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    Matias Reina

    ... The selective decoupled (SFSD) spectra were obtained by low-power irradiation (1000 Hz) at the resonance 1973 Rt~' RO,, R2 ,N e R = H; R1 =R2 = OH, a HR=Bz. ... 1. Berm, MH and Jacyno, JM (1983) in A , Chemical and Biological... more
    ... The selective decoupled (SFSD) spectra were obtained by low-power irradiation (1000 Hz) at the resonance 1973 Rt~' RO,, R2 ,N e R = H; R1 =R2 = OH, a HR=Bz. ... 1. Berm, MH and Jacyno, JM (1983) in A , Chemical and Biological Perspectives (Pelletier, SW, ed.) Vol. 1, Chap. ...
    The furanoeremophilanes 6 beta-angeloyloxy-1,10-dehydrofuranoeremophilan-9-one (1), 6 beta-hydroxy-1,10-dehydrofuranoeremophilan-9-one (2) and 6 beta-propionyloxy-1,10-dehydrofuranoeremophilan-9-one (3) were isolated from Senecio otites,... more
    The furanoeremophilanes 6 beta-angeloyloxy-1,10-dehydrofuranoeremophilan-9-one (1), 6 beta-hydroxy-1,10-dehydrofuranoeremophilan-9-one (2) and 6 beta-propionyloxy-1,10-dehydrofuranoeremophilan-9-one (3) were isolated from Senecio otites, their structures elucidated by spectral analyses, and their insecticidal and phytotoxic properties evaluated. Compounds 1-3 proved to be effective aphid antifeedants against Myzus persicae and Rhopalosiphum padi and had postingestive negative effects on Spodoptera littoralis larvae. These compounds did not have any phytotoxic effects on Lactuca sativa.
    ... Page 2. Monooxygenase-like Oxidation of Hydrocarbons ... In the particular case of H202, similar reactions (eq 3 and 4) would explain the propensity of Fe( 111) porphyrins to dismutate H20210h11 as well as the poor ability of... more
    ... Page 2. Monooxygenase-like Oxidation of Hydrocarbons ... In the particular case of H202, similar reactions (eq 3 and 4) would explain the propensity of Fe( 111) porphyrins to dismutate H20210h11 as well as the poor ability of Fe(porphyrin)Cl-H202 systems for hydrocarbon ...
    ABSTRACT
    Tesis doctoral inédita realizada en la Universidad Autónoma de Madrid, Facultad de Medicina. Departamento de Medicina Preventiva, Salud Pública y Microbiología y el Insituto de de Productos Naturales y Agrobiologia (CSIC) . Fecha de... more
    Tesis doctoral inédita realizada en la Universidad Autónoma de Madrid, Facultad de Medicina. Departamento de Medicina Preventiva, Salud Pública y Microbiología y el Insituto de de Productos Naturales y Agrobiologia (CSIC) . Fecha de lectura: 28 de Mayo de 2010 Bibliografía: p. pp.271-292
    Twenty-four compounds including eleven eremophilanolides (1-11), one eremophilane (13), five shikimic acid derivatives (14-18), six flavonoids (19-24), and the macrocyclic unsaturated pyrrolizidine alkaloid integerrimine (25) were... more
    Twenty-four compounds including eleven eremophilanolides (1-11), one eremophilane (13), five shikimic acid derivatives (14-18), six flavonoids (19-24), and the macrocyclic unsaturated pyrrolizidine alkaloid integerrimine (25) were isolated from Senecio kingii, an endemic species from the Magallanes Region (Chile). Compounds 3, 5, 6, 8-11 and 13-18 have not been previously reported as natural products. Their molecular structures were determined by NMR spectroscopic analysis and comparison with published NMR data. An X-ray-analysis of compound 3 has been performed. Their insecticidal and antifungal activities were tested, being compound 3 the strongest insect antifeedant. Compounds 6, 9 and 18 were moderate antifungals.
    ... A CASE STUDY A. GONZALEZ-COLOMA ^\ M. REINA^ C. GUTIERREZ\ BM FRAGA^ ^Centro de Ciencias Medioambientales, CSIC, Serrano 115-dpdo ... We have focused mainly on the flora of the Canarian Archipelago because of its rich biodiversity... more
    ... A CASE STUDY A. GONZALEZ-COLOMA ^\ M. REINA^ C. GUTIERREZ\ BM FRAGA^ ^Centro de Ciencias Medioambientales, CSIC, Serrano 115-dpdo ... We have focused mainly on the flora of the Canarian Archipelago because of its rich biodiversity (Lauraceae, Compositae ...
