毛酸浆浆果的化学成分研究
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摘要
毛酸浆Physalis pubescens L.为茄科Solanaceae酸浆属Physalis L.的一年生草本植物，《神农本草经》最早收录，并列为中品。其带浆果的宿萼或全草称为灯笼草，灯笼草全草及果实均可入药，具有清热解毒，化痰利尿的作用，是常用的清热解毒药。酸浆属植物主要含甾体类、生物碱类、黄酮类、有机酸类、脂类等。本文在综述酸浆属植物的化学成分，药理活性及用途的基础上，利用反复硅胶柱色谱法、SephadexLH-20凝胶柱色谱法、半制备高效液相色谱等方法分离纯化；通过核磁共振谱、质谱等色谱数据鉴定化合物结构。本实验从毛酸浆浆果中分离得到26个化合物，分别鉴定为3,7,3'-三甲基槲皮素(SG-1)、山奈酚(SG-2)、金圣草黄素(SG-3)、槲皮素-3-O-β-D-吡喃葡萄糖苷(SG-4)、2α,3β,23-三羟基-12-烯-28-齐墩果酸(SG-5)、白头翁皂苷A(SG-6)、白头翁皂苷D(SG-7)、blumenolA (SG-8)、咖啡酸(SG-9)、1-O-咖啡酰基-β-D-吡喃葡萄糖(SG-10)、β-D-吡喃葡萄糖氧基丁香酸酯(SG-11)、咖啡酰基奎宁酸正丁酯(SG-12)、对羟基肉桂酸吡喃葡萄糖苷(SG-13)、1'-O-β-D-(3,4-二羟基苯乙基)-4'-O-咖啡酰基葡萄糖苷(SG-14)、4-羟基-3-甲氧基苯甲酸(SG-15)、1-O-p-阿魏酰基-β-D-吡喃葡萄糖苷(SG-16)、N-反式-对羟基苯乙基阿魏酸酰胺(SG-17)、新橄榄脂素(SG-18)、梣皮树脂醇(SG-19)、松脂醇(SG-20)、蔗糖(SG-21)、尿苷(SG-22)、腺苷(SG-23)、去甲络石苷元(SG-24)、β-谷甾醇(SG-25)、β-胡萝卜苷(SG-26)。其中SG-5~SG-8、SG-10、SG-11、SG-13~SG-24为首次从酸浆属植物中分离得到，化合物SG-3、SG-4、SG-9、SG-12为首次从毛酸浆植物中分离得到。
本实验对毛酸浆浆果醇提物及单体进行抗菌、抗氧化、抗肿瘤活性筛选，SG-20在剂量为0.016μmol/mL-0.256μmol/mL时对SMMC-7721肝癌细胞抑制率为23.58%-49.21%。SG-11在剂量浓度为0.0087μmol/mL-0.0348μmol/mL时对A549肺癌细胞抑制率为10.66%-26.86%，SG-20在剂量浓度为0.0022μmol/mL-0.0344μmol/mL时对A549肺癌细胞抑制率为22.74%-52.48%。
毛酸浆浆果醇提物经减压硅胶(60-100目)柱层析，得到的70%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为16.95%-91.53%，50%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为3.39%-71.19%，30%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为1.69%-67.80%，浆果醇提物在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为26.35%-92.96%。清除能力顺序为浆果醇提物>70%甲醇部位>50%甲醇部位>30%甲醇部位。70%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为12.89%-90.42%，50%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为5.13%-68.80%，30%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为4.32%-65.77%，浆果醇提物在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为23.65%-92.58%。清除能力顺序为浆果醇提物>70%甲醇部位>50%甲醇部位>30%甲醇部位。
毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，绿脓杆菌菌落数为106CFU/mL时的抑菌圈值为4.0mm-5.9mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，金黄色葡萄球菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-6.2mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，白色念球菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-5.3mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，枯草杆菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-6.1mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，大肠杆菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-6.4mm。
本实验初步阐明毛酸浆浆果的药理活性，为天然药物化学和现代中药药理提供了研究资料，此外毛酸浆浆果有望作为天然氧化剂和功能性食品得到开发。
本论文的研究工作为天然资源的开发利用提供重要的理论依据，并对中草药活性成分研究，新药筛选等提供科学依据。
Physalis pubeacens L. has long been a minor fruit of China and has also been grownin America. The fruit of the Physalis Genus was also extensively used as herb medicine,and had the effects of detoxification and anti-inflammation in traditional Chinese medicine.the extract of fruits of the Physalis Genus had been reported to have potent antioxidant,anti-inflammatory, and cytotoxic activities. Previous studies on constituents from thePhysalis genus led to the isolation of different compounds such as triterpenoids, flavones,alkaloids and steroids.
