Quinolizidine Alkaloids with Antiviral and Insecticidal Activities from the Seeds of Sophora tonkinensis Gagnep

Abstract

The discovery of novel, effective, and botanical pesticides is one of the main strategies for modern plant protection and insect pest control. During the search for novel botanical pesticides from natural sources, the seeds of Sophora tonkinensis were systematically investigated to obtain 11 new matrine-type alkaloids (1–11), including one novel matrine-type alkaloid featuring an unprecedented 5/6/6/6 tetracyclic skeleton (1), along with 16 known compounds (12–27). Their structures were elucidated by comprehensive spectroscopic data analysis (IR, UV, NMR, and HRESIMS), ECD calculations, and single-crystal X-ray diffraction. The anti-tobacco mosaic virus (TMV) activity and insecticidal activities against Aphis fabae and Tetranychus urticae of the compounds were also respectively screened using the half-leaf method and spray method. Biological tests indicated that compounds 2, 4, 6, and 26 displayed significant anti-TMV biological activities compared with the positive control ningnanmycin. Compounds 7, 17, and 26 presented moderate activities against A. fabae with LC50 values of 38.29, 18.63, and 23.74 mg/L, respectively. Moreover, compounds 13 and 26 exhibited weak activities against T. urticae.

Unraveling the Biosynthesis of Quinolizidine Alkaloids Using the Genetic and Chemical Diversity of Mexican Lupins

“…Each lupin species produces a characteristic pattern of QAs with few major compounds and several others as traces [2][3][4]. The chemical properties and insecticidal, antimicrobial, and medicinal activities of QAs are of interest in the chemical, biotechnological, and pharmaceutical industries [5][6][7][8][9][10][11][12][13][14][15].…”

Sophaloseedlines A—G: Diverse Matrine‐Based Alkaloids from Sophora alopecuroides with Potential Anti‐Hepatitis B Virus Activities

“…The aforementioned information together with biosynthetic reasoning suggested compound 1 possessed the rearranged tetracyclic fused ring of matrine‐based skeleton. [ 4,13 ]…”

“…MT or SRI underwent a series of selective oxidation and reduction to produce intermediate A1 — A3 , and 5‐hydroxy‐6,7‐dehydromatrine, which was obtained from the title plant previously. [ 13 ] Biogenetic‐ related precursor 10‐oxy‐5,6‐dehydromatrine [ 3 ] further provided evidence of the existence of intermediates A2 and A3 . Subsequent oxidation of the double bond of C‐5—C‐6 or C‐6—C‐7 in A1 — A3 and 5‐hydroxy‐6,7‐dehydro‐matrine would yield compounds 6 , 8 , 9 and A4 .…”

“…[ 3‐5 ] Most of matrine‐type alkaloids exhibited diverse bioactivities, such as analgesic, [ 6 ] anti‐ tumor, [ 7 ] anti‐inflammatory, [ 8‐10 ] and promising antiviral activities. [ 2‐4,6,11‐13 ] Due to the complex stereo‐structures and multiple biological properties, matrine‐type alkaloids are increasingly regarded as attractive targets for both chemists and pharmacologists. [ 14‐16 ]…”

Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects

“…Previous phytochemical investigations on S. alopecuroides revealed alkaloids as one of principal active chemical constituents. Among them, matrine-type alkaloids exhibit diverse bioactivities such as antiviral ( Zou et al, 2020 ), anti-insect ( Huang et al, 2017 ), anti-tumor ( Li et al, 2020 ), and promising anti-inflammatory activities ( Huang et al, 2016 ; Li et al, 2020 ).…”