{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T23:01:02Z","timestamp":1788303662177,"version":"build-2803163510"},"reference-count":34,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2015,10,9]],"date-time":"2015-10-09T00:00:00Z","timestamp":1444348800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["1RO1GM086307-01"],"award-info":[{"award-number":["1RO1GM086307-01"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000928","name":"Welch Foundation","doi-asserted-by":"publisher","award":["A-1828"],"award-info":[{"award-number":["A-1828"]}],"id":[{"id":"10.13039\/100000928","id-type":"DOI","asserted-by":"publisher"}]},{"name":"National Institute of Health","award":["P20GM103466"],"award-info":[{"award-number":["P20GM103466"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>A new bioactive macrolactone, nuiapolide (1) was identified from a marine cyanobacterium collected off the coast of Niihau, near Lehua Rock. The natural product exhibits anti-chemotactic activity at concentrations as low as 1.3 \u03bcM against Jurkat cells, cancerous T lymphocytes, and induces a G2\/M phase cell cycle shift. Structural characterization of the natural product revealed the compound to be a 40-membered macrolactone with nine hydroxyl functional groups and a rare tert-butyl carbinol residue.<\/jats:p>","DOI":"10.3390\/md13106274","type":"journal-article","created":{"date-parts":[[2015,10,9]],"date-time":"2015-10-09T11:37:33Z","timestamp":1444390653000},"page":"6274-6290","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":19,"title":["Macrolactone Nuiapolide, Isolated from a Hawaiian Marine Cyanobacterium, Exhibits Anti-Chemotactic Activity"],"prefix":"10.3390","volume":"13","author":[{"given":"Shogo","family":"Mori","sequence":"first","affiliation":[{"name":"Department of Chemistry, Texas A&M University, College Station, TX 77843, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Howard","family":"Williams","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Texas A&M University, College Station, TX 77843, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Davey","family":"Cagle","sequence":"additional","affiliation":[{"name":"Department of Natural Sciences, Hawaii Pacific University, Kaneohe, HI 96744, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kristopher","family":"Karanovich","sequence":"additional","affiliation":[{"name":"Department of Natural Sciences, Hawaii Pacific University, Kaneohe, HI 96744, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"F.","family":"Horgen","sequence":"additional","affiliation":[{"name":"Department of Natural Sciences, Hawaii Pacific University, Kaneohe, HI 96744, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Roger","family":"III","sequence":"additional","affiliation":[{"name":"Department of Veterinary Pathology, Texas A&M University, College Station, TX 77843, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Coran","family":"Watanabe","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Texas A&M University, College Station, TX 77843, USA"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2015,10,9]]},"reference":[{"key":"ref_1","first-page":"1","article-title":"La m\u00e9dicine m\u00e9sopotamienne","volume":"11\u201312","author":"Attinger","year":"2008","journal-title":"J. Med. Cuneif."},{"key":"ref_2","unstructured":"Nunn, J. (2002). Ancient Egyptian Medicine, University of Oklahoma Press."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/978-0-387-46401-5_1","article-title":"Curcumin: The Indian solid gold","volume":"595","author":"Aggarwal","year":"2007","journal-title":"Adv. Exp. Med. Biol."},{"key":"ref_4","first-page":"7984","article-title":"History of medicine in China","volume":"8","author":"Hong","year":"2004","journal-title":"McGill J. Med."},{"key":"ref_5","first-page":"226","article-title":"On the antibacterial action of cultures of a penicillium, with special reference to their use in the isolation of B. influenza","volume":"10","author":"Fleming","year":"1929","journal-title":"Br. J. Exp. Pathol."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"87","DOI":"10.5598\/imafungus.2011.02.01.12","article-title":"Fleming\u2019s penicillin producing strain is not Penicillium chrysogenum but P. rubens","volume":"2","author":"Houbraken","year":"2011","journal-title":"IMA Fungus"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1021\/np200906s","article-title":"Natural products as sources of new drugs over the 30 years from 1981 to 2010","volume":"75","author":"Newman","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3670","DOI":"10.1016\/j.bbagen.2013.02.008","article-title":"Natural products: A continuing source of novel drug leads","volume":"1830","author":"Cragg","year":"2013","journal-title":"Biochim. Biophys. Acta"},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1066","DOI":"10.3390\/md12021066","article-title":"Marketed marine natural products in the pharmaceutical and cosmeceutical industries: Tips for success","volume":"12","author":"Martins","year":"2014","journal-title":"Mar. Drugs"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1038\/nrd2487","article-title":"Drug development from marine natural products","volume":"8","author":"Molinski","year":"2009","journal-title":"Nat. Rev. Drug Discov."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2257","DOI":"10.2165\/00003495-200767150-00009","article-title":"Trabectedin: A review of its use in the management of soft tissue sarcoma and ovarian cancer","volume":"67","author":"Carter","year":"2007","journal-title":"Drugs"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"573","DOI":"10.1038\/nrc3078","article-title":"Chemotaxis in cancer","volume":"11","author":"Roussos","year":"2011","journal-title":"Nat. Rev. Cancer"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1024","DOI":"10.1038\/nrm1524","article-title":"Making sense of it all: Bacterial chemotaxis","volume":"5","author":"Wadhams","year":"2004","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1146\/annurev.physiol.70.113006.100654","article-title":"Mechanisms of sperm chemotaxis","volume":"70","author":"Kaupp","year":"2008","journal-title":"Annu. Rev. Physiol."