Essential oils and their constituents. XLII. Isomerization of epoxides on active alumina

1968 ◽  
Vol 46 (11) ◽  
pp. 1944-1947 ◽  
Author(s):  
Ishwar C. Nigam ◽  
Leo Levi
Keyword(s):  
Essential Oils ◽  
Perillyl Alcohol ◽  
Side Reactions ◽  
Caryophyllene Oxide ◽  
Campholenic Aldehyde ◽  
Unsaturated Alcohols ◽  
Active Alumina ◽  
Limonene Oxide ◽  
Cis And Trans

When chromatographed on active alumina, epoxides isomerize yielding chiefly the corresponding α,β-unsaturated alcohols. Side reactions were observed in some cases. Limonene oxide yielded cis-1 (7), 8 p-menthadien-ol-2, cis- and trans-carveol, perillyl alcohol, trans-8p-menthene-diol-1,2, and cis- and trans-dihydrocarvone. α-Pinene oxide was converted to pinocarveol, cis- and trans-pinocamphone, campholenic aldehyde and an unidentified alcohol. Caryophyllene oxide yielded three isomeric unsaturated alcohols which were converted to a ketone of known structure.

ESSENTIAL OILS AND THEIR CONSTITUENTS: XXVII. COMPOSITION OF OIL OF GINGERGRASS

1965 ◽  
Vol 43 (2) ◽  
pp. 521-525 ◽  
Author(s):  
M. C. Nigam ◽  
Ishwar C. Nigam ◽  
Leo Levi
Keyword(s):  
Essential Oil ◽  
Essential Oils ◽  
Aromatic Compound ◽  
Limonene Oxide ◽  
Cis And Trans

Oil of gingergrass was found to contain the following as yet unreported constituents: trans-p-menthene-8-diol-1,2; cis- and trans-carveol; cis- and trans-dihydrocarvone; piperitenone and limonene oxide. The presence of an aromatic compound for which gas chromatographic and infrared criteria of identity were determined was also demonstrated. Limonene oxide is probably the most important precursor of these and related monoterpenoids of the essential oil.

Essential oils and their constituents. XLII. Isomerization of epoxides on active alumina

1968 ◽  
Vol 46 (21) ◽  
pp. 3419-3419 ◽  
Author(s):  
Ishwar C. Nigam ◽  
Leo Levi
Keyword(s):  
Essential Oils ◽  
Active Alumina

not available

ANTIOXIDANT AND ANTITYROSINASE ACTIVITIES OF PIPER MAINGAYI HK. ESSENTIAL OILS

2015 ◽  
Vol 78 (1) ◽  
Author(s):  
Nur Athirah Hashim ◽  
Farediah Ahmad ◽  
Deny Susanti
Keyword(s):  
Essential Oils ◽  
Chemical Components ◽  
Caryophyllene Oxide ◽  
Volatile Oils ◽  
Ms Analysis ◽  
Sesquiterpene Hydrocarbons ◽  
Fruit Oil

The study was aimed to investigate the chemical components of stem and fruit volatile oils of Piper. maingayi Hk. with their antioxidant and antityrosinase activities. GC and GC-MS analysis of the essential oils obtained from the fresh stem and fruit of P. maingayi Hk. resulted in the identification of 34 and 18 components accounting for 83.6% and 78.7% of the total amount, respectively. Sesquiterpene hydrocarbons and oxygenated sesquiterpenes were the most highly represented classes as the former ranging from 64.7% to 70.7%, and the latter varying from 7.4% to 8.6%. The main constituents of the stem oil were: β-caryophyllene (26.2%), a-cedrene (8.4%), caryophyllene oxide (6.7%) and cis-calamenene (6.2%), while the fruit oil was dominated by δ-cadinene (22.6%), β-caryophyllene (18.8%), a-copaene (11.2%) and a-cadinol (7.1%). The stem and fruit of P. maingayi oils showed significant value for antioxidant and antityrosinase activities. 

scholarly journals Immunomodulation and Antioxidant Activities as Possible Trypanocidal and Cardioprotective Mechanisms of Major Terpenes from Lippia alba Essential Oils in an Experimental Model of Chronic Chagas Disease

