Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L
Abstract 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). Compo...
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| Veröffentlicht in: | Planta medica 2007-05, Vol.73 (5), p.461-467 |
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| creator | Reddy, M.K Gupta, S.K Jacob, M.R Khan, S.I Ferreira, D |
| description | Abstract
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), XAD-EtOAc, XAD-H
2
O, XAD-PJ and XAD-BuOH, exhibited IC
50
values against reactive oxygen species (ROS) generation at 0.8 - 19 μg/mL. Compounds 1 - 4 showed IC
50
values of 1.1, 3.2, 2.3 and 1.4 μM, respectively, against ROS generation and no toxicity up to 31.25 μg/mL against HL-60 cells. Gallagic acid (2) and punicalagins (4) exhibited antiplasmodial activity against PLASMODIUM FALCIPARUM D6 and W2 clones with IC
50
values of 10.9, 10.6, 7.5 and 8.8 μM, respectively. Fractions XAD-EtOAc, XAD-BuOH, XAD-H
2
O 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. |
| doi_str_mv | 10.1055/s-2007-967167 |
| format | Article |
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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), XAD-EtOAc, XAD-H
2
O, XAD-PJ and XAD-BuOH, exhibited IC
50
values against reactive oxygen species (ROS) generation at 0.8 - 19 μg/mL. Compounds 1 - 4 showed IC
50
values of 1.1, 3.2, 2.3 and 1.4 μM, respectively, against ROS generation and no toxicity up to 31.25 μg/mL against HL-60 cells. Gallagic acid (2) and punicalagins (4) exhibited antiplasmodial activity against PLASMODIUM FALCIPARUM D6 and W2 clones with IC
50
values of 10.9, 10.6, 7.5 and 8.8 μM, respectively. Fractions XAD-EtOAc, XAD-BuOH, XAD-H
2
O 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.</description><identifier>ISSN: 0032-0943</identifier><identifier>EISSN: 1439-0221</identifier><identifier>DOI: 10.1055/s-2007-967167</identifier><identifier>PMID: 17566148</identifier><identifier>CODEN: PLMEAA</identifier><language>eng</language><publisher>Stuttgart: Thieme</publisher><subject><![CDATA[Animals ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - isolation & purification ; Anti-Infective Agents - pharmacology ; antibacterial properties ; antifungal properties ; antimalarials ; Antimalarials - chemistry ; Antimalarials - isolation & purification ; Antimalarials - pharmacology ; antioxidant activity ; Antioxidants - chemistry ; Antioxidants - isolation & purification ; Antioxidants - pharmacology ; Biological and medical sciences ; Chemical Fractionation ; ellagic acid ; ellagitannin ; gallagic acid ; General pharmacology ; HL-60 Cells ; Humans ; Hydrolyzable Tannins - chemistry ; Hydrolyzable Tannins - isolation & purification ; Hydrolyzable Tannins - pharmacology ; Hydroxybenzoates - chemistry ; Hydroxybenzoates - isolation & purification ; Hydroxybenzoates - pharmacology ; Lythraceae ; Medical sciences ; medicinal plants ; Microbial Sensitivity Tests ; Original Paper ; Pharmacognosy. Homeopathy. Health food ; Pharmacology. Drug treatments ; phenolic acids ; phytochemicals ; Plant Extracts - chemistry ; Plant Extracts - isolation & purification ; Plasmodium falciparum ; Plasmodium falciparum - drug effects ; Punica granatum ; Punicaceae - chemistry ; punicalagin ; punicalin ; reactive oxygen species ; Reactive Oxygen Species - metabolism ; tannins]]></subject><ispartof>Planta medica, 2007-05, Vol.73 (5), p.461-467</ispartof><rights>Georg Thieme Verlag KG Stuttgart · New York</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c448t-900131eae129266332be894833e2b964e6fb462bf6c03a7ae2917304b1b12fec3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2007-967167.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-2007-967167$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,777,781,3004,3005,27905,27906,54540,54541</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18773247$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17566148$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Reddy, M.K</creatorcontrib><creatorcontrib>Gupta, S.K</creatorcontrib><creatorcontrib>Jacob, M.R</creatorcontrib><creatorcontrib>Khan, S.I</creatorcontrib><creatorcontrib>Ferreira, D</creatorcontrib><title>Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L</title><title>Planta medica</title><addtitle>Planta Med</addtitle><description>Abstract
