{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,7]],"date-time":"2025-10-07T05:33:46Z","timestamp":1759815226870,"version":"3.41.2"},"reference-count":20,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2019,3,19]],"date-time":"2019-03-19T00:00:00Z","timestamp":1552953600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2019,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A new dinorcassane diterpenoid, seikphoochinal A (<jats:bold>1<\/jats:bold>), and four known compounds, pinostrobin (<jats:bold>2<\/jats:bold>), 4\u2032,7\u2010dimethylkaempferol (<jats:bold>3<\/jats:bold>), and galanals A (<jats:bold>4<\/jats:bold>) and B (<jats:bold>5<\/jats:bold>), were isolated from the chloroform\u2010soluble crude extract of wild type <jats:italic>Boesenbergia rotunda<\/jats:italic> rhizomes collected in Lower Myanmar. The chemical structures of these compounds were identified, using a combination of spectroscopic methods. The presence of the diterpenoids <jats:bold>1<\/jats:bold>, <jats:bold>4<\/jats:bold>, and <jats:bold>5<\/jats:bold> demonstrated the structural diversity of wild type <jats:italic>B. rotunda<\/jats:italic>. Among the isolates, compounds <jats:bold>4<\/jats:bold> and <jats:bold>5<\/jats:bold> exhibited significant antiproliferative activities against a small panel of human cancer cell lines, including lung (LK\u20102, A549), stomach (ECC4), breast (MCF7), cervix (HeLa), and prostate (DU145).<\/jats:p>","DOI":"10.1002\/cbdv.201800657","type":"journal-article","created":{"date-parts":[[2019,1,15]],"date-time":"2019-01-15T18:44:36Z","timestamp":1547577876000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Dinorcassane Diterpenoid from <i>Boesenbergia rotunda<\/i> Rhizomes Collected in Lower Myanmar"],"prefix":"10.1002","volume":"16","author":[{"given":"Nwet Nwet","family":"Win","sequence":"first","affiliation":[{"name":"Institute of Natural Medicine University of Toyama, 2630-Sugitani  Toyama 930-0194 Japan"},{"name":"Department of Chemistry University of Yangon  Yangon 11041 Myanmar"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"May Mon","family":"Kyaw","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Yangon  Yangon 11041 Myanmar"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"family":"Prema","sequence":"additional","affiliation":[{"name":"Institute of Natural Medicine University of Toyama, 2630-Sugitani  Toyama 930-0194 Japan"},{"name":"Department of Chemistry University of Yangon  Yangon 11041 Myanmar"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hla","family":"Ngwe","sequence":"additional","affiliation":[{"name":"Department of Chemistry University of Yangon  Yangon 11041 Myanmar"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Takuya","family":"Ito","sequence":"additional","affiliation":[{"name":"Faculty of Pharmacy Osaka Ohtani University, 3-11-1 Nisikiori-kita, Tondabayashi  Osaka 584-8540 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yoshinori","family":"Asakawa","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences Tokushima Bunri University, Yamashiro-cho  Tokushima 770-8514 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yasuko","family":"Okamoto","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences Tokushima Bunri University, Yamashiro-cho  Tokushima 770-8514 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Masami","family":"Tanaka","sequence":"additional","affiliation":[{"name":"Faculty of Pharmaceutical Sciences Tokushima Bunri University, Yamashiro-cho  Tokushima 770-8514 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ikuro","family":"Abe","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku  Tokyo 113-0033 Japan"},{"name":"Collaborative Research Institute for Innovative Microbiology The University of Tokyo, Yayoi 1-1-1, Bunkyo-ku  Tokyo 113-8657 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hiroyuki","family":"Morita","sequence":"additional","affiliation":[{"name":"Institute of Natural Medicine University of Toyama, 2630-Sugitani  Toyama 930-0194 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,3,19]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"crossref","unstructured":"B.