Arbutin

CAS# 497-76-7

Arbutin

Catalog No. BCN6307----Order now to get a substantial discount!

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Chemical structure

Arbutin

3D structure

Chemical Properties of Arbutin

Cas No. 497-76-7 SDF Download SDF
PubChem ID 346 Appearance White powder
Formula C12H16O7 M.Wt 272.26
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms p-Arbutin; β-Arbutin
Solubility DMSO : ≥ 50 mg/mL (183.65 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name 2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
SMILES C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O
Standard InChIKey BJRNKVDFDLYUGJ-UHFFFAOYSA-N
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Arbutin

1 Arbutus sp. 2 Arctostaphylos sp. 3 Bergenia sp. 4 Calluna sp. 5 Chimaphila sp. 6 Erica sp. 7 Origanum sp. 8 Picrasma sp. 9 Rhododendron sp. 10 Sedum sp. 11 Vaccinium sp. 12 Viburnum sp. 13 Zanthoxylum sp.

Biological Activity of Arbutin

DescriptionArbutin is a tyrosinase inhibitor with an IC50 of 1.09 mM, which has gastroprotective, whitening, anti- age, anti-oxidant , anti-inflammatory, a depigmenting effects and UVB/ UVC filter. Arbutin has mutagenicity in mammalian cells after activation by human intestinal bacteria.
TargetsROS | NO | NOS | COX | TNF-α | NF-kB | IL Receptor | Tyrosinase
In vitro

Alleviation effect of arbutin on oxidative stress generated through tyrosinase reaction with L-tyrosine and L-DOPA.[Pubmed: 25297374]

BMC Biochem. 2014 Oct 9;15:23.


METHODS AND RESULTS:
Hydroxyl radical that has the highest reactivity among reactive oxygen species (ROS) is generated through L-tyrosine-tyrosinase reaction. Thus, the melanogenesis might induce oxidative stress in the skin. Arbutin (p-hydroxyphenyl-β-D-glucopyranoside), a well-known tyrosinase inhibitor has been widely used for the purpose of skin whitening. The aim of the present study was to examine if Arbutin could suppress the hydroxyl radical generation via tyrosinase reaction with its substrates, L-tyrosine and L-DOPA. The hydroxyl radical, which was determined by an electron spin resonance-spin trapping technique, was generated by the addition of not only L-tyrosine but L-DOPA to tyrosinase in a concentration dependent manner. Arbutin could inhibit the hydroxyl radical generation in the both reactions.
CONCLUSIONS:
It is presumed that Arbutin could alleviate oxidative stress derived from the melanogenic pathway in the skin in addition to its function as a whitening agent in cosmetics.

Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria.[Pubmed: 16904805 ]

Food Chem Toxicol. 2006 Nov;44(11):1940-7.

Arbutin (hydroquinone-beta-D-glucopyranoside) is present in various food plants. Its aglycone, hydroquinone, is mutagenic and carcinogenic.
METHODS AND RESULTS:
We investigated whether hydroquinone may be released under conditions encountered in the human gastrointestinal tract. Arbutin was stable in artificial gastric juice. Fecal slurries from nine human subjects completely converted Arbutin (2 mM) into hydroquinone. Four of nine representative human intestinal species investigated, namely Eubacterium ramulus, Enterococcus casseliflavus, Bacteroides distasonis, and Bifidobacterium adolescentis, deglycosylated Arbutin at rates of 21.08, 16.62, 8.43 and 3.59 nmol x min(-1) x (mg protein)(-1), respectively. In contrast, homogenates from small intestinal mucosa and cytosolic fractions from colon mucosa deglycosylated Arbutin at substantially lower rates: 0.50 and 0.09 nmol x min(-1) x (mg protein)(-1), respectively. Arbutin, unlike hydroquinone, did not induce gene mutations in Chinese hamster V79 cells in the absence of an activating system. However, in the presence of cytosolic fractions from E. ramulus or B. distasonis, Arbutin was strongly mutagenic. Cytosolic fraction from Escherichia coli, showing no Arbutin glycosidase activity, was not able to activate Arbutin in this model system.
CONCLUSIONS:
The release of the proximate mutagen hydroquinone from Arbutin by intestinal bacteria in the immediate vicinity of the colon mucosa may pose a potential risk.

