对该植物的化学成分及相关活性的研究报道。因此, 研究娇嫩黄堇的总生物碱的化学成分及其脲酶抑制活性, 对脲酶抑制剂的开发及相关医药领域的研究具有一定意义。本研究从娇嫩黄堇总生物碱中共分离得到15个化合物(图1), 其中corlicatine A (15) 为新化合物。将含量较多的11个化合物进行标准酶活性实验, 并测试了无机试剂氟化钠(NaF) 及丙烯酸丁酯(BA) 对化合物1、6、11和12抑制JBU活性的影响, 最后以分子对接的形式探究化合物1对JBU蛋白的抑制机制, 为研发新型的脲酶抑制剂提供一定的理论基础。
结果与讨论
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1　新化合物结构鉴定
化合物15  黄色粉末, HR-ESI-MS给出准分子离子峰m/z 342.091 8 [M]+ (计算值为342.097 3), 推测分子式为C18H16NO6+, 不饱和度为12。1H NMR谱(600 MHz, DMSO-d6) 数据显示(表1) 存在3个芳香氢信号[δH 9.20 (s, 1H, H-8), 7.56 (s, 1H, H-1), 7.14 (s, 1H, H-4)]、2个亚甲基信号[δH 4.67 (m, 2H, H-6), 3.07 (m, 2H, H-5)]、1个亚甲二氧基信号δH 6.18 (s, 2H, 2-OCH2O-3)、1个甲氧基信号δH 3.86 (s, 3H) 和1个甲基信号δH 2.51 (s, 3H)。13C NMR谱(150 MHz, DMSO-d6) 数据显示(表1) 共18个碳原子, 包括11个芳环碳[δC 150.3 (C-3), 149.7 (C-10a), 147.5 (C-12), 146.4 (C-2), 144.9 (C-8), 135.2 (C-4a), 133.7 (C-8a), 130.2 (C-11), 119.4 (C-12a), 110.1 (C-1), 108.2 (C-4)]、2个亚甲基碳[δC 55.3 (C-6), 26.6 (C-5)]、1个亚甲二氧基碳[δC 102.3 (2-OCH2O-3)]、1个甲氧基碳(δC 52.5)、1个甲基碳(δC 18.3) 以及与芳环共轭的1个羧基(δC 160.9) 和1个酯羰基(δC 167.0)。以上数据提示化合物15可能为小檗碱类生物碱的衍生物[5]。在HMBC谱中(图2), H-8与C-6 (δC 55.3)、C-12 (δC 147.5)、C-10a (δC 149.7)、C-8a (δC 133.7) 相关, H-5与C-4 (δC 108.2)、C-4a (δC 135.2)、C-6 (δC 55.3)、C-12a (δC 119.4) 相关, 证明存在异喹啉结构片段；亚甲二氧基的氢信号(δH 6.18) 与C-2 (δC 146.4)、C-3 (δC 150.3) 相关, 表明亚甲二氧基连在C-2, 3位; 甲基信号(δH 2.51) 与C-11 (δC 130.2) 相关, 表明甲基连在C-11; 甲氧基信号(δH 3.86) 与C-9 (δC 167.0) 相关, 表明其与C-9的酸形成甲酯, 使羧酸中碳的化学位移向低场变化; H-8与C-9 (δC 167.0) 相关, 进一步证明羧酸甲酯连在C-8a。至此, 再结合HR-ESI-MS, 可以推测羧基位于C-10。综上所述, 确定化合物15的结构, 命名为corlicatine A。
2　对JBU的抑制活性
2.1　对JBU抑制活性的筛选
娇嫩黄堇中分离得到含量较多的11个化合物1、2、4~7、9~13对JBU的抑制活性见表2。由表2可知, 11个化合物均表现出不同程度的抑制活性, 化合物1、4、5、7、11、12和13对JBU的抑制活性均强于阳性对照AHA。其中(-)-tetrahydroeorysamine (1) 对JBU的抑制活性最强, IC50值明显小于阳性对照物AHA, 为1.28 ± 0.02 µmol‧L-1。
2.2　无机试剂对生物碱抑制JBU作用的测试
在无机试剂对生物碱抑制JBU影响的测试中, 将上述11个生物碱化合物分类后, 选取每种类型中含量较多、活性较好的4个化合物1、12、11和6, 测试其在竞争性抑制剂无机试剂的影响下, 对JBU抑制活性的作用。结果如图3, 4个生物碱与NaF及BA对JBU的抑制作用程度均不相同, 但在BA或NaF存在下4个生物碱灭活的JBU残留活性均低于单独使用无机试剂时的残留酶活性, 表明4个生物碱与无机试剂NaF及BA之间可能对JBU具有协同抑制作用。
3　娇嫩黄堇生物碱单体与JBU活性部位分子对接研究
