Synthesis of 1‑O‑Methylchlorogenic Acid: Reassignment of Structure for MCGA3 Isolated from Bamboo (Phyllostachys edulis) Leaves
The first synthesis of 1-O-methylchlorogenic acid is described. The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involves C-1 alkylation of the known (−)-4,5-cyclohexylidenequinic acid lact...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2014-02, Vol.62 (8), p.1860-1865 |
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| container_end_page | 1865 |
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| container_issue | 8 |
| container_start_page | 1860 |
| container_title | Journal of agricultural and food chemistry |
| container_volume | 62 |
| creator | Zeller, Wayne E |
| description | The first synthesis of 1-O-methylchlorogenic acid is described. The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involves C-1 alkylation of the known (−)-4,5-cyclohexylidenequinic acid lactone followed by methoxide opening to the hydroxyl ester. Acylation of the C-5 hydroxyl group followed by sequential removal of protecting groups afforded 1-O-methylchlorogenic acid. The NMR spectroscopic characteristics of this compound do not coincide with those reported for the original isolation from bamboo (Phyllostachys edulis) leaves of the compound designated MCGA3. Comparison of the published spectroscopic data reported for MCGA3, with both reported literature values and spectroscopic data obtained from an authentic sample, leads to the conclusion that the compound isolated from bamboo (Phyllostachys edulis) leaves is instead methyl chlorogenate. |
| doi_str_mv | 10.1021/jf4042112 |
| format | Article |
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The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involves C-1 alkylation of the known (−)-4,5-cyclohexylidenequinic acid lactone followed by methoxide opening to the hydroxyl ester. Acylation of the C-5 hydroxyl group followed by sequential removal of protecting groups afforded 1-O-methylchlorogenic acid. The NMR spectroscopic characteristics of this compound do not coincide with those reported for the original isolation from bamboo (Phyllostachys edulis) leaves of the compound designated MCGA3. Comparison of the published spectroscopic data reported for MCGA3, with both reported literature values and spectroscopic data obtained from an authentic sample, leads to the conclusion that the compound isolated from bamboo (Phyllostachys edulis) leaves is instead methyl chlorogenate.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf4042112</identifier><identifier>PMID: 24460043</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Chlorogenic Acid - analogs & derivatives ; Chlorogenic Acid - chemistry ; Chlorogenic Acid - metabolism ; Molecular Structure ; Plant Extracts - chemistry ; Plant Extracts - metabolism ; Plant Leaves - chemistry ; Plant Leaves - metabolism ; Poaceae - chemistry ; Poaceae - metabolism</subject><ispartof>Journal of agricultural and food chemistry, 2014-02, Vol.62 (8), p.1860-1865</ispartof><rights>Copyright © 2014 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a315t-57b0fde0ab453ad48bd6767443cf9b78602122a5d322a3b7459c4b886c2829673</citedby><cites>FETCH-LOGICAL-a315t-57b0fde0ab453ad48bd6767443cf9b78602122a5d322a3b7459c4b886c2829673</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf4042112$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf4042112$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/24460043$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zeller, Wayne E</creatorcontrib><title>Synthesis of 1‑O‑Methylchlorogenic Acid: Reassignment of Structure for MCGA3 Isolated from Bamboo (Phyllostachys edulis) Leaves</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The first synthesis of 1-O-methylchlorogenic acid is described. The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involves C-1 alkylation of the known (−)-4,5-cyclohexylidenequinic acid lactone followed by methoxide opening to the hydroxyl ester. Acylation of the C-5 hydroxyl group followed by sequential removal of protecting groups afforded 1-O-methylchlorogenic acid. The NMR spectroscopic characteristics of this compound do not coincide with those reported for the original isolation from bamboo (Phyllostachys edulis) leaves of the compound designated MCGA3. Comparison of the published spectroscopic data reported for MCGA3, with both reported literature values and spectroscopic data obtained from an authentic sample, leads to the conclusion that the compound isolated from bamboo (Phyllostachys edulis) leaves is instead methyl chlorogenate.