{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,19]],"date-time":"2026-06-19T17:10:38Z","timestamp":1781889038469,"version":"3.54.5"},"reference-count":39,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2023,12,1]],"date-time":"2023-12-01T00:00:00Z","timestamp":1701388800000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100003725","name":"National Research Foundation of Korea","doi-asserted-by":"publisher","award":["NRF-2022R1A2C1010084"],"award-info":[{"award-number":["NRF-2022R1A2C1010084"]}],"id":[{"id":"10.13039\/501100003725","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003621","name":"Ministry of Science, ICT and Future Planning","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003621","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Phytochemistry"],"published-print":{"date-parts":[[2023,12]]},"DOI":"10.1016\/j.phytochem.2023.113864","type":"journal-article","created":{"date-parts":[[2023,9,23]],"date-time":"2023-09-23T19:16:34Z","timestamp":1695496594000},"page":"113864","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":7,"special_numbering":"C","title":["Stereochemical assignment of clerodane-type diterpenes from the fruits of Casearia grewiifolia and their ability to inhibit PCSK9 expression"],"prefix":"10.1016","volume":"216","author":[{"given":"Piseth","family":"Nhoek","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9157-5883","authenticated-orcid":false,"given":"Chae-Yeong","family":"An","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min-Gyung","family":"Son","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9625-6980","authenticated-orcid":false,"given":"Hee-Sung","family":"Chae","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9907-766X","authenticated-orcid":false,"given":"Pisey","family":"Pel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Young-Mi","family":"Kim","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1868-037X","authenticated-orcid":false,"given":"Piseth","family":"Khiev","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2342-0468","authenticated-orcid":false,"given":"Won Jun","family":"Choi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9360-6436","authenticated-orcid":false,"given":"Young Hee","family":"Choi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Young-Won","family":"Chin","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"78","reference":[{"key":"10.1016\/j.phytochem.2023.113864_bib1","doi-asserted-by":"crossref","first-page":"1440","DOI":"10.3390\/nu12051440","article-title":"Naturally occurring PCSK9 inhibitors","volume":"12","author":"Adorni","year":"2020","journal-title":"Nutrients"},{"key":"10.1016\/j.phytochem.2023.113864_bib2","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1016\/j.bse.2007.03.003","article-title":"Clerodane diterpenes from the stems of Casearia grewiifolia var. gelonioides (Flacourtiaceae\/Salicaceae sensu lato)","volume":"35","author":"Ashik Mosaddik","year":"2007","journal-title":"Biochem. Systemat. Ecol."},{"key":"10.1016\/j.phytochem.2023.113864_bib3","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1039\/C0OB00479K","article-title":"Interproton distance determinations by NOE\u2013surprising accuracy and precision in a rigid organic molecule","volume":"9","author":"Butts","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"10.1016\/j.phytochem.2023.113864_bib4","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1021\/np400672g","article-title":"Cytotoxic clerodane diterpenes from Zuelania guidonia","volume":"77","author":"Calderon","year":"2014","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib5","doi-asserted-by":"crossref","first-page":"31126","DOI":"10.1021\/acsomega.0c04282","article-title":"Transcriptome analysis illuminates a hub role of SREBP2 in cholesterol metabolism by \u03b1-mangostin","volume":"5","author":"Chae","year":"2020","journal-title":"ACS Omega"},{"key":"10.1016\/j.phytochem.2023.113864_bib6","doi-asserted-by":"crossref","DOI":"10.1016\/j.jep.2021.114265","article-title":"Identification of neolignans with PCSK9 downregulatory and LDLR upregulatory activities from Penthorum chinense and the potential in cholesterol uptake by transcriptional regulation of LDLR via SREBP2","volume":"278","author":"Chae","year":"2021","journal-title":"J. Ethnopharmacol."},{"issue":"1","key":"10.1016\/j.phytochem.2023.113864_bib7","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1038\/s41598-020-76224-w","article-title":"Platycodin D enhances LDLR expression and LDL uptake via down-regulation of IDOL mRNA in hepatic cells","volume":"10","author":"Choi","year":"2020","journal-title":"Sci. Rep."