Stoechanones A and B, Phytotoxic Copaane Sesquiterpenoids Isolated from Lavandula stoechas with Potential Herbicidal Activity against Amaranthus retroflexus.,Journal of Natural Products

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Stoechanones A and B, Phytotoxic Copaane Sesquiterpenoids Isolated from Lavandula stoechas with Potential Herbicidal Activity against Amaranthus retroflexus.
Journal of Natural Products ( IF 3.3 ) Pub Date : 2020-05-08 , DOI: 10.1021/acs.jnatprod.0c00182
Marco Masi ₁ , Euro Pannacci ₂ , Ernesto Santoro ₃ , Nadjia Zermane ₄ , Stefano Superchi ₃ , Antonio Evidente ₁

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From the organic extract of Lavandula stoechas, a Mediterranean native plant species, two new phytotoxic copaane sesquiterpenoids were isolated and named stoechanones A and B (1 and 2). They were obtained together with the methyl esters of caffeic and p-coumaric acids and the flavonoid apigenin (3-5, respectively). The structures of stoechanones A and B were determined by spectroscopic (essentially 1D and 2D 1H and 13C NMR and HRESIMS) and chemical methods, and they were characterized as 9,10-dihydroxy-8-isopropyl-1,5-dimethyltricyclo[4.4.0.02.7]dec-4-en-3-one and its 9-O-acetyl derivative. Their relative configurations were assigned by NOESY experiments, and the absolute configurations by comparison of the experimental and DFT-computed ECD spectra. When assayed through Petri dish bioassays, both stoechanones A and B showed phytotoxic effects against seed germination and seedling growth of Amaranthus retroflexus, strongly inhibiting seed germination percentage and radicle and hypocotyl lengths of seedlings. Owing to the herbicidal activity toward A. retroflexus, these two new tricyclic sesquiterpenoids could be proposed and developed as natural bioherbicides in order to increase the control of this problematic weed in the future.

中文翻译：

Stoechanones A 和 B，从 Lavandula stoechas 中分离出的植物毒性 Copaane 倍半萜类化合物，对 Amaranthus retroflexus 具有潜在的除草活性。

从地中海本地植物物种 Lavandula stoechas 的有机提取物中分离出两种新的具有植物毒性的 copaane 倍半萜类化合物，并将其命名为 stoechanones A 和 B（1 和 2）。它们与咖啡酸和对香豆酸的甲酯以及黄酮类芹菜素（分别为 3-5）一起获得。通过光谱（基本上是一维和二维 1H 和 13C NMR 和 HRESIMS）和化学方法确定了 stoechanones A 和 B 的结构，它们被表征为 9,10-二羟基-8-异丙基-1,5-二甲基三环[4.4。 0.02.7]dec-4-en-3-one 及其 9-O-乙酰基衍生物。它们的相对构型由 NOESY 实验指定，绝对构型通过实验和 DFT 计算的 ECD 光谱的比较来指定。当通过培养皿生物测定进行测定时，stoechanones A 和 B 均显示出对苋菜种子萌发和幼苗生长的植物毒性作用，强烈抑制种子萌发率和幼苗的胚根和下胚轴长度。由于对 A. retroflexus 的除草活性，这两种新的三环倍半萜类化合物可以被提议和开发为天然生物除草剂，以在未来增加对这种有问题的杂草的控制。

更新日期：2020-05-08

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