The Hunt for Natural Skin Whitening Agents
Abstract
:1. Introduction
2. Targeting Tyrosinase as the Key Enzyme of Melanogenesis
3. Different Modes of Reducing Melanin Production in Melanocytes and Skin
4. Induction of Pigmentation
5. Cosmetic Use of (natural) Agents for Skin Whitening
Abbreviations
AA | Ascorbic Acid |
ACTH | adrenocorticotropic hormone |
AO | antioxidant |
Arb | Arbutin |
bFGF | basic fibroblast growth factor |
BMP | bone morphogenetic proteins |
cAMP | cyclic AMP |
CT | clinical trials |
DNJ | 1-deoxynojirimycin |
DPPH | 1,1-diphenyl-2-picrylhydrazyl |
ET-1 | endothelin-1 |
ERK | extracellular signal-regulated kinases |
GP | guinea pig |
HGF | hepatocyte growth factor |
HQ | hydroquinone |
IC50 | half maximal inhibitory concentration |
Il1α | interleukin 1α |
KA | kojic acid |
l-DOPA | l-dihydroxyphenylalanine |
MC1R | melanocortin-1 receptor |
MITF | microphtalmia transcription factor |
(α)-msh | (α)-melanocyte stimulating hormone |
MT | melanosome transport |
nHEM | normal human epidermal melanocytes |
8OHdg | 8 hydroxy deoxy guanosine |
ORAC | oxygen radical absorbance capacity |
PKA | protein kinase A |
PKC | protein kinase C |
PPAR | peroxisome proliferator- activated receptor |
PTU | phenylthiourea |
SAR | structure activity relationship |
sAPP | soluble N-terminal ectodomain of the beta-amyloid precursor protein |
SCF | stem cell factor |
SEM | skin equivalent model |
Sox | Sry-related HMG box |
TE | tyrosinase expression |
TI | tyrosinase inhibition |
(c) | competitive mode |
(nc) | non competitive mode |
(m) | mixed mode of inhibition |
TNF-α | tumor necrosis factor-α |
TRP | tyrosinase related protein |
UV | ultraviolet |
UVA | ultraviolet A |
UVB | ultraviolet B |
UVR | ultraviolet radiation |
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Source | Compounds (type) | Mode of action tested* | Refs. | |
---|---|---|---|---|
TI | comments | |||
Chouji and Yakuchi extracts, crude drugs | eugenol, yakuchinone A, ferulic acid, curcumin and yakuchinone B | TI (c) | [18] | |
Anacardium occidentale, cashew fruit | 6-[8(Z),11(Z),14-pentadecatrienyl]-salicylic acid and 5-[8(Z),11(Z),14-pentadecatrienyl]resorcinol | TI (c) | [19] | |
Bolivian medicinal plants, Buddleia coriacea, Gnaphalium cheiranthifolium, and Scheelea princeps. | phenolic | TI | [20] | |
Artocarpus gomezianus. | among eight other compounds norartocarpetin (5) and resveratrol (8) were isolated | 5,8 were most potent TI | [21] | |
Artocarpus incisus | flavonoids, stilbenes and related 4-substituted resorcinols | TI | 4-substituted recorcinol increases TI (c) | [15] |
Stryphnodendron barbatimao, Portulaca pilosa, Cariniana brasiliensis, Entada africana and Prosopis africana. Five plants out of 67 tropical plants | unknown | strong TI | TI comparable to Morus alba as positive control | [22] |
Pulsatilla cernua | 3,4-dihydroxycinnamic acid (1) 4-hydroxy-3-methoxycinnamic acid (2) | 2 > other TI > 1 1,2 (nc) | [23] | |
galls of Rhus javanica | Tannic acid | TI | - | [24] |
