四种药用植物和一种真菌的化学成分及生物活性研究
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摘要
本文对四种药用植物唐古特青兰Dracocephalum tanguticum、湖北海棠Malus hupehensis、毒芹Cicuta. virosa、八角莲Dysosma versipellis和一种真菌玉米瘤黑粉菌Ustilago maydis进行了系统的化学成分研究和生物活性测试。运用波谱学技术、化学反应沟通和计算化学等手段鉴定了90个化合物,其中包括生物碱类化合物5个,黄酮类化合物35个,香豆素类化合物15个,以及其他类化合物35个。其中新化合物11个。此外,对各类化合物进行了细胞毒、心肌细胞保护和抗肿瘤耐药逆转等活性筛选,一些化合物显示了较好的活性,并进一步研究了其作用机制。
本文对唐古特青兰全草的乙醇提取物进行了系统的化学成分分离,共获得了32个化合物,采用一维和二维NMR以及高分辨MS等波谱法对其结构进行了鉴定,其中包括生物碱5个(1-5),黄酮类化合物17个(6-22)和其他类化合物10个(23-32)。其中dracotanosides A-E (1-5), ladanetin-6-O-β-(6"-O-acetyl)glucoside (6)和pedalitin-3'-O-β-glucoside(7)等7个为新化合物。通过体外心肌细胞培养,观察了黄酮类化合物对阿霉素诱导的心肌细胞损伤的保护作用,发现化合物木犀草素-7-O-β-D-葡萄糖苷(12)具有较好的心肌细胞保护作用。研究了木犀草素-7-O-β-D-葡萄糖苷的抗氧化作用机制和抗心肌细胞凋亡机制。并通过初步的构效分析发现,C环双键和B环3',4'-二羟基对其活性有关键影响。此外,还测定了分离获得的生物碱类化合物1-5的细胞毒活性,均未表现生长抑制作用。
本文对湖北海棠叶的乙醇提取物进行了系统的化学成分研究,共获得19个化合物,采用波谱学结合量子化学计算的方法对其进行了结构鉴定,其中化合物(P)-phloridzin-(I-5,Ⅱ-3')-phloretin-4'-O-glucoside (33), (M)-phloridzin-(Ⅰ-5,Ⅱ-3')-phloretin-4'-O-glucoside (34),和phloridzin-(Ⅰ-4,O,Ⅱ-2')-luteolin-5-O-glucoside (35)为新化合物。在所得化合物中,33和34为旋阻异构体,本文通过将其实验测得的CD谱与理论计算的CD谱比较,可确定33为P-构型,34为M-构型。对所分离化合物进行了α-葡萄糖苷酶抑制活性筛选,得化合物均未显示α-葡萄糖苷酶抑制活性。
本文对毒芹地上部分的乙醇提取物进行了系统的化学成分研究,共分离获得18个化合物,其中包括二聚香豆素类化合物1个(48),香豆素类化合物15个(49-62),黄酮类化合物2个(63,64)和苄醇类化合物1个(65)。其中化合物diarchangelicin A (48)为新化合物。以MTT法筛选香豆素类化合物对人类白血病细胞系K562及其耐药细胞株K562/A02多药耐药的逆转作用,发现欧白芷素(49)具有较好的逆转耐药活性。初步研究了欧白芷素的作用机制,发现欧白芷素能明显抑制罗丹明123(Rh123)的外排,进而使Rh123在细胞内的积累升高。进一步研究发现,欧白芷素可在mRNA水平抑制K562/A02细胞中P-gp的表达。综上所述,欧白芷素通过抑制MDR1基因的表达和P-gp的功能,抑制药物外排,增加细胞内阿霉素的浓度来发挥其逆转耐药作用。
本文对八角莲根的乙醇提取物进行了系统的化学成分研究,分离获得了13个已知化合物：东莨菪内酯(66),二十四烷酸(67),5-羟基-7,3',4'-三甲氧基黄酮(68),异鼠李素(69), (+)-medioresinol(70),香草酸(71),鬼臼毒素(72),5,7-二羟基-色原酮(24),齐墩果酸(25),熊果酸(26),β-胡萝卜苷(31)和β-谷甾醇(32)。
本文首次采用各种色谱技术对玉米瘤黑粉菌的乙醇提取物进行了系统的化学成分分离,从中获得了18个化合物：stellasterin (73),5α-cholest- 7-en-3β-ol (74),过氧麦角甾醇(75), N-trans-p-coumaroyl tyramine (76), N-cis-p- coumaroyltyramine (77), N-trans-feruloyl-3-methoxytyramine (78), N-cis-feruloyl-3-methoxytyramine (79),5,7-dihydroxy-4-methyl-2(1H)-quinolinone (80),6-ethoxy-4-methoxy-1-naphthalenol (81),邻苯二甲酸二正丁酯(82),邻苯二丙酸二乙酯(83),异香草酸(84),对乙氧基苯甲酸(85),3,4-二甲氧基-二羟基苯甲酸(86),3-methoxy-benzoic acid (87), 1-O-Methyl-β-D-glucopyranoside (88), 1-O-ethyl-β-D-glucopyranoside (89)和1-O-n-Butyl-β-D-glucopyranoside(90)。
Four medicinal plants Dracocephalum tanguticum, Malus hupehensis, Cicuta. virosa, and Dysosma versipelli and one fungus Ustilago maydis have been chemically investigated and their bioactivities have been evaluated. A total of 90 compounds were obtained, which were characterized as five alkaloids,35 flavonoids,15 coumarins, and 35 other compounds on the basis of extensive spectroscopic data, chemical transformations, and quantum chemical computation. Eleven compounds were new secondary metabolites.
