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Article(id=1210517374743220358, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210517366081975259, articleNumber=null, orderNo=null, doi=10.16438/j.0513-4870.2022-0785, pmid=null, cstr=null, oa=null, hot=null, price=null, onlineType=0, articleFormat=0, articleType=null, articleTypeStr=research-article, receivedDate=1656345600000, receivedDateStr=2022-06-28, revisedDate=1660838400000, revisedDateStr=2022-08-19, acceptedDate=null, acceptedDateStr=null, onlineDate=1766539432463, onlineDateStr=2025-12-24, pubDate=1668182400000, pubDateStr=2022-11-12, doiRegisterDate=null, doiRegisterDateStr=null, onlineIssueDate=1766539432463, onlineIssueDateStr=2025-12-24, onlineJustAcceptDate=null, onlineJustAcceptDateStr=null, onlineFirstDate=null, onlineFirstDateStr=null, sourceXml=null, magXml=null, createTime=1766539432463, creator=13701087609, updateTime=1766539432463, updator=13701087609, issue=Issue{id=1210517366081975259, tenantId=1146029695717560320, journalId=1189982191388893191, year='2022', volume='57', issue='11', pageStart='3259', pageEnd='3450', issueExtLink='null', onlineDate='null', pubDate='null', beforeIssueId=null, nextIssueId=null, price=null, status=1, issueComplete=1, articleOrder=1, issueType=-1, specialIssue=null, createTime=1766539430399, creator=13701087609, updateTime=1766539608198, updator=13701087609, preIssue=null, nextIssue=null, ext={EN=IssueExt(id=1210518111875363690, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210517366081975259, language=EN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=), CN=IssueExt(id=1210518111875363691, tenantId=1146029695717560320, journalId=1189982191388893191, issueId=1210517366081975259, language=CN, specialIssueTitle=, coverIllustrator=null, specialIssueEditor=, specialIssueAbout=)}, issueFiles=null}, startPage=3361, endPage=3364, ext={EN=ArticleExt(id=1210517375284285621, articleId=1210517374743220358, tenantId=1146029695717560320, journalId=1189982191388893191, language=EN, title=Two caryolane-type sesquiterpenoids from Pogostemon cablin (Blanco) Benth., columnId=1190335348761793317, journalTitle=Acta Pharmaceutica Sinica, columnName=Original Articles, runingTitle=null, highlight=null, articleAbstract=

By means of several chromatographic techniques, such as silica gel, Sephadex LH-20 and semi-preparative high performance liquid chromatography (HPLC), two caryolane-type sesquiterpenoids were isolated from the petroleum ether soluble fraction of the aerial parts of Pogostemon cablin (Blanco) Benth., and their structures were identified as caryolanol A (1) and 1α-ethoxy-9α-hydroxy-senecrassane (2) by various spectroscopic methods, including NMR and HR-ESI-MS. Compounds 1 and 2 were a pair of C5 epimers, and compound 1 was a new compound. In addition, the anti-influenza virus activity of compounds 1 and 2 was evaluated.

, correspAuthors=Rong-tao LI, 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=Shu-yi LI, Yu-mei FENG, Lu SU, Dan LIU, Rong-tao LI, Hong-mei LI), CN=ArticleExt(id=1210517376366416149, articleId=1210517374743220358, tenantId=1146029695717560320, journalId=1189982191388893191, language=CN, title=广藿香中的两个caryolane型倍半萜, columnId=1190335348896011050, journalTitle=药学学报, columnName=研究论文, runingTitle=null, highlight=null, articleAbstract=

采用硅胶、凝胶和高效液相色谱等色谱分离技术, 从广藿香[Pogostemon cablin (Blanco) Benth.]干燥地上部分的石油醚萃取部位中分离得到两个caryolane型倍半萜。通过核磁共振和质谱等波谱学方法, 化合物1和2的结构分别被鉴定为caryolanol A(1)和1α-ethoxy-9α-hydroxy-senecrassane(2), 其中化合物1为新化合物, 与化合物2互为C5差向异构体。此外, 对化合物1和2进行了体外抗流感病毒活性评价。

