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Article(id=1308455935958078198, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308455335962894804, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2025-0087, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1737561600000, receivedDateStr=2025-01-23, revisedDate=1742745600000, revisedDateStr=2025-03-24, acceptedDate=null, acceptedDateStr=null, onlineDate=1789889805067, onlineDateStr=2026-09-20, pubDate=1749657600000, pubDateStr=2025-06-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1789889805067, onlineIssueDateStr=2026-09-20, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1789889805067, creator=13701087609, updateTime=1789889805067, updator=13701087609, issue=Issue{id=1308455335962894804, tenantId=1146029695717560320, journalId=1189982191388893191, year='2025', volume='60', issue='6', pageStart='1573', pageEnd='1964', issueExtLink='null', onlineDate='null', pubDate='1749657600000', pubDateStr='2025-06-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1789889662017, creator='13701087609', updateTime=1789893590327, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1308471812564734358, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308455335962894804, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1308471812564734359, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1308455335962894804, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=1855, endPage=1860, ext={EN=ArticleExt(id=1308455936197153527, articleId=1308455935958078198, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Two new prototerpenoid triterpenoids from Alisma plantago-aquatica, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Seventeen compounds were isolated from the ethyl acetate extract of the tubers of dry Alisma plantago-aquatica by silica gel, Sephadex LH-20 and high performance liquid chromatography. All of them were identified as the prototerpene triterpenoids by the analysis of mass spectrometry and nuclear magnetic resonance spectroscopy. Compounds 1 and 2 are the new compounds. Among of them, 16 compounds were screened for α-glucosidase inhibitory activity, however, none of them was active.

, authors=Lan-zhu ZHU, Yu-lin ZHANG, Xiao-yu ZONG, Rui SHANG, Xuan-qin CHEN*, authorsList=Lan-zhu ZHU, Yu-lin ZHANG, Xiao-yu ZONG, Rui SHANG, Xuan-qin CHEN, authorCompany=null, correspAuthors=Xuan-qin CHEN, 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=1308455938717930238, articleId=1308455935958078198, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=泽泻中的两个新原萜烷型三萜, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶、凝胶(Sephadex LH-20) 和高效液相色谱等色谱分离技术, 从泽泻(Alisma plantago-aquatica Linn) 干燥块茎的乙酸乙酯相中分离得到17个化合物, 通过质谱和核磁共振等波谱学方法, 鉴定均为原萜烷型三萜(1~17), 其中化合物1和化合物2为新化合物。对其中16个化合物进行了抑制α-葡萄糖苷酶活性筛选, 发现它们均无抑制α-葡萄糖苷酶活性。

, authors=朱兰珠, 张玉林, 宗晓语, 尚蕊, 陈宣钦*, authorsList=朱兰珠, 张玉林, 宗晓语, 尚蕊, 陈宣钦, authorCompany=null, correspAuthors=陈宣钦, authorNote=

作者贡献

陈宣钦负责课题的设计和稿件修订; 朱兰珠负责药材的提取、实验实施、数据核实、文章撰写和化合物的活性筛选工作; 张玉林负责技术指导和实验实施; 宗晓语负责药材的提取和实验实施; 尚蕊负责药材的实验实施和修改论文。

