Isolation of Monoterpene Dihydrochalcones from Piper montealegreanum Yuncker (Piperaceae)

Abstract

Four new compounds were isolated from the branches of Piper montealegreanum Yuncker, a shrub found in the Amazon rainforest, including two new dihydrochalcones named claricine (1) and maisine (2), a cinnamic acid derivative 3 and a phenylalkanoid 4, along with a porphyrin identified as the known compound phaeophytin a (5). The structures were established using spectroscopic experiments, including 1D and 2D NMR and HRESIMS experiments, performed on the two monoterpene dihydrochalcones and their monoacetyl derivatives. The structural diversity of these substances is very important for the Piper genus chemotaxonomy.

Antimicrobial screening and hemolytic activity of products obtained from Piper montealegreanum Yuncker and effect in vitro on growth of Staphylococcus aureus

“…For this study, the crude ethanolic extract (CEE), chloroform (CHCl3) and ethyl acetate (EtOAc) fractions were previously obtained of the branches from Piper montealegreanum (Alves, Rocha, Braz-Filho & Chaves, 2017). The products obtained from P. montealegreanum were solubilized in a solution containing DMSO/Tween 80/distilled water (2/0.5/7.5) and all were prepared in an initial stock solution containing 4096 µg mL -1 .…”

A Review of Bioactive Compounds and Antioxidant Activity Properties of Piper Species

“…Piperaceae plants contain more than 10 genera and more than 1500 species [ 14 ]. These piper species are scattered in various places, and about 700 species are distributed in tropical America, 300 species occur in the Asian tropics, and another 15 species are found in Africa [ 15 ].…”

Isolation of new neolignans and an unusual meroterpenoid from Piper cabagranum

“…The discovery of meroterpenoid 5 effectively represents a Diels-Alder cycloaddition reaction between ketone 3 and αphellandrene (6). Although some similar examples exist, the isolation of 5 provides the first example of a Diels-Alder product between an unsubstituted phenylpropenone and a terpene (Pasfield et al, 2013;Alves et al, 2017;Qiu et al, 2018;Tortora et al, 2022;Zhou et al, 2023). Given the instability of 3, we hypothesize that the ketone precursor could be formed in situ and simultaneously trapped by α-phellandrene in a single enzymatic step.…”