Antioxidants ◽  
2021 ◽  
Vol 10 (11) ◽  
pp. 1851
Author(s):  
Denerieth Ximena Espinel-Mesa ◽  
Clara Isabel González Rugeles ◽  
Julio César Mantilla Hernández ◽  
Elena E. Stashenko ◽  
Carlos Andrés Villegas-Lanau ◽  
...  
Keyword(s):  
Essential Oils ◽  
Chagas Disease ◽  
Antioxidant Activities ◽  
Combined Therapy ◽  
Late Phase ◽  
Immunomodulatory Activity ◽  
Caryophyllene Oxide ◽  
Cardiac Damage ◽  
Lippia Alba ◽  
Chronic Chagas Disease

In the late phase of Trypanosoma cruzi infection, parasite persistence and an exaggerated immune response accompanied by oxidative stress play a crucial role in the genesis of Chronic Chagasic Cardiomyopathy (CCC). Current treatments (Benznidazole (BNZ) and Nifurtimox) can effect only the elimination of the parasite, but are ineffective for late stage treatment and for preventing heart damage and disease progression. In vivo trypanocidal and cardioprotective activity has been reported for Lippia alba essential oils (EOs), ascribed to their two major terpenes, limonene and caryophyllene oxide. To investigate the role of antioxidant and immunomodulatory mechanisms behind these properties, chronic-T. cruzi-infected rats were treated with oral synergistic mixtures of the aforementioned EOs. For this purpose, the EOs were optimized through limonene-enrichment fractioning and by the addition of exogenous caryophyllene oxide (LIMOX) and used alone or in combined therapy with subtherapeutic doses of BNZ (LIMOXBNZ). Clinical, toxicity, inflammatory, oxidative, and parasitological (qPCR) parameters were assessed in cardiac tissue. These therapies demonstrated meaningful antioxidant and immunomodulatory activity on markers involved in CCC pathogenesis (IFN-γ, TNF-α, IL-4, IL-10, and iNOS), which could explain their significant trypanocidal properties and their noteworthy role in preventing, and even reversing, the progression of cardiac damage in chronic Chagas disease.

scholarly journals Essential Oils of Alpinia Rafflesiana and Their Antimicrobial Activities

2013 ◽  
Vol 8 (9) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Shariha Jusoh ◽  
Hasnah Mohd Sirat ◽  
Farediah Ahmad
Keyword(s):  
Essential Oils ◽  
Antimicrobial Activities ◽  
Caryophyllene Oxide ◽  
Capillary Gc ◽  
E Coli ◽  
Leaf Oil ◽  
Main Components ◽  
Fruit Oil ◽  
Antimicrobial Assay

The essential oils from the leaves, pseudostems, rhizomes and fruits of Alpinia rafflesiana were isolated by hydrodistillation. The oils were analysed by capillary GC and GC-MS. The most abundant components in the leaf oil were trans-caryophyllene (32.61%), caryophyllene oxide (8.67%), (2 E,6 Z)-farnesol (4.91%) and α-terpineol (4.25%), while 1,8-cineole (32.25%), myrcene (13.63%), α-terpineol (9.90%) and trans-caryophyllene (9.80%) were the main constituents in the pseudostem oil. The rhizome constituted of tetracosane (42.61%), τ-cadinol (7.46%), α-terpineol (6.71%) were the major components, whereas tetracosane (13.39%), (2 E,6 E)-farnesol (7.31%), α-terpineol (8.51%) and caryophyllene oxide (8.05%) were the main components in the fruit oil. Antimicrobial assay revealed that all the essential oils showed moderate to weak inhibition against the tested microorganisms. The leaf oil was the most active and inhibited both S. aureus and E. coli with MIC values of 7.81 μg/mL and 15.6 μg/mL, respectively.

scholarly journals Development and Validation of a Reversed Phase High Performance Liquid Chromatography-Photodiode Array Detection Method for Simultaneous Identification and Quantification of Coumarin, Precocene-I, β-Caryophyllene Oxide, α-Humulene, and β-Caryophyllene in Ageratum Conyzoides Extracts and Essential Oils from Plants

2020 ◽  
Vol 103 (3) ◽  
pp. 857-864
Author(s):  
Sonal Shah ◽  
Tushar Dhanani ◽  
Sonu Sharma ◽  
Raghuraj Singh ◽  
Satyanshu Kumar ◽  
...  
Keyword(s):  
Essential Oils ◽  
Detection Method ◽  
Reversed Phase ◽  
Caryophyllene Oxide ◽  
Ageratum Conyzoides ◽  
Photodiode Array Detection ◽  
Photodiode Array ◽  
Development And Validation ◽  
Simultaneous Identification ◽  
Identification And Quantification

