中国金粟兰科植物药用亲缘学研究
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摘要
金粟兰科(Chloranthaceae)植物属于基底植物类群,对于理解被子植物的起源、演化和扩散可能具有特殊意义。该科植物全球共四属,草珊瑚属(Sarcandra)、金粟兰属(Chloranthus)、雪香兰属(Hedyosmum)和Ascarina属,约70种,主要分布于热带和温带,其中三属约16种在我国有分布。大部分植物的全草或根供药用,民间用做于消肿镇痛、跌打损伤、疮疖肿毒等。本文在综述了金粟兰科的系统分类学、地理分布、传统疗效、化学成分和药理活性研究情况的基础上,对本科植物进行药用亲缘学研究。
海南草珊瑚(Sarcandra hainanensis)为我国特有种,在我国民间应用已久但化学成分及药理活性研究尚属空白。我们以其化学成分和药理活性研究作为药用亲缘学的切入点。在系统分离的基础上,对海南草珊瑚的主要成分和特征成分进行含量测定,以此探讨其药用开发价值;通过与草珊瑚进行化学成分比较,考证海南草珊瑚作为草珊瑚代用的可能性,并为海南草珊瑚的分类学地位提供化学依据;在此基础上比较我国草珊瑚属植物与其它两属植物在化学成分和药理作用方面的异同,从而对这一植物类群的药用亲缘学进行初步探索。
采用多种现代色谱技术对海南草珊瑚的化学成分进行系统分离研究。从海南草珊瑚95%乙醇提取物的各部位中共分离得到化合物43个,利用多种谱学手段鉴定了36个化合物的结构,包括黄酮及其衍生物18个;有机酸及其衍生物12个;蒽醌2个;香豆素1个;萜类1个;甾体类2个。以上化合物全部是首次从该植物中分得,6个为新化合物,20个为本属首次报道,18个为本科首次报道。
新化合物依次分别定名为sarcandrones A-F(15-18,5,6),已知化合物分别鉴定为2',3'-二羟基-4',6'-二甲氧基查耳酮(1)、2'-羟基-4',5'-二甲氧基查耳酮(2)、cardamonin(3)、boesenbergin B(4)、7-羟基-5,6-二甲氧基二氢黄酮(7)、7-羟基-5-甲氧基二氢黄酮(8)、7-羟基-5,8-二甲氧基二氢黄酮(9)、柚皮素-4',7-二甲醚(10)、异美五针松二氢黄酮(11)、3,4',5,7-四羟基二氢黄酮-3-O-葡萄糖(12)、山柰酚(13)、山柰酚-3-O-葡萄糖(14)、棕榈酸(22)、花生酸(23)、硬脂酸(24)、反式-3-羟基-4甲氧基肉桂醛(25)、2,6-二羟基-3,5-二甲氧基苯甲醛(26)、咖啡酸(27)、迷迭香酸(28)、迷迭香酸甲酯(29)、迷迭香酸乙酯(30)、3,4-二羟基-苯乙醇(31)、3,4-二羟基-苯乙醇-1-O-葡萄糖(32)、(3,4,6-三羟基-苯基)-乙醇1-O-半乳糖(33);4-羟基-3-O-葡萄糖-苯基乙醇(34)、大黄素(19)、大黄酚(20)、异嗪皮啶(21)、9,19-环阿尔廷烷-24-烯-3-醇(10)、β-谷甾醇(35)和胡萝卜苷(36)。
在化学成分系统分离的基础上,首次采用高效液相色谱法对海南草珊瑚中的四个主要化学成分进行了含量测定,它们在原药材中的含量分别为2'-羟基-4',5'-二甲氧基查耳酮(2)1.2555 mg/g、7-羟基-5,6-二甲氧基二氢黄酮(7)0.4687 mg/g、异嗪皮啶(21)0.2248 mg/g、迷迭香酸(28)0.5290 mg/g。在此基础上,考察了这四个成分在我国金粟兰科植物中的分布情况,并对其进行了定性定量。采用LC-MS的MRM扫描方式,以553.2/383.0和553.2/289.0作为检测离子对,考察了双黄酮类微量成分(15-17)在我国金粟兰科植物中的分布情况。
对海南草珊瑚中分离得到的部分化合物进行了抗肿瘤、抗HIV整合酶体外抑制活性筛选。抗肿瘤试验选用的细胞株包括包括肺腺癌细胞株(A549,H322M,H157,H358,Hop62和H1792)、乳腺癌细胞株(T47D和MCF7)及白血病细胞株K_(562),对含量较大的查耳酮(2、3)、二氢黄酮(7)、异嗪皮啶(21)和特征双黄酮(15)进行了活性筛选,发现查耳酮(2、3)和双黄酮(15)对所测试非小细胞肺癌和乳腺癌具有良好的抑制效果,所筛选化合物(1、2、3、7、8、21)对白血病细胞株均未表现出活性;双黄酮类成分(15、16)在HIV整合酶体外抑制试验中呈现弱活性。
对海南草珊瑚95%乙醇粗提物和各部位以及我国金粟兰科八个有代表性植物的水提物和甲醇提取物进行了抗菌筛选。选用的菌株包括革兰氏阳性菌菌株(金黄色葡萄球菌)和阴性菌菌株(痢疾杆菌、绿脓杆菌、大肠杆菌)。对比海南草珊瑚的各部位,乙酸乙酯和水部位对金黄色葡萄球菌有效;在所测试的八个植物的两种提取物中,甲醇提取物的活性优于水提物;比较不同植物的甲醇提取物,丝穗金粟兰对四种菌株均有效,海南草珊瑚对金黄色葡萄球菌和痢疾杆菌有效、草珊瑚对金黄色葡萄球菌有效,及已对大肠杆菌有效。
