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突尼斯生长的南洋杉树脂精油馏分的化学成分、驱避和植物毒性潜力。

Chemical Composition, Repellent, and Phytotoxic Potentials of the Fractionated Resin Essential Oil from Araucaria heterophylla Growing in Tunisia.

机构信息

Laboratory of Heterocyclic Chemistry, Natural Products and Reactivity (LR11ES39), Team: Medicinal Chemistry and Natural Products, Faculty of Science of Monastir, University of Monastir, Avenue of Environment, 5019, Monastir, Tunisia Phone.

Dipartimento di Farmacia, Università di Pisa, Via Bonanno 6, 56126, Pisa, Italy.

出版信息

Chem Biodivers. 2024 May;21(5):e202400185. doi: 10.1002/cbdv.202400185. Epub 2024 Apr 22.

Abstract

The resin essential oil (REO) of the Tunisian Araucaria heterophylla trunk bark was investigated for its chemical composition. Then, it was evaluated for its insecticidal and allelopathic activities. The REO was obtained by hydrodistillation for 9 h (yield of 4.2 % w/w). Moreover, fractional hydrodistillation was carried out at 3-hour intervals, resulting in 3 fractions (R-R), to facilitate chemical identification and localization of the aforementioned biological activities. GC/MS analysis of the obtained samples allowed the identification of 25 compounds, representing between 91.2 and 96.3 % of their total constituents, which consisted predominantly of sesquiterpene hydrocarbons, oxygenated sesquiterpenes and diterpene hydrocarbons. α-Copaene (10.8 %), γ-muurolene (5.8 %), α-copaen-11-ol (7.8 %), spathulenol (10.5 %), 15-copaenol (8.2 %), ylangenal (10.3 %), dehydrosaussurea lactone (7.7 %), and sandaracopimaradiene (11.4 %) were identified as major compounds. The second part aimed to assess the impact of the A. heterophylla EO and its three fractions for their insecticidal and repellent activity against Tribolium castaneum (Herbst), a stored grain pest, of which a strong repellent activity was noted. In addition, the studied samples showed high phytotoxic effects against Lactuca sativa. The third fraction (R) performed a total inhibitory potential on seed germination and seedling growth of the target plant. Furthermore, alongside this discovery, an estimation was conducted through molecular docking analysis. Wherein the main compounds of the studied samples were docked into the active pocket of protoporphyrinogen IX oxidase (PDB: 1SEZ), a key enzyme in chlorophyll biosynthesis. Thus, it is recommended to use the REO of A. heterophylla as a natural herbicide.

摘要

对突尼斯南洋杉树干皮的树脂精油(REO)的化学成分进行了研究。然后,评估了它的杀虫和化感活性。REO 通过 9 小时的水蒸馏获得(产率为 4.2%w/w)。此外,每 3 小时进行一次分馏水蒸馏,得到 3 个馏分(R-R),以促进化学鉴定和定位上述生物活性。对获得的样品进行 GC/MS 分析,鉴定出 25 种化合物,占其总成分的 91.2%至 96.3%,主要由半萜烯烃、含氧半萜烯和二萜烯烃组成。α-可巴烯(10.8%)、γ-杜松烯(5.8%)、α-可巴烯-11-醇(7.8%)、spathulenol(10.5%)、15-可巴烯醇(8.2%)、ylangenal(10.3%)、脱水沙松内酯(7.7%)和沙达松脂二萜(11.4%)被鉴定为主要化合物。第二部分旨在评估南洋杉 EO 及其三个馏分对谷蠹(Tribolium castaneum(Herbst))的杀虫和驱避活性的影响,谷蠹是一种储粮害虫,表现出很强的驱避活性。此外,研究样品对莴苣表现出很高的植物毒性。第三馏分(R)对目标植物的种子发芽和幼苗生长表现出完全的抑制潜力。此外,在这一发现的基础上,通过分子对接分析进行了估计。其中,研究样品的主要化合物被对接进入原卟啉原氧化酶 IX(PDB:1SEZ)的活性口袋,原卟啉原氧化酶 IX 是叶绿素生物合成的关键酶。因此,建议将南洋杉的 REO 用作天然除草剂。

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