The secalosides, novel tumor cell growth inhibitory glycosides from a pollen extract.
The pollen of rye (Secale cereale) was shown to contain a biologically highly active family of glycosides called the secalosides. Secalosides A and B (1), both of molecular formula C46H51-NO24, were found to be epimeric esters of (2-oxo-3-indolyl)acetic acid (4). They are made up, in addition to this heterocyclic aglycon I (4), of three hexose building blocks and a carbocyclic aglycon II, which is an indan-derived dicarboxylic acid (5). In aqueous solution, secalosides A and B interchanged by epimerization at the chiral center of 4. A further epimeric pair, secalosides C and D (2), contain one additional glucose building block. Secalosides A and B, the racemic aglycon I (4), and 2-oxo-1,2,3, 4-tetrahydroquinoline-4-carboxylic acid (3), which results from 4 by hydrolytic rearrangement, exhibited significant antitumor activity against S180 sarcoma in vivo. IC50 values obtained were about 5 micrograms/mouse for the secalosides and 1 microgram/mouse for 3 and 4.
Jaton
J C
JC
Department of Medical Biochemistry, University of Geneva, Switzerland. Jaton@cmu.unige.ch
Roulin
K
K
Rose
K
K
Sirotnak
F M
FM
Lewenstein
A
A
Brunner
G
G
Fankhauser
C P
CP
Burger
U
U
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006868:Hydrolysis; D007210:Indoleacetic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007536:Isomerism; D051379:Mice; D008970:Molecular Weight; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D011058:Pollen / Q000737:chemistry*; D012434:Secale / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured
D000972:Antineoplastic Agents, Phytogenic; D005960:Glucosides; D007210:Indoleacetic Acids; D010936:Plant Extracts; C106015:secaloside A; C106016:secaloside C