\u2005C. Tan S.\u2005K. Tan S.\u2005M. Wong N. Ata N.\u2005A. Rahman N. Khalid \u2018Distribution of flavonoids and cyclohexenyl chalcone derivatives in conventional propagated andin\u2005vitro-derived field-grownBoesenbergia rotunda(L.) Mansf.\u2019 Evidence-Based Complem. Altern. Med.2015 2015 451870.","DOI":"10.1155\/2015\/451870"},{"key":"e_1_2_7_2_1","doi-asserted-by":"crossref","unstructured":"G. Trakoontivakorn K. Nakahara H. Shinmoto M. Takenaka M. Onishi-Kameyama H. Ono M. Yoshida T. Nagata T. Tsushida \u2018Structural analysis of a novel antimutagenic compound 4-hydroxypanduratin A and the antimutagenic activity of flavonoids in Thai spice fingerroot (Boesenbergia pandurataSchult.) against mutagenic heterocyclic amines\u2019 J. Agric. Food Chem.2001 49 3046\u20133050.","DOI":"10.1021\/jf010016o"},{"key":"e_1_2_7_3_1","doi-asserted-by":"crossref","unstructured":"A. Chahyadi R. Hartati K.\u2005R. Wirasutisna Elfahmi \u2018Boesenbergia pandurataRoxb. an Indonesian medicinal plant: Phytochemistry biological activity plant biotechnology\u2019 Procedia Chem.2014 13 13\u201337.","DOI":"10.1016\/j.proche.2014.12.003"},{"key":"e_1_2_7_4_1","doi-asserted-by":"crossref","unstructured":"T. Eng-Chong L. Yean-Kee C. Chin-Fei H. Choon-Han W. Sher-Ming C.\u2005T. Li-Ping F. Gen-Teck N. Khalid N. Abd Rahman S.\u2005A. Karsani S. Othman R. Othman R. Yusof \u2018Boesenbergia rotunda: from ethnomedicine to drug discovery\u2019 Evidence-Based Complem. Altern. Med.2012 2012 473637.","DOI":"10.1155\/2012\/473637"},{"key":"e_1_2_7_5_1","doi-asserted-by":"crossref","unstructured":"N.\u2005T. Nguyen M.\u2005T.\u2005T. Nguyen H.\u2005X. Nguyen P.\u2005H. Dang D.\u2005F. Dibwe H. Esumi S. Awale \u2018Constituents of the rhizomes ofBoesenbergia pandurataand their antiausterity activities against the PANC-1 human pancreatic cancer line\u2019 J. Nat. Prod.2017 80 141\u2013148.","DOI":"10.1021\/acs.jnatprod.6b00784"},{"key":"e_1_2_7_6_1","doi-asserted-by":"crossref","unstructured":"N.\u2005N. Win S. Awale H. Esumi Y. Tezuka S. Kadota \u2018Bioactive secondary metabolites fromBoesenbergia pandurataof Myanmar and their preferential cytotoxicity against human pancreatic cancer Panc-1\u2005cell line in nutrient-deprived medium\u2019 J. Nat. Prod.2007 70 1582\u20131587.","DOI":"10.1021\/np070286m"},{"key":"e_1_2_7_7_1","doi-asserted-by":"crossref","unstructured":"N.\u2005N. Win S. Awale H. Esumi Y. Tezuka S. Kadota \u2018Panduratins D\u2013I novel secondary metabolites from rhizomes ofBoesenbergia pandurata\u2019 Chem. Pharm. Bull.2008 54 491\u2013496.","DOI":"10.1248\/cpb.56.491"},{"key":"e_1_2_7_8_1","doi-asserted-by":"crossref","unstructured":"N.\u2005N. Win H. Ngwe I. Abe H. Morita \u2018Naturally occurring Vpr inhibitors from medicinal plants of Myanmar\u2019 J. Nat. Med.2017 71 579\u2013589.","DOI":"10.1007\/s11418-017-1104-7"},{"key":"e_1_2_7_9_1","doi-asserted-by":"crossref","unstructured":"N.\u2005N. Win T. Ito H. Ngwe Y.\u2005Y. Win Prema Y. Okamoto M. Tanaka Y. Asakawa I. Abe H. Morita \u2018Labdane diterpenoids fromCurcuma amadarhizomes collected in Myanmar\u2019 Fitoterapia2017 122 34\u201339.","DOI":"10.1016\/j.fitote.2017.08.006"},{"key":"e_1_2_7_10_1","doi-asserted-by":"crossref","unstructured":"N.\u2005N. Win T. Ito Ismail T. Kodama Y.\u2005Y. Win M. Tanaka Y. Okamoto H. Imagawa H. Ngwe Y. Asakawa I. Abe H. Morita \u2018Picrajavanicins H\u2212M: new quassinoids fromPicrasma javanicacollected in Myanmar and their antiproliferative activities\u2019 Tetrahedron2016 72 746\u2013752.","DOI":"10.1016\/j.tet.2015.12.030"},{"key":"e_1_2_7_11_1","doi-asserted-by":"crossref","unstructured":"N.