Permeability studies of alkylamides and caffeic acid conjugates from echinacea using a Caco‐2 cell monolayer model
Summary Background: Echinacea is composed of three major groups of compounds that are thought to be responsible for stimulation of the immune system – the caffeic acid conjugates, alkylamides and polysaccharides. This study has focussed on the former two classes, as these are the constituents found...
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| Veröffentlicht in: | Journal of clinical pharmacy and therapeutics 2004-02, Vol.29 (1), p.7-13 |
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| container_title | Journal of clinical pharmacy and therapeutics |
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| creator | Matthias, A. Blanchfield, J. T. Penman, K. G. Toth, I. Lang, C.‐S. Voss, J. J. Lehmann, R. P. |
| description | Summary
Background: Echinacea is composed of three major groups of compounds that are thought to be responsible for stimulation of the immune system – the caffeic acid conjugates, alkylamides and polysaccharides. This study has focussed on the former two classes, as these are the constituents found in ethanolic liquid extracts.
Objective: To investigate the absorption of these two groups of compounds using Caco‐2 monolayers, which are a model of the intestinal epithelial barrier.
Results: The caffeic acid conjugates (caftaric acid, echinacoside and cichoric acid) permeated poorly through the Caco‐2 monolayers although one potential metabolite, cinnamic acid, diffused readily with an apparent permeability (Papp) of 1 × 10−4 cm/s. Alkylamides were found to diffuse through Caco‐2 monolayers with Papp ranging from 3 × 10−6 to 3 × 10−4 cm/s. This diversity in Papp for the different alkylamides correlates to structural variations, with saturation and N‐terminal methylation contributing to decreases in Papp. The transport of the alkylamides is not affected by the presence of other constituents and the results for synthetic alkylamides were in line with those for the alkylamides in the echinacea preparation.
Conclusion: Alkylamides but not caffeic acid conjugates are likely to cross the intestinal barrier. |
| doi_str_mv | 10.1046/j.1365-2710.2003.00530.x |
| format | Article |
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Background: Echinacea is composed of three major groups of compounds that are thought to be responsible for stimulation of the immune system – the caffeic acid conjugates, alkylamides and polysaccharides. This study has focussed on the former two classes, as these are the constituents found in ethanolic liquid extracts.
Objective: To investigate the absorption of these two groups of compounds using Caco‐2 monolayers, which are a model of the intestinal epithelial barrier.
Results: The caffeic acid conjugates (caftaric acid, echinacoside and cichoric acid) permeated poorly through the Caco‐2 monolayers although one potential metabolite, cinnamic acid, diffused readily with an apparent permeability (Papp) of 1 × 10−4 cm/s. Alkylamides were found to diffuse through Caco‐2 monolayers with Papp ranging from 3 × 10−6 to 3 × 10−4 cm/s. This diversity in Papp for the different alkylamides correlates to structural variations, with saturation and N‐terminal methylation contributing to decreases in Papp. The transport of the alkylamides is not affected by the presence of other constituents and the results for synthetic alkylamides were in line with those for the alkylamides in the echinacea preparation.
Conclusion: Alkylamides but not caffeic acid conjugates are likely to cross the intestinal barrier.</description><identifier>ISSN: 0269-4727</identifier><identifier>EISSN: 1365-2710</identifier><identifier>DOI: 10.1046/j.1365-2710.2003.00530.x</identifier><identifier>PMID: 14748892</identifier><identifier>CODEN: JCPTED</identifier><language>eng</language><publisher>Oxford, UK: Blackwell Science Ltd</publisher><subject>alkylamides ; Amides - chemistry ; Amides - pharmacokinetics ; bioavailability ; Biological Transport ; Caco-2 Cells ; Caco‐2 monolayers ; caffeic acid conjugates ; Caffeic Acids - chemistry ; Caffeic Acids - pharmacokinetics ; Cell Membrane Permeability ; echinacea ; Echinacea - chemistry ; Humans ; Plant Extracts - pharmacokinetics</subject><ispartof>Journal of clinical pharmacy and therapeutics, 2004-02, Vol.29 (1), p.7-13</ispartof><rights>Copyright Blackwell Scientific Publications Ltd. Feb 2004</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1046%2Fj.1365-2710.2003.00530.x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1046%2Fj.1365-2710.2003.00530.x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/14748892$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Matthias, A.</creatorcontrib><creatorcontrib>Blanchfield, J. T.</creatorcontrib><creatorcontrib>Penman, K. G.</creatorcontrib><creatorcontrib>Toth, I.</creatorcontrib><creatorcontrib>Lang, C.‐S.</creatorcontrib><creatorcontrib>Voss, J. J.</creatorcontrib><creatorcontrib>Lehmann, R. P.</creatorcontrib><title>Permeability studies of alkylamides and caffeic acid conjugates from echinacea using a Caco‐2 cell monolayer model</title><title>Journal of clinical pharmacy and therapeutics</title><addtitle>J Clin Pharm Ther</addtitle><description>Summary
Background: Echinacea is composed of three major groups of compounds that are thought to be responsible for stimulation of the immune system – the caffeic acid conjugates, alkylamides and polysaccharides. This study has focussed on the former two classes, as these are the constituents found in ethanolic liquid extracts.
