| Size | Price | Stock | Qty |
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| 25mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| Other Sizes |
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Purity: ≥98%
| Targets |
Natural product; anti-osteoporotic, cytoprotective, and hepatoprotective effects
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| ln Vitro |
In the course of screening for the melanogenesis inhibitors, sweroside was isolated from Lonicera japonica. Its chemical structure was determined on the basis of spectroscopic analysis, including mass spectroscopy and nuclear magnetic resonance analysis. Sweroside inhibited potent melanogenesis in melan-a cells at 300μM without cytotoxicity. Also, sweroside decreased tyrosinase, tyrosinase-related protein-1 (TRP-1) and TRP-2 protein production in melan a cells. To identify the signaling pathway of sweroside, the ability of sweroside to influence Akt and extracellular signal-regulated protein kinase (ERK) activation was investigated. Sweroside induced Akt and ERK in a dose-dependent manner. In addition, the specific inhibition of the Akt and ERK signaling pathways were studied by specific inhibitor LY294002 and U0126, respectively and it was causing the increased melanin synthesis.[2]
Wound healing properties of Gentian (Gentiana lutea ssp. symphyandra) extract and its main constituents, gentiopicroside, sweroside and swertiamarine (compounds 1-3, respectively) were evaluated by comparison with dexpanthenol on cultured chicken embryonic fibroblasts. The extract was also analyzed by HPLC to quantify its constituents. Chicken embryonic fibroblasts from fertilized eggs were incubated with the plant extract and its constituents, compounds 1-3. Using microscopy, mitotic ability, morphological changes and collagen production in the cultured fibroblasts were evaluated as parameters. Wound healing activity of Gentian seems to be mainly due to the increase in the stimulation of collagen production and the mitotic activity by compounds 2 and 3, respectively (p < 0.005 in all cases). All three compounds also exhibited cytoprotective effects, which may cause a synergism in terms of wound healing activity of Gentian. The findings demonstrated the wound healing activity of Gentian, which has previously been based only on ethnomedical data[1]. |
| ln Vivo |
Sweroside presented inhibition of the body pigmentation and tyrosinase activity in zebrafish in vivo model. These results suggest that sweroside isolated from L. japonica may be an effective skin-whitening agent through the regulates the expression of MAP kinase and melanogenic enzymes[2].
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| Enzyme Assay |
Compound treatment and phenotype-based evaluation[2]
Synchronized embryos were collected and arrayed by pipette (7–9 embryos per well in 24 well plates containing 1 ml of embryo medium). Test compounds were dissolved in 0.1% DMSO, and then added to the embryo medium from 9 to 72 h post-fertilization (h.p.f) (63 h exposure). The effects on the pigmentation of zebrafish were observed under the stereomicroscope. Occasional stirring as well as replacement of the medium was performed daily to ensure the even distribution of the compounds. In all experiments, 0.1 mM PTU was used to generate transparent zebrafish without interfering in the developmental process, and considered as a standard positive control. Phenotype-based evaluations of body pigmentation were dechorionated by forceps, anesthetized in tricaine methanesulfonate solution, mounted in 3% methylcellulose on a 35 mm dish (35 × 10 mm), and photographed under the stereomicroscope MZ16. |
| Cell Assay |
Cell culture[2]
Melan-a melanocytes are a highly pigmented, immortalized normal murine melanocyte cell line derived from C57BL/6 mice. The melan-a cell used in this study was obtained from Dr. Dorothy Bennett. Cells were cultured at 37 °C in an atmosphere of 95% air, 5% CO2 in RPMI 1640 medium supplemented to a final concentration with 10% heat-inactivated fetal bovine serum, 1% penicillin/streptomycin and 200 nM 12-o-tetradecanoylphorbol-13-acetate. Cell viability was determinate by CCK-8 cell counting kit-8. Monolayers of confluent melanocytes were harvested with a mixture of 0.05% trypsin and 0.53 mM EDTA. Measurement of melanin content[2] Melan-a cells were treated with compounds for 72 h, and then the cells were dissolved in 1 N NaOH at 60 °C for 30 min. Then, the lysates were measured at 450 nm using a spectrophotometer. The data were normalized to the protein content of the cell lysates. The cell lysates were subsequently processed for the determination of the protein concentration using a BCA protein assay kit. Western blot analysis[2] Melan-a cells were washed once with 10 mM phosphate buffer (pH 7.4) containing 150 mM NaCl (PBS) and lysed in PBS containing 0.1% SDS and 10 