Sophora flavescens | prenylated flavonoids; kuraridin, kurarinone and norkurarinol | strong TI > KA | C8 and C5 substitutionis essential for TI | [16] |
Sophora flavescens | sophoraflavanone G, kuraridin, and kurarinone | TI > KA | [25] | |
Veratrum patulum | hydroxystilbene compounds; resveratrol, oxyresveratrol, and their analogs | potent TI | cellulase treatment improved TI | [17] |
Phellinus linteus | cerebroside B (1), protocate-chualdehyde (2), 5-hydroxymethyl-2-furaldehyde (HMF) (3), succinic acid (4), fumaric acid (5) | 2,3 TI 2 > 3 2 (c) 3 (nc) | [26] | |
Ecklonia stolonifera. edible brown alga out of 17 seaweed extracts | phloroglucinol derivatives [phloroglucinol (1), eckstolonol (2), eckol (3), phlorofucofuroeckol A (4), and dieckol (5)]. | 1,2 TI (c) 3–5 (nc) | TI similar to arbutin | [27] |
39 seashore plant species, Japan: Hibiscus tiliaceus, Carex pumila, and Garcinia subelliptica | GS contained 2 biflavonoids; 2R,3S-5, 7,4′,5″,7″,3‴,4‴-heptahydroxy-flavanone[3-8″] flavone (1) and 5,7,4′,5″,7″,3‴,4‴-heptahydroxy[3–8″] biflavanone (2) | both strong TI 1 > KA | [28] | |
Glycyrrhiza uralensis Glycyrrhiza inflate Licorice | liquiritin(1), licuraside (2), isoliquiritin(3), liquiritigenin(4) and licochalcone A (5) | 2,3 and 5 potent TI (c) | [29] | |
Trifolium balansae | three steroids, stigmast-5-ene-3 beta,26-diol (2), stigmast-5-ene-3-ol (3) and campesterol (4) | 2,3 and 4 potent TI 2 > 3,4 | [30] | |
Amberboa ramosa Jafri | cycloartane type triterpenoids; eight compounds identified. 3β,21,22,23-tetrahydroxycycloart-24 (31),25(26)-diene (cmpd. 7) | 7 most potent TI > KA | SAR studies | [31] |
Sake lees | triacylglycerols; triolein (1) and trilinolein (2) | TI 1,2 (nc) TI 2 > 1 | PI in E coli (2) | [32] |
Garcinia kola | screening 21 families of medicinal plants from West and Central Africa. 5 extracts selected with G. kola showing good TI; five biflavanones identified | TI > 60% IC50 > KA | [33] | |
Marrubium velutinum and Marrubium cylleneum | Screening of 45 metabolites. Flavonoids (1), phenylethanoid glycosides (2), phenolic acids (3) | 1,2 moderate TI, 3 < 2 | [34] | |
Lichen species; Graphidaceae family(1) Usnea ghattensis (2), Heterodermia podocarpa, Arthothelium awasthii (3) and Parmotrema tinctorum | unknown | TI (1) 30–78% | antioxidant, antimicrobial, antityrosinase IC50 (2,3) similar or less than other TIs | [35,36] |
Sophora flavescens | sophoraflavanone G (1), kurarinone (2) and kurarinol (3) | strong TI 1,2 (nc) 3 (c) | 1,2 antibacterial 3 PI in SB MMS on 3 | [37] |
50 crude drugs Glycyrrhiza glabra, Morus alba, Syzygium aromaticum, Citrus aurantifolia, Cypreae moneta, Punica granatum and Citrus aurantium | yes All < KA | [38] | ||
Ganoderma lucidum | yes | [39] | ||
Arbutus andrachne | Arbutin, hydroquinone, β-sitosterol and ursolic acid present in extracts | yes | [40] | |
Morus alba L. and Morus rotundiloba Koidz Mulberry | betulinic acid (present) | yes | anti inflammatory | [41] |
Guioa villosa | sesquiterpene diglycosides; crenulatosides E, F and G (1 – 3) betulin (14), lupeol (15) and soyacerebroside I (16) | no strong TI | [42] | |
