Abstract
The chemical composition of seedlings and adult plants of several Piper species were analyzed by 1H NMR spectroscopy combined with principal component analysis (PCA) and HPLC-DAD, HPLC-HRESIMS and GC-MS data. The chromatographic profile of crude extracts from leaves of Piper species showed remarkable differences between seedlings and adult plants. Adult leaves of P. regnellii accumulate dihydrobenzofuran neolignans, P. solmsianum contain tetrahydrofuran lignans, and prenylated benzoic acids are found in adult leaves of P. hemmendorffii and P. caldense. Seedlings produced an entirely different collection of compounds. Piper gaudichaudianum and P. solmsianum seedlings contain the phenylpropanoid dillapiole. Piper regnellii and P. hemmendorffii produce another phenylpropanoid, apiol, while isoasarone is found in P. caldense. Piper richadiaefolium and P. permucronatum contain dibenzylbutyrolactones lignans or flavonoids in adult leaves. Seedlings of P. richardiaefolium produce multiple amides, while P. permucronatum seedlings contain a new long chain ester. Piper tuberculatum, P. reticulatum and P. amalago produce amides, and their chemistry changes less during ontogeny. The chemical variation we documented opens questions about changes in herbivore pressure across ontogeny.
Highlights
The genus Piper belongs to the family Piperaceae and it is considered a megadiverse group among Angiospermae [1]
While some species are rich in amides such as P. tuberculatum [8], P. scutifolium and P. hoffmanseggianum [9], other characteristic compounds found in Piper are lignans from P. solmsianum [10], neolignans from P. regnellii [11] and P. decurrens [12], and acid benzoic derivatives in P. aduncum, P. crassinervium [13,14,15,16], P. hispidum [17] and P. gaudichaudianum [15,18]
Previous work on ontogenetic variation of the chemistry of P. gaudichaudianum shows that the main chemical constituents of seedlings are the phenylpropanoids apiol (1) and dillapiole (2)
Summary
The genus Piper belongs to the family Piperaceae and it is considered a megadiverse group among Angiospermae [1]. Piper is chemically very diversified and the most common class of secondary compounds found are amides. Data on chemical variation in plants come from studies on responses to abiotic and biotic factors including light, nutrients, herbivory, and pathogens, but some important work has documented changes in secondary metabolites during ontogeny. Ontogenetic changes in defenses are common [27,28], as herbivore host searching is limited and survival is higher among seedlings which are chemically distinct from their mother plants [29,30]. Plant chemotypes are more variable than phylogeny would suggest [35,36], further indicating that variation in plant chemistry enables survival by limiting herbivory Together, these patterns suggest that studying plant secondary metabolites early in ontogeny may lead to a better understanding of phytochemical diversity. We document ontogenetic changes in secondary metabolites in nine Piper species, showing that changes in phytochemistry are quite common during development
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