{"id":56883,"date":"2024-03-20T11:50:56","date_gmt":"2024-03-20T11:50:56","guid":{"rendered":"https:\/\/biomedpharmajournal.org\/?p=56883"},"modified":"2024-06-04T04:09:26","modified_gmt":"2024-06-04T04:09:26","slug":"chromatographic-profile-of-polyphenols-in-the-agastache-foeniculum-pursh-kuntze-herb-evaluation-of-optimal-extraction-efficiency","status":"publish","type":"post","link":"https:\/\/biomedpharmajournal.org\/staging\/vol17no1\/chromatographic-profile-of-polyphenols-in-the-agastache-foeniculum-pursh-kuntze-herb-evaluation-of-optimal-extraction-efficiency\/","title":{"rendered":"Chromatographic Profile of Polyphenols in the Agastache foeniculum (Pursh) Kuntze Herb: Evaluation of Optimal Extraction Efficiency"},"content":{"rendered":"\n

Introduction<\/strong><\/p>\n\n\n\n

In the process of\ndeveloping new medicines from herbal raw materials, it is important to\ndetermine the spectrum of major bioactive compounds. Scientists have proven a\nsignificant influence of genetic prerequisites (depending on the chosen\nsubspecies, chemotype\/variety, and age of the plant),\nclimatic conditions and cultivation features on the accumulation of polyphenols\nin plants’ raw material1<\/sup>.  Undoubtedly,\nthe choice of the extraction method, type of solvent, the raw\nmaterial-extractant ratio, time, temperature, rate, and multiplicity of\nextraction play key roles in the phytochemical analysis2<\/sup>.  <\/p>\n\n\n\n

The use of water-methanol and water-ethanol mixtures is quite effective due to their ability to extract both hydrophilic and hydrophobic compounds of a polyphenolic nature. Besides, these two solvents are the most compatible with the principles of green extraction among a whole range of organic solvents3<\/sup>. The pharmaceutical and food industries increasingly prefer green solvents (water, ethanol, deep eutectic solvents, etc.) for extraction due to their safety and recycling4,5<\/sup>. <\/p>\n\n\n\n

It should be noted that the extremity of extraction of bioactive compounds from plant raw material can be associated with risks through various factors. Thus, the high extraction levels may elevate the concentration of active compounds, potentially increasing the risk of undesired effects or toxicity. However, the low extraction efficiency can result in inadequate isolation of beneficial compounds, limiting therapeutic potential and raising the risk of insufficient drug efficacy. Thus, achieving an optimal balance in extraction levels becomes crucial for minimizing risks and attaining the desired pharmacological effect of developed herbal substances6<\/sup>.<\/p>\n\n\n\n

The Giant hyssop (Agastache<\/em> Clayton ex Gronov, Lamiaceae Martinov family) genus comprises 22 species native mostly to\nNorth America, and only A. rugosa<\/em> (Fisch.\n& C.A. Mey.) Kuntz) originates from East Asia7,8<\/sup>. Some\nAgastache<\/em> species are used in\ntraditional medicine as natural remedies against pain, bronchitis, hypertension,\nand gastrointestinal disorders 8,9<\/sup>.  The\nKorean mint (A. rugosa<\/em>) is the\nmost studied species of this genus regarding its chemical composition and biological\nactivity while other species of this genus (A. foeniculum <\/em>(Pursh)\nKuntze, <\/em>A. mexicana <\/em>(Kunth)\nLint & Epling,<\/em> etc.) have attracted much less attention of researchers in the area of\npharmacognosy8,9<\/sup>. The biological activities of Agastache<\/em> <\/em>species are\nrelated mainly to the valuable compounds of their essential oils 7,8,10,11<\/sup>. Such groups\nof valuable secondary metabolites  of the\nAgastache<\/em> representatives as polyphenols or\ntriterpenoids were investigated much less 7,8,12-15<\/sup>. <\/p>\n\n\n\n

This study\naimed to conduct the chromatographic analysis of polyphenols and determine the\ninfluence of extraction frequency on the efficiency of extracting\nhydroxycinnamic acids and flavonoids from raw material of anise hyssop (A. foeniculum) <\/em>under\nits cultivation in Ukraine. <\/strong><\/p>\n\n\n\n