Abstract Background Ageratum conyzoides is an aromatic plant. It is considered as an invasive and cosmopolite weed, widely spread in tropical and subtropical regions. Phytochemicals such as benzopyrenes, flavonoids, and terpenoids are reported from A. conyzoides. Objective Development and validation of a reversed-phase HPLC-photodiode array (PDA) detection method for simultaneous identification and quantification of coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene in extracts of A. conyzoides and essential oils was carried out. Methods Separation of analytes was achieved on a RP-18 (250 mm × 4.6 mm, 5 µm) column using a solvent system comprising of a mixture of acetonitrile and water with 0.05% trifluoroacetic acid in gradient elution mode at ambient temperature with flow rate of 1 mL/min. Results The retention time of coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene was 4.38, 12.86, 20.10, 33.34, and 35.11 min, respectively. Limits of detection for coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene were 2.5, 2.5, 2.5, 0.025, and 2.5 µg/mL, respectively. Similarly, LOQ were 10, 10, 10, 0.10, and 10 µg/mL for coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β- caryophyllene, respectively. Repeatabilities (RSD, %) values for intraday and interday precision for coumarin, precocene-I, β-caryophyllene oxide, α-humulene, and β-caryophyllene was 0.765–2.086 and 0.886–2.128; 0.879–1.672 and 0.979–1.825; 0.696–2.418 and 0.768–2.592; 1.728–2.362 and 1.965–2.378; 1.615–2.897 and 1.658–2.906, respectively. Conclusions The separation of five analytes was achieved within 50 min. The developed and validated HPLC-PDA method was successfully applied for identification and quantification of above five analytes in A. conyzoides extracts and essential oils. The method could be used for meeting the characterization criteria of phytoformulations.

scholarly journals Caryophyllene Oxide-rich Essential Oils of Lithuanian Artemisia campestris ssp. campestris and Their Toxicity

2010 ◽  
Vol 5 (12) ◽  
pp. 1934578X1000501 ◽  
Author(s):  
Asta Judzentiene ◽  
Jurga Budiene ◽  
Rita Butkiene ◽  
Eugenija Kupcinskiene ◽  
Isabelle Laffont-Schwob ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Essential Oils ◽  
Brine Shrimp ◽  
Caryophyllene Oxide ◽  
Aerial Parts ◽  
Exposure Data ◽  
Germacrene D ◽  
Artemisia Campestris

The chemical composition of the essential oils of aerial parts of Artemisia campestris ssp. campestris, collected from ten different locations in Lithuania is detailed in this paper. The major component in all the oils was caryophyllene oxide (8.5-38.8%), whereas compounds with the caryophyllane skeleton ranged from 10.2 to 44.5%. Other representative constituents were germacrene D (≤15.0%), humulene epoxide II (≤8.1%), β-ylangene (≤7.7%), spathulenol (≤6.8%), β-elemene (≤6.8%), β-caryophyllene (≤6.2%), junenol (≤6.1%) and α- or β-pinene (≤5.5%). Eighty-seven compounds were identified, comprising 73.6-92.3% of the oils. The chemical composition was highly variable depending on the sample location. Toxicity of A. campestris oils was determined using the brine shrimp (Artemia sp.) assay. LC50 values ranging to 20 μg/mL were obtained for three of the oils after 24 hours of exposure. Data of this test revealed that A. campestris ssp. campestris essential oils with dominant caryophyllene oxide are notably toxic.

scholarly journals Chemical composition of essential oil extracted from leaves of Campomanesia adamantium subjected to different hydrodistillation times

2017 ◽  
Vol 47 (1) ◽  
Author(s):  
Juliana Dantas de Oliveira ◽  
Daniely Karen Matias Alves ◽  
Mayker Lazaro Dantas Miranda ◽  
José Milton Alves ◽  
Marcelo Nogueira Xavier ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Essential Oil ◽  
Essential Oils ◽  
Oil Content ◽  
Chemical Constituents ◽  
Caryophyllene Oxide ◽  
Fruit Species ◽  
Randomized Design ◽  
Completely Randomized Design

