四种旋覆花属植物的化学成分及生物活性研究
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摘要
菊科(Compositae)旋覆花属(Inula L.)植物约有100种，主要分布于地中海地区，在欧洲、非洲及亚洲的其它地区也有分布。本属植物在我国有20余种和多数变种，进一步分为5组11系，其中部分为广布种，部分为特有种。我国过半的旋覆花属植物有药用记载。2010版中国药典收录的3味中药材，土木香、旋覆花及金沸草来源于本属的4种植物。对旋覆花属植物化学成分、药理活性的综述，以及本课题组的前期研究表明，本属植物富含的倍半萜类成分具有母核骨架多样、手性中心复杂、取代基团简单的特点；同时，倍半萜类成分显示出广泛的生物活性，特别是具有突出的抗炎和抗肿瘤活性。本课题选取了四种旋覆花属植物，喜马拉雅地区特有的西藏旋覆花(I. falconeri)、锈毛旋覆花(I. hookeri)、云南特有的绢叶旋覆花(I. sericophylla)和滇南羊耳菊(I. wissmanniana),进行植物化学和生物活性研究。而此前，它们的相关报道寥寥。
采用各种现代分离纯化技术和鉴定手段对西藏旋覆花、锈毛旋覆花和滇南羊耳菊植物中富含倍半萜类成分的二氯甲烷部位或乙酸乙酯部位，以及含有少量倍半萜类成分的石油醚部位进行了系统性的化学分离和鉴定。除去共有成分及未鉴定成分，最终分离解析了178个化合物，新化合物43个。这些化合物主要包括了84个倍半萜、7个倍半萜二聚体、12个单萜、以及包括黄酮(20个)、木脂素(7个)、脱辅基类胡萝卜素(6个)等在内的75个其它类化合物。另外，基于绢叶旋覆花和锈毛旋覆花化学成分的相似性，采用HPLC/DAD/ESI-MSn分析了绢叶旋覆花的化学成分，分析鉴定了36个萜类成分。
分离鉴定的倍半萜类化合物包含9种不同的碳骨架，以吉玛烷型、苍耳烷型、愈创木烷型、伪愈创木烷型和桉叶烷型为主。在本课题研究中，我们发现了愈创木烷1(2),4(5)双烯体的生源近似化合物(IF-16和IF-17),同时发现了7个罕见的愈创木烷2,4连接型倍半萜二聚体(IF-43IF-49),其中3个为同一Diels-Alder反应的异构体产物，完美体现了DA反应的区域选择性和立体选择性。我们发现了5,6裂环桉叶烷重排型新骨架倍半萜(IW-26IW-28),以及自然界中首例C17伪愈创木烷衍生型倍半萜内酯(IF-41IF-44)和3,4裂环桉叶烷型倍半萜(IW-25)。另外发现了本属首例桉叶烷型倍半萜六元内酯(IW-19),4,5裂环桉叶烷型倍半萜六元内酯(IW-24),4,5裂环丁香烷型倍半萜(IF-50)和1,10裂环愈创木烷(chromolaevane)型倍半萜内酯(IF-37)。
参考前人的理论研究和实验结果，我们分别推测了西藏旋覆花中倍半萜和二聚倍半萜的生源途径(网络)，锈毛旋覆花中C17伪愈创木烷衍生型倍半萜可能的生源途径，滇南羊耳菊中桉叶烷型倍半萜的3种裂环方式和环己双烯醇的3种重排方式，并分别进行了初步的IRC反应路径计算和化学反应验证。
在阐明化学成分的基础上，结合HPLC/DAD指纹图谱及数据的PCA处理，讨论了旋覆花组7种草本植物的相互亲缘关系。根据分析结果，我们建议重新考量金沸草的入药基源。分析结果也支持了“旋覆花和线叶旋覆花是欧亚旋覆花的变种或亚种”的观点，并提出“湖北旋覆花、水朝阳旋覆花、绢叶旋覆花和锈毛旋覆花可能由欧亚旋覆花进化而来”的观点。
在LPS诱导的巨噬细胞RAW264.7模型中，我们发现愈创木烷型倍半萜内酯IF-17(IC50,0.22M), IF-24(0.11M), IF-26(0.29M), IF-27(0.13M)；伪愈创木烷型倍半萜内酯IF-28(0.07M), IH-31(0.29M), IH-37(0.28M), IH-40(0.38M)；桉叶烷型倍半萜内酯IF-40(0.11M)以及桉叶烷衍生型倍半萜内酯IW-26(0.38M)表现出强于或近似于阳性药的NO代谢抑制活性，并进一步讨论了化合物骨架类型、脂溶性、取代基团、结构刚性等对NO生成抑制活性的影响。
采用CCK-8法，体外筛选了倍半萜和二聚倍半萜的肿瘤细胞抑制活性，发现吉玛烷型倍半萜内酯和愈创木烷2,4连接型倍半萜二聚体，普遍对HepG2, PC-3和MGC-803细胞具有较强的抑制作用，而对HeLa细胞毒性不明显。二聚倍半萜IF-45和新颖骨架化合物IW-26对HepG2, PC-3和MGC-803肿瘤细胞生长抑制的IC50值分别为0.961.66和1.353.35M。
The Inula genus, which comprises ca.100species of the Compositae family, isdistributed throughout Asia, Europe, and Africa and can be found predominantly inthe Mediterranean. More than20Inula species are distributed in China and furtherdivided into five sections and11series in phytotaxonomy. A number of plants fromthe Inula genus are used as traditional herbal medicines throughout the