In vivo

Gastroprotective activities of Turnera diffusa Willd. ex Schult. revisited: Role of arbutin.[Pubmed: 22374081]

J Ethnopharmacol. 2012 May 7;141(1):273-81.

Turnera diffusa Willd. ex Schult. has been used for the treatment of several human disorders including peptic ulcer. The current study is an attempt to evaluate the anti-ulcerogenic activities of Arbutin, a major constituent of Turnera diffusa on two ulcer models. The possible involvement of lipid peroxidation, nitric oxide, IL-6, IL-10, TNF-α and mucus barrier mechanism has been investigated.
METHODS AND RESULTS:
Effects of Arbutin on ulcer index, gastric juice acidity, mucus content and histochemistry, gross and histological gastric lesions, nitric oxide, cytokines levels (IL-6, IL-10 and TNF-α), and thiobarbituric acid reactive substances (TBARS), were evaluated in aspirin or ethanol-induced ulcer in vivo. Acute toxicity of Arbutin was also examined in rodent model. MTT assay was used to assess the cytotoxicity of the compound on normal liver cells (WRL-68). Pre-treatment with Arbutin or omeprazole protected the gastric mucosa as seen by reduction in ulcer area and mucosal content, reduced or absence of edema, inflammation and leucocytes infiltration on both models. Arbutin significantly (P<0.05) lowered the elevated TBARS level into gasteric homogenate. Arbutin did not produce significant inhibition of NO. This natural compound has modulated the levels of interleukin-6, interleukin-10 and TNF-α. No in vitro or in vivo toxicities for Arbutin were observed.
CONCLUSIONS:
Thus it can be concluded that Turnera diffusa possesses anti-ulcer activity, which could be attributed to lipid peroxidation inhibitory, immuno modulatory and anti-oxidant mechanisms of Arbutin but not to the intervention with nitric oxide inflammation pathway.

Protocol of Arbutin

Cell Research

Anti-inflammatory effects of arbutin in lipopolysaccharide-stimulated BV2 microglial cells.[Pubmed: 22487852]

Inflamm Res. 2012 Aug;61(8):817-25.

Arbutin, which is found in the genus Arctostaphylos, is an anti-oxidant and a depigmenting agent. The present study was designed to validate the anti-inflammatory effect of Arbutin.
METHODS AND RESULTS:
The anti-inflammatory properties of Arbutin were studied using a lipopolysaccharide (LPS)-stimulated murine BV2 microglial cells model. As inflammatory parameters, the production of nitric oxide (NO), inducible NO synthase (iNOS), cyclooxygenase-2 (COX-2), tumor necrosis factor-α (TNF-α), interleukin-1β (IL-1β), monocyte chemoattractant protein-1 (MCP-1), and interleukin-6 (IL-6) were evaluated. We also examined the expression of ninjurin1 (Ninj1) and the adhesion activity of BV2 cells. Finally, we analyzed the activation of the nuclear factor-κB (NF-κB) signaling pathway. Arbutin suppressed LPS-induced production of NO and expression of iNOS and COX-2 in a dose-dependent manner without causing cellular toxicity. Arbutin also significantly reduced generation of proinflammatory cytokines, including IL-1β and TNF-α, and other inflammation-related genes such as MCP-1 and IL-6. Additionally, Arbutin suppressed the adhesion activity of BV2 cells and the expression of an important adhesion molecule, Ninj1, in LPS-stimulated murine BV2 cells. Furthermore, Arbutin inhibited nuclear translocation and the transcriptional activity of NF-κB.
CONCLUSIONS:
Taken together, our results suggest that Arbutin might be useful for treating the inflammatory and deleterious effects of BV2 microglial cells activation in response to LPS stimulation.

Structure Identification
Biosci Biotechnol Biochem. 2014;78(5):874-7.

Extraction of arbutin and its comparative content in branches, leaves, stems, and fruits of Japanese pear Pyrus pyrifolia cv. Kousui.[Pubmed: 25035992]

Arbutin is a tyrosinase inhibitor and is extensively used as a human skin-whitening agent. This study investigated the optimum conditions for extracting Arbutin by ultrasonic homogenization from discarded branches pruned from Japanese pear (Pyrus pyrifolia cv. Kousui) trees. The Arbutin content was measured in the branches and also in the leaves, stems, fruit peel, and fruit flesh.

