Four undescribed pyrethrins from seeds of Pyrethrum cinerariifolium and their aphidicidal activity

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL Natural Products and Bioprospecting Pub Date : 2023-07-07 DOI:10.1007/s13659-023-00385-0

Hao-Ran Zhou, Li-Wu Lin, Zhong-Rong Li, Xing-Rong Peng, Ming-Hua Qiu

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Abstract

Four undescribed pyrethrins C-F (1–4) as well as four known pyrethrins (5–8) were isolated from seeds of Pyrethrum cinerariifolium Trev. The structures of compounds 1–4 were elucidated by UV, HRESIMS, and NMR (¹H and ¹³C NMR, ¹H-¹H COSY, HSQC, HMBC and ROESY), among which the stereostructure of compound 4 was determined by calculated ECD. Furthermore, compounds 1–4 were evaluated for their aphidicidal activities. The insecticidal assay results showed that 1–4 exhibited moderate aphidicidal activities at the concentration of 0.1 mg/mL with the 24 h mortality rates ranging from 10.58 to 52.98%. Among them, pyrethrin D (2) showed the highest aphidicidal activity, with the 24 h mortality rate of 52.98%, which was slightly lower than the positive control (pyrethrin II, 83.52%).

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除虫菊种子中4种未描述的除虫菊酯及其杀虫活性

从除虫菊种子中分离到4个未描述的除虫菊酯C-F(1-4)和4个已知的除虫菊酯(5-8)。化合物1 ~ 4的结构通过UV、HRESIMS和NMR (1H和13C NMR、1H-1H COSY、HSQC、HMBC和ROESY)进行了解析，其中化合物4的立体结构通过计算ECD进行了确定。此外，对化合物1 ~ 4的杀蚜活性进行了评价。杀虫试验结果表明，1 ~ 4在浓度为0.1 mg/mL时具有中等杀虫活性，24 h死亡率为10.58% ~ 52.98%。其中，除虫菊酯D(2)的杀虫活性最高，24 h死亡率为52.98%，略低于阳性对照(除虫菊酯II)的83.52%。图形抽象

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