Thermlanseedlines A-G, seven thermopsine-based alkaloids with antiviral and insecticidal activities from the seeds of Thermopsis lanceolata R. Br

Peng Zhang; Qiao An; Ping Yi; Yue Cui; Ji-Bin Zou; Chun-Mao Yuan; Yu Zhang; Wei Gu; Lie-Jun Huang; Li-Hua Zhao; Zhan-Xing Hu; Xiao-Jiang Hao

doi:10.1016/j.fitote.2022.105140

Thermlanseedlines A-G, seven thermopsine-based alkaloids with antiviral and insecticidal activities from the seeds of Thermopsis lanceolata R. Br

Fitoterapia. 2022 Apr:158:105140. doi: 10.1016/j.fitote.2022.105140. Epub 2022 Feb 2.

Authors

Peng Zhang¹, Qiao An², Ping Yi², Yue Cui³, Ji-Bin Zou², Chun-Mao Yuan², Yu Zhang⁴, Wei Gu², Lie-Jun Huang², Li-Hua Zhao⁵, Zhan-Xing Hu⁶, Xiao-Jiang Hao⁷

Affiliations

¹ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, PR China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550002, PR China; School of Pharmacy, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, China.
² State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, PR China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550002, PR China.
³ The Institute of Biotechnology and Germplasm Resources, Yunnan Academy of Agricultural Sciences, Kunming 650204, PR China.
⁴ State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming 650201, PR China.
⁵ The Institute of Biotechnology and Germplasm Resources, Yunnan Academy of Agricultural Sciences, Kunming 650204, PR China. Electronic address: 356429686@qq.com.
⁶ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, PR China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550002, PR China. Electronic address: huzhxi88@163.com.
⁷ State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, PR China; The Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guiyang 550002, PR China; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Science, Kunming 650201, PR China. Electronic address: haoxj@mail.kib.ac.cn.

PMID: 35122885
DOI: 10.1016/j.fitote.2022.105140

Abstract

Seven undescribed thermopsine-based alkaloids (1-7), including one undescribed biogenetically related intermediate (7), were isolated from the seeds of Thermopsis lanceolata R. Br. Compound 1 possessed a 6/6-6 tricyclic skeleton, while compounds 2-6 represented three rare dimerization patterns constructed by quinolizidine alkaloids. Their structures were elucidated by comprehensive spectroscopic data analysis as well as ECD calculations. Biologically, compound 6 displayed significant anti-Tomato spotted wilt virus (TSWV) activity compared with the positive control ningnanmycin. Moreover, compound 1 exhibited good insecticidal activity against Aphis fabae with LC₅₀ value of 25.2 mg/L.

Keywords: Anti-TSMV; Insecticidal activity; Quinolizidine alkaloids; Thermopsis lanceolata R. Br..

MeSH terms

Alkaloids* / chemistry
Antiviral Agents / chemistry
Antiviral Agents / pharmacology
Insecticides* / chemistry
Insecticides* / pharmacology
Molecular Structure
Seeds / chemistry

Substances

Alkaloids
Antiviral Agents
Insecticides