苦皮藤根皮杀虫活性成分及构效关系研究
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摘要
苦皮藤(Celastrus angulatus Max.)是卫矛科南蛇藤属的一种传统杀虫植物,其活性成分为一系列具有β-二氢沉香呋喃骨架的倍半萜多元酯类化合物。本论文首次对苦皮藤根皮石油醚提取物中非极性部分的组成及生物活性进行了研究;在前期研究基础上,对苦皮藤根皮苯提取物的杀虫活性成分进行了系统分离,获得了27个β-二氢沉香呋喃类化合物,并对这类化合物的三维定量构效关系(3D-QSAR)进行了初步研究;本论文还首次采用电喷雾多级质谱方法研究了β-二氢沉香呋喃类化合物的质谱裂解规律。现将主要研究结果报告如下:
1.采用GC/MS对苦皮藤根皮石油醚提取物的非极性部分进行了分析,从中鉴定出13个化合物,分别为酞酸二异丁酯、棕榈酸、油酸、亚油酸、1,1,4α,7,7-5-甲基-3,4,4α,4β,5,6,7,8,10,10α-10-菲-2-酮、维生素A醛、弥罗松酚、弥罗松酚甲酯、角鲨烯、金合欢醇、(2Z,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-醇、(2E,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-醇和维生素E。
2.对苦皮藤根皮石油醚提取物的非极性部分进行了系统的生物活性测定。结果表明,该部分对4龄粘虫(Mythimna separata)幼虫有较强的拒食活性(50mg·mL-1,拒食率100%);对枯草芽胞杆菌(Bacillus subtilis)、蜡状芽孢杆菌(Bacillus cereus)、金黄色葡萄球菌(Staphylococcus aureus)、大肠埃氏菌(Escherichis coli)和绿脓杆菌(Pseudom- onas aeruginos)有一定的抑制作用;对供试病原真菌无抑制作用;对羟基自由基有较强的清除作用(150μg·mL-1,清除率95%)。
3.经大孔吸附树脂层析、硅胶柱层析以及高效液相色谱纯化,从苦皮藤根皮苯提取物中分离出28个化合物,并采用高分辨质谱,1H-NMR,13C-NMR以及二维核磁共振等波谱学方法对这些化合物的结构进行了鉴定。结果表明:除1个化合物为β-谷甾醇外,其余27个化合物为具有β-二氢沉香呋喃骨架的倍半萜多元酯,其中12个为新化合物:1β-乙酰氧基-2β-(α-甲基)丁酰氧基-8α,12-二异丁酰氧基-9β-苯甲酰氧基-4α,6α-二羟基-β-二氢沉香呋喃(NW12)、1β,2β,12-三乙酰氧基-8β-呋喃甲酰氧基-9β-苯甲酰氧基-4α,6α-二羟基-β-二氢沉香呋喃(NW18)、1β,2β,6α-三乙酰氧基-9α-苯甲酰氧基-12-异丁酰氧基-4α-羟基-β-二氢沉香呋喃(NW19)、1β,2β,6α,12-四乙酰氧基-9α-呋喃甲酰氧基-4α-羟基-β-二氢沉香呋喃(NW21)、1β,2β-二乙酰氧基-8α-(α-甲基)丁酰氧基-9β-苯甲酰氧基-12-异丁酰氧基-4α,6α-二羟基-β-二氢沉香呋喃(NW22)、1β,2β,8β-三乙酰氧基-9β-苯甲酰氧基-12-异丁酰氧基-4α,6α-羟基-β-二氢沉香呋喃(NW24)、1β,2β,6α,8β,12-五乙酰氧基- 9β-苯甲酰氧基-β-二氢沉香呋喃(NW25)、1β,2β,6α,12-四乙酰氧基-8β-(α-甲基)丁酰氧基-9α-苯甲酰氧基-β-二氢沉香呋喃(NW27)、1β,2β,6α-三乙酰氧基-9α-呋喃甲酰氧基-12-异丁酰氧基-4α-羟基-β-二氢沉香呋喃(NW28)、1β,2β, 6α,8β-四乙酰氧基-12-异丁酰氧基-9α-苯甲酰氧基-β-二氢沉香呋喃(NW31)、1β,2β,8β,12-四乙酰氧基-9β-呋喃甲酰氧基-4α-羟基-β-二氢沉香呋喃(NW33)和1β,2β, 6α-三乙酰氧基-8β,12-二(α-甲基)丁酰氧基-9α-苯甲酰氧基-4α-羟基-β-二氢沉香呋喃(NW37)。
4.采用含毒水质饲养法测定了β-二氢沉香呋喃多元酯对3龄白纹伊蚊(Aedes albopi- ctus)幼虫的杀虫活性。结果表明,在供试浓度下唯有以二氢沉香呋喃为母体骨架的大环生物碱对3龄白纹伊蚊幼虫有较强活性,其余化合物均未表现出明显的杀虫活性。
5.采用载毒叶片法测定了β-二氢沉香呋喃多元酯对4龄粘虫幼虫的毒杀活性。结果表明,虽然这类化合物母体结构一样,但对4龄粘虫幼虫的毒力及中毒症状都存在较大差异。
6.采用SRB法测定了β-二氢沉香呋喃多元酯体外抗肿瘤活性。结果表明,人乳腺癌细胞株Bcap-37对所有供试化合物相对敏感,而人结肠癌细胞株HT-29和肺癌细胞株NCI-H460则相对不敏感。供试的β-二氢沉香呋喃类化合物中,NW12和NW55对供试的三株肿瘤细胞系均表现出一定细胞毒性,但总体而言,这类化合物的抗肿瘤活性不高。