world,especially in China. In the latest Chinese Pharmacopoeia, three Traditional ChineseMedicines that are used as expectorants, antitussives, diaphoretics, antiemetics, andbactericides Tumuxiang, Xuanfuhua, and Jinfeicao originate from four Inulaplants. Inula species have emerged as exceptionally rich sources of varioussesquiterpenoids, which accounted for anti-inflammatory, anti-proliferation,antibacterial, and hepatoprotective properties. In continuation of our research programfor bioactive sesquiterpenoids derived from the plants of Inula genus, we examined I.falconeri, I. hookeri, I. sericophylla, and I. wissmanniana, on which extensivephytochemical studies have not been previously conducted.
178compounds were isolated from the whole plants of I. falconeri, I. hookeri,and I. wissmanniana via detailed phytochemical investigations with variouschromatographic techniques. The structures were elucidated by spectroscopic analysisto be84sesquiterpenes, seven dimeric sesquiterpenes,12monoterpenes, and75othercompounds which included20flavonoids,7lignans,6apocarotenoids, etc.Considering the great HPLC/DAD similarity between the crude extracts of I.sericophylla and I. hookeri, HPLC/DAD/ESI-MSnwas applied to analyse thesecondary metabolites from I. sericophylla, affording36terpenoids.
The84sesquiterpenes comprised35new sesquiterpenoids and49knownsesquiterpene lactones which included nine defferent frameworks, mainly germacrane,xanthane, guaiane, pseudoguaiane, and eudesmane. Seven rare guaiane2,4-typeddimeric sesquiterpene lactones (IF-43IF-49), which three of them were structurallyequivalent to stereoselective and regioselective adducts of the same Diels-Alderreaction, together with biosynthetic analogues of1(2),4(5)-guaia-dienes (IF-16andIF-17) were obtained from I. falconeri, a plant endemic to the Himalayas. The firstnaturally occurring5,6-seco-and rearranged eudesmane sesquiterpenoids(IW-26IW-28), unprecedented C17-pseudoguaianolides (IF-41IF-44), and novel3,4-seco-eudesmane sesquiterpenoids (IW-25) were herein described. A survey ofliteratures also showed the new compounds IW-19, IW-24, and IF-50and knowncompound IF-37to be the first occurrence of eudesman-12,5-olide,4,5-seco-eudesman-12,5-olide,4,5-seco-caryophyllane derivative, chromolaevan-12,8-olide,respectively, from the plants of Inula genus.
