{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,10]],"date-time":"2026-09-10T15:26:03Z","timestamp":1789053963351,"version":"build-2803163510"},"reference-count":31,"publisher":"Informa UK Limited","issue":"12","license":[{"start":{"date-parts":[[2018,12,2]],"date-time":"2018-12-02T00:00:00Z","timestamp":1543708800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"funder":[{"DOI":"10.13039\/501100003725","name":"Korean National Research Foundation","doi-asserted-by":"crossref","award":["NRF-2016R1C1B2007694 and NRF-2016K1A1A8A01938595"],"award-info":[{"award-number":["NRF-2016R1C1B2007694 and NRF-2016K1A1A8A01938595"]}],"id":[{"id":"10.13039\/501100003725","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100003627","name":"Rural Development Administration","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003627","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["www.tandfonline.com"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[2018,12,2]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n               <jats:p>A new biflavonoid, amentoflavone-7-O-\u03b2-D-glucoside, and thirteen known flavonoids were isolated from the fruits of Juniperus chinensis using a bioactivity-guided method and their tyrosinase inhibitory effects were tested using a mushroom tyrosinase bioassay. Two isolates, hypolaetin-7-O-\u03b2-D-glucoside and quercetin-7-O-\u03b1-L-rhamnoside, were found to reduce tyrosinase activity at a concentration of 50 \u03bcM. Quercetin-7-O-\u03b1-L-rhamnoside attenuated cellular tyrosinase activity and melanogenesis in \u03b1-MSH plus IBMX-stimulated B16F10 melanoma cells. Molecular docking simulation revealed that quercetin-7-O-\u03b1-L-rhamnoside inhibits tyrosinase activity by hydrogen bonding with residues His85, His244, Thr261, and Gly281 of tyrosinase.<\/jats:p>\n               <jats:p>Abbreviations: EtOH, ethanol; CH2Cl2, dichloromethane; EtOAc, ethylacetate; n-BuOH, n-butanol; MeOH, metanol; CHCl3,chloroform; DMSO, dimethylsulfoxide; DMEM, Dulbecco\u2019s modified Eagle\u2019s medium; FBS, fetal bovine serum; \u03b1-MSH, \u03b1-melanocyte stimulating hormone; L-DOPA, L-3, 4-dihydroxyphenylalanine<\/jats:p>","DOI":"10.1080\/09168451.2018.1511367","type":"journal-article","created":{"date-parts":[[2018,8,21]],"date-time":"2018-08-21T23:27:33Z","timestamp":1534894053000},"page":"2041-2048","update-policy":"https:\/\/doi.org\/10.1080\/tandf_crossmark_01","source":"Crossref","is-referenced-by-count":25,"title":["Isolation of tyrosinase and melanogenesis inhibitory flavonoids from <i>Juniperus chinensis<\/i> fruits"],"prefix":"10.1080","volume":"82","author":[{"given":"Sang-a","family":"Park","sequence":"first","affiliation":[{"name":"College of Pharmacy, Pusan National University, Busan, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jonghwan","family":"Jegal","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Pusan National University, Busan, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ki Wung","family":"Chung","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Pusan National University, Busan, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hee Jin","family":"Jung","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Pusan National University, Busan, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sang Gyun","family":"Noh","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Pusan National University, Busan, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hae Young","family":"Chung","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Pusan National University, Busan, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jongmin","family":"Ahn","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinwoong","family":"Kim","sequence":"additional","affiliation":[{"name":"College of Pharmacy and Research Institute of Pharmaceutical Sciences, Seoul National University, Seoul, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min Hye","family":"Yang","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Pusan National University, Busan, South Korea"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"301","published-online":{"date-parts":[[2018,12,2]]},"reference":[{"key":"2021033109582883100_CIT0001","doi-asserted-by":"crossref","first-page":"27557","DOI":"10.1074\/jbc.R700026200","article-title":"The regulation of skin pigmentation","volume":"282","author":"Yamaguchi","year":"2007","journal-title":"J Biol Chem"},{"key":"2021033109582883100_CIT0002","doi-asserted-by":"crossref","first-page":"843","DOI":"10.1038\/nature05660","article-title":"Melanocyte biology and skin pigmentation","volume":"445","author":"Lin","year":"2007","journal-title":"Nature"},{"key":"2021033109582883100_CIT0003","doi-asserted-by":"crossref","first-page":"1155","DOI":"10.1152\/physrev.00044.2003","article-title":"Melanin pigmentation in mammalian skin and its hormonal