{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,18]],"date-time":"2026-10-18T02:32:12Z","timestamp":1792290732302,"version":"4.4.0"},"reference-count":69,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2020,2,13]],"date-time":"2020-02-13T00:00:00Z","timestamp":1581552000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Invertebrates are an important source of structurally-diverse and biologically-active halogenated metabolites. The sea hare Aplysia dactylomela Rang has long been known to possess halogenated metabolites of dietary origin that are used as a self-defense mechanism. The compounds from Aplysia dactylomela Rang are comprised mainly of terpenoids and small percentages of C-15 acetogenins, indoles, macrolides, sterols and alkaloids with potent cytotoxic, anti-microbial and anti-inflammatory properties. For decades the metabolites discovered have been investigated for their medical and pharmaceutical applications, so much so that the ecological role of the metabolites has been overlooked. The interaction between Aplysia dactylomela Rang and its diet that is comprised of seaweed can provide information into the distribution and diversity of the seaweed, the application of bioaccumulated secondary metabolites as part of its defense mechanism and the potential roles of these metabolites for adaptation in the marine environment. This paper compiles the diversity of halogenated secondary metabolites documented from Aplysia dactylomela Rang.<\/jats:p>","DOI":"10.3390\/molecules25040815","type":"journal-article","created":{"date-parts":[[2020,2,26]],"date-time":"2020-02-26T05:44:12Z","timestamp":1582695852000},"page":"815","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Halogenated Metabolites from the Diet of Aplysia dactylomela Rang"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0466-2602","authenticated-orcid":false,"given":"Kishneth","family":"Palaniveloo","sequence":"first","affiliation":[{"name":"Institute of Ocean and Earth Sciences, Institute for Advanced Studies Building, University of Malaya, Wilayah Persekutuan Kuala Lumpur 50603, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mohammed","family":"Rizman-Idid","sequence":"additional","affiliation":[{"name":"Institute of Ocean and Earth Sciences, Institute for Advanced Studies Building, University of Malaya, Wilayah Persekutuan Kuala Lumpur 50603, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thilahgavani","family":"Nagappan","sequence":"additional","affiliation":[{"name":"School of Marine and Environmental Sciences, Universiti Malaysia Terengganu, Kuala Terengganu 21030, Terengganu, Malaysia"},{"name":"Institute of Marine Biotechnology, Universiti Malaysia Terengganu, Kuala Terengganu 21030, Terengganu, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shariza","family":"Abdul Razak","sequence":"additional","affiliation":[{"name":"Nutrition and Dietetics Program, School of Health Sciences, Health Campus, Universiti Sains Malaysia, Kubang Kerian 16150, Kelantan, Malaysia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,2,13]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"1911","DOI":"10.1021\/cr00021a012","article-title":"Marine invertebrate chemical defences","volume":"93","author":"Pawlik","year":"1993","journal-title":"Chem. Rev."},{"key":"ref_2","first-page":"12","article-title":"Chemistry and chemical ecology of some of the common opistobranch molluscs found on the shores of the NE New Zealand","volume":"69","author":"Grkovic","year":"2005","journal-title":"Chem. N. Z."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"135","DOI":"10.3354\/meps130135","article-title":"Quantitative variation of secondary metabolites in the sea hare Aplysia parvula and its host plant, Delisea pulchra","volume":"130","author":"Steinberg","year":"1996","journal-title":"Mar. Ecol. Progress Ser."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"261","DOI":"10.3354\/meps215261","article-title":"Chemical defences in the sea hare Aplysia parvula: Importance of diet and sequestration of algal secondary metabolites","volume":"215","author":"Ginsburg","year":"2001","journal-title":"Mar. Ecol. Progress Ser."