Carnosol from Lepechinia mutica and tiliroside from Vallea stipularis: Two promising inhibitors of BuChE

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In this research, the leaves of Lepechinia heteromorpha (Briq.) Epling, Lepechinia radula (Benth.) Epling and Lepechinia paniculata (Kunth) Epling have been collected in order to perform a phytochemical study. The first species was distilled to obtain a novel essential oil (EO), while the others were submitted to ethyl acetate extraction and secondary metabolite isolation. The chemical composition of the EO from L. heteromorpha has been investigated by Gas Chromatography-Mass Spectrometry (GC-MS) and Gas Chromatography with Retention Indices (GC(RI)), identifying 25 constituents. A major compound, (−)-ledol (21.2%), and a minor compound, (−)-caryophyllene oxide (1.0%), were isolated from the EO and their structures confirmed by Nuclear Magnetic Resonance (NMR) spectroscopy. Other major constituents of the EO were viridiflorene (27.3%), (E,E)-α-farnesene (1.4%), spirolepechinene and (E)-β-caryophyllene (7.1% each), allo-aromadendrene (6.1%), camphor (1.7%), limonene (1.3%) and β-phellandrene (4.6%). The enantiomeric composition of the EO monoterpene fraction was also studied, determining the enantiomeric excess and distribution of α-pinene, limonene, β-phellandrene and camphor. The ethyl acetate extract of L. radula and L. paniculata were fractionated by column chromatography. Spathulenol, angustanoic acid E and 5-hydroxy-4′,7-dimethoxy flavone were isolated from L. radula extract; ledol, guaiol and (−)-carnosol were found in L. paniculata.

Section: Discussionmentioning

confidence: 99%

Phytochemistry of Three Ecuadorian Lamiaceae: Lepechinia heteromorpha (Briq.) Epling, Lepechinia radula (Benth.) Epling and Lepechinia paniculata (Kunth) Epling

Gilardoni

Ramírez

Montalván

et al. 2018

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“…Alzheimer’s disease (AD) is a chronic neurodegenerative illness characterized by a progressive deterioration of memory and other cognitive functions and is currently the focus of scientific research aimed at finding effective therapeutic strategies, mainly related to the inhibition of the enzymes acetylcholinesterase and butyrylcholinesterase, known as cholinesterases (ChEs). These enzymes are involved in the development of the disease, since they catalyze the degradation of the neurotransmitter acetylcholine (ACh) [12]. As summarized in the 2016 World Alzheimer’s Report, 47 million people live with dementia worldwide, and it is estimated that this number will increase to more than 131 million by the year 2050.…”

Section: Introductionmentioning

confidence: 99%

Chemical, Enantioselective, and Sensory Analysis of a Cholinesterase Inhibitor Essential Oil from Coreopsis triloba S.F. Blake (Asteraceae)

Espinosa

Bec

Larroque

et al. 2019

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The fresh leaves of Coreopsis triloba S.F. Blake, collected at Cerro Villonaco in Loja, Ecuador, were investigated with respect to their essential oil (EO). The chemical composition was determined qualitatively through gas chromatography coupled with mass spectrometry (GC-MS) and quantitatively by gas chromatography coupled with flame ionization (GC-FID), using relative response factors (RRF) based on the enthalpy of combustion. The essential oil contained between 92.5% and 93.4% of monoterpene hydrocarbons, with (E)-β-ocimene being the main component (35.2–35.9%), followed by β-phellandrene (24.6–25.0%), α-pinene (15.3–15.9%), myrcene (10.9–11.0%), sabinene (2.2–2.4%), (Z)-β-ocimene (1.5%), and germacrene D (1.2–1.3%). The enantiomeric distribution of α-pinene, β-pinene, limonene, and germacrene D was also determined. The main components responsible for the aroma were identified through aroma extract dilution analysis (AEDA), a gas chromatography-olfactometry (GC-O) based technique, being α-pinene, β-pinene (0.6%), terpinolene (0.1%), α-copaene (0.1–0.3%), β-phellandrene, and (E)-4,8-dimethyl-1,3,7-nonatriene (0.1–0.2%) the main olfactory constituents according to the decreasing factor of dilution (FD) order. The biological tests showed IC50 inhibition values of 42.2 and 6.8 µg/mL for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), respectively.

“…As part of a project aiming to valorize Ecuadorian spontaneous flora [8,9,10,11,12,13,14,15,16,17,18,19,20,21,22,23,24,25], the chemical composition and sensory profile of Myrcianthes myrsinoides (Kunth) Grifo and Myrcia mollis (Kunth) DC essential oils (EOs) are here reported for the first time. Gas chromatography mass spectrometry (GC-MS) and enantioselective GC-MS were used for the quali-quantitative analysis, and GC-olfactometry (GC-O) to evaluate the odor active compounds.…”

Section: Introductionmentioning

confidence: 99%

Chemical Composition, Enantiomeric Distribution, and Sensory Evaluation of the Essential Oils Distilled from the Ecuadorian Species Myrcianthes myrsinoides (Kunth) Grifo and Myrcia mollis (Kunth) DC. (Myrtaceae)

Montalván

Peñafiel

Ramírez

et al. 2019

The essential oils of Myrcianthes myrsinoides and Myrcia mollis, belonging to the Myrtaceae family, were obtained by steam distillation. They were analyzed by gas chromatography-mass spectrometry (GC-MS), gas chromatography-flame ionization detector (GC-FID), enantioselective gas chromatography, and gas chromatography-olfactometry (GC-O). A total of 58 compounds for Myrcianthes myrsinoides essential oil (EO) and 22 compounds for Myrcia mollis EO were identified and quantified by GC-MS with apolar and polar columns (including undetermined components). Major compounds (>5.0%) were limonene (5.3%–5.2%), 1,8-cineole (10.4%–11.6%), (Z)-caryophyllene (16.6%–16.8%), trans-calamenene (15.9%–14.6%), and spathulenol (6.2%–6.5%). The enantiomeric excess of eight chiral constituents was determined, being (+)-limonene and (+)-germacrene D enantiomerically pure. Eight components were identified as determinant in the aromatic profile: α-pinene, β-pinene, (+)-limonene, γ-terpinene, terpinolene, linalool, β-elemene and spathulenol. For M. mollis, the major compounds (>5.0%) were α-pinene (29.2%–27.7%), β-pinene (31.3%–30.0%), myrcene (5.0%–5.2%), 1,8-cineole (8.5%–8.7%), and linalool (7.7%–8.2%). The enantiomeric excess of five chiral constituents was determined, with (S)-α-pinene and (+)-germacrene D enantiomerically pure. The metabolites β-pinene, 1,8-cineole, γ-terpinene, terpinolene, linalool, and (E)-β-caryophyllene were mainly responsible for the aroma of the EO. Finally, the M. myrsinoides essential oil has an inhibitory activity for cholinesterase enzymes (IC50 of 78.6 μg/mL and 18.4 μg/mL vs. acethylcholinesterase (AChE) and butyrylcholinesterase (BChE) respectively). This activity is of interest to treat Alzheimer’s disease.