Stereochemistry of 14-hydroxy-β-caryophyllene and related compounds

Studies on Betula essential oils

“…The main component was isolated by Medium Pressure Liquid Chromatography (MPLC) in high purity. 13,16 Literature search and comparison with spectral data 23 confirmed the identity of this compound as 14-hydroxy-β-caryophyllene (1), which was found 20.5-37.5% in all investigated oils. β-Betulenal (2) which was isolated by MPLC from Betula essential oils was also synthesized.…”

“…[19][20][21][22] There have been many conflicts and disagreements concerning absolute configurations and structures of caryophyllene derivatives isolated from natural sources. [7][8][9]23 The buds of B. pendula, B. litwinowii and B. medwediewii collected from various parts of Turkey were hydrodistilled while B. browicziana and B. recurvata buds were subjected to simultaneous distillation-extraction method (SDE) using a Likens-Nickerson apparatus due to limited plant material. The bud oils were analysed by GC-MS.…”

A New Triterpene from Atalantia retusa Merr.

“…This compound was first reported as a constituent of Dischidia formosana [9]. The structures of 4 -6 were confirmed by comparison of their 13 C NMR data (see Experimental Part) with those of 5,7-dimethoxy-8-(3-methyl-2-oxybutyl)coumarin (4) [10], humulene (5) [11] and β -caryophyllene (6) [12].…”

Sesquiterpenoids and Diterpenoids from the Wood of Cunninghamia konishii and Their Inhibitory Activities against NO Production

“…The combined EtOAc soluble fraction was purified by repeated silica gel column chromatography and normal phase semipreparative high-performance liquid chromatography (HPLC) to obtain three new sesquiterpenoids, 2α-hydroxy-3,3,6α,9β-tetramethyltricyclo[4,3,2 1,4 ]undecane (1), 11-acetoxyeudesman-4β-ol (4), and 2α,3β-dihydroxy-4β-methyl-6,8,10-cadinatriene (6), four known sesquiterpenoids, 3,7,7,9-tetramethyloctahydro-3a,6-ethanoinden-9-ol (2) [17], cedrol (3) [18], 11-acetoxyeudesman-4α-ol (5) [19], and 4β,5β-epoxy-14-hydroxy-9-epi-β-caryophyllene (7) [20], in addition to three known compounds, sandaracopimaric acid (8) [21], elliotinol (9) [22], and 8α-hydroxy-15,16-bisnorlabda-11-en-13-one (10) [23] (Figure 1). The identification of the known compounds was established through direct comparison with the published physical and spectral data (IR (infrared), UV (ultraviolet), MS (mass spectrum), and NMR (nuclear magnetic resonance)).…”

“…Therefore, compound 1 was determined as 2α-hydroxy-3,3,6α,9β-tetramethyltricyclo[4,3,2 1,4 ]undecane with a new sesquiterpene skeleton. fraction was purified by repeated silica gel column chromatography and normal phase semipreparative high-performance liquid chromatography (HPLC) to obtain three new sesquiterpenoids, 2α-hydroxy-3,3,6α,9β-tetramethyltricyclo[4,3,2 1,4 ]undecane (1), 11-acetoxyeudesman-4β-ol (4), and 2α,3β-dihydroxy-4β-methyl-6,8,10-cadinatriene (6), four known sesquiterpenoids, 3,7,7,9-tetramethyloctahydro-3a,6-ethanoinden-9-ol (2) [17], cedrol (3) [18], 11-acetoxyeudesman-4α-ol (5) [19], and 4β,5β-epoxy-14-hydroxy-9-epi-β-caryophyllene (7) [20], in addition to three known compounds, sandaracopimaric acid (8) [21], elliotinol (9) [22], and 8α-hydroxy-15,16-bisnorlabda-11-en-13-one (10) (Table 1) and were assigned by the distortionless enhancement by polarization transfer (DEPT) experiments as four aliphatic methyl, five aliphatic methylene, two aliphatic methine, three aliphatic quaternary, and one oxygenated methine carbons. Its 1 H-NMR spectrum ( Table 1) revealed signals of the presence of one oxygenated methine (δH 3.04 (s)), three singlet methyls (δH 0.98 (s), 0.99 (s), and 1.12 (s)), and one characteristic Me-15 doublet methyl of cedrane sesquiterpenoid (δH 0.85 (d, 7.2)) [24].…”