Institute Ciencias Agrarias CCMA

Serrano, Spain

Institute Ciencias Agrarias CCMA

Serrano, Spain
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Guardo N.I.,Institute Ciencias Agrarias CCMA | Sainz P.,Institute Ciencias Agrarias CCMA | Gonzalez-Coloma A.,Institute Ciencias Agrarias CCMA | Burillo J.,CSIC - Centro de Investigación y Tecnología Agroalimentaria | Martinez-Diaz R.A.,Autonomous University of Madrid
Natural Product Communications | Year: 2017

Fourteen essential oils (EOs) from selected live germplasm of medicinal plants have been tested for their antitrypanosomal and cytotoxic activity. These plants have been domesticated and maintained under experimental cultivation. Their EOs were tested on epimastigote forms of Trypanosoma cruzi strain Y and human lung fibroblasts LC5 cell line, along with the major components of the active oils, both separately and in binary combinations. Mentha rotundifolia, Thymus zygis, T. vulgaris and Hyssopus officinalis were the most active EOs against T. cruzi. Among the main components of these EOs (1-8-cineole, thymol, p-cymene, piperitenone oxide, β-pinene, γ-terpinene, carvacrol and linalool), the most active against the parasite and less toxic to human cells was thymol. In general, the activity of the main components did not exceed that of their origin EO, and the study of the activity of these compounds in combination indicates the existence of antagonistic and synergistic effects depending on the concentration tested.

Mazoir N.,Cadi Ayyad University | Benharref A.,Cadi Ayyad University | Bailen M.,Institute Ciencias Agrarias CCMA | Reina M.,CSIC - Institute of Natural Products and Agrobiology | And 2 more authors.
Zeitschrift fur Naturforschung - Section C Journal of Biosciences | Year: 2011

The in vitro activity on Leishmania infantum promastigotes and Trypanosoma cruzi epi-mastigotes of 25 semisynthetic terpenoid derivatives has been evaluated. These compounds were obtained through chemical modifi cations of the major components of Euphorbia res-inifera (α-euphol and α-euphorbol) and Euphorbia offi cinarum (obtusifoliol and 31-norla-nosterol). Leishmaniasis and Chagas ́ disease are major worldwide health problems. The drugs of choice for their treatment are still problematic in both cases, and therefore there is an urgent need to discover new drugs with high activity and low side effects. Natural products have become a key source of new drugs in the last years. The genus Euphorbia has been the subject of abundant phytochemical and pharmacological research because of its potential medical applications, but the antiparasitic effects of derivatives from plants of this genus are still unknown. Our results showed that 76% and 64% of the test compounds had antiparasitic effects on L. infantum and T. cruzi, respectively. The different activities on both parasites, especially their moderate effects on mammalian cells, indicate an interesting selective toxicity. © 2011 Verlag der Zeitschrift für Naturforschung, Tübingen.

Rodilla J.M.,University of Beira Interior | Silva L.A.,University of Beira Interior | Davyt D.,Catedra de Quimica Farmaceutica | Castillo L.,Institute Ciencias Agrarias CCMA | And 4 more authors.
Industrial Crops and Products | Year: 2011

Bulnesia sarmientoi Lorentz ex Griseb volatile oil was characterized by GC × GC-TOF-MS analysis. Major components were guaiol and bulnesol, followed by hanamyol. The enhanced sensitivity and superior resolution of GC × GC resulted in the identification of thus-far unreported oil constituents as β-guaiene, guaioxide, elemol, germacrene-B, eudesm-5-en-11-ol, γ-eudesmol, α-eudesmol and (-)-hanamyol. The insecticidal effect of B. sarmientoi oil and its main constituents (guaiol, bulnesol and hanamyol) on Spodoptera littoralis, Rhopalosiphum padi and Myzus persicae was studied. Guaiol affected the aphids in a dose-response fashion, showing low efficiency, while bulnesol and hanamyol were inactive. Both the oil and its constituents were also assayed for antifungal action against Fusarium spp. and phytotoxicity to Lactuca sativa. Among the pure compounds tested, bulnesol had a low-moderate effect on Fusarium moniliforme while hanamyol had a strong effect on Fusarium solani. Neither the oil nor the tested compounds affected L. sativa germination or radicle length, indicating that B. sarmientoi is not phytotoxic. © 2010 Elsevier B.V.

Abad A.,University of Valencia | Agullo C.,University of Valencia | Cunat A.C.,University of Valencia | Gonzalez-Coloma A.,Institute Ciencias Agrarias CCMA | Pardo D.,University of Valencia
European Journal of Organic Chemistry | Year: 2010

The preparation of 9α-fluoro analogues of both natural and unnatural drimane-type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8-keto-12-nordriman-11-oate from β-ionone and entailed the electrophilic fluorination of C-9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from, the intermediate 9α-fluoro-8-keto-12-nordrimane system by means of different reactions at the C-8 ketone carbonyl group, essentially Wittig methylenation, cyanohydrin formation or palladium-catalysed carbonylation of the corresponding enol triflate. Further manipulation of the functionalization derived from these key reactions allowed the preparation, among others, of 9α-fluorodrimanes, which are structurally and functionally related to albicanic acid, drimenin and olepupuane. Also described are the reactivities of some of the fluorine-containing systems prepared and a comparative study of the antifeedant activities of a selection of 9α-fluorodrimanes and the corresponding hydrogen analogues against several, insect species with different feeding ecologies (Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi), which revealed a significant increase in the antifeedant activities of some of the fluorinated drimane analogues. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