, correspAuthors=李蓉涛, 李洪梅, authorNote=null, correspAuthorsNote=
*李蓉涛, E-mail: ;
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.
175.4 s75.7 s
22.11 (ddd, 12.2, 10.4, 7.7)38.7 d2.61 (dt, 11.4, 7.2)38.9 d
31.67 (m)
1.49 (m)		36.4 t1.86 (t, 11.3)
1.51 (m)		35.3 t
435.4 s34.0 s
51.92 (ddd, 12.1, 7.8, 4.3)44.9 d1.80 (m)49.7 d
61.51 (m)
1.34 (m, )		21.0 t1.80 (m)
1.42 (m)		22.2 t
71.41 (m)
1.13 (m)		36.0 t1.51 (m)
0.97 (m)		36.1 t
839.1 s37.4 s
93.44 (overlap)72.5 d3.32 (br s)74.4 d
101.99 (m)
1.78 (m)		28.1 t1.74 (m)
1.71 (m)		26.5 t
111.70 (m)
1.63 (m)		29.3 t1.80 (m)
1.62 (m)		31.5 t
121.47 (m, 2H)41.3 t1.80 (m)
1.31 (br d, 14.0)		36.6 t
130.97 (s)20.8 q1.17 (s)28.9 q
140.99 (s)30.6 q0.91 (s)24.5 q
150.90 (s)26.8 q0.98 (s)30.2 q
1′3.46 (dq, 14.5, 7.0)
3.22 (dq, 14.5, 7.0)		57.4 t3.46 (dq, 14.4, 7.0)
3.23 (dq, 14.4, 7.0)		55.7 t
2′1.14 (t, 7.0)16.1 q1.07 (t, 7.0)16.2 q
), ArticleFig(id=1210517382888559216, tenantId=1146029695717560320, journalId=1189982191388893191, articleId=1210517374743220358, language=CN, label=Table 1, caption=

1H (600 MHz) and 13C NMR (150 MHz) data of compounds 1 and 2 (CDCl3)

, figureFileSmall=null, figureFileBig=null, tableContent=
No.12
δH (J in Hz)δC, mult.δH (J in Hz)δC, mult.
175.4 s75.7 s
22.11 (ddd, 12.2, 10.4, 7.7)38.7 d2.61 (dt, 11.4, 7.2)38.9 d
31.67 (m)
1.49 (m)		36.4 t1.86 (t, 11.3)
1.51 (m)		35.3 t
435.4 s34.0 s
51.92 (ddd, 12.1, 7.8, 4.3)44.9 d1.80 (m)49.7 d
61.51 (m)
1.34 (m, )		21.0 t1.80 (m)
1.42 (m)		22.2 t
71.41 (m)
1.13 (m)		36.0 t1.51 (m)
0.97 (m)		36.1 t
839.1 s37.4 s
93.44 (overlap)72.5 d3.32 (br s)74.4 d
101.99 (m)
1.78 (m)		28.1 t1.74 (m)
1.71 (m)		26.5 t
111.70 (m)
1.63 (m)		29.3 t1.80 (m)
1.62 (m)		31.5 t
121.47 (m, 2H)41.3 t1.80 (m)
1.31 (br d, 14.0)		36.6 t
130.97 (s)20.8 q1.17 (s)28.9 q
140.99 (s)30.6 q0.91 (s)24.5 q
150.90 (s)26.8 q0.98 (s)30.2 q
1′3.46 (dq, 14.5, 7.0)
3.22 (dq, 14.5, 7.0)		57.4 t3.46 (dq, 14.4, 7.0)
3.23 (dq, 14.4, 7.0)		55.7 t
2′1.14 (t, 7.0)16.1 q1.07 (t, 7.0)16.2 q
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广藿香中的两个caryolane型倍半萜
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李淑仪 , 冯玉梅 , 宿露 , 刘丹 , 李蓉涛 * , 李洪梅 *
药学学报 | 研究论文 2022,57(11): 3361-3364
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药学学报 | 研究论文 2022, 57(11): 3361-3364
广藿香中的两个caryolane型倍半萜
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李淑仪, 冯玉梅, 宿露, 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:

*李蓉涛, E-mail: ;
李洪梅, Tel: 86-871-65920569, E-mail:
Two caryolane-type sesquiterpenoids from Pogostemon cablin (Blanco) Benth.
Shu-yi LI, Yu-mei FENG, Lu SU, 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: 2022-11-12 doi: 10.16438/j.0513-4870.2022-0785
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摘要
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采用硅胶、凝胶和高效液相色谱等色谱分离技术, 从广藿香[Pogostemon cablin (Blanco) Benth.]干燥地上部分的石油醚萃取部位中分离得到两个caryolane型倍半萜。通过核磁共振和质谱等波谱学方法, 化合物1和2的结构分别被鉴定为caryolanol A(1)和1α-ethoxy-9α-hydroxy-senecrassane(2), 其中化合物1为新化合物, 与化合物2互为C5差向异构体。此外, 对化合物1和2进行了体外抗流感病毒活性评价。

广藿香  /  唇形科  /  倍半萜  /  caryolane  /  抗流感病毒

By means of several chromatographic techniques, such as silica gel, Sephadex LH-20 and semi-preparative high performance liquid chromatography (HPLC), two caryolane-type sesquiterpenoids were isolated from the petroleum ether soluble fraction of the aerial parts of Pogostemon cablin (Blanco) Benth., and their structures were identified as caryolanol A (1) and 1α-ethoxy-9α-hydroxy-senecrassane (2) by various spectroscopic methods, including NMR and HR-ESI-MS. Compounds 1 and 2 were a pair of C5 epimers, and compound 1 was a new compound. In addition, the anti-influenza virus activity of compounds 1 and 2 was evaluated.

