Quinolizidine Alkaloids with Antitomato Spotted Wilt Virus and Insecticidal Activities from the Seeds of Thermopsis lanceolata R. Br

Abstract

As part of our ongoing investigation of pesticide active quinolizidine alkaloids (QAs) from the family Fabaceae, the chemical constituents of the seeds of Thermopsis lanceolata R. Br. were systematically investigated. Bioassay-guided fractionation and purification of the crude extract led to the isolation of seventeen new QAs (1−17), including three new naturally occurring compounds (15−17), along with 15 known compounds (18−32). Their structures were elucidated by comprehensive spectroscopic data analysis (IR, UV, NMR, and HRESIMS) and quantum chemistry calculations ( 13 C NMR and ECD). The antitomato spotted wilt virus activities and insecticidal activities against Aphis fabae, Nilaparvata lugens (Stal), and Tetranychus urticae of compounds 1− 32 were screened using the lesion counting method, spray method, and rice-stem dipping method, respectively. Biological tests indicated that compounds 6, 9, 10, and 18 displayed significant anti-TSWV activities compared with the positive control ningnanmycin.

Matrine-Type Alkaloids with Anti-Tomato Spotted Wilt Virus Activity from the Root of Sophora tonkinensis Gagnep.

“…Tested compounds were dissolved in dimethyl sulfoxide and diluted to the required concentration with distilled water. The anti-TSWV activities of 1 – 37 were tested according to the lesion counting method . Moreover, the transcription levels of the TSWV N , NSs , and NSm genes and TSWV NSs protein in the compound-treated leaves were, respectively, detected by qRT–PCR and Western blot for the in vivo curative and protective assays .…”

“…IR (KBr) v max 3375, 2919, 1670, 1567, 1475, 1382 cm −1 . 1 H and 13 C NMR data (CDCl 3 , 600 and 150 MHz) see Tables 3 and 4 Anti-TSWV Assays. Tested compounds were dissolved in dimethyl sulfoxide and diluted to the required concentration with distilled water.…”

“…Quinolizidine alkaloids (QAs, matrine type, aloperine type, cytisine type, anagyrine type, thermopsine type, sparteine type) are characteristic secondary compounds found particularly in the subfamily Papilionoideae of the Fabaceae (Leguminosae) and are especially abundant in the tribes Genisteae , Sophoreae , and Thermopsideae . Many studies have shown that QAs have a wide range of agricultural activities, such as antiviral, insecticidal, and antibacterial activities. − Because of their complex stereostructures and diverse biological effects, QAs have attracted much attention from the scientific communities of natural products and organic synthesis in the past decades. Previously, we found several new matrine-type and cytisine-type alkaloids with antitobacco mosaic virus (TMV) activities from the seeds of Sophora tonkinensis .…”

“…Previously, we found several new matrine-type and cytisine-type alkaloids with antitobacco mosaic virus (TMV) activities from the seeds of Sophora tonkinensis . At the same time, we first reported that several new cytisine-type, thermopsine-type, and anagyrine-type alkaloids from the seeds of Thermopsis lanceolata have good antiviral activities against TSWV . However, the biological activities of matrine-type, aloperine-type, or sparteine-type alkaloids against TSWV have not been reported.…”

“…12 At the same time, we first reported that several new cytisine-type, thermopsine-type, and anagyrine-type alkaloids from the seeds of Thermopsis lanceolata have good antiviral activities against TSWV. 13 However, the biological activities of matrine-type, aloperine-type, or sparteinetype alkaloids against TSWV have not been reported. In our continuing search for novel, highly effective anti-TSWV agents from QAs, a systematic investigation of the root of Sophora tonkinensis Gagnep.…”