Five new alkaloids dracotanosides A-E (1-5) and two new flavonoids, ladanetin-6-O-β-(6"-O-acetyl)glucoside (6) and pedalitin-3'-O-β-glucoside (7), together with 25 known compounds, were isolated from the whole plants of Dracocephalum tanguticum. Their structures were established on the basis of extensive spectroscopic (IR, MS, and NMR) data analysis and by comparison with spectroscopic data reported in the literature. Antioxidant capacities of the isolated flavonoids were determined and their cytoprotective activities were also tested against doxorubicin (DOX)-induced toxicity in H9c2 cardiomyocytes. Among all the tested compounds, luteolin-7-O-β-D-glucopyranoside (12) exhibited both strong antioxidative effect and high protective activity against DOX-induced toxicity. Further investigation found that 12 could decrease DOX-induced death of H9c2 cell, reduce LDH and CK level, and inhibit the elevated intracellular concentration of ROS and [Ca2+]i. The preliminary structure-activity relationships (SAR) of these compounds revealed the△2,3-double bond on C-ring and 3',4'-di-OHs on B-ring of a flavone skeleton such as luteolin and its derivatives, were necessary for their cardioprotective effects.
Three new biflavonoid glycosides (33-35) were isolated from the leaves of Malus hupehensis, along with 16 known compounds. Their structures were elucidated by spectroscopic analyses. The absolute structures of 33 and 34?? were determined by combination of CD and computational methods, and each of them was shown to be in an atropisomeric relationship.
A new dimeric coumarin, diarchangelicin A (48), together with 17 known compounds, were isolated from the aerial part of Cicuta virosa and their structures were elucidated by spectroscopic methods. In addition, the known compounds were evaluated for multidrug resistance reversing activity by using doxorubicin-resistant K562/A02 cells. Archangelicin (Arc,48) was endowed with remarkable MDR reverting effects, and the maximal reversal fold (RF) was 7.36. The action of Arc was confirmed by the increase of intracellular accumulation of Dox in K562/A02 cells. The function of P-gp was blocked, and the expression of MDR1 mRNA and P-gp were also inhibited by Arc. Accordingly, Arc reversed effectively MDR via inhibiting P-gp expression and function, and may be used as MDR reversal drugs to increase the effectiveness of chemotherapy.
Thirteen known compounds, including scopoletin (66), tetracosanoic acid (67), 5-hydroxyl-7,3',4'-trimethoxy flavone (68), isorhamnetin (69), (+)-medioresinol (70), 4-hydroxy-3-methoxybenzoic acid (71), podophyllotoxin (72),5,7-dihydroxychromone (24), oleanolic acid (25), ursolic acid (26),β-daucosterol (31), andβ-sitosterol (32) were isolated from Dysosma versipellis.
Eighteen known compounds, including stellasterin (73),5α- cholest-7-en-3β-ol (74), peroxyergosterol (75), N-trans-p-coumaroyl tyramine (76), N-cis-p-coumaroyltyr-amine (77),N-trans-feruloyl-3-methoxytyramine (78),N-cis-feruloyl-3-methoxyty-ramine (79),5,7-dihydroxy-4-methyl-2(1H)-quinolinone (80),6-ethoxy-4-methoxy-1-naphthalenol (81),1,2-benzenedicarboxylic acid (82),1,2-benzenedipropanoic acid diethyl ester (83),3-hydroxy-p-anisic acid (84),4-ethoxybenzoic acid (85), 3,4-dimethoxysalicylic acid (86),3-methoxybenzoic acid (87),1-O-Methyl-β-D-glucopyranoside (88),1-O-ethyl-β-D-glucopyranoside (89), 1-O-n-Butyl-β-D-glucopyranoside (90) were isolated from Ustilago maydis.