</description><subject>Chlorogenic Acid - analogs & derivatives</subject><subject>Chlorogenic Acid - chemistry</subject><subject>Chlorogenic Acid - metabolism</subject><subject>Molecular Structure</subject><subject>Plant Extracts - chemistry</subject><subject>Plant Extracts - metabolism</subject><subject>Plant Leaves - chemistry</subject><subject>Plant Leaves - metabolism</subject><subject>Poaceae - chemistry</subject><subject>Poaceae - metabolism</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkM9OGzEQhy3UqoS0B16g8qUSOWyxvfb-6S2NIERKBCpwXnm9s2Sj3XXq8SLlhtQn6CvyJDgKcOIwM4f59JN-HyGnnP3kTPDzTS2ZFJyLIzLiSrBIcZ59IiMWnlGmEn5MThA3jLFMpewLORZSJozJeET-3e56vwZskNqa8uen_9dhVuDXu9asW-vsA_SNoVPTVL_oH9CIzUPfQe_3_K13g_GDA1pbR1ez-TSmC7St9lDR2tmO_tZdaS09uwl5rUWvzXqHFKqhbXBCl6AfAb-Sz7VuEb693jG5v7y4m11Fy-v5YjZdRjrmykcqLVldAdOlVLGuZFZWSZqkUsamzss0S0JbIbSq4rDjMpUqN7LMssSITORJGo_J2SF36-zfAdAXXYMG2lb3YAcsuGIiz1MexIzJ5IAaZxEd1MXWNZ12u4KzYu-8eHce2O-vsUPZQfVOvkkOwI8DoA0WGzu4PrT8IOgF5aOI8g</recordid><startdate>20140226</startdate><enddate>20140226</enddate><creator>Zeller, Wayne E</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20140226</creationdate><title>Synthesis of 1‑O‑Methylchlorogenic Acid: Reassignment of Structure for MCGA3 Isolated from Bamboo (Phyllostachys edulis) Leaves</title><author>Zeller, Wayne E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a315t-57b0fde0ab453ad48bd6767443cf9b78602122a5d322a3b7459c4b886c2829673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Chlorogenic Acid - analogs & derivatives</topic><topic>Chlorogenic Acid - chemistry</topic><topic>Chlorogenic Acid - metabolism</topic><topic>Molecular Structure</topic><topic>Plant Extracts - chemistry</topic><topic>Plant Extracts - metabolism</topic><topic>Plant Leaves - chemistry</topic><topic>Plant Leaves - metabolism</topic><topic>Poaceae - chemistry</topic><topic>Poaceae - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zeller, Wayne E</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zeller, Wayne E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 1‑O‑Methylchlorogenic Acid: Reassignment of Structure for MCGA3 Isolated from Bamboo (Phyllostachys edulis) Leaves</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2014-02-26</date><risdate>2014</risdate><volume>62</volume><issue>8</issue><spage>1860</spage><epage>1865</epage><pages>1860-1865</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><abstract>The first synthesis of 1-O-methylchlorogenic acid is described. The short and efficient synthesis of this compound provides laboratory-scale quantities of the material to investigate its biological properties. The synthesis involves C-1 alkylation of the known (−)-4,5-cyclohexylidenequinic acid lactone followed by methoxide opening to the hydroxyl ester. Acylation of the C-5 hydroxyl group followed by sequential removal of protecting groups afforded 1-O-methylchlorogenic acid. The NMR spectroscopic characteristics of this compound do not coincide with those reported for the original isolation from bamboo (Phyllostachys edulis) leaves of the compound designated MCGA3. Comparison of the published spectroscopic data reported for MCGA3, with both reported literature values and spectroscopic data obtained from an authentic sample, leads to the conclusion that the compound isolated from bamboo (Phyllostachys edulis) leaves is instead methyl chlorogenate.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>24460043</pmid><doi>10.1021/jf4042112</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2014-02, Vol.62 (8), p.1860-1865 |
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| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Chlorogenic Acid - analogs & derivatives Chlorogenic Acid - chemistry Chlorogenic Acid - metabolism Molecular Structure Plant Extracts - chemistry Plant Extracts - metabolism Plant Leaves - chemistry Plant Leaves - metabolism Poaceae - chemistry Poaceae - metabolism |
| title | Synthesis of 1‑O‑Methylchlorogenic Acid: Reassignment of Structure for MCGA3 Isolated from Bamboo (Phyllostachys edulis) Leaves |
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