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Article

Siberian Tarragon: A Promising Source of Flavone O-Glycosides and Methylated Flavanone Aglycones in North Asian Accessions of Artemisia dracunculus

by
Daniil N. Olennikov
1,*,
Nina I. Kashchenko
1 and
Nadezhda K. Chirikova
2
1
Laboratory of Biomedical Research, Institute of General and Experimental Biology, Siberian Division, Russian Academy of Science, 6 Sakhyanovoy Street, 670047 Ulan-Ude, Russia
2
Department of Biochemistry and Biotechnology, North-Eastern Federal University, 58 Belinsky Street, 677027 Yakutsk, Russia
*
Author to whom correspondence should be addressed.
Horticulturae 2025, 11(11), 1393; https://doi.org/10.3390/horticulturae11111393
Submission received: 18 October 2025 / Revised: 15 November 2025 / Accepted: 16 November 2025 / Published: 18 November 2025
(This article belongs to the Special Issue Advances in Phytochemical Properties and Bioactive Compounds of Horticultural Crops)
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Abstract

Artemisia dracunculus L., commonly known as tarragon, is a popular culinary herb and a valuable source of bioactive extracts and phytocompounds. Its wide distribution across regions of the Northern Hemisphere demonstrates the species’ high adaptability to diverse growing conditions and has led to the development of chemoraces that differ in chemical composition. North Asian populations of A. dracunculus remain poorly studied, and plants growing in Siberia have not yet been examined. Given the vast areas occupied by tarragon, the species is a promising candidate for industrial use. Liquid chromatography–mass spectrometry (LC–MS) profiling identified 80 compounds in Siberian tarragon samples, including hydroxycinnamates (HCys), coumarins, flavonoid aglycones (FlAs), and glycosides (FlGs). Among these, 62 phenolics were reported for the first time as A. dracunculus metabolites, highlighting the uniqueness of the North Asian accessions, particularly in their diversity of flavone O-glycosides and methylated flavanone aglycones. The highest levels of HCy, FlA, and FlG were 21.84, 52.53, and 54.44 mg/g, respectively, yielding a total phenolic content of 128.81 mg/g in the dry plant material—a high value. The concentrations of certain compounds exceeded 1%, making tarragon a noteworthy source of rare metabolites, including naringenin 7-O-methyl ester, thermopsoside, tilianin, and naringenin 7,4′-di-O-methyl ester. Thus, the existing knowledge of the chemical profile of tarragon has been expanded by new data on phenolic compounds from the North Asian populations of the species, which may be used to develop new A. dracunculus varieties with improved metabolic profiles and bioactive properties.

1. Introduction

Cultivated plants form the basis of the modern human diet, and their species diversity is estimated to include up to 35,000 botanical species [1]. The existing variability of utilized species is continually enriched through selection research and the exploration of new variants within known species [2]. The expansion of plant diversity primarily occurs in the fields of food and horticultural crops, driven by the growing human demand for a varied diet [3]. Intraspecific changes can influence not only morphological traits such as size, shape, and color but also chemical composition, thereby leading to variations in aroma, flavor, and functional properties owing to differences in the presence or absence of bioactive compounds [4].
Among the vast number of horticultural crops, tarragon (Artemisia dracunculus L.) holds high value as an aromatic, tea, and medicinal plant, exhibiting considerable variation in chemical composition depending on the location of collection or cultivation [5]. The most extensively studied component of the tarragon metabolome is its essential oil, whose main constituents vary across different geographic regions. Estragole predominates in A. dracunculus essential oils from France [6] and Georgia [5], while methyleugenol is dominant in samples from Canada [7], Denmark [5], and Cuba [8]. Additionally, terpinolene-containing cultivars have been identified in the United States [5], and ocimene/anethole chemotypes have been reported in Iran [9] and Italy [10]. Such variability in chemical composition is also characteristic of other groups of compounds in tarragon.
Data on the phenolic compounds of A. dracunculus reveal a highly diverse set of findings that cannot be explained only by geographical or environmental factors. Historically, studies on the chemical composition of tarragon have primarily focused on cultivated samples, while information on phenolic compounds in wild plants remains scarce. Phenolic constituents, represented by simple coumarins, were first identified in A. dracunculus in German cultivars in the late 1960s [11]. Over the subsequent six decades of research, approximately 100 phenolic compounds of various structural types have been identified in this species (Table 1) [11,12,13,14,15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43]. The geographical origin of A. dracunculus provides data on the phenolic composition of samples from Europe, three regions of Asia, North America, and North Africa.
The A. dracunculus populations of East Siberia are located near those of West Siberia and East Asia, suggesting potential mixing of chemical traits and the existence of plants exhibiting at least four possible chemical profiles: (1) a West Siberian type dominated by isocoumarins, (2) a Mongolian type containing phenolic glucosides, cinnamic acids, and lignans, (3) a mixed type with intermediate chemical markers, and (4) a distinct new type.
The total area of Eastern Siberia exceeds 4.6 million km2, and A. dracunculus is distributed throughout this territory. Accordingly, the preliminary estimate of the exploitable reserve may reach 100,000 tons per year. Such assessments highlight the importance of plants with such abundant natural reserves and underscore the need for studies to clarify the chemical profile of this potential medicinal species.
In this study, the LC–MS profile of Siberian tarragon from natural populations was investigated for the first time, with particular focus on flavonoid components. Additionally, the quantitative content of individual compounds and groups of phenolic compounds in the A. dracunculus herb was determined.

2. Materials and Methods

2.1. Plant Material

Tarragon (Artemisia dracunculus L.) samples were primarily collected in the Mukhorshibirsky District of the Republic of Buryatia (East Siberia, Russia; sites No. 5–65; Figure 1) and partially in the Petrovsk-Zabaikalsky District of Zabaikalsky Krai (sites No. 1–4). Professor T.A. Aseeva, Doctor of Pharmacy (IGEB SB RAS, Ulan-Ude, Russia) authenticated the species. At each site (No. 1–65), 100 samples representing the entire aboveground portion of the plant were collected and dried in a convection oven at 40 °C to a moisture content below 5% and then grouped into sets of 20 plants. This resulted in five samples per site, yielding a total of 325 experimental samples from 6500 individual plants. Sampling was performed during a sunny, precipitation-free period over five consecutive days in 1–5 July 2024. Preliminary studies in 2023 demonstrated that collection times between 10:00 and 18:00 did not affect the plant’s chromatographic profile, establishing this time window as the standard for sampling.

