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Article(id=1198652610325607051, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198652605778985059, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2022-1191, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=null, receivedDate=1667750400000, receivedDateStr=2022-11-07, revisedDate=1669564800000, revisedDateStr=2022-11-28, acceptedDate=null, acceptedDateStr=null, onlineDate=1763710652189, onlineDateStr=2025-11-21, pubDate=1691769600000, pubDateStr=2023-08-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1763710652189, onlineIssueDateStr=2025-11-21, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1763710652189, creator=13701087609, updateTime=1763710652189, updator=13701087609, issue=Issue{id=1198652605778985059, tenantId=1146029695717560320, journalId=1189982191388893191, year='2023', volume='58', issue='8', pageStart='0', pageEnd='2540', issueExtLink='null', onlineDate='null', pubDate='1691769600000', pubDateStr='2023-08-12', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1763710651106, creator='13701087609', updateTime=1763710739504, updator='13701087609', preIssue=null, nextIssue=null, articleTotal=null, ext={EN=IssueExt(id=1198652976601596347, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198652605778985059, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1198652976601596348, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1198652605778985059, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null, downloadFileDto=null}, startPage=2442, endPage=2447, ext={EN=ArticleExt(id=1198652610866672275, articleId=1198652610325607051, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Pyridine pigments from functional Monascus rice, columnId=null, journalTitle=Acta Pharmaceutica Sinica, columnName=null, runingTitle=null, highlight=null, articleAbstract=

The trace chemical components in functional Monascus rice were studied to explore the potential bioactive substances. MCI column, Sephadex LH-20 gel, and preparative liquid chromatography were used to purified the ethyl acetate extract from functional Monascus rice. Two novel pyridine Monascus pigments were isolated and identified, named monascopyridine G (1) and monascopyridine H (2), respectively based on extensive mass spectrometry (MS), infrared radiation (IR), and nuclear magnetic resonance (NMR) analysis. The molecular docking experiments between compounds 1 and 2 and peroxisome proliferators-activated receptor-gamma (PPARγ) showed that they exhibited obvious binding force with the receptor protein. Besides, the biosynthetic pathways of the two compounds were proposed, which provide a valuable reference for the selective production of these potential bioactive substances.

, authors=null, authorsList=Bing-yu LIU, Xiao-ming ZHENG, An-an LIU, Fei XU, Qian WEI, You-cai HU, authorCompany=null, correspAuthors=You-cai HU, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2023 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=1198652614293418726, articleId=1198652610325607051, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=功能红曲米中的吡啶类色素化合物, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

对功能性红曲米中的微量化学成分进行研究, 以探索潜在的生物活性物质。运用MCI柱色谱、Sephadex LH-20凝胶柱色谱、制备液相色谱等多种色谱方法, 对其乙酸乙酯提取物部分进行分离, 应用质谱(mass spectrometry, MS)、红外(infrared radiation, IR)、核磁共振(nuclear magnetic resonance, NMR) 等波谱学方法对分离得到的天然产物进行鉴定。从中分离并鉴定了两个新颖的吡啶类红曲红色素成分, 分别为monascopyridine G (1) 和monascopyridine H (2)。通过CDOCKER分子对接实验探究其过氧化物酶体增殖物激活受体γ (peroxisome proliferators-activated receptor-gamma, PPARγ) 激动活性, 发现其与受体蛋白有较好的结合力。并进一步对该类化合物的生物合成途径进行了推测, 为选择性生产该类潜在活性物质提供参考。

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*胡友财, Tel: 86-10-50927869, E-mail:
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No. 1a 2b
δH mult (J in Hz) δC δH mult (J in Hz) δC
2 8.85 s 150.2 8.83 s 151.02
3 123.1 130.7
4 149.3 151.0
5 7.33 s 118.5 6.91 s 117.2
6 158.1 154.7
7 6.60 dd (15.6, 1.6) 130.2 6.47 dd (15.6, 1.3) 130.9
8 6.93 dd (15.6, 6.9) 134.0 6.73 dd (15.6, 7.0) 130.3
9 1.91 dd (6.9, 1.6) 18.3 1.84 d (7.0) 18.2
10 166.2 167.9
11 190.1 191.6
12 120.2 120.3
13 157.4 133.2
14 163.8 130.1
15 114.1 5.58 s 106.9
16 158.6 2.34 t (7.7) 26.7
17 2.78 t (7.5) 26.2 1.45 m 28.7
18 1.57 m 27.2 1.21 overlap 31.0
19 1.24 m 30.6 1.25 overlap 21.9
20 1.27 m 21.7 0.83 t (7.0) 13.9
21 0.85 t (7.0) 13.8 2.12 s 13.1
22 2.24 s 13.4
), ArticleFig(id=1198960119196254662, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1198652610325607051, language=CN, label=Table 1, caption=

Nuclear magnetic resonance (NMR) spectroscopic data of compounds 1 and 2 in DMSO-d6. a: 600 MHz for 1H-NMR and 150 MHz for 13C-NMR; b: 500 MHz for 1H-NMR and 125 MHz for 13C-NMR