ABSTRACT: Campomanesia adamantium is a native fruit species of the Cerrado and is used in food and medicines and as bee pasture. The chemical composition of essential oils obtained from plants of the same species have varying constituent proportions due to the influence of extractive factors, environmental, genetic and ontogenetic. This study aimed to identify the influence of hydrodistillation time on the content and chemical composition of essential oil extracted from the leaves of C. adamantium . Treatments consisted of five extraction times (1, 2, 3, 4, and 5h) using Clevenger with five replications in a completely randomized design. It was observed that after two hours of hydrodistillation, the essential oil content remains constant. Regarding the chemical constituents of essential oil, variation of the proportions of the compounds tested occurred at all hydrodistillation times. The compounds spathulenol oxygenated sesquiterpenes and caryophyllene oxide were the majority in the five hydrodistillation times.

scholarly journals Chemical Composition of the Essential Oils of Centaurea Sicana and C. Giardinae Growing Wild in Sicily

2008 ◽  
Vol 3 (6) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Carmen Formisano ◽  
Daniela Rigano ◽  
Felice Senatore ◽  
Maurizio Bruno ◽  
Sergio Rosselli ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Essential Oils ◽  
Caryophyllene Oxide ◽  
Germacrene D ◽  
Total Oil

The essential oils of Centaurea sicana (S) and C. giardinae (G) were studied by GC and GC-MS. Thirty constituents for S, representing 81.5% of the total oil, and 24 compounds for G (94.2% of the total) were identified. The oils were rich in sesquiterpenoids (47.9% for S and 54.7% for G) and hydrocarbons (25.9% for S and 31.7% for G). Germacrene D (13.3%), ( E)-β-farnesene (8.3%), nonacosane (7.3%), heptacosane (6.5%) and phytol (6%) were recognized as the main constituents for S, while caryophyllene oxide (17.7%), nonacosane (14.5%), germacrene D (11.5%), caryophyllene (11.2%) and heptacosane (10.3%) were the main compounds for G.

scholarly journals Constituents and Anthelmintic Activity Evaluation of Albizia Adiantifolia (Schumach) W.F. Wright Essential Oils FromNigeria

2018 ◽  
Vol 10 (2) ◽  
pp. 10 ◽  
Author(s):  
Akinsola Akande ◽  
Sherifat Aboaba ◽  
Guido Flamini
Keyword(s):  
Gas Chromatography ◽  
Essential Oils ◽  
Anthelmintic Activity ◽  
Stem Bark ◽  
Mass Spectrometry Analysis ◽  
Gas Chromatography Mass Spectrometry ◽  
Root Bark ◽  
Dependent Manner ◽  
Caryophyllene Oxide ◽  
Significant Difference

Albizia adiantifolia (Schumach) W.F. Wright (Fabaceae) is a plant used traditionally in treating different health ailments which includes worm infections. The essential oils (EOs) were obtained by hydrodistillation in an all glass Clevenger apparatus, and characterized by gas chromatography (GC) and gas chromatography-mass spectrometry analysis (GC-MS). In vitro petri-dish anthelmintic activity was carried out using adult earthworm, Eudrilus eugeniae. The leaves, stem bark and root bark EOs afforded a total of 40, 26 and 20 constituents representing 90.9%, 94.1% and 90.9% of the total oil fractions respectively. The classes of compounds identified in the leaves, stem bark and root bark are oxygenated monoterpenes (4.1%, 1.7% and 4.0% respectively), sesquiterpene hydrocarbons (39.5%, 67.3% and 42.6% respectively), oxygenated sesquiterpenes (18.7%, 22.3% and 30.1% respectively), non-terpene derivatives (12.1%, 2.6% and 14.2% respectively) and apocarotenoids (16.5% and 0.2% in the leaves and stem-bark). β-caryophyllene (23.0%), E-geranylacetone (7.4%), acorenone (6.4%), viridiflorol (6.4%), α-zingiberene (6.3%) and ar-curcumene (4.6%) were the major constituents in the leaves oil, β-caryophyllene (39.3%), selin-11-en-4-α-ol (10.4%), α-zingiberene (9.6%), ar-curcumene (7.2%), caryophyllene oxide (6.4%) and α-humulene (5.6%) were the major constituents in the stem bark oil, while β-caryophyllene (32.1%), selin-11-en-4-α-ol (13.1%), caryophyllene oxide (8.4%), pentadecanal (6.1%) and α -humulene (4.4%) were the major constituents in the root bark oil. β -caryophyllene dominated the oils. The leaf EO was the most active against E. eugeniae worm. All the oils showed a relatively higher activity compared to Albendazole, in a concentration dependent manner. There was significant difference (p<0.001) in activity.

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