2.2. Sample Preparation

Ground plant material (100 mg, 0.125 mm particle size) was extracted twice with 10 mL of methanol by sonication in a VBS-27DP ultrasonic bath (Vilitek, Moscow, Russia) for 15 min (40 °C, 500 W, 50 kHz), followed by centrifugation in a CM-09M Fugamix centrifuge (Elmi, Riga, Latvia) at 9000× g for 10 min and filtration through 0.22 μm syringe filters into a 25 mL volumetric flask. The volume was adjusted to 25 mL with methanol. Extracts were analyzed immediately after preparation, following the addition of two internal standards: dracocephoside I (final concentration 5 μg/mL) and arcapillin 4′-O-acetate (final concentration 2 μg/mL). All chemicals used were analytical grade and were purchased from Advanced ChemBlocks (Hayward, CA, USA), BioCrick (Chengdu, China), ChemFaces (Wuhan, China), Carl Roth (Karlsruhe, Germany), Cymit Qyimica (Barselona, Spain), Extrasynthese (Lyon, France), LGC Standards (Beijing, China), MedChemExpress (Monmouth Junction, NJ, USA), Push BioTechnologies (Chengdu, China), SigmaAldrich (St. Louis, MO, USA), and Synthose (Concord, ON, Canada).

2.3. High-Performance Liquid Chromatography with Photodiode Array and Ion Trap–Time-of-Flight Mass Spectrometric Detection (HPLC-PDA-IT-TOF-MS)

Chromatographic analysis was performed using an LC-20 Prominence liquid chromatograph (Shimadzu, Columbia, SC, USA) coupled to an SPD-30AM photodiode array detector (PDA; Shimadzu) and an LCMS-9050 ion trap–time-of-flight (IT–TOF) mass spectrometer system (Shimadzu). Separation was achieved on a Gold-Turbo Basic C18 column (75 mm × 3 mm, 1.8 μm; Dr. Maisch GmbH, Ammerbuch, Germany) using 0.1% formic acid in water (mobile phase A) and 0.1% formic acid in acetonitrile (mobile phase B). The following gradient program was applied: 0–1 min, 2–11% B; 1–9 min, 11–24% B; 9–17 min, 24–32% B; 17–35 min, 32–76% B; and 35–45 min, 76–2% B. The injected volume, flow rate, and column temperature were 1 µL, 1 mL/min, and 25 °C, respectively. UV spectra were recorded from 200 to 600 nm, and mass spectra were acquired in negative ionization mode with a mass scan range of m/z 100–1900. The MS interface parameters were as follows: interface temperature 300 °C, desolvation line temperature 250 °C, heating block temperature 400 °C, nebulizer gas (N2) flow 3 L/min, heater gas (air) flow 10 L/min, collision-induced dissociation (CID) gas (Ar) pressure 270 kPa, argon flow 0.3 mL/min, and capillary voltage 3 kV. Metabolite identification was based on retention time, ultraviolet spectra, and mass spectra. It was compared with reference standards, laboratory collections, and literature data using LabSolution CS 2.0 workstation software (Shimadzu) and an internal LC–MS library. Quantification of compounds 1–80 was performed using MS peak area data after calibration curve preparation. Calibration curves were constructed from a series of reference substance dilutions (1–100 μg/mL, three replicates per dilution), plotting concentration (µg/mL) versus peak area using the Advanced Grapher 2.2 software package (Alentum Software, Inc., Ramat Gan, Israel) (Table S1).

2.4. Statistical Analysis

Statistical analyses were performed using one-way analysis of variance (ANOVA) in Statistica software (ver. 12.6, Dell, Dell City, TX, USA), with mean differences evaluated by Fisher’s least significant difference (LSD) test at α = 0.05. Statistical significance was defined as p < 0.05. Results are presented as means ± standard deviation (S.D.). Linear regression analyses and calibration curve construction were performed using Advanced Grapher 2.2 (Alentum Software, Inc., Ramat Gan, Israel).

3. Results and Discussion

The Eastern Siberian tarragon population represents the largest cluster of A. dracunculus in the Republic of Buryatia. This population is continuous, extending nearly 100 km, primarily in the Mukhorshibirsky District, with its eastern boundary reaching into Zabaikalsky Krai. Sixty-five sites were selected in this population for plant sampling. This sampling strategy was used to assess the frequency of compounds in the A. dracunculus herb and to evaluate the stability of its chemical profile across the entire population.

3.1. LC-MS Profiling of Phenolic Compounds in A. dracunculus from Siberian Accessions

A total of 80 compounds were detected and characterized in A. dracunculus herb samples (No. 1–65), including 12 tentatively identified phenolic compounds based on comparison of retention times, UV spectra, and mass spectral data with literature reports [44,45,46,47,48,49,50,51,52,53,54,55,56,57] (Figure 2, Table 2 and Table S2). Identified compounds comprised hydroxycinnamates (HCys), coumarins, and flavonoids, including flavone and flavanone aglycones as well as their glycosides.

3.1.1. Hydroxycinnamates

Twenty-one compounds were reliably identified as derivatives of caffeic and ferulic acids; notably, caffeic acid (23) itself was detected, whereas ferulic acid was not. The caffeates were classified into three groups: esters with quinic acid, glucose, and tartaric acid. Caffeoylquinates included mono-substituted forms—1-O- (1), 3-O- (19), 4-O- (10), and 5-O-caffeoylquinic acid (18, 22)—and disubstituted forms—1,4-di-O- (12), 1,5-di-O- (33), 3,4-di-O- (37), 3,5-di-O- (38), and 4,5-di-O-caffeoylquinic acid (40). Compound 3 was identified as cis-caffeoylquinic acid based on its UV spectrum and was most likely the 1-O-isomer, as indicated by its low retention time. Among the five caffeoyl glucoses, 1-O-caffeoyl β-glucose (11) was confirmed, while four isomers (2, 4, 7, and 14) exhibiting a caffeic acid-like UV spectrum and identical MS pattern (m/z 341, 179) were tentatively assigned as 3-O-, 2-O-, 4-O-, and 6-O-caffeoyl glucose, respectively [44]. Two caffeoyl-tartaric acids were identified as trans-caftaric acid (5) and cis-caftaric acid (8). Although caffeates have been previously reported in A. dracunculus herb, information was limited to seven compounds: caffeic acid in samples from Greece [16], Iran [26], and China [37]; 4-O-, 5-O-, 3,4-di-O-, 3,5-di-O-, and 4,5-di-O-caffeoylquinic acids in samples from Portugal [19,20], Romania [21], and Iran [26]; and caftaric acid [19]. Compounds 1, 3, 8, 11, 12, 19, 22, and 33 were detected in A. dracunculus for the first time.
Ferulates in A. dracunculus included two mono-feruloylquinic acids (4-O-, 28; 5-O-, 30) and four feruloyl β-glucoses (1-O-, 13; 2-O-, 6; 4-O-, 9; 6-O-, 15); except compound 30 [21], all were newly reported in the species. Two mixed cinnamoylquinic acids—3-O-feruloyl-4-O-caffeoylquinic acid (46) and 3-O-feruloyl-5-O-caffeoylquinic acid (47)—were also detected as components of A. dracunculus.
Ferulic acid itself has been previously reported at least five times [16,18,19,20,26], together with 3-O- [22] and 5-O-feruloylquinic acids [21], as well as 4-O-feruloyl-5-O-caffeoylquinic acid [21], indicating that ferulates are common constituents of tarragon. Of the twenty-seven cinnamates identified in this study, only eight had been previously reported. In North Asian populations, several metabolites, including p-coumaric acid [20,26], coumaroylquinic acids [17], 1,3,5-tri-O-caffeoylquinic acid [19], and p-hydroxyphenylethyl-O-glucoside 6′-O-caffeate [36], were not detected, highlighting substantial variations in the diversity of A. dracunculus cinnamates across geographic regions.