总结上述研究结果,得到以下结论。从化学分类学角度看,海南草珊瑚的化学成分不同于草珊瑚,支持其作为分类学意义上的种存在;草珊瑚属植物的化学成分在大极性部位相近,中小极性成分各有差异;金粟兰属植物与草珊瑚属植物的主要成分接近,但含量差异较大并且存在一些特征的含量较小的化学成分,亲缘关系较近;雪香兰属植物雪香兰的化学成分与其余两属差异最大,亲缘关系最远。从药用资源开发的角度来看,现有的研究结果不支持海南草珊瑚作为草珊瑚代用,但海南草珊瑚有独特的活性成分,可以考虑对其进行相关开发利用;金粟兰属植物属间个体差异较大,采用时应慎重;雪香兰属植物可能不具有与其它金粟兰科植物相似的药用价值。
Chloranthaceae is a small family of four genera,i.e.,Sarcandra,Chloranthus, Hedyosmum and Ascarina,and ca.70 species occurring in tropical and subtropical areas. Three Genera and 16 species are distributed in the southern part of China.The whole plants or roots of plants in this family are widely used in folk medicine as antispasmodic, antiseptic,and anticancer drugs,or for relieving ache,boils,and dermatopathia in eastern Asia.Reviewed the previous studies of the family Chloranthaceae including distribution, traditional usage,chemical constituents and bioactivities,we choose the family of Chloranthaceae as an objective of our pharmacophylogenetic investigation.S. hainanensis,a shrub distributing only in the south of China,is widely used to invigorate blood circulation and eliminate blood-stasis as traditional Chinese medicine.However,to the best of our knowledge,there was no phytochemical and pharmacological report about S.hainanensis.So we initiated an investigation on the chemical constituents and bioactivities of S.hainanensis with the purpose to study the chemical constituents and differentiate S.hainanensis from S.glabra and better understand the chemotaxonomic relationship of the family of Chloranthaceae.
Kinds of chromatographic methods were employed to isolate and purify compounds from Sarcandra hainanensis.43 Compounds were isolated from the 95%ethanol extract of S.hainanensis.The structures of 36 compounds were identified by combination of spectroscopic strategies,including 18 flavanoid and derivates,12 organic acids and derivates,2 anthraquinones,1 coumarin,1 triterpenoids and 2 sterols.All the compounds were isolated from the title plant for the first time.6 compounds of them were new compounds,20 were isolated from genus Sarcandra for the first time and 18 were reported from the family of Chloranthaceae for the first time.
