芭蕉根、芭蕉花和南湖菱活性成分研究
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摘要
本论文共由三章组成。第一章对苗药芭蕉根和芭蕉花的化学成分进行了研究,并对芭蕉根和芭蕉花的各个提取物及单体化合物进行了体外抗氧化、抑制α-葡萄糖苷酶和抑菌活性筛选。第二章对南湖菱果壳的化学成分进行了研究,并对其各个提取物及单体化合物进行了体外抗氧化、抑制α-葡萄糖苷酶和抑菌活性筛选。第三章,综述了菱科菱属植物的化学成分和药理活性研究现状,以期对其进行更好的开发利用。
第一章芭蕉根和芭蕉花的化学成分及生物活性研究
采用常规柱色谱方法对芭蕉根和芭蕉花进行了系统的化学成分研究,从芭蕉根中分离得到7个化合物,分别为2',3,4'-三羟基黄酮(1)、3,3'-bis-hydroxyanigorufone(2).豆甾醇(3)、Irenolone(4).2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone(5).3,4-二羟基苯甲醛(6)和β-胡萝卜苷(7),化合物1、2、4、5、6为首次从该植物中分离得到,6为首次从该属中分离得到。从芭蕉花中分离得到8个化合物,鉴定了其中2个,分别为豆甾醇(4)和胡萝卜苷(7),化合物4和7均为首次从该植物中分离得到。
二、采用DPPH.ABTS和FRAP 3种方法综合评价芭蕉根和芭蕉花的抗氧化活性,发现芭蕉根各提取部位均具有较好的抗氧化活性,芭蕉花无抗氧化活性。采用DPPH微量法测定了从芭蕉根和芭蕉花中分离得到的单体化合物的抗氧化活性,其中2',3,4'-三羟基黄酮(IC50=8.61μg·mL-1).Irenolone(IC50=19.55μg·mL-1)和3,4-二羟基苯甲醛(IC50=1.1μg·mL-1)显示很好的抗氧化能力。
三、采用96微孔板法对芭蕉根和芭蕉花的各提取物和单体化合物进行体外抑制α-葡萄糖苷酶活性筛选,发现芭蕉根石油醚部位、乙酸乙酯部位、甲醇部位及芭蕉花石油醚部位具有α-葡萄糖苷酶抑制活性,其中芭蕉花石油醚部位活性最高。3,3'-bis-hydroxyanigorufone ( IC50 = 24.15μg·mL-1)和2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone(IC50=2.81μg·mL-1)具有很强的α-葡萄糖苷酶抑制活性,远高于阳性对照Acarbose (IC50=1103.01μg·mL-1)。
四、研究了芭蕉根和芭蕉花各提取物和单体化合物体外抑制SA, MRSA和ESBLs-SA活性,发现芭蕉根和芭蕉花的石油醚部位是芭蕉的抗菌活性部位,单体化合物2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone具有很强的抑菌活性,对SA, MRSA, ESBLs-SA的MIC分别为0.078,0.313,0.039μg/disc。
第二章南湖菱的化学成分及生物活性研究
一、采用常规柱色谱方法对南湖菱果壳进行了系统的化学成分研究,从中分离得到12个化合物,鉴定了其中9个,分别为：4,23,24-三甲基胆甾-22-烯-3-醇(1),豆甾醇(2),α-香树脂醇(4), (E)-bis-4,4'-(3-ethenyl-1-propene-1,3-diyl)-phenol (5),齐墩果酸(7),熊果酸(8),常春藤皂苷元(9),3,23-二羟基-12-烯-28-乌苏酸(10),β-胡萝卜苷(12),化合物1、2、4、5、7、8、9、10和12均为首次从该植物中分离得到。
二、采用DPPH、ABTS和FRAP 3种方法综合评价南湖菱果壳各提取物的体外抗氧化活性,发现其甲醇-水提取物、石油醚部位、乙酸乙酯部位和正丁醇部位均具有较好的抗氧化活性,其中乙酸乙酯部位活性最高。
三、采用96微孔板法对南湖菱果壳各提取物进行体外抑制a-葡萄糖苷酶活性筛选,发现其甲醇-水提取物(IC50=2.00μg·mL-1)、石油醚部位(IC50=14.4μg·mL-1)、乙酸乙酯部位(IC50=0.4μg·mL-1)和正丁醇部位(IC50=1.00μg·mL-1)均具有显著的α-葡萄糖苷酶抑制活性,远高于阳性对照Acarbose (IC50=1103.01μg·mL-1)。
四、研究了南湖菱果壳各提取物体外抑制SA, MRSA和ESBLs-SA活性,发现其甲醇-水提取物、石油醚部位、乙酸乙酯部位和正丁醇部位对SA, MRSA和ESBLs-SA均有抑制作用。其中甲醇-水提取物(IC50=0.46 mg·mL-1)对SA的抑制效果最好,石油醚部位对MRSA (IC50=0.62 mg·mL-1)和ESBLs-SA (IC50=0.34 mg·mL-1)的抑制作用最好。甲醇-水和石油醚提取物是其表现抗菌效果的活性部位。
第三章菱科菱属植物研究进展
本章从化学成分和药理作用两方面对菱科菱属植物的研究现状进行了综述,以期对其进行更好的开发利用。
This dissertation is composed of three chapters. The first chapter showed the isolation and identification of compounds from rhizomes and flowers of Musa basjoo Sieb. et Zucc, and the antioxidant, a-glucosidase inhibitory as well as anti-bacterias activity of different extracts and compounds were introduced. The second chapter studied the isolation and identification of compounds from Trapa acornis Nakano, besides, the antioxidant, a-glucosidase inhibitory and anti-bacterias activity of different extracts and compounds were reported. The third chapter summarized the study progress of chemical constituent and pharmaceutical of the genus Trapa.
