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Mulberroside A

CAS# 102841-42-9

Mulberroside A

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Chemical structure

Mulberroside A

3D structure

Chemical Properties of Mulberroside A

Cas No. 102841-42-9 SDF Download SDF
PubChem ID 6443484 Appearance White-yellowish powder
Formula C26H32O14 M.Wt 568.52
Type of Compound Phenols Storage Desiccate at -20°C
Solubility DMSO : ≥ 40 mg/mL (70.36 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name (2S,3R,4S,5S,6R)-2-[3-hydroxy-4-[(E)-2-[3-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES C1=CC(=C(C=C1OC2C(C(C(C(O2)CO)O)O)O)O)C=CC3=CC(=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O
Standard InChIKey HPSWAEGGWLOOKT-VUNDNAJOSA-N
Standard InChI InChI=1S/C26H32O14/c27-9-17-19(31)21(33)23(35)25(39-17)37-14-4-3-12(16(30)8-14)2-1-11-5-13(29)7-15(6-11)38-26-24(36)22(34)20(32)18(10-28)40-26/h1-8,17-36H,9-10H2/b2-1+/t17-,18-,19-,20-,21+,22+,23-,24-,25-,26-/m1/s1
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 Mulberroside A

The root bark of Morus alba L.

Biological Activity of Mulberroside A

DescriptionMulberroside A, the major active anti-tyrosinase compound in the root bark extract of Morus alba L. (Moraceae), is widely employed as an active ingredient in whitening cosmetics. Mulberroside A has neuroprotective, analgesic, anti-inflammatory, antiapoptotic, uricosuric, nephroprotective, hypoglycemic, and antidiabetic effects.It also can protect mice against ethanol-induced hepatic damage.
TargetsTNF-α | IL Receptor | Caspase | NF-kB | p38MAPK | JNK | P-gp | PKC | OCT | NOS | NO
In vitro

Mulberroside A protects against ischemic impairment in primary culture of rat cortical neurons after oxygen-glucose deprivation followed by reperfusion.[Pubmed: 24687774]

J Neurosci Res. 2014 Jul;92(7):944-54.

Mulberroside A is a natural polyhydroxylated stilbene compound present at relatively high abundance in the roots and twigs of Morus alba L. It is known for its nephroprotective, hypoglycemic, and antidiabetic effects. Because its metabolite, oxyresveratrol, possessed purported anti-inflammatory and neuroprotective effects, we proposed that Mulberroside A may elicit neuroprotective effects that can be used in the treatment of brain ischemic injury.
METHODS AND RESULTS:
Therefore, we decided to investigate the pharmacological properties of Mulberroside A in primary culture of rat cortical neurons after oxygen-glucose deprivation followed by reperfusion (OGD/R), evaluating its ability to counteract the hypoxia-ischemia impairment. The results showed that Mulberroside A elicited neuroprotective effects comparable to nimodipine. The mechanistic studies showed that Mulberroside A decreased the expressions of tumor necrosis factor-α (TNF-α), interleukin (IL)-1β, and IL-6 and inhibited the activation of NALP3, caspase-1, and nuclear factor-κB and the phosphorylation of extracellular signal-regulated protein kinases, the c-Jun N-terminal kinase, and p38, exhibiting anti-inflammatory antiapoptotic effects. Our results also further demonstrate that the proinflammatory cytokines of IL-1β, IL-6, and TNF-α are promising targets for treatment of cerebral ischemic injury.
CONCLUSIONS:
Although further investigation is required for its development, all of these findings led us to speculate that Mulberroside A is a candidate for the treatment of ischemic stroke, which would act as a multifactorial neuroprotectant.

In vivo

Mulberroside a possesses potent uricosuric and nephroprotective effects in hyperuricemic mice.[Pubmed: 21154198]

Planta Med. 2011 May;77(8):786-94.