3.1.2. Coumarins

Two coumarins, scopoletin 7-O-glucoside (scopoline, 17) and umbelliferone 7-O-glucoside (skimmin, 20), were detected in A. dracunculus samples and reported for the first time in this species. This is unusual because the plant is generally known to accumulate coumarins, including coumarin [26], herniarin [11,13,14,15,26,28,31,43], scoparone [11,13,14,15,31,36,38], scopoletin [11,13,14,15], fraxidin, and isofraxidin [22]. Interestingly, no isocoumarins were observed in any of the 65 sampled sites, suggesting the presence of a unique non-iso/coumarin chemotype of A. dracunculus in this population.

3.1.3. Flavone Aglycones and Glycosides

Twenty-three flavones of the apigenin and luteolin series were detected in both aglycone and glycoside forms. Flavone aglycones included apigenin (api) derivatives, such as acacetin (api 4′-O-methyl ester, 74), and luteolin (lut) derivatives, including chrysoeriol (lut 3′-O-methyl ester, 66), diosmetin (lut 4′-O-methyl ester, 62), lut 7,4′-di-O-methyl ester (68), and lut 7,3′,4′-tri-O-methyl ester (72). Although apigenin [26,37] and luteolin [16,22,26,29,30,37] have been previously reported as components of tarragon, only their methylated derivatives were detected in the samples analyzed in this study.
The remaining 18 compounds were various O- and C-glycosides, with or without acylation of the glycosidic moiety. Apigenin derivatives included glucuronides at the 7-O- (44) and 4′-O-positions (48), as well as glucose at the 6-C- (24), 8-C- (27), and 6,8-di-C-positions (21). Acacetin (41) was also detected. Luteolin glucosides included 5-O- (34), 7-O- (34), and 4′-O-glycosides (36), as well as three acylated derivatives of cynaroside: luteolin 7-O-(6′-O-acetyl)-glucoside (52) [51], luteolin 7-O-(2″,6″-di-O-malonyl)-glucoside (anthriscoside C, 53) [52], and luteolin 7-O-(3″,6″-di-O-acetyl)-glucoside (56) [55]. Additionally, chrysoeriol 7-O-glycoside (thermopsoside, 35) and its two acetates (55 and 57), together with three rare diosmetin glucuronides (7-O-, 42; 3′-O-, 45; and 7,3′-di-O-, 31), were also identified in A. dracunculus.
Of the compounds described above, only two have previously been reported as constituents of tarragon: vicenin-2 (21), found in a Polish sample [18], and cynaroside, detected in samples from Portugal [19] and Crimea [17]. Thus, 21 of the identified compounds represent novel discoveries in the A. dracunculus herb. Known tarragon glycosides, including luteolin 7-neohesperidoside [17], apigenin-glucosyl-arabinoside, apigenin-arabinosyl-glucoside [21], and estragonoside [23,24], were not detected in the Siberian accessions of A. dracunculus.

3.1.4. Flavanone Aglycones and Glycosides

Twenty-five flavanones in A. dracunculus were based on four aglycones: pinocembrin, naringenin, eriodictyol, and homoeriodictyol. Free pinocembrin (71) and its 7-O-glucoside (49) have previously been reported in tarragon cv. Gribovskii [23,24], supporting their detection in Asian samples. However, four additional pinocembrin derivatives are reported here for the first time in tarragon: pinocembrin 7-O-glucuronide (51) and three lipophilic aglycones—pinocembrin 5-O-methyl ester (73), pinocembrin 7-O-methyl ester (77), and pinocembrin 5,7-di-O-methyl ester (80).
Naringenin derivatives previously reported in A. dracunculus include free naringenin (59) [26,36,37,38] and its 7-O-methyl ester, sakuranetin (60) [31,40,41,42]. These compounds were also identified in this study, along with novel tarragon flavonoids: naringenin 4′-O-methyl ester (isosakuranetin, 69), 5,7-di-O-methyl ester (61), 7,4′-di-O-methyl ester (70), and 5,7,4′-tri-O-methyl ester (79). Naringenin glycosides were not detected, although naringenin-O-hexoside has been previously reported in Portuguese A. dracunculus [19].
Eriodictyol (50), four of its glycosides, and six methylated esters were identified in Siberian A. dracunculus samples. One glycoside was confirmed as eriodictyol 7-O-glucoside (26), while compounds 25, 32, and 39, exhibiting a flavanone UV pattern and a deprotonated molecular ion at m/z 449 that yielded a daughter ion at m/z 287 after dehexosylation, were assigned as eriodictyol O-hexoside isomers of 26. Considering that eriodictyol has only four known glucosides and taking into account chromatographic behavior, compound 25, with a shorter retention time (tR 13.17 min), is likely the 5-O-glucoside because glycosylation at the 5-O-position increases polarity [61]. Compounds 32 and 39 most likely have substitutions at the 3′-O- or 4′-O-positions on ring B of eriodictyol [62]. Monomethyl esters sternbin (7-O-methyl, 58) and hesperetin (4′-O-methyl, 64) were detected, along with compound 54, which exhibited a flavanone UV pattern, a molecular ion at m/z 301, and an MS2 fragment at m/z 287, similar to 58 and 64. Based on its retention time (tR 23.08 min), which is shorter than that of 58 (tR 23.99 min) and 64 (tR 25.97 min), compound 54 is most likely eriodictyol 5-O-methyl ester, a known cytotoxic agent [53] not previously reported in the Artemisia genus. Additionally, two dimethyl-eriodictyols with substitutions at 7,3′- (75) and 7,4′-positions (65), as well as 7,3′,4′-trimethyl-eriodictyol (78), were identified using reference standards. Compound 76, exhibiting a flavanone UV pattern, showed a molecular ion at m/z 329 and MS2 fragments at m/z 315, 301, and 287, similar to compound 78, suggesting it is an eriodictyol trimethyl ester. Of the four possible isomers, the position of one (78) has been determined, allowing compound 76 to be assigned as either the 5,7,3′-, 5,7,4′-, or 5,3′,4′-tri-O-methyl ester of eriodictyol. None of these three isomers have been previously reported in A. dracunculus. Known eriodictyol metabolites in tarragon include the 7-O-methyl ester [24], 4′-O-methyl ester [22], 7,3′-di-O-methyl ester [24], and 7,4′-di-O-methyl ester [21,22], but these data indicate that the composition of eriodictyol derivatives in the plant is considerably richer than previously reported.
Homoeriodictyol, or 3′-methyleriodictyol, was detected in A. dracunculus as a 7-O-glycoside (43), a compound not previously reported in the genus Artemisia.