Chapter 1. The chemical constituents and bioactivities of rhizomes and
flowers of Musa basjoo Sieb. et Zucc
1. The chemical constituents from the rhizomes and flowers of Musa basjoo Sieb. et Zucc were studied by column chromatography. Seven compounds were isolated from the rhizomes of M. basjoo and identified as 2',3,4'-Trihydroxyflavone (1),3,3'-bis-hydroxyanigorufone (2), Stigmasterol(3), Irenolone (4), 2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone (5),3,4-dihydroxybenzaldehyde (6) andβ-daucosterol (7). Compound 1、2、4、5、6 were isolated from this plant for the first time. Compound 6 was isolated from Musa genus for the first time. Eight compounds were isolated from the flowers of M. basjoo, two compounds were identified as Stigmasterol(4) andβ-daucosterol (7). Compound 4 and 7 were isolated from this plant for the first time.
2. DPPH, ABTS, and FRAP assays were used to screen the antioxidant activity of rhizomes and flowers of M. basjoo. Different extracts from the rhizomes of M. basjoo showed better antioxidant activity, but the extracts from flowers didn't have the activity. The activity of compounds was screened by scavenging activity against DPPH. radical with microplate assay. 2',3,4'-Trihydroxyflavone (IC50=8.61μg·mL-1), Irenolone(IC50=19.55μg·mL-1) and 3,4-dihydroxybenzaldehyde(IC50=1.1μg·mL-1) exhibited strong activity.
3. The inhibitory effect against a-glucosidase of different extracts and compounds from rhizomes and flowers of M. basjoo were screened in a 96-well plate. Petroleum ether, EtOAC, MeOH extracts of the rhizomes and petroleum ether extracts of the flowers showed stronger inhibitory effect against a-glucosidase, and petroleum ether extracts of the flowers was the highest.3,3'-bis-hydroxyanigorufone (IC50=24.15μg·mL-1) and 2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone (IC50=2.81μg·mL-1) exhibited stronger inhibitory activity,which were much higher than that of acarbose (IC50=1103.01μg·mL-1)
4. Antibacterial activity of different extracts and compounds from rhizomes and flowers of M. basjoo were assayed by using Staphylococcus aureus(SA), methicillin-resistant Staphylococcus aureus (MRSA) andβ-lactamase positive Staphylococcus aureus(ESBLs-SA). Petroleum ether extracts of rhizome and flower were active fraction.2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone showed strong activity with MIC value of 0.078,0.313,0.039μg/disc against SA, MRSA and ESBLs-SA respectively.
