(R)-(-)-carvone and (1R, 4R)-trans-(+)-dihydrocarvone from poiretia latifolia vogel

Abstract

Os óleos essenciais de folhas de Poiretia latifolia Vogel nativas e cultivadas (amostras A e B, respectivamente) e de flores nativas (amostra C), foram obtidos por hidrodestilação e analisados por CG, CG/EM, e através de cromatografia gasosa em fase quiral (CGFQ (61,05, 64,20, 4,50%, respectivamente). Os óleos essenciais apresentaram uma atividade antimicrobiana moderada quando avaliados frente a bactérias e Gram-positivas, Gramnegativas e fungos.The essential oils of Poiretia latifolia Vogel, native and cultivated leaves (Samples A and B, respectively) and native flowers (sample C), were obtained by hydrodistillation and analyzed by GC, GC/MS and chiral phase gas chromatography (CPGC). Twenty-four compounds were identified, representing 99.25, 99.26 and 99.23% of the oils, respectively. The major constituents of the oils were the monoterpenes (S)-(-)-limonene (16.05, 27.60, 15.60%, respectively), (1R, 4R)-trans-(+)-dihydrocarvone (18.05, 0.66 and 77.80%, respectively) and (R)-(-)-carvone (61.05, 64.20 and 4.50%, respectively). The essential oils were evaluated against some strains of Gram (+) and Gram (-) bacteria, and yeast, but displayed only modest antimicrobial activity.

Comparative characterization of novel ene‐reductases from cyanobacteria

“…An Astec Chiraldex B‐TA column (40 m. 0.25 mm, Sigma–Aldrich, Schnelldorf, Germany) was applied for the analysis of (R)‐carvone, 2‐methylmaleimide, 2‐methyl‐2‐cyclopenten‐1‐one, 3‐methyl‐2‐cyclohexen‐1‐one and the respective reduction products as described previously (Fryszkowska et al, 2009; Hall et al, 2008a; Mueller et al, 2010). (S)‐carvone, (2R,2S)‐ and (2S,2S)‐dihydrocarvone were analyzed on a Lipodex E column (25 m, 0.25 mm, Macherey Nagel, Düren, Germany) according to Porto et al (2010). Ketoisophorone and (R)‐levodione were determined on a CP‐Chirasil‐DEX CB column (25 m, 0.32 mm, Agilent Technologies, Böblingen, Germany) according to Hall et al (2008a).…”

Screening a Strain of Klebsiella sp. O852 and the Optimization of Fermentation Conditions for Trans-Dihydrocarvone Production

“…Dihydrocarvone can be used not only as a flavoring additive in the food industry, but also as a chiral building block for the synthesis of different molecules of biological interest, such as keto decalin derivatives, tetraoxane derivatives, terpenes thujopsene and (+)-decipienin A [ 29 , 30 ]. Besides, dihydrocarvone had an inhibitory effect on bacterial and fungal growth, and presented good performance as an insect repellent [ 31 ].…”

“…biological interest, such as keto decalin derivatives, tetraoxane derivatives, terpenes thujopsene and (+)-decipienin A [29,30]. Besides, dihydrocarvone had an inhibitory effect on bacterial and fungal growth, and presented good performance as an insect repellent [31]. Taken together, Klebsiella sp.…”

In Vitro Antifungal Activity and Toxicity of Dihydrocarvone-Hybrid Derivatives against Monilinia fructicola

“…Among this group of molecules, terpenic ketones, such as dihydrocarvone, are important subclass of natural compounds, which can serve as versatile synthetic building blocks and key intermediates in drug design [15]. Dihydrocarvone is the main component in the essential oil from Poiretia latifolia flowers (50-70% present) [16] and is present in low proportions in other oils with antifungal capacity, such as Mentha longifolia, M. spicata, M. pulegium, and Anethum sowa [17][18][19]. This monoterpene ketone is a potential growth inhibitor of yeast fungi such as Saccharomyces cerevisiae, Candida albicans, and Cryptococcus neoformans [16].…”