3.1.5. Various Flavonoids

Compound 16 was identified as a quercetin glucoside based on its UV spectrum and aglycone ion at m/z 301. Analysis of sequential fragment losses from the molecular ion revealed detachment of a hexose (m/z 639 → 477) followed by a hexuronic acid (m/z 477 → 301), indicating a hexosyl-hexuronide structure of the carbohydrate moiety, similar to nelumboside, a quercetin 3-O-glucosyl-glucuronide from Nelumbo nucifera [49]. This was the only quercetin derivative detected across all A. dracunculus samples studied. Notably, the absence of other quercetin derivatives is unusual because the most commonly reported flavonol in tarragon is rutin (quercetin 3-O-rutinoside) [12,16,17,19,21,22,27,28,29,30,37], as well as quercetin itself [12,16,22,26,29,30,37].
Two flavanols, pinobanksin (63) and its 5-O-methyl ester (67), were detected for the first time in A. dracunculus and the genus Artemisia.

3.1.6. Occurrence of Compounds in A. dracunculus Population

The detected compounds exhibited high incidence across samples from different collection sites (Table 2). Of the 80 compounds identified, 45 (56.3%) were present in all samples (100% incidence), 22 compounds (27.5%) occurred in 90–<100% of samples, 10 compounds (12.5%) in 80–<90%, and 3 compounds (3.7%) in <80%. The rarest phenolics were caffeoylquinic acid 3, O-caffeoyl glucose 4, and caftaric acid, each detected in 76.9–78.4% of the samples. The high overall incidence of compounds indicates that the studied A. dracunculus population possesses a similar chemical profile.