选取抑制活性最强的化合物1与底物JBU蛋白进行分子对接研究。在对接实验中, 选取JBU活性中心的两个镍离子的平均坐标为中心, 逐步缩小对接盒子的体积, 最终确定化合物1与JBU的最佳结合构象, 其结构能为-6.6 kcal‧mol-1。从图4中看出化合物1的游离甲基与残基HIS593通过Pi-Sigma键稳定结合, 两个苯环分别与ASP494及ALA436残基通过Pi-Anion及Pi-Alkyl键相互作用, 其中一个环氧亚甲基的O与残基HIS594形成C-H作用键, 整个生物碱基团与LEU523、CME592及ARG439残基通过范德华力固定于活性空腔中。从对接图中并未看出生物碱分子与JBU公认活性中心Ni2+发生明显的相互作用。
4　讨论
本研究首次发现娇嫩黄堇总生物碱对JBU有明显的抑制活性, 随后从总生物碱中分离得到15个化合物, 其中化合物15为新化合物, 揭示了娇嫩黄堇化学成分的多样性。并且将分离得到含量较多的11个化合物进行JBU抑制活性研究, 结果表明11个化合物对JBU均表现出不同程度的抑制作用, 其中化合物1的抑制活性最强, 且强于阳性对照AHA。其中4个生物碱(1、6、11、12) 与无机试剂NaF及BA之间可能存在对JBU活性的协同抑制作用。通过分子对接初步探究化合物1对JBU的抑制机制, 结果表明化合物1的不同特征基团均对不同的氨基酸残基产生作用, 从而将生物碱固定于JBU活性空腔中, 但并未对公认的JBU活性中心Ni2+有明显的作用, 结合无机试剂实验推测异喹啉类生物碱对JBU的抑制作用可能涉及Ni2+以外的其他靶点或机制。因此, 后续将进一步研究娇嫩黄堇中生物碱化合物对JBU抑制作用的机制和靶点, 为开发效果更好、不良反应更小的脲酶抑制剂提供新的思路和方向。
实验部分
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400、600 MHz核磁共振波谱仪(德国Bruker公司), SPD-16高效液相色谱仪(岛津仪器有限公司), LC-100伍丰液相色谱仪(上海伍丰科学仪器有限公司), 质谱(Waters Vion IMS QTof), CYT5M多功能全波长酶标仪(美国伯腾仪器有限公司), TU-1901双光束紫外可见分光光度计(北京普析通用仪器有限公司)。
碘化铋钾(国药集团化学试剂有限公司), 氘代试剂(99.8%, 美国剑桥同位素实验有限公司), 乙酰氧肟酸(西亚试剂有限公司), PBS缓冲溶液(pH 7.2~7.4) (上海通蔚生物有限公司), 二甲基亚砜(DMSO, 天津金瑞特试剂有限公司), JBU、尿素(源叶生物有限公司), 甲醇、氯仿、石油醚、乙酸乙酯等试剂均为分析纯, 由成都力信和化工有限责任公司提供。
娇嫩黄堇全草2019年7月采自云南腾冲, 由西南民族大学药学与食品学院吕露阳副教授鉴定为娇嫩黄堇(Corydalis delicatula D. G. Long), 标本(No. LMCD1907) 存放于西南民族大学药学与食品学院。
1　提取与分离
称取干燥的娇嫩黄堇10 kg, 粉碎后用甲醇浸泡提取3次, 浸泡时间依次为48、24、24 h, 提取液减压浓缩得到浸膏。将浸膏分散于2%的HCl溶液中, 所得酸提取液合并后用氯仿等体积萃取3次, 酸水层用氨水碱化(pH 9~10) 后抽滤, 除去固体杂质, 滤液继续用氯仿萃取3次, 将氯仿层减压浓缩回收溶剂, 得到总生物碱(155.8 g)。总生物碱(155.5 g) 经200~300目硅胶柱色谱分离, 以氯仿-甲醇(1∶0→0∶1)进行梯度洗脱。回收溶剂TLC检测后并以碘化铋钾试液进行显色, 合并相同组分, 共得到11个组分(Fr.A~K)。
Fr.A (25.9 g) 经200~300目硅胶柱色谱分离, 以石油醚-氯仿(50∶1→1∶1) 进行梯度洗脱, 得到化合物1 (13.0 mg)。Fr.A和Fr.B (6.9 g) 中析出大量黄色针状晶体, 即为化合物2 (1.5 g)。
Fr.C (9.5 g) 经200~300目碱性氧化铝柱色谱分离, 以氯仿-甲醇(1∶0→0∶1) 进行梯度洗脱得到Fr.C1~C10。Fr.C10经MCI柱, 以甲醇-水(0∶1→1∶0) 进行梯度洗脱, 得到化合物3 (17.0 mg)。
Fr.D (6.4 g) 经200~300目碱性氧化铝柱色谱分离, 以氯仿-甲醇(1∶0→0∶1) 进行梯度洗脱得到Fr.D1~Fr.D4。Fr.D1经制备HPLC纯化(甲醇-水= 9∶20, 0.1%三乙胺, 30 mL‧min-1), 得到化合物4 (tR = 19.1 min, 25.0 mg)。Fr.D2经制备HPLC纯化(甲醇-水= 11∶20, 0.1%三乙胺, 30 mL‧min-1), 得到化合物5 (tR = 16.3 min, 35.0 mg); Fr.D3经制备HPLC纯化(甲醇-水= 33∶50, 0.1%三乙胺, 30 mL‧min-1), 得到化合物6 (tR = 22.3 min, 68.0 mg); Fr.D4经制备HPLC纯化(甲醇-水= 7∶10, 0.1%三乙胺, 30 mL‧min-1), 得到化合物7 (tR = 25.1 min, 15.0 mg)、化合物8 (tR = 36.3 min, 23.0 mg)。
