Diarylnonanoids and their glucosides from Erica cinerea

• Published in: Tetrahedron letters 2011-04, Vol.52 (14), p.1597-1600
• Main Authors: Bennini, Bachir, Chulia, Albert J., Kaouadji, Mourad, Fondanèche, Patrice, Allais, Daovy P.
• Format: Article
• Language: English
• Subjects: (2S)-2,6-Bis(p-hydroxyphenethyl)-2,3-dihydropyran-4-one; (3S)-3,7-Anhydro-6,7-dehydroericanone; (3S)-3,7-Anhydro-6,7-dehydroericanone 4′ glucoside; Aerials; Analytical chemistry; Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemical Sciences; Chemistry; Erica cinerea; Ericaceae; Ericanone; Ericanone 3-glucoside; Exact sciences and technology; Glucosides; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Preparations and properties; rel-(3R,7R)-1,9-Bis(p-hydroxyphenyl)-3,7-dihydroxynonan-5-one; Spectroscopy; Tetrahedrons
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2011.01.108

The acetone extract of Erica cinerea fresh aerial parts afforded the new diarylnonanoids 1 and 3 as well as the corresponding glucosides 2 and 4 with either open or partly cyclized C9 chain. The reinvestigation of Erica cinerea fresh aerial parts led to the isolation of two new diarylnonanoid aglycones along with their glucosides. From spectroscopic data, their structures were elucidated as rel-(3R,7R)-1,9-bis(p-hydroxyphenyl)-3,7-dihydroxynonan-5-one named ericanone, ericanone 3-β-d-glucoside, (3S)-3,7-anhydro-6,7-dehydroericanone and (3S)-3,7-anhydro-6,7-dehydroericanone 4′-β-d-glucoside. Contrary to the numerous diarylheptanoids more frequently distributed in the plant kingdom, the rare diarylnonanoids were previously restricted to the genus Myristica of the Myristicaceae plant family.