Various Bioactivity and Relationship of Structure–Activity of Matrine Analogues

Abstract

For the first time, the botanic source natural product matrine was reported to have more potent inhibitory activity against tobacco mosaic virus (TMV) than the commercial virucide ribavirin. On the basis of the structural diversity modification strategy, a series of matrine derivatives was synthesized and systematically evaluated for their antiviral activity against TMV, fungicidal activity, and insecticidal activity. As a result, compounds 3 (inhibitory rate 67.3%, 69.5%, 63.7%, 63.0% at 500 μg/mL for in vitro activity, inactivation, curative, and protection activities in vivo, respectively), 16 (66.7%, 60.7%, 63.8%, 68.9% at 500 μg/mL), and 32 (74.6%, 76.9%, 72.3%, 75.7% at 500 μg/mL) were found to have much higher anti-TMV activity than ribavirin (40.8%, 37.5%, 38.2%, 37.7% at 500 μg/mL), even exhibiting as well as NK-007 (70.3%, 66.1%, 68.4%, 67.5% at 500 μg/mL), which was an efficient compound created by our group previously. At the same time, it was found that matrine and its derivatives had a broad spectrum fungicidal activity (14 fungi), especially the inhibition of compound 32 against Phytophthora capsici Leonian reached 96.4% at a concentration of 50 μg/mL. What's more, all compounds exhibited very good insecticidal activity to five kinds of insects (including Mythimna Separate, Helicoverpa Armigera, Ostrinia Nubilalis, Plutella xylostella, and Culex Pipiens Pallens); especially, the inhibition rate of C. Pipiens Pallens of compound 22 could still reach 70% at 1 μg/mL.

Leveraging botanical resources for crop protection: the isolation, bioactivity and structure–activity relationships of lycoris alkaloids

“…The synthesis of the compounds 2-17 is shown in Scheme S1 and Schemes 2-5, and the detailed synthetic method and data can be found in Appendix S1. 27…”

“…In our previous exploratory efforts, Cynanchum komarovii ((−)‐antofine), Peganum harmala L. ( β ‐carboline alkaloids), cottonseed (gossypol) and Sophora flavescens (matrine alkaloids) were found to be botanical pesticides with insecticidal, antibacterial and antiviral effects. In this work, the ethanolic extract of L. aurea bulbs, the extracted total alkaloids of L. aurea bulbs and the main alkaloid lycorine (Scheme ) were investigated for their antiviral, antifungal (phytopathogenic), and insecticidal activities.…”

“…12,13 Currently, studies of L. aurea have focused mainly on the discovery of new compounds (mainly alkaloids), [14][15][16][17][18][19] their antitumor properties 20,21 and horticultural research, 22 with only a few studies aiming to explore derived botanical pesticides. 23 In our previous exploratory efforts, Cynanchum komarovii ((−)-antofine), 24 Peganum harmala L. ( -carboline alkaloids), 25 cottonseed (gossypol) 26 and Sophora flavescens (matrine alkaloids) 27 were found to be botanical pesticides with insecticidal, antibacterial and antiviral effects. In this work, the ethanolic extract of L. aurea bulbs, the extracted total alkaloids of L. aurea bulbs and the main alkaloid lycorine (Scheme 1) were investigated for their wileyonlinelibrary.com/journal/ps 2.6 Identification and quantification of lycorine in the fresh L. aurea bulbs 2.6.1 Qualitative analysis The total alkaloids extract (30 mg) was dissolved in 0.1% TFA (15 mL), filtered using a 0.2 m filter and injected (10 L) into the HPLC column.…”

Synthesis, characterization and in vitro biological evaluation of two matrine derivatives

“…However, most researches mainly focused on pharmacological activity, as described above. Comparably, the study on its anti-plant virus activity, fungicidal activity, and insecticidal activity for agricultural use of matrine was not much in the literature 22 .…”

Naamines and Naamidines as Novel Agents against a Plant Virus and Phytopathogenic Fungi

“…In work aimed at developing novel inhibitors of plant viruses from natural products, various natural products with novel structures, such as phenanthroindolizidines [ 15 ], harmine [ 16 ], topsentins [ 17 ], and matrine [ 18 ], have been found to have good antiviral activity. As a continuing work to find novel inhibitors of plant viruses from natural products, we synthesized various naamines, naamidines and derivatives, and systematically investigated their antiviral and antifungal activities.…”