, correspAuthorsNote=
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Intervention effects of the extract of Alismatis Rhizoma on streptozotocin-induced type 2 diabetic rats [J]. J China Pharm Univ (中国药科大学学报), 2017, 48: 601-608., articleTitle=null, refAbstract=null), Reference(id=1308497703890411592, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308455935958078198, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=29, rfOrder=28, authorNames=null, journalName=null, refType=null, unstructuredReference=Zhang YL, Li SQ, Zhu LZ, et al. Phenolic acid compounds from Phellodendron chinense and their activity on α-glucosidase inhibition [J]. 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No.12
δH (J in Hz)δC, mult.δH (J in Hz)δC, mult.
11.60 m
1.64 m		31.2 (t)1.63 m
2.14 m		32.5 (t)
22.29 m
2.70 m		33.7 (t)1.47 m
2.80 m		33.4 (t)
3220.4 (s)223.2 (s)
447.3 (s)48.3 (s)
52.32 m46.4 (d)2.36 m47.6 (d)
61.26 m
1.34 m		19.4 (t)1.39 m
2.10 m		20.4 (t)
71.48 m
1.90 m		32.3 (t)1.33 m
1.90 m		34.5 (t)
838.2 (s)39.0 (s)
92.27 m47.3 (d)2.32 m48.3 (d)
1036.0 (s)36.9 (s)
116.25 dd (10.0, 3.3)121.1 (d)6.32 dd (10.0, 3.3)123.1 (d)
125.65 d (10.0)129.9 (d)5.56 d (10.0)128.4 (d)
13138.5 (s)141.5 (s)
1455.0 (s)56.4 (s)
151.40 m
2.10 m		37.0 (t)1.81 m
2.28 m		30.0 (t)
164.54 d (8.8)80.1 (d)1.40 m
2.26 m		29.4 (t)
17135.3 (s)139.3 (s)
181.09 s24.8 (q)0.98 s23.4 (q)
190.89 s24.9 (q)0.85 s20.9 (q)
202.96 m27.4 (d)2.96 m28.7 (d)
211.17 d (7.2)17.9 (q)1.01 d (7.0)20.7 (q)
221.37 m
1.74 m		36.3 (t)1.42 m
1.45 m		40.0 (t)
233.60 m73.0 (d)3.11 m70.2 (d)
242.71 d (7.8)65.8 (d)2.60 d (8.5)69.6 (d)
2557.4 (s)59.9 (s)
261.31 s19.4 (q)1.23 s19.7 (q)
271.31 s25.2(q)1.18 s25.3 (q)
281.07 s29.4 (q)1.04 s29.5 (q)
291.04 s19.3 (q)0.98 s19.8 (q)
300.86 s22.7 (q)0.87 s25.1 (q)
), ArticleFig(id=1308497701138948139, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1308455935958078198, language=CN, label=Tab.1, caption=

1H (600 MHz) and 13C NMR (151 MHz) data of 1 (CDCl3) and 2 (CD3OD)

, figureFileSmall=null, figureFileBig=null, tableContent=
No.12
δH (J in Hz)δC, mult.δH (J in Hz)δC, mult.
11.60 m
1.64 m		31.2 (t)1.63 m
2.14 m		32.5 (t)
22.29 m
2.70 m		33.7 (t)1.47 m
2.80 m		33.4 (t)
3220.4 (s)223.2 (s)
447.3 (s)48.3 (s)
52.32 m46.4 (d)2.36 m47.6 (d)
61.26 m
1.34 m		19.4 (t)1.39 m
2.10 m		20.4 (t)
71.48 m
1.90 m		32.3 (t)1.33 m
1.90 m		34.5 (t)
838.2 (s)39.0 (s)
92.27 m47.3 (d)2.32 m48.3 (d)
1036.0 (s)36.9 (s)
116.25 dd (10.0, 3.3)121.1 (d)6.32 dd (10.0, 3.3)123.1 (d)
125.65 d (10.0)129.9 (d)5.56 d (10.0)128.4 (d)
13138.5 (s)141.5 (s)
1455.0 (s)56.4 (s)
151.40 m
2.10 m		37.0 (t)1.81 m
2.28 m		30.0 (t)
164.54 d (8.8)80.1 (d)1.40 m
2.26 m		29.4 (t)
17135.3 (s)139.3 (s)
181.09 s24.8 (q)0.98 s23.4 (q)
190.89 s24.9 (q)0.85 s20.9 (q)
202.96 m27.4 (d)2.96 m28.7 (d)
211.17 d (7.2)17.9 (q)1.01 d (7.0)20.7 (q)
221.37 m
1.74 m		36.3 (t)1.42 m
1.45 m		40.0 (t)
233.60 m73.0 (d)3.11 m70.2 (d)
242.71 d (7.8)65.8 (d)2.60 d (8.5)69.6 (d)
2557.4 (s)59.9 (s)
261.31 s19.4 (q)1.23 s19.7 (q)
271.31 s25.2(q)1.18 s25.3 (q)
281.07 s29.4 (q)1.04 s29.5 (q)
291.04 s19.3 (q)0.98 s19.8 (q)
300.86 s22.7 (q)0.87 s25.1 (q)
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泽泻中的两个新原萜烷型三萜
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朱兰珠 , 张玉林 , 宗晓语 , 尚蕊 , 陈宣钦 *
药学学报 | 研究论文 2025,60(6): 1855-1860
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药学学报 |研究论文 2025 , 60 (6) : 1855 -1860
泽泻中的两个新原萜烷型三萜
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朱兰珠, 张玉林, 宗晓语, 尚蕊, 陈宣钦*
作者信息
  • 昆明理工大学生命科学与技术学院, 云南 昆明 650500
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作者贡献