3.2. Comparison of Global and Siberian Populations of A. dracunculus

A comparative analysis of previous reports and this study demonstrates that the Siberian tarragon population exhibits a distinct composition of phenolic compounds (Table 3).
The largest amount of phytochemical data currently available for A. dracunculus pertains to European populations, all of which represent cultivated plants. Benzoic acids, cinnamic acids, and cinnamoylquinic acids are commonly found in this species. In the benzoate group, protocatechuic acid [20] and its derivatives [17,18], gentisic acid [16,22], syringic acid [18], and α-resorcylic acid [21] have been identified. Various cinnamates have also been detected, both as free acids—such as p-coumaric acid [20], caffeic acid [16], and ferulic acid [16,19,20]—and as depsides with quinic acid (4-CQA [19], 5-CQA [16,19,20,21], 3,4-DCQA [19], 3,5-DCQA [21], 4,5-DCQA [19,21], 1,3,5-TCQA [19], 3-FQA [21], 5-FQA [21], coumaroylquinic acids [17], and 4-O-feruloyl-5-O-caffeoylquinic acid [21]) and tartaric acid (caftaric acid [19]) in numerous European samples.
The most common group of flavonoids in A. dracunculus comprises flavonol glycosides, including derivatives of quercetin (rutin, quercetin 3-O-robinoside, isoquercitrin, quercitrin, and hyperoside) [12,16,17,18,19,21,22], kaempferol (nicotiflorin) [17], isorhamnetin (narcissin) [18,19], and patuletin (patuletin 3-O-rutinoside, patuletin 3-O-robinoside, and patulitrin) [12,18], identified in cultivars from France [12], Greece [16], Italy [17], Poland [18], Portugal [19], Romania [21], and Russia [22]. Flavones of the luteolin (cynaroside [19,22], scolimoside [17]) and apigenin series (vicenin-2 [18], apigenin-glucosyl-arabinoside, and apigenin-arabinosyl-glucoside [21]) frequently accompany flavonols among A. dracunculus flavonoids. Flavanone glycosides have been reported in Portuguese samples (naringenin-O-hexoside) [30] and Russian samples (pinocembrin 7-O-glucoside) [23,24].
Coumarins have been reported in A. dracunculus cultivated in Germany (herniarin, scopoletin, and scoparone) [11] and Russia (fraxidin and isofraxidin) [22]. Isocoumarins, including capillarin and its derivatives, artemidinol, and related compounds, have been identified in samples from Würzburg [11,13,14,15] and Vienna [25].
A variety of lipophilic flavonoid aglycones (FlAs) have also been detected in leaf exudates and total extracts, including flavonols (kaempferol [16], quercetin [12,16,17,22], isorhamnetin [22], 6,7,4′-trimethoxy-galetin, 6,7,3′,4′-tetramethoxy-quercetagetin [21], eupatolitin, chrysosplenol D, and casticin [22]), flavones (luteolin [16,22], apigenin [16], cirsilineol [22], and annagenin [23,24]), and flavanones (sakuranetin [18], pinocembrin, and naringenin [23,24]).
Rare components identified in A. dracunculus include the flavone estragonoside (Russia, cv. Gribovskii) [23], the chalcones davidigenin and 2′,4′-dihydroxy-4-methoxydihydrochalcone (Poland) [18], the stilbene resveratrol (Portugal) [20], and the lignan medioresinol-O-hexoside (Portugal) [19], each reported only once and considered atypical for the genus. Additionally, two isocoumarins—artemidin and dracumerin—have been described in a West Siberian (Novosibirsk) specimen of A. dracunculus [14].
West Asian (Iran and Turkey) populations of A. dracunculus have demonstrated the accumulation of flavonol glycosides—rutin [27,28] and quercitrin [27]—as well as coumarins such as herniarin [26,28] and unsubstituted coumarin [28]. In twelve Iranian accessions of A. dracunculus, benzoic acids (syringic acid and vanillic acid), cinnamic acids (p-coumaric acid, caffeic acid, and ferulic acid), caffeoylquinic acids (5-CQA), and four lipophilic aglycones—naringenin, luteolin, apigenin, and quercetin—were identified and quantified [28]. The Turkish sample contained two unique phenylpropanoids, 4-(1′,1′,2′,2′-tetramethylpropyl)-1,2-benzenediol and 3-(p-methoxyphenyl)-1,2-propanediol, which have been reported only in this population [28].
Four flavonol glycosides were isolated from wild Central Asian (Kazakhstan) A. dracunculus, identified as rutin, bioquercetin, hyperoside, and isorhamnetin 7-O-(p-hydroxybenzoyl)-galactoside, along with three lipophilic aglycones (kaempferol, quercetin, and luteolin) [29,30]. In wild A. dracunculus from Kyrgyzstan, coumarins (herniarin and scoparone), isocoumarins (dracumerin and artemidin), and three methylated flavanones—naringenin 7-O-methyl ester, eriodictyol 7-O-methyl ester, and eriodyctiol 7,3′-di-O-methyl ester—were detected in plant organs [31]. Similar findings were reported for Uzbek samples of A. dracunculus, which were rich in isocoumarins, including artemidin, artemidinal, artemidiol [32,33,34,35], 2′-methoxydihydroartemidin, (-)-(R,S)-epoxyartemidin, and (+)-(R)-(E)-3′-hydroxyartemidin [14]. These results indicate that A. dracunculus from Kyrgyzstan [31] and Uzbekistan [14,32,33,34,35] represent a distinct chemotype characterized by a propensity to accumulate isocoumarins.
Despite their geographical proximity, the phenolic profiles of two East Asian A. dracunculus populations differed considerably. The Mongolian sample uniquely contained eugenol 4-O-glucoside, two lignans, and p-hydroxyphenylethyl-O-glucoside 6′-O-caffeate [36], which are atypical for the genus Artemisia. However, the presence of the isocoumarin capillarin and lipophilic flavanone aglycones (naringenin, eriodictyol, and hesperetin) suggests a biochemical affinity with other Asian populations [14,31]. In Chinese A. dracunculus, detected phenolic groups included benzaldehydes, benzoic acids, cinnamic acids, catechins, flavonol glycosides, and chalcones, with quantitative predominance of protocatechuic acid, rutin, isoquercitrin, and astragalin [37]. Lipophilic aglycones comprised flavonols (kaempferol, quercetin, and isorhamnetin), flavones (luteolin and apigenin), flavanones (naringenin), and flavanonols (taxifolin and aromadendrin). These findings indicate that Chinese specimens share chemical similarities with plants from Iran [26].
North American A. dracunculus was rich in scoparone and capillarin [36,38], as well as various chalcones, including 4-O-methyldavidigenin, 4′-O-methyldavidigenin, 2′,4′-dihydroxy-4-methoxydihydrochalcone, 2′,4′-dihydroxy-4′-methoxydihydrochalcone [40,41], and davidigenin [42]. The species also contained a series of lipophilic aglycones, with flavanones such as sakuranetin [40,41,42], naringenin, and eriodyctiol 7,4′-di-O-methyl ester [21,22] predominating, along with dihydroflavonols including aromadendrin 7-O-methyl ester and taxifolin 7,3′-di-O-methyl ester [36,38]. The presence of chalcones in A. dracunculus has been reported only in Canadian and American populations. Two caffeoylquinic acids (5-CQA and 4,5-DQCA) have been identified in U.S. A. dracunculus [42].
The Moroccan sample of A. dracunculus contained herniarin [43], which has also been detected in raw materials from other countries.
None of the populations from six other global regions displayed a similar chemical profile. The key conclusion is that Siberian tarragon is characterized by the presence of cinnamic acids, cinnamoylquinic acids, flavone and flavanone glycosides, and a series of FlAs, including flavones, flavanones, and their methoxylated derivatives. Coumarins commonly found in European [11,13,14,15,22], West Asian [26,28], Central Asian [31], North American [36,38], and North African [43] accessions were present only at trace levels in Siberian tarragon, as were flavonol glycosides previously reported in Europe [12,16,17,19,21], West Asia [27,28], Central Asia [29,30], and East Asia [37]. Siberian A. dracunculus samples appear unable to accumulate phenols, benzaldehydes, benzoic acids, isocoumarins, catechins, chalcones, lignans, stilbenes, and certain lipophilic aglycone types. Of the 80 compounds detected in this study, only 18 had been previously reported in tarragon, while 62 were identified for the first time in the species. It may be reasonable to consider the existence of a distinct subspecies or variation of A. dracunculus, which could account for the observed characteristics.

3.3. Phenolic Compound Content in A. dracunculus from Siberian Accessions

Analysis of the quantitative content of compound groups in Siberian A. dracunculus (Table S3) revealed that FlGs, FlAs, and HCys were the most abundant, with ranges of 48.29–54.44 mg/g, 43.06–52.53 mg/g, and 17.61–21.84 mg/g, respectively, resulting in a total phenolic content (TPC) of 109.61–128.81 mg/g in tarragon herb (Table 4). Previous reports indicate lower TPC values in A. dracunculus from China (5.67 mg/g) [1], Italy (<10 mg/g) [17], Romania (14.57 mg/g) [21], Portugal (25.05–45.27 mg/g, in extracts) [19], and Iran (40.91–96.52 mg/g, in extracts) [26]. Coumarins, flavonol glucosides, and flavonol methyl esters were present only at trace levels.
Among FlGs, chrysoeriol derivatives were the most abundant (15.02–16.04 mg/g), largely owing to chrysoeriol 7-O-glucoside, followed by acacetin derivatives (14.21–15.98 mg/g), primarily reflecting acacetin 7-O-glucoside content. Diosmetin glucosides (7.08–8.63 mg/g) and luteolin glucosides (6.83–8.17 mg/g) were present at lower levels, although individual compounds such as diosmetin 7-O-glucuronide (6.32–7.82 mg/g) and luteolin 7-O-glucoside (5.83–6.82 mg/g) remained relatively abundant.
Concentrations of apigenin glycosides, as well as glycosides of pinocembrin, eriodictyol, and homoeriodictyol, did not exceed 3 mg/g. The total FlG content in A. dracunculus herb ranged from 48.29 to 54.44 mg/g, with FlGs accounting for the majority (45.53–50.65 mg/g). According to available data, luteolin 7-O-glucoside accumulated up to 1.09 mg/g [19], naringenin O-hexoside up to 0.21 mg/g [19], and two apigenin O-di-glycosides up to 0.23 mg/g (combined) [21] in A. dracunculus herb, which is substantially lower than the levels observed in Siberian material.
Regarding FlAs, flavones in this group of A. dracunculus phenolics were present at low levels (<0.01–0.07 mg/g), whereas flavanone derivatives accumulated at much higher concentrations, reaching 43.06–52.53 mg/g. Within the nonmethylated flavanone group, 82.4–89.5% of the aglycones were naringenin (7.01–8.96 mg/g), representing an exceptionally high accumulation compared with previously reported levels in A. dracunculus from Iran (0–0.06 mg/g) [26] and China (0.006 mg/g) [37]. It has previously been established that high levels of free naringenin are characteristic of Citrus species, reaching up to 3.4 mg/g [63], which is considerably lower than those found in Siberian tarragon. The quantitative distribution of methylated flavanone aglycones was dominated by naringenin derivatives, including naringenin 7-O-methyl ester (sakuranetin; 14.63–16.94 mg/g DW, ~38–42% of total methylated flavanones), naringenin 7,4′-di-O-methyl ester (10.08–12.52 mg/g, ~28–32%), naringenin 4′-O-methyl ester (isosakuranetin; 5.11–7.25 mg/g, ~14–18%), and naringenin 5,7-di-O-methyl ester (4.30–5.26 mg/g, ~12%). The remaining methylated aglycones accounted for 1.4–3.2% of the total group content. Previously reported total levels of lipophilic aglycones in A. dracunculus ranged from 0.1 to 5.69 mg/g [21,23,24,26,37], indicating that the maximum previously known level was 9.2 times lower than that observed in this study.
The majority of HCys in A. dracunculus was contributed by hydroxycinnamoyl-quinic acids (17.32–21.06 mg/g), with caffeoyl-quinic acids predominating (14.86–17.98 mg/g), including monocaffeoyl-quinic acids (2.54–3.76 mg/g) and dicaffeoyl-quinic acids (12.32–14.51 mg/g). Overall, these data are consistent with typical species characteristics because HCys content in A. dracunculus has been reported to range from 0.37 mg/g in samples from Iran [26] to 31.56 mg/g in plants from Portugal [19].