    The structures of a new eudesmane sesquiterpene, lauradiol, and a new secoeudesmane, azoridione, have been determined by spectroscopic methods. These compounds and the known sesquiterpenic alcohols, clovanediol and caryophyllenol II, have... more
    The structures of a new eudesmane sesquiterpene, lauradiol, and a new secoeudesmane, azoridione, have been determined by spectroscopic methods. These compounds and the known sesquiterpenic alcohols, clovanediol and caryophyllenol II, have been isolated from the aerial parts of Laurus azorica.
    The furanoeremophilanes 6 beta-angeloyloxy-1,10-dehydrofuranoeremophilan-9-one (1), 6 beta-hydroxy-1,10-dehydrofuranoeremophilan-9-one (2) and 6 beta-propionyloxy-1,10-dehydrofuranoeremophilan-9-one (3) were isolated from Senecio otites,... more
    The furanoeremophilanes 6 beta-angeloyloxy-1,10-dehydrofuranoeremophilan-9-one (1), 6 beta-hydroxy-1,10-dehydrofuranoeremophilan-9-one (2) and 6 beta-propionyloxy-1,10-dehydrofuranoeremophilan-9-one (3) were isolated from Senecio otites, their structures elucidated by spectral analyses, and their insecticidal and phytotoxic properties evaluated. Compounds 1-3 proved to be effective aphid antifeedants against Myzus persicae and Rhopalosiphum padi and had postingestive negative effects on Spodoptera littoralis larvae. These compounds did not have any phytotoxic effects on Lactuca sativa.
    ABSTRACT
    ABSTRACT The absolute configuration (AC) of (+)-2R,7R,15R,17S,19S-10-demethoxy-12-hydroxy-17,19-epoxygeissovelline (1), a main aspidospermatan-type indoline alkaloid from Geissospermum reticulatum, was established by vibrational circular... more
    ABSTRACT The absolute configuration (AC) of (+)-2R,7R,15R,17S,19S-10-demethoxy-12-hydroxy-17,19-epoxygeissovelline (1), a main aspidospermatan-type indoline alkaloid from Geissospermum reticulatum, was established by vibrational circular dichroism (VCD), facilitating deduction of the AC of all structurally related alkaloids isolated from this plant.
    ... Page 2. Monooxygenase-like Oxidation of Hydrocarbons ... In the particular case of H202, similar reactions (eq 3 and 4) would explain the propensity of Fe( 111) porphyrins to dismutate H20210h11 as well as the poor ability of... more
    ... Page 2. Monooxygenase-like Oxidation of Hydrocarbons ... In the particular case of H202, similar reactions (eq 3 and 4) would explain the propensity of Fe( 111) porphyrins to dismutate H20210h11 as well as the poor ability of Fe(porphyrin)Cl-H202 systems for hydrocarbon ...
    ... 3 (Waterman, PG and Grundon, MF, eds). Academic Press, London. 20. Burke, AB and Parkins, H. (1978) Tetrahedron Letters 2723. 21. Burke, B., Parkins, H. and Talbot, AM (1979) Heterocycles 12, 349. 22. Philip, S., Burke, BA and Jacobs,... more
    ... 3 (Waterman, PG and Grundon, MF, eds). Academic Press, London. 20. Burke, AB and Parkins, H. (1978) Tetrahedron Letters 2723. 21. Burke, B., Parkins, H. and Talbot, AM (1979) Heterocycles 12, 349. 22. Philip, S., Burke, BA and Jacobs, H. (1984) Heterocycles 22,9. 23. ...
