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Vicenin 2 (Synonyms: Vicenin II, Violantin)

Catalog No.GC37902

Vicenin 2 es un inhibidor de la enzima convertidora de angiotensina (ACE) (IC50=43.83 μM) de las partes aéreas de Desmodium styracifolium.

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Vicenin 2 Chemical Structure

Cas No.: 23666-13-9

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1mg
71,00 $
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5mg
162,00 $
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10mg
279,00 $
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Sample solution is provided at 25 µL, 10mM.

Description of Vicenin 2

Vicenin 2 is an orally active angiotensin-converting enzyme (ACE) inhibitor with the IC50 value of 43.83 ± 3.01μM[1]. Vicenin 2 has anti-inflammatory and antioxidant properties which make it potential applications in various fields, including skin health and cancer therapy.

In vitro, Vicenin 2 (6.25–400μM) incubated human dermal fibroblast (HDF) cell for 24h. Vicenin 2 treatment on HDF cells enhanced cell proliferation in a dose-dependent up to 50μM, but the higher concentrations inhibited proliferation. Low concentrations of Vicenin 2 (12.5 and 25μM) have significantly induced the cell migration and wound closure, while higher concentrations (50 and 100µM) reduced these effects. In addition, treatment with 100μM of Vicenin 2 on HDF significantly increased the expression of inflammatory cytokines and higher expression for inflammatory mediators (NF-κB, iNOS, and COX-2) and healing growth factors (VEGF and TGF-β) proteins[2]. Vicenin 2 (40μM) incubation for 24 hours can restore the antioxidant defense of human gastric epithelial cells (GES-1) by modulating key signaling pathways (PI3K/AKT and MAPK) and upregulating Nrf2 expression, effectively protecting them from cytotoxicity, oxidative stress, DNA damage, and inflammation induced by Helicobacter pylori. These findings suggest that Vicenin 2 could serve as a potential therapeutic agent for preventing H. pylori-induced gastric carcinogenesis[3]. NCI-H23 cells were treated with 10–100µM of Vicenin 2 for 24h. There was a gradual reduction in the percent surviving cells from 60µM to 100µM. NCI-H23 cells treated with radiation exposure with and without 80µM Vicenin 2 suggested that there was greater reduction in percent cell survival with Vicenin 2 treatment. Vicenin 2 showed a potent radiosensitizing property while also showing chemotherapeutic property against Non-small cell lung cancer (NSCLC) cell line NCI-H23[4].

In vivo,Vicenin 2 (50mg/kg/day) administered orally via oral gavage tube into dextran sulfate sodium-induced colitis mice model for 7 days exerted therapeutic effects by the inhibition of pro-inflammatory mediators (iNOS and COX-2) and suppression of specific inflammatory markers expression[5]. In a study on ovariectomy (OVX)-induced osteoporosis rat models, Vicenin 2 orally administered at doses of 5mg/kg/day or 10mg/kg/day for 12 consecutive weeks significantly improved body mass, uterus index, lipid profiles, and inflammatory markers. Vicenin 2 also reduced bone turnover markers and increased serum calcium levels in the OVX rats. These results suggested that Vicenin 2 could be an excellent candidate to treat and manage bone related disease or disorders[6]. The administration of Vicenin 2 (23.8µg/mouse) into LPS-induced lethal endotoxemia model given twice at 12 and 50 hours post-LPS injection, significantly increased survival rates, reduced endothelial cell protein C receptor shedding, decreased pro-inflammatory cytokine expression, protected vascular barrier integrity, and inhibited leukocyte migration. These findings suggest that Vicenin 2 could serve as a potential therapeutic agent for treating severe vascular inflammatory diseases [7].

