Dictamnine suppresses the development of pear ring rot induced by Botryosphaeria dothidea infection by disrupting the chitin biosynthesis.

Ring rot induced by Botryosphaeria dothidea is a major cause of growth and postharvest losses in various fruits. There is an urgent need to develop green fungicides due to pesticide resistance and environmental pressure. Here, we demonstrated the efficacy of dictamnine (DIC, 4-methoxyfuro [2,3-ß] quinoline, purity 98%), a compound isolated from the stems and leaves of Clausena lansium, in effectively suppressing pear ring rot by inhibiting the mycelial growth of B. dothidea. The median effective concentration of DIC was 15.48 µg/mL. Application of DIC to B. dothidea resulted in structural disruption of the cell wall and plasma membrane, leading to mycelial deformation, breakage, and cell death. Transcriptome analysis revealed significant inhibition of the synthetic pathways for fungal cell wall and membrane components by DIC. Particularly, the expression of chitin synthase, a key enzyme of chitin synthesis, was prominently down-regulated. Moreover, the chitin content in DIC-treated B. dothidea mycelia exhibited a substantial dose-dependent reduction. Based on these results, it is promising to develop DIC as an antifungal pesticide for controlling ring rot disease in pear fruits. Our study provides new insights into the underlying mechanism through which DIC inhibits the mycelial growth of B. dothidea.

Antifungal alkaloids from the branch-leaves of Clausena lansium Lour. Skeels (Rutaceae).

BACKGROUND: The rational utilization of botanical secondary metabolites is one of the strategies to reduce the application of chemical fungicides. The extensive biological activities of Clausena lansium indicate that it has the potential to develop botanical fungicides. RESULTS: A systematic investigation on the antifungal alkaloids from C. lansium branch-leaves following bioassay-guided isolation was implemented. Sixteen alkaloids, including two new and nine known carbazole alkaloids, one known quinoline alkaloid and four known amides, were isolated. Compounds 4, 7, 12 and 14 showed strong antifungal activity on Phytophthora capsiciwith EC50 values ranging from 50.67 to 70.82 µg mL-1 . Compounds 1, 3, 8, 10, 11, 12 and 16 displayed different degrees of antifungal activity against Botryosphaeria dothidea with EC50 values ranging from 54.18 to 129.83 µg mL-1 . It was reported for the first time that these alkaloids had antifungal effects on P. capsici or B. dothidea, and their structure-activity relationships were further discussed systematically. Additionally, among all alkaloids, dictamine (12) had the strongest antifungal activities against P. capsici (EC50  = 50.67 µg mL-1 ) and B. dothidea (EC50  = 54.18 µg mL-1 ), and its physiological effects on P. capsici and B. dothidea also were further evaluated. CONCLUSION: Capsicum lansium is a potential source of antifungal alkaloids, and C. lansium alkaloids had the potential as lead compounds of botanical fungicides in the development of new fungicides with novel action mechanism. © 2023 Society of Chemical Industry.

Antifungal active ingredient from the twigs and leaves of Clausena lansium Lour. Skeels (Rutaceae).

Two novel amides, named clauphenamides A and B, and twelve other known compounds were isolated from the twigs and leaves of Clausena lansium Lour. Skeels (Rutaceae). Their structures were elucidated on the basis of extensive spectroscopic analysis and comparison with data reported in the literature. Clauphenamide A (1) featured in the unit of N-2-(4,8-dimethoxyfuro [2,3-b]quinolin-7-yl)vinyl, and clauphenamide B (2) was a unprecedented N-phenethyl cinnamide dimer. Other known compounds belong to pyrrolidone amides (3 and 4), furacoumarins (7-10), simple coumarins (11-14), lignan (5) and sesquiterpene (6). Compounds 5, 6, 10 and 12 were separated from the genus (Clausena) for the first time, while 13 was isolated in the species (C. lansium) for the first time. The antifungal activities of the isolated compounds were assayed. As a result, at the concentration of 100 µg/ml, compared with the control (chlorothalonil, inhibition rate of 83.67%), compounds 1 and 2 were found to exhibit moderate antifungal activity against B. dothidea with inhibition rates of 68.39% and 52.05%, respectively. Compounds 11-14 also exhibited moderate activity against B. dothidea and F. oxysporum, with inhibition rates greater than 40%. In addition, compared with the control (chlorothalonil, inhibition rate of 69.02%), compounds 11-14 showed strong antifungal activity to P. oryzae, with inhibition rates greater than 55%. Among them, compound 14 has the strongest antifungal activity against P. oryzae, and the inhibition rate (65.44%) is close to that of the control chlorothalonil. Additionally, the structure-activity relationships of the separated compounds are also discussed preliminarily in this paper.