Structural Elucidation and Cytotoxicity of a New 17-Membered Ring Lactone from Algerian Eryngium campestre

The chemical composition of a hexanic extract of Eryngium campestre, obtained from its aerial parts, was investigated by GC-FID, GC/MS, HRMS, NMR and VCD analyses. The main compounds were germacrene D (23.6%), eudesma-4(15)-7-dien-1-β-ol (8.2%) and falcarindiol (9.4%), which are associated with a new uncommon and naturally found 17-membered ring lactone. This 17-membered ring features conjugated acetylenic bonds, named campestrolide (23.0%). The crude extract showed moderate antitrypanosomal (Trypanosoma brucei brucei), antileishmanial (Leishmania mexicana mexicana) and anticancer (cancerous macrophage-like murine cells) activities, and also displayed cytotoxicity, (human normal fibroblasts) in similar concentration ranges (IC50 = 3.0, 3.9, 4.0 and 4.4 µg/mL respectively). Likewise, campestrolide displayed low activity on all tested cells (IC50: 12.5–19.5 µM) except on Trypanosoma, on which it was very active and moderately selective (IC50 = 2.2 µM. SI= 8.9). In conclusion, the new compound that has been described, displaying a singular structure, possesses interesting antitrypanosomal activity that should be further investigated and improved.

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In vitro Antileishmanial, Antitrypanosomal, and Anti-inflammatory-like Activity of Terminalia mollis Root Bark

Planta Medica ◽

10.1055/a-1260-6382 ◽

2020 ◽

Author(s):

Raymond Muganga ◽

Joanne Bero ◽

Joëlle Quetin-Leclercq ◽

Luc Angenot ◽

Monique Tits ◽

...

Keyword(s):

Trypanosoma Brucei ◽

Crude Extract ◽

Root Bark ◽

Myeloperoxidase Activity ◽

Leishmania Mexicana ◽

Trypanosoma Brucei Brucei ◽

Crude Extracts ◽

Anti Inflammatory ◽

Enzymatic Detection

AbstractThis study aims at determining the in vitro antitrypanosomal, antileishmanial, antioxidant, and anti-inflammatory-like activities of Terminalia mollis root crude extracts. The antitrypanosomal and antileishmanial activities on Trypanosoma brucei brucei (strain 427) and promastigotes of Leishmania mexicana mexicana (MHOM/BZ/84/BEL46) were evaluated in vitro. The methanolic root bark extract and standards were profiled by HPLC-PDA, and the majority of compounds identified using literature data. The in vitro antioxidant and anti-inflammatory-like activities were determined by evaluating the effect of crude extracts on reactive oxygen species produced by phorbol 12-myristate 13-acetate-stimulated equine neutrophils using lucigenin-enhanced chemiluminescence and on purified equine myeloperoxidase activity measured by specific immunological extraction followed by enzymatic detection. The methanolic, aqueous crude extract, and aqueous crude extract free of tannins exhibited good growth inhibition on Trypanosoma brucei brucei (IC50 3.72, 6.05, and 4.45 µg/mL respectively) but were inactive against Leishmania mexicana mexicana (IC50 > 100 µg/mL). Suramin (IC50 0.11 µg/mL) and amphotericin (IC50 0.11 µg/mL) were used as standard respectively for the antitrypanosomal and antileishmanial activity. Very interesting antioxidant and anti-inflammatory-like activities were observed with 50% hydroethanolic, aqueous crude extracts, and aqueous crude extract free of tannins as well as with pure punicalagin, gallic, and ellagic acid (IC50 0.38 – 10.51 µg/mL for 2,2′-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid), chemiluminescence, and specific immunological extraction followed by enzymatic detection assays. The study results support traditional medicinal use of the plant for the treatment of parasitical disorders and revealed for the first time the antitrypanosomal potential, anti-inflammatory-like, and antioxidant activity of Terminalia mollis root.