Fr.G (7.6 g) 经大孔吸附树脂, 甲醇-水(0∶1→1∶0) 梯度洗脱后得到Fr.G1~G6。Fr.G2再经200~300目碱性氧化铝柱色谱分离, 以氯仿-甲醇(20∶1→15∶1) 进行梯度洗脱, 得到化合物15 (2.5 mg)。
Fr.H (40.2 g) 经200~300目碱性氧化铝柱色谱分离, 以氯仿-甲醇(1∶0→0∶1) 进行梯度洗脱得到Fr.H1~H4, 其中Fr.H3析出化合物11 (135.0 mg)。Fr.H1经制备HPLC纯化(甲醇-水= 77∶100, 0.1%三乙胺, 10 mL‧min-1), 得到化合物9 (tR = 30.0 min, 230.0 mg); Fr.H2经制备HPLC纯化(甲醇-水= 3∶5, 0.1%三乙胺, 10 mL‧min-1), 得到化合物10 (tR = 35.2 min, 170.0 mg); Fr.H4经制备HPLC纯化(甲醇-水= 9∶20, 0.1%三乙胺, 10 mL‧min-1), 得到化合物12 (tR = 55.2 min, 250.0 mg)。
Fr.J (4.8 g) 经MCI柱, 以甲醇-水(0∶1→1∶0) 进行梯度洗脱得Fr.J1~J3, 其中Fr.J2中析出白色粉末, 即化合物13 (500.0 mg)。Fr.J3用ODS柱色谱分离, 以甲醇-水(0∶1→1∶0) 进行梯度洗脱后, 继续进行硅胶柱色谱分离, 以乙酸乙酯-甲醇(50∶0→5∶1) 进行梯度洗脱, 得到化合物14 (4.0 mg)。
2　结构鉴定
化合物1  无色柱晶; 1H NMR (400 MHz, CDCl3) δH: 0.95 (3H, d, J = 8.0 Hz, 13-CH3), 2.58 (2H, m, H-5), 3.08 (1H, m, H-6a), 3.15 (1H, m, H-13), 3.23 (1H, m, H-6b), 3.48 (1H, d, J = 15.3 Hz, H-8a), 3.70 (1H, brs, H-14), 4.06 (1H, d, J = 15.3 Hz, H-8b), 5.93, 5.91 (each 1H, s, 2-OCH2O-3), 5.96, 5.95 (each 1H, s, 9-OCH2O-10), 6.60 (1H, s, H-1), 6.68 (3H, m, H-4, 11, 12); 13C NMR (100 MHz, CDCl3) δC: 18.5 (13-CH3), 29.9 (C-5), 38.8 (C-13), 51.3 (C-6), 53.4 (C-8), 63.6 (C-14), 100.9 (2-OCH2O-3), 101.2 (9-OCH2O-10), 105.7 (C-1), 106.9 (C-11), 108.4 (C-4), 116.9 (C-8a), 121.4 (C-12), 129.4 (C-14a), 129.7 (C-4a), 136.0 (C-12a), 143.2 (C-2), 144.8 (C-3), 145.8 (C-10), 146.5 (C-9)。1H NMR与13C NMR数据与文献[6]对照一致, 因此鉴定化合物1为(-)-tetrahydrocorysamine。
化合物2  黄色针晶; 1H NMR (400 MHz, CD3OD) δH: 2.99 (3H, s, 13-CH3), 3.16 (2H, m, H-5), 4.77 (2H, m, H-6), 6.12 (2H, s, 2-OCH2O-3), 6.49 (2H, s, 9-OCH2O-10), 7.04 (1H, s, H-4), 7.34 (1H, s, H-1), 7.91 (1H, d, J = 8.0 Hz, H-12), 8.01 (1H, d, J = 8.0 Hz, H-11), 9.73 (1H, s, H-8); 13C NMR (100 MHz, CD3OD) δC: 18.7 (13-CH3), 29.1 (C-5), 58.6 (C-6), 103.6 (2-OCH2O-3), 106.3 (9-OCH2O-10), 109.2 (C-1), 111.8 (C-4), 112.9 (C-11), 120.6 (C-12), 121.4 (C-14a), 121.9 (C-4a), 132.8 (C-13), 134.5 (C-12a), 134.8 (C-8a), 137.5 (C-14), 143.8 (C-8), 146.7 (C-10), 148.6 (C-9), 149.2 (C-2), 151.3 (C-3)。1H NMR与13C NMR数据与文献[5]对照一致, 因此鉴定化合物2为corysamine。
