N-trans-Feruloyltyramine as a Melanin Biosynthesis Inhibitor

Efdi, Mai; Ohguchi, Ken-ichi; Akao, Yukihiro; Nozawa, Yoshinori; Koketsu, Mamoru; Ishihara, Hideharu

doi:10.1248/bpb.30.1972

Cited by 26 publications

(19 citation statements)

References 25 publications

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“…The other assignments of carbons and hydrogens were determined based on all spectral data and in comparison with the literature ones, 22 which allowed to unambiguously identify substance 4 as being Ntrans-feruloyltyramine (Figure 3), substance already isolated from other vegetal species 23 with studies demonstrating its action against weeds and improvement of seed germination, 24 as well as its activity as a melanin biosynthesis inhibitor, 22 being described for the first time in the family Malvaceae.…”

Section: Resultsmentioning

confidence: 99%

Steroidal and phenolic compounds from Sidastrum paniculatum (L.) Fryxell and evaluation of cytotoxic and anti-inflammatory activities

et al. 2010

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Recebido em 28/5/09; aceito em 17/11/09; publicado na web em 2/3/10Sidastrum paniculatum (L.) Fryxell belongs to the family Malvaceae and is popularly known as "malva roxa" or "malvavisco". The phytochemical study of the hexane, CHCl 3 and EtOAc phases from the crude ethanol extract of S. paniculatum led to the isolation of six compounds: a mixture of b-sitosterol and stigmasterol, 4-methoxy-3-hydroxybenzoic acid, 4-methoxy-3-hydroxybenzaldehyde, N-trans-feruloyltyramine and kaempferol-3-O-b-D-(6''-E-p-coumaroyl) glucoside. The structural identification of the compounds was made on the basis of spectroscopic methods such as IR, 1 H and 13 C NMR with the aid of including two-dimensional techniques, besides comparison with literature data. The b-sitosterol and stigmasterol mixture showed a significant anti-inflammatory activity.

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Section: Resultsmentioning

confidence: 99%

Steroidal and phenolic compounds from Sidastrum paniculatum (L.) Fryxell and evaluation of cytotoxic and anti-inflammatory activities

et al. 2010

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“…Tyrosinase, the enzyme catalyzing the rate‐limiting step in melanin biosynthesis, is a well‐characterized marker of differentiation in melanocytes and melanoma cells (Efdi et al ., ). Thus, to investigate the mechanism responsible for the decreased pigmentation, changes in the protein level of the important melanogenic enzyme, tyrosinase was examined by western blot analysis with a specific antibody against tyrosinase.…”

Section: Resultsmentioning

confidence: 97%

Modulation of Melanin Synthesis by Rengyolone Isolated from the Root of Eurya emarginata in Melan‐a Cells

Kim

Jeong

Hwang

et al. 2013

Phytotherapy Research

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In the course of screening for the melanogenesis inhibitors, rengyolone was isolated from Eurya emarginata (Thumb) Makino. Its chemical structure was determined on the basis of spectroscopic analysis including mass spectroscopy and nuclear magnetic resonance analysis. Rengyolone inhibited potent melanogenesis in melan-a cells with an IC50 value of 65 μM without cytotoxicity. Also, rengyolone showed a melanin biosynthesis inhibition zone in a culture plate of Streptomyces bikiniensis, which is commonly used as an indicator organism. Moreover, rengyolone dramatically reduced protein expression of melanogenic enzyme, tyrosinase. Furthermore, rengyolone presented inhibition on the body pigmentation in zebrafish model system and decreased melanin contents and tyrosinase activity. These results suggest that rengyolone isolated from E. emarginata may be an effective skin-whitening agent that regulates the expression of melanogenic enzymes.

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“…This suggested that TDs are capable of occupying both binding domains with structural flexibility and may serve as a source of full and/or partial agonists for PPARγ. Some of the TDs were previously studied and reported to possess diverse biological activities including antitubercular activity [34], inhibitors of bacterial efflux pump, melanin synthesis [35], melanocyte-tyrosinase [36] and antifungal activities [37]. However, their antidiabetic potentials including modulation of PPARs were not reported.…”

Section: In Silico Molecular Dockingmentioning

confidence: 99%

In search for potential antidiabetic compounds from natural sources: docking, synthesis and biological screening of small molecules from Lycium spp. (Goji)

Yalamanchili

Chittiboyina

Haider

et al. 2020

Heliyon

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Current clinical antidiabetic drugs, like rosiglitazone 1, have been implicated in some serious side effects like edema, weight gain, and heart failure, making it necessary to find alternative agents. Partial agonists of peroxisome-proliferator activated receptor-gamma (PPARγ) were determined to possess improved insulin sensitivity without undeseirable side-effects when compared to full agonists of PPARγ, like rosiglitazone 1. The traditional Chinese medicine (TCM) plants, Goji (Lycium barbarum and Lycium chinense) are widely used for treating symptoms related to various diseases including diabetes and hypertension. Twenty-seven reported compounds from Goji were docked into both partial-and full-agonist binding sites of PPARγ. Amongst the docked compounds, phenylethylamide-based phytochemicals (5-9) (termed as tyramine-derivatives, TDs) were found to possess good docking scores and binding poses with favorable interactions. Synthesis of 24 TDs, including three naturally occuring amides (6, 8, 9) were synthesized and tested for PPARγ gene induction with cell-based assay. Three compounds showed similar or higher fold induction than the positive control, rosiglitazone. Among these three active TDs, trans-N-feruloyloctopamine (9) and tyramine derivatives-enriched extract (TEE) (21%) of the root bark of L. chinense were further studied in vivo using db/db mice. However, both TEE as well as 9 did not show significant antidiabetic properties in db/db mice. In vivo results suggest that the proposed antidiabetic property of Lycium species may not be due to tyramine derivatives alone. Further studies of tyramine derivatives or enriched extract(s) for other bioactivities like hypocholesterolemic activities, and studies of novel isolated compounds from Goji will enable a more complete understanding of their bioactivities.

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N-trans-Feruloyltyramine as a Melanin Biosynthesis Inhibitor

Cited by 26 publications

References 25 publications

Steroidal and phenolic compounds from Sidastrum paniculatum (L.) Fryxell and evaluation of cytotoxic and anti-inflammatory activities

Steroidal and phenolic compounds from Sidastrum paniculatum (L.) Fryxell and evaluation of cytotoxic and anti-inflammatory activities

Modulation of Melanin Synthesis by Rengyolone Isolated from the Root of Eurya emarginata in Melan‐a Cells

In search for potential antidiabetic compounds from natural sources: docking, synthesis and biological screening of small molecules from Lycium spp. (Goji)

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