陈宣钦负责课题的设计和稿件修订; 朱兰珠负责药材的提取、实验实施、数据核实、文章撰写和化合物的活性筛选工作; 张玉林负责技术指导和实验实施; 宗晓语负责药材的提取和实验实施; 尚蕊负责药材的实验实施和修改论文。

Two new prototerpenoid triterpenoids from Alisma plantago-aquatica
Lan-zhu ZHU, Yu-lin ZHANG, Xiao-yu ZONG, Rui SHANG, Xuan-qin CHEN*
Affiliations
  • Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, China
出版时间: 2025-06-12 doi: 10.16438/j.0513-4870.2025-0087
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摘要
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采用硅胶、凝胶(Sephadex LH-20) 和高效液相色谱等色谱分离技术, 从泽泻(Alisma plantago-aquatica Linn) 干燥块茎的乙酸乙酯相中分离得到17个化合物, 通过质谱和核磁共振等波谱学方法, 鉴定均为原萜烷型三萜(1~17), 其中化合物1和化合物2为新化合物。对其中16个化合物进行了抑制α-葡萄糖苷酶活性筛选, 发现它们均无抑制α-葡萄糖苷酶活性。

泽泻  /  原萜烷型三萜  /  乙酸乙酯相  /  α-葡萄糖苷酶抑制活性

Seventeen compounds were isolated from the ethyl acetate extract of the tubers of dry Alisma plantago-aquatica by silica gel, Sephadex LH-20 and high performance liquid chromatography. All of them were identified as the prototerpene triterpenoids by the analysis of mass spectrometry and nuclear magnetic resonance spectroscopy. Compounds 1 and 2 are the new compounds. Among of them, 16 compounds were screened for α-glucosidase inhibitory activity, however, none of them was active.