During the course of our investigation for bioactive agents from the EtOH extract ofcalyxs of Physalis pubeacens L.,30compounds were obtained by using silica gel columnchromatography, Sephadex LH-20chromatography, MPLC, and Semi-HPLC, andstructures of26compounds were elucidated through spectroscopic analysis (NMR, MSand IR). Their structures were identified to be3,7,3'-trimethylquercetin (SG-1),kaempferol (SG-2), chrysoeriol (SG-3), quercetin-3-O-β-D-glucopyranoside (SG-4),arjunolic acid (SG-5), pulsatilla saponin A (SG-6), pulsatilla saponin D (SG-7),blumenolA (SG-8), caffeic acid (SG-9),1-O-caffeoyl-β-D-glucopyranoside (SG-10),syringic acid β-D-glucopyranosyl ester (SG-11),5-O-caffeoyl quinic acid butyl ester(SG-12),1-p-coumaroyl-β-D-glucopyranoside(SG-13), Calceolarioside A(SG-14),4-hydroxyl-3-methoxyl-benzoicacid(SG-15),1-O-p-feruloyl-β-D-glucopyranoside(SG-16), N-trans-p-hydroxyphenethylferolamine (SG-17), neo-olivil (SG-18),medioresinol (SG-19), pinoresinol (SG-20), sucrose (SG-21), uridine (SG-22), adenosine(SG-23), northrachelogenin (SG-24), β-sitosterol (SG-25), daucosterol (SG-26)。Amongthem, SG-5~SG-8,SG-10,SG-11,SG-13~SG-24were isolated from this genus for the firsttime. Compounds SG-3,SG-4and SG-12were obtained from this plant for the first time.
The antibacterial, antioxidation and antitumor activitis of compounds and extract were screened, SG-20at a dose of0.016μmol/mL-0.256μmol/mL,SMMC-7721hepatomacell inhibition was23.58%-49.21%. SG-11at a dose of0.0087μmol/mL-0.0348μmol/mL,A549lung cancer cells inhibition was10.66%-26.86%.SG-20at dose of0.0022μmol/mL-0.0344μmol/mL,A549lung cancer cell inhibition was22.74%-52.48%..
ABTS free radical clearance of70%methanol parts of the berries was16.95%-91.53%,when the concentration was between0.0625mg/mL–4mg/mL, ABTS freeradical clearance of50%methanol parts of the berries was3.39%-71.19%,when theconcentration was between0.0625mg/mL–4mg/mL, ABTS free radical clearance of30%methanol parts of the berries was1.69%-67.80%,when the concentration wasbetween0.0625mg/mL-4mg/mL. ABTS free radical clearance of70%methanol parts ofthe berries was26.35%-92.96%,when the concentration was between0.0625mg/mL~4mg/mL,Sort of clearance was the alcohol extracts>70%methanol parts>50%methanolparts>30%methanol parts. DPPH free radical clearance of70%methanol parts of theberries was12.89%-90.42%,when the concentration was between0.0625mg/mL-4mg/mL, DPPH free radical clearance of50%methanol parts of the berries was5.13%-68.80%,when the concentration was between0.0625mg/mL-4mg/mL, DPPH free radicalclearance of30%methanol parts of the berries was4.32%-65.77%,when theconcentration was between0.0625mg/mL–4mg/mL. DPPH free radical clearance of70%methanol parts of the berries was26.35%-92.96,when the concentration was between0.0625mg/mL~4mg/mL,Sort of clearance was the alcohol extracts>70%methanol parts>50%methanol parts>30%methanol parts.