化合物3  砖红色粉末; 1H NMR (400 MHz, DMSO-d6) δH: 3.19 (2H, m, H-5), 3.87 (3H, s, -OCH3), 4.87 (2H, m, H-6), 6.52 (2H, s, 2-OCH2O-3), 7.05 (1H, s, H-4), 7.54 (1H, s, H-1), 7.88 (1H, d, J = 8.7 Hz, H-11), 8.02 (1H, d, J = 8.7 Hz, H-12), 8.84 (1H, s, H-13), 9.92 (1H, s, H-8); 13C NMR (100 MHz, DMSO-d6) δC: 25.9 (C-5), 55.5 (C-6), 55.9 (-OCH3), 104.4 (2-OCH2O-3), 111.4 (C-4), 111.7 (C-1), 112.1 (C-11), 119.2 (C-8a), 120.5 (C-14a), 120.9 (C-13), 121.8 (C-12), 127.0 (C-4a), 132.5 (C-12a), 137.2 (C-14), 143.7 (C-9), 144.5 (C-8), 146.4 (C-2), 146.9 (C-3), 150.6 (C-10)。1H NMR与 13C NMR数据与文献[7]对照一致, 因此鉴定化合物3为berberrubine。
化合物4  无色方晶; 1H NMR (400 MHz, CDCl3) δH: 2.64 (2H, m, H-5), 2.83 (1H, m, H-13a), 3.14 (1H, m, H-6a) 3.22 (2H, m, H-6b, 13b), 3.50 (1H, d, J = 15.6 Hz, H-8a), 3.54 (1H, m, H-14), 3.87 (6H, s, 3, 10-OCH3), 4.24 (1H, d, J = 15.6 Hz, H-8b), 6.59 (1H, s, H-4), 6.66 (1H, d, J = 8.1 Hz, H-12), 6.73 (1H, d, J = 8.1 Hz, H-11), 6.82 (1H, s, H-1); 13C NMR (100 MHz, CDCl3) δC: 29.8 (C-5), 36.3 (C-13), 51.7 (C-6), 53.6 (C-8), 56.1 (10-OCH3), 56.3 (3-OCH3), 59.3 (C-14), 109.2 (C-1), 110.7 (C-11), 111.5 (C-4), 119.4 (C-12), 121.7 (C-8a), 126.3 (C-14a), 128.3 (C-12a), 130.6 (C-4a), 141.7 (C-9), 144.1 (C-10), 144.2 (C-3), 145.2 (C-2)。1H NMR与 13C NMR数据与文献[8]对照一致, 因此鉴定化合物4为(-)-scoulerine。
化合物5  淡黄色粉末; 1H NMR (400 MHz, CDCl3) δH: 2.23 (1H, m, H-4a), 2.55 (5H, m, H-3a, 4b, N-CH3), 2.84 (1H, m, H-3b), 4.04 (1H, d, J = 4.0 Hz, H-1), 5.56 (1H, d, J = 4.0 Hz, H-9), 5.94 (2H, s, 4′-OCH2O-5′), 6.17 (3H, m, H-2′, 6-OCH2O-7), 6.48 (1H, s, H-8), 6.58 (1H, s, H-5), 6.91 (1H, d, J = 8.0 Hz, H-3′); 13C NMR (100 MHz, CDCl3) δC: 29.9 (C-4), 45.2 (N-CH3), 49.4 (C-3), 66.1 (C-1), 85.0 (C-9), 101.0 (6-OCH2O-7), 103.3 (4′-OCH2O-5′), 107.8 (C-8), 108.6 (C-5), 110.3 (C-3′), 113.2 (C-6′), 115.6 (C-2′), 124.5 (C-4a), 130.6 (C-8a), 140.4 (C-1′), 144.6 (C-5′), 146.0 (C-7), 146.9 (C-6), 149.2 (C-4′), 167.4 (C-10)。1H NMR与13C NMR数据与文献[9]对照一致, 因此鉴定化合物5为bicuculline。