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Chemical Composition of the Essential Oil of Croton bonplandianus from India

Natural Product Communications ◽

10.1177/1934578x1400900234 ◽

2014 ◽

Vol 9 (2) ◽

pp. 1934578X1400900

Author(s):

Rajesh K. Joshi

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Chemical Composition ◽

Essential Oil ◽

Gas Chromatography Mass Spectrometry ◽

Caryophyllene Oxide ◽

Aerial Parts ◽

Sesquiterpene Hydrocarbons ◽

Germacrene D ◽

Total Oil

The essential oil obtained from the aerial parts of Croton bonplandianus Baill. was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). A total of 37 compounds have been identified, representing 96.2% of the total oil. The main constituents were identified as β-caryophyllene (16.7%), germacrene D (14.7%), borneol (8.3%), Z-β-damascenone (6.(%), isobornyl acetate (6.2%), α-humulene (6.1%), germacrene A (5.2%) and caryophyllene oxide (4.5%). The oil was rich in sesquiterpene hydrocarbons (60.1%).

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

Natural Product Communications ◽

10.1177/1934578x1000501232 ◽

2010 ◽

Vol 5 (12) ◽

pp. 1934578X1000501 ◽

Cited By ~ 3

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.

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Chemical Composition of the Essential Oils of Three Species of Apiaceae Growing Wild in Sicily: Bonannia graeca, Eryngium maritimum and Opopanax chironium

Natural Product Communications ◽

10.1177/1934578x1300800640 ◽

2013 ◽

Vol 8 (6) ◽

pp. 1934578X1300800 ◽

Cited By ~ 3

Author(s):

Antonella Maggio ◽

Maurizio Bruno ◽

Carmen Formisano ◽

Daniela Rigano ◽

Felice Senatore

Keyword(s):

Chemical Composition ◽

Essential Oils ◽

Aerial Parts ◽

Germacrene D ◽

Eryngium Maritimum

In the present study the chemical composition of the essential oils from aerial parts of Bonannia graeca (L.) Halácsy and Opopanax chironium (L.) Kock, and from aerial parts and roots of Eryngium maritimum L. was evaluated by GC and GC-MS. α-Pinene (15.2%) and β-pinene were recognized as the main constituents of B. graeca, whereas the aerial parts of O. chironium contained mainly the diterpene cembrene and the coumarin angelicin. In both aerial parts and roots of E. maritimum germacrene D (10.4% and 15.9%, respectively) and 2,4,5-trimethylbenzaldehyde (8.3% and 6.7%) were the most abundant components.

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Chemical Composition of the Essential Oil of Lepidagathis Fasciculata from Bondla Forest of Goa, India

Natural Product Communications ◽

10.1177/1934578x1300800834 ◽

2013 ◽

Vol 8 (8) ◽

pp. 1934578X1300800

Author(s):

Rajesh K. Joshi

Keyword(s):

Mass Spectrometry ◽

Gas Chromatography ◽

Chemical Composition ◽

Essential Oil ◽

Ionization Detector ◽

Flame Ionization ◽

Aerial Parts ◽

Sesquiterpene Hydrocarbons ◽

Germacrene D ◽

Total Oil

The hydro-distilled essential oil obtained from the flowering aerial parts of Lepidagathis fasciculata Nees was analyzed by gas chromatography equipped with a flame ionization detector (GC-FID) and gas chromatography coupled with mass spectrometry (GC/MS). A total of 38 compounds have been identified, representing 91.2% of the total oil. The major constituents were δ-cadinene (14.4 %), γ-curcumene (9.8%), sandaracopimarinal (6.6%), germacrene D-4-ol (6.1%), cembrene (5.0%), β-calacorene (3.6%), ar-curcumene (3.3%), trans–4,10-epoxy-amorphane (3.2%), abietatriene (2.9%), and α-cubebene (2.8%). The oil was rich in sesquiterpene hydrocarbons (43.8%).

