Ent-kaurane diterpenoids and other constituents from the stem of Xylopia laevigata (Annonaceae)

Total content of kaurene diterpenes in Annona vepretorum stems via 1H qNMR: A method for speeding the identification of bioactive extracts

“…In addition, the hydrogens at position 17 presented correlations with hydrogens at 2.58 and 2.05/1.97 ppm from methine and methylene groups in the positions 13 and 15, respectively (see the Supporting Information, Figure S1). Still, the integral areas of the signals 4.71 and 2.59 ppm resulted in the expected ratio 1:1. These results indicated that the resonances selected to the qNMR are not overlapped with other signals from the sample.…”

“…Careful analysis of 1 H NMR spectra of A. vepretorum extracts revealed signals at 4.71 and 4.78 ppm related to hydrogens nuclei (H‐17) of the exocyclic double bond of the KD skeleton (Figure ) . Based on those profiles, GA (6.90 ppm) was picked as the reference standard (Figure ).…”

“…Kaurene diterpenes (KDs) are very common in Annonaceae , particularly the species Annona and Xylopia . Several biological properties have been described for KDs, namely anti‐inflammatory, antinociceptive, trypanocidal, antifungal, antibacterial, larvicidal, and anti‐HIV . Up to now, mostly HPLC and GC‐based methods have been employed to determine contents of different KDs in plants .…”

A Comprehensive View on (−)‐7‐Oxo‐ent‐kaur‐16‐en‐19‐oic Acid, the Major Constituent of Xylopia sericea Leaves Extract: Complete NMR Assignments, X‐Ray Crystallographic Structure, in Vitro Antimalarial Activity and Cytotoxicity

“…Interestingly, the (4R) epimer, that is usually called kaurenoic acid or entkaur-16-en-19-oic acid, occurs along with the (4S) epimer (4-epi-kaurenoic acid) in X. amazonica [32] and X. laevigata. [33] On the other hand, only the rare (4S) epimer was isolated from Croton antisyphiliticus (Euphorbiaceae) and the configuration was based on 13 C-NMR data. [34] Furthermore, only the (4R) epimer was isolated from an in vitro culture of Smallanthus sonchifolius (Asteraceae), in the course of a biosynthetic investigation.…”

Plantas do Gênero Xylopia: Composição Química e Potencial Farmacológico

“…O estudo do extrato hexânico de cascas de x.laevigata levou ao isolamento de diterpenos do tipo ent-cauranos (23-25), já descritos neste gênero. Podemos destacar neste estudo a avaliação do potencial larvicida frente larvas de Aedes aegypt com CL 50 de 62,7 µ/mL (Silva et al,.2012). O óleo essencial de x.laevigata mostrou potencial anti-inflamatório e antinociceptivo em modelos animais (Queiroz et al, 2014 (Costa et al, 2013a).O óleo essencial de X.laevigata é rico em γ-muuroleno, d-cadineno.…”