Broussonetia kazinoki. | 1,3-diphenylpropanes: kazinol C (1), D (2), F (3), broussonin C (4), kazinol S (5) and kazinol T (6) | 1,3–5 (c) 4; max TI | - - | [43] |
Artocarpus heterophyllus | 15 compounds. norartocarpetin (4) and artocarpesin (6) | yes 5 cmpds > KA | - - | [44,45] |
Paeonia suffruticosa | kaempferol (I), quercetin (II), mudanpioside B (III), benzoyl-oxypaeoniflorin (IV), mudanpioside H (V), and pentagalloyl-β-d-glucose (VI) | yes I to V (c) VI (nc) | - - | [46] |
Source | Compounds (type) | Mode of action tested(*)(**) | Refs. | ||
---|---|---|---|---|---|
TI | PI | other | |||
Pityrosporum ovale | Azelaic acid; C9-dicarboxylic acid | yes | yes | - | [75] |
Aspergillus niger and Aspergillus penicillium | Kojic acid; 5-hydroxy-2-(hydroxymethyl)-γ-pyrone | Yes (c,m) | - | - | [76,77] |
Arctostaphylos uva-ursi bearberry | Arbutin; hydroquinone glucoside β-d-gluconopyranoside | yes (c,m,nc) | - | - | [13,78] [79] |
Aloe vera | Aloesin; C-glycosylated chromone | yes (nc) | - | - | [9,13,80] |
Artocarpus incisus (best of) 23 heart wood species from Papua New Guinea. | (+)-dihydromorin, chlorophorin, (+)-norartocarpanone, 4-prenyl-oxyresveratrol, artocarbene, artocarpesin and isoarto-carpesin | yes ≈ KA | yes (B16 and GP) | - | [81] |
Morus alba Rheum undulatum | 1. Oxyresveratrol 2. Hydroxystilbene | yes > KA (nc) yes | - | 1. no effect on expression or synthesis | [82] |
Morus alba | Mulberroside F (moracin M-6, 3′-di-O-beta-d-glucopyranoside | yes | yes (melan-a) | mild anti-oxidant SO scavenger <KA | [83] |
Citrus fruit peel | 3′,4′,5,6,7,8-hexamethoxy-flavone (nobiletin) | yes > KA | antimutagenic | [84] | |
Ramulus mori (young twigs of Morus alba) | 2,3′,4,5′-tetrahydroxy-stilbene (2-oxyresveratrol) | yes (c) | yes (GP + UV) | no effect on expression or synthesis non-toxic | [85] |
Glycyrrhiza glabra Licorice extract | glabrene and 2′,4′,4-tri-hydroxychalcone | yes | yes | [86] | |
Grape seed | proanthocyanidin | yes | yes (B16, GP + UV) | antioxidant activity, 8OHdG | [56] |
Aspergillus fumigatus and Saccharomyces cerevisiae | melanin degrading enzymes | - | - | [70] | |
Carthamus tinctorius safflower seeds | 1) N-feruloylserotonin,2) N-(p-coumaroyl)serotonin, and 3) acacetin | yes, 1,2 > arbutin | yes (SB, B16). 1,2 > arbutin | [49] | |
Glycyrrhiza uralensis | Glycyrrhisoflavone (1) and glyasperin C(2) | yes | yes (B16) 1 > 2 | [87] | |
Punica granatum Pomegranate | ellagic acid | yes ≈ Arb | yes (GP + UV) ≈ AA | [57] | |
Fish, Poultry | vitamin B3 derivative, niacinamide | no | no | MT inh. Mc/Kc cocult. CT | [53] |
Piper longum | piperlonguminine | no | yes (B16 + msh) | Tyr mRNA red. cAMP pathway via MITF inh. | [88,89] |
Angelica dahurica | isoimperatorin imperatorin | no | yes (B16) | Tyr protein + mRNA red. | [90] |
Artocarpus lakoocha heartwood | oxyresveratrol | yes | Nd | CT (female volunteers) > KA > licorice | [60] |
Astragalus taschkendicus | askendoside B | yes | Nd | [91] | |
Spatholobus suberectus Dunn (Leguminosae) Chinese herb | Butin (most effective compound) | yes | yes (nHEM) | Tyr,Trp-1 and Trp-2 reduced (WB,qPCR) | [64] |
