In vitro anti-proliferation/cytotoxic activity of epingaione and its derivatives on the human SH-SY5Y neuroblastoma and TE-671 sarcoma cells.
Epingaione (4-Methyl-1-(5-methyl-2, 3,4,5-tetrahydro-[2,3']bifuranyl-5-yl)-pentan-2-one) was isolated as one of the major lipophilic secondary metabolites from the leaves and stems of Bontia daphnoides L. The compound gave 79.24% and 50.83% anti-proliferation/cytotoxic activity on the human SH-SY5Y neuroblastoma and TE-671 sarcoma cells in vitro at 50 pg/mL, respectively. Epingaione was transformed into eleven derivatives under laboratory conditions using ethanol, some gave greater anti-proliferation/cytotoxic activity on the cancer cell lines tested. One of the derivatives (compound 2) with enhanced cytotoxic activity was elucidated as 5'-Ethoxy-5-methyl-5-(4-methyl-2-oxo-pentyl)-2,3,4,5-tetrahydro-5'H-[2,3']bifuranyl-2'-one. Both epingaione and compound 2 caused an accumulation of arrested or dead SH-SY5Y neuroblastoma in the m-phase of the cell cycle as revealed by the m-phase specific marker KE 67.
Williams
L A D
LA
The University of Hohenheim, Institutes for Bio-organic Chemistry , Garbenstr 30, D-70593 Stuttgart, Germany. lawrencew@src-jamaica.org
Conrad
J
J
Vogler
B
B
Rösner
H
H
Porter
R B R
RB
Setzer
W
W
Barton
E N
EN
Levy
H G
HG
Mika
S
S
Klaiber
I
I
Nkurunziza
J P
JP
Kraus
W
W
D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival; D004354:Drug Screening Assays, Antitumor; D005663:Furans / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D031642:Myoporaceae; D009447:Neuroblastoma / Q000188:drug therapy*; D010422:Pentanones / Q000737:chemistry / Q000494:pharmacology*; D008517:Phytotherapy; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D018515:Plant Leaves; D018547:Plant Stems; D012509:Sarcoma / Q000188:drug therapy*
C522126:4-methyl-1-(5-methyl-2, 3,4,5-tetrahydro-(2,3')bifuranyl-5-yl)-pentan-2-one; D005663:Furans; D010422:Pentanones; D010936:Plant Extracts