Abstract
In this review, we summarize the diverse marine natural compounds obtained from the genus Verrucella and their pharmacological effects and present a survey of the natural products taxonomy according to species. Sixty-six natural substances, including fifty-three steroids, six briarane-type diterpenoids, five nitrogenous bases, one amide, and one glycerol derivative, were obtained from Verrucella spp., which were mainly collected from the South China Sea and the Bay of Bengal, India. Steroids were the major constituents found in Verrucella spp. Moreover, anticancer, antimicrobial, and immunomodulatory activities of those steroids and other compounds are also presented. This review reveals the chemical diversity, chemotaxonomy, and multiple pharmacological effects of the Verrucella genus. It will be helpful for further research and exploration of new steroid analogs and other components with prospective biological activities from this marine organism.
Keywords: Verrucella, steroid, briarane, nitrogenous base, amide, glycerol, cytotoxicity.
Graphical Abstract
[http://dx.doi.org/10.1021/np960576v] [PMID: 9748378]
[http://dx.doi.org/10.1016/S0040-4020(00)00372-0]
[http://dx.doi.org/10.1016/j.steroids.2018.06.006] [PMID: 30018002]
[http://dx.doi.org/10.15625/2525-2518/56/4A/12754]
[http://dx.doi.org/10.1002/cjoc.200591218]
[http://dx.doi.org/10.1002/hlca.200490299]
[http://dx.doi.org/10.1016/0039-128X(90)90010-9] [PMID: 2281509]
[http://dx.doi.org/10.1016/j.tet.2011.05.091]
[http://dx.doi.org/10.1021/np50068a034]
[http://dx.doi.org/10.1021/np50072a003]
[http://dx.doi.org/10.1039/jr9540001356]
[http://dx.doi.org/10.1021/np50042a010]
[http://dx.doi.org/10.1021/np50053a024]
[http://dx.doi.org/10.1021/np50089a005]
[http://dx.doi.org/10.1021/np50092a016]
[http://dx.doi.org/10.1016/j.bse.2014.06.010]
[http://dx.doi.org/10.4103/0973-1296.80663] [PMID: 21716930]
[http://dx.doi.org/10.1016/0031-9422(75)85354-4]
[http://dx.doi.org/10.1248/cpb.24.3214]
[http://dx.doi.org/10.1139/v85-398]
[http://dx.doi.org/10.1080/10286020.2014.924511] [PMID: 24911542]
[http://dx.doi.org/10.1016/S0040-4020(01)93577-X]
[http://dx.doi.org/10.1515/znb-2005-1114]
[http://dx.doi.org/10.1016/S0040-4020(01)80026-0]
[http://dx.doi.org/10.1021/np980331d] [PMID: 10075754]
[http://dx.doi.org/10.1248/cpb.51.1429] [PMID: 14646324]
[http://dx.doi.org/10.1016/S0305-1978(03)00173-X]
[http://dx.doi.org/10.1021/np049848h] [PMID: 15568788]
[http://dx.doi.org/10.1248/cpb.52.1476] [PMID: 15577249]
[http://dx.doi.org/10.1002/hlca.200590170]
[http://dx.doi.org/10.1246/bcsj.79.634]
[http://dx.doi.org/10.1177/1934578X0700200204]
[http://dx.doi.org/10.1016/j.bse.2007.06.003]
[http://dx.doi.org/10.1021/np800126f] [PMID: 18774864]
[http://dx.doi.org/10.1016/j.tet.2012.10.102]
[http://dx.doi.org/10.3390/md12020589] [PMID: 24473165]
[PMID: 25095349]
[http://dx.doi.org/10.3987/COM-19-14109]
[http://dx.doi.org/10.3390/md17120706] [PMID: 31847481]
[PMID: 2874610]
[http://dx.doi.org/10.3390/molecules23071510] [PMID: 29932137]
[http://dx.doi.org/10.1016/j.tet.2007.05.042]
[http://dx.doi.org/10.3184/030823400103166878]
[http://dx.doi.org/10.1080/14786410310000104091] [PMID: 12737396]
[http://dx.doi.org/10.1016/S0040-4020(01)98730-7]
[http://dx.doi.org/10.1016/S0040-4020(01)97391-0]
[http://dx.doi.org/10.1016/0039-128X(80)90070-7] [PMID: 7414658]
[http://dx.doi.org/10.1021/jo00332a020]
[http://dx.doi.org/10.1016/j.steroids.2008.09.007] [PMID: 18851985]
[http://dx.doi.org/10.1021/np50065a007]
[http://dx.doi.org/10.1039/a604271f]
[http://dx.doi.org/10.1111/j.1365-2672.2005.02760.x] [PMID: 16405700]
[http://dx.doi.org/10.1016/j.bse.2010.11.001]
[http://dx.doi.org/10.1002/bscb.19860950910]
[http://dx.doi.org/10.1021/jo00373a020]
[http://dx.doi.org/10.1021/ja00329a077]
[http://dx.doi.org/10.1002/hlca.200790141]
[http://dx.doi.org/10.1007/s10600-012-0295-0]
[http://dx.doi.org/10.1515/znc-1974-9-1004] [PMID: 4278369]
[http://dx.doi.org/10.1021/np50054a040] [PMID: 2895166]
[http://dx.doi.org/10.3390/md10051180] [PMID: 22822365]
[http://dx.doi.org/10.1515/znc-1977-11-1202]
[http://dx.doi.org/10.1080/14786419.2012.688047] [PMID: 22594605]
[http://dx.doi.org/10.1016/S0039-128X(01)00122-2] [PMID: 11711118]
[http://dx.doi.org/10.1248/cpb.24.3109] [PMID: 1022352]
[http://dx.doi.org/10.1016/0039-128X(81)90069-6] [PMID: 6117956]
[http://dx.doi.org/10.1016/j.steroids.2009.04.011] [PMID: 19427327]
[http://dx.doi.org/10.1021/np070069l] [PMID: 17604394]
[http://dx.doi.org/10.1002/hlca.201300397]
[http://dx.doi.org/10.1021/acs.jnatprod.1c00200] [PMID: 33966392]
[http://dx.doi.org/10.1016/j.steroids.2014.12.001] [PMID: 25528195]
[http://dx.doi.org/10.1246/cl.1991.427]
[http://dx.doi.org/10.1021/np50122a024] [PMID: 7595595]
[http://dx.doi.org/10.1021/np980220e] [PMID: 9834177]
[http://dx.doi.org/10.1016/j.bmc.2011.09.028] [PMID: 21982797]
[http://dx.doi.org/10.1016/S0040-4039(01)93428-8]
[http://dx.doi.org/10.1021/np058077u] [PMID: 16499329]
[http://dx.doi.org/10.1002/ejoc.200300214]
[http://dx.doi.org/10.3987/REV-19-925]
[http://dx.doi.org/10.3390/md16090339] [PMID: 30227646]
[http://dx.doi.org/10.1007/s11274-013-1279-3] [PMID: 23386321]