{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T06:29:50Z","timestamp":1790058590973,"version":"4.0.1"},"reference-count":58,"publisher":"MDPI AG","issue":"5","license":[{"start":{"date-parts":[[2017,4,26]],"date-time":"2017-04-26T00:00:00Z","timestamp":1493164800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Cyanobacteria are rich sources of structurally-diverse molecules with promising pharmacological activities. Marine cyanobacteria have been proven to be true producers of some significant bioactive metabolites from marine invertebrates. Macrolides are a class of bioactive compounds isolated from marine organisms, including marine microorganisms in particular. The structural characteristics of macrolides from cyanobacteria mainly manifest in the diversity of carbon skeletons, complexes of chlorinated thiazole-containing molecules and complex spatial configuration. In the present work, we systematically reviewed the structures and pharmacological activities of macrolides from cyanobacteria. Our data would help establish an effective support system for the discovery and development of cyanobacterium-derived macrolides.<\/jats:p>","DOI":"10.3390\/md15050126","type":"journal-article","created":{"date-parts":[[2017,4,26]],"date-time":"2017-04-26T13:42:06Z","timestamp":1493214126000},"page":"126","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":41,"title":["A Review Study on Macrolides Isolated from Cyanobacteria"],"prefix":"10.3390","volume":"15","author":[{"given":"Mengchuan","family":"Wang","sequence":"first","affiliation":[{"name":"School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinrong","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0196-7278","authenticated-orcid":false,"given":"Shan","family":"He","sequence":"additional","affiliation":[{"name":"School of Marine Sciences, Laboratory of Marine Natural Products, Ningbo University, Ningbo 315211, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaojun","family":"Yan","sequence":"additional","affiliation":[{"name":"Key Laboratory of Applied Marine Biotechnology of Ministry of Education, Ningbo University, Ningbo 315211, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2017,4,26]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1016\/j.jembe.2015.09.008","article-title":"Palatability and chemical defences of benthic cyanobacteria to a suite of herbivores","volume":"474","author":"Capper","year":"2016","journal-title":"J. Exp. Mar. Biol. Ecol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"954","DOI":"10.1016\/j.phytochem.2007.01.012","article-title":"Bioactive natural products from marine cyanobacteria for drug discovery","volume":"68","author":"Tan","year":"2007","journal-title":"Phytochemistry"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"122","DOI":"10.2174\/187152009787313800","article-title":"Marine macrolides, a promising source of antitumor compounds","volume":"9","author":"Napolitano","year":"2009","journal-title":"Anti-Cancer Agent Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"237","DOI":"10.3109\/13880209.2013.804100","article-title":"Marine natural products: bryostatins in preclinical and clinical studies","volume":"52","author":"Rajchard","year":"2014","journal-title":"Pharm. Biol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"2985","DOI":"10.1134\/S1070363215130174","article-title":"Polyene macrolide antibiotics: mechanisms of inactivation, ways of stabilization, and methods of disposal of unusable drugs (review)","volume":"85","author":"Belakhov","year":"2015","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"611","DOI":"10.1021\/np990543q","article-title":"Isolation, structure determination, and biological activity of lyngbyabellin A from the marine cyanobacterium Lyngbya majuscula","volume":"63","author":"Luesch","year":"2000","journal-title":"J. Nat. Prod."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"8158","DOI":"10.1002\/chem.201600674","article-title":"Discovery, total synthesis and key structural elements for the immunosuppressive activity of cocosolide, a symmetrical glycosylated macrolide dimer from marine cyanobacteria","volume":"22","author":"Gunasekera","year":"2016","journal-title":"Chem. Eur. J."