Adriana Portero - Academia.edu (original) (raw)
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Papers by Adriana Portero
Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpig... more Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpignan (Francia) del 24 al 26 de septiembre de 2014.
As part of our ongoing chemical and biotechnological research on the sustainable production of na... more As part of our ongoing chemical and biotechnological research on the sustainable production of natural agrochemicals from Canary endemic species, we have selected two Pericallis (Asteraceae) species, an endemic genus from the Macaronesian region found in the Canary Islands, Madeira and Azores. This genus has been recently separated from Senecio, a well-known source of sesquiterpenes, diterpenes and pyrrolizidine alkaloids. In this work we have studied the chemical defenses of P. echinata, a species from Tenerife with a strict environmental conditions habitat and P. hadrosoma, an extremely endangered species from Gran Canaria. We have adapted P. echinata to aeroponic culture (aerial part and roots) and both species to in vitro culture of transformed roots, allowing for the sustainable production of benzofuranes and diterpenes. Extracts from biotechnological cultures and aerial extracts of the wild plants were investigated for comparative purposes. The extracts were fractionated by chromatographic techniques and the structures of isolated compounds were elucidated by mono and bidimensional NMR spectroscopic techniques, chemical correlation and comparison with bibliographic data. Fifty-nine compounds have been isolated from P. echinata and P. hadrosoma and ten are reported for the first time as new natural products. The phytochemical study of P. echinata resulted in the isolation of two new natural compounds, 10,11-dihydroxy-12-angeloxyeuparine (10) and 2,4-dihydroxy-5-formyl-acetophenone (30), thirteen benzofuranes, two aromatic compounds, six triterpenes, five sterols and four pyrrolizidine alkaloids. The study of P. hadrosoma gave four nor-sesquiterpenoids, twenty-two diterpenes, mostly with ent-kaurane skeleton, including the new compounds pericanoic acid (47), pericatriol (49), hadrosomic acid (50), perihadrosonol (51), pericalloic-A acid (53), pericalloic-B acid (53a), pericaldehide (57); two sterols and five pyrrolizidine alkaloids with (+)-neoplatyphilline (67) being described here for the first time. We have also investigated the biotransformation by Mucor plumbeus of 6-hydroxytremetone, a benzofurane from P. echinata, yielding new glycosylated derivatives. The ethanolic crude extracts, their fractions and isolated metabolites were bioassayed against different crop pests including insects (Spodoptera littoralis, Leptinotarsa decemlineata, Myzus persicae, Rhopalosiphum padi) and the nematode Meloidogyne javanica. Also their phytotoxic effects were tested on Lactuca sativa and Lolium perenne. Some benzofuranes from P. echinata were antifeedant against insects, mainly to the lepidopterous S. littoralis and the aphid M. persicae (5, 13, 1 and 12). Some showed phytotoxic effects (1, 6 and 11). P. hadrosoma, contained ent-kaurane diterpenes that promoted plant growth (43 and 51) and nor-sesquiterpenes with phytotoxic effects (40, 42, 46a and 50). Drosophila melanogaster was used as a ?taste detection model?, to test if natural products with deterrent activity on Spodoptera littoralis (benzofuranes 1, 6 and 12) could be related with a repulsive response due to their bitter taste. With this aim, behavior experiments (MultiCAFE, feeding color test, PER) and electrophysiological recordings were reported. Our initial results suggest that eupachinin (4) was the only molecule which had an aversive effect on Drosophila with an inhibitory effect on sugar detection (s-cell). We also tested the cytotoxic activity against different tumour cell lines of ent-kauranes from P. hadrosoma. Some of these compounds (40, 43, 44 and 50) showed promising activity against different tumour cell lines, especially on HCT116 colorectal carcinoma cells.
Phytochemistry Reviews, Dec 1, 2012
ABSTRACT Senecio species have been used in folk medicine for treatment of wounds, as antiemetic, ... 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.
