Article(id=1304406831938429376, tenantId=1146029695717560320, journalId=1302319053441957962, issueId=1304406818550206926, articleNumber=null, orderNo=null, doi=10.7501/j.issn.0253-2670.2026.01.004, pmid=null, cstr=null, oa=null, hot=0, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1760457600000, receivedDateStr=2025-10-15, revisedDate=null, revisedDateStr=null, acceptedDate=null, acceptedDateStr=null, onlineDate=1788924423441, onlineDateStr=2026-09-09, pubDate=null, pubDateStr=null, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1788924423441, onlineIssueDateStr=2026-09-09, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1788924423441, creator=13701087609, updateTime=1788924423441, updator=13701087609, issue=Issue{id=1304406818550206926, tenantId=1146029695717560320, journalId=1302319053441957962, year='2026', volume='57', issue='1', pageStart='1', pageEnd='389', issueExtLink='null', onlineDate='null', pubDate='1768147200000', pubDateStr='2026-01-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1788924420249, creator='13701087609', updateTime=1788924674802, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1304407886289986387, tenantId=1146029695717560320, journalId=1302319053441957962, issueId=1304406818550206926, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1304407886289986388, tenantId=1146029695717560320, journalId=1302319053441957962, issueId=1304406818550206926, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=31, endPage=38, ext={EN=ArticleExt(id=1304406832265585090, articleId=1304406831938429376, tenantId=1146029695717560320, journalId=1302319053441957962, language=EN, title=A new pyrrole alkaloid from fruit of Lycium barbarum, columnId=null, journalTitle=Chinese Traditional and Herbal Drugs, columnName=null, runingTitle=null, highlight=null, articleAbstract=Objective To research the chemical constituents from the fruits of Lycium barbarum. Methods Separation and purification were performed using silica gel, D-101 macroporous resin, MCI, Sephadex LH-20, and semi-preparative HPLC. The structures of the compounds were identified based on spectroscopic data and physicochemical properties. The α-glucosidase inhibitory activity of the selected compounds was evaluated using 4-nitrophenol-α-D-glucopyranoside (PNPG) assay. Results A total of 15 compounds were isolated from the fruits of L. barbarum, which were identified as methyl (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (1), 5-epi-acortatarin A (2), 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (3), 4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoic acid (4), (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(4-hydroxyphenyl) propanoate (5), 4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate (6), 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] pentanedioic acid (7), N-trans-feruloyl-3'-O-methyldopamine (8), N-trans-feruloyl-3',4'-dihydroxyphenylethylamine (9), N-cis-p-coumaroyl tyramine (10), N-cis-feruloyl tyramine (11), bungeanoline E (12), N-malonyl-tryptophan (13), 3-hydroxy-4-ethyl ketone pyridine (14), cartorimine (15). Conclusion Compound 1 is a new pyrrole alkaloid, named lycipyrrole A. Compound 2 is a new natural product. Compounds 4, 7 and 1215 were isolated from L. barbarum for the first time, while compounds 12, 13 and 15 were isolated from this genus for the first time. Notably, compound 9 exhibited significant inhibitory