Isfahan University of Medical Sciences

Science Communicator Platform

Stay connected! Follow us on X network (Twitter):
Share this content! On (X network) By
3,4-Seco-Spirostane Sapogenins With Cytotoxic Activity From Allium Umbilicatum Boiss Publisher



Zolfaghari B1 ; Sadeghi M1 ; Troiano R2 ; Lanzotti V2
Authors
Show Affiliations
Authors Affiliations
  1. 1. Department of Pharmacognosy, Isfahan University of Medical Sciences, Hezar Jerib Avenue, Isfahan, 73461, Iran
  2. 2. Dipartimento di Agraria, Universita di Napoli Federico II, Via Universita 100, Portici, Naples, 80055, Italy

Source: Phytochemistry Letters Published:2015


Abstract

Abstract Two new sapogenins, named seco-umbilicagenins A and B (1 and 2), possessing a new chemical structure based on a 3,4-seco-spirostane skeleton, were isolated from Allium umbilicatum Boiss. The chemical structures of seco-umbilicagenins A and B were established through a combination of extensive spectroscopic analysis, mainly nuclear magnetic resonance spectroscopy and mass spectrometry, and chemical methods as (2S,25R)-2,5α,6β-trihydroxy-3,4-seco-spirosta-3,4-dioic acid (1) and (2S,25R)-2,4,5α-trihydroxy-6-oxo-3,4-seco-spirostan-3-oic acid (2). Interestingly, the isolated compounds exhibited cytotoxic activity on J-774, murine monocyte/macrophage, and WEHI-164, murine fibrosarcoma, cell lines. To the best of our knowledge this is the first time that 3,4-seco-spirostane sapogenins are isolated from natural sources, being this skeleton obtained by synthetic modification of intact sapogenins. © 2015 Phytochemical Society of Europe.