Alisma plantago-aquatica  /  proterpane-type triterpenes  /  ethyl acetate phase  /  α-glucosidase inhibitory activity
朱兰珠, 张玉林, 宗晓语, 尚蕊, 陈宣钦. 泽泻中的两个新原萜烷型三萜. 药学学报, 2025 , 60 (6) : 1855 -1860 . DOI: 10.16438/j.0513-4870.2025-0087
Lan-zhu ZHU, Yu-lin ZHANG, Xiao-yu ZONG, Rui SHANG, Xuan-qin CHEN. Two new prototerpenoid triterpenoids from Alisma plantago-aquatica[J]. Acta Pharmaceutica Sinica, 2025 , 60 (6) : 1855 -1860 . DOI: 10.16438/j.0513-4870.2025-0087
正文
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泽泻始载于《神农本草经》, 列为上品; 《本草纲目》等历代医著都有关于泽泻的记载[1]。六味地黄丸(熟地黄、酒萸肉、牡丹皮、山药、茯苓、泽泻)[2]、龙胆泻肝汤(龙胆草、黄芩、栀子、泽泻、木通、车前子等)[3]、泽泻汤(泽泻、白术)[4]等经典名方中均有泽泻的配伍使用。古代使用的泽泻主流基原植物为泽泻属泽泻Alisma plantago-aquatica与东方泽泻Alisma orientale[4]。泽泻在中国药典(1963年版) 中便开始收录, 中国药典(2020年版) 收载的泽泻药材为泽泻科植物东方泽泻Alisma orientale (Sam.) Juzep.或泽泻Alisma plantago-aquatica Linn的干燥块茎[5], 其广泛种植于江西、广东、广西、福建、四川等地, 是四川和福建的道地药材[6]。泽泻性寒, 味甘、淡, 归肾、膀胱经, 具有利水渗湿、泄热、化浊调脂的功效, 可用于小便不利、水肿胀满、泄泻尿少、痰饮眩晕、热淋涩痛、高脂血症等[7]。
植物化学研究表明泽泻中的化学成分主要为三萜和倍半萜, 其他还有糖类、含氮化合物、苯丙素、黄酮、甾体和二萜等[8]。原萜烷型四环三萜及愈创木烷型倍半萜为泽泻的特征化合物[9]。到目前为止, 已经从泽泻中分离鉴定出共约118种三萜类化合物[1], 主要成分包括泽泻醇A、泽泻醇B、23-乙酰泽泻醇B、23-乙酰泽泻醇C和24-乙酰泽泻醇A等化合物, 其中, 23-乙酰泽泻醇B为泽泻中含量最高的三萜类成分[10], 23-乙酰泽泻醇B和23-乙酰泽泻醇C是《中国药典, 2020版》收录的泽泻的质量控制标志物[5]。现代药理学研究表明泽泻具有利尿[11, 12]、抗结石及肾脏保护[13, 14]、降血脂及保肝[15, 16]、降血糖[17]、抗癌[18]、抗氧化损伤[19]、抗炎[20]、抗骨质疏松[21]、抗菌[22]和抗病毒[9]等多种药理活性。本文从泽泻干燥块茎95%乙醇提取物的乙酸乙酯相中分离得到17个原萜烷型三萜(图1), 分别鉴定为Δ11, 12 alisol Ⅰ (1)、Δ11, 1211-deoxyalisol B (2)、11-deoxyalisol B 23-acetate (3)、11-deoxyalisol B (4)、11-anhydro-alisol F (5)、16S, 24S-dihydroxy-24-deacetyl alisol O (6)、alisol B 23-acetate (7)、16, 23-oxidoalisol B (8)、25-anhydroalisol F (9)、alisol N 23-acetate (10)、11-deoxyalisol C 23-acetate (11)、11-deoxy-25-anhydroalisol E (12)、16β-hydroxyalisol B acetate (13)、11-deoxyalisol A (14)、16β-methoxyalisol B monoacetate (15)、13(17), 15-dehydroalisol B 23-acetate (16) 和alisol R (17), 并对1和3~17进行了抑制α-葡萄糖苷酶活性评价。
结果与讨论
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1　结构鉴定
