Characterization of tyrosinase inhibitory constituents from the aerial parts of Humulus japonicus using LC-MS/MS coupled online assay

Yang, Hyo Hee; Oh, Kyung-Eon; Jo, Yang Hee; Ahn, Jong Hoon; Liu, Qing; Turk, Ayman; Jang, Jae Young; Hwang, Bang Yeon; Lee, Ki Yong; Lee, Mi Kyeong

doi:10.1016/j.bmc.2017.12.011

Cited by 24 publications

(6 citation statements)

References 39 publications

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“…Also, 2-(1-(coumarin-3-yl)-ethylidene) hydrazinecarbothioamide and 2-(1-(6-chlorocoumarin-3-yl) ethylidene)-hydrazinecarbothioamide demonstrated an irreversible inhibition of tyrosinase 277 . Recently, in the screening of natural products for the development of cosmetic ingredients, two major compounds, trans -N-coumaroyltyramine (IC 50 = 40.6 µM) and cis -N-coumaroyltyramine (IC 50 = 36.4 µM) from Humulus japonicus showed potent tyrosinase inhibition 290 .…”

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

“…Several stillbenes derivatives from natural and synthetic sources (Figure 8) have been investigated for their tyrosinase inhibition activity including: resveratrol from Morus alba 319 , Pleurotus ferulae 135 , vitis viniferae caulis 320 , Carignan grape juice 321 Artocarpus gomezianus 322 and Streptomyces avermitilis MA4680 323 and also, its derivatives fro m Dipterocarpaceae plants 324 and synthetic sources 325 , oxyresveratrol 326 from Morus australis 327 , Morus alba L (IC 50 = 0.10 ± 0.01 µM) 249 and Cudrania cochinchinensis (IC 50 = 2.33 µM) 255 , azo-resveratrol and its derivatives such as (E)-2-((2,4-dihydroxyphenyl)diazenyl) phenyl 4 methylbenzenesulfonate 328 and azo -oxyresveratrol 329 , trans -resveratrol from Streptomyces avermitilis MA4680 313 , a resveratrol dimer named gnetin C, from melinjo (Gnetum gnemon ) 330 . Also, several hydroxystillbene compounds from synthetic and semisynthetic sources 331 , 332 and from the extract of Veratrum patulum 333 , along with synthetic glycosides of resveratrol, pterostilbene, and pinostilbene 334 , synthetic trans-stilbene derivatives 335 , azastilbene analogs 336 , a newly synthesised stillbene 5-(6-hydroxy-2-naphthyl)-1,2,3-benzenetriol 337 , coumarin-resveratrol hybrids 290 , synthetic polyphenolic deoxybenzoins 218 , hydroxy substituted 2-phenyl-naphthalenes 338 and 4-(6-hydroxy-2-naphthyl)-1,3-bezendiol 339 have been studied for their inhibition activity against tyrosinase. However, based on the enzymatic assays, resveratrol did not inhibit the diphenolase activity of tyrosinase, but L-tyrosine oxidation by tyrosinase was suppressed in presence of 100 µM resveratrol.…”

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

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A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

774

471

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Tyrosinase is a multi-copper enzyme which is widely distributed in different organisms and plays an important role in the melanogenesis and enzymatic browning. Therefore, its inhibitors can be attractive in cosmetics and medicinal industries as depigmentation agents and also in food and agriculture industries as antibrowning compounds. For this purpose, many natural, semi-synthetic and synthetic inhibitors have been developed by different screening methods to date. This review has focused on the tyrosinase inhibitors discovered from all sources and biochemically characterised in the last four decades.

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Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

Section: Inhibitors From Natural Semisynthetic and Synthetic Sourcesmentioning

confidence: 99%

A comprehensive review on tyrosinase inhibitors

Zolghadri

Bahrami

Khan³

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

774

471

View full text Add to dashboard Cite

show abstract

“…, benzoic acid (8), cinnamic acid (9), 4-methoxycaffeic acid (10), and thymoquinol 2-O-βglucopyranoside (11), by the analysis of their spectroscopic data and comparison with literature values [19][20][21] . Compound 1 was isolated as brown syrup.…”

