scholarly journals Essential Oils from Bolivia. XV. Herzogole, an Original Monoterpene Benzodioxole from an Essential Oil from Pentacalia herzogii (Cabrera) Cuatrec

Molecules ◽  
2021 ◽  
Vol 26 (19) ◽  
pp. 5766
Author(s):  
Alexis St-Gelais ◽  
Eliana M. Maldonado ◽  
Gloria Saavedra ◽  
Samuel Siles-Alvarado ◽  
Jérôme Alsarraf ◽  
...  

Over 15 years, with the support of a Canadian funding agency, the Universidad Mayor de San Simón, in Bolivia, undertook a large survey of aromatic plants of the South American country. More than a hundred species were studied under various aspects, including the production and characterization of essential oils. As part of this survey, the chemical composition of an essential oil sample obtained from Pentacalia herzogii (Asteraceae) growing wild in the High Valley region of the department of Cochabamba was determined by a combination of GC and GC-MS measurements. α-Pinene was the main constituent of this essential oil (34%), accompanied by limonene (22%) and germacrene D (7.5%) as well as an important fraction of methoxylated monoterpenoids. They were mainly isomers of thymol methyl ether, accounting for 13% of the chromatogram. A new quantitatively important compound (9%) was identified through NMR and chemical synthesis as 4-isopropyl-6-methylbenzo[d][1,3]dioxole, and designated herzogole, alongside the minor related compound 1-isopropyl-2,3-dimethoxy-5-methylbenzene. The monoterpene benzodioxole featured a distinctive green-phenolic aroma which could raise interest for fragrance use. Since these compounds were not known naturally, a biosynthetic mechanism of their formation was proposed and put in perspective to illustrate the metabolic originality of P. herzogii.

2015 ◽  
Vol 10 (4) ◽  
pp. 1934578X1501000
Author(s):  
Yu-Chang Su ◽  
Kuang-Ping Hsu ◽  
Eugene I-Chen Wang ◽  
Chen-Lung Ho

In this study, anti-mildew activities of the essential oils of the leaves, wood, twigs, flowers, and their constituents from Michelia compressa var. formosana were evaluated in vitro against 7 mildew fungi. The main compounds responsible for the anti-mildew activities were isolated and identified. The essential oils from the fresh leaves, wood, twigs, and flowers of M. compressa var. formosana were isolated using hydrodistillation in a Clevenger-type apparatus, and characterized by GC-FID and GC-MS. The essential oil yield from the flowers was the highest, and the oils obtained from the 4 parts of the tree were composed mainly of sesquiterpenoids. The leaf oil consisted primarily of α-cadinol (18.9%) and germacrene D (18.5%); the twig oil's main constituent was α-cadinol (19.1%); the wood oil's major components were α-cadinol (25.7%) and β-eudesmol (20.2%); and the flower oil contained α-cadinol (11.4%). Comparing the anti-mildew activities of the oils suggested that wood oil was the most effective. Further fractionation of the wood oil produced α-cadinol, β-eudesmol, τ-cadinol, and elemol. The 4 compounds exhibit very strong anti-mildew activities, and these in descending order are α-cadinol, elemol, β-eudesmol, and τ-cadinol. For the anti-mildew activities of the wood oil, the active source compounds were determined to be α-cadinol, elemol, β-eudesmol, and τ-cadinol.


Author(s):  
Yoro Tine ◽  
Alioune Diallo ◽  
William Diatta ◽  
Jean-Marie Desjobert ◽  
Jean Costa ◽  
...  