化合物6  白色针晶; 1H NMR (400 MHz, CD3OD) δH: 2.44 (1H, m, H-4a), 2.58 (3H, s, N-CH3), 2.63 (1H, m, H-4b), 2.70 (1H, m, H-3a), 3.01 (1H, m, H-3b), 3.50 (3H, s, 6-OCH3), 3.78 (3H, s, 7-OCH3), 4.15 (1H, m, H-1), 5.84 (1H, m, H-9), 6.12 (2H, s, 4′-OCH2O-5′), 6.16 (1H, s, H-8), 6.55 (1H, d, J = 8.0 Hz, H-2′), 6.67 (1H, s, H-5), 7.09 (1H, d, J = 8.0 Hz, H-3′); 13C NMR (100 MHz, CD3OD) δC: 27.1 (C-4), 44.5 (N-CH3), 49.9 (C-3), 56.3 (6-OCH3), 66.9 (C-1), 85.4 (C-9), 104.8 (4′-OCH2O-5′), 110.7 (C-6′), 112.1 (C-8), 112.7 (C-5), 114.7 (C-3′), 116.8 (C-2′), 123.8 (C-4a), 130.5 (C-8a), 142.4 (C-1′), 146.0 (C-5′), 148.0 (C-7), 149.6 (C-6), 150.6 (C-4′), 166.9 (C-10)。1H NMR与13C NMR数据与文献[10]对照一致, 因此鉴定化合物6为(-)-corlumine。
化合物7  黄色粉末; 1H NMR (400 MHz, CD3OD) δH: 2.76 (1H, m, H-5a), 3.28 (2H, m, H-13), 3.37 (1H, m, H-6a), 3.57 (1H, m, H-5b), 3.72 (1H, m, H-6b), 3.77 (3H, s, 10-OCH3), 3.81 (3H, s, 3-OCH3), 4.57 (3H, m, H-8, 14), 6.74 (2H, s, H-1, 4), 6.75 (1H, d, J = 8.0 Hz, H-12), 6.84 (1H, d, J = 8.0 Hz, H-11); 13C NMR (100 MHz, CD3OD) δC: 25.9 (C-5), 30.5 (C-13), 56.3 (10-OCH3), 56.5 (3-OCH3), 65.3 (C-6), 67.6 (C-8), 68.8 (C-14), 111.8 (C-11), 112.4 (C-4), 113.5 (C-1), 117.3 (C-8a), 119.9 (C-12), 124.4 (C-4a), 125.7 (C-14a), 126.5 (C-12a), 144.4 (C-9), 146.7 (C-3), 146.9 (C-10), 148.6 (C-2)。1H NMR与13C NMR数据与文献[11]对照一致, 因此鉴定化合物7为scoulerine-β-N-oxide。
化合物8  黄色粉末; 1H NMR (400 MHz, CD3OD) δH: 2.38 (1H, m, H-15a), 2.44 (1H, m, H-16a), 3.22 (2H, m, H-15b, 16b), 3.30 (3H, overlapped, N-CH3), 3.49 (2H, m, H-10), 3.75 (3H, s, 6-OCH3), 3.86 (3H, s, 3-OCH3), 4.29 (1H, m, H-9), 6.45 (1H, s, H-8), 6.69 (1H, d, J = 8.3 Hz, H-1), 6.92 (1H, d, J = 8.3 Hz, H-2), 7.80 (1H, s, H-5); 13C NMR (150 MHz, CD3OD) δC: 34.3 (C-10), 36.4 (C-15), 43.6 (C-13), 55.4 (N-CH3), 56.8 (6-OCH3), 57.6 (3-OCH3), 62.0 (C-16), 77.7 (C-9), 112.2 (C-2), 120.0 (C-1), 122.1 (C-5), 124.7 (C-12), 126.1 (C-11), 127.5 (C-8), 145.7 (C-4), 148.7 (C-3), 152.0 (C-6), 158.4 (C-14), 182.2 (C-7)。1H NMR与13C NMR数据与文献[12]对照一致, 因此鉴定化合物8为salutaridine N-oxide。
