Hamamelitannin

Names

[ CAS No. ]:
469-32-9

[ Name ]:
Hamamelitannin

[Synonym ]:
HAMAMELOFURANOSE 2',5-DIGALLATE
2',5-DigalloylhaMaMelofuranose
2,3-Digalloylglucose
[(2R,3R,4R)-3,4,5-Trihydroxytetrahydrofuran-2,4-diyl]bis(methylen)bis(3,4,5-trihydroxybenzoat)
2-C-[[(3,4,5-Trihydroxybenzoyl)oxy]methyl]-D-ribofuranose 5-(3,4,5-trihydroxybenzoate)
Bis(3,4,5-trihydroxybenzoate) de [(2R,3R,4R)-3,4,5-trihydroxytétrahydrofurane-2,4-diyl]bis(méthylène)
2',5-digalloylhamamelose
hamamelitanin
Hamamelitannin
[(2R,3R,4R)-3,4,5-Trihydroxytetrahydrofuran-2,4-diyl]bis(methylene) bis(3,4,5-trihydroxybenzoate)
O5-Galloyl-2-galloyloxymethyl-D-ribose
5-O-(3,4,5-Trihydroxybenzoyl)-2-C-{[(3,4,5-trihydroxybenzoyl)oxy]methyl}-D-ribofuranose
D-Ribofuranose, 2-C-[[(3,4,5-trihydroxybenzoyl)oxy]methyl]-, 5-(3,4,5-trihydroxybenzoate)
2-C-(Hydroxymethyl)-D-ribofuranose 2',5-Digallate

Biological Activity

[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[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Hamamelitannin displays specific cytotoxic activity against colon cancer cells[3].

[References]

[1]. Kiran MD, et al. Discovery of a quorum-sensing inhibitor of drug-resistant staphylococcal infections by structure-based virtual screening. Mol Pharmacol. 2008 May;73(5):1578-86.

[2]. Cobrado L, et al. In vivo antibiofilm effect of cerium, chitosan and hamamelitannin against usual agents of catheter-related bloodstream infections. J Antimicrob Chemother. 2013 Jan;68(1):126-30.

[3]. Sánchez-Tena S, et al. Hamamelitannin displays specific cytotoxic activity against colon cancer cells. J Nat Prod. 2012 Jan 27;75(1):26-33.

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
941.7±65.0 °C at 760 mmHg

[ Melting Point ]:
145-147ºC

[ Molecular Formula ]:
C₂₀H₂₀O₁₄

[ Molecular Weight ]:
484.364

[ Flash Point ]:
329.0±27.8 °C

[ Exact Mass ]:
484.085297

[ PSA ]:
243.90000

[ LogP ]:
2.91

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.746

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Quorum sensing inhibitors increase the susceptibility of bacterial biofilms to antibiotics in vitro and in vivo.

Antimicrob. Agents Chemother. 55 , 2655-2661, (2011)

Although the exact role of quorum sensing (QS) in various stages of biofilm formation, maturation, and dispersal and in biofilm resistance is not entirely clear, the use of QS inhibitors (QSI) has bee...

Hamamelitannin from witch hazel (Hamamelis virginiana) displays specific cytotoxic activity against colon cancer cells.

J. Nat. Prod. 75 , 26-33, (2012)

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 wit...

Cerium, chitosan and hamamelitannin as novel biofilm inhibitors?

J. Antimicrob. Chemother. 67 , 1159-62, (2012)

The colonization of indwelling medical devices and subsequent biofilm formation represents a global challenge since it promotes the persistence of infection and contributes to antimicrobial resistance...