A new biphenyl from Clusia melchiorii and a new tocotrienol from C. obdeltifolia

Over the last twenty years, tocotrienol analogues raised great interest because of their higher level and larger domain of biological activities when compared with tocopherols. Amongst the most promising therapeutic application, anti-inflammatory potency has been evaluated through the inhibition of various mediators of inflammation. Here, we worked on the isolation of two natural isoforms of garcinoic acid (i.e., δ and γ) from two different sources, respectively, Garcinia kola seeds and Garcinia amplexicaulis bark. We also developed semisynthetic strategies to access the other two non-natural α- and β-garcinoic acid isoforms. In the next stage of our work, microsomal prostaglandin E2 synthase was defined as a target to evaluate the anti-inflammatory potential of the four garcinoic acid isomers. Both dimethylated isoforms, β- and γ-garcinoic acid, exhibited the lowest IC50, 2.8 µM and 2.0 µM, respectively. These results showed that the affinity of tocotrienol analogues to microsomal prostaglandin E2 synthase-1 most probably contributes to the anti-inflammatory potential of this class of derivatives.

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“…ex Planch. & Triana (Clusiaceae) [12], Clusia obdeltifolia V. Bittrich (Clusiaceae) [13], and Clusia grandiflora Splitg. [14].…”

Section: Resultsunclassified

Semisynthetic and Natural Garcinoic Acid Isoforms as New mPGES-1 Inhibitors

et al. 2016

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“… 45 A mixture of 2( Z )-δ-garcinoic acid and 2( E )-δ-garcinoic acid was isolated from the stem of Clusia obdeltifolia . 46 …”

Section: Meroditerpenesmentioning

confidence: 99%

“… 45 δ-( Z )-Deoxy-amplexichromanol was earlier described by Teixeira et al in Clusia obdeltifolia . 46 In addition, dimeric oxidation and condensation products of amplexichromanols have been characterized. 43 …”

Section: Meroditerpenesmentioning

confidence: 99%

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Birringer

Siems²,

Maxones

et al. 2018

RSC Adv.

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“…The genus Clusia comprises about 250 species, which occur in tropical and subtropical regions of South and Central America [5]. Its species occur in the form of shrubs, vines and small-to medium-sized trees up to 20 m tall, with evergreen foliage [6].…”

Section: Introductionmentioning

confidence: 99%

Modulation of Inflammatory Processes by Leaves Extract from Clusia nemorosa Both In Vitro and In Vivo Animal Models

et al. 2011

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The present study was carried out to investigate the anti-inflammatory effect of the hexane extract of the leaves from Clusia nemorosa G. Mey, called HECn, using carrageenan-induced mice pleurisy and cotton pellet-induced mice granuloma. Additionally, the ability of HECn to affect both neutrophil migration as viability was investigated by use of the Boyden chamber assay and flow cytometry, respectively. The HECn significantly inhibited exudation, total leukocytes and neutrophils influx, as well as TNFα levels in carrageenan-induced pleurisy. However, the extract not suppressed the granulomatous tissue formation in the cotton pellet-induced granuloma test. Experiments performed in vitro revealed that HECn on human neutrophils inhibited a dose-dependent manner the CXCL1-induced neutrophil chemotaxis. Furthermore, HECn also inhibited the chemoattraction of human neutrophils induced by formyl-methionyl-leucyl-phenylalanine (fMLP), leukotriene B4 (LTB4) and platelet activating factor (PAF) in a Boyden chamber. However, this same treatment not was able to induce apoptosis. The results obtained in this study showed that the extract from leaves of C. nemorosa possess a potent inhibitory activity in acute model of inflammation, being the effects mediated, in part, by inhibition of neutrophil responsiveness. These results indicate that C. nemorosa could be a good source for anti-inflammatory compounds.

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A new biphenyl from Clusia melchiorii and a new tocotrienol from C. obdeltifolia

Cited by 22 publications

References 17 publications

Semisynthetic and Natural Garcinoic Acid Isoforms as New mPGES-1 Inhibitors

Semisynthetic and Natural Garcinoic Acid Isoforms as New mPGES-1 Inhibitors

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Modulation of Inflammatory Processes by Leaves Extract from Clusia nemorosa Both In Vitro and In Vivo Animal Models

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