Objective: To investigate the absorption of these two groups of compounds using Caco‐2 monolayers, which are a model of the intestinal epithelial barrier.
Results: The caffeic acid conjugates (caftaric acid, echinacoside and cichoric acid) permeated poorly through the Caco‐2 monolayers although one potential metabolite, cinnamic acid, diffused readily with an apparent permeability (Papp) of 1 × 10−4 cm/s. Alkylamides were found to diffuse through Caco‐2 monolayers with Papp ranging from 3 × 10−6 to 3 × 10−4 cm/s. This diversity in Papp for the different alkylamides correlates to structural variations, with saturation and N‐terminal methylation contributing to decreases in Papp. The transport of the alkylamides is not affected by the presence of other constituents and the results for synthetic alkylamides were in line with those for the alkylamides in the echinacea preparation.
Conclusion: Alkylamides but not caffeic acid conjugates are likely to cross the intestinal barrier.</description><subject>alkylamides</subject><subject>Amides - chemistry</subject><subject>Amides - pharmacokinetics</subject><subject>bioavailability</subject><subject>Biological Transport</subject><subject>Caco-2 Cells</subject><subject>Caco‐2 monolayers</subject><subject>caffeic acid conjugates</subject><subject>Caffeic Acids - chemistry</subject><subject>Caffeic Acids - pharmacokinetics</subject><subject>Cell Membrane Permeability</subject><subject>echinacea</subject><subject>Echinacea - chemistry</subject><subject>Humans</subject><subject>Plant Extracts - pharmacokinetics</subject><issn>0269-4727</issn><issn>1365-2710</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpdkc1u1TAQhS0EopfCKyCrC3a5nfgnzl10ga7KT1WJLsramiST4uDElzhRm10foc_Ik-DQAhIrz_h8mjn2YYznsM1BFafdNpeFzoRJFwJAbgG0hO3dM7b5KzxnGxDFLlNGmCP2KsYOAAoj5Et2lCujynInNmy6orEnrJx308LjNDeOIg8tR_998di7JrU4NLzGtiVXc6xdasLQzTc4Ja0dQ8-p_uYGrAn5HN1ww5HvsQ4_7x8Er8l73ocheFxoTFVD_jV70aKP9ObpPGZfP5xf7z9ll18-ft6_v8wOIr0qa7XRpVKpzFtjiHRpDFAlK424I5mrqlGNKBBAkdTVDiRCK7QAbCqsSiOP2bvHuYcx_JgpTrZ3cTWEA4U52hJyCVKrBJ78B3ZhHofkzabtOhnIiwS9fYLmqqfGHkbX47jYP5-ZgLNH4NZ5Wv7pYNfQbGfXbOyazTpV2t-h2Tt7sb-6TpX8BexXixg</recordid><startdate>200402</startdate><enddate>200402</enddate><creator>Matthias, A.</creator><creator>Blanchfield, J. T.</creator><creator>Penman, K. G.</creator><creator>Toth, I.</creator><creator>Lang, C.‐S.</creator><creator>Voss, J. J.</creator><creator>Lehmann, R. P.</creator><general>Blackwell Science Ltd</general><general>Hindawi Limited</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7T5</scope><scope>7TM</scope><scope>7TO</scope><scope>H94</scope><scope>K9.</scope><scope>M7N</scope><scope>7X8</scope></search><sort><creationdate>200402</creationdate><title>Permeability studies of alkylamides and caffeic acid conjugates from echinacea using a Caco‐2 cell monolayer model</title><author>Matthias, A. ; Blanchfield, J. T. ; Penman, K. G. ; Toth, I. ; Lang, C.‐S. ; Voss, J. J. ; Lehmann, R. P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p2200-f5758442001f77ee58770eb3b5aa9e314bd4d26a004e35b903a0f2520adbab873</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>alkylamides</topic><topic>Amides - chemistry</topic><topic>Amides - pharmacokinetics</topic><topic>bioavailability</topic><topic>Biological Transport</topic><topic>Caco-2 Cells</topic><topic>Caco‐2 monolayers</topic><topic>caffeic acid conjugates</topic><topic>Caffeic Acids - chemistry</topic><topic>Caffeic Acids - pharmacokinetics</topic><topic>Cell Membrane Permeability</topic><topic>echinacea</topic><topic>Echinacea - chemistry</topic><topic>Humans</topic><topic>Plant Extracts - pharmacokinetics</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matthias, A.