Two new sapogenins, named seco-umbilicagenins A and B (1 and 2), possessing a new chem. structure based on a 3,4-seco-spirostane skeleton, were isolated from Allium umbilicatum Boiss. The chem. structures of seco-umbilicagenins A and B were established through a combination of extensive spectroscopic anal., mainly NMR spectroscopy and mass spectrometry, and chem. 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 compds. 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. [on SciFinder(R)]
3,4-Seco-spirostane sapogenins with cytotoxic activity from Allium umbilicatum boiss / Zolfaghari, Behzad; Sadeghi, Masoud; Troiano, Raffaele; Lanzotti, Virginia. - In: PHYTOCHEMISTRY LETTERS. - ISSN 1874-3900. - 12:(2015), pp. 291-295. [10.1016/j.phytol.2015.04.019]
3,4-Seco-spirostane sapogenins with cytotoxic activity from Allium umbilicatum boiss
TROIANO, RAFFAELE;LANZOTTI, VIRGINIA
2015
Abstract
Two new sapogenins, named seco-umbilicagenins A and B (1 and 2), possessing a new chem. structure based on a 3,4-seco-spirostane skeleton, were isolated from Allium umbilicatum Boiss. The chem. structures of seco-umbilicagenins A and B were established through a combination of extensive spectroscopic anal., mainly NMR spectroscopy and mass spectrometry, and chem. 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 compds. 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. [on SciFinder(R)]I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