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"531","DOI":"10.1007\/BF02784281","article-title":"New trends in marine chemical ecology","volume":"29","author":"Ianora","year":"2006","journal-title":"Estuaries Coasts"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1039\/C6NP00097E","article-title":"Chemical mediation as a structuring element in marine gastropod predator-prey interactions","volume":"34","author":"Bornancin","year":"2017","journal-title":"Nat. Prod. Rep."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1016\/j.anbehav.2010.04.003","article-title":"The purple pigment aplysioviolin in sea hare ink deters predatory blue crabs through their chemical senses","volume":"80","author":"Kamio","year":"2010","journal-title":"Anim. Behav."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/S0022-0981(96)02659-7","article-title":"Marine chemical ecology: What\u2019s known and what\u2019s next?","volume":"200","author":"Hay","year":"1996","journal-title":"J. Exp. Biol. Ecol."},{"key":"ref_9","first-page":"17","article-title":"Halogenated secondary metabolites from sea hare Aplysia Dactylomela","volume":"24","author":"Vairappan","year":"2005","journal-title":"Malays. J. Sci."},{"key":"ref_10","first-page":"57","article-title":"Additional halogenated secondary metabolites from the sea hare Aplysia dactylomela","volume":"26","author":"Vairappan","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"269","DOI":"10.22452\/mjs.vol28no3.5","article-title":"Diet-derived halogenated metabolite from the sea hare Aplysia parvula","volume":"28","author":"Vairappan","year":"2009","journal-title":"Malays. J. Sci."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"9970","DOI":"10.1016\/j.tet.2007.07.055","article-title":"Aplysiols A and B, squalene-derived polyethers from the mantle of the sea hare Aplysia dactylomela","volume":"63","author":"Manzo","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_13","first-page":"329","article-title":"Natural halogenated non-terpenic C15-acetogenins of sea organisms","volume":"11","author":"Dembitsky","year":"2003","journal-title":"Chem. Sustain. Dev."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"920","DOI":"10.1021\/np9905721","article-title":"New natural product isolation and comparison of the secondary metabolite content of three distinct samples of the sea hare Aplysia dactylomela from Tenerife","volume":"63","author":"Wessels","year":"2000","journal-title":"J. Natural Prod."},{"key":"ref_15","first-page":"487","article-title":"Natural products of opisthobranch molluscs: A biological review","volume":"33","author":"Avila","year":"1995","journal-title":"Oceanogr. Mar. Biol. Annu. Rev."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Pereira, R.B., Andrade, P.B., and Valentao, P. (2016). Chemical diversity and biological properties of secondary metabolites from sea hares of Aplysia genus. Mar. Drugs, 14.","DOI":"10.3390\/md14020039"},{"key":"ref_17","first-page":"1199","article-title":"Chemical relationship between red algae genus Laurencia and sea hare (Aplysia dactylomela Rang) in the North Borneo Island","volume":"26","author":"Palaniveloo","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"171","DOI":"10.3354\/meps150171","article-title":"Chemical ecology of the nudibranch Glossodoris pallida: Is the location of diet-derived metabolites important for defense?","volume":"150","author":"Conxita","year":"1997","journal-title":"Mar. Ecol. Progress Ser."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2301","DOI":"10.3390\/md8082301","article-title":"Halogenated compounds form Marine Algae","volume":"8","author":"Cabrita","year":"2010","journal-title":"Mar. Drugs"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"483","DOI":"10.1016\/j.biotechadv.2011.05.016","article-title":"Algal chemodiversity and bioactivity: Sources of natural variability and implications for commercial application","volume":"29","author":"Stengel","year":"2011","journal-title":"Biotechnol. Adv."},{"key":"ref_21","first-page":"3670","article-title":"Natural Products: A continuing source of novel drug leads","volume":"1830","author":"Cragg","year":"2013","journal-title":"Mar. Ecol. Program Ser."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"1","DOI":"10.3354\/meps323001","article-title":"Seaweed\u2013herbivore interactions at a small scale: Direct tests of feeding deterrence by filamentous algae","volume":"323","author":"Paul","year":"2006","journal-title":"Mar. Ecol. Program Ser."