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), XAD-EtOAc, XAD-H
2
O, XAD-PJ and XAD-BuOH, exhibited IC
50
values against reactive oxygen species (ROS) generation at 0.8 - 19 μg/mL. Compounds 1 - 4 showed IC
50
values of 1.1, 3.2, 2.3 and 1.4 μM, respectively, against ROS generation and no toxicity up to 31.25 μg/mL against HL-60 cells. Gallagic acid (2) and punicalagins (4) exhibited antiplasmodial activity against PLASMODIUM FALCIPARUM D6 and W2 clones with IC
50
values of 10.9, 10.6, 7.5 and 8.8 μM, respectively. Fractions XAD-EtOAc, XAD-BuOH, XAD-H
2
O 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.</description><subject>Animals</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - isolation & purification</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>antibacterial properties</subject><subject>antifungal properties</subject><subject>antimalarials</subject><subject>Antimalarials - chemistry</subject><subject>Antimalarials - isolation & purification</subject><subject>Antimalarials - pharmacology</subject><subject>antioxidant activity</subject><subject>Antioxidants - chemistry</subject><subject>Antioxidants - isolation & purification</subject><subject>Antioxidants - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Chemical Fractionation</subject><subject>ellagic acid</subject><subject>ellagitannin</subject><subject>gallagic acid</subject><subject>General pharmacology</subject><subject>HL-60 Cells</subject><subject>Humans</subject><subject>Hydrolyzable Tannins - chemistry</subject><subject>Hydrolyzable Tannins - isolation & purification</subject><subject>Hydrolyzable Tannins - pharmacology</subject><subject>Hydroxybenzoates - chemistry</subject><subject>Hydroxybenzoates - isolation & purification</subject><subject>Hydroxybenzoates - pharmacology</subject><subject>Lythraceae</subject><subject>Medical sciences</subject><subject>medicinal plants</subject><subject>Microbial Sensitivity Tests</subject><subject>Original Paper</subject><subject>Pharmacognosy. Homeopathy. Health food</subject><subject>Pharmacology. Drug treatments</subject><subject>phenolic acids</subject><subject>phytochemicals</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - isolation & purification</subject><subject>Plasmodium falciparum</subject><subject>Plasmodium falciparum - drug effects</subject><subject>Punica granatum</subject><subject>Punicaceae - chemistry</subject><subject>punicalagin</subject><subject>punicalin</subject><subject>reactive oxygen species</subject><subject>Reactive Oxygen Species - metabolism</subject><subject>tannins</subject><issn>0032-0943</issn><issn>1439-0221</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kMtOwzAQRS0EoqWwZAvZsKvBr9jJsqp4SZVAgq6jieu0rhKnslMEf8Bn4zaVumJjyzPHd-ZehK4puackTR8CZoQonEtFpTpBQyp4jglj9BQNCeEMk1zwAboIYU0IFTkh52hAVSolFdkQ_U5cZ9tvuwDXjZN42AZq8Bbq-Fj0Bat9W-4rurNftrMmJG2VdOCcddhbvUoqv-u1LowTU9ewtH0z7EU2K-Pa2ur43y5CZNsmed86qyFZenDQbZtkdonOKqiDuTrcIzR_evycvuDZ2_PrdDLDWoisw3F_yqkBQ1nOpOSclSbLRca5YWUuhZFVKSQrK6kJBwWG5VRxIkpaUlYZzUcI97rRVAjeVMXGR8_-p6Ck2CVahGKXaNEnGvmbnt9sy8YsjvQhwgjcHQAIGuqYhNM2HLlMKc7ETmjcc93KmsYU63brXXT679zbHq-gLWDpo-T8g0XzkclSqVL-B2YPlxI</recordid><startdate>20070501</startdate><enddate>20070501</enddate><creator>Reddy, M.K</creator><creator>Gupta, S.K</creator><creator>Jacob, M.R</creator><creator>Khan, S.I</creator><creator>Ferreira, D</creator><general>Thieme</general><scope>FBQ</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20070501</creationdate><title>Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L</title><author>Reddy, M.K ; Gupta, S.K ; Jacob, M.R ; Khan, S.I ; Ferreira, D</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c448t-900131eae129266332be894833e2b964e6fb462bf6c03a7ae2917304b1b12fec3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Animals</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - isolation & purification</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>antibacterial properties</topic><topic>antifungal properties</topic><topic>antimalarials</topic><topic>Antimalarials - chemistry</topic><topic>Antimalarials - isolation & purification</topic><topic>Antimalarials - pharmacology</topic><topic>antioxidant activity</topic><topic>Antioxidants - chemistry</topic><topic>Antioxidants - isolation & purification</topic><topic>Antioxidants - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Chemical Fractionation</topic><topic>ellagic