Zanthoxylum leprieurii belonging to Rutaceae family, is a medicinal and aromatic plants widely used in ethnopharmacology. Like other plants of Rutaceae family such as Citrus sp., the essential oils of this species could be used in cosmetic and pharmaceutical products. Thus, the essential oils of Z. leprieurii from different plant organs (fruit, leaf, stem and root) were investigated by using GC and GC-MS. The volatile composition of Z. leprieurii fruits exhibited relative high amounts of hydrocarbons monoterpenes (90.9%) such as (E)-β-ocimene (50.9%) and a-pinene (30.4%). The chemical composition of fruit oils was compared with volatile fractions of leaves, stems and roots from the same plant station. Germacrene B (9.0%), b-phellandrene (7.6%), caryophyllene oxide (7.2%) and b-caryophyllene (5.3%) were identified as the major constituents of leaves whereas the essential oil composition of the roots dominated by sesquiterpenes (83.3%) such as germacrone (23.5%), germacrene B (19.1%), g-elemene (6.0%), elemenone (4.0%) and b-elemene (2.4%) in the essential oil of the stems, b-Phellandrene (12.7%), germacrene B (5.0%), germacrene D (4.7%) and cis-9-Octadecen-1-ol (4.6%) have been reported as majority compounds.


2006 ◽  
Vol 1 (5) ◽  
pp. 1934578X0600100 ◽  
Author(s):  
Walber H. F. Ribeiro ◽  
Jackson N. Vasconcelos ◽  
Angela M. C. Arriaga ◽  
Maria C. F. de Oliveira ◽  
Manoel Andrade-Neto ◽  
...  

The essential oils obtained by hydrodistillation of the leaves, stems, and shoots of Tephrosia toxicaria Pers (Papilionaceae) were analyzed using GC and GC/MS. Germacrene D was the major component (20.7-33.3 %) of the oils of leaves and shoots, whereas spathulenol was the main constituent (42.3%) of the stem oil. The essential oils from the leaves and stems, when tested for activity against mosquito larvae (Aedes aegypti), gave LC 50 values of 81.3 ± 2.9 and 63.1 ± 1.0 ppm, respectively.


2020 ◽  
Vol 24 (9) ◽  
pp. 909-1009
Author(s):  
Maryam Akaberi ◽  
Zahra Tayarani-Najaran ◽  
Iraj Mehregan ◽  
Javad Asili ◽  
Amirhossein Sahebkar ◽  
...  

One of the most important families of Iranian flora is Apiaceae (Umbelliferae). Most of the species of this family are aromatic plants and rich in essential oils with diverse structures. In the present review, the essential oil composition of 63 genera comprising 141 Apiaceae (66.4% native 33.6% endemic) is summarized.


Plants ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1061
Author(s):  
Sims K. Lawson ◽  
Prabodh Satyal ◽  
William N. Setzer

As part of our evaluation of essential oils derived from Native American medicinal plants, we have obtained the essential oils of Agastache foeniculum (Pursch) Kuntze (Lamiaceae), Gaultheria procumbens L. (Ericaceae), Heliopsis helianthoides (L.) Sweet (Asteraceae), Liatris spicata (L.) Willd. (Asteraceae), Pycnanthemum incanum (L.) Michx. (Lamiaceae), Smallanthus uvedalia (L.) Mack. ex Mack. (Asteraceae), and Verbena hastata L. (Verbenaceae) by hydrodistillation. The essential oils were analyzed by gas chromatographic techniques. The essential oil of A. foeniculum was dominated by estragole (88–93%), while methyl salicylate (91%) dominated the G. procumbens essential oil. Germacrene D was the major component in H. helianthoides (42%) and L. spicata (24%). 1,8-Cineole (31%) and α-terpineol (17%) were the main compounds in P. incanum essential oil. The essential oil of S. uvedalia showed α-pinene (24%), perillene (15%), and β-caryophyllene (17%) as major components. Verbena hastata essential oil was rich in 1-octen-3-ol (up to 29%) and palmitic acid (up to 22%). Four of these essential oils, H. helianthoides, L. spicata, P. incanum, and V. hastata, are reported for the first time. Additionally, the enantiomeric distributions of several terpenoid components have been determined.


Author(s):  
Maria Ioana MORAR ◽  
Florinela FETEA ◽  
Ancuta Mihaela ROTAR ◽  
Melinda NAGY ◽  
Cristina Anamaria SEMENIUC

Four essential oils isolated from dried leaves of parsley, lovage, basil, and thyme were investigated by FTIR spectroscopy. FTIR spectra revealed characteristic key bands for the main compounds of tested essential oils.