7.采用MTT法测定了β-二氢沉香呋喃多元酯对粉纹夜蛾胚胎细胞的细胞毒性。结果表明,粉纹夜蛾胚胎细胞对所有供试化合物均不敏感。
8.采用公共骨架叠合法对β-二氢沉香呋喃多元酯类化合物进行了3D-QSAR研究,建立了这类化合物的CoMSIA模型。结果表明,该模型具有较强的预测能力。
9.采用ESI-MS/MS归纳了β-二氢沉香呋喃多元酯的质谱裂解规律,总结出该类化合物的鉴别特征,建立了一种快速鉴别β-二氢沉香呋喃多元酯的质谱方法。将其用于液质联用分析,建立了β-二氢沉香呋喃多元酯类化合物数据库,分析了人工种植苦皮藤和野生苦皮藤根皮化学成分的差异。
Celastrus angulatus Max. is a traditional insecticidal plant in China, and its insecticidal ingredients were a series of sesquiterpene polyol esters bearingβ-dihydroagaro furan skeleton. In this paper, the components and bioactivities of the non-polar fraction of the petroleum ether extract and the benzene extract from the root bark of C. angulatus, the quantitative structure-activity relationship (QSAR) and the pathway of fragments forming and cleavage principle of the insecticidalβ-dihydroagarofuran sesquiterpere polyol esters have been carried out. The main results are as follows:
1. The constitutes of non-polar fraction of the petroleum ether extract from the root bark of C. angulatus were analyzed by GC-MS. Total of 13 compounds were identified by comparison with NIST2001 mass spectral library. They were identified as phthalic acid di-isobutyl ester, palmitic acid, oleic acid, linoleic acid, 1,1,4a,7,7 -pentamethyl-4,4a,5,6, 7,8,10,10a-octahydrophenanthren-2(1H,3H,4bH)-one, retinal, ferruginol, ferruginyl methyl ether, squalene, farnesol, (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol,(2E,6E)-3,7,11 -trimethydodeca-2,6, 10-trien-1-ol and gamma-tocopherol, respectively.
2. The non-polar fraction of the petroleum ether extract from the root bark of C. angulatus exhibited stronger antifeeding activity against the 4th instar larvae of Mythimna separata and moderate inhibition on some bacteria, such as Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, Escherichis coli and Pseudomonas aeruginos, whereas no inhibition was observed on the pathogenic fungi. The antioxidant activity were evaluated by measuring the scavenging activity on superoxide anion and hydrogen peroxide, the results showed the non-polar fraction had more significant hydrogen peroxide scavenging activity.
