Prenylated flavonoids from Artocarpus altilis: Antioxidant activities and inhibitory effects on melanin production

Lan, Wen-Chun; Tzeng, Cheng-Wei; Lin, Chun‐Ching; Yen, Feng‐Lin; Ko, Horng‐Huey

doi:10.1016/j.phytochem.2013.01.011

Cited by 75 publications

(60 citation statements)

References 45 publications

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“…While the 2, 4-substituted resorcinol shows no chelate with the copper ions and inhibits tyrosinase activity more potently than catechol by competitive binding with the copper ions in tyrosinase. The tyrosinase activity and melanogenesis of prenylated flavonoids from Artocarpus altilis were determined [44]. A. altilis is popularly known as the breadfruit tree in English.…”

Section: Melanogenesis Controlling Effect Of Medicinal Plants Extractmentioning

confidence: 99%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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Controlling melanogenesis is important for maintaining the good health and cosmetic appearance of a human body. This study aims to search the active compounds from natural products exhibiting the melanogenesis modulating activity and elucidate the mechanism underlying the observed activity. Two novel quercetin glycosideswere isolated and identified from Helminthostachys zeylanica roots 50 % ethanol extract. Compound 1 exhibited intracellular melanogenesis stimulatory activity, while 2 showed no effect even the structural similarity. To understand the structure-activity relationships, twelve quercetin glycosides and seven methylquercetins were synthesized from rutin as starting material. As the result of bioassay using synthesized nineteen quercetin derivatives in B16 melanoma cells, some quercetin-3-O-b-D-glucopyranosides stimulated the intracellular melanogenesis. On the other hand, synthesized 3-O-methylquercetin 12 and 3,4 0 ,7-Otrimethylquercetin 15 increased both intra and extracellular melanin contents with no cytotoxicity. Compoud 15 increased the phosphorylated p38 mitogen-activated protein kinase (MAPK) and microphthalmia-associated transcription factor (MITF) which regulates the expression of tyrosinase, TRP-1 and TRP-2. While 12 enhanced the expression of the melanogenic enzymes without involving the MITF, as evidenced by its lack of any stimulation of the expression of MITF and p-p38 MAPK. This result indicates that 12 may stimulate the expression of tyrosinase, TRP-1, and TRP-2 by stimulating currently unidentified transcriptional factors and/or by regulating the degradation of melanogenic enzymes.

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Section: Melanogenesis Controlling Effect Of Medicinal Plants Extractmentioning

confidence: 99%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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“…M.p. [34]. In brief,i soflavones or arbutin (positive control)w ere dissolved in DMSO/MeOH before dilution to various concentrations by potassium phosphate buffer (pH6.8).…”

Section: Experimental Partmentioning

confidence: 99%

“…B16F10 melanocyte (BCRC 60031,T aiwan)o rH aCaT keratinocyte cells were cultured in Dulbeccos modified Eagles medium (DMEM; HyClone, USA)w ith 10% fetal bovine serum (Sigma), 2mml -glutamine,2 00 Um l À 1 penicillin G, 200 mgm l À 1 streptomycin, and 0.5 mgm l À 1 amphotericinB(Kibbutz Beit Haemek,I srael) under ah umidified atmosphere containing 5% CO 2 at 378.C ells were placed in 96-well plates (1 ·10 4 cells/well). After 24 hofincubation, test samples were added and the cultures were further incubated for 48 h. Te sted concentrations of isoflavones were 10, 20, 40, and 80 mm for B16F10 murine melanoma cells, and 5, 10, 20, and 40 mm for HaCaT human keratinocyte.C ell viability was determined using the XTT assay.F ormazan formed from XTT in cell cultures during incubation was measured at 490 nm using a multi-well scanning spectrophotometer [34][35][36].…”

Section: Experimental Partmentioning

confidence: 99%

“…Themeasurement of cellular melanin formation and tyrosinase activity was conducted according to the methods described by Chen et al [37] and Lan et al [34].I nb rief,B 16F10 cells (5·10 4 cells/well)t ogether with 50 nm a-MSH were placed in 24-well plates and then incubated for 24 h. After addition of isoflavones,samples were further incubated for 48 h, followed by washing twice with PBS.Melanocytes were dissolved in 100 mlof2nNaOH and digested at 808 for 1hto solubilize the generated melanin. Absorbance was measured at 405 nm, which was used to determine the melanin content [34] [37].…”

Section: Experimental Partmentioning

confidence: 99%

“…Thes upernatants were mixed with 100 mlo fl-dopa (1 mg ml À 1 )a t 378 for 3h.T he absorbance was measured at 490 nm with am ulti-well spectrophotometer.A ll experiments were performedf or at least three times (n ! 3),a nd the inhibitionp ercentage of each compound was compared with that of control [34] [37].…”

Section: Experimental Partmentioning

confidence: 99%

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Free‐Radical‐Scavenging, Antityrosinase, and Cellular Melanogenesis Inhibitory Activities of Synthetic Isoflavones

et al. 2015

Chemistry & Biodiversity

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In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS(.+) and DPPH(.) radicals with SC50 values of 11.3 ± 0.3 and 9.4 ± 0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9 ± 4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.

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Identification of cytochrome P450 isoforms involved in the metabolism of artocarpin and assessment of its drug–drug interaction

Liu

2018

Biomedical Chromatography

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Artocarpin isolated from an agricultural plant Artocarpus communis has shows anti-inflammation and anticancer activities. In this study, we utilized recombinant human UDP-glucuronosyltransferasesupersomes (UGTs) and human liver microsomes to explore its inhibitory effect on UGTs and cytochrome p450 enzymes (CYPs). Chemical inhibition studies and screening assays with recombinant human CYPs were used to identify if CYP isoform is involved in artocarpin metabolism. Artocarpin showed strong inhibition against UGT1A3, UGT1A6, UGT1A7, UGT1A8, UGT1A9, UGT1A10, UGT2B7, CYP2C8 and CYP3A4. In particular, artocarpin exhibited competitive inhibition against CYP3A4 and noncompetitive inhibition against UGT1A3 and UGT1A7. The half inhibition concentration values for CYP3A4, UGT1A3 and UGT1A7 were 4.67, 3.82 and 4.82 μm, and the inhibition kinetic parameters for them were 0.78, 2.67 and 3.14 μm, respectively. After artocarpin was incubated in human liver microsomes and determined by HPLC, we observed its main metabolites (M1 and M2). In addition, we proved that CYP2D6 played the key role in the biotransformation of artocarpin in human liver microsomes. The result of molecular docking further confirmed that artocarpin interacted with CYP2D6, CYP2C8 and CYP3A4 through hydrogen bonds. This study provided preliminary results for further research on artocarpin or artocarpin-containing herbs.

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Prenylated flavonoids from Artocarpus altilis: Antioxidant activities and inhibitory effects on melanin production

Cited by 75 publications

References 45 publications

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Free‐Radical‐Scavenging, Antityrosinase, and Cellular Melanogenesis Inhibitory Activities of Synthetic Isoflavones

Identification of cytochrome P450 isoforms involved in the metabolism of artocarpin and assessment of its drug–drug interaction

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