Carbon‐13 NMR spectra of five sesquiterpenes isolated from Ylang Ylang essential oil

Abstract

13C NMR chemical shifts are given for germacrene‐D, α‐humulene, δ‐cadinene, ε‐cadinene and γ‐muurolene isolated from Ylang Ylang (Cananga odorata, forma genuina) essential oil.

Macrocarpane, a new sesquiterpene skeleton from the leaves of Porcelia macrocarpa

“…This spectrum also showed a signal at δ 0.51 (m), suggesting the presence of a cyclopropane ring in the structure of 10. The observation of a double-multiplete at δ 48.6, in the gated 13 C NMR spectrum with J 163 Hz, characteristic of three member ring, 9 confirms the cyclopropane ring in the molecule. The HMQC spectrum showed long-range correlations between carbons and hydrogens ( Table 1).…”

“…The hexane extract of the leaves of P. macrocarpa was submitted to chromatographic separations to give two sesquiterpenes: spathulenol (7) and macrocarp-11(15)-en-8-ol (10), one diterpene: phytol (11) and two steroids: sistosta-5,25-dien-3β-ol (12) and sitosta-5,22,25-trien-3β-ol (13). The sesquiterpene 7, the diterpene 11 and the steroids 12 and 13 were identified by analysis of their 1 H and 13 C NMR data and comparison with data described in the literature.…”

“…The sesquiterpene 7, the diterpene 11 and the steroids 12 and 13 were identified by analysis of their 1 H and 13 C NMR data and comparison with data described in the literature. [5][6][7][8] Macrocarpane, a New Sesquiterpene Skeleton from the Leaves of Porcelia macrocarpa Vol.…”

“…12 The sesquiterpenes 3, 4, 7, 8 and 9 and the diterpene 11 were characterized as the 5,[13][14][15] . Additionally, the crude volatile oil was submitted to analysis by GC/MS.…”

“…The group I (351 mg) was submitted to flash chromatography on silica gel and eluted with hexaneEtOAc (6:4, v/v) yielding 7 (77 mg). Group II (720 mg) was methylated with diazomethane, submitted to flash chromatography on silica gel and eluted with hexaneEtOAc The fresh plant material (2250 g) was hydrodistilled 13 C on Brüker DPX-300 and DRX-500 spectrometers using CDCl 3 as solvent and internal standard. The GC analysis was performed in a Hewlett-Packard 5890 series II (using helium as carrier gas) equipped with a FID detector and a capillary column HP-5, crosslinked 5% phenyl in 95% methyl silicone (30 m x 0.32 mm, film thickness 0.25 µm) with a automatic injector (HP 7673) and an electronic integrator (HP 3396A).…”