3. Twenty eight compounds were isolated from the benzene extract of the root bark by means of macroporous resin adsorption, silica gel column chromatography and pre-HPLC orderly. The structures of these compounds were elucidated mainly based on the data of NMR and MS. Total of twenty seven compounds were identified asβ-dihydroagarofuran sesquite- rpene polyol esters, and twelve of them were novel compounds: 1β-acetoxy-2β-(α-methyl)- butanoyloxy-8α,2-di-isobutyryl-9β-benzoyl-4α,6α-dihydroxy-β-dihydroagarofuran(NW12), 1β,2β,12-triacetoxy-8β-furoyloxy-9β-benzoyl-4α,6α-dihydroxy-β-dihydroagarof-uran(NW18),1β,2β,6α-triacetox-y-9α-benzoyl-12-iso-butyryl-4α-hydroxy-β-dihydroagarofu-ran(NW19), 1β,2β,8β,12-tetraacet-oxy-9β-furoyloxy-4α-hydroxy-β-dihydroagarofuran(NW21), 1β,2β-di- acetyl-8α-(α-methyl)-butanoyloxy-9β-benzoyl-12-iso-butyryl-4α,6α-dihydroxy-β-dihydroagarofuran(NW22),1β,2β,8β-triacetoxy-9β-benzoyl-12-iso-butyryl-4α,6α-dihydroxy-β-dihydroagarofuran(NW24),1β,2β,6α,8β,12-pentaacetyl-9β-benzoyl-β-dihydroagarofuran(NW25), 1β, 2β,6α,12–tetraacetoxy-8β-(α-methyl)-butanoyloxy-9α-benzoyl-β-dihydroagarofuran (NW27), 1β,2β,6α-triacetoxy-9α-furoyloxy-12-iso-butyryl-4α-hydroxy-β-dihydroagarofuran(NW28), 1β,2β,6α,8β-tetraacetoxy-12-iso-butyryl-9α-benzoyl-β-dihydroagarofuran(NW31), 1β,2β,6α, 12-tetraacetoxy-9-β-furoyloxy-4α-hydroxy-β-dihydroagarofuran(NW33) and 1β, 2β, 6α-tri- acetoxy-8β,12-di-(α-methyl)-butanoyloxy-9α-benzoyl-4α-hydroxy-β-dihydroagarofuran(NW37).
4. The insecticidal activities ofβ-dihydroagarofuran sesquiterpene polyol esters against the 3rd instar larvae of Aedes albopictus and the 4th instar larvae of Mythimna separata were tested. The results showed that the larvae of A. aegypti were insensitive to tested compounds except pyridine alkaloids. The results also showed that the symptom of poisoned the 4th instar larvae of Mythimna separata and the insecticidal activity of tested compounds varied with their substituted groups evidently.
5. The antitumor activity ofβ-dihydroagarofuran sesquiterpene polyol esters was screened by SRB method. The results indicated that the tested compounds have stronger inhibitory activities against human breast cancer cell line Bcap-37 than human colon cancer cell lines HT-29 and Lung cancer cell line NCI-H460. Compounds NW12 and NW55 have stronger inhibitory activities against all of them. In summary, this type of compounds only exhibited minor antitumor activity.
6. The cytotoxicity ofβ-dihydroagarofuran sesquiterpene polyol esters against Trichoplusia ni embryonic cell was measured by the method of MTT. The results showed all of them had weaker inhibition against Trichoplusia ni embryonic cell.
7. 3D-QSAR ofβ-dihydroagarofuran sesquiterpene polyol esters was studied by database alignment and the CoMSIA model was set up. The results showed that CoMSIA model had more accurate prediction for the activity of this type of compounds.
