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Article(id=1200394155030598255, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1200394147019477416, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2023-1424, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1703001600000, receivedDateStr=2023-12-20, revisedDate=1709136000000, revisedDateStr=2024-02-29, acceptedDate=null, acceptedDateStr=null, onlineDate=1764125868804, onlineDateStr=2025-11-26, pubDate=1720713600000, pubDateStr=2024-07-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1764125868804, onlineIssueDateStr=2025-11-26, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1764125868804, creator=13701087609, updateTime=1764125868804, updator=13701087609, issue=Issue{id=1200394147019477416, tenantId=1146029695717560320, journalId=1189982191388893191, year='2024', volume='59', issue='7', pageStart='1897', pageEnd='2182', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1764125866894, creator=13701087609, updateTime=1764225115484, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1200810425920115296, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1200394147019477416, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1200810425920115297, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1200394147019477416, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=2069, endPage=2076, ext={EN=ArticleExt(id=1200394156225974922, articleId=1200394155030598255, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Studies on the chemical composition of Ferula feruloides, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Eleven compounds were isolated and purified from the ethyl acetate part of 80% ethanol extract of Ferula feruloides root by a combination of normal-phase silica gel column chromatography, Sephadex LH-20 dextran gel column chromatography and semi-preparative liquid chromatography and then modern wave spectrometry methods (NMR, MS, UV, IR) were used to identify the structures of the compounds, which were identified as baigene D (1), baigene E (2), baigene F (3), β-kirialovin (4), α-kirialovin (5), falcarindiol (6), ammoresinol (7), dshamirone (8), 2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-3-[4-methyl-5-(4-methy1-2-furyl)-3(E)-pentenyl]-furo[3, 2-c]coumarin (9), 2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-2-[4, 8-dimethyl-3(E), 7-nonadi-enyl]-furo[3, 2-c]coumarin (10), and baigene C (11). Compounds 1-3 are new coumarin analogues, and compounds 4-6 are firstly isolated from F. feruloides. The anti-proliferative activity of compounds 5, 7-11 against human gastric cancer (MKN-45) cells was evaluated using MTT assay, which showed that compounds 7-11 exhibited strong inhibitory activity, and compound 5 exhibited weak inhibitory activity.

, correspAuthors=Yan HU, Xin-zhou YANG, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2024 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, authorCompany=null, fund=null, authors=null, authorsList=Ying-he BI, Ke-jian PANG, Hui-zi LI, Yerlan BAHETJAN, Muguli MUHAXI, Yan HU, Xin-zhou YANG), CN=ArticleExt(id=1200394157836587772, articleId=1200394155030598255, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=多伞阿魏化学成分研究, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

综合应用正相硅胶柱层析、Sephadex LH-20葡聚糖凝胶柱色谱以及半制备型液相色谱等技术, 对多伞阿魏[Ferula feruloides (Steudel) Korovin] 根80%乙醇提取物的乙酸乙酯部位进行分离纯化, 得到11个化合物, 再运用现代波谱学方法 (NMR、MS、UV、IR) 鉴定化合物的结构, 分别鉴定为baigene D (1)、baigene E (2)、baigene F (3)、β-kirialovin (4)、α-kirialovin (5)、falcarindiol (6)、ammoresinol (7)、dshamirone (8)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-3-[4-methyl-5-(4-methy1-2-furyl)-3(E)-pentenyl]-furo[3, 2-c]coumarin (9)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-2-[4, 8-dimethyl-3(E), 7-nonadi-enyl]-furo[3, 2-c]coumarin (10) 和baigene C (11)。其中化合物1~3为新的香豆素类化合物, 化合物4~6为首次从多伞阿魏中分离得到。采用MTT试验对化合物5、7~11的抗人胃癌(MKN-45) 细胞增殖活性进行评价, 结果表明, 化合物7~11均表现出较强的抑制活性, 化合物5表现出较弱的抑制活性。

, correspAuthors=胡燕, 杨新洲, authorNote=null, correspAuthorsNote=
*胡燕, Tel: 86-27-67841196, E-mail: ;