Materials and Methods<\/strong><\/p>\n\n\n\n

Plant material <\/strong><\/p>\n\n\n\n

The aerial part of A. foeniculum<\/em> (the variety with white\nflowers) was harvested during the flowering period from the plots (Fig. 1, a<\/em>) in the Ternopil region (Ukraine). The collected flowering shoots were cut into pieces up to 15 cm long and dried at 25\u201335\u00b0C.\nDried raw materials (Fig. 1, b<\/em>) were\nsifted through a sieve with a hole diameter of 2.5 mm before the extraction.<\/p>\n\n\n\n

HPLC\nanalysis<\/strong><\/strong><\/p>\n\n\n\n

The\nchromatographic analysis of phenolic compounds was performed by the validated\nmethod of high-performance liquid chromatography (HPLC)16<\/sup> in 70% ethanol extracts of the ground\nraw material.  The triple extraction of\nraw materials was used. The raw material-solvent ratio was 1:10. The\nextractions were performed in an ultrasonic bath for 30 min each time (at 40\u00b0C). <\/p>\n\n\n\n

A\nShimadzu LC20 Prominence chromatograph with column Phenomenex Luna C18\n(250 mm\u00d74.6 mm with silica gel as sorbent) was used for HPLC analysis. The UV absorption spectra\nof the reference standards of polyphenols and the test samples were recorded in\nthe range of 190\u2013400 nm.\nThe gradient elution was carried out with two solvents: 1) 0.1% aqueous\nsolution of trifluoroacetic acid; 2) 0.1% solution of trifluoroacetic acid in\nacetonitrile17<\/sup>. The time of HPLC analysis was 60 min.\nThe HPLC analysis was carried out in triplicate and results were\nexpressed as mean value \u00b1 standard deviation.<\/p>\n\n\n\n\n\n
\"\"<\/td>\n\n

Figure 1<\/strong>:<\/strong> Appearance of\u00a0Agastache foeniculum<\/em> plants on the experimental plot (during flowering) (a) and dried raw\u00a0material (b).<\/strong><\/p>\n

\u00a0<\/p>\n

Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Results and Discussion<\/strong><\/p>\n\n\n\n

Several hydroxycinnamic acids\n(rosmarinic, ferulic, caffeic and chlorogenic) and flavonoids (apigenin, apigenin-7-O<\/em>-glucoside, hyperoside, quercitrin,\nrutin, and quercetin) were revealed in the A. foeniculum<\/em> herb by HPLC method (Table\n1, Fig. 2-4).<\/p>\n\n\n\n

It was established that the content of rosmarinic\nacid as the main identified\ndominant compound during the\nprimary, secondary and tertiary extraction of the A. foeniculum<\/em>\nraw material decreased in the\nfollowing order: 37.563>15.435>0.642 (mg\/g). Regarding the predominant\nflavonoids, the content of apigenin-7-O<\/em>-glucoside was 24.508>9.107>0.945\n(mg\/g) and apigenin 19.547>9.676>1.816 (mg\/g),\nrespectively. <\/p>\n\n\n\n

Table 1: The content of phenolic compounds in the Agastache foeniculum<\/em> herb (HPLC analysis)<\/strong><\/p>\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n
\n