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"1057","DOI":"10.1021\/np9702751","article-title":"Lyngbyaloside, a novel 2,3,4-Tri-O-methyl-6-deoxy-r-mannopyranoside macrolide from Lyngbya bouillonii (Cyanobacteria)","volume":"60","author":"Klein","year":"1997","journal-title":"J. Nat. Prod."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2207","DOI":"10.1056\/NEJMra1204479","article-title":"Two hundred years of cancer research","volume":"366","author":"DeVita","year":"2012","journal-title":"N. Engl. J. Med."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1437","DOI":"10.1021\/np000104n","article-title":"Isolation and structure of the cytotoxin lyngbyabellin B and absolute configuration of lyngbyapeptin A from the marine cyanobacterium Lyngbya majuscula","volume":"63","author":"Luesch","year":"2000","journal-title":"J. Nat. Prod."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"11723","DOI":"10.1016\/j.tet.2005.09.036","article-title":"Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula","volume":"61","author":"Han","year":"2005","journal-title":"Tetrahedron"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Choi, H., Mevers, E., Byrum, T., Valeriote, F.A., and Gerwick, W.H. (2012). Lyngbyabellins K\u2013N from Two Palmyra Atoll Collections of the marine cyanobacterium Moorea bouillonii. Eur. J. Org. Chem., 5141\u20135150.","DOI":"10.1002\/ejoc.201200691"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1945","DOI":"10.1021\/np0202879","article-title":"Lyngbyaloside B, a new glycoside macrolide from a palauan marine cyanobacterium, Lyngbya sp.","volume":"65","author":"Luesch","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1544","DOI":"10.1021\/np1004032","article-title":"Cytotoxic halogenated macrolides and modified peptides from the apratoxin-producing marine cyanobacterium Lyngbya bouillonii from Guam","volume":"73","author":"Matthew","year":"2010","journal-title":"J. Nat. Prod."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2421","DOI":"10.1021\/ol900579k","article-title":"Biselyngbyaside, a macrolide glycoside from marine cyanobacterium Lyngbya sp.","volume":"11","author":"Teruya","year":"2009","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5984","DOI":"10.1016\/j.tet.2012.05.038","article-title":"Isolation and structures of biselyngbyasides B, C, and D from the marine cyanobacterium Lyngbya sp., and the biological activities of biselyngbyasides","volume":"68","author":"Morita","year":"2012","journal-title":"Tetrahedron"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1256","DOI":"10.1246\/bcsj.20150117","article-title":"Structures and biological activities of novel biselyngbyaside analogs isolated from the marine cyanobacterium Lyngbya sp.","volume":"88","author":"Watanabe","year":"2015","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1246\/cl.2012.165","article-title":"Biselyngbyolide A, a novel cytotoxic macrolide from the marine cyanobacterium Lyngbya sp.","volume":"41","author":"Morita","year":"2012","journal-title":"Chem. Lett."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1246\/cl.130960","article-title":"Biselyngbyolide B, a novel ER stress-inducer isolated from the marine cyanobacterium Lyngbya sp.","volume":"43","author":"Ohno","year":"2014","journal-title":"Chem. Lett."},{"key":"ref_20","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_21","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_22","doi-asserted-by":"crossref","first-page":"1375","DOI":"10.1021\/ol050188x","article-title":"Isolation of swinholide A and related glycosylated derivatives from two field collections of marine cyanobacteria","volume":"7","author":"Andrianasolo","year":"2005","journal-title":"Org. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1533","DOI":"10.1021\/np50072a021","article-title":"Tolytoxin and new scytophycins from three species of Scytonema","volume":"53","author":"Carmeli","year":"1990","journal-title":"J. Nat. Prod."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"406","DOI":"10.1007\/BF00249096","article-title":"Biological effects of tolytoxin (6-hydroxy-7-O-methyl-scytophycin b), a potent bioactive metabolite from cyanobacteria","volume":"157","author":"Patterson","year":"1992","journal-title":"Arch. Microbiol."