- Microbial conjugation studies of licochalcones and xanthohumol
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Microbial conjugation studies of licochalcones (1–4) and xanthohumol (5) were performed by using the fungi Mucor hiemalis and Absidia coerulea. As a result, one new glucosylated metabolite was produced by M. hiemalis whereas four new and three known sulfated metabolites were obtained by transformation with A. coerulea. Chemical structures of all the metabolites were elucidated on the basis of 1D-, 2D-NMR and mass spectroscopic data analyses. These results could contribute to a better understanding of the metabolic fates of licochalcones and xanthohumol in mammalian systems. Although licochalcone A 4′-sulfate (7) showed less cytotoxic activity against human cancer cell lines compared to its substrate licochalcone A, its activity was fairly retained with the IC50 values in the range of 27.35–43.07 μM.
- Han, Fubo,Xiao, Yina,Lee, Ik-Soo
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- Synthetic method for licochalcone C
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According to the present invention, licochalcone C is produced by performing C-prenylation using A_2O_3, position selective deprotection and methylation, and general Claisen-Schmidt condensation under a base condition. A [3,3]-sigma bond position transferring reaction promoted by water cannot be applied to licochalcone C synthesis due to a decomposition problem. According to the present invention, it has been confirmed that position selective C-prenylation using Al_2O_3 is a novel method for synthesizing licochalcone C.COPYRIGHT KIPO 2015
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- Facile synthesis of licochalcone C
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Licochalcone C was synthesized from commercially available 2,4-dihydroxybenzaldehde by using regioselective Al2O 3-mediated C-prenylation followed by conventional Claisen-Schmidt condensation in basic condition.
- Kim, Cheol Gi,Jeon, Jae-Ho,Seo, Young Hwa,Jun, Jong-Gab
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p. 1996 - 1998
(2014/09/17)
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- Concise synthesis of licochalcone C and its regioisomer, licochalcone H
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Licochalone C (7a) is a retrochalcone isolated from Glycyrrhiza inflata, which shows potent antioxidant properties and inhibition of bacterial growth and cellular respiration. Biological studies have suggested that licochalcone C attenuates the lipopolysaccharide and interferon-gamma induced inflammatory response by decreasing the expression and activity of inducible nitric oxide synthase and modulating the antioxidant network activity of superoxide dismutase, catalase, and glutathione peroxidase activity. Licochalcone C also inhibits NADH-cytochrome C reductase in the membrane fraction of Micrococcus luteus. Since pharmacological activity studies of licochalcone C are ongoing and the yield of the compound is poor from natural product, we report a concise four step synthesis of licochalcone C (7a) and its regioisomer, tentatively called licochalcone H (7b), by employing acid-mediated Claisen-Schmidt condensation as a key step with 6 and 20 % overall yield, respectively.
- Wang, Zengtao,Cao, Yongkai,Paudel, Suresh,Yoon, Goo,Cheon, Seung Hoon
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p. 1432 - 1436
(2014/01/06)
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- Biologically active 1,3-bis-aromatic-prop-2-en-1-ones, 1,3-bis-aromatic-propan-1-ones, and 1,3-bis-aromatic-prop-2-yn-1-ones
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The invention relates to the use of 1,3-bis-aromatic-prop-2-en-1-ones (chalcones), 1,3-bis-aromatic-propan-1-ones (dihydrochalcones), and 1,3-bis-aromatic-prop-2-yn-1-ones for the preparation of pharmaceutical compositions for the treatment or prophylaxis of a number of serious diseases including i) conditions relating to harmful effects of inflammatory cytokines, ii) conditions involving infection by Helicobacter species, iii) conditions involving infection by viruses, iv) neoplastic disorders, and v) conditions caused by microorganisms or parasites. The invention also relates to novel chalcones and dihydrochalcones (especially alkoxy substituted variants) having advantageous substitution patterns with respect to their effect as drug substances, and to methods of preparing them, as well as to pharmaceutical compositions comprising the novel chalcones. Moreover, the present invention relates to a method for the isolation of Leishmania fumarate reductase, QSAR methodologies for selecting potent compounds for the above-mentioned purposes.
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