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Hamamelitannin

CAS# 469-32-9

Hamamelitannin

2D Structure

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Hamamelitannin

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Chemical Properties of Hamamelitannin

Cas No. 469-32-9 SDF Download SDF
PubChem ID 471118 Appearance White powder
Formula C20H20O14 M.Wt 484.4
Type of Compound Phenols Storage Desiccate at -20°C
Synonyms 2',5'-Di-O-galloyl D-hamamelose
Solubility Soluble in ethanol and methanol; slightly soluble in water
Chemical Name [(2R,3R,4S,5R,6R)-2,5-dihydroxy-6-(hydroxymethyl)-3-(3,4,5-trihydroxybenzoyl)oxyoxan-4-yl] 3,4,5-trihydroxybenzoate
SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OC2C(C(OC(C2OC(=O)C3=CC(=C(C(=C3)O)O)O)O)CO)O
Standard InChIKey LRRLFFLVWQTQGZ-WRMYNCHHSA-N
Standard InChI InChI=1S/C20H20O14/c21-5-12-15(28)16(33-18(29)6-1-8(22)13(26)9(23)2-6)17(20(31)32-12)34-19(30)7-3-10(24)14(27)11(25)4-7/h1-4,12,15-17,20-28,31H,5H2/t12-,15-,16+,17-,20-/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 Hamamelitannin

1 Hamamelis sp. 2 Sanguisorba sp.

Biological Activity of Hamamelitannin

DescriptionHamamelitannin has cytotoxic, and antibiofilm activities. It increases the susceptibility of S. aureus to antibiotic treatment in in vivo Caenorhabditis elegans and mouse mammary gland infection models. It also has a high protective activity on cell damage induced by peroxides.
TargetsAntifection
In vitro

Protective activity of hamamelitannin on cell damage induced by superoxide anion radicals in murine dermal fibroblasts.[Pubmed: 7735252]

Biological & Pharmaceutical Bulletin, 1995, 18(1):59-63.


METHODS AND RESULTS:
Previously we demonstrated that Hamamelitannin (2',5-di-O-galloyl hamamelose) in Hamamelis virginiana L. exhibits potent superoxide-anion scavenging activity. We then examined the physiological and pharmacological activities of Hamamelitannin as well as its functional homologues, gallic acid and syringic acid. The following results were obtained: (1) Hamamelitannin has a higher protective activity against cell damages induced by superoxide anions than gallic acid which is the functional moiety of Hamamelitannin. The protective activity of Hamamelitannin on murine fibroblast-damage induced by superoxide anions was found at a minimum concentration of 50 microM, while the corresponding figure for gallic acid was 100 microM. (2) Pre-treatment of fibroblasts with Hamamelitannin enhances cell survival. (3) The superoxide-anion scavenging activity of the compound in terms of its IC50 value (50% inhibition concentration of superoxide anion radicals generated) was evaluated by ESR spin-trapping.
CONCLUSIONS:
Both Hamamelitannin (IC50 = 1.31 +/- 0.06 microM) and gallic acid (IC50 = 1.01 +/- 0.03 microM) exhibited high superoxide-anion scavenging activity followed by syringic acid (IC50 = 13.90 +/- 2.38 microM). (4) When Hamamelitannin was treated with superoxide anions generated by a KO2-crown ether system, HPLC analysis showed the disappearance of Hamamelitannin and the concomitant formation of Hamamelitannin-derived radicals (g = 2.005, delta H1 = 2.16 G, delta H2 = 4.69 G) was detected by ESR spectrometry.

The Quorum Sensing Inhibitor Hamamelitannin Increases Antibiotic Susceptibility of Staphylococcus aureus Biofilms by Affecting Peptidoglycan Biosynthesis and eDNA Release.[Pubmed: 26828772 ]

Sci Rep. 2016 Feb 1;6:20321.

Treatment of Staphylococcus aureus infections has become increasingly challenging due to the rapid emergence and dissemination of methicillin-resistant strains. In addition, S. aureus reside within biofilms at the site of infection. Few novel antibacterial agents have been developed in recent years and their bacteriostatic or bactericidal activity results in selective pressure, inevitably inducing antimicrobial resistance. Consequently, innovative antimicrobials with other modes of action are urgently needed. One alternative approach is targeting the bacterial quorum sensing (QS) system. Hamamelitannin (2',5-di-O-galloyl-d-hamamelose; HAM) was previously suggested to block QS through the TraP QS system and was shown to increase S. aureus biofilm susceptibility towards vancomycin (VAN) although mechanistic insights are still lacking.
METHODS AND RESULTS:
In the present study we provide evidence that HAM specifically affects S. aureus biofilm susceptibility through the TraP receptor by affecting cell wall synthesis and extracellular DNA release of S. aureus. We further provide evidence that HAM can increase the susceptibility of S. aureus biofilms towards different classes of antibiotics in vitro.
CONCLUSIONS:
Finally, we show that HAM increases the susceptibility of S. aureus to antibiotic treatment in in vivo Caenorhabditis elegans and mouse mammary gland infection models.