As part of our ongoing chemical and biotechnological research on the sustainable production of na... more As part of our ongoing chemical and biotechnological research on the sustainable production of natural agrochemicals from Canary endemic species, we have selected two Pericallis (Asteraceae) species, an endemic genus from the Macaronesian region found in the Canary Islands, Madeira and Azores. This genus has been recently separated from Senecio, a well-known source of sesquiterpenes, diterpenes and pyrrolizidine alkaloids. In this work we have studied the chemical defenses of P. echinata, a species from Tenerife with a strict environmental conditions habitat and P. hadrosoma, an extremely endangered species from Gran Canaria. We have adapted P. echinata to aeroponic culture (aerial part and roots) and both species to in vitro culture of transformed roots, allowing for the sustainable production of benzofuranes and diterpenes. Extracts from biotechnological cultures and aerial extracts of the wild plants were investigated for comparative purposes. The extracts were fractionated by ch...
Phytochemistry Reviews, 2012
ABSTRACT Senecio species have been used in folk medicine for treatment of wounds, as antiemetic, ... 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.
Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpig... more Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpignan (Francia) del 24 al 26 de septiembre de 2014.
Phytochemistry, 2013
Artemisia granatensis, an endemic endangered plant species from Sierra Nevada (Spain) has been su... more Artemisia granatensis, an endemic endangered plant species from Sierra Nevada (Spain) has been successfully cultivated in artificial systems (plants in artificial soil and transformed in vitro roots) to generate enough plant biomass (aerial and root) to allow for its chemical and biological study and at the same time to provide with methods for the sustainable production of the plant and its metabolites. A eudesmanolide (17) along with six sesquiterpenes (11-16), nine monoterpenes (2-10), one nor-monoterpene (1), three acetylenic spiroacetal enoleters (18-20) and one coumarin (21) have been identified from the aerial plant ethanolic extract. Acetylenic spiroacetal enoleters 18-19 and coumarins 21-23 have been isolated from the transformed root ethanolic extract. These extracts and some isolated compounds or mixtures of them have been tested for their insect antifeedant effects against Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi. Significant antifeedant properties were determined for the aerial plant extract, spiroacetals 19-20 and secoguaianolides 13+14 and 16.
Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpig... more Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpignan (Francia) del 24 al 26 de septiembre de 2014.
As part of our ongoing chemical and biotechnological research on the sustainable production of na... more As part of our ongoing chemical and biotechnological research on the sustainable production of natural agrochemicals from Canary endemic species, we have selected two Pericallis (Asteraceae) species, an endemic genus from the Macaronesian region found in the Canary Islands, Madeira and Azores. This genus has been recently separated from Senecio, a well-known source of sesquiterpenes, diterpenes and pyrrolizidine alkaloids. In this work we have studied the chemical defenses of P. echinata, a species from Tenerife with a strict environmental conditions habitat and P. hadrosoma, an extremely endangered species from Gran Canaria. We have adapted P. echinata to aeroponic culture (aerial part and roots) and both species to in vitro culture of transformed roots, allowing for the sustainable production of benzofuranes and diterpenes. Extracts from biotechnological cultures and aerial extracts of the wild plants were investigated for comparative purposes. The extracts were fractionated by chromatographic techniques and the structures of isolated compounds were elucidated by mono and bidimensional NMR spectroscopic techniques, chemical correlation and comparison with bibliographic data. Fifty-nine compounds have been isolated from P. echinata and P. hadrosoma and ten are reported for the first time as new natural products. The phytochemical study of P. echinata resulted in the isolation of two new natural compounds, 10,11-dihydroxy-12-angeloxyeuparine (10) and 2,4-dihydroxy-5-formyl-acetophenone (30), thirteen benzofuranes, two aromatic compounds, six triterpenes, five sterols and four pyrrolizidine alkaloids. The study of P. hadrosoma gave four nor-sesquiterpenoids, twenty-two diterpenes, mostly with ent-kaurane skeleton, including the new compounds pericanoic acid (47), pericatriol (49), hadrosomic acid (50), perihadrosonol (51), pericalloic-A acid (53), pericalloic-B acid (53a), pericaldehide (57); two sterols and five pyrrolizidine alkaloids with (+)-neoplatyphilline (67) being described here for the first time. We have also investigated the biotransformation by Mucor plumbeus of 6-hydroxytremetone, a benzofurane from P. echinata, yielding new glycosylated derivatives. The ethanolic crude extracts, their fractions and isolated metabolites were bioassayed against different crop pests including insects (Spodoptera littoralis, Leptinotarsa decemlineata, Myzus persicae, Rhopalosiphum padi) and the nematode Meloidogyne javanica. Also their phytotoxic effects were tested on Lactuca sativa and Lolium perenne. Some benzofuranes from P. echinata were antifeedant against insects, mainly to the lepidopterous S. littoralis and the aphid M. persicae (5, 13, 1 and 12). Some showed phytotoxic effects (1, 6 and 11). P. hadrosoma, contained ent-kaurane diterpenes that promoted plant growth (43 and 51) and nor-sesquiterpenes with phytotoxic effects (40, 42, 46a and 50). Drosophila melanogaster was used as a ?taste detection model?, to test if natural products with deterrent activity on Spodoptera littoralis (benzofuranes 1, 6 and 12) could be related with a repulsive response due to their bitter taste. With this aim, behavior experiments (MultiCAFE, feeding color test, PER) and electrophysiological recordings were reported. Our initial results suggest that eupachinin (4) was the only molecule which had an aversive effect on Drosophila with an inhibitory effect on sugar detection (s-cell). We also tested the cytotoxic activity against different tumour cell lines of ent-kauranes from P. hadrosoma. Some of these compounds (40, 43, 44 and 50) showed promising activity against different tumour cell lines, especially on HCT116 colorectal carcinoma cells.
Phytochemistry Reviews, Dec 1, 2012
ABSTRACT Senecio species have been used in folk medicine for treatment of wounds, as antiemetic, ... 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.
As part of our ongoing chemical and biotechnological research on the sustainable production of na... more As part of our ongoing chemical and biotechnological research on the sustainable production of natural agrochemicals from Canary endemic species, we have selected two Pericallis (Asteraceae) species, an endemic genus from the Macaronesian region found in the Canary Islands, Madeira and Azores. This genus has been recently separated from Senecio, a well-known source of sesquiterpenes, diterpenes and pyrrolizidine alkaloids. In this work we have studied the chemical defenses of P. echinata, a species from Tenerife with a strict environmental conditions habitat and P. hadrosoma, an extremely endangered species from Gran Canaria. We have adapted P. echinata to aeroponic culture (aerial part and roots) and both species to in vitro culture of transformed roots, allowing for the sustainable production of benzofuranes and diterpenes. Extracts from biotechnological cultures and aerial extracts of the wild plants were investigated for comparative purposes. The extracts were fractionated by ch...
Phytochemistry Reviews, 2012
ABSTRACT Senecio species have been used in folk medicine for treatment of wounds, as antiemetic, ... 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.
Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpig... more Trabajo presentado en el European Congress on Natural Products and Biocontrol celebrado en Perpignan (Francia) del 24 al 26 de septiembre de 2014.
Phytochemistry, 2013
Artemisia granatensis, an endemic endangered plant species from Sierra Nevada (Spain) has been su... more Artemisia granatensis, an endemic endangered plant species from Sierra Nevada (Spain) has been successfully cultivated in artificial systems (plants in artificial soil and transformed in vitro roots) to generate enough plant biomass (aerial and root) to allow for its chemical and biological study and at the same time to provide with methods for the sustainable production of the plant and its metabolites. A eudesmanolide (17) along with six sesquiterpenes (11-16), nine monoterpenes (2-10), one nor-monoterpene (1), three acetylenic spiroacetal enoleters (18-20) and one coumarin (21) have been identified from the aerial plant ethanolic extract. Acetylenic spiroacetal enoleters 18-19 and coumarins 21-23 have been isolated from the transformed root ethanolic extract. These extracts and some isolated compounds or mixtures of them have been tested for their insect antifeedant effects against Spodoptera littoralis, Myzus persicae and Rhopalosiphum padi. Significant antifeedant properties were determined for the aerial plant extract, spiroacetals 19-20 and secoguaianolides 13+14 and 16.