{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,30]],"date-time":"2026-05-30T02:14:10Z","timestamp":1780107250204,"version":"3.54.0"},"reference-count":39,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2017,1,30]],"date-time":"2017-01-30T00:00:00Z","timestamp":1485734400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2017,2]]},"abstract":"<jats:p><jats:italic>Mercurialis tomentosa<\/jats:italic> L. has been used in Spanish ethnomedicine. In the present study the first phytochemical characterisation of a lipid fraction from <jats:italic>M<\/jats:italic>.\u00a0<jats:italic>tomentosa<\/jats:italic> was performed. The <jats:styled-content style=\"fixed-case\">CHC<\/jats:styled-content>l<jats:sub>3<\/jats:sub> extraction of aerial parts from <jats:italic>M<\/jats:italic>.\u00a0<jats:italic>tomentosa<\/jats:italic> and <jats:styled-content style=\"fixed-case\">GC<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content> investigations revealed the occurrence of cuticular lipid and wax constituents, like long chain <jats:italic>n<\/jats:italic>\u2010alcohols and <jats:italic>n<\/jats:italic>\u2010aldehydes (C<jats:sub>22<\/jats:sub>\u00a0\u2013\u00a0C<jats:sub>30<\/jats:sub>), besides several aromatic constituents, <jats:italic>i.e<\/jats:italic>., phenylpropanoids and <jats:italic>n<\/jats:italic>\u2010alkylresorcinols. The latter were further purified by <jats:styled-content style=\"fixed-case\">CC<\/jats:styled-content> and analysed by <jats:styled-content style=\"fixed-case\">LC<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content><jats:sup><jats:italic>n<\/jats:italic><\/jats:sup>. In contrast to other <jats:italic>Mercurialis<\/jats:italic> species, <jats:italic>i.e<\/jats:italic>., <jats:italic>M<\/jats:italic>.\u00a0<jats:italic>annua<\/jats:italic>,<jats:italic> M<\/jats:italic>.\u00a0<jats:italic>perennis<\/jats:italic>, which exclusively contain 5\u2010<jats:italic>n<\/jats:italic>\u2010alkylresorcinols (<jats:bold>1a<\/jats:bold>\u00a0\u2013\u00a0<jats:bold>j<\/jats:bold>, C<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub>), mainly 5\u2010<jats:italic>n<\/jats:italic>\u2010alkyl\u20102\u2010methylresorcinols (<jats:bold>2a<\/jats:bold>\u00a0\u2013\u00a0<jats:bold>j<\/jats:bold>, C<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub>*) with side chain lengths of C<jats:sub>15<\/jats:sub>\u00a0\u2013\u00a0C<jats:sub>25<\/jats:sub> were found in <jats:italic>M<\/jats:italic>.\u00a0<jats:italic>tomentosa<\/jats:italic>, in addition to <jats:bold>1a<\/jats:bold>\u00a0\u2013\u00a0<jats:bold>j<\/jats:bold>. Thus, the latter compounds may be utilised for analytical characterisation and authentication of <jats:italic>M<\/jats:italic>.\u00a0<jats:italic>tomentosa<\/jats:italic> based on fingerprinting methods. For structure elucidation a novel facile total synthesis of one representative 5\u2010<jats:italic>n<\/jats:italic>\u2010alkyl\u20102\u2010methylresorcinol homologue (<jats:bold>2d<\/jats:bold>, C<jats:sub>19<\/jats:sub>*) was developed, starting with a <jats:italic>Grignard<\/jats:italic> reaction from a substituted benzoic acid chloride (<jats:bold>19<\/jats:bold>). The compound obtained by synthesis was identical to the natural product <jats:bold>2d<\/jats:bold> in terms of its chromatographic and spectroscopic features. Futhermore, <jats:bold>2d<\/jats:bold> exhibited satisfactory <jats:styled-content style=\"fixed-case\">DPPH<\/jats:styled-content> free radical scavenging activity (<jats:italic><jats:styled-content style=\"fixed-case\">IC<\/jats:styled-content><\/jats:italic><jats:sub>50<\/jats:sub>\u00a0=\u00a037.8\u00a0\u03bc<jats:sc>m<\/jats:sc>) when compared to trolox (<jats:italic><jats:styled-content style=\"fixed-case\">IC<\/jats:styled-content><\/jats:italic><jats:sub>50<\/jats:sub>\u00a0=\u00a021.0\u00a0\u03bc<jats:sc>m<\/jats:sc>), corroborating the antioxidant features of these amphipathic molecules.<\/jats:p>","DOI":"10.1002\/cbdv.201600255","type":"journal-article","created":{"date-parts":[[2016,9,1]],"date-time":"2016-09-01T23:12:56Z","timestamp":1472771576000},"source":"Crossref","is-referenced-by-count":10,"title":["Comprehensive Characterisation of <i>n<\/i>\u2010Alkylresorcinols and Other Lipid Constituents of <i>Mercurialis tomentosa<\/i> L. from Alicante, Spain"],"prefix":"10.1002","volume":"14","author":[{"given":"Peter","family":"Lorenz","sequence":"first","affiliation":[{"name":"Section\u00a0Phytochemical Research Department of Analytical Development &amp; Research WALA Heilmittel GmbH Dorfstrasse 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Miriam","family":"Heinrich","sequence":"additional","affiliation":[{"name":"Section\u00a0Phytochemical Research Department of Analytical Development &amp; Research WALA Heilmittel GmbH Dorfstrasse 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00fcrgen","family":"Conrad","sequence":"additional","affiliation":[{"name":"Institute of Chemistry, Bioorganic Chemistry (130b) University of Hohenheim Garbenstra\u00dfe 30 DE\u201070599 Stuttgart"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Annerose","family":"Heller","sequence":"additional","affiliation":[{"name":"Institute of Botany (210) University of Hohenheim Garbenstra\u00dfe 30 DE\u201070599 Stuttgart"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Florian C.","family":"Stintzing","sequence":"additional","affiliation":[{"name":"Section\u00a0Phytochemical Research Department of Analytical Development &amp; Research WALA Heilmittel GmbH Dorfstrasse 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Dietmar R.","family":"Kammerer","sequence":"additional","affiliation":[{"name":"Section\u00a0Phytochemical Research Department of Analytical Development &amp; Research WALA Heilmittel GmbH Dorfstrasse 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2017,1,30]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbalip.2011.06.009"},{"key":"e_1_2_6_3_1","first-page":"1","volume-title":"The Lipid Handbook","author":"Scrimgeour C. 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