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 group of atractyligenin, it was possible to design a series of chemical reactions in order to build an α,β-unsaturated ketone in the kaurane skeleton. In fact, it is well know that the main determining factor responsible for cytotoxicity is the presence of an α,β-unsaturated system that likely serves as an alkylating center and can be part of an ester, ketone, or lactone moiety [4]. The same oxidative reaction carried out on atractylitriol gave unexpected products in which the allylic alcohol moiety was preserved. The cytotoxic tests of the compounds having an insaturated moiety (15-oxo-atractyligenin methyl ester and 2,15-dioxo-atractyligenin methyl ester) and of several ester derivatives of 15-oxo-atractyligenin methyl ester were performed against KB and KB-VIN tumor cell lines. They showed a good activity between 2.9–1.1µM comparable to mitomycin C (0.6µM)

BRUNO M, ROSSELLI S, MAGGIO AM, BELLONE G, LEE K-H (2006). New oxidative derivatives of atractyligenin and their cytotoxic activity. In New oxidative derivatives of atractyligenin and their cytotoxic activity (pp.996-996). Georg Thieme Verlag [10.1055/s-2006-949840].

New oxidative derivatives of atractyligenin and their cytotoxic activity

BRUNO, Maurizio;ROSSELLI, Sergio;MAGGIO, Antonella Maria;BELLONE, Gabriella;
2006-01-01

Abstract

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 group of atractyligenin, it was possible to design a series of chemical reactions in order to build an α,β-unsaturated ketone in the kaurane skeleton. In fact, it is well know that the main determining factor responsible for cytotoxicity is the presence of an α,β-unsaturated system that likely serves as an alkylating center and can be part of an ester, ketone, or lactone moiety [4]. The same oxidative reaction carried out on atractylitriol gave unexpected products in which the allylic alcohol moiety was preserved. The cytotoxic tests of the compounds having an insaturated moiety (15-oxo-atractyligenin methyl ester and 2,15-dioxo-atractyligenin methyl ester) and of several ester derivatives of 15-oxo-atractyligenin methyl ester were performed against KB and KB-VIN tumor cell lines. They showed a good activity between 2.9–1.1µM comparable to mitomycin C (0.6µM)
Settore CHIM/06 - Chimica Organica
2006
Annual Congress on Medicinal Plant Research
Helsinki, FINLAND
aug 29-sep 02, 2006
54th
2006
1
A stampa
https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-2006-949840
BRUNO M, ROSSELLI S, MAGGIO AM, BELLONE G, LEE K-H (2006). New oxidative derivatives of atractyligenin and their cytotoxic activity. In New oxidative derivatives of atractyligenin and their cytotoxic activity (pp.996-996). Georg Thieme Verlag [10.1055/s-2006-949840].
Proceedings (atti dei congressi)
BRUNO M; ROSSELLI S; MAGGIO AM; BELLONE G; LEE K-H
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/16603
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