Sophora japonica and Spatholobus suberectus out of 25 Chinese Herbs | high phenolic content, e.g., gallic acid | yes | yes (nHEM) | AO activity (DPPH) | [92] |
Galla Chinensis Radix Clematidis out of 90 Chinese Herbs | unknown | yes | yes (Mel-ab, melan-a, melan-a/SP1 cocult.) | Effects on Tyr, Trp-1 and Trp-2expression | [52] |
Kaempferia pandurata | chalcone compounds, isopanduratin A and 4-hydroxypanduratin A | yes > PTU | yes (melan-a) > PTU | Tyr protein reduced | [93] |
Corn bran | Polyamine conjugates, N,N′-dicoumaroylputrescine (DCP), N-p-coumaroyl-N′-feruloylputrescine (CFP), and N,N′-diferuloyl-putrescine (DFP) | yes DCP > AA | yes (B16) DFP > Arb | AO activity (DPPH) | [94] |
Podocarpus macrophyllus | 2,3-dihydro-4′,4‴-di-O-methylamentoflavone | yes | yes (nHEM) | Trp-2 mRNA reduced | [95] |
Longan seed | corilagin, gallic acid and ellagic acid or other phenolic/flavonoid glycosides and ellagitannins | yes | n.d. | AO activity (DPPH and ORAC assays) | [71] |
Gastrodia elata Blume Orchidaceae | (synthetic) p-hydroxybenzyl alcohol | yes (Irrev) | yes (B16, mouse MC-KC cocult.) | AO; radical scavenger | [51,96] |
Sophora flavescens | 1) kurarinol, 2) kuraridinol, and 3) trifolirhizin | yes 1,2 > KA 1,2 (nc) | yes (B16) | [97] | |
Cucumis sativus | Lutein | no | yes (B16) | Tyr protein reduced | [98] |
Lespedeza cyrtobotrya | Haginin A | yes (nc) | yes (melan-a) GP (+UV) zebra fish | MITF, Tyr, Trp-1 reduced. Erk induced | [59] |
Malpighia emarginata Acerola fruit | cyanidin-3-alpha-O-rhamnoside. pelargonidin-3-α-O-rhamnoside | yes | yes (B16) GP (+UV) | [11] | |
Coccoloba uvifera Sea grape | unknown | yes (nHEM) | AO; reduces IL-1alpha, TNF-alpha and alpha-MSH in nHEM + UV | [74] | |
Salicornia herbacea, halophyte | yes | yes (B16) | AO activity | [99] | |
Allium species such as garlic and onions. | 1-propylmercaptan | yes ≈ KA | yes ≈ KA | [100] | |
Willughbeia coriacea Phyllanthus urinaria out of 14 medicinal plants Central Kalimantan | unknown | yes yes | yes (B16) yes (B16) | AO assay DPPH | [101] |
Rhus Ghinensis; Chinese galls | 3 Gallotannins; 2,3,4,6-tetra-O-galloyl-d-glucopyranose, 1,2,3,6-tetra-O-galloyl-β-d-glucopyranose, and 1,2,3,4,6-penta-O-galloyl-β-d-glucopyranose | yes (nc) | Yes (B16 + UVA; MSH) | [102] | |
Rhus succedanea | 10′(Z)-heptadecenyl-hydroquinone | yes > HQ | yes > HQ (B16) | [103] | |
Polygonum cuspidatum. Paris polyphylla Vitex negundo | Physcion (anthraquinone + anthraquinone analog) (+)-Lyoniresinol | yes ≈ KA yes > KA yes > KA | n.d. n.d. n.d, | Good skin permeation | [10,104] [105] |
Raspberry | Tiliroside | yes | Yes (B16) | >Arb | [106] |
Erigeron breviscapus Chinese herb | (2Z,8Z)-matricaria acid methyl ester | no | yes (B16, elan-a > Arb | Tyr protein reduced? | [107] |
Alpinia galanga and Curcuma aromatica medicinal plants | eugenol and curcuminoids possible active ingredients | yes | yes (G361 ma cells + UVA) | AO defence | [108] |