Chapter 2. The chemical constituents and bioactivities of Trapa acornis Nakano
1. The chemical constituents from the nutshell of Trapa acornis Nakano were studied by column chromatography. Twelve compounds were isolated and nine were identified as 4,23,24-trimethylcholest-22-en-3-ol(1), Stigmasterol(2), a-amyrin(4), (E)-bis-4,4'-(3-ethenyl-l-propene-1,3-diyl)-phenol (5), oleanolic acid(7), ursolic acid(8), Hederagenin(9), 3,23-dihydroxy-12-ursen-28-oic acid(10) andβ-daucosterol(12). Compound 1,2,4,5,7,8,9,10 and 12 were isolated from this plant for the first time.
2. The antioxidant activity of different extracts of nueshell of T. acornis was screened by the DPPH, ABTS, and FRAP assays. The MeOH/water, petroleum ether, EtOAC and n-butyl alcohol extracts showed better antioxidant activity, and the EtOAC extracts was the highest.
3. The inhibitory effect against a-glucosidase of different extracts from nutshell of T. acornis were screened in a 96-well plate. MeOH/water (IC50=2.00μg·mL-1), petroleum ether (IC50=14.4μg·mL-1), EtOAC (IC50=0.4μg·mL-1) and n-butyl alcohol (IC50=1.00μg·mL-1) extracts showed stronger inhibitory effect against a-glucosidase, which were much higher than that of acarbose (IC50=1103.01μg·mL-1)
4. Antibacterial activity againet Staphylococcus aureus(SA), methicillin-resistant Staphylococcus aureus (MRSA) andβ-Mactamase positive Staphylococcus aureus(ESBLs-SA) of different extracts from nutshell of T. acornis were assayed. The MeOH/water, petroleum ether, EtOAC and n-butyl alcohol extracts exhibited antibacterial activity. The MeOH/water extracts displayed the best antibacterial activity of SA with IC50 value of 0.46 mg-mL-1. Petroleum ether extract showed the best antibacterial activity of MRSA and ESBLs-SA with IC50 value of 0.62, 0.34 mg-mL-1 respectively. The antibacterial activity ingredients mainly in the MeOH/water and petroleum ether extracts.
Chapter 3. The study progress of chemical constituent and pharmaceutical of the genus Trapa
The study progress of chemical constituent and pharmaceutical of the genus Trapa were summarized.
第一章芭蕉根和芭蕉花的化学成分及生物活性研究
采用常规柱色谱方法对芭蕉根和芭蕉花进行了系统的化学成分研究,从芭蕉根中分离得到7个化合物,分别为2',3,4'-三羟基黄酮(1)、3,3'-bis-hydroxyanigorufone(2).豆甾醇(3)、Irenolone(4).2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone(5).3,4-二羟基苯甲醛(6)和β-胡萝卜苷(7),化合物1、2、4、5、6为首次从该植物中分离得到,6为首次从该属中分离得到。从芭蕉花中分离得到8个化合物,鉴定了其中2个,分别为豆甾醇(4)和胡萝卜苷(7),化合物4和7均为首次从该植物中分离得到。
二、采用DPPH.ABTS和FRAP 3种方法综合评价芭蕉根和芭蕉花的抗氧化活性,发现芭蕉根各提取部位均具有较好的抗氧化活性,芭蕉花无抗氧化活性。采用DPPH微量法测定了从芭蕉根和芭蕉花中分离得到的单体化合物的抗氧化活性,其中2',3,4'-三羟基黄酮(IC50=8.61μg·mL-1).Irenolone(IC50=19.55μg·mL-1)和3,4-二羟基苯甲醛(IC50=1.1μg·mL-1)显示很好的抗氧化能力。
