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 C46H51NO24, were found to be epimeric esters of (2-oxo-3-indolyl)acetic acid (4). They are made up, in addition to this...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1997-04, Vol.60 (4), p.356-360
Main Authors: Jaton, Jean-Claude, Roulin, Karen, Rose, Keith, Sirotnak, Francis M, Lewenstein, Ari, Brunner, Gérard, Fankhauser, Catherine P, Burger, Ulrich
Format: Article
Language:English
Subjects:
AGENTES ANTINEOPLASTICOS
Animals
ANTINEOPLASTIC AGENTS
Antineoplastic Agents, Phytogenic - chemistry
Antineoplastic Agents, Phytogenic - isolation & purification
Antineoplastic Agents, Phytogenic - pharmacology
Biological and medical sciences
CHEMICAL COMPOSITION
CHEMICAL STRUCTURE
Chromatography, High Pressure Liquid
COMPOSICION QUIMICA
COMPOSITION CHIMIQUE
ESPECTROMETRIA
ESTRUCTURA QUIMICA
General pharmacology
GLICOSIDOS
Glucosides - chemistry
Glucosides - isolation & purification
Glucosides - pharmacology
GLYCOSIDE
GLYCOSIDES
Hydrolysis
Indoleacetic Acids - chemistry
Indoleacetic Acids - isolation & purification
Indoleacetic Acids - pharmacology
Isomerism
Medical sciences
MEDICAMENT CYTOSTATIQUE
MEDICINAL PROPERTIES
Mice
Molecular Weight
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Extracts - chemistry
Plant Extracts - pharmacology
POLEN
POLLEN
Pollen - chemistry
PROPIEDADES MEDICINALES
PROPRIETE PHARMACOLOGIQUE
Secale - chemistry
SECALE CEREALE
SPECTRAL ANALYSIS
SPECTROMETRIE
SPECTROMETRY
Spectrometry, Mass, Fast Atom Bombardment
Spectrophotometry, Ultraviolet
STRUCTURE CHIMIQUE
Tumor Cells, Cultured
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Summary: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 C46H51NO24, 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 μg/mouse for the secalosides and 1 μg/mouse for 3 and 4.
ISSN:0163-3864
1520-6025
DOI:10.1021/np9606557