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Article(id=1209788337934701200, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1209788321396552074, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2021-1226, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1629475200000, receivedDateStr=2021-08-21, revisedDate=1633708800000, revisedDateStr=2021-10-09, acceptedDate=null, acceptedDateStr=null, onlineDate=1766365616544, onlineDateStr=2025-12-22, pubDate=1644595200000, pubDateStr=2022-02-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1766365616544, onlineIssueDateStr=2025-12-22, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1766365616544, creator=13701087609, updateTime=1766365616544, updator=13701087609, issue=Issue{id=1209788321396552074, tenantId=1146029695717560320, journalId=1189982191388893191, year='2022', volume='57', issue='2', pageStart='251', pageEnd='546', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1766365612600, creator=13701087609, updateTime=1766370652531, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1209809460445451136, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1209788321396552074, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1209809460445451137, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1209788321396552074, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=428, endPage=432, ext={EN=ArticleExt(id=1209788338404463285, articleId=1209788337934701200, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Sesquiterpenoids and iridoids from Valeriana jatamansi with anti-inflammatory and anti-influenza virus properties, columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

Three sesquiterpenoids and nine iridoids were isolated from the roots and rhizomes of Valeriana jatamansi by various chromatographic methods. Their structures were identified by physicochemical properties, NMR and MS data. Among them, valeriananoid G (1) was a new patchoulol-type sesquiterpenoid, and compound 3 was isolated from the genus Valeriana for the first time. Compounds 3 and 10 exhibited significant inhibitory effects on nitric oxide production induced by lipopolysaccharide in RAW 264.7 macrophages, with IC50 values of 19.00 and 3.66 μmol·L-1, respectively. In addition, compounds 4, 6 and 12 showed anti-influenza virus activity with IC50 values of 51.75, 51.40 and 102.08 μmol·L-1, respectively.

, correspAuthors=Hong-mei LI, authorNote=null, correspAuthorsNote=null, copyrightStatement=Copyright ©2022 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=Dao-qun SHI, Yun WANG, Kai-rui RAO, Na JIANG, Dan LIU, Rong-tao LI, Hong-mei LI), CN=ArticleExt(id=1209788340203819802, articleId=1209788337934701200, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=蜘蛛香中的倍半萜和环烯醚萜类成分及其抗炎和抗流感病毒活性, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用多种色谱技术从蜘蛛香根和根茎中分离得到3个倍半萜和9个环烯醚萜，并依据理化性质、NMR和MS数据鉴定了化合物的结构。其中，蜘蛛香酯G（1）是新的广藿香醇型倍半萜，化合物3为首次从缬草属植物中分离得到。化合物3和10可显著抑制脂多糖（LPS）诱导的小鼠巨噬细胞RAW 264.7中NO的释放，IC50值分别为19.00和3.66 μmol·L-1。化合物4、6和12具有一定的抗流感病毒活性，IC50值分别为51.75、51.40和102.08 μmol·L-1。

, correspAuthors=李洪梅, authorNote=null, correspAuthorsNote=
*李洪梅, Tel: 86-871-65920569, E-mail:
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No.12
δH (J in Hz)δC, mult.δH (J in Hz)δC, mult.
12.03 (dd, 14.0, 7.7)
1.59 (overlap)		37.1 t2.04 (dd, 14.0, 7.7)
1.59 (overlap)		35.6 t
24.79 (ddd, 9.6, 7.7, 1.2)76.1 d4.79 (ddd, 9.7, 7.7, 1.6)75.0 d
31.41 (overlap)44.9 d1.43 (m)43.3 d
441.4 s40.0 s
576.1 s74.7 s
61.74 (dd, 14.2, 5.3)
1.60 (m)		32.8 t1.74 (dd, 14.2, 5.8)
1.59 (m)		31.5 t
71.50 (m)
1.38 (m)		29.5 t1.50 (m)
1.36 (m)		28.1 t
81.97 (m)28.9 d1.96 (m)27.6 d
91.42 (m)44.0 d1.43 (m)42.6 d
1040.0 s38.6 s
111.59 (m)
1.37 (m)		24.6 t1.59 (m)
1.36 (m)		24.1 t
120.82 (d, 6.7)19.2 q0.82 (d, 6.7)17.8 q
131.12 (s)28.9 q1.12 (s)27.4 q
141.09 (s)25.5 q1.09 (s)23.1 q
150.89 (s)20.8 q0.89 (s)19.4 q
1′174.6 s171.3 s
2′2.16 (m)44.9 t2.00 (s)20.1 s
3′2.07 (m)26.8 d
4′/5′0.95 (d, 6.6)22.8 q
), ArticleFig(id=1209809054201942779, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1209788337934701200, language=CN, label=Table 1, caption=

1H (600 MHz) and 13C NMR (150 MHz) data of compounds 1 and 2 (CD3OD)

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No.12
δH (J in Hz)δC, mult.δH (J in Hz)δC, mult.