3.4. Recommendations and Future Perspectives

The data on the chemical profile and quantitative content of phenolic compounds in A. dracunculus herb clearly highlight the uniqueness of the Siberian population, which holds potential for practical applications. To realize this potential, it is necessary to investigate the cultivation of this particular A. dracunculus variety under controlled open-field conditions to obtain raw materials with a constant composition, while assessing productivity and other agronomic parameters. Because tarragon has numerous varieties that are successfully cultivated, achieving this goal appears feasible in the near future.
Further genetic studies will enable a reliable determination of whether Siberian tarragon represents a distinct species or a variety/subspecies of A. dracunculus. This possibility is supported by the fact that modern A. dracunculus comprises five varieties—var. changaica (Krasch.) Y.R.Ling, var. dracunculus, var. pamirica (C.Winkl.) Y.R.Ling & Humphries, var. qinghaiensis Y.R.Ling, and var. turkestanica Krasch.—and one subspecies, subsp. ladakhensis L.Ali, Khuroo & A.H.Ganie [64]. Most of the abovementioned varieties and subspecies may occur in Asia, highlighting the need for a thorough investigation of their chemical composition. It is also important to define the range limits of the Siberian tarragon population and to monitor changes in its chemical composition across its distribution.
A key research objective following the study of a plant’s phytochemical composition is to evaluate the biological activity of its extracts to develop a potential therapeutic or medicinal product. Compounds present at the highest concentrations are likely to have the greatest impact on the extract’s biological effects. Because phenolic compounds can exhibit diverse biological activities, it is reasonable to expect that tarragon extracts may possess bioactivity based on the known properties of individual compounds. Our results indicate that at least ten compounds are present in the plant at levels of 0.4–1.7% of the raw material mass, suggesting that they are likely to contribute to the biological activity of the total extract (Table 5).
In decreasing order of abundance, the major compounds in A. dracunculus are naringenin 7-O-methyl ester (sakuranetin), chrysoeriol 7-O-glucoside (thermopsoside), acacetin 7-O-glucoside (tilianin), 3,5-di-O-caffeoyl-quinic acid, naringenin 7,4′-di-O-methyl ester, naringenin, diosmetin 7-O-glucuronide, luteolin 7-O-glucoside (cynaroside), naringenin 4′-O-methyl ester (isosakuranetin), and naringenin 5,7-di-O-methyl ester.
According to published studies, most of these compounds exhibit anticancer, antiviral, antioxidant, antimicrobial, and anti-inflammatory activities [65,67,68,69,70,72,73,74,77,78,81]. Neuroprotective potential has been reported for chrysoeriol 7-O-glucoside [66], acacetin 7-O-glucoside [67], naringenin [72,73], and 3,5-di-O-caffeoyl-quinic acid [68], while cardioprotective effects have been observed for tilianin [67], 3,5-di-O-caffeoyl-quinic acid [68], and isosakuranetin [80]. Positive metabolic effects, including antidiabetic, anti-atherosclerotic, hypoglycemic, and α-amylase/α-glucosidase inhibitory actions, have been associated with tilianin [67], naringenin [72,73], cynaroside [77], diosmetin 7-O-glucuronide [76], and 3,5-di-O-caffeoyl-quinic acid [68]. Naringenin 7,4′-di-O-methyl ester and tilianin have also been shown to be effective sleep-promoting [71] and antidepressant agents [67]. Additional activities include antiallergic effects (sakuranetin) [65], hepatoprotective effects (3,5-di-O-caffeoyl-quinic acid and cynaroside) [68,77], hyaluronidase inhibition (diosmetin 7-O-glucuronide) [75], and melanogenic effects [79]. Naringenin 5,7-di-O-methyl ester is a compound with as yet unknown biological activity. Although the activity of individual compounds does not guarantee that the extract will exhibit the same effects, it indicates the potential for such activity. Therefore, further studies are needed to confirm the extract’s pharmacological properties. Furthermore, the data on the accumulation of individual compounds indicate that A. dracunculus may serve as a source of unique compounds, including flavone O-glycosides and certain lipophilic aglycones.

4. Conclusions

Unreported East Siberian accessions of A. dracunculus (Mukhorshibirsky District, Republic of Buryatia) were subjected to LC–MS profiling for the first time in a study aimed at assessing the chemodiversity of a North Asian tarragon population occupying extensive areas of Siberian Russia. Siberian tarragon is distinguished from previously studied populations in Europe, Asia, America, and Africa by its unique phenolic profile and high phenolic content. Specifically, 80 compounds were identified, more than three-quarters of which are reported for the first time in A. dracunculus. Quantitatively, the primary compounds were flavone O-glycosides (e.g., chrysoeriol 7-O-glucoside, acacetin 7-O-glucoside, and diosmetin 7-O-glucuronide) and methylated flavanone aglycones (e.g., naringenin 7-O-methyl ester, naringenin 7,4′-di-O-methyl ester, and naringenin 4′-O-methyl ester), which is uncommon in most tarragon populations worldwide. The high content of various phenolics (10.9–12.9% of dry plant weight) suggests the potential for various beneficial properties of A. dracunculus extracts in biomedical, nutritional, and cosmetic applications. These findings indicate that Siberian tarragon warrants further study and promotion as a new variation of this well-known medicinal and culinary plant.

