Biosynthesis of (−)- ent -kaurenoic acid in Smallanthus sonchifolius and its effect against microbial biofilms

Lopes, Adriana A.; Pina, Edieidia Souza; Nader, Talita Thomaz; Costa, Fernando B. Da; Pereira, Ana Maria Soares; Pupo, Mônica Tallarico

doi:10.1016/j.phytol.2016.10.011

Cited by 4 publications

(1 citation statement)

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“…[34] Furthermore, only the (4R) epimer was isolated from an in vitro culture of Smallanthus sonchifolius (Asteraceae), in the course of a biosynthetic investigation. [35] These observations are clear evidences that the configurations at C-5, C-9 and C-10 in the skeleton of the kaurene diterpenes are a consequence of their biosynthetic process from (2E,6E,10E)-geranylgeranyl pyrophosphate (GGPP) cyclization under acid catalysis leading to two enantiomeric series differing from each other in their inverted configurations at carbons C-5, C-9 and C-10. Namely, the 'normal' series are the structures whose fusion between A and B rings occurs in the same way as in steroids, while the structures of the 'enantiomeric' series (denoted as ent) are the corresponding specular images of the normal series.…”

Section: Resultsmentioning

confidence: 89%

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

Gontijo

Nascimento

Borgati

et al. 2019

Chemistry & Biodiversity

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Bioguided fractionation of Xylopia sericea antiplasmodial dichloromethane leaves extract led to the isolation of (−)‐7‐oxo‐ent‐kaur‐16‐en‐19‐oic acid (C20H28O3) that was identified by a combination of 1D and 2D NMR experiments (COSY, HMBC, HSQC, HSQC‐TOCSY, HSQC‐NOESY and NOESY) and by X‐ray crystallography. A feature to be pointed out is its (4R) configuration that was inferred from the NOE experiments (HSQC‐NOESY and NOESY) and X‐ray crystallography. In vitro evaluation of this rare diterpene acid against the chloroquine‐resistant strain Plasmodium falciparum W2 by the PfLDH method showed it disclosed a low antiplasmodial activity and was not cytotoxic to HepG2 cells (CC50 862.6±6.7 μm) by the MTT assay. The unequivocal NMR signals assignments, the X‐ray crystallographic structure, the assessment to the bioactivities and the occurrence this diterpene in X. sericea are reported here for the first time.

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Section: Resultsmentioning

confidence: 89%