Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils

AbstractIn the present work, an endemic species Prangos heyniae collected in four locations from Turkey was subjected to hydrodistillation in Clevenger type apparatus to obtain the essential oils (EO1-4). The gas-chromatography/mass spectrometry (GC/MS) and gas-chromatography-flame ionization detector (GC/FID) analyses showed that the EOs were rich in sesquiterpenes, germacrene D (10.3-12.1%), β-bisabolene (14.4%), kessane (26.9%), germacrene B (8.2%), elemol (3.4-46.9%), β-bisabolenal (1.4-70.7%), β-bisabolenol (8.4%) and an eudesmane type sesquiterpene (1) (16.1%) with [M+218]. This unidentified compound (1) was isolated in a rapid one-step manner with >95.0% purity using Preparative Capillary Gas Chromatography (PCGC) with an HP Innowax column connected to a Preparative Fraction Collector (PFC) system. Structure determination was accomplished from 1D- and 2D-NMR spectroscopic data which determined a new eudesmane type sesquiterpene, 3,7(11)-eudesmadien-2-one (1). Using a biting deterrent bioassay, the mean proportion not biting (PNB) values of the P. heyniae EO1-4 were 0.88 for EO1 and 0.80 for EO2 which were similar to the positive control DEET (N,N-diethyl-3-methylbenzamide). The EO3 and EO4 had lower PNB values of 0.64 and 0.44, respectively. P. heyniae EO1-4 showed good larvicidal activity at 125 and 62.5 ppm whereas EO1-3 were slightly less effective at the dose of 31.25 ppm and EO4 was not active at 31.25 ppm against 1st instar Aedes aegypti.

Download Full-text

Potential Application of Prunus armeniaca L. and P. domestica L. Leaf Essential Oils as Antioxidant and of Cholinesterases Inhibitors

Antioxidants ◽

10.3390/antiox8010002 ◽

2018 ◽

Vol 8 (1) ◽

pp. 2 ◽

Cited By ~ 5

Author(s):

Marco Bonesi ◽

Maria Tenuta ◽

Monica Loizzo ◽

Vincenzo Sicari ◽

Rosa Tundis

Keyword(s):

Gas Chromatography ◽

Essential Oils ◽

Antioxidant Properties ◽

Positive Control ◽

Prunus Armeniaca ◽

Gas Chromatography Mass Spectrometry ◽

Flame Ionization ◽

Ic50 Values ◽

Comprehensive Comparison

The aim of this work is to investigate the in vitro acetylcholinesterase (AChE) and butyrycholinesterase (BChE) inhibitory activities of essential oils obtained by hydrodistillation from the leaves of Prunus armeniaca and P. domestica in relation to their composition, analysed by Gas Chromatography–Flame Ionization Detector (GC-FID) and Gas Chromatography-Mass Spectrometry (GC-MS) analyses, at different times. Moreover, considering the role of free radicals in the progression of neurodegenerative disorders, the antioxidant properties of essential oils were investigated by using, 2’-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and β-carotene bleaching tests. The relative antioxidant capacity index (RACI) was used to achieve more comprehensive comparison between analysed antioxidant effects of essential oils. P. armeniaca oils were more active than P. domestica oils against AChE. Against BChE, the most active was the essential oil from P. domestica leaves collected in August with an IC50 value of 95.80 μg/mL. This oil exerted the highest inhibitory activity of lipid peroxidation with IC50 values of 11.15 and 11.39 μg/mL after 30 and 60 min of incubation, respectively. All samples demonstrated a remarkable ABTS radicals scavenging activity, with IC50 values in the range 0.45–0.57 μg/mL in comparison to the positive control, ascorbic acid.

Download Full-text

Chemical Composition and Biological Activities of Essential Oils of Pinus patula

Natural Product Communications ◽

10.1177/1934578x1100601031 ◽

2011 ◽

Vol 6 (10) ◽

pp. 1934578X1100601 ◽

Cited By ~ 1

Author(s):

Ismail Amri ◽

Hamrouni Lamia ◽

Samia Gargouri ◽

Mohsen Hanana ◽

Mariem Mahfoudhi ◽

...

