Abstract
In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.
Highlights
Cocoa is one of the primary products of significant importance in world trade, widely used in food, pharmaceutical and cosmetic industries [1,2]
Phytochemical study of the aerial part of P. pesaresanum led to the isolation of four compounds, which were identified by spectroscopic methods and by comparison with the data described in the literature
This study contributes to the chemistry of P. pesaresanum through the isolation and identification of three benzoic acid derivatives (1–3), a dihydrochalcone (4) and a mixture of sterols (5–7), of which 2 to 4 are reported for the first time in the species
Summary
Cocoa is one of the primary products of significant importance in world trade, widely used in food, pharmaceutical and cosmetic industries [1,2]. The production and trade of cocoa beans and their derived products constitute the base of the national economy of several underdeveloped countries [5]. Around 6.7 million hectares are estimated, with a cocoa bean production of 4.7 million tons and generating income of approximately 8.6 billion dollars per year. Production yields are moderate to low in many of the countries where it is cultivated. The reduction in productivity is caused by several factors, among which stand out the lack of technification of the crops, the drastic climatic changes, attack of pests and diseases [6,7]
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