activity against α-glucosidase., authors=ZHAO Yongzhuo, NIU Ying, MA Yuguo, LIU Hui, SUN Jiaxin, HAO Zhiyou, FENG Weisheng, CHEN Hui, authorsList=ZHAO Yongzhuo, NIU Ying, MA Yuguo, LIU Hui, SUN Jiaxin, HAO Zhiyou, FENG Weisheng, CHEN Hui, authorCompany=null, correspAuthors=null, authorNote=null, correspAuthorsNote=null, copyrightStatement=null, 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=1304406832185893313, articleId=1304406831938429376, tenantId=1146029695717560320, journalId=1302319053441957962, language=CN, title=枸杞子中1个新的吡咯生物碱, columnId=1304140187169214944, journalTitle=中草药, columnName=化学成分, runingTitle=null, highlight=null, articleAbstract=目的 研究宁夏枸杞Lycium barbarum果实(枸杞子)的化学成分。方法 采用硅胶、D-101大孔吸附树脂、MCI、Sephadex LH-20等柱色谱及制备型HPLC色谱进行分离纯化,根据化合物的波谱数据和理化性质进行结构鉴定,并采用4-硝基苯酚-α-D-吡喃葡萄糖苷(4-nitrophenyl α-D-glucopyranoside,PNPG)法对部分化合物进行α-葡萄糖苷酶抑制活性评价。结果 从枸杞子中分离得到15个化合物,分别鉴定为methyl (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate(1)、5-epi-acortatarin A(2)、5-甲氧甲基-1H-吡咯-2-甲醛(3)、4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoic acid(4)、(2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(4-hydroxyphenyl)propanoate(5)、4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate(6)、3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid(7)、N-反式-阿魏酰-3-甲氧基酪胺(8)、N-trans-feruloyl-3′,4′-dihydroxyphenylethylamine(9)、N-顺式香豆酰酪胺(10)、N-顺式阿魏酰酪胺(11)、bungeanoline E(12)、N-malonyl-tryptophan(13)、3-羟基-4-乙基酮吡啶(14)、cartorimine(15)。化合物9抑制α-葡萄糖苷酶的半数抑制浓度(median inhibition concentration,IC₅₀)为(31.64±2.30)µmol/L。结论 化合物1为1个新的吡咯生物碱,命名为枸杞吡咯碱A,化合物2为1个新天然产物,化合物121315为首次从该属植物中分离得到,化合物4714为首次从宁夏枸杞植物中分离得到。化合物9具有显著的α-葡萄糖苷酶抑制作用。, authors=赵永卓1, 牛莹1, 马雨果1, 刘慧1, 孙嘉忻1, 郝志友1, 冯卫生1,2, 陈辉1,2, authorsList=赵永卓, 牛莹, 马雨果, 刘慧, 孙嘉忻, 郝志友, 冯卫生, 陈辉, authorCompany=1 河南中医药大学药学院, 河南 郑州 450046;
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王汉卿,王庆,马玲,等.枸杞子药材生产区划研究[J]. 中国中药杂志, 2016, 41(17):3127-3131.
中国药典[S]. 一部. 2020:260.
尚莹,朱一栋,张慧,等.枸杞子乙酸乙酯提取部位化学成分及生物活性研究[J]. 天然产物研究与开发,2025, 37(1):57-64.
Qian D, Zhao Y X, Yang G, et al. Systematic review of chemical constituents in the genus Lycium(Solanaceae)[J]. Molecules, 2017, 22(6):911.
Zhu Y J, Dai X Y, Zhao Y L, et al. Lyciumines A and B:Two pyrrole-fused alkaloids from the fruits of Lycium barbarum[J]. J Nat Prod, 2025, 88(5):1237-1243.
陈栋杰,郭盛,伊艳玲,等.枸杞属植物酰胺类成分及其生物活性研究进展[J]. 中草药, 2023, 54(1):317-333.
刘建飞,巩媛,杨军丽,等.枸杞属植物中生物碱类成分研究进展[J]. 科学通报, 2022, 67(S1):332-350.
Zhu P F, Zhao Y L, Dai Z, et al. Phenolic amides with immunomodulatory activity from the nonpolysaccharide fraction of Lycium barbarum fruits[J]. J Agric Food Chem, 2020, 68(10):3079-3087.
Chen H, Zhang W J, Kong J B, et al. Structurally diverse phenolic amides from the fruits of Lycium barbarum with potent α-glucosidase, dipeptidyl peptidase-4 inhibitory,and PPAR-γ agonistic activities[J]. J Agric Food Chem,2023, 71(29):11080-11093.
Xu G H, Kim Y H, Choo S J, et al. Chemical constituents from the leaves of Ilex paraguariensis inhibit human neutrophil elastase[J]. Arch Pharm Res, 2009, 32(9):1215-1220.
Youn U J, Lee J Y, Kil Y S, et al. Identification of new pyrrole alkaloids from the fruits of Lycium chinense[J]. Arch Pharm Res, 2016, 39(3):321-327.
Teranishi T, Kageyama M, Kuwahara S. Concise total synthesis of acortatarin A[J]. Biosci Biotechnol Biochem,2013, 77(3):676-678.
高莉,田华,吕培军,等.乌桕叶化学成分研究[J]. 中国中药杂志, 2015, 40(8):1518-1522.
胡梦雅,张文静,刘云,等.北方枸杞中生物碱类成分研究[J]. 中国中药杂志, 2023, 48(6):1546-1552.