杨新洲, E-mail:
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Traditional use and modern research review of Ferula in China [J]. Mod Chin Med (中国现代中药), 2013, 15: 620-626., articleTitle=null, refAbstract=null), Reference(id=1201106973484867944, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[2], rfOrder=1, authorNames=null, journalName=null, refType=null, unstructuredReference=Guo TT, Zhou YP, Dang W, et al. "Preexistence" and "present life" of traditional Chinese medicine Ferulae Resina [J]. Chin Tradit Herb Drugs (中草药), 2021, 52: 5401-5413., articleTitle=null, refAbstract=null), Reference(id=1201106973581336939, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[3], rfOrder=2, authorNames=null, journalName=null, refType=null, unstructuredReference=Li GQ, Hua JX. A comparison study on pollen morphology between Ferula and Heracleum of Umbelliferae [J]. Chin Agric Sci Bull (中国农学通报), 2006, 22: 114-118., articleTitle=null, refAbstract=null), Reference(id=1201106973665223023, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[4], rfOrder=3, authorNames=null, journalName=null, refType=null, unstructuredReference=Liu T, Wang S, Xu L, et al. Sesquiterpenoids with anti-MDR Staphylococcus aureus activities from Ferula ferulioides [J]. Chem Biodivers, 2015, 12: 599-614., articleTitle=null, refAbstract=null), Reference(id=1201106973719748980, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[5], rfOrder=4, authorNames=null, journalName=null, refType=null, unstructuredReference=Hu Y, Li XD, Li GY, et al. Two novel sesquiterpenoids from the roots of Ferula feruloides (Steud.) Korov [J]. Helv Chim Acta, 2010, 93: 1019-1024., articleTitle=null, refAbstract=null), Reference(id=1201106973795246454, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[6], rfOrder=5, authorNames=null, journalName=null, refType=null, unstructuredReference=Sheng P, Wang S, Miao LJ, et al. Correlation between volatile oils extracted from root of Ferula ferulaeoide by different methods and anti-gastric cancer activity [J]. Chin Tradit Pat Med (中成药), 2013, 35: 7., articleTitle=null, refAbstract=null), Reference(id=1201106973921075576, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[7], rfOrder=6, authorNames=null, journalName=null, refType=null, unstructuredReference=KoJima K, Isaka K, Ondognii P, et al. Sesquiterpenoid derivatives from Ferula feruloides. Ⅳ [J]. Chem Pharm Bull (Tokyo), 2000, 48: 353-356., articleTitle=null, refAbstract=null), Reference(id=1201106974000767354, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[8], rfOrder=7, authorNames=null, journalName=null, refType=null, unstructuredReference=Bukreeva TV, Shavarda AL, Pimenov MG. On the structure of dihydrofurocoumarins of α- and β-kirialovins in roots of Ferula kirialovii M. Pimen [J]. Rastit Resursy, 1993, 29: 45-51., articleTitle=null, refAbstract=null), Reference(id=1201106974072070525, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[9], rfOrder=8, authorNames=null, journalName=null, refType=null, unstructuredReference=Meot-Duros L, Stéphane C, Hélène T, et al. New antibacterial and cytotoxic activities of falcarindiol isolated in Crithmum maritimum L. leaf extract [J]. Food Chem Toxicol, 2010, 48: 553-557., articleTitle=null, refAbstract=null), Reference(id=1201106974151762304, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[10], rfOrder=9, authorNames=null, journalName=null, refType=null, unstructuredReference=Adhami H, Lutz J, Kählig H, et al. Compounds from gum ammoniacum with acetylcholinesterase inhibitory activity [J]. Sci Pharm, 2013, 81: 793-805., articleTitle=null, refAbstract=null), Reference(id=1201106974227259779, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[11], rfOrder=10, authorNames=null, journalName=null, refType=null, unstructuredReference=Iqbal Choudharya M, Baiga I, Nur-e-Alama M, et al. New-glucosidase inhibitors from the Mongolian medicinal plant Ferula mongolica [J]. Helv Chim Acta, 2001, 84: 2409-2416., articleTitle=null, refAbstract=null), Reference(id=1201106974311145862, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1200394155030598255, doi=null, pmid=null, pmcid=null, year=null, volume=null, issue=null, pageStart=null, pageEnd=null, url=null, language=null, rfNumber=[12], rfOrder=11, authorNames=null, journalName=null, refType=null, unstructuredReference=Isaka K, Nagatsu A, Ondognii P, et al. Sesquiterpenoid derivatives from Ferula feruloides. V [J]. 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No.123