Mulberroside A is a major stilbene glycoside of MORUS ALBA L. (Moraceae), which is effectively used for the treatment of hyperuricemia and gout in traditional Chinese medicine. We examined whether Mulberroside A had effects on renal urate underexcretion and dysfunction in oxonate-induced hyperuricemic mice and investigated the potential uricosuric and nephroprotective mechanisms involved.
METHODS AND RESULTS:
Mulberroside A at 10, 20, and 40 mg/kg decreased serum uric acid levels and increased urinary urate excretion and fractional excretion of uric acid in hyperuricemic mice. Simultaneously, it reduced serum levels of creatinine and urea nitrogen (10-40 mg/kg), urinary N-acetyl- β-D-glucosaminidase activity (10-40 mg/kg), β₂-microglobulin (10-40 mg/kg) and albumin (20-40 mg/kg), and increased creatinine clearance (10-40 mg/kg) in hyperuricemic mice. Furthermore, Mulberroside A downregulated mRNA and protein levels of renal glucose transporter 9 (mGLUT9) and urate transporter 1 (mURAT1), and upregulated mRNA and protein levels of renal organic anion transporter 1 (mOAT1) and organic cation and carnitine transporters (mOCT1, mOCT2, mOCTN1, and mOCTN2) in hyperuricemic mice. This is the first study demonstrating that Mulberroside A exhibits uricosuric and nephroprotective effects mediated in part by cooperative attenuation of the expression alterations of renal organic ion transporters in hyperuricemic mice.
CONCLUSIONS:
These data suggest that Mulberroside A may be a new drug candidate for the treatment of hyperuricemia with renal dysfunction.

Protective function of cis-mulberroside A and oxyresveratrol from Ramulus mori against ethanol-induced hepatic damage.[Pubmed: 21791383 ]

Environ Toxicol Pharmacol. 2008 Nov;26(3):325-30.

The aim of the study was to investigate the protective effects of oxyresveratrol and cis-Mulberroside A isolated from Ramulus mori on the liver of mice intoxicated with ethanol.
METHODS AND RESULTS:
Animals were pretreated with different doses (30 and 60mg/kg of body weight) of oxyresveratrol and cis-Mulberroside A prior to the ethanol (9g/kg of body weight) orally for 7 days. Ethanol treatment induced the decrease of reduced glutathione level and antioxidant enzymes activities, the elevation of the lipid peroxidation and cytochrome P450 2E1 activity accompanied with the increase of iron concentration and mitochondrial permeability transition. Pretreatment with oxyresveratrol and cis-Mulberroside A restored the changes in the above parameters up to the basal level. The protective effects of the two active compounds were further supported by attenuation of the degree of tissue damage and the regulation of the expression of TNF-α.
CONCLUSIONS:
It could be concluded that oxyresveratrol and cis-Mulberroside A from R. mori could protect mice against ethanol-induced hepatic damage.

Protocol of Mulberroside A

Cell Research

Down-regulation of P-gp expression and function after Mulberroside A treatment: potential role of protein kinase C and NF-kappa B.[Pubmed: 24530447]

Chem Biol Interact. 2014 Apr 25;213:44-50.

P-Glycoprotein (P-gp) plays a major role in drug-drug and herb-drug interactions. Mulberroside A (Mul A) is one of the main bioactive constituents of Sangbaipi, the dried root-bark of Morus alba L. (white mulberry), which is officially listed in the Chinese Pharmacopoeia.
METHODS AND RESULTS:
In the present study, we investigated the effect of Mul A treatment on mRNA expression and protein expression of P-gp in the Caco-2 cells by real-time qPCR and Western blot analysis. The effect of Mul A treatment on the function of P-gp in vitro and in vivo was assessed by Rho123 transport assay and a pharmacokinetic study. The potential roles of protein kinase C (PKC) and nuclear factor kappa B (NF-κB) in the expression regulation of P-gp after Mul A treatment were also investigated. The results revealed that Mul A treatment significantly decreased the mRNA and protein expression of P-gp in Caco-2 cells after treatment with Mul A (5-20 μM). Furthermore, Mul A treatment displayed apparently inhibitory effect on the function of P-gp both in vitro and in vivo. In addition, activation of PKC activity and NF-κB nuclear translocation were observed in the presence of Mul A, which suggested that PKC and NF-κB might play crucial roles in Mul A-induced suppression of P-gp.
CONCLUSIONS:
Our study demonstrated that Mul A treatment could down-regulate P-gp expression and function accompanied by the activation of PKC and NF-κB, and this should be taken into consideration in potential herb-drug interactions when Mul A or M. alba are co-administered with other drugs transported by P-gp.

Animal Research

Anti-inflammatory and analgesic properties of cis-mulberroside A from Ramulus mori.[Pubmed: 19755140 ]

Inhibitory effect of mulberroside A and its derivatives on melanogenesis induced by ultraviolet B irradiation.[Pubmed: 21946069]

Food Chem Toxicol. 2011 Dec;49(12):3038-45.

