Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L.
Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L.
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DOI：
10.1055/s-2007-967167
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发表时间：
2007-05-01
期刊：
影响因子：
2.7
通讯作者：
Ferreira, Daneel
中科院分区：
文献类型：
--
作者：
Reddy, Muntha K.;Gupta, Sashi K.;Ferreira, Daneel
将石榴副产物POMx分为水、乙酸乙酯（EtOAc）和正丁醇（n-BuOH），用XAD-16和Sephadex LH-20柱层析纯化乙酸乙酯（EtOAc）和正丁醇（n-BuOH）提取物，得到鞣花酸(1)、没食子酸(2)、石榴苷(3)和石榴苷(4)。化合物1 -4和单宁组分混合物（XAD-16洗脱物）在细胞基础上评估了抗氧化、抗疟原虫和抗菌活性。单宁（TPT）、XADEtOAc、XAD-H2O、XAD-PJ和XAD-BuOH的混合物对活性氧（ROS）产生的IC50值为0.8 ~ 19 μ g/ mL，化合物1 ~ 4对ROS产生的IC50值分别为1.1、3.2、2.3和1.4 μ M，对HL-60细胞的毒性高达31.25 μ M /mL。没食子酸(2)和果酸素(4)对恶性疟原虫D6和W2克隆具有抗疟原虫活性，IC50值分别为10.9、10.6、7.5和8.9 μ M。XAD-EtOAc、XAD-BuOH、XAD-H2O和XAD-PJ化合物1-4对大肠埃希菌、铜绿假单胞菌、白色念珠菌、新型隐球菌、耐甲氧西林金黄色葡萄球菌（MRSA）、烟曲霉和细胞内分枝杆菌具有抑菌活性。化合物2和4对铜绿假单胞菌、新生假单胞菌和MRSA均有抑制作用。本文首次报道了POMx分离物的抗氧化、抗疟原虫和抗菌活性，包括化合物1 ~ 4自由基抑制活性的构效关系（SAR）。我们的研究结果表明，每天摄入POMx和石榴汁（PJ）作为膳食补充剂，可以增强人体免疫系统的抗氧化、抗疟疾和抗菌能力。将石榴副产物POMx分为水、乙酸乙酯（EtOAc）和正丁醇（n-BuOH），用XAD-16和Sephadex LH-20柱层析纯化乙酸乙酯（EtOAc）和正丁醇（n-BuOH）提取物，得到鞣花酸(1)、没食子酸(2)、石榴苷(3)和石榴苷(4)。化合物1 -4和单宁组分混合物（XAD-16洗脱物）在细胞基础上评估了抗氧化、抗疟原虫和抗菌活性。单宁（TPT）、XADEtOAc、XAD-H2O、XAD-PJ和XAD-BuOH的混合物对活性氧（ROS）产生的IC50值为0.8 ~ 19 μ g/ mL，化合物1 ~ 4对ROS产生的IC50值分别为1.1、3.2、2.3和1.4 μ M，对HL-60细胞的毒性高达31.25 μ M /mL。没食子酸(2)和果酸素(4)对恶性疟原虫D6和W2克隆具有抗疟原虫活性，IC50值分别为10.9、10.6、7.5和8.9 μ M。XAD-EtOAc、XAD-BuOH、XAD-H2O和XAD-PJ化合物1-4对大肠埃希菌、铜绿假单胞菌、白色念珠菌、新型隐球菌、耐甲氧西林金黄色葡萄球菌（MRSA）、烟曲霉和细胞内分枝杆菌具有抑菌活性。化合物2和4对铜绿假单胞菌、新生假单胞菌和MRSA均有抑制作用。本文首次报道了POMx分离物的抗氧化、抗疟原虫和抗菌活性，包括化合物1 ~ 4自由基抑制活性的构效关系（SAR）。我们的研究结果表明，每天摄入POMx和石榴汁（PJ）作为膳食补充剂，可以增强人体免疫系统的抗氧化、抗疟疾和抗菌能力。
The Punica granatum L (pomegranate) by-product POMx was partitioned between water, EtOAc and n-BuOH, and the EtOAc and n-BuOH extracts were purified by XAD-16 and Sephadex LH-20 column chromatography to afford ellagic acid (1), gallagic acid (2), punicalins (3), and punicalagins (4). Compounds 1 -4 and the mixture of tannin fractions (XAD-16 eluates) were evaluated for antioxidant, antiplasmodial, and antimicrobial activities in cell-based assays. The mixture of tannins (TPT), XADEtOAc, XAD-H2O, XAD-PJ and XAD-BuOH, exhibited IC50 values against reactive oxygen species (ROS) generation at 0.8 - 19 mu g/ mL. Compounds 1 - 4 showed IC50 values of 1.1, 3.2, 2.3 and 1.4 mu M, respectively, against ROS generation and no toxicity up to 31.25 mu/mL against HL-60 cells. Gallagic acid (2) and punicalagins (4) exhibited antiplasmodial activity against Plastriodium falciparum D6 and W2 clones with IC50 values of 10.9,10.6, 7.5 and 8.9 mu