- Biological Properties and Absolute Configuration of Flavanones From Calceolaria thyrsiflora Graham
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Flavanones (–)-(2S)-5,4’-dihydroxy-7-methoxyflavanone (1) and (–)-(2S)-5,3’,4’-trihydroxy-7-methoxyflavanone (2) were isolated from the extracts of Calceolaria thyrsiflora Graham, an endemic perennial small shrub growing in the central zone of Chile. The absolute configuration of these compounds was resolved by optical rotation experiments and in silico calculations. Three analogs (3, 4, and 5) were synthesized to do structure-activity relationships with the biological assays studied. Biological tests revealed that only flavanone 2 exhibited a moderate inhibitory activity against the methicillin-resistant strain S. aureus MRSA 97-77 (MIC value of 50 μg/ml). In addition, flavanone 2 showed a potent, selective, and competitive inhibition of 5-hLOX, which supports the traditional use of this plant as an anti-inflammatory in diseases of the respiratory tract. Also, 2 exhibited cytotoxic and selective effects against B16-F10 (8.07 ± 1.61 μM) but 4.6- and 17-fold lesser activity than etoposide and taxol.
- Cabezas, Francisco,Cortez-San Martín, Marcelo,Díaz, Katy,González, César,Joseph-Nathan, Pedro,Mascayano, Carolina,Mejias, Sophia,Montoya, Margarita,Mu?oz, Marcelo A.,Osorio, Mauricio,Taborga, Lautaro,Torrent, Claudia,Vásquez-Martínez, Yesseny,Valdés, Ernesto
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- A kind of A ring with methyl of [...] compound, preparation method and anti-inflammatory activity
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The invention discloses a quinoid chalcone compound with a methyl group at an A ring, and a preparation method and anti-inflammatory activity thereof. The compound has a structure as shown in a general formula (I) which is described in the specification. The preparation method comprises the following steps: (1) synthesizing 2-hydroxy-4,6-dimethoxyacetophenone; (2) synthesizing 2'-hydroxy-4',6'-dimethoxychalcone derivative; (3) synthesizing 2',4',6'-trihydroxy chalcone derivative; and (4) synthesizing the quinoid chalcone compound with a methyl group at the A ring. The compound is simple to prepare and has obvious anti-inflammatory action.
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Paragraph 0113; 0119; 0120; 0121; 0122
(2019/04/18)
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- Synthesis and antidiabetic activity of 5,7-dihydroxyflavonoids and analogs
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In a study to evaluate the structural elements essential for the antidiabetic activity of flavonoids, we synthesized two series of flavonoids, 5,7-dihydroxyflavanones and 5,7-dihydroxyflavones. In a screening for potential antidiabetic activity, most of the flavonoids showed a remarkable in vitro activity, and compounds 1f, 2d, and 3c were significantly more effective than the positive control, metformin. The biological activity was mainly affected by structural modification at the ring B moiety of the flavonoid skeleton. The results suggest that 5,7-dihydroxyflavonoids can be considered as promising candidates in the development of new antidiabetic lead compounds. Copyright
- Chang, Liu-Shuan,Li, Chun-Bao,Qin, Nan,Jin, Mei-Na,Duan, Hong-Quan
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scheme or table
p. 162 - 169
(2012/04/04)
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