{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,6]],"date-time":"2026-07-06T20:14:31Z","timestamp":1783368871161,"version":"3.54.6"},"reference-count":21,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2026,6,24]],"date-time":"2026-06-24T00:00:00Z","timestamp":1782259200000},"content-version":"vor","delay-in-days":23,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,6,1]],"date-time":"2026-06-01T00:00:00Z","timestamp":1780272000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2026,6]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Two previously undescribed highly oxygenated monoterpenes, (1\n                    <jats:italic>R<\/jats:italic>\n                    ,2\n                    <jats:italic>S<\/jats:italic>\n                    ,5\n                    <jats:italic>R<\/jats:italic>\n                    )\u20103\u2010\n                    <jats:italic>p<\/jats:italic>\n                    \u2010menthen\u20101,2,5\u2010triol (1) and (1\n                    <jats:italic>R<\/jats:italic>\n                    ,5\n                    <jats:italic>S<\/jats:italic>\n                    )\u20102\u2010oxo\u20103\u2010\n                    <jats:italic>p<\/jats:italic>\n                    \u2010menthen\u20101,5\u2010diol (2), together with five known monoterpenes (\n                    <jats:bold>3\u20137<\/jats:bold>\n                    ), were isolated from the seeds of\n                    <jats:italic>Dysphania ambrosioides<\/jats:italic>\n                    . Their chemical structures were determined using various spectroscopic analyses (HRESIMS, and 1D and 2D NMR). The absolute configurations of compounds\n                    <jats:bold>1<\/jats:bold>\n                    and\n                    <jats:bold>2<\/jats:bold>\n                    were successfully established by both experimental and calculated ECD spectra using TD\u2010DFT methods. Among the isolates, compounds\n                    <jats:bold>3<\/jats:bold>\n                    and\n                    <jats:bold>6<\/jats:bold>\n                    exhibited significant inhibitory activity against NO production in LPS\u2010stimulated RAW264.7 cells, with IC\n                    <jats:sub>50<\/jats:sub>\n                    values of 14.5 and 17.4 \u00b5M, respectively. The remaining compounds displayed moderate inhibitory effects, with IC\n                    <jats:sub>50<\/jats:sub>\n                    values ranging from 42.1 to 58.2 \u00b5M. Molecular docking studies suggested that compounds\n                    <jats:bold>1<\/jats:bold>\n                    \u2013\n                    <jats:bold>7<\/jats:bold>\n                    , as monoterpene derivatives, are promising iNOS inhibitors rather than inhibitors of TNF\u2010\u03b1, COX\u20102, or IL\u20106 inflammatory cytokines.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.71445","type":"journal-article","created":{"date-parts":[[2026,6,24]],"date-time":"2026-06-24T09:46:39Z","timestamp":1782294399000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Two New Highly Oxygenated Monoterpenes From the Seeds of\n                    <i>Dysphania ambrosioides<\/i>\n                    and Their Inflammatory Activity In Vitro and In Silico"],"prefix":"10.1002","volume":"23","author":[{"given":"Nguyen Thi Viet","family":"Ai","sequence":"first","affiliation":[{"name":"VAST Graduate University of Science and Technology  Hanoi Vietnam"},{"name":"VAST Institute of Chemistry  Hanoi Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Phan Thi Thanh","family":"Huong","sequence":"additional","affiliation":[{"name":"National Institute of Drug Quality Control  Hanoi Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ngo Anh","family":"Bang","sequence":"additional","affiliation":[{"name":"National Institute of Drug Quality Control  Hanoi Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nguyen Huy","family":"Hoang","sequence":"additional","affiliation":[{"name":"National Institute of Drug Quality Control  Hanoi Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pham Hai","family":"Yen","sequence":"additional","affiliation":[{"name":"National Institute of Drug Quality Control  Hanoi Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bui Huu","family":"Tai","sequence":"additional","affiliation":[{"name":"VAST Institute of Chemistry  Hanoi Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0756-6990","authenticated-orcid":false,"given":"Phan Van","family":"Kiem","sequence":"additional","affiliation":[{"name":"National Institute of Drug Quality Control  Hanoi Vietnam"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,6,24]]},"reference":[{"key":"e_1_2_10_2_1","first-page":"403","volume-title":"Bioactives and Pharmacology of Medicinal Plants","author":"Ajaib M.","year":"2023"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jff.2023.105712"},{"key":"e_1_2_10_4_1","first-page":"718","article-title":"Dictionary of Vietnamese Medicinal Plants","volume":"1","author":"Chi V. V.","year":"2012","journal-title":"Medical Publishing House"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cimid.2019.04.010"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.201700149"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jspr.2025.102839"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.1155\/2014\/930208"},{"key":"e_1_2_10_9_1","first-page":"31","article-title":"Chemical Constituents, Ethnomedicinal Uses, Pharmacology, and Toxicity of Dysphania Ambrosioides (L.) Mosyakin & Clemants, Formerly Chenopodium Ambrosioides L","volume":"12","author":"Kamdem B. P.","year":"2022","journal-title":"Journal of Natural Products"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1080\/00207233.2024.2433915"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1093\/jpp\/rgad046"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.49.840"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF00266280"},{"key":"e_1_2_10_14_1","first-page":"331","article-title":"Studies on the Constituents of the Water\u2010soluble Portion in Asiasari Radix","volume":"44","author":"Shoji Y.","year":"1990","journal-title":"Shoyakugaku Zasshi"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(91)83449-U"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/np990376u"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo8020506"},{"key":"e_1_2_10_18_1","first-page":"10","article-title":"4\u2010Hydroxy\u20104\u2010methylcyclohex\u20102\u2010en\u20101\u2010one Was Synthesized from 4\u2010Methylanisole. The Key Step Is the Regioselective Reaction of Singlet Oxygen With 4\u2010Methylcyclohex\u20103\u2010en\u20101\u2010one","volume":"1","author":"Vesile P.","year":"2006","journal-title":"Journal of Chemical Research"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.1515\/znc-1999-1201"},{"key":"e_1_2_10_20_1","first-page":"40","volume-title":"Bryophytes. Their Chemistry and Chemical Taxonomy","author":"Connolly J. D.","year":"1990"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202300785"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2021.112889"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.71445","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbdv.71445","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.71445","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,7,6]],"date-time":"2026-07-06T19:18:47Z","timestamp":1783365527000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.71445"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,6]]},"references-count":21,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2026,6]]}},"alternative-id":["10.1002\/cbdv.71445"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.71445","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,6]]},"assertion":[{"value":"2026-04-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-06-11","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-06-24","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71445"}}