姚会娜,张航,王文萱,等.小花黄堇中2个新苯丙酰胺苷类成分[J]. 中国中药杂志, 2020, 45(10):2411-2416.
杨炳友,卢震坤,刘艳,等.洋金花茎化学成分的分离鉴定[J]. 中国实验方剂学杂志, 2017, 23(17):34-40.
汪代芳,侴桂新,赵宁毅,等.金钗石斛茎的化学成分研究[J]. 中草药, 2012, 43(8):1492-1495.
袁湘,孙延平,王知斌,等.枸杞籽中苯丙素及含氮类化学成分研究[J]. 中草药, 2025, 56(19):6982-6989.
Han Y, Hou T, Zhang Z H, et al. Structurally diverse isoquinoline and amide alkaloids with dopamine D2receptor antagonism from Corydalis bungeana[J]. Fitoterapia, 2022, 159:105175.
King R R, Calhoun L A. Synthesis and NMR characteristics of N-acetyl-4-nitro, N-acetyl-5-nitro, Nacetyl-6-nitro and N-acetyl-7-nitrotryptophan methyl esters[J]. Magn Reson Chem, 2009, 47(3):273-276.
Yin H B, He Z S, Ye Y. Cartorimine, a new cycloheptenone oxide derivative from Carthamus tinctorius[J]. J Nat Prod, 2000, 63(8):1164-1165.
胡梦雅,范雨欣,徐瑞雯,等.北方枸杞化学成分及其α-葡萄糖苷酶抑制活性研究[J]. 中药材, 2024, 47(3):624-628.
Chen H, Kong J B, Zhang L, et al. Lycibarbarines A-C,three tetrahydroquinoline alkaloids possessing a spiroheterocycle moiety from the fruits of Lycium barbarum[J]. Org Lett, 2021, 23(3):858-862.)
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中草药 | 化学成分 2026,57(1): 31-38
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中草药 |化学成分 2026 , 57 (1) : 31 -38
枸杞子中1个新的吡咯生物碱
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赵永卓1, 牛莹1, 马雨果1, 刘慧1, 孙嘉忻1, 郝志友1, 冯卫生1,2, 陈辉1,2
作者信息
    1 河南中医药大学药学院, 河南 郑州 450046;
    2 呼吸疾病中医药防治省部共建协同创新中心, 河南 郑州 450046
通讯作者:
陈辉
作者简介:
赵永卓: 赵永卓(2000-),硕士研究生,研究方向为中药药效物质基础。E-mail:zyz4711@163.com
A new pyrrole alkaloid from fruit of Lycium barbarum
  • ZHAO Yongzhuo, NIU Ying, MA Yuguo, LIU Hui, SUN Jiaxin, HAO Zhiyou, FENG Weisheng, CHEN Hui
  • Affiliations
    doi: 10.7501/j.issn.0253-2670.2026.01.004
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    目的 研究宁夏枸杞Lycium barbarum果实(枸杞子)的化学成分。方法 采用硅胶、D-101大孔吸附树脂、MCI、Sephadex LH-20等柱色谱及制备型HPLC色谱进行分离纯化,根据化合物的波谱数据和理化性质进行结构鉴定,并采用4-硝基苯酚-α-D-吡喃葡萄糖苷(4-nitrophenyl α-D-glucopyranoside,PNPG)法对部分化合物进行α-葡萄糖苷酶抑制活性评价。结果 从枸杞子中分离得到15个化合物,分别鉴定为methyl (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate(1)、5-epi-acortatarin A(2)、5-甲氧甲基-1H-吡咯-2-甲醛(3)、4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoic acid(4)、(2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(4-hydroxyphenyl)propanoate(5)、4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate(6)、3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]pentanedioic acid(7)、N-反式-阿魏酰-3-甲氧基酪胺(8)、N-trans-feruloyl-3′,4′-dihydroxyphenylethylamine(9)、N-顺式香豆酰酪胺(10)、N-顺式阿魏酰酪胺(11)、bungeanoline E(12)、N-malonyl-tryptophan(13)、3-羟基-4-乙基酮吡啶(14)、cartorimine(15)。化合物9抑制α-葡萄糖苷酶的半数抑制浓度(median inhibition concentration,IC₅₀)为(31.64±2.30)µmol/L。结论 化合物1为1个新的吡咯生物碱,命名为枸杞吡咯碱A,化合物2为1个新天然产物,化合物121315为首次从该属植物中分离得到,化合物4714为首次从宁夏枸杞植物中分离得到。化合物9具有显著的α-葡萄糖苷酶抑制作用。
