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Lansiumamide B
INDUSTRIAL CROPS AND PRODUCTS · 2024 · IF 5.6

Lansiumamide B induced the degradation of polysaccharides and oligosaccharides showing antifungal activity against Rhizoctonia solani

Yina Jia,Jianrong Tang,Yunfu Dang,Yizhou Yang,Shan He,Yue Jiang,Yong Wang,Juntao Feng,Zhiqing Ma,Xili Liu,He Yan

Lansiumamide B (LB) is a cinnamamide alkaloid isolated from Clausena lansium seeds. The compound is the main antifungal ingredient found in C. lansium . In this paper, the antifungal activity of LB against 10 plant pathogenic fungi was evaluated and found that it was the most effective to Rhizoctonia solani (EC 50 = 2.99 μg/mL). The compound also exhibits certain protective (53.06%) and curative (71.01%) activities against R. solani at 800 μg/mL. The mechanism of action of LB was further elucidated through physiological and biochemical experiments, mycelial morphology and ultrastructure observations, and transcriptomics studies with R. solani as the experimental strain. SEM and TEM observation showed that it caused abnormal mycelium growth, extravasation of contents and cell wall degradation. Physiological and biochemical tests showed that LB treatment had no significant effect on the cellular respiration of mycelium , but it could increase the membrane permeability , cause the leakage of intracellular electrolyte, reduce the content of extracellular polysaccharide and chitin in cell wall and increased the contents of intracellular reducing sugar. The results of transcriptome sequencing analysis showed that LB had significant effects on polysaccharide and oligosaccharide related metabolic pathways, such as starch and sucrose metabolic pathways, galactose metabolic pathways, and amino sugar metabolic pathways. Furthermore, LB treatment increased the specific enzyme activity of α-1, 4-glucanase, α-1,6-glucanase, cellulase and maltase of R. solani in vivo . Comprehensive analysis of the above experimental results shows that LB induces and regulates the degradation of polysaccharides and oligosaccharides of R. solani at the transcriptional level, thereby destroying the cell wall structure and ultimately leading to the death of fungi.

研究领域: 植物化学 · 真菌学 · 分子生物学
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PEST MANAGEMENT SCIENCE · 2025 · IF 3.8

Design and synthesis of novel cinnamamide derivatives-based lansiumamide B as potent fungicidal candidates

Yizhou Yang,Jianrong Tang,Tianrun Zhao,Qi Li,Jiuhui Ye,Jing Zhang,Zhiqing Ma,Xili Liu,Xiaojun Chen,He Yan

BACKGROUND Natural products have been and continue to be a significant resource for developing environmentally friendly pesticides with distinctive structures and mechanisms. Lansiumamide B (LB), a cinnamamide compound extracted from Clausena lansium seeds, has served as the lead compound for the design and synthesis of a series of cinnamamide derivatives. The fungicidal activity of these derivatives has been evaluated. RESULTS The majority of the proposed compounds displayed moderate to considerable antifungal efficacy against the tested pathogenic fungi and oomycetes, with some exhibiting broad-spectrum fungicidal activities. Compound B 26 showed excellent activity against Colletotrichum orbiculare in vitro , with a median effective concentration (EC 50 ) value of 0.36 μg/mL, better than positive control boscalid (0.95 μg/mL) and the lead compound LB (60.18 μg/mL). In vivo , B 26 also exhibited greater fungicidal activity against C. orbiculare than boscalid and LB. Furthermore, the study found that the mycelium cell wall was damaged after treatment with compound B 26 through observation of the mycelial morphology and ultrastructure of C. orbiculare . Consequently, mycelial growth was inhibited. CONCLUSION The results indicated that cinnamamide compounds containing a 1,2,3,4-tetrahydroisoquinoline moiety represent a novel class of antifungal active scaffold, and compound B 26 has the potential to be developed into a new type of fungicide. © 2025 Society of Chemical Industry.

研究领域: 农药化学 · 植物保护 · 天然产物化学
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INDUSTRIAL CROPS AND PRODUCTS · 2018 · IF 3.849

Bioassay-guided isolation of antifungal amides against Sclerotinia sclerotiorum from the seeds of Clausena lansium

He Yan,Zi Xiong,Na Xie,Shanzhi Liu,Lianlian Zhang,Fang Xu,Wenhui Guo,Juntao Feng

Clausena lansium ( Lour.) Skeels is an attractive shrub or small tree, a member of the Rutaceae family. The seeds, leaves and roots of this plant have been used as herbal medicines for a long time. In this study, seven amides were isolated from the seeds of Clausena lansium . The antifungal assay indicated that lansiumamide B ( 4 ) and lansiumamide C ( 2 ) displayed the highest antifungal activity against Sclerotinia sclerotiorum with EC 50 values of 4.95 and 13.24 μg/mL, which were both lower than that of carbendazim (EC 50  = 0.64 μg/mL). The structure-activity relationships of these amides were investigated using assays to measure their in vitro antifungal activities against Sclerotinia sclerotiorum . The effect of the most potent compound lansiumamide B on morphology and physiology of S. sclerotiorum were also evaluated. Lansiumamide B caused cell rupture and mycelial abnormalities of S. sclerotiorum , and its curative efficacy (75.17%) against S. sclerotiorum infection was better than that of carbendazim (56.57%). This study demonstrated that amides isolated from C. lansium possessed the potential to be exploited as botanical fungicides for commercial application or can be used as templates for designing new fungicides with novel action modes.

研究领域: 植物化学 · 真菌学 · 药理学
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