Volatile Organic Sulfur-Containing Constituents in Poncirus trifoliata (L.) Raf. (Rutaceae)
During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L.) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alk...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 2007-05, Vol.55 (11), p.4511-4517 |
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| container_title | Journal of agricultural and food chemistry |
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| creator | Starkenmann, Christian Niclass, Yvan Escher, Sina |
| description | During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L.) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alkanoates of 3-methyl-3-sulfanylbutan-1-ol and 3-sulfanylhexan-1-ol, respectively, and thus are members of a family of natural molecules having in common a 1,3-positioned O,S moiety. The alkanoate residues comprise all even-numbered saturated fatty acids from C2 (acetate) to C18 (octadecanoate). Among the 20 sulfur-containing compounds identified, 14 are described for the first time as naturally occurring in a botanical species. Several cysteine-S-conjugates were synthesized as hypothetical precursors of the new volatile sulfur-containing constituents, where after S-(3-hydroxy-1,1-dimethylpropyl)-l-cysteine, S-[3-(acetyloxy)-1,1-dimethylpropyl]-l-cysteine, and S-[1-(2-hydroxyethyl)butyl]-l-cysteine were identified in the fruit peel. No cysteine-S-conjugates were detected in the fruit juice. Keywords: Poncirus trifoliata (L.) Raf.; 3-methyl-3-sulfanylbutan-1-ol; 3-methyl-3-sulfanylhexan-1-ol; 3-methyl-3-sulfanylbutyl alkanoates; 3-sulfanylhexyl alkanoates; cysteine-S-conjugates; natural occurrence; fragrance and flavor chemical |
| doi_str_mv | 10.1021/jf063453h |
| format | Article |
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Raf. (Rutaceae)</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Starkenmann, Christian ; Niclass, Yvan ; Escher, Sina</creator><creatorcontrib>Starkenmann, Christian ; Niclass, Yvan ; Escher, Sina</creatorcontrib><description>During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L.) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alkanoates of 3-methyl-3-sulfanylbutan-1-ol and 3-sulfanylhexan-1-ol, respectively, and thus are members of a family of natural molecules having in common a 1,3-positioned O,S moiety. The alkanoate residues comprise all even-numbered saturated fatty acids from C2 (acetate) to C18 (octadecanoate). Among the 20 sulfur-containing compounds identified, 14 are described for the first time as naturally occurring in a botanical species. Several cysteine-S-conjugates were synthesized as hypothetical precursors of the new volatile sulfur-containing constituents, where after S-(3-hydroxy-1,1-dimethylpropyl)-l-cysteine, S-[3-(acetyloxy)-1,1-dimethylpropyl]-l-cysteine, and S-[1-(2-hydroxyethyl)butyl]-l-cysteine were identified in the fruit peel. No cysteine-S-conjugates were detected in the fruit juice. Keywords: Poncirus trifoliata (L.) Raf.; 3-methyl-3-sulfanylbutan-1-ol; 3-methyl-3-sulfanylhexan-1-ol; 3-methyl-3-sulfanylbutyl alkanoates; 3-sulfanylhexyl alkanoates; cysteine-S-conjugates; natural occurrence; fragrance and flavor chemical</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf063453h</identifier><identifier>PMID: 17488024</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>acetates ; alkanoates ; Biological and medical sciences ; chemical composition ; Citrus ; cysteine ; flavor compounds ; flavorings ; food additives ; Food industries ; fruit juices ; fruits (food) ; Fundamental and applied biological sciences. Psychology ; Mass Spectrometry ; Nuclear Magnetic Resonance, Biomolecular ; octadecanoate ; odor compounds ; odors ; peels ; plant extracts ; Plant Extracts - chemistry ; Poncirus - chemistry ; Poncirus trifoliata ; Rutaceae ; saturated fatty acids ; sensory properties ; sulfur ; sulfur amino acids ; Sulfur Compounds - chemistry ; Sulfur Compounds - isolation & purification ; wild plants</subject><ispartof>Journal of agricultural and food chemistry, 2007-05, Vol.55 (11), p.4511-4517</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a436t-12108e69a3d50512d753e768156065f13cad0faf0c403b8e001a8c13a0ee14b13</citedby><cites>FETCH-LOGICAL-a436t-12108e69a3d50512d753e768156065f13cad0faf0c403b8e001a8c13a0ee14b13</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/jf063453h$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf063453h$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18807840$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17488024$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Starkenmann, Christian</creatorcontrib><creatorcontrib>Niclass, Yvan</creatorcontrib><creatorcontrib>Escher, Sina</creatorcontrib><title>Volatile Organic Sulfur-Containing Constituents in Poncirus trifoliata (L.) Raf. (Rutaceae)</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L.) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alkanoates of 3-methyl-3-sulfanylbutan-1-ol and 3-sulfanylhexan-1-ol, respectively, and thus are members of a family of natural molecules having in common a 1,3-positioned O,S moiety. The alkanoate residues comprise all even-numbered saturated fatty acids from C2 (acetate) to C18 (octadecanoate). Among the 20 sulfur-containing compounds identified, 14 are described for the first time as naturally occurring in a botanical species. Several cysteine-S-conjugates were synthesized as hypothetical precursors of the new volatile sulfur-containing constituents, where after S-(3-hydroxy-1,1-dimethylpropyl)-l-cysteine, S-[3-(acetyloxy)-1,1-dimethylpropyl]-l-cysteine, and S-[1-(2-hydroxyethyl)butyl]-l-cysteine were identified in the fruit peel. No cysteine-S-conjugates were detected in the fruit juice. Keywords: Poncirus trifoliata (L.) Raf.; 3-methyl-3-sulfanylbutan-1-ol; 3-methyl-3-sulfanylhexan-1-ol; 3-methyl-3-sulfanylbutyl alkanoates; 3-sulfanylhexyl alkanoates; cysteine-S-conjugates; natural occurrence; fragrance and flavor chemical</description><subject>acetates</subject><subject>alkanoates</subject><subject>Biological and medical sciences</subject><subject>chemical composition</subject><subject>Citrus</subject><subject>cysteine</subject><subject>flavor compounds</subject><subject>flavorings</subject><subject>food additives</subject><subject>Food industries</subject><subject>fruit juices</subject><subject>fruits (food)</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Mass Spectrometry</subject><subject>Nuclear Magnetic Resonance, Biomolecular</subject><subject>octadecanoate</subject><subject>odor compounds</subject><subject>odors</subject><subject>peels</subject><subject>plant extracts</subject><subject>Plant Extracts - chemistry</subject><subject>Poncirus - chemistry</subject><subject>Poncirus trifoliata</subject><subject>Rutaceae</subject><subject>saturated fatty acids</subject><subject>sensory properties</subject><subject>sulfur</subject><subject>sulfur amino acids</subject><subject>Sulfur Compounds - chemistry</subject><subject>Sulfur Compounds - isolation & purification</subject><subject>wild plants</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0cFqGzEQBmARWhI3zaEv0O6lJT6sO7NarZRjMUlaMCTETi45iLEsuXLXu4mkhfTtq2ITXwo9STAf_6BfjH1AmCBU-HXjoOG14D-P2AhFBaVAVG_YCPKwVKLBE_Yuxg0AKCHhmJ2grJWCqh6xx4e-peRbW9yENXXeFPOhdUMop32XyHe-Wxf5GpNPg-1SLHxX3Pad8WGIRQre9a2nRMX5bDIu7shNivO7IZGxZMfv2VtHbbRn-_OU3V9dLqbfy9nN9Y_pt1lJNW9SiRWCss0F8ZUAgdVKCm5lo1A00AiH3NAKHDkwNfClsgBIyiAnsBbrJfJT9mWX-xT658HGpLc-Gtu21Nl-iFrmVF5z_l9YQa1qECrD8Q6a0McYrNNPwW8p_NYI-m_l-rXybD_uQ4fl1q4Oct9xBp_3gKKh1gXK9cWDy0rmtdmVO-djsi-vcwq_dCO5FHpxO9dQqcXD9fxKT7P_tPOOek3rkDPv5xUgB5DyIld52Ewm6k0_hC5_wz-e8AcL56qs</recordid><startdate>20070530</startdate><enddate>20070530</enddate><creator>Starkenmann, Christian</creator><creator>Niclass, Yvan</creator><creator>Escher, Sina</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</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><scope>7QR</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20070530</creationdate><title>Volatile Organic Sulfur-Containing Constituents in Poncirus trifoliata (L.) Raf. (Rutaceae)</title><author>Starkenmann, Christian ; Niclass, Yvan ; Escher, Sina</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a436t-12108e69a3d50512d753e768156065f13cad0faf0c403b8e001a8c13a0ee14b13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>acetates</topic><topic>alkanoates</topic><topic>Biological and medical