Compound<\/strong><\/p>\n<\/td>\n

\n

Retention time, min<\/strong><\/p>\n<\/td>\n

\n

Content, mg\/g<\/strong><\/p>\n<\/td>\n<\/tr>\n

\n

First extraction<\/strong><\/p>\n<\/td>\n

\n

Second<\/strong><\/p>\n

extraction<\/strong><\/p>\n<\/td>\n

\n

Third extraction<\/strong><\/p>\n<\/td>\n<\/tr>\n

\n

Chlorogenic acid<\/p>\n<\/td>\n

\n

19.9<\/p>\n<\/td>\n

\n

2.124<\/p>\n<\/td>\n

\n

0.935<\/p>\n<\/td>\n

\n

0.096<\/p>\n<\/td>\n<\/tr>\n

\n

Caffeic acid<\/p>\n<\/td>\n

\n

22.3<\/p>\n<\/td>\n

\n

5.563<\/p>\n<\/td>\n

\n

2.872<\/p>\n<\/td>\n

\n

0.301<\/p>\n<\/td>\n<\/tr>\n

\n

Rutin<\/p>\n<\/td>\n

\n

31.5<\/p>\n<\/td>\n

\n

0.926<\/p>\n<\/td>\n

\n

0.319<\/p>\n<\/td>\n

\n

0.045<\/p>\n<\/td>\n<\/tr>\n

\n

Ferulic acid<\/p>\n<\/td>\n

\n

32.3<\/p>\n<\/td>\n

\n

1.296<\/p>\n<\/td>\n

\n

0.456<\/p>\n<\/td>\n

\n

0.060<\/p>\n<\/td>\n<\/tr>\n

\n

Hyperoside<\/p>\n<\/td>\n

\n

32.8<\/p>\n<\/td>\n

\n

9.713<\/p>\n<\/td>\n

\n

 5.483<\/p>\n<\/td>\n

\n

0.432<\/p>\n<\/td>\n<\/tr>\n

\n

Quercitrin<\/p>\n<\/td>\n

\n

34.9<\/p>\n<\/td>\n

\n

0.469<\/p>\n<\/td>\n

\n

0.128<\/p>\n<\/td>\n

\n

<0.01<\/p>\n<\/td>\n<\/tr>\n

\n

Rosmarinic acid<\/p>\n<\/td>\n

\n

37.8<\/p>\n<\/td>\n

\n

37.563<\/p>\n<\/td>\n

\n

15.435<\/p>\n<\/td>\n

\n

0.642<\/p>\n<\/td>\n<\/tr>\n

\n

Apigenin-7-O<\/em>-glucoside<\/p>\n<\/td>\n

\n

38.2<\/p>\n<\/td>\n

\n

24.508<\/p>\n<\/td>\n

\n

9.107<\/p>\n<\/td>\n

\n

0.846<\/p>\n<\/td>\n<\/tr>\n

\n

Quercetin<\/p>\n<\/td>\n

\n

46.6<\/p>\n<\/td>\n

\n

0.317<\/p>\n<\/td>\n

\n

0.143<\/p>\n<\/td>\n

\n

<0.01<\/p>\n<\/td>\n<\/tr>\n

\n

Apigenin<\/p>\n<\/td>\n

\n

52.4<\/p>\n<\/td>\n

\n

19.547<\/p>\n<\/td>\n

\n

9.676<\/p>\n<\/td>\n

\n

1.816<\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n\n\n\n
\"\"<\/td>\n\n

Figure 2: HPLC chromatogram of hydroxycinnamic acids and flavonoids<\/strong> in <\/strong>the A. foeniculum<\/em> herb after the first extraction (at 280 nm, 330 nm and 350 nm).<\/strong><\/p>\n

<\/p>\n

Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n\n
\"\"<\/td>\n\n

Figure 3: HPLC chromatogram of hydroxycinnamic acids and flavonoids<\/strong> in <\/strong>the A. foeniculum<\/em> herb after the second extraction (at 280 nm, 330 nm and 350 nm)<\/strong><\/p>\n

<\/p>\n

Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n\n
\"\"<\/td>\n\n

Figure 4: HPLC chromatogram of hydroxycinnamic acids and flavonoids<\/strong> in <\/strong>the A. foeniculum<\/em> herb after the third extraction (at 280 nm, 330 nm and 350 nm).<\/strong><\/p>\n

<\/p>\n

Click here to view Figure<\/a><\/p>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n

Thus, it was revealed that during the secondary extraction of A. foeniculum<\/em> raw material, a 2-3 times lower quantitative content of dominant polyphenols was extracted compared to the primary extraction. As for the tertiary extraction of plant raw materials, it was determined to be inefficient in terms of excessive time and solvent consumption because HPLC analysis showed that an order of magnitude less polyphenolic compounds are compared to primary extraction.<\/p>\n\n\n\n

Rosmarinic acid, the predominant component of the studied A. foeniculum<\/em> herb, possesses noticeable antioxidant, anti-inflammatory, antiviral, antimicrobial hepatoprotective, anti-nociceptive and immunomodulatory properties5,18-20<\/sup>. Apigenin and apigenin-7-O<\/em>-glucoside as other predominant compounds of the investigated raw material demonstrate the prominent antioxidant, anti-inflammatory and anticancer effects21,22<\/sup>. As it is known, among a wide range of exogenous antioxidants, polyphenols are one of the most effective classes of compounds possessing antioxidant properties .<\/p>\n\n\n\n