On the basis of theoretical and experimental reports, the biosynthetic pathwaysof novel secondary metabolites, including dimeric sesquiterpenes (IF-43IF-45),C17-pseudoguaianolides (IF-41IF-44), and eudesmane-derivatived sesquiterpenes(IW-21IW-23) were hypothesized in this study.
On the basis of phytochemical investigations, the chemotaxonomic significanceof sesquiterpenes from seven Inula herbs were discussed via HPLC/DAD detectionfollowed by principal component analysis. Our experimental study supported the viewthat I. japonica Thunb. and I. lineariaefolia Turcz. were variants or subspecies of I.britanica L.. We also further suspected that I. hupehensis Ling, I. helianthus-aquaticaC. Y. Wu ex Ling, I. sericophylla Franch, and I. hookeri C. B. Clarke were evolvedfrom I. britanica L.. Considering the differences of chemical constituents between I.japonica Thunb. and I. lineariaefolia Turcz., the application of I. lineariaefolia Turcz.as Jinfeicao should be reconsidered.
All the isolated sesquiterpenes and dimeric sesquiterpenes were assessed for theirinhibitory effects against LPS-induced NO production in RAW264.7macrophages.The guaianolides IF-17(IC50,0.22M), IF-24(IC50,0.11M), IF-26(0.29M), and IF-27(0.13M), pseudoguaianolides IF-28(0.07M), IH-31(0.29M), IH-37(0.28M), and IH-40(0.38M), eudesmanolide IF-40(0.11M), andeudesmane-derivatived sesquiterpene IW-26(0.38M) showed remarkable inhibitoryactivities, comparing with the positive control. These studies also led to a betterunderstanding of the structure-activity relationships from frameworks, lipophilicities,substituted groups, and structural rigidness for the sesquiterpenes.
All the sesquiterpenes and dimeric sesquiterpenes were assessed for theircytotoxic activities against HepG2, HeLa, PC-3, and MGC-803cell lines by CCK-8assay. Some of the isolates, especiallly germacranolides and dimeric sesquiterpenesexhibited significant cytotoxicities against HepG2, PC-3, and MGC-803cells. Thedimeric sesquiterpene IF-45and novel eudesmane-derivatived sesquiterpene IW-26inhibited HepG2, PC-3, and MGC-803cells with IC50values at0.961.66and1.353.35M, respectively.
采用各种现代分离纯化技术和鉴定手段对西藏旋覆花、锈毛旋覆花和滇南羊耳菊植物中富含倍半萜类成分的二氯甲烷部位或乙酸乙酯部位，以及含有少量倍半萜类成分的石油醚部位进行了系统性的化学分离和鉴定。除去共有成分及未鉴定成分，最终分离解析了178个化合物，新化合物43个。这些化合物主要包括了84个倍半萜、7个倍半萜二聚体、12个单萜、以及包括黄酮(20个)、木脂素(7个)、脱辅基类胡萝卜素(6个)等在内的75个其它类化合物。另外，基于绢叶旋覆花和锈毛旋覆花化学成分的相似性，采用HPLC/DAD/ESI-MSn分析了绢叶旋覆花的化学成分，分析鉴定了36个萜类成分。