24.67 (q, J = 6.8 Hz)
33.24 (q, J = 7.0 Hz)3.17 (q, J = 7.0 Hz)
3a
4
5a
66.74 (d, J = 1.8 Hz)6.74 (d, J = 2.3 Hz)6.74 (d, J = 2.3 Hz)
7
86.80 (dd, J = 8.6, 1.8 Hz)6.80 (dd, J = 8.6, 2.3 Hz)6.81 (dd, J = 8.7, 2.3 Hz)
97.53 (d, J = 8.6 Hz)7.50 (d, J = 8.6 Hz)7.52 (d, J = 8.7 Hz)
9a
9b
1′1.67 (t, J = 8.1 Hz)1.81 (t, J = 7.6 Hz)1.88 (ddd, J = 14.0, 10.7, 5.5 Hz)
1.74 (ddd, J = 14.0, 10.7, 5.5 Hz)
2′2.03 (m), 1.92 (m)2.14 (t, J = 7.6 Hz)2.24 (m)
3′5.11 (t, J = 7.3 Hz)5.14 (tq, J = 7.6, 1.4 Hz)5.22 (tq, J = 7.6, 1.4 Hz)
4′
5′3.07 (d, J = 15.6 Hz)
3.12 (d, J = 15.6 Hz)		2.14 (t, J = 7.6 Hz)2.23 (t, J = 7.6 Hz)
6′2.53 (t, J = 7.6 Hz)2.61 (t, J = 7.6 Hz)
7′5.81 (s)
8′2.62 (p, J = 7.0 Hz)2.66 (p, J = 7.0 Hz)
9′7.04 (s)1.04 (d, J = 7.0 Hz)1.06 (d, J = 7.0 Hz)
2Me1.55 (d, J = 6.8 Hz)1.46 (s)1.50 (s)
3Me1.41 (s)1.27 (d, J = 7.0 Hz)1.25 (d, J = 7.0 Hz)
4′Me1.41 (s)1.56 (d, J = 1.4 Hz)1.65 (d, J = 1.4 Hz)
8′Me1.93 (d, J = 1.5 Hz)1.04 (d, J = 7.0 Hz)1.06 (d, J = 7.0 Hz)
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1H NMR data of compounds 1-3 (600 MHz, CD3OD)

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No.123
24.67 (q, J = 6.8 Hz)
33.24 (q, J = 7.0 Hz)3.17 (q, J = 7.0 Hz)
3a
4
5a
66.74 (d, J = 1.8 Hz)6.74 (d, J = 2.3 Hz)6.74 (d, J = 2.3 Hz)
7
86.80 (dd, J = 8.6, 1.8 Hz)6.80 (dd, J = 8.6, 2.3 Hz)6.81 (dd, J = 8.7, 2.3 Hz)
97.53 (d, J = 8.6 Hz)7.50 (d, J = 8.6 Hz)7.52 (d, J = 8.7 Hz)
9a
9b
1′1.67 (t, J = 8.1 Hz)1.81 (t, J = 7.6 Hz)1.88 (ddd, J = 14.0, 10.7, 5.5 Hz)
1.74 (ddd, J = 14.0, 10.7, 5.5 Hz)
2′2.03 (m), 1.92 (m)2.14 (t, J = 7.6 Hz)2.24 (m)
3′5.11 (t, J = 7.3 Hz)5.14 (tq, J = 7.6, 1.4 Hz)5.22 (tq, J = 7.6, 1.4 Hz)
4′
5′3.07 (d, J = 15.6 Hz)
3.12 (d, J = 15.6 Hz)		2.14 (t, J = 7.6 Hz)2.23 (t, J = 7.6 Hz)
6′2.53 (t, J = 7.6 Hz)2.61 (t, J = 7.6 Hz)
7′5.81 (s)
8′2.62 (p, J = 7.0 Hz)2.66 (p, J = 7.0 Hz)
9′7.04 (s)1.04 (d, J = 7.0 Hz)1.06 (d, J = 7.0 Hz)
2Me1.55 (d, J = 6.8 Hz)1.46 (s)1.50 (s)
3Me1.41 (s)1.27 (d, J = 7.0 Hz)1.25 (d, J = 7.0 Hz)
4′Me1.41 (s)1.56 (d, J = 1.4 Hz)1.65 (d, J = 1.4 Hz)
8′Me1.93 (d, J = 1.5 Hz)1.04 (d, J = 7.0 Hz)1.06 (d, J = 7.0 Hz)
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No.123
294.598.397.8
347.843.045.3
3a106.6103.9103.5
4163.2163.6163.7
5a158.3158.2158.2
6103.4103.5103.5
7163.7163.7163.6
8114.4114.4114.4
9125.2125.2125.1
9a106.1106.1106.3
9b168.6167.4167.2
1′35.742.636.1
2′25.123.223.8
3′127.5125.2125.2
4′133.1135.7135.8
5′39.234.534.6
6′155.439.940.0
7′109.7217.0217.0
8′121.741.841.8
9′138.818.618.6
2Me14.120.925.5
3Me24.014.413.8
4′Me15.916.016.0
8′Me9.818.618.6
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13C NMR date of compounds 1-3 (150 MHz, CD3OD)

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No.123
294.598.397.8
347.843.045.3
3a106.6103.9103.5
4163.2163.6163.7
5a158.3158.2158.2
6103.4103.5103.5
7163.7163.7163.6
8114.4114.4114.4
9125.2125.2125.1
9a106.1106.1106.3
9b168.6167.4167.2
1′35.742.636.1
2′25.123.223.8
3′127.5125.2125.2
4′133.1135.7135.8
5′39.234.534.6
6′155.439.940.0
7′109.7217.0217.0
8′121.741.841.8
9′138.818.618.6
2Me14.120.925.5
3Me24.014.413.8
4′Me15.916.016.0
8′Me9.818.618.6
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多伞阿魏化学成分研究
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毕英赫 1 , 庞克坚 2 , 李卉子 1 , 叶尔兰•巴合特江 1 , 木古丽•木哈西 2 , 胡燕 1, * , 杨新洲 1, *
药学学报 | 研究论文 2024,59(7): 2069-2076
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药学学报 | 研究论文 2024, 59(7): 2069-2076
多伞阿魏化学成分研究
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毕英赫1, 庞克坚2, 李卉子1, 叶尔兰•巴合特江1, 木古丽•木哈西2, 胡燕1, * , 杨新洲1, *
作者信息
  • 1.中南民族大学药学院, 湖北 武汉 430074
  • 2.伊犁师范大学, 新疆 伊宁 835000