化合物1为白色无定形粉, 通过HR-ESI-MS的准分子离子峰m/z 475.317 7 [M+Na]+ (计算值475.318 3, C30H44O3Na) 确定其分子式为C30H44O3, 不饱和度为9。化合物1的1H NMR谱(表1) 显示了2个烯键氢信号δH 6.25 (1H, dd, J = 10.0, 3.3 Hz, H-11) 和5.65 (1H, d, J = 10.0 Hz, H-12), 3个含氧甲基质子信号δH 4.54 (1H, d, J = 8.8 Hz, H-16)、3.60 (1H, m, H-23) 和2.71 (1H, d, J = 7.8 Hz, H-24), 8个甲基信号δH 0.86 (3H, s, H-30)、0.89 (3H, s, H-19)、1.04 (3H, s, H-29)、1.07 (3H, s, H-28)、1.09 (3H, s, H-18)、1.17 (3H, d, J = 7.2 Hz, H-21)、1.31 (3H, s, H-26) 和1.31 (3H, s, H-27)。化合物1的13C NMR (表1) 谱显示了30个碳信号, 结合DEPT谱, 包括8个甲基碳信号, 6个亚甲基碳信号, 3个次甲基碳信号, 4个季碳信号, 4个含氧甲基, 以及两对双键碳信号和1个酮羰基碳信号。
化合物1的波谱数据与alisol Ⅰ[23]非常相似, 主要区别在于alisol Ⅰ中的两个亚甲基信号(C-11和-C12) 在化合物1中转变为两个烯碳信号, 推测化合物1是alisol Ⅰ的C-11和C-12脱氢衍生物。HMBC谱(图2) 中, H-9到C-8、C-10和C-11、H-11到C-9和C-13及H-12到C-9和C-13的相关进一步证实了化合物1中C-11和C-12位之间双键的存在。
化合物1的相对构型通过生源途径、ROESY谱分析(图3) 和与已知化合物对比化学位移综合确定。从生源角度考虑, 天然存在的原萜烷型三萜的Me-18、Me-21和Me-28为α构型, Me-19、Me-29和Me-30为β构型, H-5为α构型, H-9为β构型。在ROESY谱中, H-16/Me-18以及H-16/H-23的ROESY相关, 说明H-16和H-23均为α取向, 即16, 23-环氧为β取向。化合物1的H-24与C-24的化学位移与alisol Ⅰ [alisol Ⅰ: δH-24 2.78, δC-24 65.7; 1: δH-24 2.71, δC-24 65.8] 非常相似, 可以确定C-24的绝对构型应与alisol Ⅰ一致, 即24R。综上所述, 化合物1的结构被确定为Δ11, 12 alisol Ⅰ。
化合物2为无色油状物, 通过HR-ESI-MS中的准分子离子峰m/z 477.334 7 [M+Na]+ (计算值477.333 9, C30H46O3Na) 确定其分子式为C30H46O3, 不饱和度为8。化合物2的1H NMR (表1) 显示2个烯键氢信号δH 6.33 (1H, dd, J = 10.0, 3.3 Hz, H-11) 和5.56 (1H, d, J = 10.0 Hz, H-12), 2个含氧甲基质子信号δH 3.11 (1H, m, H-23) 和2.60 (1H, d, J = 8.5 Hz, H-24), 8个甲基信号δH 0.85 (3H, s, H-30)、0.87 (3H, s, H-19)、0.98 (3H, s, H-29)、0.99 (3H, s, H-18)、1.01 (3H, d, J = 7.0 Hz, H-21)、1.03 (3H, s, H-28)、1.18 (3H, s, H-26) 和1.23 (3H, s, H-27)。化合物2的13C NMR (表1) 谱显示了30个碳信号, 结合DEPT谱, 包括8个甲基碳信号, 7个亚甲基碳信号, 3个次甲基碳信号, 4个季碳信号, 3个含氧甲基, 以及两对双键碳信号和1个酮羰基碳信号。
化合物2的上述NMR数据与11-deoxyalisol B (4)[24]非常相似, 主要区别是11-deoxyalisol B中的C-11和C-12亚甲基在化合物2中转变为烯碳, 化合物2是11-deoxyalisol B的C-11和C-12脱氢衍生物。HMBC谱(图2) 中, H-9到C-5、C-10和C-11, H-11到C-9和C-13及H-12到C-9和C-13的相关进一步证实了Δ11, 12双键的存在。
化合物2的相对构型通过生源途径和与已知化合物对比化学位移确定。从生源角度考虑, Me-18、Me-21和Me-28为α构型, Me-19、Me-29和Me-30为β构型, H-5为α构型, H-9为β构型。通过与11-deoxyalisol B化学位移比较[11-deoxyalisol B: δH-23 3.23, δC-23 69.2, δH-24 2.70, δC-24 67.8; 2: δH-23 3.25, δC-23 69.1, δH-24 2.69, δC-24 67.9] 可确定C-23和C-24的绝对构型应与11-deoxyalisol B一致, 即23S和24R。综上所述, 化合物2最终被确定为Δ11, 1211-deoxyalisol B。
2　 α-葡萄糖苷酶活性评价
采用α-葡萄糖苷酶诱导4-硝基苯基-α-吡喃葡萄糖苷(pNPG) 生成对硝基苯酚(pNP) 的体外筛选模型, 对化合物1和3~17进行了抑制α-葡萄糖苷酶活性评价。在50 μmol·L-1浓度下化合物均未对α-葡萄糖苷酶表现出明显的抑制活性。