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No. 1a 2b
δH mult (J in Hz) δC δH mult (J in Hz) δC
2 8.85 s 150.2 8.83 s 151.02
3 123.1 130.7
4 149.3 151.0
5 7.33 s 118.5 6.91 s 117.2
6 158.1 154.7
7 6.60 dd (15.6, 1.6) 130.2 6.47 dd (15.6, 1.3) 130.9
8 6.93 dd (15.6, 6.9) 134.0 6.73 dd (15.6, 7.0) 130.3
9 1.91 dd (6.9, 1.6) 18.3 1.84 d (7.0) 18.2
10 166.2 167.9
11 190.1 191.6
12 120.2 120.3
13 157.4 133.2
14 163.8 130.1
15 114.1 5.58 s 106.9
16 158.6 2.34 t (7.7) 26.7
17 2.78 t (7.5) 26.2 1.45 m 28.7
18 1.57 m 27.2 1.21 overlap 31.0
19 1.24 m 30.6 1.25 overlap 21.9
20 1.27 m 21.7 0.83 t (7.0) 13.9
21 0.85 t (7.0) 13.8 2.12 s 13.1
22 2.24 s 13.4
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Target Radius/Å Coordinate RMSD Scoring value
PPARγ 5.927 36.165 1, ‒10.379, 40.431 6 1.818 52 28.204 2
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Active pocket of peroxisome proliferators-activated receptor-gamma (PPARγ). RMSD: Root-mean-square deviation

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功能红曲米中的吡啶类色素化合物
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刘冰语 , 郑晓明 , 刘安安 , 徐飞 , 魏茜 , 胡友财 *
药学学报 | 研究论文 2023,58(8): 2442-2447
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药学学报 |研究论文 2023 , 58 (8) : 2442 -2447
功能红曲米中的吡啶类色素化合物
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刘冰语, 郑晓明, 刘安安, 徐飞, 魏茜, 胡友财*
作者信息
  • 中国医学科学院、北京协和医学院药物研究所, 天然药物活性物质与功能国家重点实验室, 北京 100050
通讯作者:
*胡友财, Tel: 86-10-50927869, E-mail:
Pyridine pigments from functional Monascus rice
Bing-yu LIU, Xiao-ming ZHENG, An-an LIU, Fei XU, Qian WEI, You-cai HU*
Affiliations
  • Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
出版时间: 2023-08-12 doi: 10.16438/j.0513-4870.2022-1191
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摘要
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对功能性红曲米中的微量化学成分进行研究, 以探索潜在的生物活性物质。运用MCI柱色谱、Sephadex LH-20凝胶柱色谱、制备液相色谱等多种色谱方法, 对其乙酸乙酯提取物部分进行分离, 应用质谱(mass spectrometry, MS)、红外(infrared radiation, IR)、核磁共振(nuclear magnetic resonance, NMR) 等波谱学方法对分离得到的天然产物进行鉴定。从中分离并鉴定了两个新颖的吡啶类红曲红色素成分, 分别为monascopyridine G (1) 和monascopyridine H (2)。通过CDOCKER分子对接实验探究其过氧化物酶体增殖物激活受体γ (peroxisome proliferators-activated receptor-gamma, PPARγ) 激动活性, 发现其与受体蛋白有较好的结合力。并进一步对该类化合物的生物合成途径进行了推测, 为选择性生产该类潜在活性物质提供参考。

红曲米  /  色素  /  分子对接  /  过氧化物酶体增殖物激活受体γ激动剂  /  生物合成