分离鉴定的倍半萜类化合物包含9种不同的碳骨架，以吉玛烷型、苍耳烷型、愈创木烷型、伪愈创木烷型和桉叶烷型为主。在本课题研究中，我们发现了愈创木烷1(2),4(5)双烯体的生源近似化合物(IF-16和IF-17),同时发现了7个罕见的愈创木烷2,4连接型倍半萜二聚体(IF-43IF-49),其中3个为同一Diels-Alder反应的异构体产物，完美体现了DA反应的区域选择性和立体选择性。我们发现了5,6裂环桉叶烷重排型新骨架倍半萜(IW-26IW-28),以及自然界中首例C17伪愈创木烷衍生型倍半萜内酯(IF-41IF-44)和3,4裂环桉叶烷型倍半萜(IW-25)。另外发现了本属首例桉叶烷型倍半萜六元内酯(IW-19),4,5裂环桉叶烷型倍半萜六元内酯(IW-24),4,5裂环丁香烷型倍半萜(IF-50)和1,10裂环愈创木烷(chromolaevane)型倍半萜内酯(IF-37)。
参考前人的理论研究和实验结果，我们分别推测了西藏旋覆花中倍半萜和二聚倍半萜的生源途径(网络)，锈毛旋覆花中C17伪愈创木烷衍生型倍半萜可能的生源途径，滇南羊耳菊中桉叶烷型倍半萜的3种裂环方式和环己双烯醇的3种重排方式，并分别进行了初步的IRC反应路径计算和化学反应验证。
在阐明化学成分的基础上，结合HPLC/DAD指纹图谱及数据的PCA处理，讨论了旋覆花组7种草本植物的相互亲缘关系。根据分析结果，我们建议重新考量金沸草的入药基源。分析结果也支持了“旋覆花和线叶旋覆花是欧亚旋覆花的变种或亚种”的观点，并提出“湖北旋覆花、水朝阳旋覆花、绢叶旋覆花和锈毛旋覆花可能由欧亚旋覆花进化而来”的观点。
在LPS诱导的巨噬细胞RAW264.7模型中，我们发现愈创木烷型倍半萜内酯IF-17(IC50,0.22M), IF-24(0.11M), IF-26(0.29M), IF-27(0.13M)；伪愈创木烷型倍半萜内酯IF-28(0.07M), IH-31(0.29M), IH-37(0.28M), IH-40(0.38M)；桉叶烷型倍半萜内酯IF-40(0.11M)以及桉叶烷衍生型倍半萜内酯IW-26(0.38M)表现出强于或近似于阳性药的NO代谢抑制活性，并进一步讨论了化合物骨架类型、脂溶性、取代基团、结构刚性等对NO生成抑制活性的影响。
采用CCK-8法，体外筛选了倍半萜和二聚倍半萜的肿瘤细胞抑制活性，发现吉玛烷型倍半萜内酯和愈创木烷2,4连接型倍半萜二聚体，普遍对HepG2, PC-3和MGC-803细胞具有较强的抑制作用，而对HeLa细胞毒性不明显。二聚倍半萜IF-45和新颖骨架化合物IW-26对HepG2, PC-3和MGC-803肿瘤细胞生长抑制的IC50值分别为0.961.66和1.353.35M。
The Inula genus, which comprises ca.100species of the Compositae family, isdistributed throughout Asia, Europe, and Africa and can be found predominantly inthe Mediterranean. More than20Inula species are distributed in China and furtherdivided into five sections and11series in phytotaxonomy. A number of plants fromthe Inula genus are used as traditional herbal medicines throughout the world,especially in China. In the latest Chinese Pharmacopoeia, three Traditional ChineseMedicines that are used as expectorants, antitussives, diaphoretics, antiemetics, andbactericides Tumuxiang, Xuanfuhua, and Jinfeicao originate from four Inulaplants. Inula species have emerged as exceptionally rich sources of varioussesquiterpenoids, which accounted for anti-inflammatory, anti-proliferation,antibacterial, and hepatoprotective properties. In continuation of our research programfor bioactive sesquiterpenoids derived from the plants of Inula genus, we examined I.falconeri, I. hookeri, I. sericophylla, and I. wissmanniana, on which extensivephytochemical studies have not been previously conducted.