</creatorcontrib><creatorcontrib>Blanchfield, J. T.</creatorcontrib><creatorcontrib>Penman, K. G.</creatorcontrib><creatorcontrib>Toth, I.</creatorcontrib><creatorcontrib>Lang, C.‐S.</creatorcontrib><creatorcontrib>Voss, J. J.</creatorcontrib><creatorcontrib>Lehmann, R. P.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>Immunology Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Oncogenes and Growth Factors Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of clinical pharmacy and therapeutics</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matthias, A.</au><au>Blanchfield, J. T.</au><au>Penman, K. G.</au><au>Toth, I.</au><au>Lang, C.‐S.</au><au>Voss, J. J.</au><au>Lehmann, R. P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Permeability studies of alkylamides and caffeic acid conjugates from echinacea using a Caco‐2 cell monolayer model</atitle><jtitle>Journal of clinical pharmacy and therapeutics</jtitle><addtitle>J Clin Pharm Ther</addtitle><date>2004-02</date><risdate>2004</risdate><volume>29</volume><issue>1</issue><spage>7</spage><epage>13</epage><pages>7-13</pages><issn>0269-4727</issn><eissn>1365-2710</eissn><coden>JCPTED</coden><abstract>Summary
Background: Echinacea is composed of three major groups of compounds that are thought to be responsible for stimulation of the immune system – the caffeic acid conjugates, alkylamides and polysaccharides. This study has focussed on the former two classes, as these are the constituents found in ethanolic liquid extracts.
Objective: To investigate the absorption of these two groups of compounds using Caco‐2 monolayers, which are a model of the intestinal epithelial barrier.
Results: The caffeic acid conjugates (caftaric acid, echinacoside and cichoric acid) permeated poorly through the Caco‐2 monolayers although one potential metabolite, cinnamic acid, diffused readily with an apparent permeability (Papp) of 1 × 10−4 cm/s. Alkylamides were found to diffuse through Caco‐2 monolayers with Papp ranging from 3 × 10−6 to 3 × 10−4 cm/s. This diversity in Papp for the different alkylamides correlates to structural variations, with saturation and N‐terminal methylation contributing to decreases in Papp. The transport of the alkylamides is not affected by the presence of other constituents and the results for synthetic alkylamides were in line with those for the alkylamides in the echinacea preparation.
Conclusion: Alkylamides but not caffeic acid conjugates are likely to cross the intestinal barrier.</abstract><cop>Oxford, UK</cop><pub>Blackwell Science Ltd</pub><pmid>14748892</pmid><doi>10.1046/j.1365-2710.2003.00530.x</doi><tpages>7</tpages></addata></record> |
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| ispartof | Journal of clinical pharmacy and therapeutics, 2004-02, Vol.29 (1), p.7-13 |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | alkylamides Amides - chemistry Amides - pharmacokinetics bioavailability Biological Transport Caco-2 Cells Caco‐2 monolayers caffeic acid conjugates Caffeic Acids - chemistry Caffeic Acids - pharmacokinetics Cell Membrane Permeability echinacea Echinacea - chemistry Humans Plant Extracts - pharmacokinetics |
| title | Permeability studies of alkylamides and caffeic acid conjugates from echinacea using a Caco‐2 cell monolayer model |
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