The six new compounds were named as sarcandrones A - F(15-18,5,6).Structures of the known compounds were identified as 2',3'-hydroxy-4',6'-dimethoxychalcone(1), 2'-hydroxy-4',5'-dimethoxychalcone(2),cardamonin(3),boesenbergin B(4),7-hydroxy -5,6-dimethoxyflavanone(7),7-hydroxy-5-methoxyflavanone(8),7-hydroxy-5,8 -dimethoxyflavanone(9),naringenin-4',7-dimethylether(10),pinostrobin(11), 3,4',5,7-tetra-hydroxyflavanone-3-O-glucoside(12),kaempferol(13),kaempferol 3-O-glucoside(14),palmitic acid(22),icosanoic acid(23),ctadecanoic acid(24), (E)-3-hydroxy-4-methoxycinnamal-dehydeacrylaldehyde(25),2,6-dihydroxy -3,5-dimethoxy-benzaldehyde(26),caffeic acid(27),rosmarinate acid(28),methyl rosmarinate(29),ethyl rosmarinate(30),3,4-dihydroxyl-phenyl-ethanol(31), (3,4-dihydroxyl-phenyl)-ethanol-O-galactoside(32)(3,4,6-trihydroxyl-phenyl)-ethanol -O-galactoside(33),acidchrysophanol(19),emodin(20),isofraxidin(21), 9,19-Cycloarta-24-en-3-ol(34),13-sitosterol(35) and daucosterin(36).
A proper chromatographic pattern for S.hainanensis based on high performance liquid chromatography coupled with diode-array detector(HPLC-DAD) was developed for the first time.Four main characteristic constituents of S.hainanensis were assayed as 2'-hydroxy-4',5'-dimethoxychalcone(2) 1.2555 mg/g,7-hydroxy-5,6-dimethoxy -flavanone(7) 0.4687 mg/g,isofraxidin(21) 0.2248 mg/g,rosmarinate acid(28) 0.5290 mg/g,respectively.The chromatographic pattern was also employed for screening the four constitunents in the 13 species of Chloranthaceae.The amounts of the constituents exited in different plants were assayed,respectively.
A MRM analytical method with LC-MS was established for screening the new biflavanoids(15-17) with trace amounts in the plants of Chloranthaceae.The result provided scientific evidences to the differnences between the constituents of S. hainanensis and that of S.glabra.
Characteristic compounds(2,3,7,15,21) isolated from S.hainanensis were detected for their bioactivities against non-small lungcancer cell lines A549,H322M,H157,H358, Hop62,H1792 and breast carcinoma cell lines T47D,MCF7.The chalcones(2,3) and biflavanoids(15) tested could significantly inhibit the survival of the above cell lines. Compounds 15 and 16 were assayed for their HIV-1 integrase inhibition activities with a microplate screening method using magnetic beads.They showed weak activities for the integrase strand transfer reaction.
The different portions of S.hainanensis as well as the water and MeOH extracts of 8 different plants of Chloranthaceae were assayed for their antibacterial activity.A Gram-positive bacteria(Staphylococcus aureus) and Gram-negative bacteria(Bacillus dysenteriae,Bacillus aeruginosus and Bacillus coli) were used.In the four different portions of S.hainanensis,EtOAc and H_2O portions were active to Staphylococcus aureus. Compared the two kinds of extrats,the MeOH extracts were more active than the H_2O ones.Among the MeOH of the 8 plants tested,Chloranthus fortunei was active to the four bacterias,S.hainanensis was active to S.aureus and Bacillus dysenteriae,S.glabra was active Staphylococcus aureus and C.serratus was active to Bacillus aeruginosus.
The results of this thesis may support the view of S.hainanensis as an independent species since its chemical profile was different from that of S.glabra.The standards with different contents in the plants of Chloranthus were determined while almost no standard was detected in the only spices of Hedyosmum.The chemotaxonomic relationship between the three genera of Chloranthaceae in China may be deduced as the species of Chloranthus having a close affinity with Sarcandra and Hedyosmum being the sister group of Sarcandra and Chloranthus according to the characteristics of chemical constituents.