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"538","DOI":"10.1126\/science.403608","article-title":"Antileukemia activity in the Osciliatoriaceae: Isolation of debromoaplysiatoxin from Lyngbya","volume":"196","author":"Mynderse","year":"1977","journal-title":"Science"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"925","DOI":"10.1021\/np010526c","article-title":"Lyngbouilloside, a novel glycosidic macrolide from the marine cyanobacterium Lyngbya bouillonii","volume":"65","author":"Tan","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"959","DOI":"10.1016\/j.tetlet.2009.12.041","article-title":"Isolation and structure of koshikalide, a 14-membered macrolide from the marine cyanobacterium Lyngbya sp.","volume":"51","author":"Iwasaki","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3563","DOI":"10.1016\/j.tetlet.2012.04.136","article-title":"Sanctolide A, a 14-membered PK-NRP hybrid macrolide from the cultured cyanobacterium Oscillatoria sancta (SAG 74.79)","volume":"53","author":"Kang","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"8193","DOI":"10.1021\/ja00338a031","article-title":"Acutiphycin and 20,21-didehydroacutiphycin, new antineoplastic agents from the cyanophyte Oscillatoria acutissima","volume":"106","author":"Barchi","year":"1984","journal-title":"J. Am. Chem. Soc."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1021\/acs.estlett.5b00116","article-title":"Isolation of polycavernoside D from a marine cyanobacterium","volume":"2","author":"Navarro","year":"2015","journal-title":"Environ. Sci. Technol. Lett."},{"key":"ref_31","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 hirsute","volume":"80","author":"Shao","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"6274","DOI":"10.3390\/md13106274","article-title":"Macrolactone nuiapolide, isolated from a Hawaiian marine cyanobacterium, exhibits anti-chemotactic activity","volume":"13","author":"Mori","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"6815","DOI":"10.1002\/chem.201600341","article-title":"total synthesis and complete stereostructure of a marine macrolide glycoside, (-)-lyngbyaloside B","volume":"22","author":"Fuwa","year":"2016","journal-title":"Chem. Eur. J."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"10681","DOI":"10.1002\/chem.201502132","article-title":"Total synthesis and structural reassignment of lyngbyaloside C highlighted by intermolecular ketene esterification","volume":"21","author":"Chang","year":"2015","journal-title":"Chem. Eur. J."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"252","DOI":"10.1016\/j.tetlet.2012.11.015","article-title":"Enantioselective synthesis of the C5\u2013C23 segment of biselyngbyaside","volume":"54","author":"Chandrasekhar","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1164","DOI":"10.1016\/j.tetlet.2013.12.091","article-title":"Studies directed toward the synthesis of caylobolide A: convergent synthesis of C21\u2013C40 subunit","volume":"55","author":"Yadav","year":"2014","journal-title":"Tetrahedron Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5300","DOI":"10.1021\/jo00376a047","article-title":"Scytophycins, cytotoxic and antimycotic agents from the cyanophyte Scytonema pseudohofmanni","volume":"51","author":"Ishibashi","year":"1986","journal-title":"J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"446","DOI":"10.1016\/j.tetlet.2015.12.051","article-title":"Catalytic asymmetric synthesis of key intermediate for scytophycin C","volume":"57","author":"Cui","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"ref_39","first-page":"1","article-title":"Constituents of blue-green algae","volume":"Volume 4","author":"Scheuer","year":"1981","journal-title":"Marine Natural Products"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1333","DOI":"10.1001\/archderm.1978.01640210028007","article-title":"Dermatitis from purified sea algae toxin (debromoaplysiatoxin)","volume":"114","author":"Solomon","year":"1978","journal-title":"Arch. Dermatol."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"2301","DOI":"10.1021\/jo00405a053","article-title":"Toxins from Blue-Green algae: Structures ofoscillatoxin A and three related bromine-containing toxins","volume":"43","author":"Mynderse","year":"1978","journal-title":"J. Org. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3121","DOI":"10.1016\/j.tetlet.2016.06.002","article-title":"Total synthesis and absolute configuration of koshikalide","volume":"57","author":"Kunifuda","year":"2016","journal-title":"Tetrahedron Lett."