M, respectively. Fractions XAD-EtOAc, XAD-BuOH, XAD-H2O and XAD-PJ compounds 1-4 revealed antimicrobial activity when assayed against Escherichia coli, Pseudomonas aeruginosa, Candida albicans, Cryptococcus neoformans, methicillin-resistant Staphylococcus aureus (MRSA),Aspergillus fumigatus and Mycobacterium intracellulare. Compounds 2 and 4 showed activity against P. aeruginosa, C. neoformans, and MRSA. This is the first report on the antioxidant, antiplasmodial and antimicrobial activities of POMx isolates, including structure-activity relationships (SAR) of the free radical inhibition activity of compounds 1 -4. Our results suggest a beneficial effect from the daily intake of POMx and pomegranate juice (PJ) as dietary supplements to augment the human immune system's antioxidant, antimalarial and antimicrobial capacities.The Punica granatum L (pomegranate) by-product POMx was partitioned between water, EtOAc and n-BuOH, and the EtOAc and n-BuOH extracts were purified by XAD-16 and Sephadex LH-20 column chromatography to afford ellagic acid (1), gallagic acid (2), punicalins (3), and punicalagins (4). Compounds 1 -4 and the mixture of tannin fractions (XAD-16 eluates) were evaluated for antioxidant, antiplasmodial, and antimicrobial activities in cell-based assays. The mixture of tannins (TPT), XADEtOAc, XAD-H2O, XAD-PJ and XAD-BuOH, exhibited IC50 values against reactive oxygen species (ROS) generation at 0.8 - 19 mu g/ mL. Compounds 1 - 4 showed IC50 values of 1.1, 3.2, 2.3 and 1.4 mu M, respectively, against ROS generation and no toxicity up to 31.25 mu/mL against HL-60 cells. Gallagic acid (2) and punicalagins (4) exhibited antiplasmodial activity against Plastriodium falciparum D6 and W2 clones with IC50 values of 10.9,10.6, 7.5 and 8.9 mu M, respectively. Fractions XAD-EtOAc, XAD-BuOH, XAD-H2O and XAD-PJ compounds 1-4 revealed antimicrobial activity when assayed against Escherichia coli, Pseudomonas aeruginosa, Candida albicans, Cryptococcus neoformans, methicillin-resistant Staphylococcus aureus (MRSA),Aspergillus fumigatus and Mycobacterium intracellulare. Compounds 2 and 4 showed activity against P. aeruginosa, C. neoformans, and MRSA. This is the first report on the antioxidant, antiplasmodial and antimicrobial activities of POMx isolates, including structure-activity relationships (SAR) of the free radical inhibition activity of compounds 1 -4.Our results suggest a beneficial effect from the daily intake of POMx and pomegranate juice (PJ) as dietary supplements to augment the humanimmune system's antioxidant, antimalarial and antimicrobial capacities.