    The use of natural products for the treatment of protozoal infections (Leishmania and Trypanosoma spp.) is well known and has been documented since ancient times. We have already established an in vitro culture system using mammalian host... more
    The use of natural products for the treatment of protozoal infections (Leishmania and Trypanosoma spp.) is well known and has been documented since ancient times. We have already established an in vitro culture system using mammalian host cells (Vero) infected with Trypanosoma cruzi in which the time course of parasite growth is determined quantitatively. This system was used to screen anti-T. cruzi agents using two experimental models: simultaneous cell infection and compound addition or preincubation of the parasite with the test compound prior to cell infection. Among 64 diterpenoid alkaloids tested, including C19 and C20 skeletons, five C20 compounds were active on T. cruzi epimastigotes: azitine, isoazitine and 15,22-O-diacetyl-19-oxodihydroatisine had moderate effects on the parasite, while atisinium chloride and 13-oxocardiopetamine were potent T. cruzi epimastigote growth inhibitors with activity levels similar to that of benznidazole, used as the reference drug. Additionally, these compounds decreased the ability of metacyclic forms to invade mammalian cells, their intracellular replications and their transformation into trypomastigotes, with no toxicity to the host cell. These results suggest that these alkaloids are structural leads of clinically active compounds against T. cruzi and probably other members of the Trypanosomatidae.
    ... Centro de Productos Naturales Orgánicos “Antonio González” IPNAC-CSIC, La Laguna, Tenerife, Canary Islands, Spain. Emir Valencia. Laboratorio de Productos Naturales, Departamento de Alimentos y Recursos Forestales, Universidad de Los... more
    ... Centro de Productos Naturales Orgánicos “Antonio González” IPNAC-CSIC, La Laguna, Tenerife, Canary Islands, Spain. Emir Valencia. Laboratorio de Productos Naturales, Departamento de Alimentos y Recursos Forestales, Universidad de Los ... 3, 88.8, CH, 48.6, CH2, 48.7, CH2 ...
    The absolute configuration (AC) of 6β-hydroxy-3α-senecioyloxytropane (1), 3α-hydroxy-6β-tigloyloxytropane (2), 3α-hydroxy-6β-senecioyloxytropane (3), and 3α-hydroxy-6β-angeloyloxytropane (4) was assigned as (1R,3R,5S,6R) using density... more
    The absolute configuration (AC) of 6β-hydroxy-3α-senecioyloxytropane (1), 3α-hydroxy-6β-tigloyloxytropane (2), 3α-hydroxy-6β-senecioyloxytropane (3), and 3α-hydroxy-6β-angeloyloxytropane (4) was assigned as (1R,3R,5S,6R) using density functional theory (DFT) calculations at the B3LYP/DGDZVP level of theory in combination with experimental vibrational circular dichroism (VCD) measurements and comparison with the spectra of similar tropanes. The AC of 1 followed from a sample isolated from Schizanthus grahamii, while
    ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select... more
    ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    Silphinene sesquiterpenes are established chrysomelid antifeedants. In this work, nine silphinene analogs, 11beta-acetoxy-5alpha-angeloyloxysilphinen-3-one (1), 11beta-acetoxy-5alpha-tigloyloxysilphinen-3-one (2),... more
    Silphinene sesquiterpenes are established chrysomelid antifeedants. In this work, nine silphinene analogs, 11beta-acetoxy-5alpha-angeloyloxysilphinen-3-one (1), 11beta-acetoxy-5alpha-tigloyloxysilphinen-3-one (2), 11beta-acetoxy-5alpha-isobutyryloxysilphinen-3-one (3), 11beta-hydroxy-5alpha-angeloyloxysilphinen-3-one (4), 11beta,5alpha-dihydroxysilphinen-3-one (5), 11beta,5alpha-diacetoxysilphinen-3-one (6), 5alpha,11beta-diisobutyryloxysilphinen-3-one (7), silphinen-3,5,11-trione (8), and O-methyl-5-epicantabrenolic acid methyl ester (10), and a presilphiperfolane sesquiterpene (9) were tested against several divergent insect species, including the lepidopteran Spodoptera littoralis, the chrysomelid Leptinotarsa decemlineata, and five aphid species, and their antifeedant effects were compared with those of picrotoxinin, a GABA-antagonist, and thymol, an allosteric modulator for insect GABA receptors. All insects tested responded to at least one silphinene analog and/or GABA antagon...
    A new bioactive eremophilanolide, 1alpha-tigloyloxy-8betaH,10betaH-eremophil-7(11)-en-8alpha,12-olide, was isolated from Senecio poepigii and its structure was elucidated by spectral analysis.... more
    A new bioactive eremophilanolide, 1alpha-tigloyloxy-8betaH,10betaH-eremophil-7(11)-en-8alpha,12-olide, was isolated from Senecio poepigii and its structure was elucidated by spectral analysis. 1alpha-Angeloyloxy-8beta-methoxy-10betaH-eremophil-7(11)-en-8alpha,12-olide was also isolated. Antifungal and insect antifeedant properties were evaluated.