},{"key":"ref_43","doi-asserted-by":"crossref","unstructured":"Yadav, J.S., Suresh, B., and Srihari, P. (2015). Stereoselective total synthesis of the marine macrolide sanctolide A. Eur. J. Org. Chem., 5856\u20135863.","DOI":"10.1002\/ejoc.201500677"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"1179","DOI":"10.4155\/cli.13.109","article-title":"Macrolide therapy in cystic fibrosis: New developments in clinical use","volume":"3","author":"Frayman","year":"2013","journal-title":"Clin. Investig."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2124","DOI":"10.3390\/md13042124","article-title":"Antifungal compounds from cyanobacteria","volume":"13","author":"Shishido","year":"2015","journal-title":"Mar. Drugs"},{"key":"ref_46","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_47","doi-asserted-by":"crossref","first-page":"276","DOI":"10.1016\/j.envint.2016.02.026","article-title":"Acute animal and human poisonings from cyanotoxin exposure\u2014A review of the literature","volume":"9","author":"Wood","year":"2016","journal-title":"Environ. Int."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"251","DOI":"10.1021\/np9703398","article-title":"Gloeolactone, a new epoxy lactone from a blue-green alga","volume":"61","author":"Stierle","year":"1998","journal-title":"J. Nat. Prod."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"7927","DOI":"10.1021\/jo020240s","article-title":"Structure and absolute stereochemistry of phormidolide, a new toxic metabolite from the marine cyanobacterium phormidium sp.","volume":"67","author":"Williamson","year":"2002","journal-title":"J. Org. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"217","DOI":"10.1021\/np9008128","article-title":"Cyanolide A, a glycosidic macrolide with potent molluscicidal activity from the Papua New Guinea cyanobacterium Lyngbya bouillonii","volume":"73","author":"Pereira","year":"2010","journal-title":"J. Nat. Prod."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1731","DOI":"10.1055\/s-0033-1341153","article-title":"A synthesis of cyanolide A by intramolecular oxa-michael addition","volume":"46","author":"Bates","year":"2014","journal-title":"Synthesis"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"440","DOI":"10.1002\/jcb.23213","article-title":"Biselyngbyaside, isolated from marine cyanobacteria, inhibits osteoclastogenesis and induces apoptosis in mature osteoclasts","volume":"113","author":"Yonezawa","year":"2012","journal-title":"J. Cell. Biochem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"709","DOI":"10.1021\/np9005184","article-title":"Malyngolide Dimer, a bioactive symmetric cyclodepside from the panamanian marine cyanobacterium Lyngbya majuscula","volume":"73","author":"Tidgewell","year":"2010","journal-title":"J. Nat. Prod."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"5267","DOI":"10.1021\/jo900578j","article-title":"Structural and synthetic investigations of tanikolide dimer, a SIRT2 selective inhibitor, and tanikolideseco-acid from the Madagascar marine cyanobacterium Lyngbya majuscula","volume":"74","author":"Gutierrez","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"4490","DOI":"10.1021\/ol101752n","article-title":"Palmyrolide A, an Unusually Stabilized Neuroactive Macrolide from Palmyra Atoll Cyanobacteria","volume":"12","author":"Pereira","year":"2010","journal-title":"Org. Lett."},{"key":"ref_56","first-page":"4490","article-title":"Total synthesis of palmyrolide A and its 5,7-epi isomers","volume":"12","author":"Sudhakar","year":"2010","journal-title":"Org. Lett."},{"key":"ref_57","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_58","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."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/15\/5\/126\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:33:53Z","timestamp":1760207633000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/15\/5\/126"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,4,26]]},"references-count":58,"journal-issue":{"issue":"5","published-online":{"date-parts":[[2017,5]]}},"alternative-id":["md15050126"],"URL":"https:\/\/doi.org\/10.3390\/md15050126","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,4,26]]}}}