regulation","volume":"84","author":"Slominski","year":"2004","journal-title":"Physiol Rev"},{"key":"2021033109582883100_CIT0004","doi-asserted-by":"crossref","first-page":"193","DOI":"10.1002\/biof.29","article-title":"Physiological factors that regulate skin pigmentation","volume":"35","author":"Yamaguchi","year":"2009","journal-title":"Biofactors"},{"key":"2021033109582883100_CIT0005","doi-asserted-by":"crossref","first-page":"2440","DOI":"10.3390\/ijms10062440","article-title":"An updated review of tyrosinase inhibitors","volume":"10","author":"Chang","year":"2009","journal-title":"Int J Mol Sci"},{"key":"2021033109582883100_CIT0006","doi-asserted-by":"crossref","first-page":"63","DOI":"10.1111\/j.1600-0536.2009.01673.x","article-title":"Pigmented contact dermatitis due to kojic acid. A paradoxical side effect of a skin lightener","volume":"62","author":"Garcia-Gavin","year":"2010","journal-title":"Contact Dermatitis"},{"key":"2021033109582883100_CIT0007","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1111\/j.1529-8019.2007.00144.x","article-title":"Skin lightening preparations and the hydroquinone controversy","volume":"20","author":"Draelos","year":"2007","journal-title":"Dermatol Ther"},{"key":"2021033109582883100_CIT0008","doi-asserted-by":"crossref","first-page":"479","DOI":"10.1089\/acm.2016.0405","article-title":"Integrative skin care: dermatology and traditional and complementary medicine","volume":"23","author":"Bodeker","year":"2017","journal-title":"J Altern Complement Med"},{"key":"2021033109582883100_CIT0009","doi-asserted-by":"crossref","first-page":"1415","DOI":"10.1248\/bpb.31.1415","article-title":"Anti-obesity effects of Juniperus chinensis extract are associated with increased AMP-activated protein kinase expression and phosphorylation in the visceral adipose tissue of rats","volume":"31","author":"Kim","year":"2008","journal-title":"Biol Pharm Bull"},{"key":"2021033109582883100_CIT0010","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1016\/0378-8741(96)01434-1","article-title":"Antitumour-promoting and antitumour activities of the crude extract from the leaves of Juniperus chinensis","volume":"53","author":"Ali","year":"1996","journal-title":"J Ethnopharmacol"},{"key":"2021033109582883100_CIT0011","first-page":"398","article-title":"Medicinal plants of China. Vol. 2","volume":"98","author":"Duke","year":"1985","journal-title":"Feddes Repert"},{"key":"2021033109582883100_CIT0012","doi-asserted-by":"crossref","first-page":"6596","DOI":"10.1021\/jf070257h","article-title":"Flavonoids and biflavonoids in Tuscan berries of Juniperus communis L.: detection and quantitation by HPLC\/DAD\/ESI\/MS","volume":"55","author":"Innocenti","year":"2007","journal-title":"J Agric Food Chem"},{"key":"2021033109582883100_CIT0013","doi-asserted-by":"crossref","DOI":"10.1142\/3469","volume-title":"International collation of traditional and folk medicine: Northeast Asia\u2013part II","author":"But","year":"1997"},{"key":"2021033109582883100_CIT0014","doi-asserted-by":"crossref","first-page":"2600","DOI":"10.1016\/j.fct.2011.07.004","article-title":"Phenolic composition and biological activities of Juniperus drupacea Labill. berries from Turkey","volume":"49","author":"Miceli","year":"2011","journal-title":"Food Chem Toxicol"},{"key":"2021033109582883100_CIT0015","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3109\/14756366.2015.1004058","article-title":"Natural, semisynthetic and synthetic tyrosinase inhibitors","volume":"31","author":"Lee","year":"2016","journal-title":"J Enzyme Inhib Med Chem"},{"key":"2021033109582883100_CIT0016","doi-asserted-by":"crossref","first-page":"1707","DOI":"10.1007\/s00018-005-5054-y","article-title":"Tyrosinase inhibitors from natural and synthetic sources: structure, inhibition mechanism and perspective for the future","volume":"62","author":"Kim","year":"2005","journal-title":"Cell Mol Life Sci"},{"key":"2021033109582883100_CIT0017","doi-asserted-by":"crossref","first-page":"270","DOI":"10.4161\/oxim.2.5.9498","article-title":"Plant polyphenols as dietary antioxidants in human health and disease","volume":"2","author":"Pandey","year":"2009","journal-title":"Oxid Med Cell Longev"},{"key":"2021033109582883100_CIT0018","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1080\/13590840220123352","article-title":"Flavonoids and other plant phenols in the diet: their significance as antioxidants","volume":"12","author":"Miller","year":"2002","journal-title":"J Nutr Environ Med"},{"key":"2021033109582883100_CIT0019","doi-asserted-by":"crossref","first-page":"1264","DOI":"10.1248\/cpb.51.1264","article-title":"Uncinoside A and B, two new antiviral chromone glycosides from Selaginella uncinata","volume":"51","author":"Ma","year":"2003","journal-title":"Chem Pharm Bull"},{"key":"2021033109582883100_CIT0020","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1007\/BF00568647","article-title":"Hypolaetin 7-glucoside from Caryopteris