2014 ◽  
Vol 9 (1) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Ammar Bader ◽  
Pier Luigi Cioni ◽  
Nunziatina De Tommasi ◽  
Guido Flamini

The composition of the essential oils of flowering aerial parts of Salvia samuelssonii Rech. fil. (Lamiaceae Section Aethiopis), collected in two different biogeographical regions, has been analyzed. Sample1, collected in a Mediterranean-like region, “As-Subayhi”, contains mainly monoterpenes (54.2%), sesquiterpenes (27.6%) and phenylpropanoids (10.5%), while sample 2, collected in the Irano-Turanian region, “Al-Adasiyyah”, contains mainly phenylpropanoids (30.6%), monoterpenes (24.9%) and sesquiterpenes (21.2%). In Sample1, the most representative constituents were sabinene (21.5%), cis-chrysanthenyl acetate (20.8%), germacrene D (9.3%) and myristicin (5.9%), while in sample 2, myristicin (24.1%), sclareoloxide (6.3%), and germacrene D (5.7%) were main constituents. The rate of oxygenated derivatives in the Irano-Turanian sample was higher than the Mediterranean sample. Myristicin is an unusual constituent of Salvia species.


2012 ◽  
Vol 7 (1) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Naciye Erkan ◽  
Zhou Tao ◽  
H. P. Vasantha Rupasinghe ◽  
Burcu Uysal ◽  
Birsen S. Oksal

Solvent-free microwave extraction (SFME) for the isolation of essential oil from leaves of Murraya koenigii L. (Rutaceae) has been compared with the conventional hydro-distilled oil (HD) in terms of yield, composition, antioxidant activity, and antibacterial activity against Listeria innocua. The yield of essential oil obtained from 30 min of SFME was similar to that of HD for 180 min. By GC-MS analysis, the major compounds of the essential oil extracted by SFME, which were obtained in somewhat lower amounts than in the essential oil obtained by HD, were α-copaene (44.3%), β-gurjunene (25.5%), isocaryophyllene (12.1%), β-caryophyllene (8.7%) and germacrene D (2.9%). The content of oxygenated terpenes, slightly higher for the SFME-essential oil (2.3%) than the HD-essential oil (1.4%), were much lower than that of nonoxygenated terpenes in both oils. DPPH radical scavenging activities of both essential oils were relatively low (10%-24%). Complete inhibition of growth of L. innocua was observed with both SFME and HD essential oils, at 400 and 600 μg/mL (minimum inhibitory concentration), respectively. The SFME-essential oil at 300 μg/mL provided 92% inhibition, indicating its potential as a natural antimicrobial agent.


2018 ◽  
Vol 13 (7) ◽  
pp. 1934578X1801300
Author(s):  
Biljana Nikolić ◽  
Milić Matović ◽  
Marina Todosijević ◽  
Jovana Stanković ◽  
Mirjana Cvetković ◽  
...  

Terpene compounds of Tanacetum macrophyllum as 1) essential oils, obtained by hydrodistillation (HD), 2) essential oil extracts, obtained by simultaneous hydrodistillation and extraction (SDE) and 3) volatiles, obtained by Static Headspace GC-MS analysis (HS) were processed. Monoterpenes were the most dominant (49.2%, 49.5% and 90.4%, respectively). Profiles of essential oils obtained by HD and SD were quite similar, with oxygenated monoterpenes (39.3% and 39.4%) being the most abundant. In HS volatiles oxygenated monoterpenes also dominated (57.4%). Total sesquiterpenes were abundant in HD and SDE volatiles (38.2% and 39.2%, resp.), where sesquiterpene hydrocarbons were prevalent (27.3% and 28.7%, resp.). Germacrene D was dominant in HD and SDE oils (22.0% and 23.3%, resp.) and 1,8-cineole in HS volatiles (34.3%). To our knowledge, this is the first use of Headspace technique on T. macrophyllum. Furthermore, this is the first comparison of different techniques of volatile extraction in T. macrophyllum.


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