The scope of bacteriostatic ring was4.0mm-5.9mm,when the berries of Physalispubeacens L.ethanol extract concentrationwas between12.5mg/mL-100mg/mL,and thePseudomonas aeruginosa was106CFU/mL. The scope of bacteriostatic ring was4.0mm-6.2mm, when the berries of Physalis pubeacens L.ethanol extract concentrationwasbetween12.5mg/mL-100mg/mL,and the Staphylococcus aureus was106CFU/mL.Thescope of bacteriostatic ring was4.0mm-5.3mm, when the berries of Physalispubeacens L.ethanol extract concentrationwas between12.5mg/mL-100mg/mL,and theStaphylococcus aureus was106CFU/mL, The scope of bacteriostatic ring was4.0mm-6.1 mm,when the berries of Physalis pubeacens L.ethanol extract concentrationwas between12.5mg/mL-100mg/mL,and the Bacillus subtilis was106CFU/mL. The scope ofbacteriostatic ring was4.0mm-6.4mm.,when the berries of Physalis pubeacens L.ethanolextract concentrationwas between12.5mg/mL-100mg/mL,and the E. coli was106CFU/mL.
This study provided research data for natural medicine and modern Chinese medicinepharmacological,in order to achieve the purpose to rational drug use,and broaden its scopeof application, And it could be employed as natural antioxidants and health care products.
本实验对毛酸浆浆果醇提物及单体进行抗菌、抗氧化、抗肿瘤活性筛选，SG-20在剂量为0.016μmol/mL-0.256μmol/mL时对SMMC-7721肝癌细胞抑制率为23.58%-49.21%。SG-11在剂量浓度为0.0087μmol/mL-0.0348μmol/mL时对A549肺癌细胞抑制率为10.66%-26.86%，SG-20在剂量浓度为0.0022μmol/mL-0.0344μmol/mL时对A549肺癌细胞抑制率为22.74%-52.48%。
毛酸浆浆果醇提物经减压硅胶(60-100目)柱层析，得到的70%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为16.95%-91.53%，50%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为3.39%-71.19%，30%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为1.69%-67.80%，浆果醇提物在剂量浓度为0.0625mg/mL-4mg/mL时对ABTS自由基清除率为26.35%-92.96%。清除能力顺序为浆果醇提物>70%甲醇部位>50%甲醇部位>30%甲醇部位。70%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为12.89%-90.42%，50%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为5.13%-68.80%，30%甲醇部位在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为4.32%-65.77%，浆果醇提物在剂量浓度为0.0625mg/mL-4mg/mL时对DPPH自由基清除率为23.65%-92.58%。清除能力顺序为浆果醇提物>70%甲醇部位>50%甲醇部位>30%甲醇部位。
毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，绿脓杆菌菌落数为106CFU/mL时的抑菌圈值为4.0mm-5.9mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，金黄色葡萄球菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-6.2mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，白色念球菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-5.3mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，枯草杆菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-6.1mm。毛酸浆浆果醇提物在浓度为12.5mg/mL-100mg/mL，大肠杆菌在菌落数为106CFU/mL时的抑菌圈值为4.0mm-6.4mm。
本实验初步阐明毛酸浆浆果的药理活性，为天然药物化学和现代中药药理提供了研究资料，此外毛酸浆浆果有望作为天然氧化剂和功能性食品得到开发。
本论文的研究工作为天然资源的开发利用提供重要的理论依据，并对中草药活性成分研究，新药筛选等提供科学依据。
Physalis pubeacens L. has long been a minor fruit of China and has also been grownin America. The fruit of the Physalis Genus was also extensively used as herb medicine,and had the effects of detoxification and anti-inflammation in traditional Chinese medicine.the extract of fruits of the Physalis Genus had been reported to have potent antioxidant,anti-inflammatory, and cytotoxic activities. Previous studies on constituents from thePhysalis genus led to the isolation of different compounds such as triterpenoids, flavones,alkaloids and steroids.