\u2005N. Win T. Ito Ismail T. Kodama Y.\u2005Y. Win M. Tanaka H. Ngwe Y. Asakawa I. Abe H. Morita \u2018Picrajavanicins A\u2212G quassinoids fromPicrasma javanicacollected in Myanmar\u2019 J. Nat. Prod.2015 78 3024\u20133030.","DOI":"10.1021\/acs.jnatprod.5b00824"},{"key":"e_1_2_7_12_1","unstructured":"M. Suffness J.\u2005M. Pezzuto \u2018Assays related to cancer drug discovery\u2019 in \u2018Methods in Plant Biochemistry: Assays for Bioactivity\u2019 Ed. K. Hostettmann Academic Press London 1990 Vol. 6 pp. 71\u2013133."},{"key":"e_1_2_7_13_1","doi-asserted-by":"crossref","unstructured":"Y.-H. Kuo C.-I. Chang C.-K. Lee \u2018Six podocarpane-type trinorditerpenes from the bark ofTaiwania cryptomerioides\u2019 Chem. Pharm. Bull.2000 48 597\u2013599.","DOI":"10.1248\/cpb.48.597"},{"key":"e_1_2_7_14_1","unstructured":"A.\u2005Y.\u2005L. Ching T.\u2005S. Wah M.\u2005A. Sukari G.\u2005E.\u2005C. Lian M. Rahmani K. Khalid \u2018Characterization of flavonoid derivatives fromBoesenbergia rotunda(L.)\u2019 Malays. J. Anal. Sci.2007 11 154\u2013159."},{"key":"e_1_2_7_15_1","unstructured":"J. Zhang Q. Guo L. Kong \u2018Flavonoids from rhizome ofAlpinia tonkinensis\u2019 China J. Chin. Mater. Med.2003 28 41\u201343."},{"key":"e_1_2_7_16_1","doi-asserted-by":"crossref","unstructured":"H. Morita H. Itokawa \u2018New diterpenes fromAlpinia galangaWild.\u2019 Chem. Lett.1986 15 1205\u20131208.","DOI":"10.1246\/cl.1986.1205"},{"key":"e_1_2_7_17_1","doi-asserted-by":"crossref","unstructured":"M. Abe Y. Ozawa Y. Uda Y. Morimitsu Y. Nakamura T. Osawa \u2018A novel labdane-type trialdehyde from Myoga (Zingiber miogaRoscoe) that potently inhibits human platelet aggregation and human 5-lipoxygenase\u2019 Biosci. Biotechnol. Biochem.2006 70 2494\u20132500.","DOI":"10.1271\/bbb.60226"},{"key":"e_1_2_7_18_1","doi-asserted-by":"crossref","unstructured":"N. Miyoshi Y. Nakamura Y. Ueda M. Abe Y. Ozawa K. Uchida T. Osawa \u2018Dietary ginger constituents galanals A and B are potent apoptosis inducers in human T lymphoma Jurkat cells\u2019 Cancer Lett.2003 199 113\u2013119.","DOI":"10.1016\/S0304-3835(03)00381-1"},{"key":"e_1_2_7_19_1","doi-asserted-by":"crossref","unstructured":"R. Yamamoto Y. Yamamoto S. Imai R. Fukutomi Y. Ozawa M. Abe Y. Matuo K. Saito \u2018Effects of various phytochemicals on indoleamine 2 3-dioxygenase 1 activity: galanal is a novel competitive inhibitor of the enzyme\u2019 PLoS One2014 9 e88789.","DOI":"10.1371\/journal.pone.0088789"},{"key":"e_1_2_7_20_1","doi-asserted-by":"crossref","unstructured":"N.\u2005N. Win T. Ito S. Aimaiti H. Imagawa H. Ngwe I. Abe H. Morita \u2018Kaempulchraols A\u2212H diterpenoids from the rhizomes ofKaempferia pulchracollected in Myanmar\u2019 J. Nat. Prod.2015 78 1113\u20131118.","DOI":"10.1021\/acs.jnatprod.5b00108"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbdv.201800657","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.201800657","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbdv.201800657","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.201800657","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,9]],"date-time":"2023-09-09T11:08:20Z","timestamp":1694257700000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.201800657"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,3,19]]},"references-count":20,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2019,4]]}},"alternative-id":["10.1002\/cbdv.201800657"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.201800657","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"type":"print","value":"1612-1872"},{"type":"electronic","value":"1612-1880"}],"subject":[],"published":{"date-parts":[[2019,3,19]]},"assertion":[{"value":"2018-12-08","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-01-15","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-03-19","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e1800657"}}