A member of the class of chalcones that is trans-chalcone substituted by hydroxy groups at positions 2', 4' and 6' respectively.

Identification

IUPAC Names

(2E)-3-phenyl-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one

Molecular Formula
C15H12O4
Mass
256.25340
Monoisotopic Mass
256.07356
Charge
0
InChI
InChI=1S/C15H12O4/c16-11-8-13(18)15(14(19)9-11)12(17)7-6-10-4-2-1-3-5-10/h1-9,16,18-19H/b7-6+
InChIKey
LOYXTWZXLWHMBX-VOTSOKGWSA-N
SMILES
Oc1cc(O)c(C(=O)\C=C\c2ccccc2)c(O)c1
Synonyms

2',4',6'-trihydroxychalcone

Species

piper lanceaefolium

NCBI:txid53829111809068

Europe PubMed Central results


Antifungal activity of benzoic acid derivatives from Piper lanceaefolium.

Author: López A, Ming DS, Towers GH.

Abstract: Bioactivity-guided fractionation of a methanol extract from the leaves of Piper lanceaefolium resulted in the isolation of four new benzoic acid derivatives (1-4), together with taboganic acid, pinocembrin, and pinocembrin chalcone. Lanceaefolic acid methyl ester (3) and pinocembrin chalcone displayed activity against Candida albicans with a minimal inhibitory concentration value of 100 microg/mL in both cases.

Antimicrobial activity of flavonoids from Piper lanceaefolium and other Colombian medicinal plants against antibiotic susceptible and resistant strains of Neisseria gonorrhoeae.

Author: Ruddock PS, Charland M, Ramirez S, López A, Neil Towers GH, Arnason JT, Liao M, Dillon JA.

Abstract: <h4>Background</h4>The successful treatment of Neisseria gonorrhoeae (NG) infections is increasingly problematic because of the resistance of this pathogen to multiple antimicrobial agents. This development underscores the need for new antimicrobial sources. In the current study, 21 crude methanol extracts, from 19 plants used in Colombian traditional medicine for cutaneous infections, were screened for antimicrobial activity against NG.<h4>Methods</h4>Extracts were screened by disc susceptibility assay. In addition, the minimum inhibitory concentrations of active compounds from P. lanceaefolium were assayed using a panel of 26 NG strains comprising 12 antibiotic-resistant phenotypes.<h4>Results</h4>In all, 71% of the crude extracts exhibited antibacterial activity against the antibiotic susceptible NG strain WHO V, whereas 10% of the extracts inhibited penicillinase-producing NG strain GC1-182. The crude extract of Piper lanceaefolium was the only extract to show significant activity without ultraviolet (UV) light activation. Preliminary screening identified 3 compounds in this plant possessing antimicrobial activity: the flavonoids 5,7-dihydroxyflavanone (pinocembrin), 2',4',6'-trihydroxychalcone (pinocembrin chalcone), and the prenylated benzoic acid derivative cyclolanceaefolic acid methyl ester. Pinocembrin and pinocembrin chalcone inhibited 100% of the NG panel at 64 μg/mL and 128 μg/mL, respectively, whereas cyclolanceaefolic acid methyl ester inhibited 44% of the strains at 128 μg/mL.<h4>Conclusions</h4>This is the first report of the antibacterial activity of Columbian plants against NG. The activity of the 2 flavonoids, pinocembrin, and pinocembrin chalcone, toward both susceptible and resistant NG strains makes them promising candidates for further research.