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Chemical Composition of Marrubium Vulgare l. Essential Oil from Algeria

International Letters of Chemistry Physics and Astronomy ◽

10.18052/www.scipress.com/ilcpa.13.210 ◽

2013 ◽

Vol 13 ◽

pp. 210-214 ◽

Cited By ~ 2

Author(s):

Abderazak Abadi ◽

Aicha Hassani

Keyword(s):

Chemical Composition ◽

Essential Oil ◽

Oil Yield ◽

Aerial Parts ◽

Germacrene D ◽

Marrubium Vulgare

The chemical constituants of the essential oil from aerial parts of Marrubium vulgare, collected in Algeria, were analyzed by GC and GC/MS. The oil yield of the dried plant aerial parts, obtained by hydrodistillation, was 0.04% (w/w). 50 compounds, accounting for 82.46% of the oil, were identified. The major constituants were: 4,8,12,16-Tetramethyl heptadecan-4-olid (16.97%), Germacrene D-4-ol (9.61%), α-pinéne (9.37%) Phytol (4.87%), Dehydro-sabina ketone (4.12 %), Piperitone (3.27%), δ – Cadinene (3.13%), 1-Octen-3-ol (2.35%) and Benzaldehyde (2.31%).

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Chemical composition and antifungal potential of essential oils from different aerial parts of Protium ovatum Engl

Australian Journal of Crop Science ◽

10.21475/ajcs.21.15.04.p2915 ◽

2021 ◽

pp. 570-576

Author(s):

Wendel C. de Sousa ◽

Josemar G. Oliveira Filho ◽

Cassia C. F. Alves ◽

Moacir R. Forim ◽

Cristiane de M. Cazal

Keyword(s):

Chemical Composition ◽

Antifungal Activity ◽

Essential Oil ◽

Essential Oils ◽

Antimicrobial Agents ◽

Ripe Fruit ◽

Aerial Parts ◽

Potential Source ◽

Antifungal Potential ◽

Germacrene D

Protium ovatum is a Brazilian endemic species widely distributed between the Cerrado and Amazon biomes. Here, we evaluate the chemical composition of the essential oils (EO) of different shoot organs from P. ovatum including stems, petioles, leaves, flowers, ripe and unripe fruits, and investigate their antifungal potential against Sclerotinea sclerotiorum. The EO were obtained by hydrodistillation in a Clevenger-type apparatus and analysed by GC-MS, followed by PCA analysis. The antifungal activity was performed by agar diffusion. Fruits had the highest essential oil contents among the shoot parts. The constituents were found varyingin the different organs: α-Pinene (0.80-18.3%), β-Pinene (0.58-5.17%), Myrcene (0.52-27.3%), Limonene (3.15-59.7%), Caryophyllene E (3.67-16.4%), Germacrene D (6.34-27.4%), and δ-Cadinene (2.29-7.63%). The essential oil from ripe fruit showed the strongest antifungal activity, with the highest Inhibition of Mycelial Growth (IMG) (50.11%) at the lowest concentration assayed (18.75μg.mL-1). This is the first report on the chemical composition of the essential oils from stems, petioles, flowers, and ripe fruits of P. ovatum and their antifungal activity against S. sclerotiorum, making it a potential source of antimicrobial agents

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Chemical Composition of Hypericum richeri subsp. grisebachii Essential Oil from Croatia

Natural Product Communications ◽

10.1177/1934578x1300800226 ◽

2013 ◽

Vol 8 (2) ◽

pp. 1934578X1300800

Author(s):

Igor Jerković ◽

Maja Marasović ◽

Zvonimir Marijanović ◽

Kroata Hazler Pilepić ◽

Željan Maleš ◽

...