Numerous data of scientific literature regarding the polyphenolic profiles of the different Lamiaceae<\/em> species demonstrated that rosmarinic acid is quite often their common major compound14, 23-30<\/sup>. Thus, the ultra-performance liquid chromatography analysis of methanolic extracts from A. rugosa <\/em>roots revealed the predominance of rosmarinic acid among 24 identified polyphenols25<\/sup>. Its level was 3.82\u20139.16 mg\/g, depending on the used in vitro<\/em> culture system. The content of rosmarinic acid in the 70% ethanolic extract from A. foeniculum<\/em> herb grown in Romania fluctuated in the range of 6.45-8.12 mg\/g, depending on the harvesting period of the plant raw material26<\/sup>. The other study revealed that the content of rosmarinic acid in the ethanolic extract of Origanum vulgare<\/em> (Lamiaceae<\/em>) herb was 12.40 mg\/g27<\/sup>. Rosmarinic acid (21.42 mg\/g) was also the main predominant hydroxycinnamic acid of the Betonica peraucta<\/em> (Lamiaceae<\/em>) herb collected in Ukraine28<\/sup>. The experimental results showed that the content of rosmarinic acid in the aerial parts of several Lamiaceae<\/em> species from different genera collected in Ukraine was in the ranges of 12.61\u201324.83 mg\/g in the methanolic extracts obtained by maceration29,30<\/sup> which is consistent with our data regarding A. foeniculum<\/em> herb.<\/p>\n\n\n\n

The experimental studies demonstrated that the concentrations of\npolyphenols were higher in the methanolic extract of A. rugosa <\/em>compared\nto the ethanolic one24<\/sup>. The content of\nflavon genistein as the main predominant compound of A. rugosa was\n<\/em>3.17 mg\/g in methanolic extract and 2.23\nmg\/g in ethanolic extract which\nis much less than in the A. foeniculum<\/em>\nherb studied by us. Researchers found significant correlations between\nthe total phenolic contents and the antioxidant activity of the studied extracts.\n<\/p>\n\n\n\n

Recently, it was <\/strong>revealed by Korean researchers31<\/sup> the high bioactive potential of rosmarinic acid and flavons tilianin and acacetin as key phenolic compounds of A. rugosa<\/em> in humans and a Caco-2 cell model. Another validated bioanalytical method was developed <\/strong>for the simultaneous quantification of the dominated bioactive phenolic compounds (rosmarinic acid and flavons) from the A. rugosa aerial part<\/em> in human plasma using UHPLC-MS\/MS32<\/sup>. These clinical studies showed that the concentration of rosmarinic acid was the highest among other polyphenols in plasma when applied the dry extract <\/em>obtained from theA. rugosa<\/em> aerial part with 50 % ethanol. This technique offered the precise, accurate, and repeatable method for analyzing A. rugosa<\/em> biocompounds in human plasma samples and detecting the analytes at very low concentrations (the lower limit of quantitation for both tilianin and rosmarinic acid was 0.5 ng\/mL and 0.1 ng\/mL for acacetin). The anti-inflammatory effects of flavones and two phenylpropanoid glucosides isolated from the A. rugosa aerial <\/em>part were demonstrated in the in vitro <\/em>studies using macrophages33<\/sup>.<\/p>\n\n\n\n

Conclusion<\/strong><\/p>\n\n\n\n

The contents of\nhydroxycinnamic acids and flavonoids under the influence of triple extraction of the A. foeniculum<\/em> herb were revealed using HPLC analysis. The\nmain polyphenolic compounds in the A.\nfoeniculum<\/em> raw material during all stages of\nextraction were rosmarinic acid, apigenin-7-O<\/em>-glucoside and apigenin. It was concluded\nthat the third extraction was inefficient\nin terms of low content of polyphenols as well as excessive analysis time and solvent costs compared to the first and second\nextractions.<\/p>\n\n\n\n

Acknowledgement<\/strong><\/p>\n\n\n\n

None to declare<\/p>\n\n\n\n

Conflict of Interests<\/strong><\/p>\n\n\n\n

There were no commercial or financial links that may be deemed a potential conflict of interest during the research.<\/p>\n\n\n\n

 Funding Sources<\/strong><\/p>\n\n\n\n

The author(s) received no financial support for the research.<\/p>\n\n\n\n

References<\/strong><\/p>\n\n\n\n

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