During the course of our investigation for bioactive agents from the EtOH extract ofcalyxs of Physalis pubeacens L.,30compounds were obtained by using silica gel columnchromatography, Sephadex LH-20chromatography, MPLC, and Semi-HPLC, andstructures of26compounds were elucidated through spectroscopic analysis (NMR, MSand IR). Their structures were identified to be3,7,3'-trimethylquercetin (SG-1),kaempferol (SG-2), chrysoeriol (SG-3), quercetin-3-O-β-D-glucopyranoside (SG-4),arjunolic acid (SG-5), pulsatilla saponin A (SG-6), pulsatilla saponin D (SG-7),blumenolA (SG-8), caffeic acid (SG-9),1-O-caffeoyl-β-D-glucopyranoside (SG-10),syringic acid β-D-glucopyranosyl ester (SG-11),5-O-caffeoyl quinic acid butyl ester(SG-12),1-p-coumaroyl-β-D-glucopyranoside(SG-13), Calceolarioside A(SG-14),4-hydroxyl-3-methoxyl-benzoicacid(SG-15),1-O-p-feruloyl-β-D-glucopyranoside(SG-16), N-trans-p-hydroxyphenethylferolamine (SG-17), neo-olivil (SG-18),medioresinol (SG-19), pinoresinol (SG-20), sucrose (SG-21), uridine (SG-22), adenosine(SG-23), northrachelogenin (SG-24), β-sitosterol (SG-25), daucosterol (SG-26)。Amongthem, SG-5~SG-8,SG-10,SG-11,SG-13~SG-24were isolated from this genus for the firsttime. Compounds SG-3,SG-4and SG-12were obtained from this plant for the first time.
The antibacterial, antioxidation and antitumor activitis of compounds and extract were screened, SG-20at a dose of0.016μmol/mL-0.256μmol/mL,SMMC-7721hepatomacell inhibition was23.58%-49.21%. SG-11at a dose of0.0087μmol/mL-0.0348μmol/mL,A549lung cancer cells inhibition was10.66%-26.86%.SG-20at dose of0.0022μmol/mL-0.0344μmol/mL,A549lung cancer cell inhibition was22.74%-52.48%..
ABTS free radical clearance of70%methanol parts of the berries was16.95%-91.53%,when the concentration was between0.0625mg/mL–4mg/mL, ABTS freeradical clearance of50%methanol parts of the berries was3.39%-71.19%,when theconcentration was between0.0625mg/mL–4mg/mL, ABTS free radical clearance of30%methanol parts of the berries was1.69%-67.80%,when the concentration wasbetween0.0625mg/mL-4mg/mL. ABTS free radical clearance of70%methanol parts ofthe berries was26.35%-92.96%,when the concentration was between0.0625mg/mL~4mg/mL,Sort of clearance was the alcohol extracts>70%methanol parts>50%methanolparts>30%methanol parts. DPPH free radical clearance of70%methanol parts of theberries was12.89%-90.42%,when the concentration was between0.0625mg/mL-4mg/mL, DPPH free radical clearance of50%methanol parts of the berries was5.13%-68.80%,when the concentration was between0.0625mg/mL-4mg/mL, DPPH free radicalclearance of30%methanol parts of the berries was4.32%-65.77%,when theconcentration was between0.0625mg/mL–4mg/mL. DPPH free radical clearance of70%methanol parts of the berries was26.35%-92.96,when the concentration was between0.0625mg/mL~4mg/mL,Sort of clearance was the alcohol extracts>70%methanol parts>50%methanol parts>30%methanol parts.
The scope of bacteriostatic ring was4.0mm-5.9mm,when the berries of Physalispubeacens L.ethanol extract concentrationwas between12.5mg/mL-100mg/mL,and thePseudomonas aeruginosa was106CFU/mL. The scope of bacteriostatic ring was4.0mm-6.2mm, when the berries of Physalis pubeacens L.ethanol extract concentrationwasbetween12.5mg/mL-100mg/mL,and the Staphylococcus aureus was106CFU/mL.Thescope of bacteriostatic ring was4.0mm-5.3mm, when the berries of Physalispubeacens L.ethanol extract concentrationwas between12.5mg/mL-100mg/mL,and theStaphylococcus aureus was106CFU/mL, The scope of bacteriostatic ring was4.0mm-6.1 mm,when the berries of Physalis pubeacens L.ethanol extract concentrationwas between12.5mg/mL-100mg/mL,and the Bacillus subtilis was106CFU/mL. The scope ofbacteriostatic ring was4.0mm-6.4mm.,when the berries of Physalis pubeacens L.ethanolextract concentrationwas between12.5mg/mL-100mg/mL,and the E. coli was106CFU/mL.
This study provided research data for natural medicine and modern Chinese medicinepharmacological,in order to achieve the purpose to rational drug use,and broaden its scopeof application, And it could be employed as natural antioxidants and health care products.
引文
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