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An increasing number of ecological studies have used chemical diversity as a functionally relevant, scalable measure of phytochemical mixtures, demanding more rigorous attention to how chemical diversity is estimated. Most studies have focused on the composition of phytochemical mixtures and have largely ignored structural concerns, which may have greater importance for ecological function. Here, we explore the development of structural complexity and compositional diversity resulting from different biotic and abiotic interactions in Piper kelleyi Tepe (Piperaceae). We also describe how variation in structural complexity and compositional diversity differs between two congeners, P. kelleyi and P. reticulatum. To better interpret these results, we have developed a framework for interpreting these dimensions of chemical diversity in phytochemical mixtures.We used the tropical shrub, P. kelleyi, as a model system to examine interactions between ecological factors and dimensions of phytochemical diversity. We also compared compositional diversity and metabolic complexity in P. kelleyi and P. reticulatum using liquid chromatography and 1H NMR, respectively, to examine trade‐offs between compositional diversity and structural complexity. A framework is provided to generate meaningful estimates of the structural complexity of phytochemical mixtures as measured by 1H NMR.Piper is an abundant plant genus that supports diverse insect communities throughout the tropics. Subtle changes in understorey forest light were associated with increases in herbivory that directly increased compositional diversity and indirectly decreased structural complexity in P. kelleyi. This was attributed to the production of oxidation products resulting from herbivory‐driven decomposition of structurally complex defence compounds. This type of complex result would remain undetected using standard chemical ecology approaches and accounts for the detailed molecular changes that are likely to affect species interactions.Synthesis. Our quantitative framework provides a method for considering trade‐offs between structural complexity and compositional diversity and the interpretation of analytical approaches for each. This methodology will provide new theoretical insights and a more sophisticated model for examining the ecology and evolution of chemically mediated interactions. [ABSTRACT FROM AUTHOR]

Prenylflavonoids are an unique class of phytochemicals found in the inflorescences of the hop plant (Humulus lupulus). These flavonoids have demonstrated a wide range of biological activities, which may be influenced by their stereochemical configuration. Additionally, recent studies suggest that hop prenylflavonoids are subject to biotransformations which could alter or enrich their stereochemistry. In order to facilitate studies of the stereoisomers of flavanones, a facile method was developed for resolving the diastereomeric esters of flavanones via reversed-phase HPLC. Herein, a method for forming the tri-(1S)-(-)-camphanic acid esters of the 4',5,7-trihydroxy flavanones naringenin, 8-prenylnaringenin and 6-prenylnaringenin, is described. The respective diastereomers were separated using analytical reversed-phase HPLC. Diastereomeric esters were isolated by preparative HPLC to >98% d.e. based on HPLC, with their absolute configurations established by application of CD spectrometry.