The trace chemical components in functional Monascus rice were studied to explore the potential bioactive substances. MCI column, Sephadex LH-20 gel, and preparative liquid chromatography were used to purified the ethyl acetate extract from functional Monascus rice. Two novel pyridine Monascus pigments were isolated and identified, named monascopyridine G (1) and monascopyridine H (2), respectively based on extensive mass spectrometry (MS), infrared radiation (IR), and nuclear magnetic resonance (NMR) analysis. The molecular docking experiments between compounds 1 and 2 and peroxisome proliferators-activated receptor-gamma (PPARγ) showed that they exhibited obvious binding force with the receptor protein. Besides, the biosynthetic pathways of the two compounds were proposed, which provide a valuable reference for the selective production of these potential bioactive substances.

Monascus rice  /  pigment  /  molecular docking  /  peroxisome proliferators-activated receptor-gamma agonist  /  biosynthesis
刘冰语, 郑晓明, 刘安安, 徐飞, 魏茜, 胡友财. 功能红曲米中的吡啶类色素化合物. 药学学报, 2023 , 58 (8) : 2442 -2447 . DOI: 10.16438/j.0513-4870.2022-1191
Bing-yu LIU, Xiao-ming ZHENG, An-an LIU, Fei XU, Qian WEI, You-cai HU. Pyridine pigments from functional Monascus rice[J]. Acta Pharmaceutica Sinica, 2023 , 58 (8) : 2442 -2447 . DOI: 10.16438/j.0513-4870.2022-1191
正文
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红曲发酵产物作为药食两用的中药在我国已有一千多年的使用历史, 能产生莫纳可林类(即他汀类)、红曲色素、甾醇类等多种代谢产物[1, 2], 其制品目前在美国和多个亚洲国家用作保健食品[3]。许多研究表明红曲的代谢产物能产生很高的商业价值, 如食用色素、降脂药物和抗生素等, 为确保市场红曲药材的质量可控, 有研究探索通过次生代谢物指纹图谱法区分不同用途的红曲[4]。红曲色素作为一种天然食用色素, 在世界食品工业中得到了广泛应用[5]。此外, 红曲色素还具有一系列生物活性, 如抗突变、抗癌、抗菌、潜在的抗肥胖等[6-8]。随着人民生活水平提高、生活模式的变化, 无论是发达国家或发展中国家, 糖尿病的发病率都在逐年增加; 而其中95%以上为非胰岛素依赖型糖尿病, 即2型糖尿病, 继肿瘤、心血管疾病之后其死亡率已上升至第三位[9, 10]。因此, 防治糖尿病尤其是2型糖尿病是一个迫在眉睫的重大需求。自20世纪末以来, 以治疗2型糖尿病为目的的各种过氧化物酶体增殖物激活受体γ (peroxisome proliferators-activated receptor-gamma, PPARγ) 激动剂不断被研究开发出来[11-14], 且有研究表明从红曲发酵产物中分离得到的吡啶类色素monasnicotinates A~D具有增加PPARγ活性的作用[15], 为红曲发酵提取物可用于预防或治疗与胰岛素抵抗相关的疾病提供了依据。本课题组前期从功能红曲米中发现了13个洛伐他汀类化合物及4个酚酸类化合物[16, 17]。本研究在前期基础上, 分离得到两个结构新颖的具有吡啶母核的红曲红色素类成分monascopyridine G (1) 和monascopyridine H (2) (图 1), 结合吡啶类生物碱具有增加PPARγ活性作用的报道[15], 本研究对这两个化合物与PPARγ的分子对接进行了模拟研究, 通过分析关键氨基酸, 提示化合物1和2与受体蛋白有较好的结合力, 为潜在的PPARγ激动剂。
结果与讨论
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1 结构鉴定