Mulberroside A was isolated from the ethanol extract of Morus alba roots. The enzymatic hydrolysis of Mulberroside A with Pectinex produced oxyresveratrol and oxyresveratrol-3-O-glucoside. We tested oxyresveratrol, oxyresveratrol-3-O-glucoside, and Mulberroside A to determine whether they could inhibit ultraviolet B (UVB) irradiation-induced melanogenesis in brown guinea pig skin.
METHODS AND RESULTS:
Topical application of Mulberroside A, oxyresveratrol, and oxyresveratrol-3-O-glucoside reduced the pigmentation in guinea pig skin. These compounds suppressed the expression of melanogenic enzymes tyrosinase, tyrosinase-related protein-1, and microphthalmia transcription factor. The anti-melanogenesis effect was highest with oxyresveratrol, intermediate with oxyresveratrol-3-O-glucoside, and lowest with Mulberroside A. Mulberroside A is a glycosylated stilbene of oxyresveratrol; thus, the deglycosylation of Mulberroside A resulted in enhanced inhibition of melanogenesis. Histological analysis with Fontana-Masson staining confirmed that these compounds significantly reduced the melanin content in the epidermis of UVB-irradiated guinea pig skin compared to the vehicle control.
CONCLUSIONS:
Thus, these compounds effectively reduced pigmentation and may be suitable cosmetic agents for skin whitening.

Fitoterapia. 2010 Apr;81(3):214-8.

This study examined the analgesic and anti-inflammatory actions of cis-Mulberroside A isolated from Ramulus mori in several models of inflammatory pain in mice.
METHODS AND RESULTS:
Cis-Mulberroside A (25 and 50mg/kg) given by p.o. route 30 min before challenge produced a dose-dependent inhibition of the acetic acid-induced pain and Evans blue leakage in mice. In addition, this compound exhibited significant systemic anti-inflammatory activity in carrageenan-induced mouse paw edema in a concentration-related manner (33.1-68.5% inhibition), and similar results were achieved in formalin test. Suppressive effects of cis-Mulberroside A on the production of NO and expression of inducible nitric oxide synthase (iNOS) in lipopolysaccharide (LPS)-stimulated macrophages were also assessed. Collectively, cis-Mulberroside A showed high analgesic and anti-inflammatory activities.
CONCLUSIONS:
The above results will be the supporting evidence for the potential anti-rheumatoid activity of R.mori in Chinese traditional medicine.

Mulberroside A Dilution Calculator

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Mulberroside A Molarity Calculator

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Preparing Stock Solutions of Mulberroside A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.759 mL 8.7948 mL 17.5895 mL 35.1791 mL 43.9738 mL
5 mM 0.3518 mL 1.759 mL 3.5179 mL 7.0358 mL 8.7948 mL
10 mM 0.1759 mL 0.8795 mL 1.759 mL 3.5179 mL 4.3974 mL
50 mM 0.0352 mL 0.1759 mL 0.3518 mL 0.7036 mL 0.8795 mL
100 mM 0.0176 mL 0.0879 mL 0.1759 mL 0.3518 mL 0.4397 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 Mulberroside A

Mulberroside A, the major active anti-tyrosinase compound in the root bark extract of Morus alba L. (Moraceae), is widely employed as an active ingredient in whitening cosmetics. IC50 value: 1.29 μmol/L (inhibition of the monophenolase activity); KI value: 0.385 μmol/L (the inhibition constant of the effectors on tyrosinase); KIS value: 0.177 μmol/L (the inhibition constant of the enzyme-substrate complex) [3] Target: In vitro: Mulberroside A decreased the expressions of tumor necrosis factor-α (TNF-α), interleukin (IL)-1β, and IL-6 and inhibited the activation of NALP3, caspase-1, and nuclear factor-κB and the phosphorylation of extracellular signal-regulated protein kinases, the c-Jun N-terminal kinase, and p38 exhibiting anti-inflammatory antiapoptotic effects [1]. Mulberroside A treatment significantly decreased the mRNA and protein expression of P-gp in Caco-2 cells after treatment with Mulberroside A (5–20 μM). PKC and NF-κB might play crucial roles in Mulberroside A-induced suppression of P-gp [2]. In vivo:

References:
[1]. Cai-Ping Wang, et al. Mulberroside a protects against ischemic impairment in primary culture of rat cortical neurons after oxygen–glucose deprivation followed by reperfusion. Journal of Neuroscience Research Volume 92, Issue 7, pages 944–954, July 2014 [2]. Yuhua Li, et al. Down-regulation of P-gp expression and function after Mulberroside A treatment: Potential role of protein kinase C and NF-kappa B. Chemico-Biological Interactions Volume 213, 25 April 2014, Pages 44–50 [3]. Shu Wang, et al. An efficient preparation of mulberroside a from the branch bark of mulberry and its effect on the inhibition of tyrosinase activity. PloS one 2014, 9 (10): e109396

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References on Mulberroside A

Inhibitory effect of mulberroside A and its derivatives on melanogenesis induced by ultraviolet B irradiation.[Pubmed:21946069]

Food Chem Toxicol. 2011 Dec;49(12):3038-45.

