Inhibitory effects of hinokitiol on tyrosinase activity and melanin biosynthesis and its antimicrobial activities

Zhu, Yujing; Qiu, Ling; Zhou, Jingjing; Guo, Hua-Yun; Hu, Yonghua; Li, Zhi-Cong; Wang, Qin; Chen, Qing‐Xi; Liu, Bo

doi:10.3109/14756360903476398

Cited by 32 publications

(21 citation statements)

References 25 publications

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“…These results indicated that compound 13 could bind to the enzyme and the enzyme-substrate complex in a concentration-dependent manner [ 37 ]. For inhibiting tyrosinase, the compound may function through two alternative mechanisms, competitive and uncompetitive modes [ 38 ].…”

Section: Resultsmentioning

confidence: 99%

New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes

Lin

Chen

Liu

et al. 2015

IJMS

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Nontoxic natural products useful in skin care cosmetics are of considerable interest. Tyrosinase is a rate-limiting enzyme for which its inhibitor is useful in developing whitening cosmetics. Pyracantha koidzumii (Hayata) Rehder is an endemic species in Taiwan that exhibits tyrosinase-inhibitory activity. To find new active natural compounds from P. koidzumii, we performed bioguided isolation and studied the related activity in human epidermal melanocytes. In total, 13 compounds were identified from P. koidzumii in the present study, including two new compounds, 3,6-dihydroxy-2,4-dimethoxy-dibenzofuran (9) and 3,4-dihydroxy-5-methoxybiphenyl-2ʹ-O-β-d-glucopyranoside (13), as well as 11 known compounds. The new compound 13 exhibited maximum potency in inhibiting cellular tyrosinase activity, the protein expression of cellular tyrosinase and tyrosinase-related protein-2, as well as the mRNA expression of Paired box 3 and microphthalmia-associated transcription factor in a concentration-dependent manner. In the enzyme kinetic assay, the new compound 13 acted as an uncompetitive mixed-type inhibitor against the substrate l-3,4-dihydroxyphenylalanine and had a Km value against this substrate of 0.262 mM, as calculated using the Lineweaver–Burk plots. Taken together, our findings show compound 13 exhibits tyrosinase inhibition in human melanocytes and compound 13 may be a potential candidate for use in cosmetics.

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Section: Resultsmentioning

confidence: 99%

New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes

Lin

Chen

Liu

et al. 2015

IJMS

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“…Takahashi et al (2010) examined the inhibitory effects of three isomers of thujaplicins (α, ß, γ) on mushroom tyrosinase activity and showed that all these compounds inhibit the enzyme activity in a dose dependent manner, and γ-thujaplicin was found to be the most potent inhibitor among them. Zhu et al (2010) showed that hinokitiol effectively inhibited both cellular tyrosinase activity and melanin biosynthesis in B16 melanoma cells with significant cytotoxicity.…”

Section: And Polyphenol Oxidase Activitymentioning

confidence: 99%

“…It was found that hinokitiol could also inhibit the proliferation of Salmonella enteritidis, Escherichia coli, Bacillus subtilis, Staphylococcus aureus, Klebsiella pneumoniae, and Ralstonia solanacearum to different extents; the antibacterial activity against S. enteritidis, E. coli, and B. subtilis was most effective (Zhu et al 2010). Zhao et al (2009) demonstrated antibacterial activities of hinokitiol against heterotrophic bacteria, such as Sphingomonas paucimobilis and Brevundimonas vesicularis, which were isolated from hemodialysis fluid.…”

Section: Antibacterial Activity Of Troponoidsmentioning

confidence: 99%

The Biological Activities of Troponoids and Their Use in Agriculture A Review

Saniewski

Horbowicz

Kanlayanarat

2014

Journal of Horticultural Research

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Chemical compounds containing the tropone structure (2,4,6-cycloheptatrien-1-one), in their molecule, called troponoids, characterized by a seven-membered ring, are distributed in some plants, bacteria and fungi, although they are relatively rare. ß-Thujaplicin (2-hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-one), also known as hinokitiol, is a natural compound found in several plants of the Cupressaceae family. Besides hinokitiol, related compounds were identified in Cupressaceae trees. It has been demonstrated that hinokitiol and its derivatives have various biological effects, such as antibacterial, antifungal, insecticidal, antimalarial, antitumor, anti-ischemic, iron chelating and the inhibitory activity against polyphenol oxidase activity. Activity similar to ß-thujaplicin has tropolone and its derivatives, which are not present nature. Due to the high scientific and practical interest, synthetic ß-thujaplicin and other troponoids have been produced for many years. In this review, the major biological effects of troponoids, mostly ß-thujaplicin and tropolone, on tyrosinase and polyphenol oxidase activity, ethylene production, antibacterial, antifungal and insecticidal activities, and biotransformation of ß-thujaplicin by cultured plant cells are presented. Accumulation of ß-thujaplicin and related troponoids has been shown in cell cultures of Cupressus lusitanica and other species of Cupressaceae. The biosynthetic pathway of the troponoids in plants, bacteria and fungi has been also briefly described.

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“…The biosynthetic pathway for melanin formation includes two steps: the hydroxylation of monophenol to o-diphenol and the oxidation of diphenol to o-quinones [1][2][3][4]. Furthermore, in some vegetables and fruits, tyrosinase is responsible for enzymatic browning, and it also plays a vital role in vegetables and fruits processing [4][5][6][7][8]. Tyrosinase inhibitors have attracted much attention recently.…”

Section: Introductionmentioning

confidence: 99%

“…antimicrobial activities [16,7]. And many of the inhibitors consist of compounds which structurally analogous to phenolic substrate.…”

Section: Introductionmentioning

confidence: 99%

Inhibitory effects of naphthols on the activity of mushroom tyrosinase

Lin

Jia

et al. 2012

International Journal of Biological Macromolecules

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Inhibitory effects of hinokitiol on tyrosinase activity and melanin biosynthesis and its antimicrobial activities

Cited by 32 publications

References 25 publications

New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes

New Whitening Constituents from Taiwan-Native Pyracantha koidzumii: Structures and Tyrosinase Inhibitory Analysis in Human Epidermal Melanocytes

The Biological Activities of Troponoids and Their Use in Agriculture A Review

Inhibitory effects of naphthols on the activity of mushroom tyrosinase

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