Inhibitory components from the buds of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells

Arung, Enos Tangke; Matsubara, Eri; Kusuma, Irawan Wijaya; Sukaton, Edi; Shimizu, Kuniyoshi; Kondo, Ryuichiro

doi:10.1016/j.fitote.2010.09.008

Cited by 54 publications

(36 citation statements)

References 13 publications

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“…Additionally, the chemical structure of the sugar connected at the C-4 0 may also play an important role in the activity. Moreover, it should be noted that the opposite effect was reported that quercetin and quercetin-4 0 -O-glucoside which have the hydroxyl group at C-3 inhibited the melanin biosynthesis [77]. These results indicated that the hydroxyl group at C-3 of quercetin derivatives may be important to suppress the melaninogenesis activity, and the effect for melanin biosynthesis in B16 melanoma cells of quercetin glycosides are varied significantly by the presence or absence of hydroxyl group especially combing to C-3 or C-7 position.…”

Section: Synthesis Of Quercetin Derivatives and The Melanogenesis Stimentioning

confidence: 96%

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: Synthesis Of Quercetin Derivatives and The Melanogenesis Stimentioning

confidence: 96%

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Mitsunaga

Yamauchi

2015

J Wood Sci

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“…Eugenol Antiviral 7,45 ; antiúlcera 37,46 ; antidiabético 47 ; afrodisíaco 48 ; antioxidante 6,49 ; antitumoral 6,50,51 ; anestésico e anti-inflamatório ; inibidor de edemas 39,40 ; fagorrepelente 39,62 ; anti-inflamatório 39,40 ; antitumoral 39,41 ; antialérgico 39,63 …”

Section: Atividades Reportadasunclassified

“…Todavia, a p ese ça de β-cariofileno e outros compostos podem ser citotóxicos. 50 Durante o tratamento com eugenol nenhum efeito tóxico foi observado e a sobrevida dos camundongos, que desenvolveram carcinogênese cutânea de forma induzida após o tratamento, aumentou significativamente (75%), sugerindo um ótimo potencial quimiopreparativo. Segundo Pal e colaboradores 51 o eugenol tem efeito tanto na forma tópica quanto por administração via oral.…”

Section: Efeito Antitumoralunclassified

Chemical and Biological Aspects of the Essential Oil of Indian Cloves

Affonso¹,

Rennó²,

Slana³

et al. 2012

Revista Virtual De Química

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Abstract:The Indian clove (Syzygium aromaticum, Myrtaceae) is a well appreciated spice since the ancient times not only by its flavor and culinary qualities, but also because of its therapeutic uses. Several popular and traditional applications have been reported in literature as well as numerous scientific studies on its activities. In this work we present a synopsis and discussion on S. aromaticum to provide the readers some useful information on the historical aspects, the chemical composition and its large variety of potential applications for the treatment of a number of illnesses.Keywords: Syzygium aromaticum; essential oil of Indian cloves; eugenol. ResumoO cravo-da-índia (Syzygium aromaticum, Myrtaceae) é uma especiaria muito apreciada desde a antiguidade, não só por seu sabor e qualidades culinárias, mas também por suas utilizações terapêuticas. Várias aplicações desta especiaria na cultura popular têm sido relatadas na literatura bem como diversos estudos científicos sobre esses usos. Neste trabalho, apresentamos uma sinopse e discussão dos relatos da literatura nos últimos 20 anos (tendo o SCOPUS como principal base de dados) sobre o óleo essencial do S. aromaticum, com o objetivo de proporcionar aos leitores algumas informações úteis sobre os aspectos históricos, a composição química e a grande variedade de suas aplicações potenciais no tratamento de uma série de doenças.Palavras-chave: Syzygium aromaticum; óleo de cravo; eugenol.

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“…Cell viability was measured according to a previously reported method [19], using a micro-culture 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) technique. Cells (0.5 9 10 5 per well) were grown in 24-well plates.…”

Section: Cell Viabilitymentioning

confidence: 99%

Screening for melanogenesis-controlled agents using Sudanese medicinal plants and identification of active compounds in the methanol extract of Terminalia brownii bark

2016

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We isolated and identified compounds in medicinal plant extracts that could control melanogenesis. Sudanese medicinal plants were extracted with methanol (MeOH) and 50 % ethanol (EtOH)/water, yielding 104 extracts that were screened for melanogenic activity using B16 melanoma cells. The MeOH extract of Terminalia brownii bark dose-dependently enhanced intracellular and extracellular melanogenesis, with no cytotoxicity. Furthermore, we isolated and identified the components in T. brownii MeOH extract. Gallic acid (1), a,b-punicalagin (2), a,b-terchebulin (3), ellagic acid 4-O-a-L-rhamnopyranoside (4), ellagic acid (5), and 3,4,3 0 -tri-O-methylellagic acid (6) were isolated by chromatography and identified using nuclear magnetic resonance (NMR), matrix-assisted laser desorption/ionization (MALDI) or ultra-performance liquid chromatography-time-of-flight mass spectrometry (UPLC-TOFMS), and ultraviolet (UV) spectroscopy data. Among the isolated compounds, 2, 3, 5, and 6 enhanced melanogenesis. Furthermore, compound 1 inhibited intracellular and extracellular melanogenesis with no cytotoxicity.

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Inhibitory components from the buds of clove (Syzygium aromaticum) on melanin formation in B16 melanoma cells

Cited by 54 publications

References 13 publications

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Effect of quercetin derivatives on melanogenesis stimulation of melanoma cells

Chemical and Biological Aspects of the Essential Oil of Indian Cloves

Screening for melanogenesis-controlled agents using Sudanese medicinal plants and identification of active compounds in the methanol extract of Terminalia brownii bark

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