通讯作者:

*胡燕, Tel: 86-27-67841196, E-mail: ;
杨新洲, E-mail:
Studies on the chemical composition of Ferula feruloides
Ying-he BI1, Ke-jian PANG2, Hui-zi LI1, Yerlan BAHETJAN1, Muguli MUHAXI2, Yan HU1, * , Xin-zhou YANG1, *
Affiliations
  • 1. College of Pharmacy, South-Central Minzu University, Wuhan 430074, China
  • 2. Yili Normal University, Yining 835000, China
出版时间: 2024-07-12 doi: 10.16438/j.0513-4870.2023-1424
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摘要
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综合应用正相硅胶柱层析、Sephadex LH-20葡聚糖凝胶柱色谱以及半制备型液相色谱等技术, 对多伞阿魏[Ferula feruloides (Steudel) Korovin] 根80%乙醇提取物的乙酸乙酯部位进行分离纯化, 得到11个化合物, 再运用现代波谱学方法 (NMR、MS、UV、IR) 鉴定化合物的结构, 分别鉴定为baigene D (1)、baigene E (2)、baigene F (3)、β-kirialovin (4)、α-kirialovin (5)、falcarindiol (6)、ammoresinol (7)、dshamirone (8)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-3-[4-methyl-5-(4-methy1-2-furyl)-3(E)-pentenyl]-furo[3, 2-c]coumarin (9)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-2-[4, 8-dimethyl-3(E), 7-nonadi-enyl]-furo[3, 2-c]coumarin (10) 和baigene C (11)。其中化合物1~3为新的香豆素类化合物, 化合物4~6为首次从多伞阿魏中分离得到。采用MTT试验对化合物5、7~11的抗人胃癌(MKN-45) 细胞增殖活性进行评价, 结果表明, 化合物7~11均表现出较强的抑制活性, 化合物5表现出较弱的抑制活性。

阿魏属  /  多伞阿魏  /  化学成分  /  香豆素  /  倍半萜

Eleven compounds were isolated and purified from the ethyl acetate part of 80% ethanol extract of Ferula feruloides root by a combination of normal-phase silica gel column chromatography, Sephadex LH-20 dextran gel column chromatography and semi-preparative liquid chromatography and then modern wave spectrometry methods (NMR, MS, UV, IR) were used to identify the structures of the compounds, which were identified as baigene D (1), baigene E (2), baigene F (3), β-kirialovin (4), α-kirialovin (5), falcarindiol (6), ammoresinol (7), dshamirone (8), 2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-3-[4-methyl-5-(4-methy1-2-furyl)-3(E)-pentenyl]-furo[3, 2-c]coumarin (9), 2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-2-[4, 8-dimethyl-3(E), 7-nonadi-enyl]-furo[3, 2-c]coumarin (10), and baigene C (11). Compounds 1-3 are new coumarin analogues, and compounds 4-6 are firstly isolated from F. feruloides. The anti-proliferative activity of compounds 5, 7-11 against human gastric cancer (MKN-45) cells was evaluated using MTT assay, which showed that compounds 7-11 exhibited strong inhibitory activity, and compound 5 exhibited weak inhibitory activity.

Ferula L.  /  Ferula feruloides  /  chemical composition  /  coumarin  /  sesquiterpene
毕英赫, 庞克坚, 李卉子, 叶尔兰•巴合特江, 木古丽•木哈西, 胡燕, 杨新洲. 多伞阿魏化学成分研究. 药学学报, 2024 , 59 (7) : 2069 -2076 . DOI: 10.16438/j.0513-4870.2023-1424
Ying-he BI, Ke-jian PANG, Hui-zi LI, Yerlan BAHETJAN, Muguli MUHAXI, Yan HU, Xin-zhou YANG. Studies on the chemical composition of Ferula feruloides[J]. Acta Pharmaceutica Sinica, 2024 , 59 (7) : 2069 -2076 . DOI: 10.16438/j.0513-4870.2023-1424
正文
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阿魏属Ferula L.植物是隶属于伞形科Apiaceae的多年生草本, 具特殊臭味。阿魏属植物全球约有150种, 国外主要分布在印度、巴基斯坦、阿富汗、伊朗、非洲北部和欧洲南部等地[1]。我国有26种, 主要分布于新疆。阿魏属植物的药用价值历代本草均有记载, 始载于《新修本草》[2], 在国外收录于阿育吠陀药典和尤纳尼药典中, 常用于消积杀虫、解毒祛痰、消肿止痛等[3]。因阿魏对治疗风湿关节炎、胃病有独特疗效, 在民间作为药用植物被维、蒙、哈等少数民族广泛使用。多伞阿魏作为新疆阿魏的替代品沿用有十余年时间, 但化学成分研究不够深入, 目前研究表明, 多伞阿魏的根部以倍半萜-香豆素杂合化合物、倍半萜-色酮杂合化合物为主, 具有抗菌[4]、抗炎[5]、抗肿瘤和杀虫[6]等作用。对此, 有必要对多伞阿魏的化学成分进行系统研究, 以期挖掘多伞阿魏和新疆阿魏在化学成分方面的差异, 为新疆的阿魏资源更合理、更有效地开发与利用奠定基础。本研究采用正相硅胶柱层析、半制备型液相色谱等分离技术以及NMR、MS、UV、IR等现代波谱学方法从多伞阿魏根部中分离鉴定11个单体化合物, 分别鉴定为baigene D (1)、baigene E (2)、baigene F (3)、β-kirialovin (4)、α-kirialovin (5)、falcarindiol (6)、ammoresinol (7)、dshamirone (8)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-3-[4-methyl-5-(4-methy1-2-furyl)-3(E)-pentenyl]-furo[3, 2-c]coumarin (9)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-2-[4, 8-dimethyl-3(E), 7-nonadi-enyl]-furo[3, 2-c]coumarin (10) 和baigene C (11)。结果表明, 化合物1~3为新的香豆素类化合物, 化合物4~6为首次从多伞阿魏中分离得到, 结构见图 1。
结果与讨论
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1 结构鉴定