三、采用96微孔板法对芭蕉根和芭蕉花的各提取物和单体化合物进行体外抑制α-葡萄糖苷酶活性筛选,发现芭蕉根石油醚部位、乙酸乙酯部位、甲醇部位及芭蕉花石油醚部位具有α-葡萄糖苷酶抑制活性,其中芭蕉花石油醚部位活性最高。3,3'-bis-hydroxyanigorufone ( IC50 = 24.15μg·mL-1)和2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone(IC50=2.81μg·mL-1)具有很强的α-葡萄糖苷酶抑制活性,远高于阳性对照Acarbose (IC50=1103.01μg·mL-1)。
四、研究了芭蕉根和芭蕉花各提取物和单体化合物体外抑制SA, MRSA和ESBLs-SA活性,发现芭蕉根和芭蕉花的石油醚部位是芭蕉的抗菌活性部位,单体化合物2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone具有很强的抑菌活性,对SA, MRSA, ESBLs-SA的MIC分别为0.078,0.313,0.039μg/disc。
第二章南湖菱的化学成分及生物活性研究
一、采用常规柱色谱方法对南湖菱果壳进行了系统的化学成分研究,从中分离得到12个化合物,鉴定了其中9个,分别为：4,23,24-三甲基胆甾-22-烯-3-醇(1),豆甾醇(2),α-香树脂醇(4), (E)-bis-4,4'-(3-ethenyl-1-propene-1,3-diyl)-phenol (5),齐墩果酸(7),熊果酸(8),常春藤皂苷元(9),3,23-二羟基-12-烯-28-乌苏酸(10),β-胡萝卜苷(12),化合物1、2、4、5、7、8、9、10和12均为首次从该植物中分离得到。
二、采用DPPH、ABTS和FRAP 3种方法综合评价南湖菱果壳各提取物的体外抗氧化活性,发现其甲醇-水提取物、石油醚部位、乙酸乙酯部位和正丁醇部位均具有较好的抗氧化活性,其中乙酸乙酯部位活性最高。
三、采用96微孔板法对南湖菱果壳各提取物进行体外抑制a-葡萄糖苷酶活性筛选,发现其甲醇-水提取物(IC50=2.00μg·mL-1)、石油醚部位(IC50=14.4μg·mL-1)、乙酸乙酯部位(IC50=0.4μg·mL-1)和正丁醇部位(IC50=1.00μg·mL-1)均具有显著的α-葡萄糖苷酶抑制活性,远高于阳性对照Acarbose (IC50=1103.01μg·mL-1)。
四、研究了南湖菱果壳各提取物体外抑制SA, MRSA和ESBLs-SA活性,发现其甲醇-水提取物、石油醚部位、乙酸乙酯部位和正丁醇部位对SA, MRSA和ESBLs-SA均有抑制作用。其中甲醇-水提取物(IC50=0.46 mg·mL-1)对SA的抑制效果最好,石油醚部位对MRSA (IC50=0.62 mg·mL-1)和ESBLs-SA (IC50=0.34 mg·mL-1)的抑制作用最好。甲醇-水和石油醚提取物是其表现抗菌效果的活性部位。
第三章菱科菱属植物研究进展
本章从化学成分和药理作用两方面对菱科菱属植物的研究现状进行了综述,以期对其进行更好的开发利用。
This dissertation is composed of three chapters. The first chapter showed the isolation and identification of compounds from rhizomes and flowers of Musa basjoo Sieb. et Zucc, and the antioxidant, a-glucosidase inhibitory as well as anti-bacterias activity of different extracts and compounds were introduced. The second chapter studied the isolation and identification of compounds from Trapa acornis Nakano, besides, the antioxidant, a-glucosidase inhibitory and anti-bacterias activity of different extracts and compounds were reported. The third chapter summarized the study progress of chemical constituent and pharmaceutical of the genus Trapa.
Chapter 1. The chemical constituents and bioactivities of rhizomes and
flowers of Musa basjoo Sieb. et Zucc
1. The chemical constituents from the rhizomes and flowers of Musa basjoo Sieb. et Zucc were studied by column chromatography. Seven compounds were isolated from the rhizomes of M. basjoo and identified as 2',3,4'-Trihydroxyflavone (1),3,3'-bis-hydroxyanigorufone (2), Stigmasterol(3), Irenolone (4), 2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone (5),3,4-dihydroxybenzaldehyde (6) andβ-daucosterol (7). Compound 1、2、4、5、6 were isolated from this plant for the first time. Compound 6 was isolated from Musa genus for the first time. Eight compounds were isolated from the flowers of M. basjoo, two compounds were identified as Stigmasterol(4) andβ-daucosterol (7). Compound 4 and 7 were isolated from this plant for the first time.