Pogostemon cablin (Blanco) Benth.  /  Lamiaceae  /  sesquiterpenoid  /  caryolane  /  anti-influenza virus
李淑仪, 冯玉梅, 宿露, 刘丹, 李蓉涛, 李洪梅. 广藿香中的两个caryolane型倍半萜. 药学学报, 2022 , 57 (11) : 3361 -3364 . DOI: 10.16438/j.0513-4870.2022-0785
Shu-yi LI, Yu-mei FENG, Lu SU, Dan LIU, Rong-tao LI, Hong-mei LI. Two caryolane-type sesquiterpenoids from Pogostemon cablin (Blanco) Benth.[J]. Acta Pharmaceutica Sinica, 2022 , 57 (11) : 3361 -3364 . DOI: 10.16438/j.0513-4870.2022-0785
正文
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广藿香[Pogostemon cablin (Blanco) Benth.] 为唇形科(Lamiaceae) 刺蕊草属(Pogostemon) 植物, 其原产地是菲律宾等热带地区, 国内主要分布在广东(广州和湛江)、广西、福建和海南等地, 是“十大南药”之一[1], 具有芳香化浊、和中止呕、发表解暑等功效[2]。《中国植物志》[3]记载“梗、叶或叶供药用, 主用于孕娠呕吐、胃气痛及预防流感, 为芳香健胃、解热、镇吐剂。”据报道, 广藿香叶的甲醇提取物对流感病毒PR8具有显著的抑制作用, 在10 μg·mL-1时抑制率达到99.8%[4]。然而, 前人对广藿香的抗流感病毒活性评价和作用机制研究仅局限于其主要成分——广藿香醇, 不能全面阐明广藿香抗流感病毒作用的药效物质基础。
广藿香的化学成分种类多样, 主要有倍半萜、三萜、黄酮类和甾体等, 其中, 倍半萜类型较多, 包括愈创木烷型、广藿香醇型、桉烷型、杜松烷型、丁香烷型和caryolane型等[5-12]。为了探明广藿香中发挥抗流感病毒活性的药效物质, 本实验从广藿香地上部分石油醚萃取相中分离得到2个caryolane型倍半萜(图 1), 互为C5差向异构体, 其中化合物1是新化合物。然而, 化合物1和2均未表现出抗流感病毒活性。
结果与讨论
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1 结构鉴定
Caryolanol A (1) 为白色粉末。通过高分辨质谱HR-ESI-MS的准分子离子峰m/z 289.213 7 [M+Na]+ (计算值289.213 8, C17H30O2Na) 确定其分子式为C17H30O2, 不饱和度为3。红外光谱中3 395 cm-1的吸收峰表明该化合物结构中存在羟基。化合物1的1H NMR谱(表 1) 中可以观察到3个甲基单峰信号[δH 0.97 (3H, s, Me-13), 0.99 (3H, s, Me-14), 0.90 (3H, s, Me-15)]。另外, 1个甲基三重峰[δH 1.14 (3H, t, J = 7.0 Hz, Me-2′)] 和一对氧化的亚甲基信号[δH 3.22 (dq, J = 14.5, 7.0 Hz, Ha-1′); 3.46 (dq, J = 14.5, 7.0 Hz, Hb-1′)] 的出现, 说明结构中存在1个乙氧基, H2-1′/Me-2′之间的1H-1H COSY相关(图 2) 充分证明了这一点。除了乙氧基信号[δC 57.4 (t, C-1′) 和16.1 (q, C-2′)] 外, 化合物1的碳谱(表 1) 中可以观察到15个碳信号, 包括3个甲基, 6个亚甲基, 3个次甲基[包括1个含氧取代的次甲基δC 72.5 (d, C-9)], 1个含氧取代的叔碳[δC 75.4 (s, C-1)], 以及2个季碳。仔细对比发现, 化合物1的上述数据与一个caryolane型倍半萜caryolane-1, 9β-diol[13, 14]的数据非常相似。二者的区别在于化合物1中乙氧基的出现, 以及C-1位(δC 70.7→75.4) 和C-11位(δC 33.3→29.3) 化学位移的变化, 这说明化合物1中乙氧基取代在C-1位。HMBC谱(图 2) 中, H2-1′/C-1之间的相关峰充分证明了这一连接。另外, 低场次甲基H-9 (δH 3.44) 与C-11 (δC 29.3) 和C-12 (δC 41.3) 之间的HMBC相关, 说明C-9被羟基取代。此外, 1H-1H COSY谱中两组质子自旋偶合系统H2-3/H-2/H-5/H2-6/H2-7和H-9/H2-10/H2-11进一步证实了结构的正确性。化合物1的相对构型是通过ROESY实验确定的。ROESY谱(图 2) 中, H-2/Me-13, H-5/Me-14, H-5/H2-12, H-2/Hβ-7 (δH 1.39), 以及H-9/Hβ-7之间的NOE相关, 说明化合物1与caryolane-1, 9β-diol具有一致的相对构型。此外, H-2与H-5之间的偶合常数(J = 12.1 Hz) 也充分证实了A/B环反式稠合[14]。
化合物2的碳谱数据(表 1) 与相同溶剂(CDCl3) 中测得的1α-ethoxy-9α-hydroxy-senecrassane[15]碳谱数据几乎完全一致, 故化合物2的结构得以确定。因此, 化合物1和2是一对C5差向异构体。由于文献[15]中仅报道了1α-ethoxy-9α-hydroxy-senecrassane的几个典型氢谱数据, 故本文对该化合物的氢谱数据进行了系统归属(表 1)。
2 抗流感病毒活性评价
本实验采用流感病毒A/WSN/33/2009 (H1N1) 感染的MDCK细胞模型, 对化合物1和2进行抗流感病毒活性评价, 以nucleozin作为阳性对照。然而, 化合物1和2均未表现出明显的抗流感病毒活性。
3 讨论
本实验从广藿香地上部分的石油醚萃取相中分离鉴定了2个caryolane型倍半萜, 二者互为C5差向异构体, 其中化合物1为新化合物。抗流感病毒活性评价结果表明, 化合物1和2均未表现出明显的抗病毒活性, 这提示caryolane型倍半萜可能不是广藿香发挥抗流感病毒活性的药效物质。
