A New Sesquiterpene Essential Oil from the Native Andean Species Jungia rugosa Less (Asteraceae): Chemical Analysis, Enantiomeric Evaluation, and Cholinergic Activity

Plant essential oils (PEOs), extracted from many aromatic and medicinal plants, are used in folk medicine and often represent an important part of the traditional pharmacopoeia: they have a long history of use in folk medicine as antimicrobial agents to control several human and phyto-pathogens. Many PEOs have been registered as effective alternatives to chemical and synthetic antimicrobials, and in the last few decades, they have also been effectively used in the food industry as antioxidants and anticarcinogens, thanks to the efforts of many research/medical institutions and pharmaceutical companies. This Special Issue discussed the chemical composition and biological-pharmaceutical activities of some important PEOs and their single constituents. Detailed information has been also covered in this Special Issue regarding the mechanisms, possible modes of action, and factors affecting these activities, such as geographical origins, environmental conditions, nutritional status, and the extraction methods used.

Section: Antimicrobial Phytotoxic Activity and Agri-food Applicationsmentioning

confidence: 99%

Plant Essential Oil with Biological Activity

Elshafie

2022

“…For this reason, our group has been investigating the phytochemistry of the Ecuadorian flora for more than 20 years, by describing the major metabolites of unprecedented botanical species [ 4 , 5 , 6 , 7 , 8 , 9 ]. Together with nonvolatile compounds, we are very interested in essential oils (EOs), defined by the European Pharmacopoeia as “odorous products, usually of complex composition, obtained from a botanically defined plant raw material by steam distillation, dry distillation, or a suitable mechanical process without heating” [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ]. Our interest in the EOs derives from the commercial importance of these mixtures and, overall, from the fact that they can be sources of new or rare sesquiterpenoids, often biologically active, together with enantiomeric compounds.…”

Section: Introductionmentioning

confidence: 99%

A New Essential Oil from the Leaves of Gynoxys rugulosa Muschl. (Asteraceae) Growing in Southern Ecuador: Chemical and Enantioselective Analyses

Maldonado

Malagón

Cumbicus

et al. 2023

Self Cite

An essential oil, distilled from the leaves of the Andean species Gynoxys rugulosa Muschl., is described in the present study for the first time. The chemical composition was qualitatively and quantitatively determined by GC–MS and GC–FID, respectively. On the one hand, the qualitative composition was obtained by comparing the mass spectrum and the linear retention index of each component with data from literature. On the other hand, the quantitative composition was determined by calculating the relative response factor of each constituent, according to its combustion enthalpy. Both analyses were carried out with two orthogonal columns of nonpolar and polar stationary phases. A total of 112 compounds were detected and quantified with at least one column, corresponding to 87.3–93.0% of the whole oil mass. Among the 112 detected components, 103 were identified. The main constituents were α-pinene (5.3–6.0%), (E)-β-caryophyllene (2.4–2.8%), α-humulene (3.0–3.2%), germacrene D (4.9–6.5%), δ-cadinene (2.2–2.3%), caryophyllene oxide (1.6–2.2%), α-cadinol (3.8–4.4%), 1-nonadecanol (1.7–1.9%), 1-eicosanol (0.9–1.2%), n-tricosane (3.3–3.4%), 1-heneicosanol (4.5–5.8%), n-pentacosane (5.8–7.1%), 1-tricosanol (4.0–4.5%), and n-heptacosane (3.0–3.5%). Furthermore, an enantioselective analysis was carried out on the essential oil, by means of two cyclodextrin-based capillary columns. The enantiomers of α-pinene, β-pinene, sabinene, α-phellandrene, β-phellandrene, linalool, α-copaene, terpinen-4-ol, α-terpineol, and germacrene D were detected, and the respective enantiomeric excess was calculated.

“…Essential oils (EOs) are defined by the European Pharmacopoeia as “odorous products, usually of complex composition, obtained from a botanically defined plant raw material by steam-distillation, dry distillation, or a suitable mechanical process without heating” [ 1 ]. Since these products present a wide range of applications and biological activities, together with a great commercial interest, our group is currently engaged in the study of volatile fractions from plants [ 2 , 3 , 4 , 5 , 6 , 7 , 8 ]. In particular, we are interested in EOs characterized by the presence of abundant sesquiterpene fractions, possibly dominated by new or rare sesquiterpenes.…”

Section: Introductionmentioning

confidence: 99%

The Leaf Essential Oil of Gynoxys buxifolia (Kunth) Cass. (Asteraceae): A Good Source of Furanoeremophilane and Bakkenolide A

Cumbicus

Malagón

Cumbicus

et al. 2023

Self Cite

The present study describes the chemical and enantiomeric composition of a new essential oil, distilled from the dry leaves of Gynoxys buxifolia (Kunth) Cass. The chemical analysis was conducted by GC-MS and GC-FID, on two orthogonal capillary columns. A total of 72 compounds were detected and quantified with at least one column, corresponding to about 85% by weight of the whole oil mass. Of the 72 components, 70 were identified by comparing the respective linear retention indices and mass spectra with data from the literature, whereas the two main constituents were identified by preparative purification and NMR experiments. The quantitative analysis was carried out calculating the relative response factor of each compound according to their combustion enthalpy. The major constituents of the EO (≥3%) were: furanoeremophilane (31.3–28.3%), bakkenolide A (17.6–16.3%), caryophyllene oxide (6.0–5.8%), and (E)-β-caryophyllene (4.4%). Additionally, the hydrolate was also analyzed with respect to the dissolved organic phase. About 40.7–43.4 mg/100 mL of organic compounds was detected in solution, of which p-vinylguaiacol was the main component (25.4–29.9 mg/100 mL). Finally, the enantioselective analysis of some chiral terpenes was carried out, with a capillary column based on β-cyclodextrin chiral stationary phase. In this analysis, (1S,5S)-(−)-α-pinene, (1S,5S)-(−)-β-pinene, (S)-(+)-α-phellandrene, (S)-(+)-β-phellandrene, and (S)-(−)-terpinen-4-ol were detected as enantiomerically pure, whereas (S)-(−)-sabinene showed an enantiomeric excess of 69.2%. The essential oil described in the present study is a good source of two uncommon volatile compounds: furanoeremophilane and bakkenolide A. The former lacks bioactivity information and deserves further investigation, whereas the latter is a promising selective anticancer product.