化合物1  黄色油状; [α]$ {}_{\mathrm{D}}^{25} $ 80° (c 0.5, MeOH); UV λ$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{M}\mathrm{e}\mathrm{O}\mathrm{H}} $ (nm): 225, 315; HR-ESI-MS [M+H]+ m/z 395.185 3, 推测其分子式为C24H26O5, 不饱和度为12。1H NMR (表 1) 数据中显示3个苯环氢信号[δH 6.74 (1H, d, J = 1.8 Hz, H-6), δH 6.80 (1H, dd, J = 8.6, 1.8 Hz, H-8), δH 7.53 (1H, d, J = 8.6 Hz, H-9)], 3个烯氢信号[δH 5.11 (1H, t, J = 7.3 Hz, H-3′), δH 5.81 (1H, s, H-7′), δH 7.04 (1H, s, H-9′)], 1个连氧次甲基氢信号[δH 4.67 (1H, q, J = 6.8 Hz H-2)], 3个亚甲基氢信号[δH 2.03 (1H, m H-2′a), δH 1.92 (1H, m H-2′b), δH 1.67 (2H, t, J = 8.1 Hz, H-1′), δH 3.09 (2H, m, H-5′)], 4个甲基氢信号[δH 1.55 (3H, d, J = 6.8 Hz, 2-Me), δH 1.41 (3H, s, 3-Me), δH 1.41 (3H, s, 4′-Me), δH 1.93 (3H, d, J = 1.5 Hz, 8′-Me)]。13C NMR和DEPT (表 2) 显示出24个碳信号: 包括4个伯碳、3个仲碳、7个叔碳和10个季碳。对比文献[7]发现化合物1的母核是3, 4-呋喃骈香豆素, 且化合物1和已知化合物9分子式相同, UV和IR相似, 有文献报道化合物9为同种植物中分离得到[7]。对比两个化合物的1H NMR和13C NMR区别在于C-2 (1: δH 4.67, δC 94.5; 9: δH 4.95, δC 91.2), C-1′ (1: δH 1.67, δC 35.7; 9: δH 1.67, 1.87, δC 39.0), 2-Me (1: δH 1.55, δC 14.1; 9: δH 1.45, δC 15.9), 3-Me (1: δH 1.41, δC 24.0; 9: δH 1.26, δC 19.9)。在HMBC图谱(图 3) 中H-2′与C-3, H-2/H-3-Me与C-1′有相关信号, H-5′与C-7′, H-8′-Me与C-7′/C-8′/C-9′有相关信号, 由此推断出3, 4-呋喃骈香豆素与3-甲基呋喃通过一个异戊烯基相连, 即化合物1和9具有相同的平面结构, 综上判断化合物1是化合物9在C-2和C-3手性中心处的非对映异构体。关于化合物1的相对立体构型, ROESY图谱显示H-2与3-Me相关, 2-Me与H-1′相关, 确定H-2和3-Me位于同一侧, 2-Me与C-1′位于同一侧; H-3′与H-5′存在NOE相关, 确定C-3′和C-4′处的双键为E构型, 综上确定该化合物的相对立体构型。通过ECD计算方法确定化合物1的绝对构型, 计算采用Gaussian16软件完成, 优化构型和振动频率计算采用B3LYP/6-311G (d) 的级别计算。在优化基础上, 电子圆二色谱(ECD) 采用PBE0/def2-TZVP级别计算, 计算过程中采用SMD模型考虑MeOH溶液的溶剂效应。最后, 运用SpecDis软件生成玻尔兹曼平均ECD光谱。通过比较实验光谱和计算的ECD光谱(图 2), 证实化合物1的绝对构型为2S, 3S。由此, 化合物1的绝对立体结构被确定, 并命名为baigene D。
化合物2  黄色油状; [α]$ {}_{\mathrm{D}}^{25} $ 0° (c 0.5, MeOH); UV λ$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{M}\mathrm{e}\mathrm{O}\mathrm{H}} $ (nm): 225, 315; HR-ESI-MS [M+H]+ m/z 399.216 4, 推测其分子式为C24H30O5, 不饱和度为10。红外光谱特征吸收峰有苯环吸收峰(1 636 cm-1)、羰基吸收峰(1 709 cm-1) 以及呋喃环香豆素引起的双键吸收峰(1 612 cm-1), 且紫外光谱两处最大吸收也符合7-OH香豆素特征紫外吸收特征, 再结合化合物2的NMR图谱数据(表 1、2), 发现与已知化合物10具有相同的骨架。比较化合物10, 化合物2在C-7′处显示1个羰基碳信号(δC 217.0), C-8′处显示1个次甲基碳信号(δC 41.8), 而化合物10相对应处则显示2个烯碳信号。再通过二维图谱(图 3) 确证化合物2的母核及侧链的连接方式, 综上确定该化合物的平面结构。关于化合物2的相对立体构型, ROESY图谱显示H-3与H-1′相关, 2-Me与3-Me相关, 确定2-Me和3-Me位于同一侧, H-3和C-1′位于同一侧; H-3′与H-5′存在NOE相关, 确定C-3′和C-4′处的双键为E构型, 综上确定该化合物的相对立体构型。该化合物旋光值很小, 推测该化合物可能为外消旋体, 但目前的研究条件限制了进一步的拆分, 无法确定其绝对立体构型。综上, 推测出化合物2的相对立体结构, 并命名为baigene E。
化合物3  黄色油状; [α]$ {}_{\mathrm{D}}^{25} $ -4° (c 0.5, MeOH); UV λ$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{M}\mathrm{e}\mathrm{O}\mathrm{H}} $ (nm): 225, 315; HR-ESI-MS [M+H]+ m/z 399.216 7, 推测其分子式为C24H30O5, 不饱和度为10。化合物3分子式和已知化合物2分子式相同, 且UV和IR相似。由HSQC, HMBC, 1H-1H COSY图谱(图 3) 推断化合物3和2具有相同的平面结构。比较化合物3和2的 1H NMR和13C NMR数据, 区别(表 1、2) 也仅存在于C-3, C-1′, C-2-Me, C-3-Me, 综上判断化合物3是化合物2在C-2和C-3手性中心处的非对映异构体, 由此可以确定该化合物的平面结构。关于化合物3的相对立体构型, ROESY图谱显示H-3与2-Me相关、H-1′和3-Me有相关信号, 确定H-3与2-Me位于同一侧、3-Me与C-1′位于同一侧; H-3′与H-5′存在NOE相关, 确定C-3′和C-4′处的双键为E构型, 由此证实化合物3为化合物2的非对映异构体。综上确定该化合物的相对立体构型。该化合物旋光值很小, 推测该化合物可能为外消旋体, 但目前的研究条件限制了进一步的拆分, 无法确定其绝对立体构型。综上, 推测出化合物3的相对立体结构, 并命名为baigene F。
2 活性评价
采用MTT法对化合物5、7~11的人胃癌细胞(MKN-45) 增殖抑制活性进行评价。结果表明, 化合物7~11均表现出较强的抑制活性, 其抑制率分别为97.93% ± 0.31%、88.78% ± 3.21%、84.36% ± 1.82%、91.30% ± 2.64%、91.66% ± 1.50%; 化合物5表现出较弱增殖抑制活性, 其抑制率为29.09% ± 3.96%。
3 小结
本研究对多伞阿魏根部的乙酸乙酯部位进行了分离纯化, 鉴定了11个化合物: baigene D (1)、baigene E (2)、baigene F (3)、β-kirialovin (4)、α-kirialovin (5)、falcarindiol (6)、ammoresinol (7)、dshamirone (8)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-3-[4-methyl-5-(4-methy1-2-furyl)-3(E)-pentenyl]-furo[3, 2-c]coumarin (9)、2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-2-[4, 8-dimethyl-3(E), 7-nonadi-enyl]-furo[3, 2-c]coumarin (10), baigene C (11)。同时评价了化合物5、7~11的抑制MKN-45细胞抑制增殖活性。结果表明, 化合物1~3为新的香豆素类化合物, 化合物4~6为首次从多伞阿魏中分离得到。活性实验表明, 化合物7~11均表现出较强的抑制活性, 化合物5表现出较弱的抑制活性。
多伞阿魏根部具有显著的抗肿瘤药理作用。虽然国内外对其化学成分和药理作用进行了研究, 显示了其潜在的开发前景, 但对其抗癌药效物质基础及机制的系统深入研究尚不足。本研究在一定程度上充实了多伞阿魏的药效物质基础, 为今后的开发和利用提供了科学依据。在后续工作中, 我们将进一步深入研究多伞阿魏的药效物质基础、相关药理活性及作用机制, 以为其中药资源的科学利用提供更详尽的依据。
实验部分
收起