In vivo

In vivo antibiofilm effect of cerium, chitosan and hamamelitannin against usual agents of catheter-related bloodstream infections.[Pubmed: 22991425]

Journal of Antimicrobial Chemotherapy, 2013, 68(1):126-130.

Catheter-related bloodstream infections (CRBSIs) are common healthcare-associated infections associated with increased morbidity and medical costs. Antiseptic- and antibiotic-coated central venous catheters (CVCs) have been proposed to reduce the incidence of CRBSIs, with variable success. The aim of this study was to determine the in vivo antibiofilm activity of biocompatible and inexpensive compounds, such as cerium nitrate, chitosan and Hamamelitannin, against usual agents of CRBSIs.
METHODS AND RESULTS:
The antibiofilm effect of cerium nitrate, chitosan and Hamamelitannin was tested against Staphylococcus epidermidis, Staphylococcus aureus, Acinetobacter baumannii and Candida albicans in a mouse foreign body infection model, using polyurethane catheter segments. Biofilm formation was assessed with a crystal violet assay to quantify the total biomass, with a tetrazolium reduction assay to quantify the metabolic activity and with scanning electron microscopy. At subinhibitory concentrations, cerium nitrate significantly reduced biofilm formation by C. albicans, chitosan significantly decreased biofilm formation by S. epidermidis and C. albicans, and Hamamelitannin significantly inhibited all bacterial biofilms.
CONCLUSIONS:
The in vivo antibiofilm effect of cerium nitrate against C. albicans and of chitosan against C. albicans and S. epidermidis, at subinhibitory concentrations, makes them promising alternatives to coat CVCs. Moreover, the microbicidal effect on a wider range of CVC colonizers was previously reported in vitro for both compounds, at higher concentrations. For all bacterial strains, the highest in vivo antibiofilm efficacy was achieved with Hamamelitannin. For A. baumannii, this is the first report of in vivo inhibition.

Protocol of Hamamelitannin

Cell Research

Hamamelitannin from witch hazel (Hamamelis virginiana) displays specific cytotoxic activity against colon cancer cells.[Pubmed: 22216935]

Journal of Natural Products, 2012, 75(1):26-33.

Hamamelis virginiana (witch hazel) bark is a rich source of condensed and hydrolyzable tannins reported to exert a protective action against colon cancer. The present study characterizes different witch hazel tannins as selective cytotoxic agents against colon cancer.
METHODS AND RESULTS:
To cover the structural diversity of the tannins that occur in H. virginiana bark, the hydrolyzable tannins, Hamamelitannin and pentagalloylglucose, together with a proanthocyanidin-rich fraction (F800H4) were selected for the study. Treatment with these compounds reduced tumor viability and induced apoptosis, necrosis, and S-phase arrest in the cell cycle of HT29 cells, with Hamamelitannin being the most efficient. Owing to polyphenol-mediated H(2)O(2) formation in the incubation media, the antiproliferative effect was determined in the presence and absence of catalase to rule out any such interference. The presence of catalase significantly changed the IC(50) only for F800H4. Furthermore, at concentrations that inhibit the growth of HT29 cells by 50%, Hamamelitannin had no harmful effects on NCM460 normal colonocytes, whereas pentagalloylglucose inhibited both cancerous and normal cell growth.
CONCLUSIONS:
Using the TNPTM assay, we identified a highly reactive phenolic position in Hamamelitannin, which may explain its efficacy at inhibiting colon cancer growth.

Hamamelitannin Dilution Calculator

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Preparing Stock Solutions of Hamamelitannin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0644 mL 10.322 mL 20.6441 mL 41.2882 mL 51.6102 mL
5 mM 0.4129 mL 2.0644 mL 4.1288 mL 8.2576 mL 10.322 mL
10 mM 0.2064 mL 1.0322 mL 2.0644 mL 4.1288 mL 5.161 mL
50 mM 0.0413 mL 0.2064 mL 0.4129 mL 0.8258 mL 1.0322 mL
100 mM 0.0206 mL 0.1032 mL 0.2064 mL 0.4129 mL 0.5161 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 Hamamelitannin

Hamamelitannin from witch hazel (Hamamelis virginiana) displays specific cytotoxic activity against colon cancer cells.[Pubmed:22216935]

J Nat Prod. 2012 Jan 27;75(1):26-33.