Section: Resultsmentioning

confidence: 99%

Effect of echinalkamide identified from Echinacea purpurea (L.) Moench on the inhibition of osteoclastogenesis and bone resorption

Chang

Lee

Kim

et al. 2020

Sci Rep

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Plant cell cultures have been exploited to provide stable production and new secondary metabolites for better pharmacological activity. Fractionation of adventitious root cultures of Echinacea purpurea resulted in the isolation of eleven constituents, including three new compounds. The structures of the three new compounds were determined to be an alkylamide (1), a polyacetylene (2) and a lignan (3) on the basis of combined spectroscopic analysis. To discover new types of antiresorptive agents, we screened for new compounds that regulate osteoclast differentiation, and survival. Among three new compounds, echinalkamide (compound 1) had considerably inhibitory effects on RANKL-induced osteoclast differentiation, and on proliferation of osteoclasts and efficiently attenuated osteoclastic bone resorption without toxicity. In addition, echinalamide treatment inhibited the osteoclast-specific gene expression level. Echinalkamide achieved this inhibitory effect by disturbing phosphorylation of MAPK and activation of osteoclast transcription factors c-Fos and NFATc1. Conclusionally, our study investigated that echinalkamide remarkably inhibited osteoclast differentiation and osteoclast specific gene expression through repression of the MAPK-c-Fos-NFATC1 cascade.

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“…For example, during the screening of natural products for the development of the cosmetic industry, it was found that the aerial extract of Humulus japanicus has tyrosinase inhibitory activity. This plant has been reported to be an antitumor and antioxidant too (Yang et al, 2017). During a screening study, the inhibitory effect of 70 plant species extracts on fungal tyrosinase activity was investigated and several plants with high inhibitory activity were introduced, two of which were Verbascum phoeniceum L. and Astragalus siliqusus Bioss (Hassani and Zarei, 2019).…”

Section: Discussionmentioning

confidence: 99%

Introduction and discussion about three types of fine grain products and their harvesters

Zarei

Babaei

2020

Int. J. Adv. Biol. Biomed. Res.

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Background: Melanogenesis begins with the oxidation of L-tyrosine to L-Dopa by tyrosinase. Inhibition of tyrosinase could be effective in the treatment of complications such as skin lesions, eczema and melasma. Inhibition of tyrosinase could be effective in the treatment of those complications. The aim of this study was to determine inhibitory activity on tyrosinase and antioxidant activity of Astragalus siliquosus Bioss. and Verbascum phoeniceum L. Methods: Methanol extracts of organs of the plants were prepared by maceration. Inhibitory effects of the extracts were evaluated in 96 wells at 492 nm wavelength. The antioxidant activity of the extracts was evaluated using DPPH free radical scavenging index and iron reduction test. Results: For A. siliquosus, maximum inhibitory activity was of its flower extract (97% inhibition and IC50=1.58 mg/mL) and of its stem extract (100% and IC50=2.1 mg/mL). For V. phoeniceum, the highest inhibitory activity was of its leaf extract (87% inhibition and IC50=3.2 mg/mL). Flower extract of A. siliquosus showed mixed Uncompetitive-noncompetitive pattern of inhibitory activity, while the extract of the V. phoeniceum leaf showed mixed Competitive-non-competitive inhibitory pattern. All aerial parts of the A. siliquosus had 100% antioxidant activity with EC50s of 0.089, 1.78, 1.25 mg/mL for its flower, leaf and stem, respectively. The leaves of the V. phoeniceum had a 100% antioxidant activity, with EC50 of 0.013 mg/mL. Conclusions: Methanol extracts of flower and leaf organs of A. siliquosus, and leaf organ of V. phoeniceum had a reasonable inhibitory effect on tyrosinase activity. Future studies could be focused on those organs to separate potential agents with pharmaceutical and cosmetic applications.

show abstract

Characterization of tyrosinase inhibitory constituents from the aerial parts of Humulus japonicus using LC-MS/MS coupled online assay

Cited by 24 publications

References 39 publications

A comprehensive review on tyrosinase inhibitors

A comprehensive review on tyrosinase inhibitors

Effect of echinalkamide identified from Echinacea purpurea (L.) Moench on the inhibition of osteoclastogenesis and bone resorption

Introduction and discussion about three types of fine grain products and their harvesters

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