New cytotoxic prenylated isoflavonoids from Bituminaria morisiana.
Using cytotoxicity against KB cancer cells as a lead, bioguided-fractionation of the petroleum ether and ethyl acetate extracts of Bituminaria morisiana leaves led to the isolation of two new pterocarpans, namely 3,9-dihydroxy-4-(3,3-dimethylallyl) [6a R, 11a R]-pterocarpan, 3-hydroxy-4-(3,3-dimethylallyl)-4'',5''-dehydropyrano[8,9:2'',3''][6a R,11a R]-pterocarpan and one new isoflavone identified as 4',5''-dihydroxy-6''-methoxy-4'',4''-dimethyl-4'',5''-dihydro-6'' H-pyrano[2'',3'':7,8]-isoflavone. Moreover, two known pterocarpans, erybraedin C and bitucarpin A, three known isoflavones, daidzein, 8-prenyldaidzein and bidwillon C, one known furocoumarin, pseudoisopsoralen and one known coumestan, coumestrol were isolated. The structures of the isolated compounds were established by means of 1D and 2D NMR spectroscopy, as well as mass spectrometry. Further cytotoxicity tests against cells related to the immune system (Jurkat T, Mono-Mac-6 and polymorphonuclear cells) showed a moderate activity of the known pterocarpan erybraedin C against all cell lines used (IC (50) values between 17.6-28.8 microM). In addition, erybraedin C was found to induce necrosis in leukaemia Jurkat T cells.
Cottiglia
Filippo
F
Dipartimento Farmaco Chimico Tecnologico, Faculty of Pharmacy, University of Cagliari, Via Ospedale 72, 09124 Cagliari, Italy. cottiglf@unica.it
Casu
Laura
L
Bonsignore
Leonardo
L
Casu
Mariano
M
Floris
Costantino
C
Leonti
Marco
M
Gertsch
Jürg
J
Heilmann
Jörg
J
D000972:Antineoplastic Agents, Phytogenic / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D045744:Cell Line, Tumor / Q000187:drug effects; D007887:Fabaceae; D006801:Humans; D020128:Inhibitory Concentration 50; D007529:Isoflavones / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D019169:Jurkat Cells / Q000187:drug effects; D007624:KB Cells / Q000187:drug effects; D009000:Monocytes / Q000187:drug effects; D008517:Phytotherapy; D010936:Plant Extracts / Q000008:administration & dosage / Q000737:chemistry / Q000494:pharmacology* / Q000627:therapeutic use; D018515:Plant Leaves; D017368:Protein Prenylation
D000972:Antineoplastic Agents, Phytogenic; D007529:Isoflavones; D010936:Plant Extracts