Keyword(s):

Gas Chromatography ◽

Essential Oils ◽

Biological Activities ◽

Pathogenic Fungi ◽

Plant Diseases ◽

Gas Chromatography Mass Spectrometry ◽

Pinus Patula ◽

Flame Ionization ◽

Total Oil

Essential oils isolated from needles of Pinus patula by hydrodistillation were analyzed by gas chromatography-flame ionization detection (GC-FID) and gas chromatography mass spectrometry (GC-MS). Thirty-eight compounds were identified, representing 98.3% of the total oil. The oil was rich in monoterpene hydrocarbons (62.4%), particularly α-pinene (35.2%) and β-phellandrene (19.5%). The in vitro antifungal assay showed that P. patula oil significantly inhibited the growth of 9 plant pathogenic fungi. The oil, when tested on Sinapis arvensis, Lolium rigidum, Phalaris canariensis and Trifolium campestre, completely inhibited seed germination and seedling growth of all species. Our preliminary results showed that P. patula essential oil could be valorized for the control of weeds and fungal plant diseases.

Download Full-text

In vitro efficacy of essential oils with different concentrations of 1,8-cineole against Rhipicephalus (Boophilus) microplus

Revista Brasileira de Parasitologia Veterinária ◽

10.1590/s1984-296120180015 ◽

2018 ◽

Vol 27 (2) ◽

pp. 203-210 ◽

Cited By ~ 9

Author(s):

Karina Neoob de Carvalho Castro ◽

Kirley Marques Canuto ◽

Edy de Sousa Brito ◽

Lívio Martins Costa-Júnior ◽

Ivanilza Moreira de Andrade ◽

...

Keyword(s):

Gas Chromatography ◽

Essential Oils ◽

Probit Analysis ◽

Acaricidal Activity ◽

Boophilus Microplus ◽

Gas Chromatography Mass Spectrometry ◽

Flame Ionization Detection ◽

Flame Ionization ◽

Alpinia Zerumbet

Abstract The aim of this study was to evaluate the acaricidal activity of essential oils from three species of plants with intermediary concentrations of 1,8-cineole against the tick species Rhipicephalus (Boophilus) microplus. For this purpose, five serial concentrations (100.0, 50.0, 25.0, 12.5, 6.2 mg/mL) of essential oils from Mesosphaerum suaveolens (L.) Kuntze, Ocimum gratissimum L. and Alpinia zerumbet (Pers.) B. L. Burtt & R. M. Sm. were used on larval packet and adult immersion tests. The essential oils were analysed by gas chromatography-mass spectrometry (GC/MS) and gas chromatography-flame ionization detection (GC-FID), being detected 35.8, 24.7 and 24.0% of 1.8-cineol in the oils of M. suaveolens, O. gratissimum and A. zerumbet, respectively. The lethal concentration (LC 50) of each oil for larvae and engorged females was calculated through Probit analysis. All essential oils showed high efficacy (≥ 95.0%) on engorged females at the 100.0 mg/mL concentration. In regards to larvae, O. gratissimum (LC 50 = 11.9 mg/mL) was the most potent, followed by the A. zerumbet (LC50 = 19.7 mg/mL) and the M. suaveolens (LC50 = 51.6 mg/mL) essential oils. These results show that other compounds interfere with 1,8-cineole action.

Download Full-text

A Novel Chemical Profile of a Selective In Vitro Cholinergic Essential Oil from Clinopodium taxifolium (Kunth) Govaerts (Lamiaceae), a Native Andean Species of Ecuador

Molecules ◽

10.3390/molecules26010045 ◽

2020 ◽

Vol 26 (1) ◽

pp. 45

Author(s):

Sandra Espinosa ◽

Nicole Bec ◽

Christian Larroque ◽

Jorge Ramírez ◽

Barbara Sgorbini ◽

...