化合物9  白色粉末; 1H NMR (400 MHz, CDCl3) δH: 1.88 (3H, s, N-CH3), 2.36~3.40 (6H, m, H-5, 6, 13), 3.74 (2H, d, J = 16.2 Hz, H-8), 3.76 (3H, s, 9-OCH3), 3.83 (3H, s, 10-OCH3), 5.90 (2H, s, 2-OCH2O-3), 6.61 (1H, s, H-1), 6.78 (1H, d, J = 8.2 Hz, H-12), 6.89 (1H, d, J = 8.2 Hz, H-11), 6.93 (1H, s, H-4); 13C NMR (150 MHz, CDCl3) δC: 32.3 (C-5), 41.3 (N-CH3), 44.8 (C-13), 50.8 (C-8), 55.7 (10-OCH3), 57.5 (C-6), 60.8 (9-OCH3), 101.3 (2-OCH2O-3), 109.2 (C-4), 110.4 (C-1), 110.7 (C-11), 127.7 (C-12), 128.5 (C-8a), 129.5 (C-12a), 132.8 (C-14a), 134.9 (C-4a), 146.1 (C-3), 147.4 (C-10), 148.1 (C-2), 151.1 (C-9), 191.9 (C-14)。1H NMR与13C NMR数据与文献[13]对照一致, 因此鉴定化合物9为allocryptopine。
化合物10  白色粉末; 1H NMR (400 MHz, CDCl3) δH: 1.94 (3H, s, N-CH3), 2.38~3.88 (8H, m, H-5, 6, 8, 13), 5.95 (2H, s, -OCH2O-), 5.97 (2H, s, -OCH2O-), 6.69 (3H, m, H-4, 11, 12), 6.92 (1H, s, H-1); 13C NMR (100 MHz, CDCl3) δC: 31.9 (C-5), 41.6 (N-CH3), 46.6 (C-13), 51.0 (C-8), 58.0 (C-6), 101.0 (-OCH2O-), 101.3 (-OCH2O-), 106.9 (C-11), 108.3 (C-1), 110.6 (C-4), 118.0 (C-8a), 125.2 (C-12), 129.1 (C-12a), 132.9 (C-14a), 136.3 (C-4a), 146.0 (C-10), 146.1 (C-9), 146.5 (C-2), 148.1 (C-3)。1H NMR与13C NMR数据与文献[14]对照一致, 因此鉴定化合物10为protopine。
化合物11  无色棱柱状晶体; 1H NMR (400 MHz, CDCl3) δH: 2.52 (3H, s, N-CH3), 2.72~3.04 (4H, m, H-3, 4), 3.32 (1H, m, H-9a), 3.55 (1H, dd, J = 18.4, 5.0 Hz, H-9b), 4.12 (1H, m, H-1), 5.95 (2H, s, 6-OCH2O-7), 6.06 (2H, s, 4′-OCH2O-5′), 6.40 (1H, d, J = 7.9 Hz, H-2′), 6.43 (1H, s, H-8), 6.60 (1H, s, H-5), 6.68 (1H, d, J = 7.9 Hz, H-H-3′); 13C NMR (100 MHz, CDCl3) δC: 24.5 (C-4), 42.1 (C-9), 42.8 (N-CH3), 48.5 (C-3), 66.7 (C-1), 101.4 (6-OCH2O-7), 101.9 (4′-OCH2O-5′), 107.7 (C-8), 108.4 (C-5), 108.9 (C-3′), 121.9 (C-6′), 123.9 (C-2′), 125.6 (C-4a), 125.9 (C-1′), 127.5 (C-8a), 146.9 (C-5′), 147.2 (C-7), 147.4 (C-6), 147.6 (C-4′), 169.1 (-COOH)。1H NMR与13C NMR数据与文献[15]对照一致, 因此鉴定化合物11为coryximine。
