Synthesis and tyrosinase inhibition activity of trans -stilbene derivatives

A comprehensive review on tyrosinase inhibitors

“…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.…”

Natural and Bioinspired Phenolic Compounds as Tyrosinase Inhibitors for the Treatment of Skin Hyperpigmentation: Recent Advances

“…Alkyl resorcinols, such as 4-butylresorcinol or 4-hexylresorcinol, also exhibited very low IC50 values (Figure 19), particularly against the monophenolase activity (IC50 = 0.077 μM for 4-butylresorcinol) [167,168]. Rather low IC50 values have been determined also for resveratrol derivatives such as (E)-2,3-bis(4-hydroxyphenyl)acrylonitrile (IC50 = 5.06 μM) [169] and dihydrooxyresveratrol glucosides [170] (Figure 19). As to other natural phenol-inspired synthetic compounds [157][158][159][160][161], the best results have been reported for a carvacrol derivative containing a 3,5-dihydroxyphenyl moiety (IC 50 = 0.0167 µM) [159] ( Figure 19).…”

“…Coumarin dimers and derivatives containing a tetracyclic skeleton exhibited IC50 values in the range 1.7-2.9 μM [172] (Figure 20), whereas even higher activity has been reported for synthetic 3-heteroarylcoumarins [173] and umbelliferone-thiazolidinedione hybrids [174] (Figure 20). Of course, the most potent inhibitory activity is still attributed to resorcinol derivatives [162][163][164][165][166][167][168][169][170], although these compounds often suffer from toxicity concerns (the case of rhododendrol is emblematic [6][7][8]) (see below). Low IC 50 values (0.39-3.62 µM) have been reported for resorcinol alkyl glucosides [166] (Figure 19), whereas thiamidol, which is currently one of the most potent skin depigmenting agent on the market, is not so active against mushroom tyrosinase (IC 50 = 108 µM) [9].…”

“…Alkyl resorcinols, such as 4-butylresorcinol or 4-hexylresorcinol, also exhibited very low IC 50 values (Figure 19), particularly against the monophenolase activity (IC 50 = 0.077 µM for 4-butylresorcinol) [167,168]. Rather low IC 50 values have been determined also for resveratrol derivatives such as (E)-2,3-bis(4-hydroxyphenyl)acrylonitrile (IC 50 = 5.06 µM) [169] and dihydrooxyresveratrol glucosides [170] (Figure 19).…”

Exploring Anti-Prion Glyco-Based and Aromatic Scaffolds: A Chemical Strategy for the Quality of Life

“…Several synthetic approaches have been described for the synthesis of resveratrol, carried out by Wittig [ 149 ] or Horner-Wadsworth-Emmons reactions [ 150 ], Perkin condensations [ 151 ], and also through metal-catalysed processes, such as cross-metathesis [ 152 ] or cross-coupling reactions [ 153 , 154 ]. The most recent synthesis of resveratrol has been carried out by El-Deeb et al [ 155 ] and is shown in Scheme 29 .…”