Effect of 6 alpha,7 beta-dihydroxyvouacapan-17 beta-oic acid and its lactone derivatives on the growth of human cancer cells.
The furanditerpene 6 alpha,7 beta-dihydroxyvouacapan-17 beta-oic acid (1) is a natural product biosynthesized by some species from the genus Pterodon (Leguminosae). This secondary metabolite has multiple biological activities that include anti-inflammatory, analgesic, plant growth regulatory, anti-edematogenic, photosystem II inhibitory and photosynthesis uncoupler, and antifungal properties. However, few studies on the antiproliferative profile of compound 1 and/or its derivatives have been reported up to date. Here, we describe the isolation of compound 1 from hexane extract of P. polygalaeflorus fruits as well as the semisynthesis of three lactone derivatives: 6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone (2), 6 alpha-acetoxyvouacapan-7 beta,17 beta-lactone (3), and 6-oxovouacapan-7 beta,17 beta-lactone (4). Additionally, antiproliferative activity of these compounds against nine human cancer cell lines was investigated. Our results revealed that 6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone (2) was the most potent furanditerpene against all cancer cell lines studied. The presence of non-substituted hydroxyl group at C-6 and the presence of 7 beta,17 beta-lactone ring are important for the antiproliferative activity of these compounds.
Euzébio
Felipe P G
FP
Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais (UFMG), Av. Pres. Antônio Carlos, 6627, Campus Pampulha, 31270-901 Belo Horizonte, MG, Brazil.
dos Santos
Flávio J L
FJ
Piló-Veloso
Dorila
D
Ruiz
Ana Lúcia T G
AL
de Carvalho
João Ernesto
JE
Ferreira-Alves
Dalton L
DL
de Fátima
Angelo
A
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D007887:Fabaceae / Q000737:chemistry*; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology
C542507:6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone; D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes; D007783:Lactones; C073437:vouacapan