8. The pathway of fragments forming and cleavage principle ofβ-dihydroagarofuran sesquiterpene polyol esters were investigated by ESI-MS/MS and the results could be used to identify this type of compounds in the process of screening novel compounds from Celastraceae. In addition, the ESI-MS/MS spectral library ofβ-dihydroagarofuran sesquiterpene polyol esters of C. angulatus was set up. The chemical constitutes of the cultured plant and wild plant of C. angulatus were investigated by means of LC-MS/MS, and their structures were identified or deduced based on the ESI-MS/MS spectral library.
1.采用GC/MS对苦皮藤根皮石油醚提取物的非极性部分进行了分析,从中鉴定出13个化合物,分别为酞酸二异丁酯、棕榈酸、油酸、亚油酸、1,1,4α,7,7-5-甲基-3,4,4α,4β,5,6,7,8,10,10α-10-菲-2-酮、维生素A醛、弥罗松酚、弥罗松酚甲酯、角鲨烯、金合欢醇、(2Z,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-醇、(2E,6E)-3,7,11-三甲基-2,6,10-十二碳三烯-1-醇和维生素E。
2.对苦皮藤根皮石油醚提取物的非极性部分进行了系统的生物活性测定。结果表明,该部分对4龄粘虫(Mythimna separata)幼虫有较强的拒食活性(50mg·mL-1,拒食率100%);对枯草芽胞杆菌(Bacillus subtilis)、蜡状芽孢杆菌(Bacillus cereus)、金黄色葡萄球菌(Staphylococcus aureus)、大肠埃氏菌(Escherichis coli)和绿脓杆菌(Pseudom- onas aeruginos)有一定的抑制作用;对供试病原真菌无抑制作用;对羟基自由基有较强的清除作用(150μg·mL-1,清除率95%)。
3.经大孔吸附树脂层析、硅胶柱层析以及高效液相色谱纯化,从苦皮藤根皮苯提取物中分离出28个化合物,并采用高分辨质谱,1H-NMR,13C-NMR以及二维核磁共振等波谱学方法对这些化合物的结构进行了鉴定。结果表明:除1个化合物为β-谷甾醇外,其余27个化合物为具有β-二氢沉香呋喃骨架的倍半萜多元酯,其中12个为新化合物:1β-乙酰氧基-2β-(α-甲基)丁酰氧基-8α,12-二异丁酰氧基-9β-苯甲酰氧基-4α,6α-二羟基-β-二氢沉香呋喃(NW12)、1β,2β,12-三乙酰氧基-8β-呋喃甲酰氧基-9β-苯甲酰氧基-4α,6α-二羟基-β-二氢沉香呋喃(NW18)、1β,2β,6α-三乙酰氧基-9α-苯甲酰氧基-12-异丁酰氧基-4α-羟基-β-二氢沉香呋喃(NW19)、1β,2β,6α,12-四乙酰氧基-9α-呋喃甲酰氧基-4α-羟基-β-二氢沉香呋喃(NW21)、1β,2β-二乙酰氧基-8α-(α-甲基)丁酰氧基-9β-苯甲酰氧基-12-异丁酰氧基-4α,6α-二羟基-β-二氢沉香呋喃(NW22)、1β,2β,8β-三乙酰氧基-9β-苯甲酰氧基-12-异丁酰氧基-4α,6α-羟基-β-二氢沉香呋喃(NW24)、1β,2β,6α,8β,12-五乙酰氧基- 9β-苯甲酰氧基-β-二氢沉香呋喃(NW25)、1β,2β,6α,12-四乙酰氧基-8β-(α-甲基)丁酰氧基-9α-苯甲酰氧基-β-二氢沉香呋喃(NW27)、1β,2β,6α-三乙酰氧基-9α-呋喃甲酰氧基-12-异丁酰氧基-4α-羟基-β-二氢沉香呋喃(NW28)、1β,2β, 6α,8β-四乙酰氧基-12-异丁酰氧基-9α-苯甲酰氧基-β-二氢沉香呋喃(NW31)、1β,2β,8β,12-四乙酰氧基-9β-呋喃甲酰氧基-4α-羟基-β-二氢沉香呋喃(NW33)和1β,2β, 6α-三乙酰氧基-8β,12-二(α-甲基)丁酰氧基-9α-苯甲酰氧基-4α-羟基-β-二氢沉香呋喃(NW37)。
4.采用含毒水质饲养法测定了β-二氢沉香呋喃多元酯对3龄白纹伊蚊(Aedes albopi- ctus)幼虫的杀虫活性。结果表明,在供试浓度下唯有以二氢沉香呋喃为母体骨架的大环生物碱对3龄白纹伊蚊幼虫有较强活性,其余化合物均未表现出明显的杀虫活性。
5.采用载毒叶片法测定了β-二氢沉香呋喃多元酯对4龄粘虫幼虫的毒杀活性。结果表明,虽然这类化合物母体结构一样,但对4龄粘虫幼虫的毒力及中毒症状都存在较大差异。