Caryolane型倍半萜可能是由丁香烷(caryophyllane) 型倍半萜重排形成甲基桥而得到的[16-18], 但是丁香烯等丁香烷型倍半萜在广藿香油中的含量并不高[10, 11], 这可能是导致caryolane型倍半萜在广藿香中含量较低的原因。
实验部分
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Autopo Ⅵ全自动控温型高精度旋光仪(美国Rudolph Research Analytical公司); BrukerAvance Ⅲ HD 600 MHz核磁共振波谱仪和Bruker Tensor-27红外光谱仪(德国Bruker公司); 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-C-18反相柱(分析型: 4.6 mm × 150 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); 3111型CO2恒温培养箱(美国ThermoFisher公司); CKX41型倒置相差显微镜(日本OLYMPUS公司); Spectra Max M2多功能读板机(美国Moleccular Devices公司); 薄层析硅胶GF254、柱层析硅胶(青岛海洋化工厂); SephadexLH-20 (瑞典GE Healthcare Bio-sciences公司); ODS-C18 (75 μm) 反相填充材料(日本YMC公司); MTT、DMSO (北京Solarbio公司); 胎牛血清(美国Hyclone公司); 胰蛋白酶(瑞士Roche公司); DMEM细胞培养基(美国Invitrogen公司); nucleozin (美国MedChemExpress公司)。
药材样品于2021年4月购自昆明市新螺蛳湾药材市场, 并由昆明理工大学生命科学与技术学院陈宣钦副教授鉴定为广藿香的茎和叶, 凭证标本(KUMST20210401) 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
干燥的广藿香地上部分(25 kg) 经适当粉碎后, 在室温下用95%乙醇浸渍提取3次(每次24 h), 合并提取液, 减压浓缩回收乙醇得到浸膏。将浸膏与适量水混悬后, 依次用石油醚、乙酸乙酯和正丁醇进行萃取, 获得相应的石油醚相(650 g)、乙酸乙酯相(160 g) 和正丁醇相(215 g)。石油醚相(650 g) 利用硅胶柱色谱(80~100目硅胶715 g拌样, 200~300目硅胶3 kg装柱) 进行粗划段, 使用石油醚-丙酮梯度洗脱(10→0∶1), 经薄层色谱(TCL) 检识合并得到6段, Frs. 1~6。Fr.3 (34.11 g) 利用硅胶柱色谱, 石油醚-乙酸乙酯(100∶1→10∶1) 作为流动相进行梯度洗脱, 得到3个组分, Frs.3-1~3-3。Fr.3-3 (3.12 g) 依次经过Sphadex LH-20柱(石油醚/氯仿/甲醇5∶5∶1)、硅胶柱(石油醚/二氯甲烷2∶1→0∶1) 和Sphadex LH-20柱(石油醚/氯仿/甲醇5∶5∶1) 洗脱, 最后通过半制备HPLC (70%甲醇/水, 3 mL·min-1) 纯化, 得到化合物1 (6.5 mg) 和2 (8.2 mg)。
2 结构鉴定
化合物1  白色粉末, [α]$ {}_{\mathrm{D}}^{21} $ +4.44 (c 0.18, MeOH); HR-ESI-MS (pos.): m/z 289.213 7 [M+Na]+ (C17H30O2Na, 计算值289.213 8); IR (KBr) νmax: 3 395, 2 972, 2 936, 2 882, 1 629, 1 470, 1 388, 1 322, 1 095, 1 077, 1 040, 1 011, 966, 945, 637, 580 cm-1; 1H NMR (CDCl3, 600 MHz) 和13C NMR (CDCl3, 150 MHz) 见表 1。
化合物2  白色粉末, [α]$ {}_{\mathrm{D}}^{25} $ -34.00 (c 0.13, MeOH); 1H NMR (CDCl3, 600 MHz) 和13C NMR (CDCl3, 150 MHz) 见表 1。
3 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1.0×105个/孔接种于96孔板, 化合物1和2分别使用病毒A/WSN/33/2009 (H1N1) 感染的MDCK细胞, 48 h后进行抗流感病毒活性评价。以nucleozin作为阳性对照, Cell Titer-Glo法测定其各自的荧光值。
作者贡献: 李淑仪负责广藿香化学成分的提取分离、化合物结构鉴定和文章的撰写; 冯玉梅协助进行广藿香化学成分的分离纯化; 宿露负责抗流感病毒活性评价; 刘丹、李蓉涛和李洪梅负责实验的设计和论文框架的构建; 李洪梅负责稿件的修改。
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)
  • 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11期
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doi: 10.16438/j.0513-4870.2022-0785
  • 接收时间：2022-06-28
  • 首发时间：2025-12-24
  • 出版时间：2022-11-12
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  • 收稿日期：2022-06-28
  • 修回日期：2022-08-19
基金
国家自然科学基金资助项目(32060106)
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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*李蓉涛, E-mail: ;
李洪梅, Tel: 86-871-65920569, 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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