Mulberroside A was isolated from the ethanol extract of Morus alba roots. The enzymatic hydrolysis of Mulberroside A with Pectinex produced oxyresveratrol and oxyresveratrol-3-O-glucoside. We tested oxyresveratrol, oxyresveratrol-3-O-glucoside, and Mulberroside A to determine whether they could inhibit ultraviolet B (UVB) irradiation-induced melanogenesis in brown guinea pig skin. Topical application of Mulberroside A, oxyresveratrol, and oxyresveratrol-3-O-glucoside reduced the pigmentation in guinea pig skin. These compounds suppressed the expression of melanogenic enzymes tyrosinase, tyrosinase-related protein-1, and microphthalmia transcription factor. The anti-melanogenesis effect was highest with oxyresveratrol, intermediate with oxyresveratrol-3-O-glucoside, and lowest with Mulberroside A. Mulberroside A is a glycosylated stilbene of oxyresveratrol; thus, the deglycosylation of Mulberroside A resulted in enhanced inhibition of melanogenesis. Histological analysis with Fontana-Masson staining confirmed that these compounds significantly reduced the melanin content in the epidermis of UVB-irradiated guinea pig skin compared to the vehicle control. Thus, these compounds effectively reduced pigmentation and may be suitable cosmetic agents for skin whitening.

Mulberroside a possesses potent uricosuric and nephroprotective effects in hyperuricemic mice.[Pubmed:21154198]

Planta Med. 2011 May;77(8):786-94.

Mulberroside A is a major stilbene glycoside of MORUS ALBA L. (Moraceae), which is effectively used for the treatment of hyperuricemia and gout in traditional Chinese medicine. We examined whether Mulberroside A had effects on renal urate underexcretion and dysfunction in oxonate-induced hyperuricemic mice and investigated the potential uricosuric and nephroprotective mechanisms involved. Mulberroside A at 10, 20, and 40 mg/kg decreased serum uric acid levels and increased urinary urate excretion and fractional excretion of uric acid in hyperuricemic mice. Simultaneously, it reduced serum levels of creatinine and urea nitrogen (10-40 mg/kg), urinary N-acetyl- beta-D-glucosaminidase activity (10-40 mg/kg), beta(2)-microglobulin (10-40 mg/kg) and albumin (20-40 mg/kg), and increased creatinine clearance (10-40 mg/kg) in hyperuricemic mice. Furthermore, Mulberroside A downregulated mRNA and protein levels of renal glucose transporter 9 (mGLUT9) and urate transporter 1 (mURAT1), and upregulated mRNA and protein levels of renal organic anion transporter 1 (mOAT1) and organic cation and carnitine transporters (mOCT1, mOCT2, mOCTN1, and mOCTN2) in hyperuricemic mice. This is the first study demonstrating that Mulberroside A exhibits uricosuric and nephroprotective effects mediated in part by cooperative attenuation of the expression alterations of renal organic ion transporters in hyperuricemic mice. These data suggest that Mulberroside A may be a new drug candidate for the treatment of hyperuricemia with renal dysfunction.

Down-regulation of P-gp expression and function after Mulberroside A treatment: potential role of protein kinase C and NF-kappa B.[Pubmed:24530447]

Chem Biol Interact. 2014 Apr 25;213:44-50.

P-Glycoprotein (P-gp) plays a major role in drug-drug and herb-drug interactions. Mulberroside A (Mul A) is one of the main bioactive constituents of Sangbaipi, the dried root-bark of Morus alba L. (white mulberry), which is officially listed in the Chinese Pharmacopoeia. In the present study, we investigated the effect of Mul A treatment on mRNA expression and protein expression of P-gp in the Caco-2 cells by real-time qPCR and Western blot analysis. The effect of Mul A treatment on the function of P-gp in vitro and in vivo was assessed by Rho123 transport assay and a pharmacokinetic study. The potential roles of protein kinase C (PKC) and nuclear factor kappa B (NF-kappaB) in the expression regulation of P-gp after Mul A treatment were also investigated. The results revealed that Mul A treatment significantly decreased the mRNA and protein expression of P-gp in Caco-2 cells after treatment with Mul A (5-20 muM). Furthermore, Mul A treatment displayed apparently inhibitory effect on the function of P-gp both in vitro and in vivo. In addition, activation of PKC activity and NF-kappaB nuclear translocation were observed in the presence of Mul A, which suggested that PKC and NF-kappaB might play crucial roles in Mul A-induced suppression of P-gp. Our study demonstrated that Mul A treatment could down-regulate P-gp expression and function accompanied by the activation of PKC and NF-kappaB, and this should be taken into consideration in potential herb-drug interactions when Mul A or M. alba are co-administered with other drugs transported by P-gp.