6.采用SRB法测定了β-二氢沉香呋喃多元酯体外抗肿瘤活性。结果表明,人乳腺癌细胞株Bcap-37对所有供试化合物相对敏感,而人结肠癌细胞株HT-29和肺癌细胞株NCI-H460则相对不敏感。供试的β-二氢沉香呋喃类化合物中,NW12和NW55对供试的三株肿瘤细胞系均表现出一定细胞毒性,但总体而言,这类化合物的抗肿瘤活性不高。
7.采用MTT法测定了β-二氢沉香呋喃多元酯对粉纹夜蛾胚胎细胞的细胞毒性。结果表明,粉纹夜蛾胚胎细胞对所有供试化合物均不敏感。
8.采用公共骨架叠合法对β-二氢沉香呋喃多元酯类化合物进行了3D-QSAR研究,建立了这类化合物的CoMSIA模型。结果表明,该模型具有较强的预测能力。
9.采用ESI-MS/MS归纳了β-二氢沉香呋喃多元酯的质谱裂解规律,总结出该类化合物的鉴别特征,建立了一种快速鉴别β-二氢沉香呋喃多元酯的质谱方法。将其用于液质联用分析,建立了β-二氢沉香呋喃多元酯类化合物数据库,分析了人工种植苦皮藤和野生苦皮藤根皮化学成分的差异。
Celastrus angulatus Max. is a traditional insecticidal plant in China, and its insecticidal ingredients were a series of sesquiterpene polyol esters bearingβ-dihydroagaro furan skeleton. In this paper, the components and bioactivities of the non-polar fraction of the petroleum ether extract and the benzene extract from the root bark of C. angulatus, the quantitative structure-activity relationship (QSAR) and the pathway of fragments forming and cleavage principle of the insecticidalβ-dihydroagarofuran sesquiterpere polyol esters have been carried out. The main results are as follows:
1. The constitutes of non-polar fraction of the petroleum ether extract from the root bark of C. angulatus were analyzed by GC-MS. Total of 13 compounds were identified by comparison with NIST2001 mass spectral library. They were identified as phthalic acid di-isobutyl ester, palmitic acid, oleic acid, linoleic acid, 1,1,4a,7,7 -pentamethyl-4,4a,5,6, 7,8,10,10a-octahydrophenanthren-2(1H,3H,4bH)-one, retinal, ferruginol, ferruginyl methyl ether, squalene, farnesol, (2Z,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol,(2E,6E)-3,7,11 -trimethydodeca-2,6, 10-trien-1-ol and gamma-tocopherol, respectively.
2. The non-polar fraction of the petroleum ether extract from the root bark of C. angulatus exhibited stronger antifeeding activity against the 4th instar larvae of Mythimna separata and moderate inhibition on some bacteria, such as Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, Escherichis coli and Pseudomonas aeruginos, whereas no inhibition was observed on the pathogenic fungi. The antioxidant activity were evaluated by measuring the scavenging activity on superoxide anion and hydrogen peroxide, the results showed the non-polar fraction had more significant hydrogen peroxide scavenging activity.
