Paola Di Leo Lira

Triterpenic Acids and Flavonoids from Satureja parvifolia. Evaluation of their Antiprotozoal Activity

Bioassay-guided fractionation of a Satureja parvifolia MeOH extract led to the isolation of eriodictyol, luteolin and ursolic and oleanolic acids as its active components against Plasmodium falciparum K1. This is the first time these compounds are reported as constituents of S. parvifolia. Ursolic acid showed an IC50 of 4.9 μg/ml, luteolin 6.4 μg/ml, oleanolic acid 9.3 μg/ml and eriodictyol 17.2 μg/ml. Antiplasmodial activity of eriodictyol and luteolin is reported here for the first time. Besides, the four compounds showed activity against P. falciparum 3D7 strain and Trypanosoma brucei rhodesiense. Eriodictyol showed moderate activity on all the parasites but was the most selective compound as a result of its rather low cytotoxicity (IC50 174.2 μg/ml) on the mammalian KB cell line.

Characterization of Lemon Verbena (Aloysia citriodora Palau) from Argentina by the Essential Oil

Abstract The oils of twenty-three samples of Aloysia citriodora from the most important growing areas in our country have been analyzed using GC/FID/MS. Characterization of the oil compositions revealed chemical markers which can be used to define the quality of a typical Argentine lemon verbena. In addition to the normal neral (20.0%) and geranial (29.0%) rich oils, two unusual oil compositions were detected: one with high contents of limonene (40.3%) and citronellal (21.6%), the other rich in β-thujone (73.4%). These specifications can be used for the standardization of this plant, defining the best available quality of leaves and volatile fractions of argentine lemon verbena, and discriminating from potentially toxic materials and adulterants.

Volatile constituents of five Baccharis Species from Northeastern Argentina

Essential oils obtained by hydrodistillation from the aerial parts of Baccharis gaudichaudiana, B. microcephala, B. penningtonii, B. phyteumoides and B. spicata collected from different locations in Argentina were analyzed. Qualitative and quantitative analysis were performed using a GC/FID/MS system with a special configuration. Essential oil yields ranged from 0.1 to 0.2% (m/v of dry material). Different chemical patterns were observed in the essential oils composition of the species studied: spathulenol and β-pinene were the main constituents in B.gaudichaudiana, whereas caryophyllene oxide and spathulenol were the major constituents in B. microcephala and B. spicata. In this latter species, β-pinene has also been found in high amounts. Germacrene D was the major compound in B. penningtonii. Finally, β-selinene and phytol acetate E were the main components in B. phyteumoides.

The Essential Oil of the Aerial Parts of Adesmia boronioides Hook. f.

Abstract The leaves and stems of Adesmia boronioides Hook. f. collected in Patagonia, Argentina, were subjected to hydrodistillation yielding 0.3–1.5% of essential oils according to the season. The oils were analyzed by GC and GC/MS. The main constituents were two novel bisnorsesquiterpenes: esquel-6-en-9-one (19.1%) and esquel-7-en-9-one (12.5%), as well as α-copaen-11-ol (8.5%), δ-cadinene (5.1%), 10-epi-γ-eudesmol (4.6%), 4α-hydroxydihydroagarofuran (3.5%), 1-epi-cubenol (3.5%), and α-pinene (3.0%). The very pleasant sweet-woody, licorice-spicy odor of the oil suggests its potential utility in the fragrance industry.

Northwestern Argentina: A Center of Genetic Diversity of Lemon Verbena (Aloysia citriodora Paláu, Verbenaceae)

The aerial parts of lemon verbena (Aloysia citriodora Paláu) are worldwide used due to their medicinal and aromatic properties. The essential‐oil and acteoside contents have been proposed as the main quality markers for their pharmacological and organoleptic features. The northwestern region of Argentina has been repeatedly proposed as the place of origin for this species. For this reason, the essential‐oil yields and chemical compositions of leaves of 25 populations of lemon verbena from both wild collections and experimental crops from this region were studied. Plants from six different collections were subsequently grown on the same experimental parcel located at Cerrillos, Salta province, during more than seven years. In addition, the acteoside contents determined in all the samples collected in 2010 showed significant variations (from 0.5 to 4.0%). Large differences were observed in the essential‐oil composition and yields, which ranged from 0.4 to 2.1% (v/w). Nevertheless, most of the samples complied with the European Pharmacopoeia specifications. A remarkable chemical diversity with at least four clearly defined chemotypes was detected in this region. Therefore, it would be urgent to encourage actions to protect these genotypes of lemon verbena in the northwestern Argentina.