化合物12  黄色针晶; 1H NMR (400 MHz, CDCl3) δH: 2.00 (3H, s, N-CH3), 2.73 (2H, m, H-5), 3.27 (1H, m, H-6a), 3.50 (2H, m, H-6b), 3.71 (2H, m, H-13), 3.84 (2H, m, H-8), 3.89 (6H, s, 2, 3-OCH3), 5.93 (2H, s, 9-OCH2O-10), 6.68 (3H, m, H-11, 12, 4), 7.01 (1H, s, H-1); 13C NMR (100 MHz, CDCl3) δC: 31.7 (C-5), 41.7 (N-CH3), 45.6 (C-13), 51.0 (C-8), 56.1 (2, 3-OCH3), 57.5 (C-6), 101.1 (9-OCH2O-10), 107.2 (C-11), 112.1 (C-1), 113.4 (C-4), 116.8 (C-8a), 124.8 (C-12), 129.0 (C-12a), 130.5 (C-4a), 134.0 (C-14a), 146.2 (C-9), 146.3 (C-10), 147.4 (C-2), 149.6 (C-3), 180.6 (C-14)。1H NMR与13C NMR数据与文献[16]对照一致, 因此鉴定化合物12为cryptopine。
化合物13  白色针晶; 1H NMR (400 MHz, CD3OD) δH: 3.19 (1H, m, H-5a), 3.31 (6H, m, N-CH3, H-5b, 13), 3.49 (1H, dd, J = 18.4, 5.1 Hz, H-6a), 3.66 (1H, m, H-6b), 3.88 (1H, m, H-8a), 4.81 (2H, m, H-8b, 14), 6.00 (4H, m, 2-OCH2O-3, 9-OCH2O-10), 6.82 (4H, m, H-1, 4, 11, 12); 13C NMR (100 MHz, CD3OD) δC: 23.5 (C-5), 34.7 (C-13), 50.9 (N-CH3), 53.5 (C-6), 59.7 (C-8), 67.6 (C-14), 103.0 (2-OCH2O-3), 103.5 (9-OCH2O-10), 107.7 (C-4), 109.4 (C-11), 110.1 (C-1), 122.4 (C-12, 4a), 123.4 (C-8a), 123.8 (C-14a), 125.9 (C-12a), 145.6 (C-3), 148.0 (C-10), 148.6 (C-2), 150.1 (C-9)。1H NMR与13C NMR数据与文献[17]对照一致, 因此鉴定化合物13为cis-N-methylstylopine。
化合物14  无色晶体; 1H NMR (400 MHz, CDCl3) δH: 2.07 (3H, s, N-CH3), 2.78 (2H, m, H-5), 2.95 (2H, m, H-6), 3.69 (2H, m, H-13), 3.86 (2H, m, H-8), 3.87 (3H, s, 10-OCH3), 5.94 (2H, s, 2-OCH2O-3), 6.62 (1H, s, H-4), 6.69 (1H, d, J = 8.2 Hz, H-12), 6.75 (1H, d, J = 8.2 Hz, H-11), 6.95 (1H, s, H-1); 13C NMR (150 MHz, CDCl3) δC: 30.9 (C-5), 41.5 (N-CH3), 45.2 (C-13), 51.0 (C-8), 56.2 (10-OCH3), 57.1 (C-6), 101.4 (2-OCH2O-3), 108.7 (C-1), 109.4 (C-4), 110.2 (C-11), 128.0 (C-12, 8a), 129.7 (C-12a), 132.7 (C-4a), 135.6 (C-14a), 143.9 (C-9), 145.6 (C-2), 146.4 (C-3), 148.2 (C-10), 193.5 (C-14)。1H NMR与13C NMR数据与文献[18]对照一致, 因此鉴定化合物14为hunnemannine。
化合物15  黄色粉末, UV (MeOH) λmax log (ε) 200 (4.88), 290 (4.00), 380 (4.09) nm; 1H NMR (600 MHz, DMSO-d6) 和13C NMR (150 MHz, DMSO-d6) 数据见表1, 分子式为C18H16NO6+, HR-RES-MS m/z 342.091 8 [M]+ (计算值为342.097 3)。