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Preparing Stock Solutions of Arbutin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.673 mL 18.3648 mL 36.7296 mL 73.4592 mL 91.824 mL
5 mM 0.7346 mL 3.673 mL 7.3459 mL 14.6918 mL 18.3648 mL
10 mM 0.3673 mL 1.8365 mL 3.673 mL 7.3459 mL 9.1824 mL
50 mM 0.0735 mL 0.3673 mL 0.7346 mL 1.4692 mL 1.8365 mL
100 mM 0.0367 mL 0.1836 mL 0.3673 mL 0.7346 mL 0.9182 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Arbutin

Arbutin(β-Arbutin) is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos; inhibits tyrosinase and thus prevents the formation of melanin. IC50 value: Target: tyrosinase

References:
[1]. Arbutin, From Wikipedia

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References on Arbutin

Gastroprotective activities of Turnera diffusa Willd. ex Schult. revisited: Role of arbutin.[Pubmed:22374081]

J Ethnopharmacol. 2012 May 7;141(1):273-81.

ETHNOPHARMACOLOGICAL RELEVANCE: Turnera diffusa Willd. ex Schult. has been used for the treatment of several human disorders including peptic ulcer. OBJECTIVES OF THE STUDY: The current study is an attempt to evaluate the anti-ulcerogenic activities of Arbutin, a major constituent of Turnera diffusa on two ulcer models. The possible involvement of lipid peroxidation, nitric oxide, IL-6, IL-10, TNF-alpha and mucus barrier mechanism has been investigated. MATERIALS AND METHODS: Effects of Arbutin on ulcer index, gastric juice acidity, mucus content and histochemistry, gross and histological gastric lesions, nitric oxide, cytokines levels (IL-6, IL-10 and TNF-alpha), and thiobarbituric acid reactive substances (TBARS), were evaluated in aspirin or ethanol-induced ulcer in vivo. Acute toxicity of Arbutin was also examined in rodent model. MTT assay was used to assess the cytotoxicity of the compound on normal liver cells (WRL-68). RESULTS: Pre-treatment with Arbutin or omeprazole protected the gastric mucosa as seen by reduction in ulcer area and mucosal content, reduced or absence of edema, inflammation and leucocytes infiltration on both models. Arbutin significantly (P<0.05) lowered the elevated TBARS level into gasteric homogenate. Arbutin did not produce significant inhibition of NO. This natural compound has modulated the levels of interleukin-6, interleukin-10 and TNF-alpha. No in vitro or in vivo toxicities for Arbutin were observed. CONCLUSION: Thus it can be concluded that Turnera diffusa possesses anti-ulcer activity, which could be attributed to lipid peroxidation inhibitory, immuno modulatory and anti-oxidant mechanisms of Arbutin but not to the intervention with nitric oxide inflammation pathway.

Extraction of arbutin and its comparative content in branches, leaves, stems, and fruits of Japanese pear Pyrus pyrifolia cv. Kousui.[Pubmed:25035992]

Biosci Biotechnol Biochem. 2014;78(5):874-7.

Arbutin is a tyrosinase inhibitor and is extensively used as a human skin-whitening agent. This study investigated the optimum conditions for extracting Arbutin by ultrasonic homogenization from discarded branches pruned from Japanese pear (Pyrus pyrifolia cv. Kousui) trees. The Arbutin content was measured in the branches and also in the leaves, stems, fruit peel, and fruit flesh.

Alleviation effect of arbutin on oxidative stress generated through tyrosinase reaction with L-tyrosine and L-DOPA.[Pubmed:25297374]

BMC Biochem. 2014 Oct 9;15:23.

BACKGROUND: Hydroxyl radical that has the highest reactivity among reactive oxygen species (ROS) is generated through L-tyrosine-tyrosinase reaction. Thus, the melanogenesis might induce oxidative stress in the skin. Arbutin (p-hydroxyphenyl-beta-D-glucopyranoside), a well-known tyrosinase inhibitor has been widely used for the purpose of skin whitening. The aim of the present study was to examine if Arbutin could suppress the hydroxyl radical generation via tyrosinase reaction with its substrates, L-tyrosine and L-DOPA. RESULTS: The hydroxyl radical, which was determined by an electron spin resonance-spin trapping technique, was generated by the addition of not only L-tyrosine but L-DOPA to tyrosinase in a concentration dependent manner. Arbutin could inhibit the hydroxyl radical generation in the both reactions. CONCLUSION: It is presumed that Arbutin could alleviate oxidative stress derived from the melanogenic pathway in the skin in addition to its function as a whitening agent in cosmetics.