12.03 (dd, 14.0, 7.7)
1.59 (overlap)		37.1 t2.04 (dd, 14.0, 7.7)
1.59 (overlap)		35.6 t
24.79 (ddd, 9.6, 7.7, 1.2)76.1 d4.79 (ddd, 9.7, 7.7, 1.6)75.0 d
31.41 (overlap)44.9 d1.43 (m)43.3 d
441.4 s40.0 s
576.1 s74.7 s
61.74 (dd, 14.2, 5.3)
1.60 (m)		32.8 t1.74 (dd, 14.2, 5.8)
1.59 (m)		31.5 t
71.50 (m)
1.38 (m)		29.5 t1.50 (m)
1.36 (m)		28.1 t
81.97 (m)28.9 d1.96 (m)27.6 d
91.42 (m)44.0 d1.43 (m)42.6 d
1040.0 s38.6 s
111.59 (m)
1.37 (m)		24.6 t1.59 (m)
1.36 (m)		24.1 t
120.82 (d, 6.7)19.2 q0.82 (d, 6.7)17.8 q
131.12 (s)28.9 q1.12 (s)27.4 q
141.09 (s)25.5 q1.09 (s)23.1 q
150.89 (s)20.8 q0.89 (s)19.4 q
1′174.6 s171.3 s
2′2.16 (m)44.9 t2.00 (s)20.1 s
3′2.07 (m)26.8 d
4′/5′0.95 (d, 6.6)22.8 q
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CompoundIC50/μmol·L-1CC50/μmol·L-1
319.00> 50
103.6614.68
L-NMMA21.80> 50
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Inhibition of LPS-stimulated NO production by compounds 3 and 10

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CompoundIC50/μmol·L-1CC50/μmol·L-1
319.00> 50
103.6614.68
L-NMMA21.80> 50
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CompoundIC50/μmol·L-1CC50/μmol·L-1
451.75> 200
651.40> 200
12102.08> 200
Amantadine67.90—
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Anti-influenza virus activity of compounds 4, 6 and 12

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CompoundIC50/μmol·L-1CC50/μmol·L-1
451.75> 200
651.40> 200
12102.08> 200
Amantadine67.90—
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蜘蛛香中的倍半萜和环烯醚萜类成分及其抗炎和抗流感病毒活性
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石道群 , 王云 , 饶凯瑞 , 蒋娜 , 刘丹 , 李蓉涛 , 李洪梅 *
药学学报 | 研究论文 2022,57(2): 428-432
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药学学报 | 研究论文 2022, 57(2): 428-432
蜘蛛香中的倍半萜和环烯醚萜类成分及其抗炎和抗流感病毒活性
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石道群, 王云, 饶凯瑞, 蒋娜, 刘丹, 李蓉涛, 李洪梅*
作者信息
  • 昆明理工大学生命科学与技术学院, 云南 昆明 650500

通讯作者:

*李洪梅, Tel: 86-871-65920569, E-mail:
Sesquiterpenoids and iridoids from Valeriana jatamansi with anti-inflammatory and anti-influenza virus properties
Dao-qun SHI, Yun WANG, Kai-rui RAO, Na JIANG, Dan LIU, Rong-tao LI, Hong-mei LI*
Affiliations
  • Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, China
出版时间: 2022-02-12 doi: 10.16438/j.0513-4870.2021-1226
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摘要
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采用多种色谱技术从蜘蛛香根和根茎中分离得到3个倍半萜和9个环烯醚萜，并依据理化性质、NMR和MS数据鉴定了化合物的结构。其中，蜘蛛香酯G（1）是新的广藿香醇型倍半萜，化合物3为首次从缬草属植物中分离得到。化合物3和10可显著抑制脂多糖（LPS）诱导的小鼠巨噬细胞RAW 264.7中NO的释放，IC50值分别为19.00和3.66 μmol·L-1。化合物4、6和12具有一定的抗流感病毒活性，IC50值分别为51.75、51.40和102.08 μmol·L-1。

蜘蛛香  /  倍半萜  /  环烯醚萜  /  抗炎  /  抗流感病毒

Three sesquiterpenoids and nine iridoids were isolated from the roots and rhizomes of Valeriana jatamansi by various chromatographic methods. Their structures were identified by physicochemical properties, NMR and MS data. Among them, valeriananoid G (1) was a new patchoulol-type sesquiterpenoid, and compound 3 was isolated from the genus Valeriana for the first time. Compounds 3 and 10 exhibited significant inhibitory effects on nitric oxide production induced by lipopolysaccharide in RAW 264.7 macrophages, with IC50 values of 19.00 and 3.66 μmol·L-1, respectively. In addition, compounds 4, 6 and 12 showed anti-influenza virus activity with IC50 values of 51.75, 51.40 and 102.08 μmol·L-1, respectively.

Valeriana jatamansi Jones  /  sesquiterpenoid  /  iridoid  /  anti-inflammatory  /  anti-influenza virus
石道群, 王云, 饶凯瑞, 蒋娜, 刘丹, 李蓉涛, 李洪梅. 蜘蛛香中的倍半萜和环烯醚萜类成分及其抗炎和抗流感病毒活性. 药学学报, 2022 , 57 (2) : 428 -432 . DOI: 10.16438/j.0513-4870.2021-1226
Dao-qun SHI, Yun WANG, Kai-rui RAO, Na JIANG, Dan LIU, Rong-tao LI, Hong-mei LI. Sesquiterpenoids and iridoids from Valeriana jatamansi with anti-inflammatory and anti-influenza virus properties[J]. Acta Pharmaceutica Sinica, 2022 , 57 (2) : 428 -432 . DOI: 10.16438/j.0513-4870.2021-1226
正文
