Derivatives of schisandrin with increased inhibitory potential on prostaglandin E2 and leukotriene B4 formation in vitro

Blunder, Martina; Pferschy‐Wenzig, Eva‐Maria; Fabian, Walter M. F.; Hüfner, Antje; Kunert, Olaf; Saf, Robert; Schühly, Wolfgang; Bauer, Rudolf

doi:10.1016/j.bmc.2009.10.031

Cited by 13 publications

(11 citation statements)

References 41 publications

(44 reference statements)

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“…Baillon 52 were synthesized and structurally characterized by means of NMR, mass spectrometry and the axial chirality of the biphenyl system was determined by comparison of calculated with measured CD spectra. 53 Selective demethylation with 1.1 equivalent of BBr 3 (reaction a) turned out to be unsuccessful, because a complex mixture of products was formed, out of which only compounds 133 and 134 could be isolated in pure form. An excess of demethylation reagent (6.5 equiv.…”

Section: Dibenzocyclooctadiene Derivativesmentioning

confidence: 99%

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Recent advances in research on lignans and neolignans

2016

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Covering: 2009 to 2015Lignans and neolignans are a large group of natural products derived from the oxidative coupling of two C6-C3 units. Owing to their biological activities ranging from antioxidant, antitumor, anti-inflammatory to antiviral properties, they have been used for a long time both in ethnic as well as in conventional medicine. This review describes 564 of the latest examples of naturally occurring lignans and neolignans, and their glycosides in some cases, which have been isolated between 2009 and 2015. It comprises the data reported in more than 200 peer-reviewed articles and covers their source, isolation, structure elucidation and bioactivities (where available), and highlights the biosynthesis and total synthesis of some important ones.

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Section: Dibenzocyclooctadiene Derivativesmentioning

confidence: 99%

“…While the original lignan was inactive, compounds 133 and 135 showing the cycloheptadiene skeleton revealed remarkable inhibitory activity on prostaglandin E 2 and leukotriene B 4 formation in vitro with IC 50 values of 4.2 and 4.5 mM, respectively. 53…”

Section: Dibenzocyclooctadiene Derivativesmentioning

confidence: 99%

Recent advances in research on lignans and neolignans

2016

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“…It is, however, possible, to identify the main directions of their biological activity (Hancke et al 1999; World Health Organization 2007), namely: blocking of calcium channels (Ca 2+ ) (Chiu et al 2008), reducing the level of: serum glutamic pyruvic transaminase (SGPT), liver glutamic-pyruvic transaminase (LGPT), alanine aminotransferase (ALT), aspartate aminotransferase (AST), inhibition of cyclooxygenase 1 and 2 (COX 1 and 2), inhibition of the production of nitric oxide (NO) (Blunder et al 2010; Hu et al 2014), inhibition of gene expression of proinflammatory cytokines (Oh et al 2010), and inactivation of cytochrome P450 (Wan et al 2010). …”

Section: Main Biological Modes Of Action Of Dibenzocyclooctadiene Ligmentioning

confidence: 99%

Current knowledge of Schisandra chinensis (Turcz.) Baill. (Chinese magnolia vine) as a medicinal plant species: a review on the bioactive components, pharmacological properties, analytical and biotechnological studies

Szopa

Ekiert²

2016

Phytochem Rev

267

215

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Schisandra chinensis Turcz. (Baill.) is a plant species whose fruits have been well known in Far Eastern medicine for a long time. However, schisandra seems to be a plant still underestimated in contemporary therapy still in the countries of East Asia. The article presents latest available information on the chemical composition of this plant species. Special attention is given to dibenzo cyclooctadiene lignans. In addition, recent studies of the biological activity of dibenzocyclooctadiene lignans and schisandra fruit extracts are recapitulated. The paper gives a short resume of their beneficial effects in biological systems in vitro, in animals, and in humans, thus underlining their medicinal potential. The cosmetic properties are depicted, too. The analytical methods used for assaying schisandra lignans in the scientific studies and also in industry are also presented. Moreover, special attention is given to the information on the latest biotechnological studies of this plant species. The intention of this review is to contribute to a better understanding of the huge potential of the pharmacological relevance of S. chinensis.

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“…A negative sign of this torsional angle (s = À60°in M1), relating in this case to an axial R-configuration, results in a maximum at 240-260 nm in the CD curve, whereas a positive sign of s, equal to an axial S-configuration, leads to a minimum in this range (Ikeya et al, 1979). Furthermore, previous experiments with schizandrins (Blunder et al, 2010) together with the present results show that the general appearance of the simulated CD curves is only marginally influenced by methoxy groups compared to the effect of the biphenyl-atropisomerism. Simulations based on the published X-ray structures of pyramidatin A (EDEXOA, Song et al, 2000) and pyramidatin B (EDEX-UG01, Song et al, 2000;Fronczek, 2006) yield CD spectra with a negative and positive, respectively, sign of the first band ( Fig.…”

Section: Resultsmentioning

confidence: 80%