Keyword(s):

Gas Chromatography ◽

Essential Oil ◽

Positive Control ◽

Gas Chromatography Mass Spectrometry ◽

Chemical Profile ◽

Flame Ionization ◽

Aerial Parts ◽

Germacrene D ◽

Enantioselective Gc

A novel chemical profile essential oil, distilled from the aerial parts of Clinopodium taxifolium (Kunth) Govaerts (Lamiaceae), was analysed by Gas Chromatography-Mass Spectrometry (GC-MS, qualitative analysis) and Gas Chromatography with Flame Ionization Detector (GC-FID, quantitative analysis), with both polar and non-polar stationary phase columns. The chemical composition mostly consisted of sesquiterpenes and sesquiterpenoids (>70%), the main ones being (E)-β-caryophyllene (17.8%), α-copaene (10.5%), β-bourbonene (9.9%), δ-cadinene (6.6%), cis-cadina-1(6),4-diene (6.4%) and germacrene D (4.9%), with the non-polar column. The essential oil was then submitted to enantioselective GC analysis, with a diethyl-tert-butyldimethylsilyl-β-cyclodextrin diluted in PS-086 chiral selector, resulting in the following enantiomeric excesses for the chiral components: (1R,5S)-(−)-α-thujene (67.8%), (1R,5R)-(+)-α-pinene (85.5%), (1S,5S)-(−)-β-pinene (90.0%), (1S,5S)-(−)-sabinene (12.3%), (S)-(−)-limonene (88.1%), (S)-(+)-linalool (32.7%), (R)-(−)-terpinen-4-ol (9.3%), (S)-(−)-α-terpineol (71.2%) and (S)-(−)-germacrene D (89.0%). The inhibition activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) of C. taxifolium essential oil was then tested, resulting in selective activity against BChE with an IC50 value of 31.3 ± 3.0 μg/mL (positive control: donepezil, IC50 = 3.6 μg/mL).

Download Full-text

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)

Plants ◽

10.3390/plants8110511 ◽

2019 ◽

Vol 8 (11) ◽

pp. 511 ◽

Cited By ~ 2

Author(s):

Montalván ◽

Peñafiel ◽

Ramírez ◽

Cumbicus ◽

Bec ◽

...

Keyword(s):

Gas Chromatography ◽

Essential Oil ◽

Essential Oils ◽

Enantiomeric Excess ◽

Gas Chromatography Mass Spectrometry ◽

Enantiomerically Pure ◽

Flame Ionization ◽

Gas Chromatography Olfactometry ◽

Germacrene D ◽

Enantioselective Gas Chromatography

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.

Download Full-text

Characterization of Essential Oil Components from Aromatic Plants that Grow Wild in the “Piana del Sele” (Salerno, Southern Italy) using Gas Chromatography-Mass Spectrometry

Natural Product Communications ◽

10.1177/1934578x1501000739 ◽

2015 ◽

Vol 10 (7) ◽

pp. 1934578X1501000 ◽

Cited By ~ 2

Author(s):

Daniele Naviglio ◽

Laura Le Grottaglie ◽

Manuela Vitulano ◽

Marco Trifuoggi ◽

Monica Gallo

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Essential Oils ◽

Southern Italy ◽

Gas Chromatography Mass Spectrometry ◽

Thymus Vulgaris ◽

Mentha Spicata ◽

Flame Ionization ◽

Aldehydes And Ketones

Essential oils from Rosmarinus officinalis, Salvia officinalis, Thymus vulgaris, Melissa officinalis and Mentha spicata growing wild in the “Piana del Sele” (Salerno, Southern Italy) have been extracted by hydro-distillation, quantified and characterized by gas chromatography coupled with flame ionization detection (FID) and mass-spectrometry (MS). Sixty-nine compounds were identified and classified according to their chemical classes. The results showed that the composition of the essential oils was extremely variable and specific for each botanical species. Hydrocarbons were the most abundant class in all essential oils except for sage where aldehydes and ketones were the most representative compounds. Only for thyme was a higher content of alcohols found.

