Abstract
Marine invertebrates, especially tunicates, are a lucrative resource for the discovery of new lead compounds for the development of clinically utilized drugs. This review describes the isolation, synthesis and biological activities of several classes of marine-derived butenolide natural products, namely rubrolides and related cadiolides and prunolides. All relevant studies pertaining to these compounds up to the end of 2019 are included.
Keywords: Marine natural products, rubrolides, cadiolides, prunolides, antibiotics, synthesis.
[http://dx.doi.org/10.2307/1312834]
[http://dx.doi.org/10.1038/nature04336] [PMID: 16495997]
[http://dx.doi.org/10.1007/BF01319409]
[http://dx.doi.org/10.3390/md12020719] [PMID: 24473171]
[http://dx.doi.org/10.1007/s13659-016-0115-5] [PMID: 28097641]
[http://dx.doi.org/10.1021/ja00317a080]
[http://dx.doi.org/10.1021/ja00317a079]
[http://dx.doi.org/10.1021/acs.jnatprod.9b00493] [PMID: 31306000]
[http://dx.doi.org/10.1021/ja00305a027]
[http://dx.doi.org/10.1021/jo00301a040]
[http://dx.doi.org/10.1016/S0040-4039(00)73283-7]
[http://dx.doi.org/10.1038/ja.2013.135] [PMID: 24326339]
[http://dx.doi.org/10.1021/jo00022a012]
[http://dx.doi.org/10.1021/ja00006a060]
[http://dx.doi.org/10.1021/jo980171a]
[http://dx.doi.org/10.1021/np300544a] [PMID: 23145884]
[http://dx.doi.org/10.1021/jo981881j] [PMID: 11674336]
[http://dx.doi.org/10.1016/S0040-4020(00)00328-8]
[http://dx.doi.org/10.1016/S0040-4020(01)01017-1]
[http://dx.doi.org/10.1021/np060188l] [PMID: 17253860]
[http://dx.doi.org/10.1021/np300580z] [PMID: 23030848]
[http://dx.doi.org/10.1080/14786419.2013.827194] [PMID: 23962161]
[http://dx.doi.org/10.1007/s10600-016-1719-z]
[http://dx.doi.org/10.1016/j.tet.2017.11.039]
[http://dx.doi.org/10.1021/np3005562] [PMID: 23145909]
[http://dx.doi.org/10.1016/j.bmcl.2013.05.051] [PMID: 23747224]
[http://dx.doi.org/10.1016/j.bmcl.2016.12.016] [PMID: 28043797]
[http://dx.doi.org/10.1021/acs.jnatprod.9b00551] [PMID: 31436981]
[http://dx.doi.org/10.1248/cpb.25.2593]
[http://dx.doi.org/10.2174/1385272821666170111151917]
[http://dx.doi.org/10.1590/S0100-40422011000800023]
[http://dx.doi.org/10.2174/1385272043370195]
[http://dx.doi.org/10.1055/s-1997-1513]
[http://dx.doi.org/10.1039/a900286c]
[http://dx.doi.org/10.1016/S0040-4039(98)01715-8]
[http://dx.doi.org/10.1016/S0040-4039(02)00202-2]
[http://dx.doi.org/10.1002/ejoc.200300097]
[http://dx.doi.org/10.1002/ejoc.201600473]
[http://dx.doi.org/10.1016/j.tetlet.2010.06.129]
[http://dx.doi.org/10.1021/np0503698] [PMID: 17067167]
[http://dx.doi.org/10.1021/jf302921n] [PMID: 23025464]
[http://dx.doi.org/10.1016/j.jphotobiol.2015.02.016] [PMID: 25748644]
[http://dx.doi.org/10.1016/j.electacta.2013.12.053]
[http://dx.doi.org/10.1002/cbdv.201400416] [PMID: 26172321]
[http://dx.doi.org/10.1016/j.bmcl.2014.01.023] [PMID: 24484899]
[http://dx.doi.org/10.1016/j.ejmech.2014.05.035] [PMID: 24880232]
[http://dx.doi.org/10.1021/acsomega.8b02334]
[http://dx.doi.org/10.1039/C5MD00459D]
[http://dx.doi.org/10.1016/S0040-4020(01)81808-1]
[http://dx.doi.org/10.1007/s10126-018-9861-1] [PMID: 30612218]
[http://dx.doi.org/10.1016/j.tetlet.2017.06.016]
[http://dx.doi.org/10.1080/00397910701575665]
[http://dx.doi.org/10.1055/s-0028-1088132]
[http://dx.doi.org/10.1002/hlca.201100351]
[http://dx.doi.org/10.1016/j.tetlet.2016.11.096]
[http://dx.doi.org/10.1002/ejoc.201501151]
[http://dx.doi.org/10.1002/ejoc.201700158]
[http://dx.doi.org/10.1016/j.tetlet.2019.151307]
[http://dx.doi.org/10.1016/j.tet.2006.01.110]
[http://dx.doi.org/10.1021/ar800023v] [PMID: 18605738]
[http://dx.doi.org/10.1021/ol050619b] [PMID: 15932197]
[http://dx.doi.org/10.1007/s00044-018-2246-1]
[http://dx.doi.org/10.1055/s-2004-837220]
[http://dx.doi.org/10.1021/jo502503w] [PMID: 25423410]
[http://dx.doi.org/10.21577/0100-4042.20170368]
[http://dx.doi.org/10.1002/ejoc.201300166]
[http://dx.doi.org/10.1016/j.bmc.2015.04.010] [PMID: 25913865]