Hamamelis virginiana (witch hazel) bark is a rich source of condensed and hydrolyzable tannins reported to exert a protective action against colon cancer. The present study characterizes different witch hazel tannins as selective cytotoxic agents against colon cancer. To cover the structural diversity of the tannins that occur in H. virginiana bark, the hydrolyzable tannins, Hamamelitannin and pentagalloylglucose, together with a proanthocyanidin-rich fraction (F800H4) were selected for the study. Treatment with these compounds reduced tumor viability and induced apoptosis, necrosis, and S-phase arrest in the cell cycle of HT29 cells, with Hamamelitannin being the most efficient. Owing to polyphenol-mediated H(2)O(2) formation in the incubation media, the antiproliferative effect was determined in the presence and absence of catalase to rule out any such interference. The presence of catalase significantly changed the IC(50) only for F800H4. Furthermore, at concentrations that inhibit the growth of HT29 cells by 50%, Hamamelitannin had no harmful effects on NCM460 normal colonocytes, whereas pentagalloylglucose inhibited both cancerous and normal cell growth. Using the TNPTM assay, we identified a highly reactive phenolic position in Hamamelitannin, which may explain its efficacy at inhibiting colon cancer growth.

Hamamelitannin Analogues that Modulate Quorum Sensing as Potentiators of Antibiotics against Staphylococcus aureus.[Pubmed:27095479]

Angew Chem Int Ed Engl. 2016 May 23;55(22):6551-5.

The modulation of bacterial communication to potentiate the effect of existing antimicrobial drugs is a promising alternative to the development of novel antibiotics. In the present study, we synthesized 58 analogues of Hamamelitannin (HAM), a quorum sensing inhibitor and antimicrobial potentiator. These efforts resulted in the identification of an analogue that increases the susceptibility of Staphylococcus aureus towards antibiotics in vitro, in Caenorhabditis elegans, and in a mouse mammary gland infection model, without showing cytotoxicity.

The Quorum Sensing Inhibitor Hamamelitannin Increases Antibiotic Susceptibility of Staphylococcus aureus Biofilms by Affecting Peptidoglycan Biosynthesis and eDNA Release.[Pubmed:26828772]

Sci Rep. 2016 Feb 1;6:20321.

Treatment of Staphylococcus aureus infections has become increasingly challenging due to the rapid emergence and dissemination of methicillin-resistant strains. In addition, S. aureus reside within biofilms at the site of infection. Few novel antibacterial agents have been developed in recent years and their bacteriostatic or bactericidal activity results in selective pressure, inevitably inducing antimicrobial resistance. Consequently, innovative antimicrobials with other modes of action are urgently needed. One alternative approach is targeting the bacterial quorum sensing (QS) system. Hamamelitannin (2',5-di-O-galloyl-d-hamamelose; HAM) was previously suggested to block QS through the TraP QS system and was shown to increase S. aureus biofilm susceptibility towards vancomycin (VAN) although mechanistic insights are still lacking. In the present study we provide evidence that HAM specifically affects S. aureus biofilm susceptibility through the TraP receptor by affecting cell wall synthesis and extracellular DNA release of S. aureus. We further provide evidence that HAM can increase the susceptibility of S. aureus biofilms towards different classes of antibiotics in vitro. Finally, we show that HAM increases the susceptibility of S. aureus to antibiotic treatment in in vivo Caenorhabditis elegans and mouse mammary gland infection models.

Dressings Loaded with Cyclodextrin-Hamamelitannin Complexes Increase Staphylococcus aureus Susceptibility Toward Antibiotics Both in Single as well as in Mixed Biofilm Communities.[Pubmed:26891369]

Macromol Biosci. 2016 Jun;16(6):859-69.

Bacteria reside within biofilms at the infection site, making them extremely difficult to eradicate with conventional wound care products. Bacteria use quorum sensing (QS) systems to regulate biofilm formation, and QS inhibitors (QSIs) have been proposed as promising antibiofilm agents. Despite this, few antimicrobial therapies that interfere with QS exist. Nontoxic hydroxypropyl-beta-cyclodextrin-functionalized cellulose gauzes releasing a burst of the antibiotic vancomycin and the QSI Hamamelitannin are developed, followed by a sustained release of both. The gauzes affect QS and biofilm formation of Pseudomonas aeruginosa and Staphylococcus aureus in an in vitro model of chronic wound infection and can be considered as candidates to be used to prevent wound infection as well as treat infected wounds.

Novel hamamelitannin analogues for the treatment of biofilm related MRSA infections-A scaffold hopping approach.[Pubmed:27823882]

Eur J Med Chem. 2017 Feb 15;127:757-770.

Antimicrobial research is increasingly being focused on the problem of resistance and biofilm formation. Hamamelitannin (HAM) was recently identified as an antimicrobial potentiator for conventional antibiotics towards Staphylococcus aureus. This paper describes the synthesis and biological evaluation of novel Hamamelitannin analogues with alternative central scaffolds. Via a ligand-based approach, several interesting compounds with improved synthetic accessibility were identified as potentiators for vancomycin in the treatment of MRSA infections.

Description

Hamamelitannin, a polyphenol extracted from the bark of Hamamelis virginiana, is a quorum-sensing (QS) inhibitor. Hamamelitannin increases antibiotic susceptibility of staphylococcus aureus biofilms by affecting peptidoglycan biosynthesis and eDNA release.

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