Melanin Biosynthesis Inhibitors from the Bark of Machilus thunbergii

Li, Gao; Ju, Hye Kyung; Chang, Han Soo; Jahng, Yurngdong; Lee, Seungho; Son, Jong‐Keun

doi:10.1248/bpb.26.1039

Cited by 40 publications

(20 citation statements)

References 29 publications

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“…However, abnormal accumulation of melanin causes esthetic problems and hyperpigmentation disorders, such as freckles, chloasma, lentigo, liver spots, and melasma (Ahn et al, 2006;Iozumi et al, 1993;Li et al, 2003;Unver et al, 2006). Arbutin, kojic acid, hydroquinone, and ascorbic acid have been used to treat hyperpigmentation disorders.…”

Section: Discussionmentioning

confidence: 99%

“…The production of melanin is an important defense system of the skin, but excessive accumulation of melanin induces hyper pigmentation disorders such as freckles, lentigo, and melasma (Ahn et al, 2006;Iozumi et al, 1993;Li et al, 2003). There is great interest in discovering depigmentation agents to prevent or treat hyperpigmentation disorders for medical or cosmetic reasons.…”

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confidence: 99%

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Lipoteichoic Acid Isolated from Lactobacillus plantarum Inhibits Melanogenesis in B16F10 Mouse Melanoma Cells

Kim¹,

Kim²,

Jung³

et al. 2015

Molecules and Cells

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Lipoteichoic acid (LTA) is a major component of the cell wall of Gram-positive bacteria. Its effects on living organisms are different from those of lipopolysaccharide (LPS) found in Gram-negative bacteria. LTA contributes to immune regulatory effects including anti-aging. In this study, we showed that LTA isolated from Lactobacillus plantarum (pLTA) inhibited melanogenesis in B16F10 mouse melanoma cells. pLTA reduced the cellular activity of tyrosinase and the expression of tyrosinase family members in a dose-dependent manner. The expression of microphthalmia-associated transcription factor (MITF), a key factor in the synthesis of melanin, was also decreased by pLTA. Further, we showed that pLTA activated melanogenesis signaling, such as extracellular signal-regulated kinase (ERK) and phosphatidylinositol 3-kinse (PI3K)/AKT. In addition, the expression of heterogeneous nuclear ribonucleoprotein A1 (hnRNP A1) and HuR, which are important RNA-binding proteins (RBPs), was reduced. pLTA likely degrades MITF via regulation of melanogenic signaling and RNA stability of melanogenic proteins, resulting in the reduction of melanin. Thus, our data suggest that pLTA has therapeutic potential for treating hyperpigmentation disorders and can also be used as a cosmetic whitening agent.

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Section: Discussionmentioning

confidence: 99%

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confidence: 99%

Lipoteichoic Acid Isolated from Lactobacillus plantarum Inhibits Melanogenesis in B16F10 Mouse Melanoma Cells

Kim¹,

Kim²,

Jung³

et al. 2015

Molecules and Cells

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“…Some flower and leaf extracts have antioxidant and antimelanogenetic effects and have been used as cosmetic raw materials; however, they are mainly non-volatile compounds and have been studied without regard to their aromatic properties. [12][13][14][15][16] The aromatic components in Osmanthus flower are known to contain various β-ionone and its derivatives, which have outstanding scents. [17][18][19][20][21][22][23] Dihydro-β-ionol 1 [17][18][19][20][21] and β-ionol 2 22,23) are representative of these compounds.…”

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confidence: 99%

Discovery of Aromatic Components with Excellent Fragrance Properties and Biological Activities: β-Ionols with Antimelanogenetic Effects and Their Asymmetric Syntheses

