title: ent-Kaurane diterpenes from the stem bark of Annona vepretorum (Annonaceae) and cytotoxic evaluation.
abstract: This work describes a novel ent-kaurane diterpene, ent-3β-hydroxy-kaur-16-en-19-al along with five known ent-kaurane diterpenes, ent-3β,19-dihydroxy-kaur-16-eno, ent-3β-hydroxy-kaur-16-eno, ent-3β-acetoxy-kaur-16-eno, ent-3β-hydroxy-kaurenoic acid and kaurenoic acid, as well as caryophyllene oxide, humulene epoxide II, β-sitosterol, stigmasterol and campesterol from the stem bark of Annona vepretorum Mart. (Annonaceae). Cytotoxic activities towards tumor B16-F10, HepG2, K562 and HL60 and non-tumor PBMC cell lines were evaluated for ent-kaurane diterpenes. Among them, ent-3β-hydroxy-kaur-16-en-19-al was the most active compound with higher cytotoxic effect over K562 cell line (IC50 of 2.49 μg/mL) and lower over B16-F10 cell line (IC50 of 21.02 μg/mL).
authors: Department of Chemistry, Federal University of Sergipe, São Cristóvão, Sergipe, Brazil.
authors: Lívia M
authors: LM
authors: Dutra
authors: Gonçalo Moniz Research Center, Oswaldo Cruz Foundation (Fiocruz), Rua Waldemar Falcão, 121, Candeal, 40296-710 Salvador, Bahia, Brazil.
authors: Larissa M
authors: LM
authors: Bomfim
authors: Gonçalo Moniz Research Center, Oswaldo Cruz Foundation (Fiocruz), Rua Waldemar Falcão, 121, Candeal, 40296-710 Salvador, Bahia, Brazil.
authors: Suellen L A
authors: SL
authors: Rocha
authors: NMR Center, Department of Chemistry, Federal University of Paraná, Curitiba, Paraná, Brazil.
authors: Angelita
authors: A
authors: Nepel
authors: Gonçalo Moniz Research Center, Oswaldo Cruz Foundation (Fiocruz), Rua Waldemar Falcão, 121, Candeal, 40296-710 Salvador, Bahia, Brazil; Center of Biotechnology and Cell Therapy, Hospital São Rafael, Salvador, Bahia, Brazil.
authors: Milena B P
authors: MB
authors: Soares
authors: NMR Center, Department of Chemistry, Federal University of Paraná, Curitiba, Paraná, Brazil.
authors: Andersson
authors: A
authors: Barison
authors: Department of Chemistry, Federal University of Sergipe, Itabaiana, Sergipe, Brazil.
authors: Emmanoel V
authors: EV
authors: Costa
authors: Gonçalo Moniz Research Center, Oswaldo Cruz Foundation (Fiocruz), Rua Waldemar Falcão, 121, Candeal, 40296-710 Salvador, Bahia, Brazil. Electronic address: danielpbezerra@gmail.com.
authors: Daniel P
authors: DP
authors: Bezerra
mesh_terms: D000818:Animals; D029061:Annonaceae / Q000737:chemistry*; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D045786:Diterpenes, Kaurane / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D056945:Hep G2 Cells; D006801:Humans; D020014:K562 Cells; D007963:Leukocytes, Mononuclear / Q000187:drug effects*; D051379:Mice; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry*; D018547:Plant Stems / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D045786:Diterpenes, Kaurane
keywords: Annona vepretorum; Annonaceae; Cytotoxicity; ent-Kaurane diterpenes