3　抑制JBU活性的研究
3.1　对JBU抑制活性的筛选
在96孔板中分别加入50 µL浓度为0.25 mg‧mL-1的JBU溶液和一系列浓度梯度的娇嫩黄堇总生物碱及其11个生物碱单体, 于预设温度为37 ℃的多功能酶标仪中振荡混匀, 孵育20 min后加入100 µL尿素配制液, 振荡混匀后继续孵育20 min。然后加入Berthelot显色液(先加A液后加B液, 各25 µL), 混匀后反应10 min, 在酶标仪中测定635 nm处加入显色液前后10 min的吸光度, 计算OD实验值, 每个浓度测三组平行。加入相应体积的PBS-EDTA溶液作空白对照, 求得相应的OD空白值。根据公式1计算抑制率。
$ \text { 抑制率 }(\%)=\left(O D_{\text {空白 }}-O D_{\text {拉制制 }}\right) / O D_{\text {空白 }} \times 100 \% $
3.2　无机试剂对生物碱抑制JBU作用的测试
NaF是竞争性慢结合抑制剂与经典竞争性脲酶抑制剂BA通常作为竞争性抑制剂来研究抑制剂的抑制靶点是否为脲酶的活性位点Ni2+。为测试生物碱单体对JBU的抑制靶点是否为公认活性中心Ni2+, 在96孔板中以相同方法加入JBU溶液和5 mmol‧L-1BA或NaF, 孵育完成后, 加入Berthelot显色液, 反应10 min, 在酶标仪中测定635 nm处加入显色液前后10 min的吸光度, 测三组平行后根据公式2算出残余酶活性。以相同方法, 加入相应体积的PBS-EDTA溶液作空白对照, 测三组平行后算出残余酶活性。
$ \begin{aligned}\text { 残余酶活性 } \mathrm{RA}(\%)= & 100 \%-\left[\left(\mathrm{OD}_{\text {排制剂 }}-\right.\right. \\& \left.\left.\mathrm{OD}_{\text {空白 }}\right) / \mathrm{OD}_{\text {空白 }}\right] \%\end{aligned}$
4　娇嫩黄堇生物碱单体与JBU活性部位分子对接研究
从Protein Data Bank蛋白数据库中下载JBU蛋白三维结构(PDB ID: 3LA4), 分辨率2.05 Å。通过Dsicovery Studio 2019软件对其进行预处理, 在使用AutoDockTools软件将处理过的蛋白转化为pdbqt文件。将(-)-tetrahydrocorysamine (1) 单体的2D结构导入Chem3D软件中, 获取化合物的3D结构并进行能量优化, 并同样运行AutoDockTools软件进行预处理, 转化为pdbqt文件。以JBU活性中心的两个镍离子的平均坐标为中心, 形成对接的活性口袋。运用vina进行分子对接, 计算结果小于0 kcal‧mol-1则表明化合物可与蛋白结构相结合, 能量越低, 结构构象越稳定。
5　统计学分析
使用GraphPad Prism 8软件进行统计学分析, 所有实验组均重复3次(n = 3), 数据均采用$ \stackrel{-}{x} $ ± s表示, 两组间均数采用t检验进行比较, P < 0.05表示差异具有统计学意义。

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2025年第60卷第10期
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doi: 10.16438/j.0513-4870.2025-0323
  • 接收时间：2025-03-24
  • 首发时间：2026-09-20
  • 出版时间：2025-10-12
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  • 收稿日期：2025-03-24
  • 修回日期：2025-07-22
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    西南民族大学药学与食品学院, 四川 成都 610041

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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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