Mulberroside A protects against ischemic impairment in primary culture of rat cortical neurons after oxygen-glucose deprivation followed by reperfusion.[Pubmed:24687774]

J Neurosci Res. 2014 Jul;92(7):944-54.

Mulberroside A is a natural polyhydroxylated stilbene compound present at relatively high abundance in the roots and twigs of Morus alba L. It is known for its nephroprotective, hypoglycemic, and antidiabetic effects. Because its metabolite, oxyresveratrol, possessed purported anti-inflammatory and neuroprotective effects, we proposed that Mulberroside A may elicit neuroprotective effects that can be used in the treatment of brain ischemic injury. Therefore, we decided to investigate the pharmacological properties of Mulberroside A in primary culture of rat cortical neurons after oxygen-glucose deprivation followed by reperfusion (OGD/R), evaluating its ability to counteract the hypoxia-ischemia impairment. The results showed that Mulberroside A elicited neuroprotective effects comparable to nimodipine. The mechanistic studies showed that Mulberroside A decreased the expressions of tumor necrosis factor-alpha (TNF-alpha), interleukin (IL)-1beta, and IL-6 and inhibited the activation of NALP3, caspase-1, and nuclear factor-kappaB and the phosphorylation of extracellular signal-regulated protein kinases, the c-Jun N-terminal kinase, and p38, exhibiting anti-inflammatory antiapoptotic effects. Our results also further demonstrate that the proinflammatory cytokines of IL-1beta, IL-6, and TNF-alpha are promising targets for treatment of cerebral ischemic injury. Although further investigation is required for its development, all of these findings led us to speculate that Mulberroside A is a candidate for the treatment of ischemic stroke, which would act as a multifactorial neuroprotectant.

Anti-inflammatory and analgesic properties of cis-mulberroside A from Ramulus mori.[Pubmed:19755140]

Fitoterapia. 2010 Apr;81(3):214-8.

This study examined the analgesic and anti-inflammatory actions of cis-Mulberroside A isolated from Ramulus mori in several models of inflammatory pain in mice. Cis-Mulberroside A (25 and 50mg/kg) given by p.o. route 30 min before challenge produced a dose-dependent inhibition of the acetic acid-induced pain and Evans blue leakage in mice. In addition, this compound exhibited significant systemic anti-inflammatory activity in carrageenan-induced mouse paw edema in a concentration-related manner (33.1-68.5% inhibition), and similar results were achieved in formalin test. Suppressive effects of cis-Mulberroside A on the production of NO and expression of inducible nitric oxide synthase (iNOS) in lipopolysaccharide (LPS)-stimulated macrophages were also assessed. Collectively, cis-Mulberroside A showed high analgesic and anti-inflammatory activities. The above results will be the supporting evidence for the potential anti-rheumatoid activity of R.mori in Chinese traditional medicine.

Protective function of cis-mulberroside A and oxyresveratrol from Ramulus mori against ethanol-induced hepatic damage.[Pubmed:21791383]

Environ Toxicol Pharmacol. 2008 Nov;26(3):325-30.

The aim of the study was to investigate the protective effects of oxyresveratrol and cis-Mulberroside A isolated from Ramulus mori on the liver of mice intoxicated with ethanol. Animals were pretreated with different doses (30 and 60mg/kg of body weight) of oxyresveratrol and cis-Mulberroside A prior to the ethanol (9g/kg of body weight) orally for 7 days. Ethanol treatment induced the decrease of reduced glutathione level and antioxidant enzymes activities, the elevation of the lipid peroxidation and cytochrome P450 2E1 activity accompanied with the increase of iron concentration and mitochondrial permeability transition. Pretreatment with oxyresveratrol and cis-Mulberroside A restored the changes in the above parameters up to the basal level. The protective effects of the two active compounds were further supported by attenuation of the degree of tissue damage and the regulation of the expression of TNF-alpha. It could be concluded that oxyresveratrol and cis-Mulberroside A from R. mori could protect mice against ethanol-induced hepatic damage.

Description

Mulberroside A is one of the main bioactive constituent in mulberry (Morus alba L.). Mulberroside A decreases the expressions of TNF-α, IL-1β, and IL-6 and inhibits the activation of NALP3, caspase-1, and NF-κB and the phosphorylation of ERK, JNK, and p38, exhibiting anti-inflammatory antiapoptotic effects. Mulberroside A shows inhibitory activity against mushroom tyrosinase with an IC50 of 53.6 μM.

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