monolica","volume":"9","author":"Zapesochnaya","year":"1973","journal-title":"Chem Nat Compd"},{"key":"2021033109582883100_CIT0021","first-page":"247","article-title":"Flavones and flavone glycosides from Salvia macrosiphon Boiss","volume":"10","author":"Gohari","year":"2011","journal-title":"Iran J Pharm Res"},{"key":"2021033109582883100_CIT0022","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1016\/j.phytochem.2003.10.025","article-title":"Neolignan and flavonoid glycosides in Juniperus communis var. depressa","volume":"65","author":"Nakanishi","year":"2004","journal-title":"Phytochemistry"},{"key":"2021033109582883100_CIT0023","doi-asserted-by":"crossref","first-page":"4624","DOI":"10.1016\/j.bmcl.2006.06.011","article-title":"Hepatoprotective activity of Schouwia thebica webb","volume":"16","author":"Amani","year":"2006","journal-title":"Bioorg Med Chem Lett"},{"key":"2021033109582883100_CIT0024","first-page":"180","article-title":"Polyphenols from longan leaf and their radical-scavenging activity","volume":"50","author":"Wu","year":"2013","journal-title":"Int Proc Chem Biol Environ"},{"key":"2021033109582883100_CIT0025","doi-asserted-by":"crossref","first-page":"3335","DOI":"10.1016\/S0031-9422(00)82499-1","article-title":"13C NMR studies of some naturally occurring amentoflavone and hinokiflavone bioflavonoids","volume":"26","author":"Markham","year":"1987","journal-title":"Phytochemistry"},{"key":"2021033109582883100_CIT0026","doi-asserted-by":"crossref","first-page":"496","DOI":"10.1080\/13880200902838717","article-title":"Isolation and structural elucidation of chemical constituents of Amanoa almerindae","volume":"47","author":"Leong","year":"2009","journal-title":"Pharm Biol"},{"key":"2021033109582883100_CIT0027","doi-asserted-by":"crossref","first-page":"614","DOI":"10.3390\/80800614","article-title":"Constituents from Moghat, the roots of Glossostemon bruguieri (Desf.)","volume":"8","author":"Meselhy","year":"2003","journal-title":"Molecules"},{"key":"2021033109582883100_CIT0028","doi-asserted-by":"crossref","first-page":"6533","DOI":"10.1016\/j.tetlet.2005.07.091","article-title":"A pair of new atropisomeric cupressuflavone glucosides isolated from Juniperus communis var. depressa","volume":"46","author":"Inatomi","year":"2005","journal-title":"Tetrahedron Lett"},{"key":"2021033109582883100_CIT0029","doi-asserted-by":"crossref","first-page":"2173","DOI":"10.1002\/rcm.5090","article-title":"Structural characterization and identification of biflavones in Selaginella tamariscina by liquid chromatography-diode-array detection\/electrospray ionization tandem mass spectrometry","volume":"25","author":"Zhang","year":"2011","journal-title":"Rapid Commun Mass Spectrom"},{"key":"2021033109582883100_CIT0030","doi-asserted-by":"crossref","first-page":"2311","DOI":"10.1080\/09168451.2016.1217146","article-title":"Tyrosinase inhibitory flavonoid from Juniperus communis fruits","volume":"80","author":"Jegal","year":"2016","journal-title":"Biosci Biotechnol Biochem"},{"key":"2021033109582883100_CIT0031","doi-asserted-by":"crossref","first-page":"4108","DOI":"10.1021\/jf011378z","article-title":"Kinetics of mushroom tyrosinase inhibition by quercetin","volume":"50","author":"Chen","year":"2002","journal-title":"J Agri Food Chem"}],"container-title":["Bioscience, Biotechnology, and Biochemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/academic.oup.com\/bbb\/article-pdf\/82\/12\/2041\/36831553\/bbb2041.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"http:\/\/academic.oup.com\/bbb\/article-pdf\/82\/12\/2041\/36831553\/bbb2041.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,6,7]],"date-time":"2022-06-07T11:52:37Z","timestamp":1654602757000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/bbb\/article\/82\/12\/2041\/5955785"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,12,2]]},"references-count":31,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2018,12,2]]},"published-print":{"date-parts":[[2018,12,2]]}},"URL":"https:\/\/doi.org\/10.1080\/09168451.2018.1511367","relation":{},"ISSN":["0916-8451","1347-6947"],"issn-type":[{"value":"0916-8451","type":"print"},{"value":"1347-6947","type":"electronic"}],"subject":[],"published-other":{"date-parts":[[2018,12,2]]},"published":{"date-parts":[[2018,12,2]]},"assertion":[{"value":"The publishing and review policy for this title is described in its Aims & Scope.","order":1,"name":"peerreview_statement","label":"Peer Review Statement"},{"value":"http:\/\/www.tandfonline.com\/action\/journalInformation?show=aimsScope&journalCode=tbbb20","URL":"http:\/\/www.tandfonline.com\/action\/journalInformation?show=aimsScope&journalCode=tbbb20","order":2,"name":"aims_and_scope_url","label":"Aim & Scope"},{"value":"2018-07-17","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-08-01","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-08-21","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}