A stilbene and two flavanones from Derris rariflora

Braz-Filho, Raimundo; Gottlieb, Otto R.; Mourão, Ayssor P.

doi:10.1016/0031-9422(75)85051-5

Cited by 36 publications

(9 citation statements)

References 2 publications

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“…The 1 H-NMR spectrum of 1b was similar to that of 1 with the exception of a singlet signal at 3.83 ppm corresponding to the methyl ether, now present in the C-7 position and matching the methyl ether carbon signal at 56.14 ppm in the 13 C-NMR spectrum. Likewise, this was corroborated by heteronuclear correlation observed in its 1 H- 13 C-HSQC spectrum; the structural elucidation was confirmed by data reported by Filho et al [ 21 ].…”

Section: Resultssupporting

confidence: 81%

Cytotoxic Evaluation of (2S)-5,7-Dihydroxy-6-prenylflavanone Derivatives Loaded PLGA Nanoparticles against MiaPaCa-2 Cells

et al. 2017

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The search for new alternatives for the prevention and treatment of cancer is extremely important to minimize human mortality. Natural products are an alternative to chemical drugs, since they are a source of many potential compounds with anticancer properties. In the present study, the (2S)-5,7-dihydroxy-6-prenylflavanone (semi-systematic name), also called (2S)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1-Benzopyran-4-one (CAS Name registered) (1) was isolated from Eysenhardtia platycarpa leaves. This flavanone 1 was considered as the lead compound to generate new cytotoxic derivatives 1a, 1b, 1c and 1d. These compounds 1, 1a, 1b, 1c, and 1d were then loaded in nanosized drug delivery systems such as polymeric nanoparticles (NPs). Small homogeneous spherical shaped NPs were obtained. Cytotoxic activity of free compounds 1, 1a, 1b, 1c, and 1d and encapsulated in polymeric NPs (NPs1, NPs1a, NPs1b, NPs1c and NPs1d) were evaluated against the pancreatic cancer cell line MiaPaCa-2. The obtained results demonstrated that NPs1a and NPs1b exhibited optimal cytotoxicity, and an even higher improvement of the cytotoxic efficacy was exhibited with the encapsulation of 1a. Based on these results, NPs1a were proposed as promising anticancer agent candidates.

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Section: Resultssupporting

confidence: 81%

Cytotoxic Evaluation of (2S)-5,7-Dihydroxy-6-prenylflavanone Derivatives Loaded PLGA Nanoparticles against MiaPaCa-2 Cells

et al. 2017

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“…Isoxanthohumol ( 2 ) was also isolated and identified alongside with 2',4',6'-trihydroxy-3'-prenylchalcone ( 3 ), and glabranin ( 5 ) from H. cymosum [15,16]. The rare compound 6 was identified previously from Derris rariflora [17]. Quercetin ( 7 ) was isolated form H. arenarium [18], while 4′-methoxyquercetin ( 8 ) was identified from Dryas octopetala [19], 4'-methoxykaempferol ( 9 ) from Dilleniacea indica [20], and mosloflavone ( 10 ) from Polemonium viscosum [21].…”

Section: Resultsmentioning

confidence: 99%

Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

et al. 2015

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Ten flavonoid-related structures viz. heliteretifolin (1), isoxanthohumol (2), 2',4',6'-trihydroxy-3'-prenylchalcone (3), isoglabranin (4), glabranin (5), 7-methoxy-isoglabranin (6), quercetin (7), 4'-methoxyquercetin (8), 4'-methoxykaempferol (9) and mosloflavone (10) were isolated from a H. teretifolium methanolic extract and identified. One of them (compound 1) is reported for the first time from a natural source, while compounds 6, 8–10 were isolated for the first time from the genus Helichrysum. The total extract of H. teretifolium showed potent antioxidant activity. When tested for total antioxidant capacity compound 3 possesses moderate biological activity compared to 2, which displayed some of the highest TEAC values (4529.01 ± 2.44; 4170.66 ± 6.72) µM TE/g, respectively. Compounds 7 and 8 demonstrated the highest inhibitory activities on Fe2+-induced lipid peroxidation (IC50 = 2.931; 6.449 µg/mL); tyrosinase (8.092; 27.573) and elastase (43.342; 86.548). Additionally, the total antioxidant capacities measured as FRAP (4816.31 ± 7.42; 3584.17 ± 0.54) µM AAE/g, and ORAC for hydroxyl radical (7.265 ± 0.71; 6.779 ± 3.40) × 106 and peroxyl radical (17.836 ± 2.90; 12.545 ± 5.07) × 103 µM TE/g were also observed for compounds 7 and 8, respectively. In conclusion, H. teretifolium total extract represents a rich source of bioactive constituents with potent antioxidant and moderate anti-tyrosinase and anti-elastase activities that can help to avert accumulation of free radicals in the body, and could therefore be good candidates for the prevention and/or treatment of skin-related conditions, such as aging. This is the first scientific report on the chemical and biological profile of H. teretifolium.

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“…The present phytochemical study of the leaves of Deguelia utilis afforded five new flavonoids, named as prenyl-urucuol A (1), prenyl-isotirumalin (2), 3'-methoxylupinifolin (3), prenylutiline (4) and prenylutilinol (5). A fraction containing all these flavonoids (FR3) showed significant cell viability when compared with cell cultures treated with rotenone, a mitochondrial complex I inhibitor, strongly suggesting a cytoprotective effect for this fraction.…”

Section: Discussionmentioning

confidence: 99%

“…This shrub can reach 3 meters of height and its roots are well known for their piscicide and pesticide properties attributed to its high contents of rotenoids such as rotenone and deguelin. [3][4][5] Rotenone, which can be extracted from Deguelia roots, is a lipophilic mitochondrial complex I inhibitor, and it has been widely used as a neurotoxicant in both in vivo and in vitro models of Parkinson´s disease. 6 Regarding studies about Deguelia spp., many phytochemical reports are found in the literature describing the chemistry of the roots.…”

Section: Introductionmentioning

confidence: 99%

Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties

Oliveira¹,

Almeida²,

Silva³

et al. 2012

J. Braz. Chem. Soc.

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A stilbene and two flavanones from Derris rariflora

Cited by 36 publications

References 2 publications

Cytotoxic Evaluation of (2S)-5,7-Dihydroxy-6-prenylflavanone Derivatives Loaded PLGA Nanoparticles against MiaPaCa-2 Cells

Cytotoxic Evaluation of (2S)-5,7-Dihydroxy-6-prenylflavanone Derivatives Loaded PLGA Nanoparticles against MiaPaCa-2 Cells

Inhibition of Oxidative Stress and Skin Aging-Related Enzymes by Prenylated Chalcones and Other Flavonoids from Helichrysum teretifolium

Flavonoids from the leaves of Deguelia utilis (Leguminosae): structural elucidation and neuroprotective properties

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