Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities

Rao, G. Venkateswara; Swamy, B. Narayana; Chandregowda, Venkateshappa; Reddy, G. Chandrasekara

doi:10.1016/j.ejmech.2008.05.032

Cited by 48 publications

(25 citation statements)

References 20 publications

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“…The same effect was achieved by removing the prenyl substituent at C-3', which led to helichrysetin (6) (4.4 TE) [15,16]. Similarly, Rao et al demonstrated that the prenylated chalcone 3-prenylisoliquiritigenin (7a) was a better DPPH radical-scavenger than its non-prenylated analog isoliquiritigenin (7b) [17]. In spite of these results, hydroxychalcones without prenyl substituents are frequently an object of antioxidative studies.…”

Section: Antioxidant Activitymentioning

confidence: 84%

Trends in Utilization of the Pharmacological Potential of Chalcones

Batovska

Todorova²

2010

CCP

299

206

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Chalcones (1,3-diaryl-2-propen-1-ones) are open chain flavonoids that are widely biosynthesized in plants. They are important for the pigmentation of flowers and, hence, act as attractants to the pollinators. As flavonoids, chalcones also play an important role in defense against pathogens and insects. A longstanding scientific research has shown that chalcones also display other interesting biological properties such as antioxidant, cytotoxic, anticancer, antimicrobial, antiprotozoal, antiulcer, antihistaminic and anti-inflammatory activities. Some lead compounds with various pharmacological properties have been developed based on the chalcone skeleton. Clinical trials have shown that these compounds reached reasonable plasma concentrations and did not cause toxicity. For these reasons, chalcones became an object of continued interest in both academia and industry. Nowadays, several chalcones are used for treatment of viral disorders, cardiovascular diseases, parasitic infections, pain, gastritis, and stomach cancer, as well as like food additives and cosmetic formulation ingredients. However, much of the pharmacological potential of chalcones is still not utilized. The purpose of this review is to describe the recent efforts of scientists in pharmacological screening of natural and synthetic chalcones, studying the mechanisms of chalcone action and relevant structure-activity relationships. Put together, these activities aimed at synthesis of pharmacologically active chalcones and their analogs.

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Section: Antioxidant Activitymentioning

confidence: 84%

Trends in Utilization of the Pharmacological Potential of Chalcones

Batovska

Todorova²

2010

CCP

299

206

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“…Friedel-Crafts reaction using Lewis acids (entries 6-8) 15 did not give the prenylated product. Strong base condition using KOH (entries 9-10) 16 gave only undesired regioisomer 9. Licochalcone C is synthesized from the C-prenylated product 8 prepared using Al 2 O 3 , thus regioselective protection of 8 to 10 in 95% yield followed by methylation using K 2 CO 3 with MeI to give 11 in 81% yield, and base-mediated Claisen-Schmidt condensation with acetophenone 12 allow- C NMR data.…”

Section: Resultsmentioning

confidence: 99%

Facile Synthesis of Licochalcone C

Kim¹,

Jeon

Seo³

et al. 2014

Bulletin of the Korean Chemical Society

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“…The prenylated flavonoids possess antioxidative function in oxidative stress (Rao et al, 2009). PC is one of the single compounds purified from S. flavescens.…”

Section: Pc Induce Ho-1 Expression In Hacat Cellsmentioning

confidence: 99%

Prenylated chalcone from Sophora flavescens suppresses Th2 chemokine expression induced by cytokines via heme oxygenase-1 in human keratinocytes

Choi

Lee

et al. 2010

Arch. Pharm. Res.

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We recently reported the inhibitory effect of an oral administration of a Sophora flavescens Aiton methanol extract on the development of atopic dermatitis in the NC/Nga model mice. Heme oxygenase (HO)-1 has recently emerged as an important cytoprotective enzyme against oxidative stress and inflammatory responses in many cell types. The aim of this study was to investigate the possible mechanism by which prenylated chalcone (PC, 7,9,2',4'-tetrahydroxy-8-isopentenyl-5-methoxychalcone), a natural product isolated from S. flavescens, inhibited cytokine-induced Th2 chemokine expression in human keratinocytes, HaCaT cells. The level of chemokine expression was measured by reverse transcription-polymerase chain reaction and HO-1 study was performed by Western blot analysis. Interferon-gamma (IFN-gamma) and tumor necrosis factor-alpha (TNF-alpha)-induced thymus- and activation-regulated chemokine (TARC/CCL17), macrophage-derived chemokine (MDC/CCL22), cutaneous T-cell attracting chemokine (CTACK/CCL27) expression in a dose-dependent manner. Interestingly, PC significantly suppressed IFN-gamma and TNF-alpha-induced TARC/CCL17, MDC/CCL22 and CTACK/CCL27 expression via the induction of heme oxygenase (HO)-1. This suppression was completely restored by HO-1 siRNA, suggesting a direct role of HO-1 for the suppressive effect. Furthermore, exogenous CO, but not other end products of HO-1 activity, also suppressed IFN-gamma and TNF-alpha-induced TARC/CCL17, MDC/CCL22 and CTACK/CCL27 expression. These results demonstrate that prenylated chalcone induces HO-1 expression, which in turn HO-1 and/or CO suppresses Th2 chemokine expressions induced by cytokines in human HaCaT cells.

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Synthesis of (±)Abyssinone I and related compounds: Their anti-oxidant and cytotoxic activities

Cited by 48 publications

References 20 publications

Trends in Utilization of the Pharmacological Potential of Chalcones

Trends in Utilization of the Pharmacological Potential of Chalcones

Facile Synthesis of Licochalcone C

Prenylated chalcone from Sophora flavescens suppresses Th2 chemokine expression induced by cytokines via heme oxygenase-1 in human keratinocytes

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