Search results for "Atractyligenin"

Cytotoxic activity of several ent-kaurane derivatives of atractyligenin. Synthesis of unreported diterpenic skeleton by chemical rearrangement

2022

Atractyloside, carboxyatractyloside, their aglycon atractyligenin, and several synthetic derivatives were tested and found to be active against a panel of human tumor cell lines. Atractyligenin was subjected to oxidation, bromination, and elimination reactions, obtaining several compounds. A singular skeleton was synthesized by chemical rearrangement starting from 3 beta-bromo-2,15-diketoatractyligenin methyl ester. The synthesized compounds resulted active against all cell lines tested. In particular, 15-ketoatractyligenin methyl ester and 3 beta bromo-2,15-diketoatractyligenin methyl ester resulted the most active with IC50 values of 0.427 and 0.723 mu M against A375 melanoma cell line. E…

The crystal and molecular structure of the epoxybromo derivative of atractyligenin.

1970

Abstract The complete configuration of atractyligenin has been obtained by a three-dimensional single-crystal X-ray difiraction study. Previous structural work has been confirmed, in particular the configuration of the epoxy group. The space group is C2, with four molecules in the cell, a = 19·005, b = 7·165, c = 14·450 A, β = 108° 31′, and the final R is 0·125 for 1320 observed reflections. The stress in the molecule (as indicated by the torsional angles) and the molecular packing are discussed.

New oxidative derivatives of atractyligenin and their cytotoxic activity

2006

ent-Kauranes are naturally occurring diterpenoids isolated from several families, such as Asteraceae and Lamiaceae. These compounds have attracted interest because of their structures and their biological activities as anti-tumorals, anti-HIV and anti-bacterials [1]. Extensive chemical work [2] was carried out on the structure of atractyligenin, the nor-diterpene aglycone of the glucoside atractyloside, occurring, together with its diterpene homologous carboxy-atractyloside, in the root of Atractylis gummifera L. (Compositae). The interest for these compounds was stimulated by the high toxicity [3] of both glucosides, responsible of many deadly poisoning in past time. Due to the 15-hydroxyl…

Atractyligenin chemistry. Part 4: Synthesis of the 15β-ol epimer of atractyligenin

1996

The oxidation with PCC of atractyligenin 3, the aglicone of the toxic glycoside 1 isolated from Atractylis gummifera L., led to the 15-oxo-derivative 6, together with a small amount of 2,15-dioxoderivative 5, with a selective oxidation of the allylic 15-OH group of the molecule. Further reduction with NaBH4 and KOH hydrolysis gave stereoselectively the 15β-ol epimer of atractiligenin 9.

The structure of atractyligenin.

1965

ChemInform Abstract: Photoinduced Functionalization of the C-20 Methyl Group of the Nor-diterpene Atractyligenin.

2010

Abstract Irradiation of the nor-diterpene atractyligenin at λ =254 nm in methanol gave, on one hand, the decarboxylation product, and provided, on the other hand, the transformation of the C-20 angular methyl into a methylene-carbomethoxy group. A photochemical pathway involving formation of C-19/C-20 bond is suggested.

The structure and stereochemistry of atractyligenin

1966

Abstract The structure of atractyligenin C19H28O4, the nor-diterpenoidic aglycone of atractyloside C30H44O16S2K2 has been substantiated as Ia. The absolute configuration shown in Ia proves it to be a derivative of (−)kaurene.

Photoinduced functionalization of the C-20 methyl group of the nor-diterpene atractyligenin

2001

Abstract Irradiation of the nor-diterpene atractyligenin at λ =254 nm in methanol gave, on one hand, the decarboxylation product, and provided, on the other hand, the transformation of the C-20 angular methyl into a methylene-carbomethoxy group. A photochemical pathway involving formation of C-19/C-20 bond is suggested.