Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots
This work presents the study of the roots of the Macaronesian paleoendemism Persea indica (L.) Spreng. The root biomass of this protected tree species has been produced by soil-less aeroponic culture under controlled environment. This system has important advantages over traditional plant production techniques because it provides opportunities to optimize the yield of metabolite production under well-controlled conditions, thereby facilitating commercial-scale production of bioactive compounds. Thus, for the first time a study of this type has permitted the isolation from the roots of seven undescribed dextrorotatory lactones: the alkane-γ-lactones (+)-majoranolide and (+)-dihydromajorenolide, the alkene-γ-lactones (+)-majorenolide and (+)-majorenolide acetate, and the alkyne-γ-lactones, (+)-majorynolide, (+)-majorynolide acetate and (+)-isomajorynolide. In addition, thirteen known compounds were also isolated including two possible avocadofurane precursors, avocadynone acetate and avocadenone acetate, the monoterpene esters cis- and trans-p-coumarate of (−)-borneol, and the ryanoid diterpenes cinnzeylanone, anhidrocinnzeylanine, cinnzeylanine, cinnzeylanol, epiryanodol, perseanol, cinncassiol E, perseaindicol and secoperseanol. The configuration at C-14 de two ryanodane diterpenes has also been revised in this work. Furthermore, (−)-borneol cis-p-coumarate has showed to be insecticidal to S. littoralis and cytotoxic to insect (Sf9) cells, (+)-majorenolide antifeedant to aphids and cytotoxic to Sf9, cinnceylanol antifeedant and insecticidal to S. littoralis, and (+)-majorynolide (2), insecticidal against S. littoralis, cytotoxic to Sf9 and nematicidal, suggesting a defensive role for these compounds.
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Format: | artículo biblioteca |
Language: | English |
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Elsevier
2020-08-01
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Subjects: | Persea indica, Lauraceae, Aeroponic cultures, Alkyl-γ-lactones, Isomajorynolide, Avocadynone acetate, Monoterpenes, (−)-Borneol esters, Diterpenes, Ryanodanes, Biological activities, |
Online Access: | http://hdl.handle.net/10261/212178 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 |
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dig-ipna-es-10261-2121782020-10-13T13:07:32Z Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots Fraga, Braulio M. Díaz, Carmen E. Bolaños, Patricia Bailén, María Andrés, Mª Fé González-Coloma, Azucena Ministerio de Economía y Competitividad (España) European Commission Persea indica Lauraceae Aeroponic cultures Alkyl-γ-lactones Isomajorynolide Avocadynone acetate Monoterpenes (−)-Borneol esters Diterpenes Ryanodanes Biological activities This work presents the study of the roots of the Macaronesian paleoendemism Persea indica (L.) Spreng. The root biomass of this protected tree species has been produced by soil-less aeroponic culture under controlled environment. This system has important advantages over traditional plant production techniques because it provides opportunities to optimize the yield of metabolite production under well-controlled conditions, thereby facilitating commercial-scale production of bioactive compounds. Thus, for the first time a study of this type has permitted the isolation from the roots of seven undescribed dextrorotatory lactones: the alkane-γ-lactones (+)-majoranolide and (+)-dihydromajorenolide, the alkene-γ-lactones (+)-majorenolide and (+)-majorenolide acetate, and the alkyne-γ-lactones, (+)-majorynolide, (+)-majorynolide acetate and (+)-isomajorynolide. In addition, thirteen known compounds were also isolated including two possible avocadofurane precursors, avocadynone acetate and avocadenone acetate, the monoterpene esters cis- and trans-p-coumarate of (−)-borneol, and the ryanoid diterpenes cinnzeylanone, anhidrocinnzeylanine, cinnzeylanine, cinnzeylanol, epiryanodol, perseanol, cinncassiol E, perseaindicol and secoperseanol. The configuration at C-14 de two ryanodane diterpenes has also been revised in this work. Furthermore, (−)-borneol cis-p-coumarate has showed to be insecticidal to S. littoralis and cytotoxic to insect (Sf9) cells, (+)-majorenolide antifeedant to aphids and cytotoxic to Sf9, cinnceylanol antifeedant and insecticidal to S. littoralis, and (+)-majorynolide (2), insecticidal against S. littoralis, cytotoxic to Sf9 and nematicidal, suggesting a defensive role for these compounds. This work has been supported by grant CTQ 2015-64049-C3-1 R, MINECO/FEDER, Spain. Peer reviewed 2020-05-26T08:11:31Z 2020-05-26T08:11:31Z 2020-08-01 artículo http://purl.org/coar/resource_type/c_6501 Phytochemistry 176: 112398 (2020) 0031-9422 http://hdl.handle.net/10261/212178 10.1016/j.phytochem.2020.112398 1873-3700 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 en #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2015-64049-C3-1-R Postprint https://doi.org/10.1016/j.phytochem.2020.112398 Sí none Elsevier |
