(+/-)-Vestitol

CAS# 56701-24-7

(+/-)-Vestitol

2D Structure

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(+/-)-Vestitol

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Chemical Properties of (+/-)-Vestitol

Cas No. 56701-24-7 SDF Download SDF
PubChem ID 92503 Appearance Powder
Formula C16H16O4 M.Wt 272.29
Type of Compound Flavonoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
SMILES COC1=CC(=C(C=C1)C2CC3=C(C=C(C=C3)O)OC2)O
Standard InChIKey XRVFNNUXNVWYTI-UHFFFAOYSA-N
Standard InChI InChI=1S/C16H16O4/c1-19-13-4-5-14(15(18)8-13)11-6-10-2-3-12(17)7-16(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3
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 (+/-)-Vestitol

The herb of Lotus corniculatus L.

Biological Activity of (+/-)-Vestitol

DescriptionVestitol has antioxidation, anti-inflammatory and antimicrobial activities, it can strongly act in a low dose and concentration and have a promising potential to be applied in the pharmaceutical and food industries. Vestitol inhibits neutrophils migration in the inflammatory process.
TargetsCXCR | NOS | Antifection | Immunology & Inflammation related
In vitro

Anti-inflammatory and antimicrobial evaluation of neovestitol and vestitol isolated from Brazilian red propolis.[Pubmed: 23607483 ]

J Agric Food Chem. 2013 May 15;61(19):4546-50.

The objective of this study was to evaluate anti-inflammatory and antimicrobial activities of neovestitol and vestitol((+/-)-Vestitol) isolated from Brazilian red propolis (BRP).
METHODS AND RESULTS:
BRP ethanolic extract (EEP), neovestitol, and vestitol((+/-)-Vestitol) were evaluated by anti-inflammatory properties using a neutrophil migration assay. The antimicrobial activity was evaluated by minimal inhibitory and bactericidal concentrations (MIC and MBC) against Streptococcus mutans , Streptococcus sobrinus , Staphylococcus aureus , and Actinomyces naeslundii . Neovestitol, vestitol((+/-)-Vestitol), and EEP inhibited neutrophil migration at a dose of 10 mg/kg. Regarding antimicrobial activity, neovestitol showed MICs ranging from <6.25 to 25-50 μg/mL and MBCs ranging from 25-50 to 50-100 μg/mL, while vestitol((+/-)-Vestitol) showed MICs ranging from 25-50 to 50-100 μg/mL and MBCs ranging from 25-50 to 50-100 μg/mL.
CONCLUSIONS:
Both isoflavonoids neovestitol and vestitol((+/-)-Vestitol) are consistent bioactive compounds displaying anti-inflammatory and antimicrobial activities that can strongly act in a low dose and concentration and have a promising potential to be applied in the pharmaceutical and food industries.

Antioxidation Activities of Natural Components from Dalbergia odorifera T.Chen[Reference: WebLink]

Fine Chemicals, 2004, 21(7):525-8.

The antioxidation activities of natural components extracted from Dalbergia odorifera T.Chen on lard and ascidian oil were investigated by OSI.
METHODS AND RESULTS:
Dalbergia odorifera T.Chen was extracted with 95% ethanol,and the extract was then extracted by petroleum ether,CHCl_3,EtOAc and BuOH successively.The residue of EtOAc had very good antioxidation activity.Eight components were isolated from it,i.e.,2,4-dihydroxy-5-methoxybenzophenone(Ⅰ),2′,3′,7-trihydroxy-4-methoxyisoflavone(Ⅱ),3′-methoxydaidzin(Ⅲ),4′,5,7-trihydroxy-3-methoxyflavone(Ⅳ),vestitol((+/-)-Vestitol,Ⅴ),medicarpin(Ⅵ),2-propenyl hexanoate(Ⅶ) and ethyl hexadecanoate(Ⅷ).
CONCLUSIONS:
The results showed that components Ⅰ,Ⅲ,Ⅴ and Ⅵ had antioxidation activity and components Ⅱ and Ⅳ had strong antioxidant activities both on lard and ascidian oil at 0.02% and 0.04% levels.

In vivo

Vestitol Isolated from Brazilian Red Propolis Inhibits Neutrophils Migration in the Inflammatory Process: Elucidation of the Mechanism of Action.[Pubmed: 26938776 ]

J Nat Prod. 2016 Apr 22;79(4):954-60.