Bruker DRX-600 MHz型核磁共振波谱仪(德国Bruker公司); Waters 2535型半制备高效液相色谱仪、Q-TOF Micro LC-MS-MS质谱仪、Waters 2998 DAD检测器、Waters 2707自动进样器(美国Waters公司); Betasil C18柱(250 mm × 10 mm, 5 μm)、Thermo C18柱(150 mm × 10 mm, 5 µm, 美国Thermo公司); Phenomenex C6半制备柱(250 mm × 10 mm, 5 µm, 美国Phenomenex公司); COSMOSIL Cholester色谱柱(250 mm × 10 mm, 5 µm, 日本Cosmosil公司); Sephadex LH-20葡聚糖凝胶(美国Amersham公司); 柱色谱硅胶粉、薄层色谱硅胶GF254板(烟台江友硅胶开发有限公司); 色谱级甲醇、乙腈(美国TEDIA试剂公司); RPMI-1640培养基、二甲亚砜(DMSO, 美国Hyclone公司); 人胃癌细胞(MKN-45, 中国典型培养物保藏中心)。
实验用多伞阿魏于2021年8月购自新疆维吾尔自治区新疆麦迪森维药有限公司, 经伊犁师范大学庞克坚教授鉴定为伞形科阿魏属植物多伞阿魏[Ferula feruloides (Steudel) Korovin] 的干燥根。多伞阿魏根样本(No. SC0883) 保存于中南民族大学药学院植物标本库。
1 提取与分离
将多伞阿魏根部粉碎过筛, 得到重量约26.5 kg的粉末, 采用80%乙醇溶液对粉末浸泡提取(4 × 50 L, 每次7天), 将4次得到的提取液合并, 减压浓缩至无乙醇味即得浸膏4.6 kg。因其浸膏不能均匀分散在水体系中, 所以加适量甲醇到水中直至浸膏均匀分散在其中。先用石油醚进行萃取, 浓缩后得到石油醚部位浸膏422 g。将水体系中的甲醇蒸干, 使剩余浸膏均匀分散在水中。再依次用乙酸乙酯、正丁醇萃取, 减压回收得到乙酸乙酯部位浸膏1 717 g、正丁醇部位1 524 g。取乙酸乙酯部位的浸膏1 670 g采用正相硅胶柱层析(200~300目) 对其进行粗分。选用二氯甲烷-甲醇系统进行梯度洗脱(体积比100∶0→0∶1)。经薄层色谱法(TLC) 检测, 最终合并为7个组分(Fr.B1~Fr.B7)。取Fr.B3用正相硅胶柱层析(300~400目) 分离, 按二氯甲烷-甲醇(100∶1→30∶1) 的体系进行梯度洗脱, 经TLC检测合并分为8个组分(Fr.B3-1~Fr.B3-8), 再取Fr.B3-4用正相硅胶柱层析(10~40 μm) 分离, 采用石油醚-乙酸乙酯(100∶1→0∶1) 的体系进行梯度洗脱, 经TLC检测合并分为12个组分(Fr.B3-4-1~Fr.B3-4-12)。取Fr.B4用正相硅胶柱层析(300~400目) 分离, 采用石油醚-乙酸乙酯(20∶1→0∶1) 的体系进行梯度洗脱, 经TLC检测合并分为12个组分(Fr.B4-1~Fr.B4-12), 再取Fr.B4-5用正相硅胶柱层析(10~40 μm) 分离, 采用石油醚-乙酸乙酯(7∶1→0∶1) 的体系进行梯度洗脱, 经TLC检测合并分为10个组分(Fr.B4-5-1~Fr.B4-5-10)。
Fr.B3-4-9过凝胶柱粗分为3个组分(Fr.B3-4-9-1~Fr.B3-4-9-3), 再将Fr.B3-4-9-1用半制备高效液相色谱(Thermo C18柱, 30%~85%乙腈, 9.0 mL·min-1, 35 min, 流动相含有0.1%的甲酸) 细分成5个组分(Fr.B3-4-9-1-1~Fr.B3-4-9-1-5), 其中Fr.B3-4-9-1-1用半制备高效液相色谱(COSMOSIL Cholester色谱柱, 35%~44%乙腈, 4.0 mL·min-1, 41 min, 流动相含有0.1%的甲酸) 分离纯化得到化合物4 (7 mg) 和化合物5 (17.9 mg); Fr.B3-4-2经半制备高效液相色谱(COSMOSIL Cholester色谱柱, 75%~87%乙腈, 4.0 mL·min-1, 35 min, 流动相含有0.1%的甲酸) 分离纯化得到化合物8 (109.5 mg); Fr.B3-4-3经半制备高效液相色谱(Thermo C18柱, 60%~80%乙腈, 4.0 mL·min-1, 35 min, 流动相含有0.1%的甲酸) 分离纯化得到化合物7 (97.4 mg)。
Fr.B4-5-5经半制备高效液相色谱(Thermo C18柱, 60%~100%乙腈, 4.0 mL·min-1, 35 min, 流动相含有0.1%的甲酸) 分离纯化为11个组分(Fr.B4-5-5-1~Fr.B4-5-5-11), 其中Fr.B4-5-5-2为化合物6 (5.1 mg); Fr.B4-5-5-4经半制备高效液相色谱(COSMOSIL Cholester色谱柱, 55%~67%乙腈, 4.0 mL·min-1, 50 min, 流动相含有0.1%的甲酸) 分离纯化得到化合物1 (3.7 mg)、化合物9 (25.5 mg); Fr.B4-5-5-10经半制备高效液相色谱(COSMOSIL Cholester色谱柱, 67%~75%乙腈, 4.0 mL·min-1, 30 min, 流动相含有0.1%的甲酸) 分离纯化得到化合物10 (52.3 mg) 和化合物11 (21.3 mg); Fr.B4-5-6经半制备高效液相色谱(Thermo C18柱, 45%~75%乙腈, 4.0 mL·min-1, 25 min, 流动相含有0.1%的甲酸) 分离纯化为6个组分(Fr.B4-5-6-1~Fr.B4-5-6-6), 再将Fr.B4-5-6-3经半制备高效液相色谱(COSMOSIL Cholester色谱柱, 48%~54%乙腈, 4.0 mL·min-1, 40 min, 流动相含有0.1%的甲酸) 分离纯化得到化合物2 (2.3 mg) 和化合物3 (2.6 mg)。
2 结构鉴定
化合物1  黄色油状; [α]$ {}_{\mathrm{D}}^{25} $ 80° (c 0.5, MeOH); HR-ESI-MS [M+H]+ m/z 395.185 3 (计算值: 395.185 3); UV λ$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{M}\mathrm{e}\mathrm{O}\mathrm{H}} $ (nm): 225, 315; IR ν$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{K}\mathrm{B}\mathrm{r}} $: 1 690, 1 628; 1H NMR (600 MHz, CD3OD) 和13C NMR (150 MHz, CD3OD) 数据见表 1和表 2。
化合物2  黄色油状; [α]$ {}_{\mathrm{D}}^{25} $ 0° (c 0.5, MeOH); HR-ESI-MS [M+H]+ m/z 399.216 4 (计算值: 399.216 6); UV λ$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{M}\mathrm{e}\mathrm{O}\mathrm{H}} $ (nm): 225, 315; IR ν$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{K}\mathrm{B}\mathrm{r}} $: 1 709, 1 690, 1 636, 1 612; 1H NMR (600 MHz, CD3OD) 和13C NMR (150 MHz, CD3OD) 数据见表 1和表 2。
化合物3  黄色油状; [α]$ {}_{\mathrm{D}}^{25} $ -4° (c 0.5, MeOH); HR-ESI-MS [M+H]+ m/z 399.216 7 (计算值: 399.216 6); UV λ$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{M}\mathrm{e}\mathrm{O}\mathrm{H}} $ (nm): 225, 315; IR ν$ {}_{\mathrm{m}\mathrm{a}\mathrm{x}}^{\mathrm{K}\mathrm{B}\mathrm{r}} $: 1 709, 1 690, 1 636, 1 612; 1H NMR (600 MHz, CD3OD) 和13C NMR (150 MHz, CD3OD) 数据见表 1和表 2。
化合物4  黄色油状; ESI-MS m/z 331 [M+H]+, 其分子式为C19H22O5; 1H NMR (600 MHz, CD3OD): δH 1.26 (3H, d, J = 7.2 Hz, 3-Me), 1.50 (3H, s, 2-Me), 1.74 (1H, m, H-1′a), 1.81 (2H, m, H-2′), 1.86 (1H, m, H-1′b), 2.16 (3H, s, H-5′), 2.60 (2H, t, J = 6.8 Hz, H-3′), 3.18 (1H, q, J = 7.2 Hz, H-3), 3.89 (3H, s, 7-OMe), 6.93 (1H, d, J = 2.4 Hz, H-6), 6.95 (1H, dd, J = 9.4, 2.4 Hz, H-8), 7.59 (1H, d, J = 9.4 Hz, H-9); 13C NMR (150 MHz, CD3OD): δC 97.9 (C-2), 45.4 (C-3), 104.9 (C-3a), 163.4 (C-4), 158.2 (C-5a), 101.7 (C-6), 165.2 (C-7), 113.8 (C-8), 124.9 (C-9), 107.2 (C-9a), 166.9 (C-9b), 35.4 (C-1′), 19.5 (C-2′), 44.2 (C-3′), 211.2 (C-4′), 29.9 (C-5′), 25.5 (2-Me), 13.8 (3-Me), 56.4 (7-OMe)。上述数据与文献[8]报道基本一致, 确定该化合物为β-kirialovin。