本文对唐古特青兰全草的乙醇提取物进行了系统的化学成分分离,共获得了32个化合物,采用一维和二维NMR以及高分辨MS等波谱法对其结构进行了鉴定,其中包括生物碱5个(1-5),黄酮类化合物17个(6-22)和其他类化合物10个(23-32)。其中dracotanosides A-E (1-5), ladanetin-6-O-β-(6"-O-acetyl)glucoside (6)和pedalitin-3'-O-β-glucoside(7)等7个为新化合物。通过体外心肌细胞培养,观察了黄酮类化合物对阿霉素诱导的心肌细胞损伤的保护作用,发现化合物木犀草素-7-O-β-D-葡萄糖苷(12)具有较好的心肌细胞保护作用。研究了木犀草素-7-O-β-D-葡萄糖苷的抗氧化作用机制和抗心肌细胞凋亡机制。并通过初步的构效分析发现,C环双键和B环3',4'-二羟基对其活性有关键影响。此外,还测定了分离获得的生物碱类化合物1-5的细胞毒活性,均未表现生长抑制作用。
本文对湖北海棠叶的乙醇提取物进行了系统的化学成分研究,共获得19个化合物,采用波谱学结合量子化学计算的方法对其进行了结构鉴定,其中化合物(P)-phloridzin-(I-5,Ⅱ-3')-phloretin-4'-O-glucoside (33), (M)-phloridzin-(Ⅰ-5,Ⅱ-3')-phloretin-4'-O-glucoside (34),和phloridzin-(Ⅰ-4,O,Ⅱ-2')-luteolin-5-O-glucoside (35)为新化合物。在所得化合物中,33和34为旋阻异构体,本文通过将其实验测得的CD谱与理论计算的CD谱比较,可确定33为P-构型,34为M-构型。对所分离化合物进行了α-葡萄糖苷酶抑制活性筛选,得化合物均未显示α-葡萄糖苷酶抑制活性。
本文对毒芹地上部分的乙醇提取物进行了系统的化学成分研究,共分离获得18个化合物,其中包括二聚香豆素类化合物1个(48),香豆素类化合物15个(49-62),黄酮类化合物2个(63,64)和苄醇类化合物1个(65)。其中化合物diarchangelicin A (48)为新化合物。以MTT法筛选香豆素类化合物对人类白血病细胞系K562及其耐药细胞株K562/A02多药耐药的逆转作用,发现欧白芷素(49)具有较好的逆转耐药活性。初步研究了欧白芷素的作用机制,发现欧白芷素能明显抑制罗丹明123(Rh123)的外排,进而使Rh123在细胞内的积累升高。进一步研究发现,欧白芷素可在mRNA水平抑制K562/A02细胞中P-gp的表达。综上所述,欧白芷素通过抑制MDR1基因的表达和P-gp的功能,抑制药物外排,增加细胞内阿霉素的浓度来发挥其逆转耐药作用。
本文对八角莲根的乙醇提取物进行了系统的化学成分研究,分离获得了13个已知化合物：东莨菪内酯(66),二十四烷酸(67),5-羟基-7,3',4'-三甲氧基黄酮(68),异鼠李素(69), (+)-medioresinol(70),香草酸(71),鬼臼毒素(72),5,7-二羟基-色原酮(24),齐墩果酸(25),熊果酸(26),β-胡萝卜苷(31)和β-谷甾醇(32)。
本文首次采用各种色谱技术对玉米瘤黑粉菌的乙醇提取物进行了系统的化学成分分离,从中获得了18个化合物：stellasterin (73),5α-cholest- 7-en-3β-ol (74),过氧麦角甾醇(75), N-trans-p-coumaroyl tyramine (76), N-cis-p- coumaroyltyramine (77), N-trans-feruloyl-3-methoxytyramine (78), N-cis-feruloyl-3-methoxytyramine (79),5,7-dihydroxy-4-methyl-2(1H)-quinolinone (80),6-ethoxy-4-methoxy-1-naphthalenol (81),邻苯二甲酸二正丁酯(82),邻苯二丙酸二乙酯(83),异香草酸(84),对乙氧基苯甲酸(85),3,4-二甲氧基-二羟基苯甲酸(86),3-methoxy-benzoic acid (87), 1-O-Methyl-β-D-glucopyranoside (88), 1-O-ethyl-β-D-glucopyranoside (89)和1-O-n-Butyl-β-D-glucopyranoside(90)。
Four medicinal plants Dracocephalum tanguticum, Malus hupehensis, Cicuta. virosa, and Dysosma versipelli and one fungus Ustilago maydis have been chemically investigated and their bioactivities have been evaluated. A total of 90 compounds were obtained, which were characterized as five alkaloids,35 flavonoids,15 coumarins, and 35 other compounds on the basis of extensive spectroscopic data, chemical transformations, and quantum chemical computation. Eleven compounds were new secondary metabolites.