In the view of the medical usage,S.hainanensis was not suitable to be used as a succedaneum of S.glabra.However,the special biological activities of S.hainanensis suggested it may be potential as a natural source of antitumor compounds.Since the species of Chloranthus were different from each other by their chemical constituents, they should be used carefully when used as folk medicine.The plants of genus Hedyosmum in China may not have the same action as S.glabra and S.hainanensis.
海南草珊瑚(Sarcandra hainanensis)为我国特有种,在我国民间应用已久但化学成分及药理活性研究尚属空白。我们以其化学成分和药理活性研究作为药用亲缘学的切入点。在系统分离的基础上,对海南草珊瑚的主要成分和特征成分进行含量测定,以此探讨其药用开发价值;通过与草珊瑚进行化学成分比较,考证海南草珊瑚作为草珊瑚代用的可能性,并为海南草珊瑚的分类学地位提供化学依据;在此基础上比较我国草珊瑚属植物与其它两属植物在化学成分和药理作用方面的异同,从而对这一植物类群的药用亲缘学进行初步探索。
采用多种现代色谱技术对海南草珊瑚的化学成分进行系统分离研究。从海南草珊瑚95%乙醇提取物的各部位中共分离得到化合物43个,利用多种谱学手段鉴定了36个化合物的结构,包括黄酮及其衍生物18个;有机酸及其衍生物12个;蒽醌2个;香豆素1个;萜类1个;甾体类2个。以上化合物全部是首次从该植物中分得,6个为新化合物,20个为本属首次报道,18个为本科首次报道。
新化合物依次分别定名为sarcandrones A-F(15-18,5,6),已知化合物分别鉴定为2',3'-二羟基-4',6'-二甲氧基查耳酮(1)、2'-羟基-4',5'-二甲氧基查耳酮(2)、cardamonin(3)、boesenbergin B(4)、7-羟基-5,6-二甲氧基二氢黄酮(7)、7-羟基-5-甲氧基二氢黄酮(8)、7-羟基-5,8-二甲氧基二氢黄酮(9)、柚皮素-4',7-二甲醚(10)、异美五针松二氢黄酮(11)、3,4',5,7-四羟基二氢黄酮-3-O-葡萄糖(12)、山柰酚(13)、山柰酚-3-O-葡萄糖(14)、棕榈酸(22)、花生酸(23)、硬脂酸(24)、反式-3-羟基-4甲氧基肉桂醛(25)、2,6-二羟基-3,5-二甲氧基苯甲醛(26)、咖啡酸(27)、迷迭香酸(28)、迷迭香酸甲酯(29)、迷迭香酸乙酯(30)、3,4-二羟基-苯乙醇(31)、3,4-二羟基-苯乙醇-1-O-葡萄糖(32)、(3,4,6-三羟基-苯基)-乙醇1-O-半乳糖(33);4-羟基-3-O-葡萄糖-苯基乙醇(34)、大黄素(19)、大黄酚(20)、异嗪皮啶(21)、9,19-环阿尔廷烷-24-烯-3-醇(10)、β-谷甾醇(35)和胡萝卜苷(36)。
在化学成分系统分离的基础上,首次采用高效液相色谱法对海南草珊瑚中的四个主要化学成分进行了含量测定,它们在原药材中的含量分别为2'-羟基-4',5'-二甲氧基查耳酮(2)1.2555 mg/g、7-羟基-5,6-二甲氧基二氢黄酮(7)0.4687 mg/g、异嗪皮啶(21)0.2248 mg/g、迷迭香酸(28)0.5290 mg/g。在此基础上,考察了这四个成分在我国金粟兰科植物中的分布情况,并对其进行了定性定量。采用LC-MS的MRM扫描方式,以553.2/383.0和553.2/289.0作为检测离子对,考察了双黄酮类微量成分(15-17)在我国金粟兰科植物中的分布情况。
对海南草珊瑚中分离得到的部分化合物进行了抗肿瘤、抗HIV整合酶体外抑制活性筛选。抗肿瘤试验选用的细胞株包括包括肺腺癌细胞株(A549,H322M,H157,H358,Hop62和H1792)、乳腺癌细胞株(T47D和MCF7)及白血病细胞株K_(562),对含量较大的查耳酮(2、3)、二氢黄酮(7)、异嗪皮啶(21)和特征双黄酮(15)进行了活性筛选,发现查耳酮(2、3)和双黄酮(15)对所测试非小细胞肺癌和乳腺癌具有良好的抑制效果,所筛选化合物(1、2、3、7、8、21)对白血病细胞株均未表现出活性;双黄酮类成分(15、16)在HIV整合酶体外抑制试验中呈现弱活性。
对海南草珊瑚95%乙醇粗提物和各部位以及我国金粟兰科八个有代表性植物的水提物和甲醇提取物进行了抗菌筛选。选用的菌株包括革兰氏阳性菌菌株(金黄色葡萄球菌)和阴性菌菌株(痢疾杆菌、绿脓杆菌、大肠杆菌)。对比海南草珊瑚的各部位,乙酸乙酯和水部位对金黄色葡萄球菌有效;在所测试的八个植物的两种提取物中,甲醇提取物的活性优于水提物;比较不同植物的甲醇提取物,丝穗金粟兰对四种菌株均有效,海南草珊瑚对金黄色葡萄球菌和痢疾杆菌有效、草珊瑚对金黄色葡萄球菌有效,及已对大肠杆菌有效。