acid</topic><topic>ellagitannin</topic><topic>gallagic acid</topic><topic>General pharmacology</topic><topic>HL-60 Cells</topic><topic>Humans</topic><topic>Hydrolyzable Tannins - chemistry</topic><topic>Hydrolyzable Tannins - isolation & purification</topic><topic>Hydrolyzable Tannins - pharmacology</topic><topic>Hydroxybenzoates - chemistry</topic><topic>Hydroxybenzoates - isolation & purification</topic><topic>Hydroxybenzoates - pharmacology</topic><topic>Lythraceae</topic><topic>Medical sciences</topic><topic>medicinal plants</topic><topic>Microbial Sensitivity Tests</topic><topic>Original Paper</topic><topic>Pharmacognosy. Homeopathy. Health food</topic><topic>Pharmacology. Drug treatments</topic><topic>phenolic acids</topic><topic>phytochemicals</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - isolation & purification</topic><topic>Plasmodium falciparum</topic><topic>Plasmodium falciparum - drug effects</topic><topic>Punica granatum</topic><topic>Punicaceae - chemistry</topic><topic>punicalagin</topic><topic>punicalin</topic><topic>reactive oxygen species</topic><topic>Reactive Oxygen Species - metabolism</topic><topic>tannins</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Reddy, M.K</creatorcontrib><creatorcontrib>Gupta, S.K</creatorcontrib><creatorcontrib>Jacob, M.R</creatorcontrib><creatorcontrib>Khan, S.I</creatorcontrib><creatorcontrib>Ferreira, D</creatorcontrib><collection>AGRIS</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Planta medica</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Reddy, M.K</au><au>Gupta, S.K</au><au>Jacob, M.R</au><au>Khan, S.I</au><au>Ferreira, D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L</atitle><jtitle>Planta medica</jtitle><addtitle>Planta Med</addtitle><date>2007-05-01</date><risdate>2007</risdate><volume>73</volume><issue>5</issue><spage>461</spage><epage>467</epage><pages>461-467</pages><issn>0032-0943</issn><eissn>1439-0221</eissn><coden>PLMEAA</coden><abstract>Abstract
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), XAD-EtOAc, XAD-H
2
O, XAD-PJ and XAD-BuOH, exhibited IC
50
values against reactive oxygen species (ROS) generation at 0.8 - 19 μg/mL. Compounds 1 - 4 showed IC
50
values of 1.1, 3.2, 2.3 and 1.4 μM, respectively, against ROS generation and no toxicity up to 31.25 μg/mL against HL-60 cells. Gallagic acid (2) and punicalagins (4) exhibited antiplasmodial activity against PLASMODIUM FALCIPARUM D6 and W2 clones with IC
50
values of 10.9, 10.6, 7.5 and 8.8 μM, respectively. Fractions XAD-EtOAc, XAD-BuOH, XAD-H
2
O 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.</abstract><cop>Stuttgart</cop><cop>New York, NY</cop><pub>Thieme</pub><pmid>17566148</pmid><doi>10.1055/s-2007-967167</doi><tpages>7</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Planta medica, 2007-05, Vol.73 (5), p.461-467 |
| issn | 0032-0943 1439-0221 |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_2007_967167 |
| source | MEDLINE; Thieme Connect Journals |
| subjects | Animals Anti-Infective Agents - chemistry Anti-Infective Agents - isolation & purification Anti-Infective Agents - pharmacology antibacterial properties antifungal properties antimalarials Antimalarials - chemistry Antimalarials - isolation & purification Antimalarials - pharmacology antioxidant activity Antioxidants - chemistry Antioxidants - isolation & purification Antioxidants - pharmacology Biological and medical sciences Chemical Fractionation ellagic acid ellagitannin gallagic acid General pharmacology HL-60 Cells Humans Hydrolyzable Tannins - chemistry Hydrolyzable Tannins - isolation & purification Hydrolyzable Tannins - pharmacology Hydroxybenzoates - chemistry Hydroxybenzoates - isolation & purification Hydroxybenzoates - pharmacology Lythraceae Medical sciences medicinal plants Microbial Sensitivity Tests Original Paper Pharmacognosy. Homeopathy. Health food Pharmacology. Drug treatments phenolic acids phytochemicals Plant Extracts - chemistry Plant Extracts - isolation & purification Plasmodium falciparum Plasmodium falciparum - drug effects Punica granatum Punicaceae - chemistry punicalagin punicalin reactive oxygen species Reactive Oxygen Species - metabolism tannins |
| title | Antioxidant, antimalarial and antimicrobial activities of tannin-rich fractions, ellagitannins and phenolic acids from Punica granatum L |
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