化合物1, 红色油状物, HR-ESI-MS给出准分子离子峰m/z 386.159 58 [M+H]+ (计算值C21H24O6N, 386.159 81), 提示其分子式为C21H23O6N, 不饱和度为11。1H-NMR (600 MHz, DMSO-d6) 显示有3个甲基信号δH 0.85 (3H, t, J = 7.0 Hz, 21-CH3)、1.91 (3H, dd, J = 7.0, 1.7 Hz, 9-CH3)、2.24 (3H, s, 22-CH3); 4个烯氢信号δH 6.60 (1H, dd, J = 15.6, 1.6 Hz, H-7)、6.93 (1H, dd, J = 15.6, 6.9 Hz, H-8)、7.33 (1H, s, H-5)、8.85 (H, s, H-2) (表 1)。13C-NMR (150 MHz, DMSO-d6) 显示有21个碳信号, 其中有3个甲基碳信号δC 13.4 (C-22)、13.8 (C-21) 和18.3 (C-9)。同时可看到3个羰基信号, 分别为酯羰基δC 163.8 (C-14)、羧基δC 166.2 (C-10) 和α, β不饱和酮羰基δC 190.1 (C-11), 11个烯碳信号δC 150.2 (C-2)、123.1 (C-3)、149.3 (C-4)、118.5 (C-5)、158.1 (C-6)、130.2 (C-7)、134.0 (C-8)、120.2 (C-12)、157.4 (C-13)、114.1 (C-15)、158.6 (C-16)。此外, 结合碳信号δC 120.2 (C-12)、157.4 (C-13)、163.8 (C-14)、114.1 (C-15) 和13.4 (C-22) 及文献[18]报道的化合物malleilactone中五元内酯环片段的核磁数据, 推断化合物中可能也存在甲基取代的五元内酯环片段。而综合碳信号δC 150.2 (C-2)、123.1 (C-3)、149.3 (C-4)、118.5 (C-5)、158.1 (C-6) 及文献[19, 20]报道的化合物monasnicotinates A~D及monascopydines E、F中含有的吡啶结构片段的核磁数据, 推断化合物1中可能存在一个类似的吡啶片段。1H-1H COSY谱中, δH 1.57 (2H, m, H-18) 与2.78 (2H, t, J = 7.5 Hz, H-17)、1.24 (2H, m, H-19) 相关, δH1.27 (2H, m, H-20) 与1.24 (2H, m, H-19)、1.24、0.87 (3H, t, J = 7.0 Hz, H-21) 相关, 确定-(CH2)4-CH3的结构片段; δH 6.93 (1H, dd, J = 15.6, 6.9 Hz, H-8) 与6.60 (1H, dd, J = 15.6, 1.6 Hz, H-7)、1.91 (3H, dd, J = 6.9, 1.6 Hz, H-9) 相关, 确定-CH=CH-CH3的结构片段(图 2)。
HMBC谱中H-22 (δH 2.24) 与157.4 (C-13)、120.2 (C-12) 之间存在相关, 确定了甲基的连接位置; 结合碳谱数据进一步确证了五元内酯环的存在。通过H-21 (δH 0.85) 与21.7 (C-20)、30.6 (C-19) 之间的相关, H-18 (δH 1.57) 与158.6 (C-16)、26.22 (C-17)、30.6 (C-19) 之间的相关, H-17 (δH 2.78) 与114.1 (C-15) 之间的相关可确定己基片段的连接位置。通过H-2 (δH 8.85) 与123.1 (C-3)、149.3 (C-4)、158.1 (C-6)、166.2 (C-10) 之间的相关可确定羧基的连接位置, 并进一步确证了吡啶片段的存在; 通过H-9 (δH 1.91) 与130.2 (C-7)、134.0 (C-8) 之间的相关, H-7 (δH 6.60) 与158.1 (C-6) 之间的相关和H-5 (δH 7.33) 与130.2 (C-7) 之间的相关可确定丙烯基的连接位置。通过H-22 (δH 2.24)、H-5 (δH 7.33)、H-2 (δH 8.85) 与190.1 (C-11) 之间的相关可确定五元内酯环与吡啶片段是通过α, β不饱和酮基连接, 从而最终确定了化合物1的结构(图 1)。首次发现五元内酯环片段通过α, β不饱和酮基与吡啶片段连接的吡啶色素类化合物, 经SciFinder数据库查询确定化合物1为新化合物, 命名为monascopyridine G。
