Naslov
Centrifugal Partition Chromatography as a New Tool for the Efficient and Green Purification of Highly-Polar and Unstable Products on Multigram Scale

Autori
Dean Marković, Raphael Grougnet, Yse Salle de Chou, Brigitte Deguin

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Book of Abstracts 18th European Congress in Organic Chemistry, July 7-12 / - Marseille, 2013, 444-444

Skup
18th European Congress in Organic Chemistry, July 7-12

Mjesto i datum
Marseille, Francuska, July 7-12

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
aucubin, Eucommiol, iridolactone, centrifugal partition chromatography

Sažetak
Centrifuga! partition chromatography (CPC) is emerging technique far the purification of natural products. Despite its high-efficiency and green character, this method was really used far the purification of synthetic intermediates with chemical value. Our research program concerns new medicinal chemical leads obtained by semisynthetic methods from plant secondary metabolites. Far instance, we use aucubin 1 as abundant natural compound to create new chiral scaffalds and building blocks far the synthesis. In addition, the libraries of biological interest can be obtained and evaluated far cytotoxic1 or antimlcroblal activities (Scheme 1) .2 The aucubin 1 can be isolated from the leaves, roots, stems and seeds of Plantago asiatica, Eucommia ulmoides and Aucuba japonica Thunb. 3 In our efforts to improve the isolation process in terms of green chemistry and sustainable development, we have developed fast and efficient purification employing CPC. Our method can be performed on large scale of the natural extract. In addition, to the aucubin 1 (2.2 %) the centrifugal partition chromatography on SCPC Armen lL apparatus led to the isolation of two biologically related iridoid aglycones, iridolactone 2 (0.05 % ) and Eucommiol 3 (0.08 %) as presented in Scheme 1. Our interest was further expanded to the utilization of CPC as green method far the multigram purification of highly polar and unstable products in synthesis. For example, monodeoxyaucubin 2 and dideoxyaucubin 3 obtained by Birch reduction of aucubin 1, 4 are difficult to purify by chromatographic methods due to the high contents of salts. CPC purification of these products yielded 86 and 80 % of aucubin derivatives 2 and 3, respectively. Furthermore, the cleavage of glycosidic bond of aucubin derivatives 1, 4 , 5 lead to isolation of very unstable aglycons 6 , 7, 8 that were successfully purified by CPC chromatography in 91, 87, 76 % . We acknowledge financial support from the ANR (ANR-09-CP2D-09-01: IRNACHIR-2009).

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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