化合物5  黄色油状; ESI-MS m/z 331 [M+H]+, 其分子式为C19H22O5; 1H NMR (600 MHz, CD3OD): δH 1.27 (3H, d, J = 7.0 Hz, 3-Me), 1.47 (3H, s, 2-Me), 1.72 (1H, m, H-1′a), 1.77 (2H, m, H-2′), 1.81 (1H, m, H-1′b), 2.11 (3H, s, H-5′), 2.54 (2H, t, J = 6.9 Hz, H-3′), 3.27 (1H, q, J = 7.0 Hz, H-3), 3.89 (3H, s, 7-OMe), 6.93 (1H, d, J = 2.4 Hz, H-6), 6.95 (1H, dd, J = 9.4, 2.4 Hz, H-8), 7.57 (1H, d, J = 9.4 Hz, H-9); 13C NMR (150 MHz, CD3OD): δC 98.5 (C-2), 43.2 (C-3), 104.5 (C-3a), 163.3 (C-4), 158.2 (C-5a), 101.7 (C-6), 165.2 (C-7), 113.8 (C-8), 124.9 (C-9), 107.1 (C-9a), 167.1 (C-9b), 42.0 (C-1′), 18.7 (C-2′), 43.9 (C-3′), 211.2 (C-4′), 29.9 (C-5′), 20.6(2-Me), 14.3 (3-Me), 56.4 (7-OMe)。上述数据与文献[8]报道基本一致, 确定该化合物为α-kirialovin。
化合物6  黄色油状; ESI-MS m/z 261 [M+H]+, 其分子式为C17H24O2; 1H NMR (600 MHz, CD3OD): δH 0.91 (3H, t, J = 7.2 Hz, H-17), 1.32 (2H, m, H-12), 1.32 (2H, m, H-13), 1.32 (2H, m, H-14), 1.32 (2H, m, H-15), 1.32 (2H, m, H-16), 2.12 (2H, qt, J = 7.5, 1.5 Hz, H-11), 5.16 (1H, dt, J = 8.3, Hz, H-8), 5.19 (1H, dt, J = 10.2, 1.4 Hz, H-1b), 5.41 (1H, dt, J = 17.1, 1.4 Hz, H-1a), 5.46 (1H, ddt, J = 10.8, 8.3, 1.4 Hz, H-9), 5.56 (1H, dtd, J = 10.7, 7.5, 1.4 Hz, H-10), 5.91 (1H, ddd, J = 17.1, 10.2, 5.5 Hz, H-2), 4.87 (1H, d, J = 5.5 Hz, H-3); 13C NMR (150 MHz, CD3OD): δC 116.3 (C-1), 134.1 (C-2), 63.8 (C-3), 81.1 (C-4), 70.1 (C-5), 68.7 (C-6), 79.7 (C-7), 58.8 (C-8), 129.8 (C-9), 134.6 (C-10), 28.5 (C-11), 30.3 (C-12), 30.3 (C-13), 30.4 (C-14), 30.2 (C-15), 23.7 (C-16), 14.6 (C-17)。上述数据与文献[9]报道基本一致, 确定该化合物为falcarindiol。
化合物7  黄色油状; ESI-MS m/z 383 [M+H]+, 其分子式为C24H30O4; 1H NMR (600 MHz, CDCl3): δH 1.58 (3H, s, H-13), 1.62 (3H, s, H-14), 1.67 (3H, s, H-12), 1.84 (3H, s, H-15), 2.00 (2H, m, H-8), 2.07 (2H, q, J = 7.4 Hz, H-9), 2.18 (2H, m, H-4), 2.18 (2H, q, J = 7.4 Hz, H-5), 3.41 (2H, d, J = 7.5 Hz, H-1), 5.08 (1H, t, J = 7.4 Hz, H-6), 5.08 (1H, t, J = 7.4 Hz, H-10), 5.45 (1H, t, J = 7.5 Hz, H-2), 6.83 (1H, dd, J = 8.7, 2.3 Hz, H-6′), 7.00 (1H, d, J = 2.3 Hz, H-8′), 7.64 (1H, d, J = 8.7 Hz, H-5′); 13C NMR (150 MHz, CDCl3): δC 23.9 (C-1), 120.4 (C-2), 143.0 (C-3), 39.8 (C-4), 26.1 (C-5), 123.1 (C-6), 136.6 (C-7), 39.8 (C-8), 26.8 (C-9), 124.5 (C-10), 131.6 (C-11), 25.9 (C-12), 17.9 (C-13), 16.6 (C-14), 16.3 (C-15), 165.1 (C-2′), 99.8 (C-3′), 162.6 (C-4′), 109.0 (C-4′a), 124.4 (C-5′), 113.3 (C-6′), 160.2 (C-7′), 102.8 (C-8′), 154.0 (C-8′a)。上述数据与文献[10]报道基本一致, 确定该化合物为ammoresinol。
化合物8  黄色油状; ESI-MS m/z 357 [M+H]+, 其分子式为C23H32O3; 1H NMR (600 MHz, CDCl3): δH 1.59 (3H, s, 5-Me), 1.59 (3H, s, 9-Me), 1.62 (3H, s, 13-Me), 1.68 (3H, s, H-14), 1.97 (2H, t, J = 7.5 Hz, H-6), 1.97 (2H, t, J = 7.5 Hz, H-10), 2.06 (2H, q, J = 7.5 Hz, H-7), 2.06 (2H, q, J = 7.5 Hz, H-11), 2.42 (2H, q, J = 7.7 Hz, H-3), 2.93 (2H, t, J = 7.7 Hz, H-2), 5.09 (1H, t, J = 7.5 Hz, H-8), 5.09 (1H, t, J = 7.5 Hz, H-12), 5.16 (1H, t, J = 7.7 Hz, H-4), 6.38 (1H, d, J = 9.0 Hz, H-3′), 6.38 (1H, dd, J = 9.0, 2.2 Hz, H-5′), 7.66 (1H, d, J = 2.2 Hz, H-6′); 13C NMR (150 MHz, CDCl3): δC 205.0 (C-1), 39.7 (C-2), 23.4 (C-3), 122.4 (C-4), 137.0 (C-5), 39.7 (C-6), 26.6 (C-7), 124.1 (C-8), 135.2 (C-9), 38.2 (C-10), 26.8 (C-11), 124.4 (C-12), 131.4 (C-13), 25.8 (C-14), 16.1 (5-Me), 16.1 (9-Me), 17.8 (13-Me), 113.9 (C-1′), 165.2 (C-2′), 103.6 (C-3′), 162.8 (C-4′), 107.9 (C-5′), 133.5 (C-6′)。上述数据与文献[11]报道基本一致, 确定该化合物为dshamirone。
化合物9  黄色油状; ESI-MS m/z 395 [M+H]+, 其分子式为C24H26O5; 1H NMR (600 MHz, CD3OD): δH 1.26 (3H, s, 3-Me), 1.45 (3H, d, J = 6.7 Hz, 2-Me), 1.50 (3H, s, 4′-Me), 1.67 (1H, m, H-1′a), 1.87 (1H, m, H-1′b), 1.94 (3H, s, 8′-Me), 1.94 (1H, m H-2′a), 2.09 (1H, m H-2′b), 3.13 (2H, m, H-5′), 4.95 (1H, q, J = 6.7 Hz, H-2), 5.18 (1H, d, J = 7.7 Hz, H-3′), 5.84 (1H, s, H-7′), 6.73 (1H, d, J = 2.3 Hz, H-6), 6.80 (1H, dd, J = 8.8, 2.3 Hz, H-8), 7.05 (1H, s, H-9′), 7.52 (1H, d, J = 8.8 Hz, H-9); 13C NMR (150 MHz, CD3OD): δC 91.2 (C-2), 48.0 (C-3), 106.1 (C-3a), 163.1 (C-4), 158.3 (C-5a), 103.4 (C-6), 163.1 (C-7), 114.3 (C-8), 125.1 (C-9), 106.2 (C-9a), 168.0 (C-9b), 39.0 (C-1′), 24.6 (C-2′), 127.1 (C-3′), 133.5 (C-4′), 39.2 (C-5′), 155.4 (C-6′), 109.8 (C-7′), 121.7 (C-8′), 138.9 (C-9′), 15.9 (2-Me), 19.9 (3-Me), 15.9 (4′-Me), 9.8 (8′-Me)。上述数据与文献[7]报道基本一致, 确定该化合物为2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-3-[4-methyl-5-(4-methy1-2-furyl)-3(E)-pentenyl]-furo[3, 2-c]coumarin。