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缬草属(Valeriana) 植物全球约有250种[1]。该属植物在欧洲作为镇静安眠药用于轻、中度失眠, 药用历史悠久[2]。目前, 该属植物的化学成分研究主要集中在低极性部位, 环烯醚萜和倍半萜是其中两类主要的化学成分[3]。蜘蛛香(Valeriana jatamansi Jones), 又名马蹄香、雷公七、臭药、老虎七等, 为缬草属多年生草本植物, 主要分布于中国西南地区和印度等地[4]。蜘蛛香作为我国著名的传统中药, 药用历史悠久, 以其根和根茎入药, 可用于治疗脘腹胀痛、食积不化、腹泻痢疾、风湿痹痛、腰膝酸软、睡眠紊乱、神经紊乱、癫痫、精神错乱、蛇中毒、皮肤病和流感等多种疾病[5-10]。近年来, 本课题组先后报道了一系列蜘蛛香中的环烯醚萜类成分, 其中一些具有显著的抗炎和抗流感病毒活性[4, 8, 11]。为了从蜘蛛香中寻找更多具有显著抗炎和抗流感病毒活性的成分, 本研究对其进行了更为深入的化学成分研究和活性评价。
本实验从蜘蛛香根和根茎中分离得到3个倍半萜和9个环烯醚萜(图 1), 通过各种波谱技术, 分别鉴定为蜘蛛香酯G (1)、蜘蛛香酯C (2)[12]、cinnamolide (3)[13]、8-methoxy-4-acetoxy-3-chlormethyl-10-methylen-2, 9-dioxa-tricyclo [4.3.1.03, 7] decan (4)[6, 14]、(1S, 3R, 5R, 7S, 8R, 9S)-3, 8-epoxy-1-O-methyl-5-hydroxyvalechlorine (5)[15]、4β-hydroxy-8β-methoxy-10-methylene-2, 9-dioxatricyclo [4.3.1.03, 7] decane (6)[16]、chlorovaltrate Q (7)[6]、(3S, 4R, 5S, 7S, 8S, 9S)-3, 8-epoxy-7-hydroxy-4, 8-dimethylperhydrocyclopenta [c] pyran (8)[17]、(3S, 4S, 5S, 7S, 8S, 9S)-3, 8-ethoxy-7-dihydroxy-4, 8-dimethylperhydrocyclopenta [c] pyran (9)[17]、蜘蛛香素E (10)[18]、valtrate hydrin B1 (11)[19]和11-methoxyviburtinal (12)[20]。其中, 化合物1为新的广藿香醇型倍半萜, 化合物3为首次从缬草属植物中分离得到。体外实验结果显示, 化合物3和10有明显的抗炎活性, 化合物4、6和12有一定的抗流感病毒活性。
结果与讨论
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1 结构鉴定
化合物1为无色油状物。通过高分辨质谱HR-ESI-MS的准分子离子峰m/z 345.239 6 [M+Na]+ (计算值345.240 0) 和667.491 8 [2M+Na]+ (计算值667.490 8), 推导出其分子式为C20H34O3, 不饱和度为4。红外光谱吸收峰表明该化合物中存在羟基(3 490 cm-1) 和酯羰基(1 704 cm-1)。1H NMR谱(表 1) 显示了6个甲基信号, 包括3个单峰[δH 1.12 (3H, s, Me-13)、1.09 (3H, s, Me-14) 和0.89 (3H, s, Me-15)] 和3个二重峰[δH 0.82 (3H, d, J = 6.7 Hz, Me-12) 和0.95 (6H, d, J = 6.6 Hz, Me-4′, 5′)]。此外, 在1H NMR谱中还观察到1个连氧次甲基信号[δH 4.79 (1H, ddd, J = 9.6, 7.7, 1.2 Hz, H-2)]。在13C NMR和DEPT谱(表 1) 中, 观察到了20个碳信号, 包括6个甲基[δC 19.2 (C-12)、28.9 (C-13)、25.5 (C-14)、20.8 (C-15) 和22.8 (C-4′、5′)]、5个亚甲基[δC 37.1 (C-1)、32.8 (C-6)、29.5 (C-7)、24.6 (C-11) 和44.9 (C-2′)]、5个次甲基[δC 76.1 (C-2)、44.9 (C-3)、28.9 (C-8)、44.0 (C-9) 和26.8 (C-3′)]、1个连氧叔碳[δC 76.1 (C-5)]、1个羰基碳[δC 174.6 (C-1′)] 和2个季碳[δC 41.4 (C-4) 和40.0 (C-10)]。