Gonzalez-Coloma A.,Institute Ciencias Agrarias CCMA | Delgado F.,Polytechnic Institute of Coimbra | Rodilla J.M.,University of Beira Interior | Silva L.,University of Beira Interior | And 2 more authors.
Biochemical Systematics and Ecology | Year: 2011

The chemical composition and biological activity of wild Lavandula luisieri (Rozeira) Rivas-Martínez populations from the south Beira interior region in central eastern Portugal are described. The essential oils of these four populations have been analyzed by GC-MS, and their antifeedant effects evaluated against Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi. Relative concentration data (% values) was subjected to principal component and cluster analysis. Relative concentration data and antifeedant effects were subjected to a stepwise multiple regression analysis. Additionally, one of these populations has been adapted to experimental field cultivation. © 2010 Elsevier Ltd.

Gonzalez-Coloma A.,Institute Ciencias Agrarias CCMA | Lopez-Balboa C.,Institute Ciencias Agrarias CCMA | Santana O.,Institute Ciencias Agrarias CCMA | Reina M.,CSIC - Institute of Natural Products and Agrobiology | Fraga B.M.,CSIC - Institute of Natural Products and Agrobiology
Phytochemistry Reviews | Year: 2011

Pentacyclic triterpenes are abundant in the plant kingdom and have a wide array of pharmacological activities. They also have insect antifeedant effects and therefore apparently play a role in plant defense. In this paper, we describe the insecticidal activity of pentacyclic triterpenes of plant origin from different chemical classes on several insect pests (Spodoptera littoralis, Leptinotarsa decemlineata and Myzus persicae), their phytotoxic properties and their selective cytotoxic effects on insect-derived Sf9 and mammalian CHO cells. We also discuss the role they play in plant defense based on these activities. © 2010 Springer Science+Business Media B.V.

Hernandez-Carlos B.,University of the Sea | Gonzalez-Coloma A.,Institute Ciencias Agrarias CCMA | Orozco-Valencia A.U.,University of the Sea | Ramirez-Mares M.V.,University of the Sea | And 2 more authors.
Phytochemistry | Year: 2011

Eleven oleanane-type saponins (1-11) have been isolated from Microsechium helleri and Sicyos bulbosus roots and were evaluated for their antifeedant, nematicidal and phytotoxic activities. Saponins {3-O-β-d-glucopyranosyl (1 → 3)-β-d-glucopyranosyl-2β,3β,16α,23- tetrahydroxyolean-12-en-28-oic acid 28-O-α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-[β-d-xylopyranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside} (1), and {3-O-β-d-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12- en-28-oic acid 28-O-α-l-rhamnopyranosyl-(1 → 3)-β-d- xylopyranosyl-(1 → 4)-[β-d-xylopyranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside} (2) were also isolated from M. helleri roots together with the two known compounds 3 and 4. Seven known structurally related saponins (5-11) were isolated from S. bulbosus roots. The structures of these compounds were established as bayogenin and polygalacic glycosides using one- and two-dimensional NMR spectroscopy and mass spectrometry. Compounds 7, 10, bayogenin (12) and polygalacic acid (13) showed significant (p < 0.05) postingestive effects on Spodoptera littoralis larvae, compounds 5-11 and 12 showed variable nematicidal effects on Meloydogyne javanica and all tested saponins had variable phytotoxic effects on several plant species (Lycopersicum esculentum, Lolium perenne and Lactuca sativa). These are promising results in the search for natural pesticides from the Cucurbitaceae family. © 2011 Elsevier Ltd. All rights reserved.

Jaramillo-Colorado B.,University of Cartagena | Julio-Torres J.,University of Cartagena | Duarte-Restrepo E.,University of Cartagena | Gonzalez-Coloma A.,Institute Ciencias Agrarias CCMA | Julio-Torres L.F.,Institute Ciencias Agrarias CCMA
Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas | Year: 2015

The objectives of this work were to study the volatile chemical composition of essential oil (EO) from Piper marginatun Jacq (Piperaceae), obtained from plants collected in two Colombian geographic locations: municipalities Acandí (Chocó) and Turbaco (Bolívar). Also, evaluate their antioxidant, repellent and antifeedant properties. EOs were isolated by hydrodistillation technique and identified by gas chromatography coupled to a mass spectrometric detector (GC-MS). The major compounds found in P. marginatum collected in Acandi were cis-p-anethole (46.3%), estragole (28.9%), safrole (9.0%), while in P. marginatum from Turbaco were germacrene D (36.6%), β-elemene (12.6%), germacren-D-4-ol (5.4%). The antioxidant activity of the EOs were determined using the method of DPPH radical. The percentages of inhibition of DPPH. of P marginatum from Turbaco and Acandí were 90.0% and 73.7%, respectively. The EO from Turbaco had the highest repellent activity against Tribolium castaneum, at a concentration of 0.1 uL /cm2 at 2 and 4 hours of exposure (85% and 76% respectively). P. marginatum from Turbaco was more active against Spodoptera littoralis larvae (Percent feeding inhibition, FI= 80.6%) and a high Percent settling inhibition of Myzus persicae and Rhopalosiphum padi (SI = 87.9% and 86, 4%). © 2015.

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