{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,17]],"date-time":"2026-01-17T05:05:29Z","timestamp":1768626329860,"version":"3.49.0"},"reference-count":46,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2017,7,17]],"date-time":"2017-07-17T00:00:00Z","timestamp":1500249600000},"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":[[2017,8]]},"abstract":"<jats:p>Seeds of <jats:italic>Hypericum perforatum<\/jats:italic> and <jats:italic>H. tetrapterum<\/jats:italic> were extracted with dichloromethane and methanol and investigated by chromatographic and mass spectrometric methods. Both species yielded a fatty oil fraction amounting to 30.5% and 18.0% of the seed weight, respectively. Linoleic acid (C18:2n\u20106) was shown to be the predominant fatty acid constituent. Moreover, xanthone derivatives, <jats:italic>i.e<\/jats:italic>. tetrahydroxyxanthones (<jats:styled-content style=\"fixed-case\">THX<\/jats:styled-content>), xanthone\u2010glycosides and xanthone\u2010sulfonates, were assigned in methanolic extracts. For structure elucidation, one representative xanthone, namely 1,3,6,7\u2010<jats:styled-content style=\"fixed-case\">THX<\/jats:styled-content>, was synthesized and analyzed <jats:italic>via <\/jats:italic><jats:styled-content style=\"fixed-case\">HPLC<\/jats:styled-content>\u2010<jats:styled-content style=\"fixed-case\">DAD<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content><jats:sup><jats:italic>n<\/jats:italic><\/jats:sup> and <jats:styled-content style=\"fixed-case\">GC<\/jats:styled-content>\/<jats:styled-content style=\"fixed-case\">MS<\/jats:styled-content>. Total <jats:styled-content style=\"fixed-case\">THX<\/jats:styled-content> contents were quantitated applying a validated <jats:styled-content style=\"fixed-case\">HPLC<\/jats:styled-content>\u2010<jats:styled-content style=\"fixed-case\">DAD<\/jats:styled-content> method, resulting in 1.25 g\/kg (<jats:italic>H. perforatum<\/jats:italic>) and 0.27 g\/kg (<jats:italic>H. tetrapterum<\/jats:italic>), respectively. Moreover, the free radical scavenging capacity of the methanol extracts was tested using the <jats:styled-content style=\"fixed-case\">DPPH<\/jats:styled-content> antioxidant assay. Both, <jats:italic>H. perforatum<\/jats:italic> (<jats:italic><jats:styled-content style=\"fixed-case\">IC<\/jats:styled-content><\/jats:italic><jats:sub>50<\/jats:sub> = 8.7 mg\/l) and 1,3,6,7\u2010<jats:styled-content style=\"fixed-case\">THX<\/jats:styled-content> (<jats:italic><jats:styled-content style=\"fixed-case\">IC<\/jats:styled-content><\/jats:italic><jats:sub>50<\/jats:sub> = 3.0 mg\/l), exhibited good <jats:styled-content style=\"fixed-case\">DPPH<\/jats:styled-content> free radical scavenging activity compared to <jats:italic>Trolox<\/jats:italic> (<jats:italic><jats:styled-content style=\"fixed-case\">IC<\/jats:styled-content><\/jats:italic><jats:sub>50<\/jats:sub> = 6.6 mg\/l).<\/jats:p>","DOI":"10.1002\/cbdv.201700100","type":"journal-article","created":{"date-parts":[[2017,5,29]],"date-time":"2017-05-29T12:22:39Z","timestamp":1496060559000},"source":"Crossref","is-referenced-by-count":14,"title":["Lipid and Phenolic Constituents from Seeds of <i>Hypericum perforatum<\/i> L. and <i>Hypericum tetrapterum <\/i><scp>Fr<\/scp>. and their Antioxidant Activity"],"prefix":"10.1002","volume":"14","author":[{"given":"Miriam","family":"Heinrich","sequence":"first","affiliation":[{"name":"WALA Heilmittel GmbH Department of Analytical Development &amp; Research Section Phytochemical Research Dorfstra\u00dfe 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"},{"name":"Department of Pharmaceutical Technology University of T\u00fcbingen Auf der Morgenstelle 8 DE\u201072076 T\u00fcbingen"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Peter","family":"Lorenz","sequence":"additional","affiliation":[{"name":"WALA Heilmittel GmbH Department of Analytical Development &amp; Research Section Phytochemical Research Dorfstra\u00dfe 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rolf","family":"Daniels","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Technology University of T\u00fcbingen Auf der Morgenstelle 8 DE\u201072076 T\u00fcbingen"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Florian C.","family":"Stintzing","sequence":"additional","affiliation":[{"name":"WALA Heilmittel GmbH Department of Analytical Development &amp; Research Section Phytochemical Research Dorfstra\u00dfe 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dietmar R.","family":"Kammerer","sequence":"additional","affiliation":[{"name":"WALA Heilmittel GmbH Department of Analytical Development &amp; Research Section Phytochemical Research Dorfstra\u00dfe 1 DE\u201073087 Bad Boll\/Eckw\u00e4lden"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2017,7,17]]},"reference":[{"key":"e_1_2_7_2_1","first-page":"1","article-title":"Taxonomy and chemotaxonomy of the genus Hypericum","volume":"5","author":"Crockett S. L.","year":"2011","journal-title":"Med. Aromat. Plant Sci. Biotechnol."