References:
[1] Zhang YQ, et al. Bioassay-guided preparative separation of angiotensin-converting enzyme inhibitory C-flavone glycosides from Desmodium styracifolium by recycling complexation high-speed counter-current chromatography. J Pharm Biomed Anal. 2015 Jan;102:276-81.
[2] Tan W S, Arulselvan P, Ng S F, et al. Healing Effect of Vicenin-2 (Vicenin-2) on Human Dermal Fibroblast (HDF) and Development Vicenin-2 Hydrocolloid Film Based on Alginate as Potential Wound Dressing. Biomed Res Int. 2020 Apr 23:2020:4730858.
[3] Zhang Y F, Sun J, Dong Y, et al. Vicenin-2 inhibits the Helicobacterium pylori infection associated gastric carcinogenic events through modulation of PI3K/AKT and Nrf2 signaling in GES-1 cells. J Biochem Mol Toxicol. 2021 Mar;35(3):e22680.
[4] Baruah T J, Sharan R N, Kma L. Vicenin-2: a potential radiosensitizer of non-small cell lung cancer cells. Mol Biol Rep. 2018 Oct;45(5):1219-1225.
[5] Yin Y T, Ye L, Niu Z B, Fang W H.Anti-inflammatory effects of Vicenin-2 on dextran sulfate sodium-induced colitis in mice. Drug Dev Res. 2019 Aug;80(5):546-555.
[6] Zhang Z P, Zhao Q P, Liu T J,et al. Effect of Vicenin-2 on ovariectomy-induced osteoporosis in rats. Biomed Pharmacother. 2020 Sep:129:110474.
[7] Kang H J, Ku S K, Jung B K, BaeJ S. Anti-inflammatory effects of vicenin-2 and scolymoside in vitro and in vivo. Inflamm Res. 2015 Dec;64(12):1005-21.

Protocol of Vicenin 2

Cell experiment [1]:

Cell lines

Non-small cell lung cancer cell line NCI-H23

Preparation Method

NCI-H23 cells were treated with 10–100µM of Vicenin 2 for 24h.

Reaction Conditions

10-100µM; 24h

Applications

Between the doses of 10–50µM, there was no corresponding decrease in cell survival with increase in Vicenin 2 dose. However, from 60µM onwards to 100µM, there was a gradual reduction in the percent surviving cells.The results suggest that Vicenin 2 is cytotoxic to cancer cells.

Animal experiment [2]:

Animal models

female Wistar rats

Preparation Method

Rats underwent either bilateral laparotomy alone or bilateral ovariectomy (OVX group) via midline dorsal incision. After 4 weeks of recovery period all the OVX rats were divided into 3 groups as OVX alone, OVX rats orally administrated (by oral gavage) with 5mg/kg/day of Vicenin 2 or 10mg/kg/day of Vicenin 2 for 12 successive weeks.

Dosage form

5 and 10mg/kg; orally administrated; daily for 12 weeks

Applications

Vicenin 2 mitigated osteoporosis in ovariectomized rats by improving body mass, uterus index, lipid profiles, inflammatory markers, bone turnover markers and amplifying the presence of calcium in the OVX rat serum.

References:
[1]TsBaruah T J, Sharan R N, Kma L. Vicenin-2: a potential radiosensitizer of non-small cell lung cancer cells. Mol Biol Rep. 2018 Oct;45(5):1219-1225.
[2] Zhang Z P, Zhao Q P, Liu T J,et al. Effect of Vicenin-2 on ovariectomy-induced osteoporosis in rats. Biomed Pharmacother. 2020 Sep:129:110474.

Chemical Properties of Vicenin 2

Cas No. 23666-13-9 SDF
Sinónimos Vicenin II, Violantin
Canonical SMILES OC1=C([C@@H]([C@@H]([C@@H](O)[C@@H]2O)O)O[C@@H]2CO)C(O)=C3C(OC(C4=CC=C(O)C=C4)=CC3=O)=C1[C@@H]([C@@H]([C@@H](O)[C@@H]5O)O)O[C@@H]5CO
Formula C27H30O15 M.Wt 594.52
Solubility DMSO : 33.33 mg/mL (56.06 mM; Need ultrasonic); H2O : < 0.1 mg/mL (insoluble) Storage 4°C, protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Vicenin 2

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1 mg 5 mg 10 mg
1 mM 1.682 mL 8.4101 mL 16.8203 mL
5 mM 0.3364 mL 1.682 mL 3.3641 mL
10 mM 0.1682 mL 0.841 mL 1.682 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 7 reference(s) in Google Scholar.)

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