},{"key":"10.1016\/j.phytochem.2023.113864_bib9","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1039\/C6AN02298G","article-title":"Accurate measurement of long range proton\u2013carbon scalar coupling constants","volume":"142","author":"Dickson","year":"2017","journal-title":"Analyst"},{"key":"10.1016\/j.phytochem.2023.113864_bib10","series-title":"Gaussian 16","author":"Frisch","year":"2009"},{"key":"10.1016\/j.phytochem.2023.113864_bib11","doi-asserted-by":"crossref","first-page":"5517","DOI":"10.3390\/nu6125517","article-title":"PCSK9 antibodies for the treatment of hypercholesterolemia","volume":"6","author":"Gouni-Berthold","year":"2014","journal-title":"Nutrients"},{"key":"10.1016\/j.phytochem.2023.113864_bib12","doi-asserted-by":"crossref","first-page":"12526","DOI":"10.1021\/acs.joc.5b02396","article-title":"Beyond DP4: an improved probability for the stereochemical assignment of isomeric compounds using quantum chemical calculations of NMR shifts","volume":"80","author":"Grimblat","year":"2015","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.phytochem.2023.113864_bib13","doi-asserted-by":"crossref","first-page":"145","DOI":"10.3762\/bjoc.7.20","article-title":"Accuracy in determining interproton distances using nuclear overhauser effect data from a flexible molecule","volume":"7","author":"Jones","year":"2011","journal-title":"Beilstein J. Org. Chem."},{"key":"10.1016\/j.phytochem.2023.113864_bib14","doi-asserted-by":"crossref","first-page":"183","DOI":"10.1021\/np049757k","article-title":"New bioactive clerodane diterpenoids from the bark of Casearia grewiifolia","volume":"68","author":"Kanokmedhakul","year":"2005","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib15","doi-asserted-by":"crossref","first-page":"1122","DOI":"10.1021\/np070083y","article-title":"Cytotoxic clerodane diterpenoids from fruits of Casearia grewiifolia","volume":"70","author":"Kanokmedhakul","year":"2007","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib16","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1006\/jmra.1996.0132","article-title":"Excitation-sculptured indirect-detection experiment (EXSIDE) for long-range CH coupling-constant measurement","volume":"121","author":"Krishnamurithy","year":"1996","journal-title":"J. Magn. Reson., Ser. A A."},{"key":"10.1016\/j.phytochem.2023.113864_bib17","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1097\/MOL.0000000000000114","article-title":"PCSK9 and LDLR degradation: regulatory mechanisms in circulation and in cells","volume":"25","author":"Lagace","year":"2014","journal-title":"Curr. Opin. Lipidol."},{"issue":"3","key":"10.1016\/j.phytochem.2023.113864_bib18","doi-asserted-by":"crossref","first-page":"538","DOI":"10.1093\/ndt\/gft439","article-title":"Role of PCSK9 and IDOL in the pathogenesis of acquired LDL receptor deficiency and hypercholesterolemia in nephrotic syndrome","volume":"29","author":"Liu","year":"2014","journal-title":"Nephrol. Dial. Transplant."},{"issue":"39","key":"10.1016\/j.phytochem.2023.113864_bib19","doi-asserted-by":"crossref","first-page":"13570","DOI":"10.1074\/jbc.RA120.014349","article-title":"Structural analysis of the LDL receptor\u2013interacting FERM domain in the E3 ubiquitin ligase IDOL reveals an obscured substrate-binding site","volume":"295","author":"Martinelli","year":"2020","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.phytochem.2023.113864_bib20","doi-asserted-by":"crossref","first-page":"866","DOI":"10.1021\/jo981810k","article-title":"Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants. A method of configuration analysis for natural products","volume":"64","author":"Matsumori","year":"1999","journal-title":"J. Org. Chem."},{"key":"10.1016\/j.phytochem.2023.113864_bib21","doi-asserted-by":"crossref","first-page":"2726","DOI":"10.1021\/acs.jnatprod.5b00677","article-title":"Cytotoxic clerodane diterpenoids from the leaves of Casearia grewiifolia","volume":"78","author":"Nguyen","year":"2015","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib22","doi-asserted-by":"crossref","first-page":"2437","DOI":"10.1021\/acs.jnatprod.1c00343","article-title":"Salicinoyl quinic acids and their prostaglandin E2 production inhibitory activities from the fruits of Casearia grewiifolia","volume":"84","author":"Nhoek","year":"2021","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib23","doi-asserted-by":"crossref","first-page":"220","DOI":"10.1021\/acs.jnatprod.0c00829","article-title":"Sesquiterpenoids from the aerial parts of Salvia plebeia with inhibitory activities on proprotein convertase subtilisin\/kexin type 9 expression","volume":"84","author":"Nhoek","year":"2021","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib24","article-title":"Alkaloids and coumarins with adiponectin-secretion-promoting activities from the leaves of Orixa japonica","author":"Nhoek","year":"2022","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib25","doi-asserted-by":"crossref","first-page":"1595","DOI":"10.1194\/jlr.CX00001-JLR200","article-title":"PCSK9 function and physiology","volume":"49","author":"Peterson","year":"2008","journal-title":"J. Lipid Res."},{"key":"10.1016\/j.phytochem.2023.113864_bib26","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1016\/j.phytol.2011.09.007","article-title":"New phenolics from the wood of Casearia grewiifolia","volume":"5","author":"Rayanil","year":"2012","journal-title":"Phytochem. Lett."},{"key":"10.1016\/j.phytochem.2023.113864_bib27","doi-asserted-by":"crossref","first-page":"45","DOI":"10.1007\/s11883-021-00938-z","article-title":"Novel RNAi-based therapies for atherosclerosis","volume":"23","author":"Ruotsalainen","year":"2021","journal-title":"Curr. Atherosclerosis Rep."