A new bioactive steroidal saponin, furcreastatin, from the plant Furcraea foetida.
Microbial and plant secondary metabolites were screened for compounds that are selectively cytotoxic to mutant p53-expressing mouse fibroblasts. As a result, furcreastatin, a novel steroidal saponin, was isolated from an EtOH extract of the leaves of Furcraea foetida. Furcreastatin consisted of hecogenin as the aglycone and a hexasaccharide containing D-galactose, L-rhamnose and four D-glucose residues. The structure was determined to be (3 beta,5 alpha,25R)- 3-hydroxyspirostan-12-one 3-O-[alpha-L-Rhap-(1-->4)-beta-D-Glcp-(1-->3)-¿beta-D-Glcp-(1-->3) -beta-D- Glcp-(1-->2)¿-beta-D-Glcp-(1-->4)-beta-D-Galp] by extensive NMR spectroscopic studies. Furcreastatin decreased the viability of mutant p53-over-expressing cells with an ED50 of 4.0 micrograms/mL, and decreased that of the parental cell-line with an ED50 of 9.6 micrograms/mL.
Itabashi
M
M
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Yokohama, Japan.
Segawa
K
K
Ikeda
Y
Y
Kondo
S
S
Naganawa
H
H
Koyano
T
T
Umezawa
K
K
D016475:3T3 Cells; D000818:Animals; D002240:Carbohydrate Sequence; D016923:Cell Death; D016158:Genes, p53 / Q000235:genetics; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008807:Mice, Inbred BALB C; D008969:Molecular Sequence Data; D009154:Mutation; D010936:Plant Extracts / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology*; D013150:Spirostans; D013696:Temperature; D014162:Transfection; D014407:Tumor Cells, Cultured; D016159:Tumor Suppressor Protein p53 / Q000378:metabolism
D010936:Plant Extracts; D012503:Saponins; D013150:Spirostans; D016159:Tumor Suppressor Protein p53; C410149:furcreastatin