    茄科  /  枸杞子  /  生物碱  /  α-葡萄糖苷酶抑制活性  /  枸杞吡咯碱A  /  5-epi-acortatarin A  /  3-羟基-4-乙基酮吡啶
    Objective To research the chemical constituents from the fruits of Lycium barbarum. Methods Separation and purification were performed using silica gel, D-101 macroporous resin, MCI, Sephadex LH-20, and semi-preparative HPLC. The structures of the compounds were identified based on spectroscopic data and physicochemical properties. The α-glucosidase inhibitory activity of the selected compounds was evaluated using 4-nitrophenol-α-D-glucopyranoside (PNPG) assay. Results A total of 15 compounds were isolated from the fruits of L. barbarum, which were identified as methyl (2R)-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl]-4-methylpentanoate (1), 5-epi-acortatarin A (2), 5-(methoxymethyl)-1H-pyrrole-2-carbaldehyde (3), 4-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoic acid (4), (2R)-[2-formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]-3-(4-hydroxyphenyl) propanoate (5), 4-[formyl-5-(methoxymethyl)-1H-pyrrol-1-yl]butanoate (6), 3-[2-formyl-5-(hydroxymethyl)-1H-pyrrol-1-yl] pentanedioic acid (7), N-trans-feruloyl-3'-O-methyldopamine (8), N-trans-feruloyl-3',4'-dihydroxyphenylethylamine (9), N-cis-p-coumaroyl tyramine (10), N-cis-feruloyl tyramine (11), bungeanoline E (12), N-malonyl-tryptophan (13), 3-hydroxy-4-ethyl ketone pyridine (14), cartorimine (15). Conclusion Compound 1 is a new pyrrole alkaloid, named lycipyrrole A. Compound 2 is a new natural product. Compounds 4, 7 and 1215 were isolated from L. barbarum for the first time, while compounds 12, 13 and 15 were isolated from this genus for the first time. Notably, compound 9 exhibited significant inhibitory activity against α-glucosidase.
    Solanaceae  /  Lycium barbarum L.  /  alkaloids  /  α-glucosidase inhibitory activity  /  lycipyrrole A  /  5-epi-acortatarin A  /  3-hydroxy-4-ethyl ketone pyridine
    赵永卓, 牛莹, 马雨果, 刘慧, 孙嘉忻, 郝志友, 冯卫生, 陈辉. 枸杞子中1个新的吡咯生物碱. 中草药, 2026 , 57 (1) : 31 -38 . DOI: 10.7501/j.issn.0253-2670.2026.01.004
    ZHAO Yongzhuo, NIU Ying, MA Yuguo, LIU Hui, SUN Jiaxin, HAO Zhiyou, FENG Weisheng, CHEN Hui. A new pyrrole alkaloid from fruit of Lycium barbarum[J]. Chinese Traditional and Herbal Drugs, 2026 , 57 (1) : 31 -38 . DOI: 10.7501/j.issn.0253-2670.2026.01.004

      国家自然科学基金资助项目 (22177027); 河南省高校科技创新团队支持计划 (24IRTSTHN039); 河南省杰出青年科学基金项目 (252300421027)

    参考文献 引证文献
    排序方式:
    范雨欣,徐瑞雯,张晓祎,等.中华枸杞中1个新的香豆素葡萄糖苷[J]. 中草药, 2024, 55(1):23-29.
    张文静,范雨欣,胡梦雅,等.枸杞子中1个新的环香叶烷类单萜[J]. 中草药, 2022, 53(21):6653-6659.
    王汉卿,王庆,马玲,等.枸杞子药材生产区划研究[J]. 中国中药杂志, 2016, 41(17):3127-3131.
    中国药典[S]. 一部. 2020:260.
    尚莹,朱一栋,张慧,等.枸杞子乙酸乙酯提取部位化学成分及生物活性研究[J]. 天然产物研究与开发,2025, 37(1):57-64.
