Synthesis and characterization of humic acid-like polymers

Hänninen, Kari; Klöcking, R.; Helbig, B

doi:10.1016/0048-9697(87)90502-x

Cited by 41 publications

(21 citation statements)

References 8 publications

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“…To better define the chemical components associated with the adverse effects assumed to result from the consumption of contaminated artesian well water, synthetic HA was synthesized from monomeric protocatechuic acid and, thus free of other inorganic contaminants, was used for this study according to the published procedure, with slight modifications as described previously [21]. For oxidative polymerization, 1 g of protocatechuic acid in 100 mL of distilled water was oxidized with sodium periodate for 24 h in a water bath at 50 • C with shaking.…”

Section: Preparation Of Synthetic Hamentioning

confidence: 99%

Humic acid induced genotoxicity in human peripheral blood lymphocytes using comet and sister chromatid exchange assay

Hseu

Chen

et al. 2008

Journal of Hazardous Materials

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Section: Preparation Of Synthetic Hamentioning

confidence: 99%

Humic acid induced genotoxicity in human peripheral blood lymphocytes using comet and sister chromatid exchange assay

Hseu

Chen

et al. 2008

Journal of Hazardous Materials

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“…Synthetic HA was synthesized according to the published procedure, with slight modifications as described previously (Haninen et al, 1987). For oxidative polymerization, 1 g of protocatechuic acid in 100 ml of distilled water was oxidized with sodium periodate for 24 h in a water bath at 50 jC with shaking.…”

Section: Preparation Of Synthetic Hamentioning

confidence: 99%

Humic acid induces apoptosis in human premyelocytic leukemia HL-60 cells

Yang

Hseu²,

Hseu

et al. 2004

Life Sciences

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“…polyanions derived from phenolic compounds (Senesi, 1994). Beside colour, solubility, MW and polyanionic character, the similarity ofHA-like polymers to naturally occurring HA is revealed in their IR spectra (Hanninen et al, 1987;Helbig et aI., 1994). The broad peak at 3400 cm" corresponds to hydrogen bridge-bound hydroxylic groups (Bellamy, 1980).…”

Section: Discussionmentioning

confidence: 99%

Anti-Herpes Simplex Virus Type 1 Activity of Humic Acid-Like Polymers and Their O-Diphenolic Starting Compounds

Helbig

Klöcking

Wutzler

1997

Antivir Chem Chemother

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SummaryPhenolic polymers of the humic acid (HA) type, like other polyanionic substances, are inhibitors of herpes simplex virus type 1 (HSV-1) replication. The antiviral potency of the low molecular weight (MW) phenolic starting compounds has not been investigated systematically up to now. To reveal possible relationships between the chemical structure of o-diphenolicstarting compounds and the anti-HSV-1 activity of HA-like polymers, nine polymers were synthesized by oxidation of the corresponding 0-dihydroxybenzene derivatives. They were characterized by MW distribution, Fourier transform infra-red spectra and functional group analysis. Using an XTI-based tetrazolium reduction assay, both the low MW starting compounds and the synthesized polymers were examined for their antiviral and cytotoxic activities in HSV-1-infected Vero cells. The results demonstrate that mostof the starting compounds failed to inhibit herpesvirus replication. The polymeric oxidation products (OP), however, developed detectable anti-HSV-1 activity with IC 50 values in the range 2.3 [the OP of 3,4 dihydroxycinnamic acid (caffeic acid); KOPl to 42.1 Jlg mL-1 (3,4-dihydroxytoluene OP). The CC 50 of polymers varied between 40.8 (3,4-dihydroxybenzaldehyde OP) and >128 Jlg mL-1 (most polymers). Functional group analysis revealed that the presence of carboxylic groups in the starting compounds enhanced the antiviral activity and reduced the cytotoxicity of polymers. The introduction of a C=C double bond into the side chain [i.e, caffeic acid; 3-0-(3,4-dihydroxycinnamoyl)-D-chinic acid (chlorogenic acid; CH)l yielded the most effective polymers (KOP, CHOP).These may be considered as leader substances for HSV-1 inhibitors of the HA type.

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Synthesis and characterization of humic acid-like polymers

Cited by 41 publications

References 8 publications

Humic acid induced genotoxicity in human peripheral blood lymphocytes using comet and sister chromatid exchange assay

Humic acid induced genotoxicity in human peripheral blood lymphocytes using comet and sister chromatid exchange assay

Humic acid induces apoptosis in human premyelocytic leukemia HL-60 cells

Anti-Herpes Simplex Virus Type 1 Activity of Humic Acid-Like Polymers and Their O-Diphenolic Starting Compounds

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