6-Hydroxyisocaryophyllene and isocaryophyllenic acid from birches vegetative buds

Abstract

The new isocaryophyllene derivatives were first detected in the birch vegetative buds. The structure of 6-hydroxyisocaryophyllene [(1R,4Z, 6R, 9S)-8-methylene-11,11-dimethylbicyclo[7.2.0]undec-4-ene-6-ol] isolated from the Betula pendula Roth. birch buds was determined by NMR spectroscopy. The structures of caryophyllenic acid and isocaryphyllenic acid isolated from the Betula grandifolia Litv., B. albo-sinensis Burk., B. fusca Pall.ex Georg, B. obscura A. Kotula, B. litwinowii Doluch., B. hallii Howell, B. grandifolia Litv. birch buds was determined by X-ray diffraction analysis. The physico-chemical characteristics and NMR data of 6-hydroxyisocaryophyllene, epoxide of 6-hydroxyisocaryophyllene and all the isolated acids are given. The gas chromatographic retention indices of all identified compounds were determined.

p-COUMARATES OF BETULA PENDULA (BETULACEAE) VEGETATIVE BUDS SESQUITERPENE ALCOHOLS

“…Individual coumarate was isolated by triplicate chromatography on silica gel with an eluent system: hexane -MTBE (11-12%). The proton signal, which was observed in the NMR spectrum with a center at 5.743 ddd, was similar to the proton signal at 6 carbon in the NMR 1 H spectrum of 6-hydroxyisocaryophyllene recently isolated from birch bud [5].…”

“…1). The magnetic interaction of protons in the two-dimensional NOESY NMR spectrum was similar to the interaction of protons in the corresponding spectrum of 6-hydroxyisocaryophyllene [5].…”