将化合物1的上述NMR数据与具有三环骨架的广藿香醇型倍半萜蜘蛛香酯C (2)[12]在相同溶剂(CD3OD) 中测得的NMR数据(表 1) 进行仔细比较, 发现二者的结构非常相似, 主要区别在于化合物2中C-2位的乙酰氧基被化合物1中的异戊酰氧基取代, 这一推断通过H-2, H-2′ (δH 2.16) 和H-3′ (δH 2.07) 与C-1′的HMBC相关(图 2) 得到证实。另外, H-1 (δH 2.03, 1.59)、H-3 (δH 1.41)、H-6 (δH 1.74, 1.60)、H-7 (δH 1.50, 1.38) 以及Me-13、Me-14和Me-15与低场信号δC 76.1 (s) 的HMBC相关说明该碳信号为C-5且被羟基取代。甲基信号与周围碳信号的HMBC相关, 即Me-12与C-7、C-8和C-9, Me-13 (14) 与C-3、C-4、C-5和C-14 (13), Me-15与C-1、C-5、C-9和C-10, 亚甲基信号H-11 (δH 1.59, 1.37) 与C-2、C-3、C-4、C-8、C-9和C-10的一系列HMBC相关, 以及1H-1H COSY谱(图 2) 中H2-1/H-2/H-3/H2-11/H-9/H-8/H2-7/H2-6和H-8/Me-12的质子自旋系统, 充分证实了化合物1结构中三环骨架的存在以及如图 1所示的平面结构。
化合物1的相对构型是结合ROESY实验、耦合常数、旋光值和生源关系来确定的。根据ROESY谱(图 2) 中H-2与Me-14的NOE相关, H-2的相对构型被确定为α构型。仔细对比发现, 化合物1和2中H-2的耦合裂分情况[1: δH 4.79 (ddd, J = 9.6, 7.7, 1.2 Hz); 2: δH 4.79 (ddd, J = 9.7, 7.7, 1.6 Hz)] 非常相似, 说明化合物1的H-2与H-11之间也存在w型远程耦合, 耦合常数为1.2 Hz, 这进一步证实了H-2为α构型[12]。因此, 化合物1中C-2位的异戊酰氧基为β构型。另外, H-8与Me-15之间的ROESY相关说明Me-12与Me-15不共面。通过比较化合物1 ([α]$ {}_{\mathrm{D}}^{25} $ -47.29) 和2 ([α]$ {}_{\mathrm{D}}^{28} $ -56.88) 的旋光数据, 同时结合生源考虑, 化合物1中其他手性碳的相对构型应与化合物2中一致。综合上述所有数据, 化合物1的结构被鉴定并命名为蜘蛛香酯G。
2 化合物活性检测
采用Griess法, 考察了化合物1~12抑制LPS诱导的小鼠巨噬细胞RAW 264.7释放NO能力。结果(表 2) 表明, 以左旋单甲基精氨酸(L-NMMA) 为对照, 化合物3和10具有明显的抗炎作用, IC50值分别为19.00和3.66 μmol·L-1。化合物10虽然活性显著, 但细胞毒性较高(CC50 = 14.68 μmol·L-1), 化合物3对细胞未表现出毒性作用(CC50 > 50 μmol·L-1)。
另外, 本文采用流感病毒A/Puerto Rico/8/1934 (H1N1) 感染MDCK细胞模型, 对化合物1~12进行抗流感病毒活性评价, 以金刚烷胺(amantadine) 作为阳性对照。实验结果(表 3) 表明, 化合物4、6和12具有一定的抗流感病毒活性, IC50值分别为51.75、51.40和102.08 μmol·L-1。对比化合物4~7的结构发现, C-5位羟基的存在可能会降低活性。《云南中草药》[5]记载: 蜘蛛香“消食行气。主治消化不良, 小儿咳嗽, 疳积, 流感, 疟疾。”上述结果进一步证实环烯醚萜是蜘蛛香发挥抗流感病毒活性的重要活性成分。
3 讨论
本文对蜘蛛香根和根茎进行了系统的化学成分研究, 共分离鉴定了12个单体化合物, 包括3个倍半萜和9个环烯醚萜。化合物1为新的广藿香醇型倍半萜, 化合物3为首次从缬草属植物中分离得到。本研究发现化合物3和10具有明显的抗炎活性, 化合物4、6和12具有一定的抗流感病毒活性。这一结果加深了对蜘蛛香根和根茎中倍半萜和环烯醚萜类化学成分的认识。同时, 对蜘蛛香的传统抗流感病毒作用与化学成分之间的关系也有了初步认识。
实验部分