总结上述研究结果,得到以下结论。从化学分类学角度看,海南草珊瑚的化学成分不同于草珊瑚,支持其作为分类学意义上的种存在;草珊瑚属植物的化学成分在大极性部位相近,中小极性成分各有差异;金粟兰属植物与草珊瑚属植物的主要成分接近,但含量差异较大并且存在一些特征的含量较小的化学成分,亲缘关系较近;雪香兰属植物雪香兰的化学成分与其余两属差异最大,亲缘关系最远。从药用资源开发的角度来看,现有的研究结果不支持海南草珊瑚作为草珊瑚代用,但海南草珊瑚有独特的活性成分,可以考虑对其进行相关开发利用;金粟兰属植物属间个体差异较大,采用时应慎重;雪香兰属植物可能不具有与其它金粟兰科植物相似的药用价值。
Chloranthaceae is a small family of four genera,i.e.,Sarcandra,Chloranthus, Hedyosmum and Ascarina,and ca.70 species occurring in tropical and subtropical areas. Three Genera and 16 species are distributed in the southern part of China.The whole plants or roots of plants in this family are widely used in folk medicine as antispasmodic, antiseptic,and anticancer drugs,or for relieving ache,boils,and dermatopathia in eastern Asia.Reviewed the previous studies of the family Chloranthaceae including distribution, traditional usage,chemical constituents and bioactivities,we choose the family of Chloranthaceae as an objective of our pharmacophylogenetic investigation.S. hainanensis,a shrub distributing only in the south of China,is widely used to invigorate blood circulation and eliminate blood-stasis as traditional Chinese medicine.However,to the best of our knowledge,there was no phytochemical and pharmacological report about S.hainanensis.So we initiated an investigation on the chemical constituents and bioactivities of S.hainanensis with the purpose to study the chemical constituents and differentiate S.hainanensis from S.glabra and better understand the chemotaxonomic relationship of the family of Chloranthaceae.
Kinds of chromatographic methods were employed to isolate and purify compounds from Sarcandra hainanensis.43 Compounds were isolated from the 95%ethanol extract of S.hainanensis.The structures of 36 compounds were identified by combination of spectroscopic strategies,including 18 flavanoid and derivates,12 organic acids and derivates,2 anthraquinones,1 coumarin,1 triterpenoids and 2 sterols.All the compounds were isolated from the title plant for the first time.6 compounds of them were new compounds,20 were isolated from genus Sarcandra for the first time and 18 were reported from the family of Chloranthaceae for the first time.