Chemical Composition and Bioactivity of Acantholippia seriphioides Essential Oils from Patagonia

Abstract The aerial parts of Acantholippia seriphioides (A. Gray) Mold. were collected from three sites in the neighborhood of Comodoro Rivadavia, in Patagonia (Astra, Saavedra and Rada Tilly), and their essential oils were analyzed by GC-FID/MS. Results obtained by the analysis indicated chemovariability in the oils from these sites when matched with other sites. Monoterpene hydrocarbons (92.6–95.1%) were the main group of constituents in all populations, mainly thymol (33.7–38.5%) p-cymene (26.5–35.3%) and γ-terpinene (8.3–12.7%). Essential oils were submitted to biological assays in order to assess their general toxic activity on Artemia salina, and the inhibition effects in the germination and seedling growth of Lactuca sativa. Saavedra sample, associated with greater limonene, carvone, carvacrol and p-cymene contents, was the most active to the A. salina test (LD50 = 23,08 μg/mL−1). Astra sample, associated to a greater relative proportion of γ-terpinene, thymol methyl ether and neral, was the most active to the germination and seedling growth test (IC50=1.86 μg/mL−1). Saavedra sample also showed high activity (IC50= 37.53 μg/mL−1). The bioactivities were not proportional to the content of present active monoterpenes

Structure, conformation and absolute configuration of novel bisnorsesquiterpenes from the Adesmia boronioides essential oil

Abstract Two novel bisnorsesquiterpenes (1R,4S,5R)-esquel-6-en-9-one ( 1 ) and (1R,4S,5S)-esquel-7-en-9-one ( 2 ) were isolated from the essential oil of Adesmia boronioides. Their structures and relative stereochemistry were elucidated by 1D and 2D NMR data, including carbon–carbon connectivity and NOESY experiments. The absolute configuration was determined by chemical conversion of 1 into phenol 6 , whose Cotton effect was compared with that of cacalol. The conformational behavior of the new compounds containing the hydrindane skeleton was studied by molecular mechanics. Compound 1 possesses a very pleasant fruity odor.

Composition of the Essential Oil of Pichana [Baccharis spartioides (Hook, et Arn.) Remy (Compositae)] from Different Populations of the Patagonia, Argentina

Abstract The essential oils of the aerial parts of Baccharis spartioides (Hook, et Arn.) Remy (Compositae) from three different Patagonian populations were obtained by hydrodistillation and analyzed by capillary GC and GC/M S. Fifty-four components, representing approximately 84.6–97.4% of the oil samples, were identified. The samples consisted mainly of hydrocarbons and oxygenated monoterpenes. The major constituents were limonene (28.7–56.7%), 6R-7R-bisabolone (3.2–9.1%), sabinene (0.1–11.0%) and citronellal (2.4–5.2%).

Essential oils of native and naturalized Lamiaceae species growing in the Patagonia region (Argentina)

Abstract This is the first comprehensive study of essential oils of wild aromatic Lamiaceae present in Patagonia, including exotic and native species. The most commonly representatives of this family in Patagonia include one species of the adventitious Origanum vulgare L., three naturalized mints, Mentha rotundifolia L., M. pulegium L. and M. spicata L. and two native species: Clinopodium darwinii (Benth.) Kuntze and Scutellaria nummulariifolia Hook. f. The essential oils were isolated by hydrodistillation of the aerial parts of each of these species collected during 3 years and analyzed by GC-FID-MS. The major components found were menthone (5.4–10.2%) and pulegone (78.3–89.8%) in M. pulegium; piperitenone oxide (75.6–68.7%) in M. rotundifolia; carvone (34.0–70.4%) in M. spicata; sabinene (2.7–5.9%), p-cymene (9.3–36.1%) and linalool (11.3–21.4%) in O. vulgare; pulegone (56.6–72.4%) in Clinopodium darwinii; acetophenone (19.0%) and α-terpineol (9.5%) in Scutellaria nummulariifolia. This is the first report on the chemical composition of the essential oil of S. nummulariifolia.

Volatile Constituents from Aerial Parts of Cunila spicata

Abstract The essential oil of the aerial parts of Cunila spicata Benth. (Lamiacaeae), was obtained by hydrodistillation and investigated by capillary GC and GC/MS. Fifty one components representing 91.8% of the oil were identified, consisting mainly of monoterpene hydrocarbons and oxygenated derivatives. The major constituents were limonene (25.9%), geranyl acetate (21.8%) and linalool (21.2%).