    The new sesquiterpenes, 5alpha-senecioyloxysilphinen-3-one (5), 5alpha-tigloyloxysilphinen-3-one (7), and 3beta-hydroxy-5alpha-angeloyloxysilphinene (8), and the known compounds (6S)-2,10-bisaboladien-1-one (1),... more
    The new sesquiterpenes, 5alpha-senecioyloxysilphinen-3-one (5), 5alpha-tigloyloxysilphinen-3-one (7), and 3beta-hydroxy-5alpha-angeloyloxysilphinene (8), and the known compounds (6S)-2,10-bisaboladien-1-one (1), 6,7-epoxy-3(15)-caryophyllene (2), 6,7-epoxy-2,9-humuladiene (3), 5alpha-angeloyloxysilphinen-3-one (4), and 5alpha-acetoxysilphinen-3-one (6) were isolated from bioactive fractions of Senecio palmensis. The structures of these compounds were established by spectroscopic analysis and chemical evidence. The semisynthetic analogues silphinen-3,5-dione (9), 5alpha-hydroxysilphinen-3-one (10), 5beta-hydroxysilphinen-3-one (11), 5beta-acetoxysilphinen-3-one (12), and 5beta-isobutyryloxysilphinen-3-one (13) were generated to carry out a structure-activity study on the antifeedant action of these molecules against several divergent insect species.
    A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8β-hydroxy-african-4(5)-en-3-one... more
    A chemical study of Bethencourtia hermosae, aerial parts and in vitro root cultures, transformed by Agrobacterium rhizogenes, afforded the hitherto unreported sesquiterpenes ceratopicanol angelate (1), 8β-hydroxy-african-4(5)-en-3-one tiglate (4), 8β-hydroxy-african-4(5)-en-3-one 3'-angeloxy-2'-methylbutanoate (5), 1α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (7) and 6α,8β-dihydroxy-african-4(5)-en-3-one 8β-angelate (8). In addition, 8β-hydroxy-african-4(5)-en-3-one (6) was isolated for the first time from a natural source, along with the rare sesquiterpenoid senecrassidiol (10) and two jacaranone derivatives 14 and 16. Known pyrrolizidine alkaloids, together with previously unreported hermosine (23), have also been isolated from this plant. The insect antifeedant activities of the extracts and compounds were studied together with their cytotoxic effects against insect (Sf9) and mammalian (CHO) cell lines.
    ABSTRACT Senecio species have been used in folk medicine for treatment of wounds, as antiemetic, anti-inflammatory and their crude extract or dry powder as crop protection agents. The toxicity exhibited to livestock by these plants has... more
    ABSTRACT Senecio species have been used in folk medicine for treatment of wounds, as antiemetic, anti-inflammatory and their crude extract or dry powder as crop protection agents. The toxicity exhibited to livestock by these plants has been attributed to their content in pyrrolizidine alkaloids and furanoeremophilane type sesquiterpenes. Sesquiterpenoids with eremophilane, cacalol, bisabolane, silphinene, caryophillane, humulane, germacrane and benzofurane skeletons have been isolated from this genus. Here we focus on bioactive sesquiterpenoids with plant defensive properties isolated from Senecio.
    Three new tropanol dimers of mesaconic and itaconic acids and 3α-senecioyloxytropane, together with other known alkaloids, were isolated from Schizanthus grahamii. The structures of the new compounds were established by spectroscopic and... more
    Three new tropanol dimers of mesaconic and itaconic acids and 3α-senecioyloxytropane, together with other known alkaloids, were isolated from Schizanthus grahamii. The structures of the new compounds were established by spectroscopic and chemical transformations including ...
    A new bioactive eremophilanolide, 1alpha-tigloyloxy-8betaH,10betaH-eremophil-7(11)-en-8alpha,12-olide, was isolated from Senecio poepigii and its structure was elucidated by spectral analysis.... more
    A new bioactive eremophilanolide, 1alpha-tigloyloxy-8betaH,10betaH-eremophil-7(11)-en-8alpha,12-olide, was isolated from Senecio poepigii and its structure was elucidated by spectral analysis. 1alpha-Angeloyloxy-8beta-methoxy-10betaH-eremophil-7(11)-en-8alpha,12-olide was also isolated. Antifungal and insect antifeedant properties were evaluated.

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