The six new compounds were named as sarcandrones A - F(15-18,5,6).Structures of the known compounds were identified as 2',3'-hydroxy-4',6'-dimethoxychalcone(1), 2'-hydroxy-4',5'-dimethoxychalcone(2),cardamonin(3),boesenbergin B(4),7-hydroxy -5,6-dimethoxyflavanone(7),7-hydroxy-5-methoxyflavanone(8),7-hydroxy-5,8 -dimethoxyflavanone(9),naringenin-4',7-dimethylether(10),pinostrobin(11), 3,4',5,7-tetra-hydroxyflavanone-3-O-glucoside(12),kaempferol(13),kaempferol 3-O-glucoside(14),palmitic acid(22),icosanoic acid(23),ctadecanoic acid(24), (E)-3-hydroxy-4-methoxycinnamal-dehydeacrylaldehyde(25),2,6-dihydroxy -3,5-dimethoxy-benzaldehyde(26),caffeic acid(27),rosmarinate acid(28),methyl rosmarinate(29),ethyl rosmarinate(30),3,4-dihydroxyl-phenyl-ethanol(31), (3,4-dihydroxyl-phenyl)-ethanol-O-galactoside(32)(3,4,6-trihydroxyl-phenyl)-ethanol -O-galactoside(33),acidchrysophanol(19),emodin(20),isofraxidin(21), 9,19-Cycloarta-24-en-3-ol(34),13-sitosterol(35) and daucosterin(36).
A proper chromatographic pattern for S.hainanensis based on high performance liquid chromatography coupled with diode-array detector(HPLC-DAD) was developed for the first time.Four main characteristic constituents of S.hainanensis were assayed as 2'-hydroxy-4',5'-dimethoxychalcone(2) 1.2555 mg/g,7-hydroxy-5,6-dimethoxy -flavanone(7) 0.4687 mg/g,isofraxidin(21) 0.2248 mg/g,rosmarinate acid(28) 0.5290 mg/g,respectively.The chromatographic pattern was also employed for screening the four constitunents in the 13 species of Chloranthaceae.The amounts of the constituents exited in different plants were assayed,respectively.
A MRM analytical method with LC-MS was established for screening the new biflavanoids(15-17) with trace amounts in the plants of Chloranthaceae.The result provided scientific evidences to the differnences between the constituents of S. hainanensis and that of S.glabra.
Characteristic compounds(2,3,7,15,21) isolated from S.hainanensis were detected for their bioactivities against non-small lungcancer cell lines A549,H322M,H157,H358, Hop62,H1792 and breast carcinoma cell lines T47D,MCF7.The chalcones(2,3) and biflavanoids(15) tested could significantly inhibit the survival of the above cell lines. Compounds 15 and 16 were assayed for their HIV-1 integrase inhibition activities with a microplate screening method using magnetic beads.They showed weak activities for the integrase strand transfer reaction.
The different portions of S.hainanensis as well as the water and MeOH extracts of 8 different plants of Chloranthaceae were assayed for their antibacterial activity.A Gram-positive bacteria(Staphylococcus aureus) and Gram-negative bacteria(Bacillus dysenteriae,Bacillus aeruginosus and Bacillus coli) were used.In the four different portions of S.hainanensis,EtOAc and H_2O portions were active to Staphylococcus aureus. Compared the two kinds of extrats,the MeOH extracts were more active than the H_2O ones.Among the MeOH of the 8 plants tested,Chloranthus fortunei was active to the four bacterias,S.hainanensis was active to S.aureus and Bacillus dysenteriae,S.glabra was active Staphylococcus aureus and C.serratus was active to Bacillus aeruginosus.
The results of this thesis may support the view of S.hainanensis as an independent species since its chemical profile was different from that of S.glabra.The standards with different contents in the plants of Chloranthus were determined while almost no standard was detected in the only spices of Hedyosmum.The chemotaxonomic relationship between the three genera of Chloranthaceae in China may be deduced as the species of Chloranthus having a close affinity with Sarcandra and Hedyosmum being the sister group of Sarcandra and Chloranthus according to the characteristics of chemical constituents.
In the view of the medical usage,S.hainanensis was not suitable to be used as a succedaneum of S.glabra.However,the special biological activities of S.hainanensis suggested it may be potential as a natural source of antitumor compounds.Since the species of Chloranthus were different from each other by their chemical constituents, they should be used carefully when used as folk medicine.The plants of genus Hedyosmum in China may not have the same action as S.glabra and S.hainanensis.
引文
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