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Jasco DIP-370数字旋光仪(日本东京JASCO公司); Bruker Avance Ⅲ HD 600型核磁共振仪(Bruker公司); Agilent 6200系列TOF和6500系列Q-TOF LC/MS系统(Agilent公司); Bruker Tensor-27红外光谱仪(Bruker公司); Agilent 1200和Agilent 1100型高效液相色谱仪(Agilent公司), 配备ZORBAX SB-C-18反相柱(分析型: 46 mm × 250 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(Agilent公司); Hei-VAP Value G3型旋转蒸发仪(Heidolph公司); 3111型CO2恒温培养箱(Thermofisher公司); CKX41型倒置相差显微镜(OLYMPUS); Spectra Max M2多功能读板机(Moleccular Devices公司); 薄层色谱硅胶GF254、柱色谱硅胶(青岛海洋化工厂); SephadexLH-20 (Amersham Biosciences公司); MCI填充材料(MCI-gel CHP-20P, 75~150 μm, Mitsubishi公司); ODS-C18 (75 μm) 反相填充材料(YMC公司); MTT、DMSO和金刚烷胺(Solarbio公司); 胎牛血清(Hyclone公司); 胰蛋白酶(Roche公司); DMEM细胞培养基(Invitrogen公司); 小鼠单核巨噬细胞RAW 264.7 (中科院昆明细胞库, 编号KCB200603YJ); 左旋单甲基精氨酸(L-NMMA, 碧云天生物技术有限公司)。
药材样品于2017年6月购自昆明市新螺蛳湾药材市场, 并由昆明理工大学陈宣钦副教授鉴定为蜘蛛香Valeriana jatamansi Jones的根和根茎, 凭证标本(KUMST 20170601) 存放于昆明理工大学生命科学与技术学院资源药物化学重点实验室。
1 提取与分离
干燥的蜘蛛香根和根茎(25 kg) 经粉碎后在室温下用95%乙醇冷浸提取3次(每次24 h, 37 L), 合并提取液, 浓缩得到浸膏。将浸膏与水混悬后依次用石油醚、乙酸乙酯和正丁醇萃取, 分别得到相应的石油醚相、乙酸乙酯相和正丁醇相。乙酸乙酯相(64 g) 利用硅胶柱色谱(80~100目硅胶64 g拌样, 200~300目硅胶300 g装柱) 进行粗划段, 经石油醚/乙酸乙酯(80∶1→0∶1) 梯度洗脱, 得到3个组分, Frs. 1~3。Fr.2 (20 g) 利用硅胶柱色谱, 石油醚/乙酸乙酯(20∶1→0∶1) 作为流动相进行梯度洗脱, 得到3个组分, Frs.2-1~2-3。Fr.2-3 (8.5 g) 经过硅胶柱色谱, 以石油醚/乙酸乙酯(70∶1→0∶1)为流动相进行梯度洗脱, 得到4个组分, 即Frs.2-3-1~2-3-4。Fr.2-3-1 (70 mg) 通过硅胶柱色谱, 以石油醚/乙酸乙酯(60∶1→0∶1) 作为流动相进行洗脱, 得到化合物4 (6.0 mg)。采用与Fr.2-3-1相同的溶剂系统, 将Fr.2-3-2 (5 g) 分为3个部分, 即Frs.2-3-2-1~2-3-2-3。Fr.2-3-2-1 (600 mg) 通过硅胶柱色谱, 以石油醚/异丙醇(60∶1→0∶1) 作为流动相进一步纯化, 得到化合物5 (5.5 mg) 和7 (4.3 mg)。化合物12 (800 mg) 是通过硅胶柱色谱(石油醚/乙酸乙酯50∶1→0∶1) 从组分Fr.2-3-2-2 (1.5 g) 中得到的。Fr.2-3-2-3 (48 mg) 通过半制备HPLC (55%甲醇/水) 纯化得到化合物6 (10 mg, tR = 11.6 min)。Fr.2-3-3 (233 mg) 经过Sphadex LH-20凝胶柱色谱(甲醇) 分离得到化合物8 (10 mg) 和9 (12 mg)。Fr.2-3-4 (1.5 g) 通过硅胶柱色谱(二氯甲烷/甲醇100∶1→0∶1) 梯度洗脱得到3个组分, 即Frs.2-3-4-1~2-3-4-3。化合物10 (9 mg) 是通过硅胶柱色谱(石油醚/异丙醇60∶1→0∶1) 从组分Fr.2-3-4-1 (125 mg) 中得到的。Fr.2-3-4-2 (97 mg) 通过半制备HPLC (45%乙腈/水) 纯化得到化合物11 (9 mg, tR = 12.4 min)。Fr.2-3-4-3 (650 mg) 通过Sphadex LH-20凝胶柱色谱(甲醇) 得到两个组分, 即Fr.2-3-4-3-1和Fr.2-3-4-3-2。Fr.2-3-4-3-1 (300 mg) 通过半制备HPLC (70%甲醇/水) 和Sephadex LH-20凝胶柱色谱(甲醇) 进一步纯化, 得到化合物2 (6 mg) 和3 (12 mg)。Fr.2-3-4-3-2 (56 mg) 通过Sephadex LH-20凝胶柱色谱(甲醇) 纯化, 得到化合物1 (8 mg)。