},{"key":"10.1016\/j.phytochem.2023.113864_bib28","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1021\/np010405c","article-title":"Structure and stereochemistry of new cytotoxic clerodane diterpenoids from the bark of Casearia lucida from the Madagascar rainforest","volume":"65","author":"Sai Prakash","year":"2002","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib29","article-title":"The PCSK9 discovery, an inactive protease with varied functions in hypercholesterolemia, viral infections, and cancer","volume":"62","author":"Seidah","year":"2021","journal-title":"Lipid Res"},{"key":"10.1016\/j.phytochem.2023.113864_bib30","doi-asserted-by":"crossref","first-page":"316","DOI":"10.1021\/np0303658","article-title":"New Cytotoxic clerodane diterpenoids from the leaves and twigs of Casearia membranacea","volume":"67","author":"Shen","year":"2004","journal-title":"J. Nat. Prod."},{"issue":"6","key":"10.1016\/j.phytochem.2023.113864_bib31","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1007\/s12170-010-0131-7","article-title":"Clinical implications of lipid genetics for cardiovascular disease","volume":"4","author":"Strong","year":"2010","journal-title":"Curr. Cardiovasc. Risk Rep."},{"key":"10.1016\/j.phytochem.2023.113864_bib32","doi-asserted-by":"crossref","first-page":"1065","DOI":"10.1021\/acs.jnatprod.6b01151","article-title":"Corymbulosins D\u2212H, 2-hydroxy- and 2-oxo-clerodane diterpenes from the bark of Laetia corymbulosa","volume":"80","author":"Suzuki","year":"2017","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib33","doi-asserted-by":"crossref","first-page":"776","DOI":"10.1021\/np100840w","article-title":"Cytotoxic clerodane diterpenes from Casearia rupestris","volume":"74","author":"Vieira-Junior","year":"2011","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib34","doi-asserted-by":"crossref","first-page":"1573","DOI":"10.1021\/np400212d","article-title":"Cytotoxic clerodane diterpenoids from the leaves and twigs of Casearia balansae","volume":"76","author":"Wang","year":"2013","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib35","article-title":"SUMOylation of the ubiquitin ligase IDOL decreases LDL receptor levels and is reversed by SENP1","volume":"296","author":"Wang","year":"2021","journal-title":"J. Biol. Chem."},{"key":"10.1016\/j.phytochem.2023.113864_bib36","doi-asserted-by":"crossref","first-page":"206","DOI":"10.1021\/np0605034","article-title":"Cytotoxic clerodane diterpenoids and their hydrolysis products from Casearia nigrescens from the rainforest of Madagascar","volume":"70","author":"Williams","year":"2007","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib37","doi-asserted-by":"crossref","first-page":"2648","DOI":"10.1021\/acs.jnatprod.5b00583","article-title":"Characterization and biological evaluation of diterpenoids from Casearia graveolens","volume":"78","author":"Xu","year":"2015","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib38","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1021\/acs.jnatprod.5b00815","article-title":"Di- and triterpenoids from the leaves of Casearia balansae and neurite outgrowth promoting effects of PC12 cells","volume":"79","author":"Xu","year":"2015","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib39","doi-asserted-by":"crossref","first-page":"2182","DOI":"10.1021\/np5003516","article-title":"Bioactive clerodane diterpenoids from the twigs of Casearia balansae","volume":"77","author":"Xu","year":"2014","journal-title":"J. Nat. Prod."},{"key":"10.1016\/j.phytochem.2023.113864_bib40","doi-asserted-by":"crossref","first-page":"18602","DOI":"10.1074\/jbc.M702027200","article-title":"Binding of proprotein convertase subtilisin\/kexin type 9 to epidermal growth factor-like repeat a of low density lipoprotein receptor decreases receptor recycling and increases degradation","volume":"282","author":"Zhang","year":"2007","journal-title":"J. Biol. Chem."}],"container-title":["Phytochemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0031942223002807?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0031942223002807?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,9,21]],"date-time":"2025-09-21T18:52:27Z","timestamp":1758480747000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0031942223002807"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,12]]},"references-count":39,"alternative-id":["S0031942223002807"],"URL":"https:\/\/doi.org\/10.1016\/j.phytochem.2023.113864","relation":{},"ISSN":["0031-9422"],"issn-type":[{"value":"0031-9422","type":"print"}],"subject":[],"published":{"date-parts":[[2023,12]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Stereochemical assignment of clerodane-type diterpenes from the fruits of Casearia grewiifolia and their ability to inhibit PCSK9 expression","name":"articletitle","label":"Article Title"},{"value":"Phytochemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.phytochem.2023.113864","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2023 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"113864"}}