Anti-inflammatory effects of arbutin in lipopolysaccharide-stimulated BV2 microglial cells.[Pubmed:22487852]

Inflamm Res. 2012 Aug;61(8):817-25.

OBJECTIVES AND DESIGN: Arbutin, which is found in the genus Arctostaphylos, is an anti-oxidant and a depigmenting agent. The present study was designed to validate the anti-inflammatory effect of Arbutin. MATERIALS AND METHODS: The anti-inflammatory properties of Arbutin were studied using a lipopolysaccharide (LPS)-stimulated murine BV2 microglial cells model. As inflammatory parameters, the production of nitric oxide (NO), inducible NO synthase (iNOS), cyclooxygenase-2 (COX-2), tumor necrosis factor-alpha (TNF-alpha), interleukin-1beta (IL-1beta), monocyte chemoattractant protein-1 (MCP-1), and interleukin-6 (IL-6) were evaluated. We also examined the expression of ninjurin1 (Ninj1) and the adhesion activity of BV2 cells. Finally, we analyzed the activation of the nuclear factor-kappaB (NF-kappaB) signaling pathway. RESULTS: Arbutin suppressed LPS-induced production of NO and expression of iNOS and COX-2 in a dose-dependent manner without causing cellular toxicity. Arbutin also significantly reduced generation of proinflammatory cytokines, including IL-1beta and TNF-alpha, and other inflammation-related genes such as MCP-1 and IL-6. Additionally, Arbutin suppressed the adhesion activity of BV2 cells and the expression of an important adhesion molecule, Ninj1, in LPS-stimulated murine BV2 cells. Furthermore, Arbutin inhibited nuclear translocation and the transcriptional activity of NF-kappaB. CONCLUSIONS: Taken together, our results suggest that Arbutin might be useful for treating the inflammatory and deleterious effects of BV2 microglial cells activation in response to LPS stimulation.

Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria.[Pubmed:16904805]

Food Chem Toxicol. 2006 Nov;44(11):1940-7.

Arbutin (hydroquinone-beta-D-glucopyranoside) is present in various food plants. Its aglycone, hydroquinone, is mutagenic and carcinogenic. We investigated whether hydroquinone may be released under conditions encountered in the human gastrointestinal tract. Arbutin was stable in artificial gastric juice. Fecal slurries from nine human subjects completely converted Arbutin (2 mM) into hydroquinone. Four of nine representative human intestinal species investigated, namely Eubacterium ramulus, Enterococcus casseliflavus, Bacteroides distasonis, and Bifidobacterium adolescentis, deglycosylated Arbutin at rates of 21.08, 16.62, 8.43 and 3.59 nmol x min(-1) x (mg protein)(-1), respectively. In contrast, homogenates from small intestinal mucosa and cytosolic fractions from colon mucosa deglycosylated Arbutin at substantially lower rates: 0.50 and 0.09 nmol x min(-1) x (mg protein)(-1), respectively. Arbutin, unlike hydroquinone, did not induce gene mutations in Chinese hamster V79 cells in the absence of an activating system. However, in the presence of cytosolic fractions from E. ramulus or B. distasonis, Arbutin was strongly mutagenic. Cytosolic fraction from Escherichia coli, showing no Arbutin glycosidase activity, was not able to activate Arbutin in this model system. The release of the proximate mutagen hydroquinone from Arbutin by intestinal bacteria in the immediate vicinity of the colon mucosa may pose a potential risk.

Description

Arbutin (β-Arbutin) is a competitive inhibitor of tyrosinase in melanocytes, with Kiapp values of 1.42 mM for monophenolase; 0.9 mM for diphenolase. Arbutin is also used as depigmenting agents. Arbutin is a natural polyphenol isolated from the bearberry plant Arctostaphylos uvaursi, possesses with anti-oxidant, anti-inflammatory and anti-tumor properties.

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