178compounds were isolated from the whole plants of I. falconeri, I. hookeri,and I. wissmanniana via detailed phytochemical investigations with variouschromatographic techniques. The structures were elucidated by spectroscopic analysisto be84sesquiterpenes, seven dimeric sesquiterpenes,12monoterpenes, and75othercompounds which included20flavonoids,7lignans,6apocarotenoids, etc.Considering the great HPLC/DAD similarity between the crude extracts of I.sericophylla and I. hookeri, HPLC/DAD/ESI-MSnwas applied to analyse thesecondary metabolites from I. sericophylla, affording36terpenoids.
The84sesquiterpenes comprised35new sesquiterpenoids and49knownsesquiterpene lactones which included nine defferent frameworks, mainly germacrane,xanthane, guaiane, pseudoguaiane, and eudesmane. Seven rare guaiane2,4-typeddimeric sesquiterpene lactones (IF-43IF-49), which three of them were structurallyequivalent to stereoselective and regioselective adducts of the same Diels-Alderreaction, together with biosynthetic analogues of1(2),4(5)-guaia-dienes (IF-16andIF-17) were obtained from I. falconeri, a plant endemic to the Himalayas. The firstnaturally occurring5,6-seco-and rearranged eudesmane sesquiterpenoids(IW-26IW-28), unprecedented C17-pseudoguaianolides (IF-41IF-44), and novel3,4-seco-eudesmane sesquiterpenoids (IW-25) were herein described. A survey ofliteratures also showed the new compounds IW-19, IW-24, and IF-50and knowncompound IF-37to be the first occurrence of eudesman-12,5-olide,4,5-seco-eudesman-12,5-olide,4,5-seco-caryophyllane derivative, chromolaevan-12,8-olide,respectively, from the plants of Inula genus.
On the basis of theoretical and experimental reports, the biosynthetic pathwaysof novel secondary metabolites, including dimeric sesquiterpenes (IF-43IF-45),C17-pseudoguaianolides (IF-41IF-44), and eudesmane-derivatived sesquiterpenes(IW-21IW-23) were hypothesized in this study.
On the basis of phytochemical investigations, the chemotaxonomic significanceof sesquiterpenes from seven Inula herbs were discussed via HPLC/DAD detectionfollowed by principal component analysis. Our experimental study supported the viewthat I. japonica Thunb. and I. lineariaefolia Turcz. were variants or subspecies of I.britanica L.. We also further suspected that I. hupehensis Ling, I. helianthus-aquaticaC. Y. Wu ex Ling, I. sericophylla Franch, and I. hookeri C. B. Clarke were evolvedfrom I. britanica L.. Considering the differences of chemical constituents between I.japonica Thunb. and I. lineariaefolia Turcz., the application of I. lineariaefolia Turcz.as Jinfeicao should be reconsidered.
All the isolated sesquiterpenes and dimeric sesquiterpenes were assessed for theirinhibitory effects against LPS-induced NO production in RAW264.7macrophages.The guaianolides IF-17(IC50,0.22M), IF-24(IC50,0.11M), IF-26(0.29M), and IF-27(0.13M), pseudoguaianolides IF-28(0.07M), IH-31(0.29M), IH-37(0.28M), and IH-40(0.38M), eudesmanolide IF-40(0.11M), andeudesmane-derivatived sesquiterpene IW-26(0.38M) showed remarkable inhibitoryactivities, comparing with the positive control. These studies also led to a betterunderstanding of the structure-activity relationships from frameworks, lipophilicities,substituted groups, and structural rigidness for the sesquiterpenes.
All the sesquiterpenes and dimeric sesquiterpenes were assessed for theircytotoxic activities against HepG2, HeLa, PC-3, and MGC-803cell lines by CCK-8assay. Some of the isolates, especiallly germacranolides and dimeric sesquiterpenesexhibited significant cytotoxicities against HepG2, PC-3, and MGC-803cells. Thedimeric sesquiterpene IF-45and novel eudesmane-derivatived sesquiterpene IW-26inhibited HepG2, PC-3, and MGC-803cells with IC50values at0.961.66and1.353.35M, respectively.
引文
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