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"359","DOI":"10.1016\/j.coi.2005.06.002","article-title":"Alarmins: Chemotactic activators of immune responses","volume":"17","author":"Oppenheim","year":"2005","journal-title":"Curr. Opin. Immunol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"307","DOI":"10.1111\/1440-1681.12083","article-title":"Molecular targets in the discovery and development of novel antimetastatic agents: Current progress and future prospects","volume":"40","author":"Wong","year":"2013","journal-title":"Clin. Exp. Pharmacol. Physiol."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"91","DOI":"10.1097\/WNF.0b013e3181cbf825","article-title":"Mechanism of action of oral fingolimod (FTY720) in multiple sclerosis","volume":"33","author":"Chun","year":"2010","journal-title":"Clin. Neuropharmacol."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"900","DOI":"10.1021\/np2000528","article-title":"Fingolimod (FTY720): A recently approved multiple sclerosis drug based on a fungal secondary metabolite","volume":"74","author":"Strader","year":"2011","journal-title":"J. Nat. Prod."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"453","DOI":"10.1084\/jem.115.3.453","article-title":"The chemotactic effect of mixtures of antibody and antigen on polymorphonuclear leucocytes","volume":"115","author":"Boyden","year":"1962","journal-title":"J. Exp. Med."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"621","DOI":"10.1002\/ijc.2910190505","article-title":"Characterization of EBV-genome negative \u201cnull\u201d and \u201cT\u201d cell lines derived from children with acute lymphoblastic leukemia and leukemic transformed non-Hodgkin lymphoma","volume":"19","author":"Schneider","year":"1977","journal-title":"Int. J. Cancer"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2571","DOI":"10.3892\/or.2013.2765","article-title":"FTY720 for cancer therapy (review)","volume":"30","author":"Zhang","year":"2013","journal-title":"Oncol. Rep."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1294","DOI":"10.1111\/bph.12012","article-title":"Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels","volume":"168","author":"Qin","year":"2013","journal-title":"Br. J. Pharmacol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"461","DOI":"10.1177\/030098589803500601","article-title":"The cell cycle: A review","volume":"35","author":"Schafer","year":"1998","journal-title":"Vet. Pathol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1046\/j.1365-2184.2003.00266.x","article-title":"The cell cycle: A review of regulation, deregulation and therapeutic targets in cancer","volume":"36","author":"Vermeulen","year":"2003","journal-title":"Cell Prolif."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1535","DOI":"10.1021\/ol025759p","article-title":"Caylobolide A, a unique 36-membered macrolactone from a Bahamian Lyngbya majuscula","volume":"4","author":"MacMillan","year":"2002","journal-title":"Org. Lett."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1606","DOI":"10.1021\/np100467d","article-title":"Caylobolide B, a macrolactone from symplostatin 1-producing marine cyanobacteria Phormidium spp. from Florida","volume":"73","author":"Salvador","year":"2010","journal-title":"J. Nat. Prod."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"3327","DOI":"10.1128\/aem.63.8.3327-3332.1997","article-title":"PCR primers to amplify 16S rRNA genes from cyanobacteria","volume":"63","author":"Muyzer","year":"1997","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1095","DOI":"10.1111\/jpy.12115","article-title":"Five chemically rich species of tropical marine cyanobacteria of the genus Okeania gen. nov. (Oscillatoriales, Cyanoprokaryota)","volume":"49","author":"Engene","year":"2013","journal-title":"J. Phycol."},{"key":"ref_29","unstructured":"Chambers, K. (1997). Current Protocols in Cytometry, John Wiley & Sons."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"5418","DOI":"10.1021\/ja010453j","article-title":"Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula","volume":"123","author":"Luesch","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"934","DOI":"10.1021\/np9900324","article-title":"Madangolide and laingolide A, two novel macrolides from Lyngbya bouillonii (Cyanobacteria)","volume":"62","author":"Klein","year":"1999","journal-title":"J. Nat. Prod."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"7519","DOI":"10.1016\/0040-4039(96)01728-5","article-title":"Laingolide, a novel 15-membered macrolide from Lyngbya bouillonii (Cyanophyceae)","volume":"37","author":"Klein","year":"1996","journal-title":"Tetrahedron. Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1957","DOI":"10.1021\/acs.jnatprod.5b00293","article-title":"Amantelides A and B, polyhydroxylated macrolides with differential broad-spectrum cytotoxicity from a Guamanian marine cyanobacterium","volume":"78","author":"Sneed","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"7849","DOI":"10.1021\/acs.joc.5b01264","article-title":"Bastimolide A, a potent antimalarial polyhydroxy macrolide from the marine cyanobacterium Okeania hirsuta","volume":"80","author":"Shao","year":"2015","journal-title":"J. Org. Chem."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/13\/10\/6274\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T20:49:50Z","timestamp":1760215790000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/13\/10\/6274"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2015,10,9]]},"references-count":34,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2015,10]]}},"alternative-id":["md13106274"],"URL":"https:\/\/doi.org\/10.3390\/md13106274","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2015,10,9]]}}}