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Title

Alkane-, alkene-, alkyne-γ-lactones and ryanodane diterpenes from aeroponically grown Persea indica roots

AuthorsFraga, Braulio M. ; Díaz, Carmen E. ; Bolaños, Patricia; Bailén, María; Andrés, María Fe; González-Coloma, Azucena
KeywordsPersea indica
Lauraceae
Aeroponic cultures
Alkyl-γ-lactones
Isomajorynolide
Avocadynone acetate
Monoterpenes
(−)-Borneol esters
Diterpenes
Ryanodanes
Biological activity
Issue Date1-Aug-2020
PublisherElsevier
CitationPhytochemistry 176: 112398 (2020)
AbstractThis 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.
Publisher version (URL)https://doi.org/10.1016/j.phytochem.2020.112398
URIhttp://hdl.handle.net/10261/212178
DOI10.1016/j.phytochem.2020.112398
ISSN0031-9422
E-ISSN1873-3700
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(IPNA) Artículos
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