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Perveen, S., and Al-Taweel, A. (2018). Introductory Chapter: Terpenes and Terpenoids. Terpenes and Terpenoids, IntechOpen.","DOI":"10.5772\/intechopen.79683"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1007\/s13205-014-0220-2","article-title":"Plant terpenes: Defense responses, phylogenetic analysis, regulation and clinical applications","volume":"5","author":"Singh","year":"2015","journal-title":"3 Biotech"},{"key":"ref_25","first-page":"15060","article-title":"Vanadium bromoperoxidase-catalysed biosynthesis of halogenated marine natural products","volume":"26","author":"Butler","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"43436","DOI":"10.1038\/srep43436","article-title":"Hydrogen peroxide in deep waters from the Mediterranean Sea, South Atlantic and South Pacific Oceans","volume":"7","author":"Hopwood","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1039\/b302337k","article-title":"The role of vanadium bromoperoxidase in the biosynthesis of halogenated marine natural products","volume":"21","author":"Butler","year":"2004","journal-title":"Nat. Prod. Rep."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"721","DOI":"10.1023\/A:1005484306931","article-title":"Dynamics of algal secondary metabolites in two species of sea hare","volume":"26","author":"Rogers","year":"2000","journal-title":"J. Chem. Ecol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.chembiol.2008.01.006","article-title":"Halogenation Strategies In Natural Product Biosynthesis","volume":"15","author":"Neumann","year":"2008","journal-title":"Chem. Biol."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"1441","DOI":"10.1021\/ed081p1441","article-title":"Natural Organohalogens:A New Frontier for Medicinal Agents?","volume":"81","author":"Gribble","year":"2004","journal-title":"J. Chem. Educ."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"170","DOI":"10.1039\/b805113p","article-title":"Marine Natural Products","volume":"26","author":"Blunt","year":"2010","journal-title":"Nat. Prod. Rep."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"3368","DOI":"10.1021\/acs.joc.7b00188","article-title":"High-Throughput in Silico Structure Validation and Revision of Halogenated Natural Products Is Enabled by Parametric Corrections to DFT-Computed 13C NMR Chemical Shifts and Spin Spin Coupling Constants","volume":"82","author":"Kutateladze","year":"2017","journal-title":"J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1963","DOI":"10.1016\/0040-4020(75)87060-8","article-title":"Polyhalogenated monoterpenes from the red alga Plocamium cartilagineum","volume":"31","author":"Mynderse","year":"1975","journal-title":"Tetrahedron"},{"key":"ref_34","first-page":"1","article-title":"Phytochemical and Biological Properties of Sesquiterpene Constituents From the Marine Red Seaweed Laurencia: A Review?","volume":"2","year":"2014","journal-title":"Nat. Prod. Chem. Res."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1485","DOI":"10.1016\/S0040-4020(01)99222-1","article-title":"Structures of aplysin and aplysinol, naturally occurring bromo-compound","volume":"19","author":"Yamamura","year":"1963","journal-title":"Tetrahedron"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1837","DOI":"10.1016\/S0040-4039(00)90267-3","article-title":"Laurinterol and debromolaurinterol, constituents from Laurencia intermedia","volume":"7","author":"Irie","year":"1966","journal-title":"Tetrahedron Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"843","DOI":"10.1246\/bcsj.42.843","article-title":"Isolation of aplysin, debromoaplysin and aplysinol from Laurencia okamurai Yamada","volume":"42","author":"Irie","year":"1969","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1618","DOI":"10.1021\/np990229w","article-title":"New halogenated sesquiterpenes from South African specimens of the circumtropical sea hare Aplysia dactylomela","volume":"62","author":"McPhail","year":"1999","journal-title":"J. Nat. Prod."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"10181","DOI":"10.1016\/S0040-4020(01)01044-4","article-title":"Novel tryptophan-derived and bioactive metabolites from the sea hare Aplysia dactylomela","volume":"57","author":"Appleton","year":"2001","journal-title":"Tetrahedron"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1951","DOI":"10.1016\/S0031-9422(00)84948-1","article-title":"Sesquiterpenes from the marine red alga Laurencia distichophylla","volume":"23","author":"Blunt","year":"1984","journal-title":"Phytochemistry"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3364","DOI":"10.1021\/jo00367a021","article-title":"New cuparene-derived sesquiterpenes with unprecedented oxygenation patterns from the sea hare Aplysia dactylomela","volume":"51","author":"Ichiba","year":"1986","journal-title":"J. Organ. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1016\/0040-4020(79)80153-2","article-title":"Marine natural products: Deodactol, antineoplastic sesquiterpenoid from the sea hare Aplysia dactylomela","volume":"35","author":"Hollenbaek","year":"1979","journal-title":"Tetrahedron"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1016\/S0040-4039(00)71409-2","article-title":"Total synthesis of 8-desoxy-isocaespitol, a new polyhalogenated sesquiterpene from Laurencia caespitosa","volume":"21","author":"Gonzalez","year":"1980","journal-title":"Tetrahedron Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"5192","DOI":"10.1021\/jo00338a026","article-title":"Marine natural products: Halogenated acetylenic ethers from the sea hare Aplysia dactylomela","volume":"46","author":"Gopichand","year":"1981","journal-title":"J. Organ. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"9655","DOI":"10.1016\/j.tet.2006.07.078","article-title":"Aplysiadiol from Aplysia dactylomela suggested a key intermediate for a unified biogenesis of regular and irregular marine algal bisabolene-type metabolites","volume":"62","author":"Brito","year":"2006","journal-title":"Tetrahedron"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1619","DOI":"10.1021\/np50072a042","article-title":"Aplysiadiol, a new brominated diterpene from the marine mollusc Aplysia kurodai","volume":"53","author":"Ojika","year":"1990","journal-title":"J. Nat. Prod."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"262","DOI":"10.1021\/ja00443a055","article-title":"Antineoplastic agents. 48. The isolation and structure of Aplysistatin","volume":"99","author":"Pettit","year":"1976","journal-title":"J. Am. Chem. Soc."},{"key":"ref_48","first-page":"1069","article-title":"Total synthesis of (+)-Palisadin A and (+)-12-hydroxypalisadin B","volume":"50","author":"Tanaka","year":"1986","journal-title":"Agric. Biol. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2787","DOI":"10.1016\/S0040-4039(00)78607-2","article-title":"Palisadin A, B, and related monocyclofarnesol derived sesquiterpenoids from the red marine alga Laurencia cf palisada","volume":"21","author":"Paul","year":"1980","journal-title":"Tetrahedron Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1351\/pac198153040853","article-title":"Recent developments in research on metabolites from Caribbean marine invertebrates","volume":"53","author":"Schmitz","year":"1981","journal-title":"Pure Appl. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1677","DOI":"10.1021\/np050240y","article-title":"Cytotoxic sesquiterpenes from Aplysia dactylomela","volume":"68","author":"Dias","year":"2005","journal-title":"J. Nat. Prod."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1246\/bcsj.72.289","article-title":"Fourteen chamigrane derivatives from a red alga, Laurencia nidifica","volume":"72","author":"Kimura","year":"1999","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1002\/mrc.800","article-title":"Complete 1H and 13C NMR assignments of chamigranes from Aplysia dactylomela","volume":"39","author":"Kaiser","year":"2001","journal-title":"Magn. Resonance Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"2109","DOI":"10.1007\/s11172-007-0329-0","article-title":"Four new chamigrane sesquiterpenoids from the opistobranch mollusk Aplysia dactylomela","volume":"56","author":"Shubina","year":"2007","journal-title":"Rus. Chem. Bull."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"1022","DOI":"10.1023\/A:1024489418232","article-title":"Chemical properties of marine terpenoids. 1. Some reactions of (6S,10R)-10-bromo-3,11,11-trimethyl-7-methylidenespiro[5,5]undec-2-en-4-one, a sesquiterpenoid from the sea hare Aplysia dactylomela","volume":"52","author":"Lyakhova","year":"2003","journal-title":"Rus. Chem. Bull."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"677","DOI":"10.1007\/BF01014710","article-title":"Aplysia sea hare assimilation of secondary metabolites from brown seaweed, Stypopodium zonale","volume":"15","author":"Gerwick","year":"1989","journal-title":"J. Chem. Ecol."