化合物10  黄色油状; ESI-MS m/z 405 [M+Na]+, 其分子式为C24H30O4; 1H NMR (600 MHz, CD3OD): δH 1.28 (3H, d, J = 7.0 Hz, 3-Me), 1.47 (3H, s, 2-Me), 1.56 (3H, s, 4′-Me), 1.56 (3H, d, 8′-Me), 1.64 (3H, d, J = 1.5 Hz, H-9′), 1.81 (2H, m, Hz, H-1′), 1.92 (2H, t, J = 7.7 Hz, H-5′), 2.03 (2H, q, J = 7.7 Hz, H-6′), 2.14 (2H, m, H-2′), 3.26 (1H, q, J = 7.0 Hz, H-3), 5.05 (1H, tp, J = 7.7, 1.5 Hz, H-7′), 5.13 (1H, tq, J = 7.2, 1.4 Hz, H-3′), 6.74 (1H, d, J = 2.3 Hz, H-6), 6.80 (1H, dd, J = 8.6, 2.3 Hz, H-8), 7.51 (1H, d, J = 8.6 Hz, H-9); 13C NMR (150 MHz, CD3OD): δC 98.4 (C-2), 43.0 (C-3), 103.9 (C-3a), 163.6 (C-4), 158.2 (C-5a), 103.5 (C-6), 163.6 (C-7), 114.3 (C-8), 125.3 (C-9), 106.1 (C-9a), 167.4 (C-9b), 42.7 (C-1′), 23.1 (C-2′), 124.8 (C-3′), 136.6 (C-4′), 40.7 (C-5′), 27.6 (C-6′), 125.1 (C-7′), 132.1 (C-8′), 25.8 (C-9′), 20.4 (2-Me), 14.4 (3-Me), 15.9 (4′-Me), 17.7 (8′-Me)。上述数据与文献[12]报道基本一致, 确定该化合物为2, 3-dihydro-7-hydroxy-2S*, 3R*-dimethyl-2-[4, 8-dimethyl-3(E), 7-nonadi-enyl]-furo[3, 2-c]coumarin。
化合物11  黄色油状; ESI-MS m/z 405 [M+Na]+, 其分子式为C24H30O4; 1H NMR (600 MHz, CD3OD): δH 1.26 (3H, d, J = 7.0 Hz, 3-Me), 1.48 (3H, s, 2-Me), 1.59 (3H, s, 8′-Me), 1.65 (3H, s, 4′-Me), 1.65 (3H, s, H-9′), 1.75 (1H, ddd, J = 14.1, 10.8, 5.4 Hz, H-1′a), 1.89 (1H, ddd, J = 14.1, 10.8, 5.4 Hz, H-1′b), 2.00 (2H, t, J = 7.4 Hz, H-5′), 2.08 (2H, q, J = 7.4 Hz, H-6′), 2.26 (2H, m, H-2′), 3.17 (1H, q, J = 7.0 Hz, H-3), 5.09 (1H, tp, J = 7.4, 1.5 Hz, H-7′), 5.20 (1H, tq, J = 7.1, 1.4 Hz, H-3′), 6.74 (1H, d, J = 2.2 Hz, H-6), 6.86 (1H, dd, J = 8.6, 2.2 Hz, H-8), 7.52 (1H, d, J = 8.6 Hz, H-9); 13C NMR (150 MHz, CD3OD): δC 97.9 (C-2), 45.4 (C-3), 104.1 (C-3a), 163.6 (C-4), 158.2 (C-5a), 103.5 (C-6), 163.6 (C-7), 114.3 (C-8), 125.3 (C-9), 106.2 (C-9a), 167.2 (C-9b), 36.2 (C-1′), 23.8 (C-2′), 125.0 (C-3′), 136.6 (C-4′), 40.8 (C-5′), 27.6 (C-6′), 125.1 (C-7′), 132.2 (C-8′), 25.8 (C-9′), 25.5 (2-Me), 13.8 (3-Me), 16.0 (4′-Me), 17.7 (8′-Me)。上述数据与文献[11]报道基本一致, 确定该化合物为baigene C。
3 细胞活力测定
采用MTT法对化合物5、7~11的人胃癌细胞(MKN-45) 增殖抑制活性进行评价。待测样品的配制: 以DMSO作为溶剂, 将化合物均配成浓度为0.25 mol·L-1的溶液, 然后再用0.1 mol·L-1 PBS (磷酸氢二钠-磷酸二氢钠) 缓冲溶液将其稀释为5.0 mmol·L-1的待测化合物溶液。将MKN-45细胞离心、消化、重悬后接种于96孔细胞培养板然后孵育, 直到覆盖面积达到85%, 空白组不接种细胞。再使用特定剂量浓度的化合物(0和100 μmol·L-1) 处理细胞24 h, 随后清除每孔中的液体, 加入浓度为5 mg·mL-1的MTT, 在37 ℃和5% CO2浓度的培养箱中孵育30 min。吸弃每孔上清液, 加入150 μL DMSO。通过酶标仪在波长490 nm下测定吸光度(OD) 值。
实验组: 4 μL浓度为5 mmol·L-1的待测样品溶液+ 196 μL RPMI-1640细胞培养基; 对照组: 4 μL 2% DMSO-PBS溶液+ 196 μL RPMI-1640细胞培养基。细胞抑制率的计算公式为抑制率(%) = [1-(OD实验-OD空白) / (OD对照-OD空白)] × 100%。
作者贡献: 杨新洲和胡燕负责实验设计; 毕英赫负责实验实施、数据分析以及文章的撰写; 庞克坚对药材的购买和鉴定提供帮助; 李卉子对新化合物结构鉴定提供建议; 叶尔兰·巴合特江和木古丽·木哈西对微量化合物的分离提供技术帮助; 杨新洲和胡燕负责文章的审阅和提出论文写作的建议, 并最终定稿。
利益冲突: 作者声明无利益冲突。
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  • 新疆维吾尔自治区区域协同创新专项上海合作组织科技伙伴计划及国际科技合作计划项目(2023E01019)
  • 国家自然科学基金资助项目(82374144)
  • 国家自然科学基金资助项目(82160796)
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参考文献 引证文献
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2024年第59卷第7期
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doi: 10.16438/j.0513-4870.2023-1424
  • 接收时间：2023-12-20
  • 首发时间：2025-11-26
  • 出版时间：2024-07-12
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  • 收稿日期：2023-12-20
  • 修回日期：2024-02-29
基金
新疆维吾尔自治区区域协同创新专项上海合作组织科技伙伴计划及国际科技合作计划项目(2023E01019)
国家自然科学基金资助项目(82374144)
国家自然科学基金资助项目(82160796)
作者信息
    1.中南民族大学药学院, 湖北 武汉 430074
    2.伊犁师范大学, 新疆 伊宁 835000

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*胡燕, Tel: 86-27-67841196, E-mail: ;
杨新洲, E-mail:
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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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