Supplementary Materials

The following supporting information can be downloaded at https://www.mdpi.com/article/10.3390/horticulturae11111393/s1, Table S1: Regression equations, correlation coefficients, standard deviations, limits of detection, limits of quantification, and linear ranges for reference standards; Table S2: Occurrence of compounds 1–80 in Artemisia dracunculus samples collected from sites 1–65; Table S3: Content of compounds 1–80 in ten Artemisia dracunculus samples.

Author Contributions

Conceptualization, methodology, software, validation, formal analysis, investigation, resources, data curation, writing—original draft preparation, writing—review and editing, visualization, supervision, project administration, and funding acquisition, D.N.O., N.I.K. and N.K.C. All authors have read and agreed to the published version of the manuscript.

Funding

This research was funded by the Ministry of Education and Science of Russia, grant numbers 121030100227-7; FSRG-2023-0027.

Data Availability Statement

The original contributions presented in this study are included in the article/Supplementary Materials. Further inquiries can be directed to the corresponding author(s).

Acknowledgments

The authors have reviewed and edited the manuscript and accept full responsibility for its content.

Conflicts of Interest

The authors declare no conflicts of interest. The funders were not involved in the study design, data collection, analysis, or interpretation; the writing of the manuscript; or the decision to publish the results.

Abbreviations

The following abbreviations are used in this manuscript:
CQACaffeoyl quinic acid
DCQADicaffeoyl quinic acid
DWDry weight
FQAFeruloyl quinic acid
FlAsFlavonoid aglycones
FlGsFlavonoid glycosides
HCysHydroxycinnamates
HPLC-PDA-IT-TOF-MSHigh-performance chromatography with photodiode array and ion trap–time-of-flight mass spectrometry detection
TCQATricaffeoyl quinic acid
TPCTotal phenolic content
UVUltraviolet