3. Twenty eight compounds were isolated from the benzene extract of the root bark by means of macroporous resin adsorption, silica gel column chromatography and pre-HPLC orderly. The structures of these compounds were elucidated mainly based on the data of NMR and MS. Total of twenty seven compounds were identified asβ-dihydroagarofuran sesquite- rpene polyol esters, and twelve of them were novel compounds: 1β-acetoxy-2β-(α-methyl)- butanoyloxy-8α,2-di-isobutyryl-9β-benzoyl-4α,6α-dihydroxy-β-dihydroagarofuran(NW12), 1β,2β,12-triacetoxy-8β-furoyloxy-9β-benzoyl-4α,6α-dihydroxy-β-dihydroagarof-uran(NW18),1β,2β,6α-triacetox-y-9α-benzoyl-12-iso-butyryl-4α-hydroxy-β-dihydroagarofu-ran(NW19), 1β,2β,8β,12-tetraacet-oxy-9β-furoyloxy-4α-hydroxy-β-dihydroagarofuran(NW21), 1β,2β-di- acetyl-8α-(α-methyl)-butanoyloxy-9β-benzoyl-12-iso-butyryl-4α,6α-dihydroxy-β-dihydroagarofuran(NW22),1β,2β,8β-triacetoxy-9β-benzoyl-12-iso-butyryl-4α,6α-dihydroxy-β-dihydroagarofuran(NW24),1β,2β,6α,8β,12-pentaacetyl-9β-benzoyl-β-dihydroagarofuran(NW25), 1β, 2β,6α,12–tetraacetoxy-8β-(α-methyl)-butanoyloxy-9α-benzoyl-β-dihydroagarofuran (NW27), 1β,2β,6α-triacetoxy-9α-furoyloxy-12-iso-butyryl-4α-hydroxy-β-dihydroagarofuran(NW28), 1β,2β,6α,8β-tetraacetoxy-12-iso-butyryl-9α-benzoyl-β-dihydroagarofuran(NW31), 1β,2β,6α, 12-tetraacetoxy-9-β-furoyloxy-4α-hydroxy-β-dihydroagarofuran(NW33) and 1β, 2β, 6α-tri- acetoxy-8β,12-di-(α-methyl)-butanoyloxy-9α-benzoyl-4α-hydroxy-β-dihydroagarofuran(NW37).
4. The insecticidal activities ofβ-dihydroagarofuran sesquiterpene polyol esters against the 3rd instar larvae of Aedes albopictus and the 4th instar larvae of Mythimna separata were tested. The results showed that the larvae of A. aegypti were insensitive to tested compounds except pyridine alkaloids. The results also showed that the symptom of poisoned the 4th instar larvae of Mythimna separata and the insecticidal activity of tested compounds varied with their substituted groups evidently.
5. The antitumor activity ofβ-dihydroagarofuran sesquiterpene polyol esters was screened by SRB method. The results indicated that the tested compounds have stronger inhibitory activities against human breast cancer cell line Bcap-37 than human colon cancer cell lines HT-29 and Lung cancer cell line NCI-H460. Compounds NW12 and NW55 have stronger inhibitory activities against all of them. In summary, this type of compounds only exhibited minor antitumor activity.
6. The cytotoxicity ofβ-dihydroagarofuran sesquiterpene polyol esters against Trichoplusia ni embryonic cell was measured by the method of MTT. The results showed all of them had weaker inhibition against Trichoplusia ni embryonic cell.
7. 3D-QSAR ofβ-dihydroagarofuran sesquiterpene polyol esters was studied by database alignment and the CoMSIA model was set up. The results showed that CoMSIA model had more accurate prediction for the activity of this type of compounds.
8. The pathway of fragments forming and cleavage principle ofβ-dihydroagarofuran sesquiterpene polyol esters were investigated by ESI-MS/MS and the results could be used to identify this type of compounds in the process of screening novel compounds from Celastraceae. In addition, the ESI-MS/MS spectral library ofβ-dihydroagarofuran sesquiterpene polyol esters of C. angulatus was set up. The chemical constitutes of the cultured plant and wild plant of C. angulatus were investigated by means of LC-MS/MS, and their structures were identified or deduced based on the ESI-MS/MS spectral library.
引文
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