Grape seed | oligomeric proanthocyanidins | - | yes, nHEM + UV | effects on TE, Trp-1 and Trp-2 expression AO activity | [65] |
Company | Product | Ingredients | Documentation; in Vitro/in Vivo Effect |
---|---|---|---|
Revitol | Skin Brightener | Arbutin, Lumiskin (diacetyl boldine), Z Whitener (new natural ingredient, unknown) + vitamins A,C and E and other natural extracts (antioxidants) | Lumiskin TM: action on tyrosinase expression based on principle described by Fuller 2000 [128] http://naturalskincareformula.com/ |
Premium Naturals | Skinbright | Arbutin, Kojic Acid, Lemon Extract | www.whiterskin.com/ |
Sisquoc | Lucederm | Niacinamide, α-Arbutin, Kojic Acid, Mulberry, Bearberry, Licorice, Lemon | www.whiterskin.com/ [29,53,82,83] |
LIBiol | Synerlight | Actinidia Chinensis (Kiwi) Fruit, Sophora Angustifolia Root | http://www.gattefossecanada.ca/ |
Bayer HealthCare | Mandresy extract | Buddleja axillaris leaves; extract rich in orthocinnamic compounds and flavonoids, verbascoside & luteolin | TI (mushroom); PI (nHEM + UV); reduces dendricity; in vivo brightening 8 volunteers (Chromameter) www.serdex-plantextracts.com: United States Patent Application 20090028969 |
Civant Skin care | Meladerm | Kojic Acid, α-Arbutin, Niacinamide, Mulberry, Bearberry, Licorice, Tego® Cosmo C250, Gigawhite, Lemon Juice, Emblica TegoCosmo; a natural amino acid derivative that belongs to the class of guanidine compounds Giga white:plant extracts from the Swiss alps; Malva Sylvestris, Mentha Piperita, Primula Veris, Alchemilla Vulgaris, Veronica Officinalis, Melissa Officinalis, Achillea Millefolium | niacinamide, mulberry and licorice (refs. [29,53,82,83]) www.whiterskin.com/; http://www.whiterskin.com/studies/cosmo.pdf http://www.whiterskin.com/studies/giga.pdf |
Juju Cosmetics | Tosekki whitening cream | Glycyrrhetinic acid, Ginseng, Houttuynia, Yeast, Coix, Horse Chestnut, Arica, Grape Leaf, Ypericum, Ivy, Witch Hazel, Sophora Root, Mulberry Bark, Peony Root, Japanese Angelica Root, Rose Fruit and other ingredients. | Glycyrrhetinc acid; Sophora Root; Peony Root; Mulberry Bark (refs. [25,29,38,46,82,83,86]) http://beautyknot.wordpress.com/2009/02/27/juju-cosmetics-tosekki-whitening-cream/ |
Lipotec | Chromabright | dimetylmethoxy chromanyl palmitate | TI (mushroom + human); PI (nHEM) photoprotective; in vivo brightening 20 Asian females (Chromameter) www.lipotec.com ; Patent; http://www.maxworth.co.th/max/pdf/ES291%20Chromabriht.pdf |
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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Smit, N.; Vicanova, J.; Pavel, S. The Hunt for Natural Skin Whitening Agents. Int. J. Mol. Sci. 2009, 10, 5326-5349. https://doi.org/10.3390/ijms10125326
Smit N, Vicanova J, Pavel S. The Hunt for Natural Skin Whitening Agents. International Journal of Molecular Sciences. 2009; 10(12):5326-5349. https://doi.org/10.3390/ijms10125326
Chicago/Turabian StyleSmit, Nico, Jana Vicanova, and Stan Pavel. 2009. "The Hunt for Natural Skin Whitening Agents" International Journal of Molecular Sciences 10, no. 12: 5326-5349. https://doi.org/10.3390/ijms10125326