Structure-activity relationships of cinnamaldehyde and eugenol derivatives against plant pathogenic fungi

Xie, Yongjian; Huang, Qianqian; Wang, Zhunjing; Cao, Haiyan; Zhang, Dayu

doi:10.1016/j.indcrop.2016.12.043

Cited by 60 publications

(38 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Others have shown that ( E )-cinnamaldehyde ( 7 ) also has antimicrobial activity [ 26 , 35 , 54 , 55 ]. For example, Zhang and coworkers [ 35 ] studied the structure-activity relationships (SAR) of cinnamaldehyde ( 7 ) and eugenol derivatives against two plant pathogenic fungi, Rhizoctonia solani and Fusarium oxysporum . It displayed that many derivatives showed good activities against both fungi.…”

Section: Resultsmentioning

confidence: 99%

“…Both species were chosen as representatives of dicot and monocot plants, respectively. We selected an aldehyde chemical class since there are several reports indicating that natural and synthetic aldehydes [ 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ] or crude extracts containing aldehydes [ 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ] could interrupt the germination, growth, and development of plants, algae, and microorganisms. Furthermore, numerous aldehydes are commercially available in pure form which can be directly purchased.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Inhibitory Effects of a Variety of Aldehydes on Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

2018

View full text Add to dashboard Cite

Thirty-seven commercial aldehydes containing aliphatic chains and aromatic rings as well as heteroaromatic rings were evaluated for their inhibitory activities against Chinese amaranth (Amaranthus tricolor L.) and barnyardgrass (Echinochloa crus-galli (L.) Beauv). Polysorbate 80 (Tween® 80) was used as a surfactant and the research was preliminarily conducted at 400 μM of all aldehydes. Among these aldehydes, (E)-cinnamaldehyde (7) showed the greatest inhibitory effect on seed germination, shoot and root growth of Chinese amaranth by 54.55%, 75.53%, and 85.13% respectively. Similarly, (E)-crotonaldehyde (5), a related α,β-unsaturated aldehyde, inhibited the germination and seedling growth of the tested species at a high percentage. Apart from these two unsaturated aldehydes, no other aliphatic aldehydes had a harmful effect on Chinese amaranth. In terms of benzaldehyde (6), it had no effect on the tested plant; however, many of its derivatives displayed some inhibitory activity. Furthermore, for the ten common heteroaromatic aldehydes, picolinaldehyde (32) had a high inhibitory effect on Chinese amaranth which closely related to the effect of (E)-crotonaldehyde (5) and (E)-cinnamaldehyde (7), whereas, other heteroaromatic aldehydes showed lower effects. In the case of a monocot plant, barnyardgrass, no tested aldehydes reduced seed germination, however, (E)-cinnamaldehyde (7), 2,4,6-trimethoxybenzaldehyde (16) and 4-(dimethylamino)benzaldehyde (24) could inhibit the seedling growth of the plant with low to moderate levels. The herbicidal effects of the most active aldehydes were then further investigated in order to find the minimum concentration of these aldehydes suppressing the germination and growth of the tested plants. At concentrations as low as 50–100 μM some aldehydes could inhibit the seedling growth of the tested species. The structure-activity relationship (SAR) study reported here demonstrates the chemical clues governing the inhibitory activity of aldehydes which could be utilized in the development of highly effective herbicides in the near future.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Inhibitory Effects of a Variety of Aldehydes on Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

2018

View full text Add to dashboard Cite

show abstract

“…Phenol antifungal activity was shown to depend on the chemical structure. In particular, aldehydes, acid groups, conjugated double bonds, and the length of CH chain outside the ring have increased the antifungal activity (Xie et al, 2017). While aldehydes and acid groups may be more prone to react with amino acid residues of proteins through hydrogen bonds and induce conformational modification because of the proton release ability, the length of the CH chain increases hydrophobicity, a major determinant of phenol capability to enter the plasma membrane (Ben Arfa et al, 2006;Dambolena et al, 2011).…”

Section: (I) Phenolic Compoundsmentioning

confidence: 99%

Plant Bioactive Compounds in Pre- and Postharvest Management for Aflatoxins Reduction

et al. 2020

View full text Add to dashboard Cite

Aflatoxins (AFs) are secondary metabolites produced by Aspergillus spp., known for their hepatotoxic, carcinogenic, and mutagenic activity in humans and animals. AF contamination of staple food commodities is a global concern due to their toxicity and the economic losses they cause. Different strategies have been applied to reduce fungal contamination and AF production. Among them, the use of natural, plant-derived compounds is emerging as a promising strategy to be applied to control both Aspergillus spoilage and AF contamination in food and feed commodities in an integrated pre-and postharvest management. In particular, phenols, aldehydes, and terpenes extracted from medicinal plants, spices, or fruits have been studied in depth. They can be easily extracted, they are generally recognized as safe (GRAS), and they are foodgrade and act through a wide variety of mechanisms. This review investigated the main compounds with antifungal and anti-aflatoxigenic activity, also elucidating their physiological role and the different modes of action and synergies. Plant bioactive compounds are shown to be effective in modulating Aspergillus spp. contamination and AF production both in vitro and in vivo. Therefore, their application in pre-and postharvest management could represent an important tool to control aflatoxigenic fungi and to reduce AF contamination.

show abstract

“…This may be attributed to the cinnamaldehyde containing species (C. verum) having stronger antimicrobial activity than the eugenol containing species (C. zeylanicum). Antifungal activity of eugenol and cinnamaldehyde containing essential oils and the compounds alone was previously reported, with stronger inhibition being reported for cinnamaldehyde [41,42]. Cinnamomum verum was also the essential oil involved in the lowest MIC value in combinations against C. albicans.…”

mentioning

confidence: 56%

Commercial Essential Oil Combinations against Topical Fungal Pathogens

Orchard

Vuuren

Viljoen

2019

Natural Product Communications

View full text Add to dashboard Cite

Essential oils are amongst the most popular natural products recommended for the treatment of topical fungal infections. This study investigated the antifungal activity of 128 essential oil combinations against fungal pathogen reference strains using the broth microdilution technique to determine the minimum inhibitory concentration (MIC). The essential oils were investigated at a volume of 100 µL and the combinations comprised of 50:50 µL. Each combination was tested in triplicate and the mean recorded. The fractional inhibitory concentration index was calculated for combinations, and synergistic interactions were investigated further at different ratios and plotted on isobolograms. The fungal pathogens were found to be highly susceptible to the essential oil combinations, with Trichophyton mentagrophytes being inhibited by all but one combination. The essential oil combinations containing Cinnamomum verum or Santalum austrocaledonicum were found to display the strongest inhibition with MIC values as low as 0.06 mg/mL. Potential combinations against fungal pathogens have been presented that could be studied in clinical settings with the goal of decreasing the need for systemic or prolonged antifungal treatments that may result in treatment failure or resistance.

show abstract

Structure-activity relationships of cinnamaldehyde and eugenol derivatives against plant pathogenic fungi

Cited by 60 publications

References 47 publications

Inhibitory Effects of a Variety of Aldehydes on Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

Inhibitory Effects of a Variety of Aldehydes on Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

Plant Bioactive Compounds in Pre- and Postharvest Management for Aflatoxins Reduction

Commercial Essential Oil Combinations against Topical Fungal Pathogens

Contact Info

Product

Resources

About