title: Rearranged Terpenoids from the Marine Sponge Darwinella cf. oxeata and Its Predator, the Nudibranch Felimida grahami.
abstract: Marine sponges are a rich source of terpenoids with rearranged spongian carbon skeletons. Investigation of extracts from the sponge Darwinella cf. oxeata yielded four new rearranged diterpenoids, oxeatine (2) and oxeatamides H-J (3-5), as well as the known metabolites oxeatamide A (6), oxeatamide A methyl ester (7), and membranolide (1). Oxeatine (2) has a new heterocyclic skeleton, while oxeatamide J (5) has an N-methyl urea group included in a γ-lactam moiety. UPLC-QTOF analysis of the extract obtained from the mantle of the nudibranch Felimida grahami indicated the presence of 1 and 4.
authors.affiliation: Instituto de Química de São Carlos, Universidade de São Paulo , CP 780, CEP 13560-970, São Carlos, SP, Brazil.
authors.forename: Maria Camila
authors.initials: MC
authors.lastname: A Ramirez
authors.affiliation: Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia , Vancouver, BC V6T 1Z1, Canada.
authors.forename: David E
authors.initials: DE
authors.lastname: Williams
authors.affiliation: Instituto de Química de São Carlos, Universidade de São Paulo , CP 780, CEP 13560-970, São Carlos, SP, Brazil.
authors.forename: Juliana R
authors.initials: JR
authors.lastname: Gubiani
authors.affiliation: Instituto de Química de São Carlos, Universidade de São Paulo , CP 780, CEP 13560-970, São Carlos, SP, Brazil.
authors.forename: Lizbeth L L
authors.initials: LL
authors.lastname: Parra
authors.affiliation: Instituto de Química de São Carlos, Universidade de São Paulo , CP 780, CEP 13560-970, São Carlos, SP, Brazil.
authors.forename: Mario F C
authors.initials: MF
authors.lastname: Santos
authors.affiliation: Centre for Parasitology and Mycology, Instituto Adolfo Lutz , Avenida Dr. Arnaldo, 351, 8° andar, 01246-000 São Paulo, SP, Brazil.
authors.forename: Daiane D
authors.initials: DD
authors.lastname: Ferreira
authors.affiliation: Centre for Parasitology and Mycology, Instituto Adolfo Lutz , Avenida Dr. Arnaldo, 351, 8° andar, 01246-000 São Paulo, SP, Brazil.
authors.forename: Juliana T
authors.initials: JT
authors.lastname: Mesquita
authors.affiliation: Centre for Parasitology and Mycology, Instituto Adolfo Lutz , Avenida Dr. Arnaldo, 351, 8° andar, 01246-000 São Paulo, SP, Brazil.
authors.forename: Andre G
authors.initials: AG
authors.lastname: Tempone
authors.affiliation: Departamento de Química, Universidade Federal de São Carlos , Rodovia Washington Luis s/n, km 235, CEP 13565-905 São Carlos, SP, Brazil.
authors.forename: Antonio G
authors.initials: AG
authors.lastname: Ferreira
authors.affiliation: Departamento de Biotecnologia R. Kioto, Instituto de Estudos do Mar Almirante Paulo Moreira (IEAPM) , 253 - Praia dos Anjos, 28930-000 Arraial do Cabo, RJ, Brazil.
authors.forename: Vinícius
authors.initials: V
authors.lastname: Padula
authors.affiliation: Museu Nacional, Universidade Federal do Rio de Janeiro , Quinta da Boa Vista, s/n, CEP 20940-040 Rio de Janeiro, RJ, Brazil.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Hajdu
authors.affiliation: Departments of Chemistry and Earth, Ocean & Atmospheric Sciences, University of British Columbia , Vancouver, BC V6T 1Z1, Canada.
authors.forename: Raymond J
authors.identifier: 0000-0002-7607-8213
authors.initials: RJ
authors.lastname: Andersen
authors.affiliation: Instituto de Química de São Carlos, Universidade de São Paulo , CP 780, CEP 13560-970, São Carlos, SP, Brazil.
authors.forename: Roberto G S
authors.identifier: 0000-0003-0118-2523
authors.initials: RG
authors.lastname: Berlinck
mesh_terms: D000818:Animals; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification*; D049851:Gastropoda / Q000737:chemistry*; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification*
chemical_list: D004224:Diterpenes; D013729:Terpenes