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Persea indica Lauraceae Aeroponic cultures Alkyl-γ-lactones Isomajorynolide Avocadynone acetate Monoterpenes (−)-Borneol esters Diterpenes Ryanodanes Biological activities Persea indica Lauraceae Aeroponic cultures Alkyl-γ-lactones Isomajorynolide Avocadynone acetate Monoterpenes (−)-Borneol esters Diterpenes Ryanodanes Biological activities |
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Persea indica Lauraceae Aeroponic cultures Alkyl-γ-lactones Isomajorynolide Avocadynone acetate Monoterpenes (−)-Borneol esters Diterpenes Ryanodanes Biological activities Persea indica Lauraceae Aeroponic cultures Alkyl-γ-lactones Isomajorynolide Avocadynone acetate Monoterpenes (−)-Borneol esters Diterpenes Ryanodanes Biological activities Fraga, Braulio M. Díaz, Carmen E. Bolaños, Patricia Bailén, María Andrés, Mª Fé González-Coloma, Azucena Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots |
description |
This work presents the study of the roots of the Macaronesian paleoendemism Persea indica (L.) Spreng. The root biomass of this protected tree species has been produced by soil-less aeroponic culture under controlled environment. This system has important advantages over traditional plant production techniques because it provides opportunities to optimize the yield of metabolite production under well-controlled conditions, thereby facilitating commercial-scale production of bioactive compounds. Thus, for the first time a study of this type has permitted the isolation from the roots of seven undescribed dextrorotatory lactones: the alkane-γ-lactones (+)-majoranolide and (+)-dihydromajorenolide, the alkene-γ-lactones (+)-majorenolide and (+)-majorenolide acetate, and the alkyne-γ-lactones, (+)-majorynolide, (+)-majorynolide acetate and (+)-isomajorynolide. In addition, thirteen known compounds were also isolated including two possible avocadofurane precursors, avocadynone acetate and avocadenone acetate, the monoterpene esters cis- and trans-p-coumarate of (−)-borneol, and the ryanoid diterpenes cinnzeylanone, anhidrocinnzeylanine, cinnzeylanine, cinnzeylanol, epiryanodol, perseanol, cinncassiol E, perseaindicol and secoperseanol. The configuration at C-14 de two ryanodane diterpenes has also been revised in this work. Furthermore, (−)-borneol cis-p-coumarate has showed to be insecticidal to S. littoralis and cytotoxic to insect (Sf9) cells, (+)-majorenolide antifeedant to aphids and cytotoxic to Sf9, cinnceylanol antifeedant and insecticidal to S. littoralis, and (+)-majorynolide (2), insecticidal against S. littoralis, cytotoxic to Sf9 and nematicidal, suggesting a defensive role for these compounds. |
author2 |
Ministerio de Economía y Competitividad (España) |
author_facet |
Ministerio de Economía y Competitividad (España) Fraga, Braulio M. Díaz, Carmen E. Bolaños, Patricia Bailén, María Andrés, Mª Fé González-Coloma, Azucena |
format |
artículo |
topic_facet |
Persea indica Lauraceae Aeroponic cultures Alkyl-γ-lactones Isomajorynolide Avocadynone acetate Monoterpenes (−)-Borneol esters Diterpenes Ryanodanes Biological activities |
author |
Fraga, Braulio M. Díaz, Carmen E. Bolaños, Patricia Bailén, María Andrés, Mª Fé González-Coloma, Azucena |
author_sort |
Fraga, Braulio M. |
title |
Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots |
title_short |
Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots |
title_full |
Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots |
title_fullStr |
Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots |
title_full_unstemmed |
Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots |
title_sort |
alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown persea indica roots |
publisher |
Elsevier |
publishDate |
2020-08-01 |
url |
http://hdl.handle.net/10261/212178 http://dx.doi.org/10.13039/501100000780 http://dx.doi.org/10.13039/501100003329 |
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