Chinese Licorice Extract for Anti-aging, Antibacterial and Breath-freshening Effects

Aug 1, 2013 | Contact Author | By: Stefan Gafner, PhD, Tom’s of Maine
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Title: Chinese Licorice Extract for Anti-aging, Antibacterial and Breath-freshening Effects
Glycyrrhiza uralensis (Chinese licorice) extractx matrix metalloproteinasesx antibacterialx volatile sulfur compoundx
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Keywords: Glycyrrhiza uralensis (Chinese licorice) extract | matrix metalloproteinases | antibacterial | volatile sulfur compound

Abstract: This article reviews in vitro studies that have found Chinese licorice extract to impart potent antibacterial and soothing properties, which make it an interesting candidate for applications in oral and personal care. Further, a clinical study is described in brief, assessing the ability of a supercritical CO2 extract from Chinese licorice to impart breath-freshening properties.

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S Gafner, Chinese Licorice Extract for Anti-aging, Antibacterial and Breath-freshening Effects, Cosm & Toil 128(8) 552 (2013)

Market Data

  • In oral care, health concerns are the number one driver of sales.
  • Consumers are also looking to whiten teeth and freshen breath.
  • Products that provide multiple benefits are proving to be the most attractive.
  • Marketers have had success with "product suites," i.e., groupings of products presented as a complete oral care package.
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Extracts from herbal materials are inherently complex, and Chinese licorice is no exception. To date, close to 40 different compounds have been characterized in this extract, most of which have a rather unusual structure (see Figure 1). The main components are isoflavonoids; the isoflavans licoricidin and licorisoflavan A account for more than 15% of the extract. A number of other isoflavans, isoflavanones and isoflavones; licoricone and licoisoflavone B; pterocarpans; flavones such as liquiritigenin; and 2-arylbenzofurans have also been described (see Chinese Licorice Compounds).1 In addition, the extract contains coumarins, coumestans, fatty acids, glycosides of liquiritigenin and isoliquiritigenin, and triterpene glycosides, i.e., saponins which give licorice roots its typical sweet taste.

One characteristic of most of these flavonoids is the addition of one or two isoprene units to the base structure. Isoflavanoids are rather rare in nature, and some of the subgroups, e.g., the coumestans and 2-arylbenzofurans, have less than 100 structures reported to date—compared with more than 1,000 known flavones and more than 1,500 flavonols. The addition of one or two isoprene units makes for an even more unusual chemical structure. The isoprene moiety can be open, as with licoricidin, or form a pyran-ring, e.g., licoisoflavone B. Publications on the relationship between the chemical structure and antibacterial activity of isoflavonoids have shown that isoprene substituents are important for such activity.1, 2 Molecules with two isoprene substituents have better activity than those with only one, which in turn have better activity than isoflavonoids without a prenyl moiety. An isoprene unit in position C-6 seems to be particularly important, as is a hydroxyl substituent in position C-7. In cases where the isoprene unit is fused to form a pyran ring, the activity noticeably decreases.2 The antimicrobial effect of isoflavones has been attributed to their phenolic hydroxyl groups, which allow the molecules to act as inhibitors of microbial enzymes. The presence of isoprene groups increases the lipophilicity of the isoflavonoid, which seems to be a requirement to disrupt the function of the protoplasmic cell membrane of Gram-positive bacteria and thus interfere with the transport of nutrients into the cell.3

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This content is adapted from an article in GCI Magazine. The original version can be found here.

 

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Table 1. Summary of the organoleptic scores using toothpaste containing Glycyrrhiza uralensis supercritical extract

Table 1. Summary of the organoleptic scores using toothpaste containing Glycyrrhiza uralensis supercritical extract

The mean organoleptic ratings by the odor judges (see Table 1) showed a 31.7% reduction in oral malodor, while the results with the VSC score (see Table 2) were reduced by 48.4%, compared with the baseline.

Table 2. Summary of the VSC scores using toothpaste containing Glycyrrhiza uralensis supercritical extract; VSC scores are expressed in ppb

Table 2. Summary of the VSC scores using toothpaste containing <em>Glycyrrhiza uralensis</em> supercritical extract; VSC scores are expressed in ppb

The mean organoleptic ratings by the odor judges (see Table 1) showed a 31.7% reduction in oral malodor, while the results with the VSC score (see Table 2) were reduced by 48.4%, compared with the baseline.

Figure 1. Close to 40 different compounds, some shown here, have been characterized in Chinese licorice extract.

Figure 1. Close to 40 different compounds, some shown here, have been characterized in Chinese licorice extract.

To date, close to 40 different compounds have been characterized in this extract, most of which have a rather unusual structure (see Figure 1).

Chinese Licorice Compounds

Isoflavans: glyasperin C, glyasperin D and vestitol
Isoflavanones: glyasperin F, glyasperin K and dihydrolicoisoflavone
Isoflavones: allolicoisoflavone A, 6,8-diprenylgenistein [8-(g,g-dimethylallyl)-wighteone]
Pterocarpans: glycycarpan, medicarpin, 1-methoxyphaseollidin and 1-methoxyficifolinol
Flavones: liquiritigenin 2-Arylbenzofurans: gancaonin I and licocoumarone
Coumarins: glycyrin and glycycoumarin
Coumestans: isoglycyrol
Additional compounds: licoricone, licoisoflavone B and fatty acids

Footnote (CT1308 Gafney)

a The process used is trademarked by FLAVEX Naturextrakte GmbH.

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