Vestitol((+/-)-Vestitol) is an isoflavonoid isolated from Brazilian red propolis with potential anti-inflammatory activity. This study investigated the mechanism of action of vestitol on the modulation of neutrophil migration in the inflammatory process.
METHODS AND RESULTS:
Pre-treatment with vestitol((+/-)-Vestitol) at 1, 3, or 10 mg/kg reduced LPS- or mBSA-induced neutrophil migration and the release of CXCL1/KC and CXCL2/MIP-2 in vivo. Likewise, pre-treatment with vestitol at 1, 3, or 10 μM reduced the levels of CXCL1/KC and CXCL2/MIP-2 in macrophage supernatants in vitro. Moreover, the administration of vestitol((+/-)-Vestitol) (10 mg/kg) reduced leukocyte rolling and adherence in the mesenteric microcirculation of mice. The pre-treatment with vestitol((+/-)-Vestitol) (10 mg/kg) in iNOS(-/-) mice did not block its activity concerning neutrophil migration. With regard to the activity of vestitol on neutrophils isolated from the bone marrow of mice, there was a reduction on the chemotaxis of CXCL2/MIP-2 or LTB4-induced neutrophils and on calcium influx after pre-treatment with the compound at 3 or 10 μM. There was no change in CXCR2 expression by neutrophils treated with vestitol((+/-)-Vestitol) at 10 μM.
CONCLUSIONS:
These findings demonstrate that vestitol((+/-)-Vestitol) is a promising novel anti-inflammatory agent.

(+/-)-Vestitol Dilution Calculator

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(+/-)-Vestitol Molarity Calculator

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Preparing Stock Solutions of (+/-)-Vestitol

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.6726 mL 18.3628 mL 36.7255 mL 73.4511 mL 91.8139 mL
5 mM 0.7345 mL 3.6726 mL 7.3451 mL 14.6902 mL 18.3628 mL
10 mM 0.3673 mL 1.8363 mL 3.6726 mL 7.3451 mL 9.1814 mL
50 mM 0.0735 mL 0.3673 mL 0.7345 mL 1.469 mL 1.8363 mL
100 mM 0.0367 mL 0.1836 mL 0.3673 mL 0.7345 mL 0.9181 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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References on (+/-)-Vestitol

Anti-inflammatory and antimicrobial evaluation of neovestitol and vestitol isolated from Brazilian red propolis.[Pubmed:23607483]

J Agric Food Chem. 2013 May 15;61(19):4546-50.

The objective of this study was to evaluate anti-inflammatory and antimicrobial activities of neovestitol and vestitol isolated from Brazilian red propolis (BRP). BRP ethanolic extract (EEP), neovestitol, and vestitol were evaluated by anti-inflammatory properties using a neutrophil migration assay. The antimicrobial activity was evaluated by minimal inhibitory and bactericidal concentrations (MIC and MBC) against Streptococcus mutans , Streptococcus sobrinus , Staphylococcus aureus , and Actinomyces naeslundii . Neovestitol, vestitol, and EEP inhibited neutrophil migration at a dose of 10 mg/kg. Regarding antimicrobial activity, neovestitol showed MICs ranging from <6.25 to 25-50 mug/mL and MBCs ranging from 25-50 to 50-100 mug/mL, while vestitol showed MICs ranging from 25-50 to 50-100 mug/mL and MBCs ranging from 25-50 to 50-100 mug/mL. Both isoflavonoids neovestitol and vestitol are consistent bioactive compounds displaying anti-inflammatory and antimicrobial activities that can strongly act in a low dose and concentration and have a promising potential to be applied in the pharmaceutical and food industries.

Vestitol Isolated from Brazilian Red Propolis Inhibits Neutrophils Migration in the Inflammatory Process: Elucidation of the Mechanism of Action.[Pubmed:26938776]

J Nat Prod. 2016 Apr 22;79(4):954-60.

Vestitol is an isoflavonoid isolated from Brazilian red propolis with potential anti-inflammatory activity. This study investigated the mechanism of action of vestitol on the modulation of neutrophil migration in the inflammatory process. Pre-treatment with vestitol at 1, 3, or 10 mg/kg reduced LPS- or mBSA-induced neutrophil migration and the release of CXCL1/KC and CXCL2/MIP-2 in vivo. Likewise, pre-treatment with vestitol at 1, 3, or 10 muM reduced the levels of CXCL1/KC and CXCL2/MIP-2 in macrophage supernatants in vitro. Moreover, the administration of vestitol (10 mg/kg) reduced leukocyte rolling and adherence in the mesenteric microcirculation of mice. The pre-treatment with vestitol (10 mg/kg) in iNOS(-/-) mice did not block its activity concerning neutrophil migration. With regard to the activity of vestitol on neutrophils isolated from the bone marrow of mice, there was a reduction on the chemotaxis of CXCL2/MIP-2 or LTB4-induced neutrophils and on calcium influx after pre-treatment with the compound at 3 or 10 muM. There was no change in CXCR2 expression by neutrophils treated with vestitol at 10 muM. These findings demonstrate that vestitol is a promising novel anti-inflammatory agent.

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