Download Full-text

Essential Oils from Fresh Fruits, Fruit Stalks and Stem Barks of Four Piper nigrum Varieties from Sarawak

Borneo Journal of Resource Science and Technology ◽

10.33736/bjrst.255.2013 ◽

1970 ◽

Vol 3 (1) ◽

pp. 43-51 ◽

Cited By ~ 1

Author(s):

Irna Syairina Sahari ◽

Zaini Assim ◽

Fasihuddin Badruddin Ahmad ◽

Ismail Bin Jusoh

Keyword(s):

Gas Chromatography ◽

Essential Oils ◽

Principal Component ◽

Gas Chromatography Mass Spectrometry ◽

Piper Nigrum ◽

Chemical Compositions ◽

Ionization Detector ◽

Flame Ionization ◽

Oil Components ◽

Type Apparatus

The variation of chemical compositions in essential oils obtained from fresh fruits, fruit stalks and stem barks offour Piper nigrum L. varieties was analysed using capillary gas chromatography-flame ionization detector (GCFID)and gas chromatography-mass spectrometry (GC-MS). The essential oils were extracted byhydrodistillation Clevenger-type apparatus. The major oil constituents identified in all samples were β-elemene(1.07-2.93%), (+)-δ-cadinene (0.58-6.20%), α-caryophyllene (1.90-6.21%), δ-elemene (0.38-13.26%), 3-carene(0.07-16.82%) and β-caryophyllene (11.78-38.33%). All oil samples showed high content of sesquiterpenes,whereas fruit oils from Semongok Emas and Semongok Wan yielded mostly monoterpenes. Hierarchicalclustering and principal component analysis (PCA) of the oil components revealed significant correlationamongst individual P. nigrum oil samples.

Download Full-text

Composition and Antimicrobial Activity of Essential Oils from Leaves and Twigs of Magnolia hookeri var. longirostrata D.X.Li & R. Z. Zhou and Magnolia insignis Wall. in Ha Giang Province of Vietnam

Records of Natural Products ◽

10.25135/rnp.212.20.10.1842 ◽

2021 ◽

Vol 15 (3) ◽

pp. 207-212

Author(s):

Ha Thi Thu Chu ◽

Thuy Thi Thu Dinh ◽

Nam Quang Vu ◽

Tam Kieu Bang Nguyen ◽

William N. Setzer

Keyword(s):

Gas Chromatography ◽

Essential Oils ◽

Dry Weight ◽

Gas Chromatography Mass Spectrometry ◽

Ionization Detector ◽

Inhibitory Effects ◽

Flame Ionization ◽

Leaf Oil ◽

First Time ◽

Time Information

The essential oils from leaves and twigs of Magnolia hookeri var. longirostrata D.X.Li & R.Z.Zhou and Magnolia insignis Wall., growing wild in Ha Giang Province of Vietnam, were obtained by hydrodistillation and analyzed by gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). The respective yields of the M. hookeri var. longirostrata leaf and twig oils were 0.14% and 0.05% (v/w), and of the M. insignis leaf and twig oils were 0.16% and 0.05% (v/w), calculated on a dry weight basis. Major components of the oils of M. hookeri var. longirostrata were: Linalool (21.3%), (E)-nerolidol (12.2%) and neo-intermedeol (13.5%) (leaf oil); 1,8-cineole (13.3%) and linalool (17.1%) (twig oil). Major components of the oils of M. insignis were: Linalool (24.1%), geraniol (14.9%) and (E)-nerolidol (22.5%) (leaf oil); 1,8-cineole (9.5%) and linalool (26.9%) (twig oil). The essential oils from M. insignis showed stronger inhibitory effects on the seven test microorganisms than those from M. hookeri var. longirostrata. Candida albicans and Lactobacillus fermentum were more sensitive to the essential oils than the other tested microorganisms. This is the first time information on essential oils of M. hookeri var. longirostrata leaves and twigs and of M. insignis twigs are reported.