    Qian D, Zhao Y X, Yang G, et al. Systematic review of chemical constituents in the genus Lycium(Solanaceae)[J]. Molecules, 2017, 22(6):911.
    Zhu Y J, Dai X Y, Zhao Y L, et al. Lyciumines A and B:Two pyrrole-fused alkaloids from the fruits of Lycium barbarum[J]. J Nat Prod, 2025, 88(5):1237-1243.
    陈栋杰,郭盛,伊艳玲,等.枸杞属植物酰胺类成分及其生物活性研究进展[J]. 中草药, 2023, 54(1):317-333.
    刘建飞,巩媛,杨军丽,等.枸杞属植物中生物碱类成分研究进展[J]. 科学通报, 2022, 67(S1):332-350.
    Zhu P F, Zhao Y L, Dai Z, et al. Phenolic amides with immunomodulatory activity from the nonpolysaccharide fraction of Lycium barbarum fruits[J]. J Agric Food Chem, 2020, 68(10):3079-3087.
    Chen H, Zhang W J, Kong J B, et al. Structurally diverse phenolic amides from the fruits of Lycium barbarum with potent α-glucosidase, dipeptidyl peptidase-4 inhibitory,and PPAR-γ agonistic activities[J]. J Agric Food Chem,2023, 71(29):11080-11093.
    Xu G H, Kim Y H, Choo S J, et al. Chemical constituents from the leaves of Ilex paraguariensis inhibit human neutrophil elastase[J]. Arch Pharm Res, 2009, 32(9):1215-1220.
    Youn U J, Lee J Y, Kil Y S, et al. Identification of new pyrrole alkaloids from the fruits of Lycium chinense[J]. Arch Pharm Res, 2016, 39(3):321-327.
    Teranishi T, Kageyama M, Kuwahara S. Concise total synthesis of acortatarin A[J]. Biosci Biotechnol Biochem,2013, 77(3):676-678.
    高莉,田华,吕培军,等.乌桕叶化学成分研究[J]. 中国中药杂志, 2015, 40(8):1518-1522.
    胡梦雅,张文静,刘云,等.北方枸杞中生物碱类成分研究[J]. 中国中药杂志, 2023, 48(6):1546-1552.
    姚会娜,张航,王文萱,等.小花黄堇中2个新苯丙酰胺苷类成分[J]. 中国中药杂志, 2020, 45(10):2411-2416.
    杨炳友,卢震坤,刘艳,等.洋金花茎化学成分的分离鉴定[J]. 中国实验方剂学杂志, 2017, 23(17):34-40.
    汪代芳,侴桂新,赵宁毅,等.金钗石斛茎的化学成分研究[J]. 中草药, 2012, 43(8):1492-1495.
    袁湘,孙延平,王知斌,等.枸杞籽中苯丙素及含氮类化学成分研究[J]. 中草药, 2025, 56(19):6982-6989.
    Han Y, Hou T, Zhang Z H, et al. Structurally diverse isoquinoline and amide alkaloids with dopamine D2receptor antagonism from Corydalis bungeana[J]. Fitoterapia, 2022, 159:105175.
    King R R, Calhoun L A. Synthesis and NMR characteristics of N-acetyl-4-nitro, N-acetyl-5-nitro, Nacetyl-6-nitro and N-acetyl-7-nitrotryptophan methyl esters[J]. Magn Reson Chem, 2009, 47(3):273-276.
    Yin H B, He Z S, Ye Y. Cartorimine, a new cycloheptenone oxide derivative from Carthamus tinctorius[J]. J Nat Prod, 2000, 63(8):1164-1165.
    胡梦雅,范雨欣,徐瑞雯,等.北方枸杞化学成分及其α-葡萄糖苷酶抑制活性研究[J]. 中药材, 2024, 47(3):624-628.
    Chen H, Kong J B, Zhang L, et al. Lycibarbarines A-C,three tetrahydroquinoline alkaloids possessing a spiroheterocycle moiety from the fruits of Lycium barbarum[J]. Org Lett, 2021, 23(3):858-862.
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    doi: 10.7501/j.issn.0253-2670.2026.01.004
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    2种不同金属材料的力学参数

    Family
    属数
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    genus
    种数
    Number of
    species
    占总种数比例
    Percentage of
    total species (%)

    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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