sciences</topic><topic>chemical composition</topic><topic>Citrus</topic><topic>cysteine</topic><topic>flavor compounds</topic><topic>flavorings</topic><topic>food additives</topic><topic>Food industries</topic><topic>fruit juices</topic><topic>fruits (food)</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Mass Spectrometry</topic><topic>Nuclear Magnetic Resonance, Biomolecular</topic><topic>octadecanoate</topic><topic>odor compounds</topic><topic>odors</topic><topic>peels</topic><topic>plant extracts</topic><topic>Plant Extracts - chemistry</topic><topic>Poncirus - chemistry</topic><topic>Poncirus trifoliata</topic><topic>Rutaceae</topic><topic>saturated fatty acids</topic><topic>sensory properties</topic><topic>sulfur</topic><topic>sulfur amino acids</topic><topic>Sulfur Compounds - chemistry</topic><topic>Sulfur Compounds - isolation & purification</topic><topic>wild plants</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Starkenmann, Christian</creatorcontrib><creatorcontrib>Niclass, Yvan</creatorcontrib><creatorcontrib>Escher, Sina</creatorcontrib><collection>AGRIS</collection><collection>Istex</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><collection>Chemoreception Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</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>Starkenmann, Christian</au><au>Niclass, Yvan</au><au>Escher, Sina</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Volatile Organic Sulfur-Containing Constituents in Poncirus trifoliata (L.) Raf. (Rutaceae)</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2007-05-30</date><risdate>2007</risdate><volume>55</volume><issue>11</issue><spage>4511</spage><epage>4517</epage><pages>4511-4517</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>During our screening of plant materials to find new natural fragrance and flavor ingredients, we discovered two series of 3-sulfanylalkyl alkanoates in a peel extract of fruits of wild-growing Poncirus trifoliata (L.) Raf. (Rutaceae), a species closely related to Citrus. The two series belong to alkanoates of 3-methyl-3-sulfanylbutan-1-ol and 3-sulfanylhexan-1-ol, respectively, and thus are members of a family of natural molecules having in common a 1,3-positioned O,S moiety. The alkanoate residues comprise all even-numbered saturated fatty acids from C2 (acetate) to C18 (octadecanoate). Among the 20 sulfur-containing compounds identified, 14 are described for the first time as naturally occurring in a botanical species. Several cysteine-S-conjugates were synthesized as hypothetical precursors of the new volatile sulfur-containing constituents, where after S-(3-hydroxy-1,1-dimethylpropyl)-l-cysteine, S-[3-(acetyloxy)-1,1-dimethylpropyl]-l-cysteine, and S-[1-(2-hydroxyethyl)butyl]-l-cysteine were identified in the fruit peel. No cysteine-S-conjugates were detected in the fruit juice. Keywords: Poncirus trifoliata (L.) Raf.; 3-methyl-3-sulfanylbutan-1-ol; 3-methyl-3-sulfanylhexan-1-ol; 3-methyl-3-sulfanylbutyl alkanoates; 3-sulfanylhexyl alkanoates; cysteine-S-conjugates; natural occurrence; fragrance and flavor chemical</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17488024</pmid><doi>10.1021/jf063453h</doi><tpages>7</tpages></addata></record> |
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| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2007-05, Vol.55 (11), p.4511-4517 |
| issn | 0021-8561 1520-5118 |
| language | eng |
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| subjects | acetates alkanoates Biological and medical sciences chemical composition Citrus cysteine flavor compounds flavorings food additives Food industries fruit juices fruits (food) Fundamental and applied biological sciences. Psychology Mass Spectrometry Nuclear Magnetic Resonance, Biomolecular octadecanoate odor compounds odors peels plant extracts Plant Extracts - chemistry Poncirus - chemistry Poncirus trifoliata Rutaceae saturated fatty acids sensory properties sulfur sulfur amino acids Sulfur Compounds - chemistry Sulfur Compounds - isolation & purification wild plants |
| title | Volatile Organic Sulfur-Containing Constituents in Poncirus trifoliata (L.) Raf. (Rutaceae) |
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