3　讨论
研究表明, 泽泻及其单体化合物具有一定的降血糖活性。Zhang等[25]发现23-乙酰泽泻醇B可以降低2型糖尿病小鼠血糖, 促进前脂肪细胞分化和葡萄糖吸收。Chen等[26]发现24-乙酰泽泻醇A能够促进C2C12肌管葡萄糖的摄取。泽泻正丁醇萃取部分可显著降低小鼠体内α-葡萄糖苷酶活性, 乙酸乙酯部位可有效调节体内糖和脂代谢, 对2型糖尿病有一定治疗作用[27, 28]。糖尿病治疗药物靶点众多, 其中, α-葡萄糖苷酶抑制剂通过抑制多糖的水解, 阻止小肠对葡萄糖的吸收, 达到降血糖的效果。目前上市的α-葡萄糖苷酶抑制剂主要包括伏格列波糖、阿卡波糖和米格列醇, 但是也有一些不良反应, 主要表现为腹部不适。寻找新型安全的α-葡萄糖苷酶抑制剂仍然具有一定的临床需求。本研究对从泽泻中分离得到的16个化合物进行了抑制α-葡萄糖苷酶活性筛选, 但是它们均无明显的活性。
实验部分
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BrukerAvance Ⅲ HD 600 MHz核磁共振波谱仪; Q Exactive液相色谱超高分辨质谱联用仪(美国Thermo公司); Agilent 1260型高效液相色谱仪, 配备ZORBAX SB-C18反相柱(分析型: 150 mm × 4.6 mm, 1 mL·min-1; 半制备型: 9.4 mm × 250 mm, 3 mL·min-1) 和二极管阵列检测器(美国Agilent公司); Hei-VAP Value G3型旋转蒸发仪(德国Heidolph公司); 薄层色谱硅胶GF254、柱色谱硅胶(青岛海洋化工厂); SephadexLH-20 (瑞典GE Healthcare Biosciences公司); ODS-C18 (75 μm) 反相填充材料(日本YMC公司); DMSO (北京Solarbio公司); α-葡萄糖苷酶、对硝基苯基-α-D-吡喃葡萄糖苷(pNPG, 上海源叶生物科技有限公司)。
泽泻(Alisma plantago-aquatica Linn) 干燥块茎于2023年8月购自昆明螺蛳湾药材市场, 并由昆明理工大学李洪梅教授鉴定, 样品标本(KUST0801) 存于昆明理工大学生命科学技术大楼资源药物化学重点实验室。
1　提取与分离
干燥的泽泻块茎(25.0 kg) 粉碎后, 在室温下用95%乙醇浸渍提取3次, 提取液合并, 减压浓缩得到浸膏。浸膏依次用石油醚、乙酸乙酯和正丁醇萃取, 分别得到石油醚相(200.0 g)、乙酸乙酯相(450.0 g) 和正丁醇相(50.0 g)。乙酸乙酯相(450.0 g) 经硅胶柱层析(石油醚-乙酸乙酯, 100∶1~0∶1), TLC检测合并相同组分后, 得到7个组分(Fr.1~Fr.7)。
Fr.2 (41.0 g) 经过硅胶柱色谱(石油醚-乙酸乙酯, 50∶1~0∶1) 分离, 得到3个组分, Fr.2.1~Fr.2.3。Fr.2.1 (9.1 g) 经过硅胶柱(二氯甲烷-乙酸乙酯, 80∶1) 纯化, 得到4个组分, Fr.2.1.1~Fr.2.1.4。Fr.2.1.4 (2.2 g) 经过硅胶柱(二氯甲烷-丙酮, 90∶1) 分离纯化, 得到2个组分, Fr.2.1.4.1~Fr.2.1.4.2。通过半制备HPLC (90%甲醇水) 纯化, 从Fr.2.1.4.2 (931.6 mg) 中得到化合物1 (5.1 mg)、化合物3 (9.4 mg) 和化合物4 (95.8 mg)。
Fr.3 (43.0 g) 经过硅胶柱色谱(二氯甲烷-乙酸乙酯, 100∶1~0∶1) 分离纯化, 得到4个组分, Fr.3.1~Fr.3.4。Fr.3.1 (15.8 g) 经过硅胶柱(石油醚-乙酸乙酯, 10∶1) 纯化, 得到3个组分, Fr.3.1.1~Fr.3.1.3。Fr.3.1.1 (12.0 g) 先后经过3次硅胶柱(流动相分别为石油醚-异丙醇, 45∶1; 二氯甲烷-甲醇, 150∶1; 氯仿-异丙醇, 120∶1) 和Sephadex LH-20柱(甲醇) 分离纯化, 得到化合物2 (2.8 mg)、化合物5 (3.4 mg) 和化合物6 (4.0 mg)。
Fr.4 (25.0 g) 经过硅胶柱(二氯甲烷-甲醇, 70∶1~0∶1) 分离纯化, 得到Fr.4.1~Fr.4.4。Fr.4.2 (7.2 g) 经过硅胶柱(石油醚-乙酸乙酯, 10∶1) 分离纯化, 得到4个组分, Fr.4.2.1~Fr.4.2.4。Fr.4.2.2 (696.8 mg) 先后经过3次硅胶柱(石油醚-丙酮, 5∶1; 二氯甲烷-乙酸乙酯, 30∶1; 氯仿-丙酮, 20∶1) 分离纯化, 得到化合物8 (33.0 mg) 和化合物9 (13.3 mg)。Fr.4.2.3 (927.4 mg) 先后经过2次硅胶柱色谱(石油醚-异丙醇, 15∶1; 二氯甲烷-丙酮, 50∶1) 分离纯化, 得到化合物10 (38.8 mg)、化合物11 (24.9 mg) 和化合物12 (3.3 mg)。Fr.4.4 (3.0 g) 经过硅胶柱色谱(石油醚-异丙醇, 20∶1) 分离, 得到3个组分, Fr.4.4.1~Fr.4.4.3。Fr.4.4.3 (1.2 g) 经过硅胶柱(石油醚-乙酸乙酯, 3∶1) 纯化, 得到化合物7 (308.3 mg)。