化合物2, 红色油状物, HR-ESI-MS给出准分子离子峰m/z 341.185 76 [M+H]+ (计算值C20H25O3N2, 341.185 97), 提示化合物2分子式为C20H24O3N2, 不饱和度为10。1H-NMR和3C-NMR数据显示, 化合物2与化合物1有相同的丙烯基及羧基取代的吡啶片段(表 1)。结合碳信号δC 120.3 (C-12)、133.2 (C-13)、130.1 (C-14)、106.9 (C-15)、13.1 (C-21) 推断化合物2中可能存在一个甲基取代的吡咯环片段。通过HMBC谱中H-15 (δH 5.58)、NH (δH 10.93) 与120.3 (C-12)、133.2 (C-13)、130.1 (C-14) 之间的相关, 以及H-21 (δH 2.12) 与120.3 (C-12)、133.2 (C-13) 之间的相关进一步确定了甲基取代的吡咯环片段的存在。通过H-20 (δH 0.83) 与21.9 (C-19)、31.0 (C-18) 之间的HMBC相关, H-18 (δH 1.21) 与26.7 (C-16) 之间的相关, H-16 (δH 2.34) 与130.1 (C-14)、106.9 (C-15)、120.3 (C-12) 之间的相关确定了戊基片段的连接位点。通过H-21 (δH 2.12)、H-5 (δH 6.91)、H-2 (δH 8.83) 与191.6 (C-11) 之间的相关可确定甲基取代的吡咯环片段与吡啶片段是通过α, β不饱和酮基连接, 从而最终确定了化合物2的结构(图 1)。经SciFinder数据库查询确定化合物2为新化合物, 命名为monascopyridine H。
2 化合物1和2与PPARγ的分子对接研究
利用PPARγ的原配体(halofenic acid) 与晶体结构通过CDOCKER方法进行对接并定义活性口袋, 其活性口袋信息及计算结果见表 2。Gee等[21]的研究中发现氨基酸CYS285、ARG288和ILE341是PPARγ与激动剂相互作用的关键氨基酸。故以与氨基酸CYS285、ARG288和ILE341形成相互作用建立筛选标准, 将具有类药性质的2个潜在化合物1和2对接到活性口袋中, 打分值分别是24.59及35.80。分析两个化合物与PPARγ相互作用, 发现化合物1羧基氢键特征的位置与LEU340形成氢键相互作用, 形成芳环特征的苯环与ILE341、ARG288形成疏水相互作用, 疏水特征处的五元内酯环与CYS285、LEU330、ARG288形成疏水相互作用。化合物1与受体的相互作用见图 3A。化合物2羧基氢键特征的位置与LEU340形成氢键相互作用, 形成芳环特征的苯环与ILE341、ARG288、GLY284形成疏水相互作用, 疏水特征处的吡咯环与CYS285、LEU330、ARG288形成疏水相互作用。化合物2与受体的相互作用见图 3B。化合物1和2均与关键氨基酸CYS285、ARG288和ILE341形成疏水相互作用, 提示它们可能是PPARγ激动剂, 具有潜在抗糖尿病活性。
3 生物合成途径推测
红曲色素主要由红、橙、黄3类色素组成, 其中水溶性色素红色红曲色素受到越来越多的关注。多数红色红曲色素是氨基酸衍生物, 包括含有二氢吡啶片段的红斑胺素(rubropunctamine)、monascorubramine类成分及含有吡啶结构片段的monascopyridine类成分等。Chen等[22]对红曲代谢产物azaphilone类色素成分进行了生物合成途径研究, 表明红曲色素通常以乙酰辅酶A为起始单元, 与丙二酰辅酶A经克莱森缩合反应发生5次链延伸, 再经脱水、还原、氧化等一系列反应过程得到具有二氢吡啶骨架的化合物rubropunctamine。在此基础上, 本研究根据具有吡啶骨架的红曲红色素类成分化合物1和2的结构特点, 推测其生物合成途径(图 4) 是以化合物rubropunctamine[22]为关键中间体, 其经羟化、氧化开环等生成目标分子1。化合物1再经水解、脱羧、脱水等一系列反应生成中间体iii, 最后经氨基取代将五元内酯环转化为吡咯环生成目标分子2。
4 结论
本研究从功能红曲米中分离并鉴定了两个新颖的吡啶类红曲色素化合物1和2, 分子对接实验提示其为潜在的PPARγ激动剂, 生物合成途径分析为该类潜在活性物质的化学酶法合成提供了参考。
实验部分
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JASCO V-650紫外-可见光谱仪(Jasco日本分光公司); Nicolet 6700型傅里叶变换红外光谱仪(赛默飞世尔公司); Bruker AV-Ⅲ-500、Bruker AV-Ⅲ-600 HD型核磁共振光谱仪(德国布鲁克公司); Agilent Technologies 6520 Accurate Mass Q-TOF LC/MS型质谱仪(美国安捷伦公司); SSI半制备高效液相色谱仪(DAD检测器, 美国科学系统公司); YMC-Pack ODS-A半制备色谱柱(10 mm × 250 mm, 5 μm, 日本YMC公司); Waters ACQUITY H-Class-QDA超高效液相质谱联用仪、ACQUITY UPLC BEH色谱柱(2.1 mm × 50 mm, 1.7 μm) (美国沃特世公司); TELEDYNE ISCO CombiFlash Rf +型中压液相色谱仪[环球(香港) 科技有限公司]; 羟丙基葡聚糖Sephadex LH-20 (GE Healthcare Bio-Sciences AB公司); MCI gel CHP 20P /P120 (日本三菱化学株式会社); 硅胶薄层色谱GF254 (青岛海洋化工厂)。红曲米为市售的功能红曲(浙江三禾生物工程股份有限公司, 批号: SH2015051502)。
1 提取分离