Five new alkaloids dracotanosides A-E (1-5) and two new flavonoids, ladanetin-6-O-β-(6"-O-acetyl)glucoside (6) and pedalitin-3'-O-β-glucoside (7), together with 25 known compounds, were isolated from the whole plants of Dracocephalum tanguticum. Their structures were established on the basis of extensive spectroscopic (IR, MS, and NMR) data analysis and by comparison with spectroscopic data reported in the literature. Antioxidant capacities of the isolated flavonoids were determined and their cytoprotective activities were also tested against doxorubicin (DOX)-induced toxicity in H9c2 cardiomyocytes. Among all the tested compounds, luteolin-7-O-β-D-glucopyranoside (12) exhibited both strong antioxidative effect and high protective activity against DOX-induced toxicity. Further investigation found that 12 could decrease DOX-induced death of H9c2 cell, reduce LDH and CK level, and inhibit the elevated intracellular concentration of ROS and [Ca2+]i. The preliminary structure-activity relationships (SAR) of these compounds revealed the△2,3-double bond on C-ring and 3',4'-di-OHs on B-ring of a flavone skeleton such as luteolin and its derivatives, were necessary for their cardioprotective effects.
Three new biflavonoid glycosides (33-35) were isolated from the leaves of Malus hupehensis, along with 16 known compounds. Their structures were elucidated by spectroscopic analyses. The absolute structures of 33 and 34?? were determined by combination of CD and computational methods, and each of them was shown to be in an atropisomeric relationship.
A new dimeric coumarin, diarchangelicin A (48), together with 17 known compounds, were isolated from the aerial part of Cicuta virosa and their structures were elucidated by spectroscopic methods. In addition, the known compounds were evaluated for multidrug resistance reversing activity by using doxorubicin-resistant K562/A02 cells. Archangelicin (Arc,48) was endowed with remarkable MDR reverting effects, and the maximal reversal fold (RF) was 7.36. The action of Arc was confirmed by the increase of intracellular accumulation of Dox in K562/A02 cells. The function of P-gp was blocked, and the expression of MDR1 mRNA and P-gp were also inhibited by Arc. Accordingly, Arc reversed effectively MDR via inhibiting P-gp expression and function, and may be used as MDR reversal drugs to increase the effectiveness of chemotherapy.
Thirteen known compounds, including scopoletin (66), tetracosanoic acid (67), 5-hydroxyl-7,3',4'-trimethoxy flavone (68), isorhamnetin (69), (+)-medioresinol (70), 4-hydroxy-3-methoxybenzoic acid (71), podophyllotoxin (72),5,7-dihydroxychromone (24), oleanolic acid (25), ursolic acid (26),β-daucosterol (31), andβ-sitosterol (32) were isolated from Dysosma versipellis.
Eighteen known compounds, including stellasterin (73),5α- cholest-7-en-3β-ol (74), peroxyergosterol (75), N-trans-p-coumaroyl tyramine (76), N-cis-p-coumaroyltyr-amine (77),N-trans-feruloyl-3-methoxytyramine (78),N-cis-feruloyl-3-methoxyty-ramine (79),5,7-dihydroxy-4-methyl-2(1H)-quinolinone (80),6-ethoxy-4-methoxy-1-naphthalenol (81),1,2-benzenedicarboxylic acid (82),1,2-benzenedipropanoic acid diethyl ester (83),3-hydroxy-p-anisic acid (84),4-ethoxybenzoic acid (85), 3,4-dimethoxysalicylic acid (86),3-methoxybenzoic acid (87),1-O-Methyl-β-D-glucopyranoside (88),1-O-ethyl-β-D-glucopyranoside (89), 1-O-n-Butyl-β-D-glucopyranoside (90) were isolated from Ustilago maydis.
引文
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