Fr.5 (84.0 g) 经过硅胶柱色谱(二氯甲烷-甲醇, 60∶1~0∶1) 分离, 得到4个组分, Fr.5.1~Fr.5.4。Fr.5.4 (14.0 g) 经过硅胶柱(石油醚-乙酸乙酯, 7∶1) 分离, 得到3个组分, Fr.5.4.1~Fr.5.4.3。Fr.5.4.3 (940.7 mg) 先后经过2次硅胶柱(氯仿-异丙醇, 35∶1; 石油醚-异丙醇, 10∶1) 分离纯化, 得到化合物13 (3.0 mg)。
Fr.6 (40.0 g) 经过硅胶柱(二氯甲烷-甲醇, 55∶1~0∶1) 层析, 得到3个组分, Fr.6.1~Fr.6.3。Fr.6.1 (17.5 g) 经过硅胶柱(石油醚-异丙醇, 15∶1) 纯化, 得到4个组分, Fr.6.1.1~Fr.6.1.4。Fr.6.1.1 (4.9 g) 先后经过硅胶柱(二氯甲烷-异丙醇, 40∶1)、Sephadex LH-20柱(甲醇) 及半制备HPLC (75%甲醇水) 纯化得到化合物15 (24.0 mg) 和化合物16 (3.0 mg)。
Fr.6.2 (4.3 g) 经过硅胶柱色谱(石油醚-异丙醇, 15∶1) 分离, 得到3个组分, Fr.6.2.1~Fr.6.2.3。Fr.6.2.1 (1.7 g) 经过硅胶柱(二氯甲烷-异丙醇, 40∶1) 和Sephadex LH-20柱(甲醇) 纯化分离得到化合物14 (15.4 mg) 和化合物17 (13.5 mg)。
2　结构鉴定
化合物1 白色无定形粉末, HR-ESI-MS (+): m/z 475.317 7 [M+Na]+ (计算值475.318 3, C30H44O3Na); 1H NMR (CDCl3, 600 MHz) 和13C NMR (CDCl3, 151 MHz) 见表1。
化合物2 无色油状物, HR-ESI-MS (+): m/z 477.334 7 [M+Na]+ (计算值477.333 9, C30H46O3Na); 1H NMR (CD3OD, 600 MHz) 和13C NMR (CD3OD, 151 MHz) 见表1。
3　抑制α-葡萄糖苷酶活性
采用α-葡萄糖苷酶诱导pNPG生成pNP的体外筛选模型[29], 对化合物1、3~17抑制α-葡萄糖苷酶活性进行了评价。实验分为四个组: 空白组(B)、对照组(C)、样品空白组(SB) 和样品组(S)。每组6个平行。以pNPG为底物, 阿卡波糖作为阳性对照, 将α-葡萄糖苷酶溶液(0.4 U·mL-1) 20 μL、磷酸盐缓冲溶液(0.1 mol·L-1, pH 6.8) 90 μL和不同浓度的样品溶液30 μL加入96孔板, 37 ℃孵育20 min, 再加入pNPG溶液(10 mmol·L-1) 40 μL, 37 ℃孵育20 min, 最后加入0.2 mol·L-1碳酸钠溶液70 μL终止反应, 在405 nm处测定样品吸光度(A)。空白和样品空白组中用等体积的磷酸盐缓冲液代替α-葡萄糖苷酶溶液, 空白和对照组中用等体积的磷酸盐缓冲溶液代替样品溶液, 根据不同浓度样品的抑制率可计算出IC50, 见式1。
$ 抑制率 =\frac{({A}_{\mathrm{C}}-{A}_{\mathrm{B}})-({A}_{\mathrm{S}}-{A}_{\mathrm{S}\mathrm{B}})}{({A}_{\mathrm{C}}-{A}_{\mathrm{B}})}\times 100\% $

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doi: 10.16438/j.0513-4870.2025-0087
  • 接收时间：2025-01-23
  • 首发时间：2026-09-20
  • 出版时间：2025-06-12
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  • 收稿日期：2025-01-23
  • 修回日期：2025-03-24
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    昆明理工大学生命科学与技术学院, 云南 昆明 650500

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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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