},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1572-5995(05)80043-2"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/ptr.5050"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.euroneuro.2010.07.005"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1078\/0944-7113-00340"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1192\/bjp.186.2.99"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1211\/0022357011775910"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-979533"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(99)00214-7"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1046\/j.1365-2133.2000.03482.x"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-967198"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2006.05.062"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(98)00697-9"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2009.07.022"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf0527246"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/jsfa.4202"},{"key":"e_1_2_7_18_1","first-page":"737","article-title":"Phenolic acids and flavonoids in Hypericum perforatum L. hairy roots","volume":"4","author":"Tusevski O.","year":"2013","journal-title":"Int. J. Pharm. Bio. Sci."},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1155\/2013\/602752"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1007\/7081_2007_079"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/np50003a012"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1078\/0176-1617-00195"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1080\/14786410410001704796"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2008.10.016"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0168-9452(99)00178-8"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.2174\/092986705774370691"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2004.08.014"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.6b00251"},{"key":"e_1_2_7_29_1","first-page":"904","article-title":"Omega\u20103 content, antimicrobial and antioxidant activities of hexanic extract from seed and leaf of Hypericum scabrum from northwestern Iran","volume":"6","author":"Shafaghat A.","year":"2012","journal-title":"Afr. J. Microbiol. Res."},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.3989\/gya.1994.v45.i3.981"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf011440s"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9673(01)80947-X"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.6419"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-1565(199807\/08)9:4<171::AID-PCA396>3.0.CO;2-9"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(67)80058-9"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2005.10.017"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0031-9422(99)00190-9"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1155\/2013\/621459"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.dyepig.2006.05.040"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4NP00050A"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2003.07.024"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.niox.2003.09.005"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2009.03.056"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.201200424"},{"key":"e_1_2_7_45_1","unstructured":"International Conference on Harmonisation \u2018Validation of analytical procedures: text and methodology Q2(R1)\u2019 2005 http:\/\/www.ema.europa.eu\/docs\/en_GB\/document_library\/Scientific_guideline\/2009\/09\/WC500002662.pdf; Accessed February 21 2017."},{"key":"e_1_2_7_46_1","first-page":"803a","article-title":"Oxidative coupling: ortho\/para\u2010cyclisation of hydroxybenzophenones","volume":"16","author":"E Atkinson J.","year":"1967","journal-title":"Chem. Commun."},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1080\/10286020.2014.1003048"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbdv.201700100","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.201700100","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,5]],"date-time":"2023-10-05T20:20:54Z","timestamp":1696537254000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.201700100"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,7,17]]},"references-count":46,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2017,8]]}},"alternative-id":["10.1002\/cbdv.201700100"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.201700100","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,7,17]]},"article-number":"e1700100"}}