Keyword(s):

Fatty Acids ◽

Chemical Composition ◽

Essential Oil ◽

Essential Oils ◽

Decanoic Acid ◽

Chemical Profile ◽

Aerial Parts ◽

Ms Analysis ◽

Germacrene D

The aerial parts of Hypericum richeri Vill. subsp. grisebachii (Boiss.) Nyman were collected from two different locations in Croatia and subjected to hydrodistillation. GC/FID and GC/MS analysis of the isolated essential oils revealed 64 compounds representing 94.7% and 98.2% of the total oils. Predominant constituents in both samples were: germacrene D (10.9%; 6.0%), bicyclogermacrene (4.7%; 3.5%), α-pinene (6.8%; 6.9%), β-pinene (8.1%; 5.1%), decanoic acid (4.5%; 6.8%), β-caryophyllene (3.3%; 7.5%), δ-cadinene (7.0%; 4.4%), spathulenol (6.0%; 9.5%) and tetracosane (3.1%; 5.8%). Comparison of both samples revealed similarity in the chemical composition with minor fluctuations of constituent percentages. The chemical profile of Croatian oils was in general similar to those reported for other geographic areas regarding major mono- and sesquiterpene constituents. However, spathulenol, 5-cadinene and bicyclogermacrene were more abundant in Croatian oils. The presence of decanoic acid (4.5%; 6.8%) in Croatian oils was the major difference between acids and fatty acids derivatives. Higher abundance of alkanes (particularly tetracosane and docosane) was also noticed.

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Essential Oil Composition and Antimicrobial Activity of Ballota nigra L. ssp Foetida

Natural Product Communications ◽

10.1177/1934578x0900400429 ◽

2009 ◽

Vol 4 (4) ◽

pp. 1934578X0900400 ◽

Cited By ~ 1

Author(s):

Daniele Fraternale ◽

Anahi Bucchini ◽

Laura Giamperi ◽

Donata Ricci

Keyword(s):

Antimicrobial Activity ◽

Chemical Composition ◽

Essential Oil ◽

Essential Oil Composition ◽

Caryophyllene Oxide ◽

Oil Composition ◽

Gram Negative ◽

Gram Positive Bacteria ◽

Aerial Parts ◽

Germacrene D

The chemical composition of the essential oil of Ballota nigra L. ssp foetida obtained from the flowering aerial parts was analyzed by GC/MS. From the 37 identified constituents of the oil, β-caryophyllene (20.0%), germacrene D (18.0%) and caryophyllene oxide (15.0%) were the major components. The oil was active against both Gram-negative and Gram-positive bacteria as well as against three Candida species.

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Analysis of the Essential Oil of Teucrium polium ssp. capitatum from the Balkan Peninsula

Natural Product Communications ◽

10.1177/1934578x1200700129 ◽

2012 ◽

Vol 7 (1) ◽

pp. 1934578X1200700 ◽

Cited By ~ 1

Author(s):

Violeta Mitić ◽

Olga Jovanović ◽

Vesna Stankov-Jovanović ◽

Bojan Zlatkovic ◽

Gordana Stojanovic

Keyword(s):

Chemical Composition ◽

Essential Oil ◽

Balkan Peninsula ◽

Flowering Period ◽

Aerial Parts ◽

Germacrene D ◽

Teucrium Polium

The chemical composition of the essential oil of the aerial parts of Teucrium polium ssp. capitatum collected during the flowering period from rocky places and dry pastures, (Serbia, Niŝ, Kamenica), and dunes along the sea-side, (Bulgaria, Burgas, Primorsko) has been studied by GC and GC/MS. The identified compounds, 45 for the oil from Serbia and 44 for that from Bulgaria, amounted to 97.3% and 96.4% of the oils, respectively. The dominant constituents of the Serbian oil were sesquiterpenes {59.6%, the most abundant components being germacrene D (31.8%), trans-caryophyllene (8.8%) and bicyclogermacrene (6.2%)}, while monoterpenes accounted for 37.5% {the most abundant components being linalool (14.0%) and β-pinene (10.7%)}. The essential oil from Bulgaria was characterized by a high percentage of monoterpenes, amounting to 62.9% {the most abundant components being β-pinene (26.8%), α-pinene (9.3%) and limonene (6.4%)}, while sesquiterpenes accounted for 33.5% (the most abundant component was germacrene D 17.7%)}.

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