Download Full-text

Characterization of Nepeta viscida, N. nuda subsp. nuda and the Putative Hybrid N. × tmolea Essential Oils

Records of Natural Products ◽

10.25135/rnp.250.21.04.2033 ◽

2021 ◽

Vol 15 (5) ◽

pp. 388-395

Author(s):

Sema Çarıkçı

Keyword(s):

Gas Chromatography ◽

Essential Oils ◽

Gas Chromatography Mass Spectrometry ◽

Putative Hybrid ◽

Ionization Detector ◽

Natural Habitats ◽

Flame Ionization ◽

Aerial Parts ◽

Main Components

Nepeta viscida, N. nuda subsp. nuda, and their putative hybrid N. × tmolea were evaluated for their essential oils with chemotaxonomical aspect. Hybrid of N. x tmolea individuals were observed in the regions where the distribution of N. viscida and N. nuda subsp. nuda taxa were present, namely Dursunbey (Balıkesir) and Ödemiş (İzmir) natural habitats, respectively. The aerial parts of the taxa were hydrodistilled for 4 h using a Clevenger-type apparatus. The essential oils were analyzed both by gas chromatography-mass spectrometry (GC/MS) and gas chromatography flame ionization detector (GC-FID). The main components of the oils for the species collected were spathulenol, β-elemene, and 1,8-cineole, supporting the hybridization proposition.

Download Full-text

Chemical Composition and Broad-Spectrum Insecticidal Activity of the Flower Essential Oil from an Ancient Sicilian Food Plant, Ridolfia segetum

Agriculture ◽

10.3390/agriculture11040304 ◽

2021 ◽

Vol 11 (4) ◽

pp. 304

Author(s):

Natale Badalamenti ◽

Vincenzo Ilardi ◽

Maurizio Bruno ◽

Roman Pavela ◽

Maria C. Boukouvala ◽

...

Keyword(s):

Gas Chromatography ◽

Essential Oil ◽

Essential Oils ◽

Food Plant ◽

Gas Chromatography Mass Spectrometry ◽

Flame Ionization Detection ◽

Flame Ionization ◽

The Family ◽

Human Poisoning ◽

Careful Assessment

Several species of the family Apiaceae are aromatic herbs that produce essential oils usable on an industrial scale for pharmaceutical, cosmetic, and food purposes. In particular, some essential oils, such as green insecticides for example, may replace synthetic insecticides, keeping most of their efficacy and avoiding environmental pollution or human poisoning. In the present study, we explored the insecticidal potential of Ridolfia segetum (L.) Moris essential oil (EO) against three different pests: Culex quinquefasciatus Say, Musca domestica L., and Spodoptera littoralis (Boisduval). For this purpose, the EO was obtained by hydrodistillation of flowers and its composition was achieved by gas chromatography/flame ionization detection (GC/FID) and gas chromatography/mass spectrometry (GC/MS). This EO was rich in α-phellandrene (49.3%), β-phellandrene (9.2%), terpinolene (20.7%), and piperitenone oxide (5.9%). Concerning the mosquitocidal efficacy, the EO showed noteworthy toxicity against C. quinquefasciatus 3rd instar larvae, with a LC50 = 27.1 µL L−1 and LC90 = 42.5 µL L−1. Regarding M. domestica, a different toxicity of the R. segetum EO was found on male and female flies, calculating LD50 values of 10.5 and 50.8 µg adult−1, respectively. The EO was also toxic to S. littoralis 3rd instar larvae, achieving LD50 and LD90 values of 37.9 and 99.6 µg larva−1, respectively. Overall, this flower EO, extracted from a traditional Sicilian food plant, merits further investigation for the development of green insecticide formulations to be used in real world conditions, pending a careful assessment of non-target toxicity on beneficial organisms.

Download Full-text