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

• Published in: Phytochemistry (Oxford) Vol. 176; p. 112398
• Main Authors: Fraga, Braulio M., Díaz, Carmen E., Bolaños, Patricia, Bailén, María, Andrés, María Fe, González-Coloma, Azucena
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.08.2020; Elsevier
• Subjects: (−)-Borneol esters; Aeroponic cultures; Alkanes; Alkenes; Alkyl-γ-lactones; Alkynes; Animals; Avocadynone acetate; Biochemistry & Molecular Biology; Biological activity; Diterpenes; Isomajorynolide; Lactones; Lauraceae; Life Sciences & Biomedicine; Monoterpenes; Persea; Persea indica; Plant Roots; Plant Sciences; Ryanodanes; Science & Technology; Alkyl-γ-lactones; (−)-Borneol esters; Ryanodanes; Aeroponic cultures; Persea indica; Diterpenes; Isomajorynolide; Monoterpenes; Lauraceae; Biological activity; Avocadynone acetate; REVISION; OILS; MOLECULAR-STRUCTURE; STEM BARK; Alkyl-gamma-lactones; BUTANOLIDES; INSECT ANTIFEEDANT; (-)-Borneol esters; MAJORENOLIDE; CINNZEYLANOL; RECEPTORS
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2020.112398

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. A phytochemical study of aeroponically grown Persea indica roots has permitted the isolation of several undescribed dextrorotatory alkyl-γ-lactones, two possible avocadofurane precursors, two monotorpene esters, and several ryanodane and isoryanodane diterpenes. Furthermore, we report on the nematicidal and insecticidal activity of these compounds, as well as their cytotoxic effects on insect (Sf9) cells. [Display omitted] •Components from aeroponically grown Persea indica roots.•Alkane-, alkene-, alkyne-γ-lactones, avocadofurane precursors, ryanoid diterpenes.•Nematicidal and insecticidal activity. Cytotoxic effects on insect (Sf9) cells.