Laboratoire Of Pharmacognosie Et Of Phytochimie

Limoges, France

Laboratoire Of Pharmacognosie Et Of Phytochimie

Limoges, France

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Kaouadji M.,Faculte des science et Techniques | Bennini B.,Laboratoire Of Pharmacognosie Et Of Phytochimie | Chulia A.J.,Laboratoire Of Pharmacognosie Et Of Phytochimie
Tetrahedron Letters | Year: 2012

Continuation of the phytochemical analysis of Erica cinerea fresh aerial parts resulted in the isolation of two new compounds with a very close chromatographic behavior. On the basis of spectroscopic evidence (UV, MS and NMR), the structures were established as (-)-(3S,6E)-1,9-bis(p-hydroxyphenyl)-3- hydroxynon-6-en-5-one 3-O-β-d-glucoside named 6,7-anhydroericaone 3-O-β-d-glucoside and (-)-(3S)-1,9-bis(p-hydroxyphenyl)-3-hydroxynonan-5,6- dione 3-O-β-d-glucoside named α-ericadione 3-O-β-d-glucoside. Unanticipated by its α-alkadione type structure - a very unusual feature in the plant kingdom - the latter metabolite was found as a mixture of the minor s-cis and the major s-trans conformers. Moreover, the GC-MS analysis of the aglycone moieties of such glucosides, pointed out the permanent absence of the molecular ion and the constant hydroxybenzylium base peak, as well as the conversion of the α-dione into the major α-keto-enol tautomer. © 2012 Published by Elsevier Ltd.


Kaouadji M.,Faculte des science et Techniques | Bennini B.,Laboratoire Of Pharmacognosie Et Of Phytochimie | Chulia A.J.,Laboratoire Of Pharmacognosie Et Of Phytochimie
Tetrahedron Letters | Year: 2013

In addition to the six diarylnonanoids and diarylnonanoid 3-O-glucosides previously reported from Erica cinerea, the multistep chromatographic processing of the acetone extract of the fresh aerial parts resulted in the isolation of three more representatives as glycosides derived from either (-)-ericanone or (-)-α-ericadione. From the spectroscopic data, the new structures were elucidated as (-)-(3S,7S)-ericanone 3-O-β-d-xylopyranoside, (-)-(3S,7S)-3″-hydroxyericanone 3-O-β-d-glucopyranoside, and (-)-(3S)-3″-hydroxy-α-ericadione 3-O-β-d-glucopyranoside respectively. In the 1H and 13C NMR spectra run in CD 3OD, the latter metabolite was as (-)-α-ericadione 3-O-β-d-glucopyranoside, also found as a permanent mixture of the major s-trans (70%) and the minor s-cis (30%) conformers. Such result - in connection with the protic solvent - seems to have never been reported earlier for α-alkadiones. Moreover, mild acid hydrolysis of such a glucoside led directly to the 3,4-dehydrated aglycone moiety accompanied by its 6,7-dehydrated tautomer, according to two successive dehydrations of the anticipated aglycone. Furthermore, although missing in this species, the postulated β-ericadione continues to be regarded as an essential intermediate at the crossroads of the biogenesis of most of the E. cinerea 1,9-diarylnonanoids. © 2013 Elsevier Ltd. All rights reserved.

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