取红曲米粉末5 kg, 用乙酸乙酯(15 L) 过夜浸泡, 而后放于超声波清洗机中超声提取2 h, 重复上述步骤3次, 提取液减压蒸馏浓缩得到浸膏总量为105.9 g。粗膏溶于适量甲醇中分散, 加入石油醚进行萃取, 甲醇溶解部分和石油醚溶解部分分别进行减压浓缩, 得到甲醇萃取物(68.5 g) 和石油醚萃取物(34.7 g)。甲醇部分(68.5 g) 样品经MCI (柱体积为1.8 L) 柱层析, 用20%-50%-90%-100%甲醇体系梯度洗脱, 每个梯度4个柱体积, 最后用丙酮将色谱柱残留部分冲洗干净, 全部接收完毕并使用旋转蒸发仪将其旋干, 得到Fr. A~E共5个组分, 组分Fr. B (4.94 g) 经中低压制备液相色谱(甲醇-水梯度洗脱, 20%~75%) 得到8个组分Fr.B1~B8, 组分Fr. B6 (0.99 g) 经Sephadex LH-20凝胶柱色谱(CH3OH∶H2O, 1∶1) 和半制备高效液相色谱(乙腈-水, 56∶44, 0.1% TFA, v/v) 分离纯化, 得到化合物monascopyridine G (tR = 34.0 min, 0.7 mg); 组分Fr. B7 (1.27 g) 经Sephadex LH-20凝胶柱色谱(CH3OH∶H2O, 1∶1) 得到7个馏分Fr.B7a~g, 其中Fr.B7e (34.9 mg) 再次经Sephadex LH-20凝胶柱色谱, 以甲醇作为流动相洗脱得到化合物monascopyridine H (0.9 mg)。
2 结构鉴定
化合物1: 红色油状物, UV (MeOH) λmax (logε): 202.6, 257.2, 294.8 nm; IR (microscope) vmax 3 381, 2 921, 2 854, 1 655, 1 388 cm-1; HR-ESI-MS m/z 386.159 58 [M+H]+ (计算值C21H24O6N, 386.159 81); 1H-NMR (DMSO-d6, 600 MHz) 数据和13C-NMR (DMSO-d6, 150 MHz) 数据见表 1。
化合物2: 红色油状物, UV (MeOH) λmax (logε): 211.8, 276.3, 302.4 nm; IR (microscope) vmax 2 955, 2 928, 2 854, 1 611, 1 582, 1 393 cm-1; HR-ESI-MS m/z 341.185 76 [M+H]+ (计算值C20H25O3N2, 341.185 97); 1H-NMR (DMSO-d6, 500 MHz) 和13C NMR (DMSO-d6, 125 MHz) 数据见表 1。
3 化合物1和2与PPARγ的分子对接研究
从PDB数据库中下载PPARγ靶点的蛋白三维结构, 选择PDB代码为4PUV[23]的蛋白晶体用于分子对接研究。对蛋白晶体结构进行删除多余蛋白质构象、删去水分子、补全不完整残基、加氢及分配相关电荷等处理, 处理后的蛋白用于分子对接研究。
基于晶体结构中复合的原配体定义活性口袋, 随后将原配体取出, 采用CDOCKER方法将原配体重新对接到定义的活性口袋中。计算初始配体分子构象和对接后分子构象的均方根偏差(root-mean-square deviation, RMSD), 若RMSD ≤ 2.0, 认为可重现初始配体分子与受体的结合模式, 说明所选择的对接方法及参数设置具有合理性[23]。将化合物1和2对接到设定的活性口袋中, 与对接后原配体打分值进行比较且与原配体-受体相互作用模式相似的作为潜在激动剂[24]。
作者贡献: 刘冰语和徐飞主要负责化合物分离纯化鉴定工作; 郑晓明负责分子对接模拟工作; 刘安安、魏茜负责文献调研、整理及文章修改; 胡友财为该文章的主要负责人, 负责文章的选题、思路和框架的提出, 全程指导实验设计、结构解析和论文撰写。
利益冲突: 文中没有任何利益冲突。
基金
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  • 国家杰出青年科学基金资助项目(82225042)
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2023年第58卷第8期
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doi: 10.16438/j.0513-4870.2022-1191
  • 接收时间：2022-11-07
  • 首发时间：2025-11-21
  • 出版时间：2023-08-12
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  • 收稿日期：2022-11-07
  • 修回日期：2022-11-28
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国家杰出青年科学基金资助项目(82225042)
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    中国医学科学院、北京协和医学院药物研究所, 天然药物活性物质与功能国家重点实验室, 北京 100050

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2种不同金属材料的力学参数
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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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