The Secalosides, Novel Tumor Cell Growth Inhibitory Glycosides from a Pollen Extract

Article Article scientifique Article The Secalosides, Novel Tumor Cell Growth Inhibitory Glycosides from a Pollen Extract eng 1997 author Jaton Jean-Claude 25363 author Roulin Seka Karen 27082 Karen Margrete Roulin Seka author Rose Keith 21876 author Sirotnak Francis M. author Lewenstein Ari author Brunner Gérard author Fankhauser Catherine 27502 author Burger Ulrich 25497 356-360 10.1021/np9606557 0163-3864 https://pubs.acs.org/doi/10.1021/np9606557 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. Dewey 540 Swiss National Science Foundation 31-43373.95 CH Swiss National Science Foundation 20-45806.95 CH 36 Département de chimie organique 141 false Journal of Natural Products 60 4 7b05c071-9cbd-4a87-9b24-1c49e7d9d965 Article (Published version) Restricted np9606557.pdf 149688 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

Title	Published in	Access level	OA Policy	Year	Views	Downloads

The Secalosides, Novel Tumor Cell Growth Inhibitory Glycosides from a Pollen Extract	Journal of Natural Products			1997	289	0

Archive ouverte UNIGE

Fankhauser, Catherine