2 结构鉴定
化合物1  无色油状, [α]$ {}_{\mathrm{D}}^{25.0} $ -47.29 (c 0.14, MeOH); HR-ESI-MS (pos.): m/z 345.239 6 [M+Na]+ (C20H34O3Na计算值345.240 0), 667.491 8 [2M+Na]+ (C40H68O6Na计算值667.490 8); IR (KBr) νmax: 3 490, 2 951, 2 870, 1 704, 1 468, 1 385, 1 338, 1 268, 1 218, 1 068, 1 047, 1 013, 949, 893 cm-1; 1H NMR (CD3OD, 600 MHz) 和13C NMR (CD3OD, 150 MHz) 见表 1。
3 活性测定
3.1 抗炎活性评价
根据Griess反应[21, 22], 测定培养基中NO量的变化。将RAW264.7细胞以每孔8×104个细胞接种于96孔板, 设置对照组(DMSO)、LPS (1 μg·mL-1) 刺激组(DMSO+LPS) 和化合物干预组(DMSO+LPS+不同浓度的化合物) 三组实验。化合物的浓度分别为3.125、6.25、12.5、25和50 μmol·L-1, 药物处理时间为24 h, 以L-NMMA为对照。Griess试剂处理并测定吸光值(OD540)。采用MTT法检测定化合物对细胞活力的影响。NO生成抑制率(%) = [(LPS刺激组OD-化合物干预组OD) / (LPS刺激组OD-空白组OD)]×100%。
3.2 抗流感病毒活性评价
MDCK细胞使用DMEM培养基(含有10%胎牛血清和1%青链霉素双抗溶液), 于35 ℃、5% CO2培养箱中培养。MDCK细胞以每孔1.0×105个细胞接种于96孔板, 化合物1~12分别处理A/Puerto Rico/8/1934 (H1N1) 病毒感染的MDCK细胞, 48 h后进行抗流感病毒活性评价。以金刚烷胺作为阳性对照, CellTiter-Glo法测定其各自的荧光值[23]。IBM SPSS Statistics 20计算半数细胞毒浓度(CC50) 和半数抑制浓度(IC50)。
作者贡献: 石道群负责蜘蛛香化学成分的提取、分离、化合物结构鉴定和文章的整理; 王云对化学成分提取、分离、结构鉴定以及文章撰写提供帮助; 饶凯瑞和蒋娜分别对化合物进行抗炎和抗流感病毒活性评价; 刘丹、李蓉涛和李洪梅负责实验设计和把关、论文框架的构建及稿件修改等。
利益冲突: 本研究不存在研究者、伦理委员会成员、受试者监护人以及公开研究成果有关的利益冲突。
基金
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  • 国家自然科学基金资助项目(32060106)
  • 国家自然科学基金资助项目(31560103)
  • 云南省应用基础研究计划项目(2019FB025)
  • 昆明理工大学新型抗流感药物研发省创新团队(2019HC018)
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参考文献 引证文献
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2022年第57卷第2期
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doi: 10.16438/j.0513-4870.2021-1226
  • 接收时间：2021-08-21
  • 首发时间：2025-12-22
  • 出版时间：2022-02-12
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  • 收稿日期：2021-08-21
  • 修回日期：2021-10-09
基金
国家自然科学基金资助项目(32060106)
国家自然科学基金资助项目(31560103)
云南省应用基础研究计划项目(2019FB025)
昆明理工大学新型抗流感药物研发省创新团队(2019HC018)
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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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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