Sesquiterpenes from Cupressus macrocarpa foliage

Abstract

Ten sesquiterpenes, many with unusual carbon skeletons, were identified in foliage of Cupressus macrocarpa. These are (-)-10-epi-beta-acoradiene; ent-widdra-2,4(14)-diene; (E)-iso-gamma-bisabolene, i.e., (4E)-4-(1,5-dimethylhex-5-enylidene)-1-methylcyclohexene; (-)-cumacrene, i.e., (4S)-4-[(1R,2S)-2-isopropenyl-1-methylcyclobutyl]-1-methylcyclohexene; (-)-alpha-chamipinene, i.e., (1S,6S,7S)-2,2,6,8-tetramethyltricyclo[5.3.1.01,6]undec-8-ene; and five sesquiterpenes with a 3,3,4'-trimethyl-1,1'-bi(cyclohexyl) skeleton for which the trivial name macrocarpane is proposed. The possible single-enzyme biogenesis of these sesquiterpenes is discussed.

Essential Oil Variability in Natural Hahadjerine Population of Cupressus dupreziana in Tassili Ajjer (Algeria)

“…(Figure 2). The compounds found in the Hahadjerine cypress generally resembled those previously reported to occur in some of cypress species [22][23][24][25]. In particular, α-pinene and Δ…”

Novel Acidic Sesquiterpenoids Constitute a Dominant Class of Pathogen-Induced Phytoalexins in Maize

“…NMR spectra were processed using Topspin 2.0 (Bruker Corporation) and MestReNova (MestreLab Research) software packages. The numbering of the zealexin carbon atoms refers to that previously described for b-macrocarpene (Cool, 2005 (Cool, 2005) except at C15 (carboxylic acid) and nearby carbons at C4, C3, and C5 (Supplemental Table S1). The correlation spectroscopy, HMBC, and NOESY data are also in agreement with the b-macrocarpene core structure and the presence of a carboxylic acid at C15.…”

“…To identify these compounds, a large-scale purification of fungal-infected tissue was performed and resulted in isolation of the four most abundant sesquiterpenoids (analytes 5, 6, 10, and 11). Structural elucidation via NMR (Supplemental Tables S1-S4) revealed that all four were closely related to 4#,5,5-trimethyl-1,1#-bi(cyclohexane)-1,3#-diene, termed b-macrocarpene, from which we used the previously assigned NMR numbering scheme of carbon atoms (Cool, 2005). We term the C15 carboxylic acid of b-macrocarpene zealexin A1 (Fig.…”

Chemical Composition and Antimicrobial Activity of the Essential Oil of the Leaves of Cupressus macrocarpa Hartweg. ex Gordon

“…ex Gordon) as a medicinal plant belongs to the family Cupressaceae and commonly known as Monterey Cypress (Cool, 2005;Thukral et al, 2014). It is widely distributed throughout the tropical and temperate regions around the world i.e., Mexico, North America Asia, and North Africa (El-Ghorab et al, 2007).…”

“…C. macrocarpa was used traditionally for decades for the treatment of various ailments, e.g., styptic problem, eliminates fluid retention, whooping cough and rheumatism (Thukral et al, 2014). C. macrocarpa received little concern regarding its phytochemical constituents; Cool (2005) reported the isolation of ten sesquiterpenes from its foliage. Furthermore, Al-Sayed and AbdelDaim (2014) investigated the protective role of the isolated cupressuflavone from C. macrocarpa against CCl 4 induced hepatoand nephrotoxicity in mice.…”