mM-mercaptoethanol. The lysate was applied to 10% SDS–polyacrylamide gels. The protein bands in the gels were blotted onto nitrocellulose membranes using a mini-Protean system according to the manufacturer’s instructions. The membranes were then washed once with 10 mM Tris-buffered saline (TBS, pH 7.2) containing 0.1% Tween-20 (TBS-T), and then blocked for 1 h in TBS-T containing 5% skim milk. The primary antibodies were diluted at 1:1000, unless otherwise noted, and were incubated at 4 °C overnight. The membranes were washed three times for 10 min each with TBS-T buffer. The membranes were incubated with HRP-coupled secondary antibodies diluted at 1:3000 in TBS-T buffer for 1 h at room temperature, washed three times for 3 min each in TBS-T buffer, and then developed using the ECL detection kit. |
| Animal Protocol |
Tyrosinase activity and melanin contents in zebrafish[2]
Tyrosinase activity was spectrometrically determined. Briefly, about 100 zebrafish embryos were treated with sweroside from 9 to 48 h.p.f. and sonicated in Pro-Prep protein extraction solution. The lysate was clarified by centrifuging at 10,000g for 5 min. After quantification, 250 μg of total protein was added, followed by 100 μl of 5 mM L-3,4-dihydroxyphenylalanine (L-DOPA). Control well contained 100 μl of lysis buffer and 100 μl of 5 mM L-DOPA. After incubation for 60 min at 37 °C, absorbance was measured at 475 nm using the microplate leader. For the determination of melanin content, briefly, about 100 zebrafish embryos were treated with sweroside from 9 to 35 h.p.f, and sonicated in Pro-Prep protein extraction solution. After the centrifugation, the pellet was dissolved in 500 μl of 1 N NaOH at 100 °C for 10 min. The mixture was then vigorously vortexed to solubilize the melanin pigment. Optical density of the supernatant was measured at 490 nm |
| References |
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| Additional Infomation |
Sweroside is a glycoside.
Sweroside has been reported in Gentiana macrophylla, Gentiana algida, and other organisms with data available. See also: Lonicera japonica flower (part of); Menyanthes trifoliata leaf (part of); Centaurium erythraea whole (part of). |
| Molecular Formula |
C16H22O9
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|---|---|
| Molecular Weight |
358.3405
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| Exact Mass |
358.126
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| Elemental Analysis |
C, 53.63; H, 6.19; O, 40.18
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| CAS # |
14215-86-2
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| PubChem CID |
161036
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
630.3±55.0 °C at 760 mmHg
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| Melting Point |
100 °C
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| Flash Point |
231.8±25.0 °C
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| Vapour Pressure |
0.0±4.2 mmHg at 25°C
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| Index of Refraction |
1.602
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| Source |
Gentiana macrophylla; Gentiana algida; Lonicera japonica
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| LogP |
-2.81
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
25
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| Complexity |
548
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| Defined Atom Stereocenter Count |
8
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| SMILES |
O([C@@]1([H])[C@]([H])(C([H])=C([H])[H])[C@@]2([H])C(C(=O)OC([H])([H])C2([H])[H])=C([H])O1)[C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(C([H])([H])O[H])O1)O[H])O[H])O[H]
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| InChi Key |
VSJGJMKGNMDJCI-ZASXJUAOSA-N
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| InChi Code |
InChI=1S/C16H22O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2,6-8,10-13,15-20H,1,3-5H2/t7-,8+,10-,11-,12+,13-,15+,16+/m1/s1
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| Chemical Name |
(3S,4R,4aS)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-8-one
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| Synonyms |
(−) Sweroside; (−)-Sweroside; 1,9-trans-9,5-cis-Sweroside
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~279.06 mM)
H2O : ~50 mg/mL (~139.53 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (6.98 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (6.98 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (6.98 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (279.06 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7906 mL | 13.9532 mL | 27.9065 mL | |
| 5 mM | 0.5581 mL | 2.7906 mL | 5.5813 mL | |
| 10 mM | 0.2791 mL | 1.3953 mL | 2.7906 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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