# Natural Strategies to Preserve Alcohol-Free Beer: Phenolamide Dimers with Anti-Yeast Potential

**Authors:** Annemiek van Zadelhoff, Denise Dozio, Francesca Annunziata, Aziza Caccia, Sabrina Dallavalle, Yingyu Zhou, Sarah van Dinteren, Jean-Paul Vincken, Andrea Pinto, Wouter J. C. de Bruijn

PMC · DOI: 10.1021/acs.jafc.5c09118 · 2026-02-22

## TL;DR

Researchers found that certain natural compounds, called phenolamide dimers, can inhibit yeast growth in alcohol-free beer, offering a natural preservative solution.

## Contribution

The study demonstrates that amidation and oxidative coupling enhance anti-yeast activity of hydroxycinnamic acid derivatives.

## Key findings

- Hydroxycinnamic acid dimers and HCAgms did not inhibit yeast, but HCAgm dimers did.
- Specific HCAgm dimers like CouAgm-4-O-7′/3-8′-DCouAgm and FerAgm-4-O-7′/3-8′-DFerAgm showed anti-yeast activity in beer.
- A new agmatine amide of poacic acid had increased antiyeast activity compared to its monomeric precursors.

## Abstract

Trends in clean label food and the growing popularity
of alcohol-free
beers have led to a demand for natural compounds to prevent microbial
spoilage. Oxidative coupling products of hydroxycinnamic acids and
their amides, i.e. phenolamides, obtained via chemo-enzymatic synthesis
and from barley rootlets, a beer brewing byproduct, were tested for
their inhibitory activity against the beer spoilage yeast Saccharomyces cerevisiae subsp. diastaticus. Hydroxycinnamic acids, their dimers, and hydroxycinnamoylagmatines
(HCAgms) did not inhibit the yeast. However, inhibitory activity was
observed with HCAgm dimers. In particular, CouAgm-4-O-7′/3-8′-DCouAgm and FerAgm-4-O-7′/3-8′-DFerAgm
were active at 46–255 μg/mL in beer. Notably, the newly
synthesized agmatine amide of poacic acid, a stilbenoid dimer of ferulic
acid, showed increased antiyeast activity compared to its monomeric
precursors. These results demonstrate that amidation and oxidative
coupling can increase the antiyeast activity of hydroxycinnamic acid
derivatives, and that hydroxycinnamoylagmatine dimers possess potential
as preservatives against wild yeast spoilage in beer.

## Linked entities

- **Chemicals:** poacic acid (PubChem CID 10337420), ferulic acid (PubChem CID 445858)

## Full-text entities

- **Diseases:** toxicity (MESH:D064420), fungal (MESH:D009181)
- **Chemicals:** aluminum (MESH:D000535), Fer-8-8'/9-O-7'-DFer (-), dioxane (MESH:C025223), NaHCO3 (MESH:D017693), tyramine (MESH:D014439), H2O2 (MESH:D006861), ethyl acetate (MESH:C007650), FerAgm (MESH:C419343), hexane (MESH:D006586), glycerol (MESH:D005990), toluene (MESH:D014050), Na2SO4 (MESH:C012036), hordatine B (MESH:C528924), TFA (MESH:D014269), putrescine (MESH:D011700), acetone (MESH:D000096), poly)amines (MESH:D011073), Potassium sorbate (MESH:D013011), carbon dioxide (MESH:D002245), lactones (MESH:D007783), C-8'S (MESH:C037690), H (MESH:D006859), Alcohol (MESH:D000438), silica gel (MESH:D058428), metal (MESH:D008670), Ethyl ferulate (MESH:C099085), NaCl (MESH:D012965), Poacic acid (MESH:C000598562), methanol (MESH:D000432), phosphate (MESH:D010710), FA (MESH:C030544), acid (MESH:D000143), sugar (MESH:D000073893), Hydroxycinnamic Acid (MESH:D003373), HOBt (MESH:C011852), DCM (MESH:D008752), N2 (MESH:D009584), stilbenoid (MESH:D013267), agar (MESH:D000362), Agmatine (MESH:D000376), chitin (MESH:D002686), triethylamine (MESH:C016162), beta-1,3-glucan (MESH:C033363), ACN (MESH:C032159), H2O (MESH:D014867), amides (MESH:D000577), feruloyl-CoA. (MESH:C119167), Ferulic Acid (MESH:C004999), hydroxy acids (MESH:D006880), hordatine A (MESH:C528923), HCl (MESH:D006851), isopropyl alcohol (MESH:D019840), acetic acid (MESH:D019342), cyclohexane (MESH:C506365), EtOH (MESH:D000431), 13C (MESH:C000615229), NaOH (MESH:D012972)
- **Species:** Leptospira sp. AB (species) [taxon 103236], Alternaria solani (species) [taxon 48100], Bacteria Latreille et al. 1825 (Bacteria stick insect, genus) [taxon 629395], Levilactobacillus brevis (species) [taxon 1580], Polytrichum commune (species) [taxon 3213], Penicillium commune (species) [taxon 36653], Hordeum (barleys, genus) [taxon 4512], Oryza sativa (Asian cultivated rice, species) [taxon 4530], Hordeum vulgare (barley, species) [taxon 4513], Pyricularia oryzae (rice blast fungus, species) [taxon 318829], Aspergillus niger (species) [taxon 5061], Saccharomyces cerevisiae (baker's yeast, species) [taxon 4932], Phytophthora sojae (species) [taxon 67593], Sclerotinia sclerotiorum (species) [taxon 5180]

## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12964544/full.md

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Source: https://tomesphere.com/paper/PMC12964544