Mexico is considered one of the main regions of diversification of the genus Quercus (oaks). Oak species are one of the most important tree groups, particularly in temperate forests, due to its diversity and abundance. Some studies have shown that oak contains specialized metabolites with medicinal importance. In this work, the acetonic extract from leaves of three Mexican oaks (Quercus rugosa, Q. glabrescens, and Q. obtusata) was separated using thin-layer chromatography and column chromatography. Chemical identification of the major compounds was determined using high-performance liquid chromatography and nuclear magnetic resonance. Nineteen compounds were identified, three belonging to the terpenoid family (ursolic acid, β−amyrin, and β−sitosterol) and 16 from the phenolic family. Of the isolated compounds, seven are new reports for oak species (scopoletin, ursolic acid, β-amyrin, luteolin−7−O−glucoside, kaempferol−3−O−sophoroside, kaempferol−3−O−glucoside, and kaempferol−3−O−sambubioside). More compounds were identified in Q. rugosa followed by Q. glabrescens and then Q. obtusata. The characterization of specialized metabolites in oak species is relevant, from both phytocentric and anthropocentric perspectives.

Analyzing the nutritional and defensive chemistry of Quercus rugosa provides insight into gall wasp interactions. Quercus rugosa is the most widely distributed white oak species in Mexico. It is the dominant canopy species in its geographic distribution range and has the largest number of associated gall wasp species (Cynipidae: Cynipini). Our main aims were to characterize the nutritional and defensive chemistry of Q. rugosa leaves and determine whether this chemistry differed between leaves with and without galls. We evaluated 60 trees from six populations of Q. rugosa in central Mexico. For each tree, we analyzed the nutritional chemistry (nitrogen, phosphorus, carbon, and carbon/nitrogen ratio) and defensive chemistry (secondary metabolites). Also, we characterized the community of cynipids in the leaf tissue of each tree. We documented 18 cynipid species, and the cynipid communities differed in composition among localities. We recorded the presence of a total of ten phenolics. The composition of nutritional and defensive chemicals differed significantly between leaves with and without galls in each locality. The nutritional and defensive chemical compounds of Q. rugosa were influenced by their associated cynipids. Our results suggest that gall-inducing cynipids influence the production of secondary metabolites in leaves with galls through the reassignment of nutritional compounds by the hosts.

The hybridization phenomenon increases genetic diversity and modifies recombinant individuals’ secondary metabolite (SMs) content, affecting the canopy-dependent community. Hybridization events occur when Quercus rugosa and Q. glabrescens oaks converge in sympatry. Here, we analyzed the effect of the genetic diversity (He) and SMs of Q. rugosa, Q. glabrescens and hybrids on the community of gall-inducing wasps (Cynipidae) and their parasitoids on 100 oak canopy trees in two allopatric and two hybrid zones. Eighteen gall wasp species belonging to six genera and six parasitoid genera contained in four families were identified. The most representative parasitoid genera belonged to the Chalcidoidea family. Abundance, infestation levels and richness of gall wasps and their parasitoids registered the next pattern: Q. rugosa higher than the hybrids, and the hybrids equal to Q. glabrescens. Oak host genetic diversity was the variable with the highest influence on the quantitative SMs expression, richness and abundance of gall wasps and their parasitoids. The influence of SMs on gall wasps and their parasitoids showed the next pattern: scopoletin > quercitrin > rutin = caffeic acid = quercetin glucoside. Our findings indicate that genetic diversity may be a key factor influencing the dynamics of tri-trophic interactions that involve oaks.