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1979","DOI":"10.1016\/S0040-4039(00)00077-0","article-title":"Structure and absolute configuration of the new rearranged chamigrane-type sesquiterpenoid from the sea hare Aplysia sp.","volume":"41","author":"Fedorov","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"5914","DOI":"10.1158\/0008-5472.CAN-06-3723","article-title":"Dactylone inhibits Epidermal Growth Factor\u2013induced transformation and phenotype expression of human cancer cells and induces G1-S arrest and apoptosis","volume":"67","author":"Fedorov","year":"2007","journal-title":"Cancer Res."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"504","DOI":"10.1021\/ja003254t","article-title":"Aplydactone, a new sesquiterpenoid with an unprecedented carbon skeleton from the sea hare Aplysia dactylomela, and its cargill-like rearrangement","volume":"123","author":"Fedorov","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1021\/acscentsci.6b00293","article-title":"Unravelling photochemical relationships among natural products from Aplysia dactylomela","volume":"3","author":"Matsuura","year":"2017","journal-title":"ACS Cent. Sci."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1021\/np200845f","article-title":"Dactylomelatriol, a biogenetically intriguing omphalane-derived marine sesquiterpene","volume":"75","author":"Brito","year":"2012","journal-title":"J. Nat. Prod."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"569","DOI":"10.1016\/j.bjp.2015.07.027","article-title":"C15 acetogenins from the Laurencia complex: 50 years of research\u2014An overview","volume":"25","author":"Wanke","year":"2015","journal-title":"Rev. Bras. Farmacogn."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3480","DOI":"10.1021\/jo00883a037","article-title":"Marine natural products: Isodactylyne, a halogenated acetylenic ether from the sea hare Aplysia dactylomela","volume":"41","author":"Vanderah","year":"1976","journal-title":"J. Organ. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"17343","DOI":"10.1016\/S0040-4020(97)10158-2","article-title":"Dactylallene: A novel dietary C15 bromoallene from the Atlantic anaspidean mollusk Aplysia dactylomela","volume":"53","author":"Ciavatta","year":"1997","journal-title":"Tetrahedron"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"7456","DOI":"10.1016\/j.tet.2005.05.051","article-title":"Structure and absolute stereochemistry of novel C15-halogenated acetogenins from the anaspidean mollusk Aplysia dactylomela","volume":"61","author":"Manzo","year":"2005","journal-title":"Tetrahedron"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"6415","DOI":"10.1021\/ja00387a045","article-title":"Marine natural products: Parguerol, deoxyparguerol, and isoparguerol. New brominated diterpenes with modified pimarane skeletons from the sea hare Aplysia dactylomela","volume":"104","author":"Schmitz","year":"1982","journal-title":"J. Am. Chem. Soc."},{"key":"ref_67","unstructured":"Se-Kwon, K. (2018). P-gp inhibitory activity from marine sponges, tunicates and algae. Handbook of Anticancer Drugs from Marine Origin, Springer."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2445","DOI":"10.1021\/jo01328a024","article-title":"Marine natural products: 14-bromoobtus-1-ene-3,11-diol, a new diterpenoid from the sea hare Aplysia dactylomela","volume":"44","author":"Schmitz","year":"1979","journal-title":"J. Organ. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"5327","DOI":"10.1002\/ejoc.200900775","article-title":"Aplysqualenols A and B: Squalene-derived polyethers with antitumoral and antiviral activity from the Carribean sea slug Aplysia dactylomela","volume":"31","author":"Vera","year":"2009","journal-title":"Eur. J. Organ. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/4\/815\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T08:57:36Z","timestamp":1760173056000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/4\/815"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,2,13]]},"references-count":69,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2020,2]]}},"alternative-id":["molecules25040815"],"URL":"https:\/\/doi.org\/10.3390\/molecules25040815","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,2,13]]}}}