2. DPPH, ABTS, and FRAP assays were used to screen the antioxidant activity of rhizomes and flowers of M. basjoo. Different extracts from the rhizomes of M. basjoo showed better antioxidant activity, but the extracts from flowers didn't have the activity. The activity of compounds was screened by scavenging activity against DPPH. radical with microplate assay. 2',3,4'-Trihydroxyflavone (IC50=8.61μg·mL-1), Irenolone(IC50=19.55μg·mL-1) and 3,4-dihydroxybenzaldehyde(IC50=1.1μg·mL-1) exhibited strong activity.
3. The inhibitory effect against a-glucosidase of different extracts and compounds from rhizomes and flowers of M. basjoo were screened in a 96-well plate. Petroleum ether, EtOAC, MeOH extracts of the rhizomes and petroleum ether extracts of the flowers showed stronger inhibitory effect against a-glucosidase, and petroleum ether extracts of the flowers was the highest.3,3'-bis-hydroxyanigorufone (IC50=24.15μg·mL-1) and 2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone (IC50=2.81μg·mL-1) exhibited stronger inhibitory activity,which were much higher than that of acarbose (IC50=1103.01μg·mL-1)
4. Antibacterial activity of different extracts and compounds from rhizomes and flowers of M. basjoo were assayed by using Staphylococcus aureus(SA), methicillin-resistant Staphylococcus aureus (MRSA) andβ-lactamase positive Staphylococcus aureus(ESBLs-SA). Petroleum ether extracts of rhizome and flower were active fraction.2,4-dihydroxy-9-(4'-hydroxyphenyl)-phenalenone showed strong activity with MIC value of 0.078,0.313,0.039μg/disc against SA, MRSA and ESBLs-SA respectively.
Chapter 2. The chemical constituents and bioactivities of Trapa acornis Nakano
1. The chemical constituents from the nutshell of Trapa acornis Nakano were studied by column chromatography. Twelve compounds were isolated and nine were identified as 4,23,24-trimethylcholest-22-en-3-ol(1), Stigmasterol(2), a-amyrin(4), (E)-bis-4,4'-(3-ethenyl-l-propene-1,3-diyl)-phenol (5), oleanolic acid(7), ursolic acid(8), Hederagenin(9), 3,23-dihydroxy-12-ursen-28-oic acid(10) andβ-daucosterol(12). Compound 1,2,4,5,7,8,9,10 and 12 were isolated from this plant for the first time.
2. The antioxidant activity of different extracts of nueshell of T. acornis was screened by the DPPH, ABTS, and FRAP assays. The MeOH/water, petroleum ether, EtOAC and n-butyl alcohol extracts showed better antioxidant activity, and the EtOAC extracts was the highest.
3. The inhibitory effect against a-glucosidase of different extracts from nutshell of T. acornis were screened in a 96-well plate. MeOH/water (IC50=2.00μg·mL-1), petroleum ether (IC50=14.4μg·mL-1), EtOAC (IC50=0.4μg·mL-1) and n-butyl alcohol (IC50=1.00μg·mL-1) extracts showed stronger inhibitory effect against a-glucosidase, which were much higher than that of acarbose (IC50=1103.01μg·mL-1)
4. Antibacterial activity againet Staphylococcus aureus(SA), methicillin-resistant Staphylococcus aureus (MRSA) andβ-Mactamase positive Staphylococcus aureus(ESBLs-SA) of different extracts from nutshell of T. acornis were assayed. The MeOH/water, petroleum ether, EtOAC and n-butyl alcohol extracts exhibited antibacterial activity. The MeOH/water extracts displayed the best antibacterial activity of SA with IC50 value of 0.46 mg-mL-1. Petroleum ether extract showed the best antibacterial activity of MRSA and ESBLs-SA with IC50 value of 0.62, 0.34 mg-mL-1 respectively. The antibacterial activity ingredients mainly in the MeOH/water and petroleum ether extracts.
Chapter 3. The study progress of chemical constituent and pharmaceutical of the genus Trapa
The study progress of chemical constituent and pharmaceutical of the genus Trapa were summarized.
引文
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