Komaki

Ikawa

Saito

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Both enantiomers of dihydro-β-ionol and β-ionol, contained in the aromatic components of Osmanthus flower and of Hakuto peach, were obtained with high optical purity by lipase-catalyzed kinetic resolution of the racemates. It was found that all these enantiomers had different characteristic favorable scents and high antimelanogenetic effects. The absolute configuration and the enantiomer ratios of dihydro-β-ionol in the aromatic components of Osmanthus flower and of Hakuto peach were determined. The asymmetric synthesis of (R)-dihydro-β-ionol, one of the most valuable raw materials for fragrance and flavor, was performed from inexpensive β-ionone via lipase-catalyzed dynamic kinetic resolution followed by reduction.Key words dihydro-β-ionol; antimelanogenetic effect; aromatic component; Osmanthus flower; asymmetric synthesis; lipase-catalyzed kinetic resolution It has long been known that spices such as cloves have antibacterial and antioxidant effects, and they have been used as food preservatives.1-5) It has been reported that one of the main components of cloves, eugenol, is also present in the essential oils of flowers such as jasmine and rose, and serves as a major aromatic component. [6][7][8][9][10][11] However, research on fragrances has focused only on their aroma, and no attention has been paid to their biological activities. Some flower and leaf extracts have antioxidant and antimelanogenetic effects and have been used as cosmetic raw materials; however, they are mainly non-volatile compounds and have been studied without regard to their aromatic properties. 12-16)The aromatic components in Osmanthus flower are known to contain various β-ionone and its derivatives, which have outstanding scents.17-23) Dihydro-β-ionol 1 17-21) and β-ionol 2 22,23) are representative of these compounds. However, their absolute configurations remained unknown until quite recently, 24) and synthetic racemates [(±)-1 and (±)-2] have been used as raw materials of fragrances.Based on the above facts, we thought that some of the volatile aromatic components obtained from flowers should have excellent properties in terms of scent and biological activities. In addition, it is highly probable that the two enantiomers of an optically active compound will have different aromatic characters and different biological activities. However, the aromatic components obtained from natural sources are present in minute amounts, therefore little has been discovered about the aromatic properties and biological activities of both enantiomers of naturally occurring aromatic components. We have therefore been undertaking a project on the discovery of such compounds from natural essential oils and on the asymmetric synthesis of sufficient quantities of the natural components and their enantiomers to identify their structures and absolute configurations, and to evaluate their biological activities. This paper reports some results of a study of the aromatic components in Osmanthus flower and in Hakuto peach. 25) In this study, we succeeded in obtai...

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“…These compounds inhibit the formation of melanin pigment by inhibiting the activity of tyrosinase, which is a key enzyme in melanin biosynthesis. Other tyrosinase inhibitors have been isolated from Morus alba L. (Moraceae), 9) Machilus thunbergii (Lauraceae), 10) Trichosanthes kirilowii (Cucurbitaceae), 11) Piper longum (Piperaceae) 12) and Artocarpus heterophyllus (Moraceae). 13) On the other hand, linoleic acid, which is formed as a secondary metabolite in various plants, inhibits the formation of melanin pigment without inhibiting tyrosinase activity.…”

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confidence: 99%

A Novel Melanin Inhibitor: Hydroperoxy Traxastane-Type Triterpene from Flowers of Arnica montana

Maeda¹,

Naitou²,

Umishio³

et al. 2007

Biological & Pharmaceutical Bulletin

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Melanin Biosynthesis Inhibitors from the Bark of Machilus thunbergii

Cited by 40 publications

References 29 publications

Lipoteichoic Acid Isolated from Lactobacillus plantarum Inhibits Melanogenesis in B16F10 Mouse Melanoma Cells

Lipoteichoic Acid Isolated from Lactobacillus plantarum Inhibits Melanogenesis in B16F10 Mouse Melanoma Cells

Discovery of Aromatic Components with Excellent Fragrance Properties and Biological Activities: β-Ionols with Antimelanogenetic Effects and Their Asymmetric Syntheses

A Novel Melanin Inhibitor: Hydroperoxy Traxastane-Type Triterpene from Flowers of Arnica montana

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