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Horticulturae 11 01393 g001
Figure 1. Siberian tarragon herb in its natural habitat (a); site No 42, https://www.inaturalist.org/observations/229202649 (accessed on 14 October 2025)) and map of the study area showing collection sites No 1–65 with coordinates of the outermost points (b).
Figure 1. Siberian tarragon herb in its natural habitat (a); site No 42, https://www.inaturalist.org/observations/229202649 (accessed on 14 October 2025)) and map of the study area showing collection sites No 1–65 with coordinates of the outermost points (b).
Horticulturae 11 01393 g001
Horticulturae 11 01393 g002
Figure 2. HPLC-PDA chromatogram of A. dracunculus herb (sample No. 42) showing the most diverse HPLC profile at 290 nm. Descriptions of compounds 1–80 are provided in Table 2. ISs—internal standards (IS1—dracocephoside I, 5 μg/mL [58]; IS2—arcapillin 4′-O-acetate, 2 μg/mL [59]).
Figure 2. HPLC-PDA chromatogram of A. dracunculus herb (sample No. 42) showing the most diverse HPLC profile at 290 nm. Descriptions of compounds 1–80 are provided in Table 2. ISs—internal standards (IS1—dracocephoside I, 5 μg/mL [58]; IS2—arcapillin 4′-O-acetate, 2 μg/mL [59]).
Horticulturae 11 01393 g002
Table 1. Phenolic compounds detected in Artemisia dracunculus from various geographical origins.
Table 1. Phenolic compounds detected in Artemisia dracunculus from various geographical origins.
Country: LocalityC/W 1Group of Phenolics Identified in A. dracunculus (Principal Compounds and Content, mg/g DW). Total Phenolic Content (TPC; mg/g DW) 2Ref.
Europe
France: Milly la ForetCFlavonol glycosides: rutin, quercetin 3-O-robinobioside, isoquercitrin, patuletin 3-O-rutinoside, patuletin 3-O-robinobioside, patulitrin. Lipophilic aglycones: quercetin[12]
Germany: WürzburgCCoumarins: herniarin, scoparone, scopoletin. Isocoumarins: capillarin, 8-hydroxycapillarin, capillarin isovalerate, artemidinol, 8-hydroxyartemidin, 3-butenylisocoumarin, 3-butenyl-5/8-hydroxyisocoumarins[11,13,14,15]
GreeceCBenzoic acids: gentisic acid. Cinnamic acids: caffeic acid, ferulic acid. Caffeoylquinic acids: 5-CQA. Flavonol glycosides: rutin, isoquercitrin, quercitrin. Lipophilic aglycones: kaempferol, quercetin, luteolin, apigenin[16]
Italy: Sestola, ModenaCBenzoic acids: protocatechuic acid hexose. Caffeoylquinic acids. Coumaroylquinic acids. Feruloylquinic acid. Flavonol glycosides: rutin, nicotiflorin. Flavone glycosides: scolymoside. TPC < 10[17]
Poland: WarsawCBenzoic acids: protocatechuic/syringic acid hexosides. Cinnamic acids: ferulic acid hexoside. Caffeoylquinic acids. Flavonol glycosides: isoquercitrin, hyperoside, quercetin/patuletin/isorhamnetin glycosides. Flavone glycosides: vicenin-2. Chalcones: davidigenin, 2′,4′-dihydroxy-4-methoxydihydrochalcone. Lipophilic aglycones: sakuranetin, quercetin[18]
Portugal: BragançaCCinnamic acids: ferulic acid hexoside (0.43–0.65), caftaric acid (0.89–1.26). Caffeoylquinic acids: 5-CQA (6.69–8.56), 4-CQA (0.64–1.14), 4,5-DQCA (1.52–3.39), 3,4-DQCA (0.56–2.75), 1,3,5-TCQA (5.87–7.86). Flavanone glycosides: naringenin-O-hexoside (0–0.21). Flavonol glycosides: rutin (3.55–9.88), narcissin (0–0.11). Flavone glycosides: cynaroside (0.80–1.09). Lignans: medioresinol-O-hexoside (0.10–0.34). TPC 25.05–45.27 (in extracts)[19]
Portugal: Coimbra, LisbonCPhenols: eugenol (0.08). Benzoic acids: protocatechuic acid (0.02). Cinnamic acids: p-coumaric acid (0.10), ferulic acid (1.23). Caffeoylquinic acids: 5-CQA (3.95). Stilbenes: resveratrol (0.01)[20]
Romania: Cluj-NapocaCBenzoic acids: α-resorcylic acid (0.04). Caffeoylquinic acids: 5-CQA (3.26), 3,5-DCQA (1.64), 4,5-DQCA (1.40). Feruloylquinic acids: 5-FQA (1.44). Feruloyl-caffeoylquinic acids: 4-O-feruloyl-5-O-caffeoylquinic acid (0.17). Flavonol glycosides: rutin (0.61). Flavone glycosides: apigenin-glucosyl-arabinoside (0.20), apigenin-arabinosyl-glucoside (0.03). Lipophilic aglycones: 6,7,4′-trimethoxy-galetin (0.06), 6,7,3′,4′-tetramethoxy-quercetagetin (0.04). TPC 14.57[21]
Russia: Crimea,
cv. Smaragd		CBenzoic acids: gentisic acid. Coumarins: fraxidin, isofraxidin. Caffeoylquinic acids: 5-CQA. Feruloylquinic acids: 3-FQA. Flavonol glycosides: rutin, narcissin, isoquercitrin. Flavone glycosides: cynaroside. Lipophilic aglycones: quercetin, isorhamnetin, luteolin, eupatolitin, chrysosplenol D, cirsilineol, casticin[22]
Russia: Samara,
cv. Gribovskii		CFlavone glycosides: estragonoside. Flavanone glycosides: pinocembrin 7-O-glucoside. Lipophilic aglycones: annagenin, pinocembrin (0.35–0.38), naringenin[23,24]
Switzerland: ViennaCIsocoumarins: capillarin, 8-hydroxycapillarin, artemidin, 8-hydroxyartemidin, artemidinol, artemidiol[25]
West Siberia
Russia: NovosibirskCIsocoumarins: artemidin, dracumerin[14]
West Asia
Iran: University of Tehran, KarajCBenzoic acids: syringic acid (0.03–0.29), vanillic acid (0–0.26). Cinnamic acids: p-coumaric acid (0–0.32), caffeic acid (0.03–0.25), ferulic acid (0–0.57). Caffeoylquinic acids: 5-CQA (0.06–0.37). Coumarins: coumarin (0–0.40), herniarin (0.33–0.94). Lipophilic aglycones: naringenin (0–0.06), luteolin (0.54–5.62), apigenin (0–0.001), quercetin (0–0.01). TPC 40.91–96.52 (in extracts)[26]
IranCFlavonol glycosides: rutin, quercitrin[27]
Turkey: ErzurumCPhenylpropanoids: 4-(1′,1′,2′,2′-tetramethylpropyl)-1,2-benzenediol, 3-(p-methoxyphenyl)-1,2-propanediol. Coumarins: herniarin. Flavonol glycosides: rutin[28]
Central Asia
KasakhstanWFlavonol glycosides: rutin, bioquercetin, hyperoside, isorhamnetin 7-O-(p-hydroxybenzoyl)-galactoside. Lipophilic aglycones: kaempferol, quercetin, luteolin.[29,30]
KyrgyzstanWCoumarins: herniarin, scoparone. Isocoumarins: dracumerin, artemidin. Lipophilic aglycones: naringenin 7-O-methyl ester, eriodictyol 7-O-methyl ester, eriodyctiol 7,3′-di-O-methyl ester[31]
UzbekistanWIsocoumarins: artemidin, artemidinal, artemidiol[32,33,34,35]
UzbekistanCIsocoumarins: 2′-methoxydihydroartemidin, (-)-(R,S)-epoxyartemidin, (+)-(R)-(E)-3′-hydroxyartemidin[14]
East Asia
Mongolia: Bulgan AimakWPhenols: eugenol 4-O-glucoside. Cinnamic acids: p-hydroxyphenylethyl-O-glucoside 6′-O-caffeate. Isocoumarins: capillarin. Lignans. Lipophilic aglycones: naringenin, eriodictyol, hesperetin[36]
China: Tianshan Mountains, AksuCBenzaldehydes: protocatechuic aldehyde (0.08). Benzoic acids: protocatechuic acid (1.34). Cinnamic acids: caffeic acid (0.31). Catechins: catechin (0.52). Flavonol glycosides: rutin (0.88), isoquercitrin (0.87), astragalin (0.76). Chalcones: phloretin (0.001). Lipophilic aglycones: kaempferol (0.07), quercetin (0.06), isorhamnetin (0.03), luteolin (0.13), apigenin (0.04), naringenin (0.006), taxifolin (0.27), aromadendrin (0.01). TPC 5.67[37]
North America
Canada: Lytton, British ColumbiaWCoumarins: scoparone. Isocoumarins: capillarin. Lipophilic aglycones: aromadendrin 7-O-methyl ester, taxifolin 7,3′-di-O-methyl ester, naringenin, eriodyctiol 7,4′-di-O-methyl ester[36,38,39]
Canada: New Brunswick, NJCChalcones: 4-O-methyldavidigenin, 4′-O-methyldavidigenin, 2′,4′-dihydroxy-4-methoxydihydrochalcone, 2′,4-dihydroxy-4′-methoxydihydrochalcone. Lipophilic aglycones: sakuranetin[40,41]
USA: states California, Colorado, Nevada, Utah, WyomingWCaffeoylquinic acids: 5-CQA, 4,5-DQCA. Chalcones: davidigenin, 2′,4′-dihydroxy-4-methoxydihydrochalcone. Lipophilic aglycones: sakuranetin[42]
North Africa
Morocco: SaléWCoumarins: herniarin. Phytoalexins: 5-acetyl-6-hydroxy-2-(1-hydroxy-
1-methylethyl)benzofuran. Prestragols: 3-(4′-methoxyphenyl)-prop-1,2-diol		[43]
1 Sample origin: C—cultivated; W—wild. 2 Abbreviations used: CQA—caffeoylquinic acid; DCQA—dicaffeoylquinic acid,=; FQA—feruloylquinic acid; TCQA—tricaffeoylquinic acid.
Table 2. Retention time (tR), molecular formula (MF), MS data, UV pattern (UVP), identification level (IL), and occurrence of compounds 1–80 detected in A. dracunculus herb.
Table 2. Retention time (tR), molecular formula (MF), MS data, UV pattern (UVP), identification level (IL), and occurrence of compounds 1–80 detected in A. dracunculus herb.
NotR, minCompoundMF (Error, ppm)MS, [M-H]−, m/zMS2,
m/z		UVP 1IL 2Previously Found in A. dracunculus [ref.]Occurrence of Compound 3, %
13.381-O-Caffeoyl-quinic acid, trans-isomerC16H18O9 (1.2)353179C11 (CF, 99121, 98)No90.7
24.33O-Caffeoyl hexoseC15H18O9 (0.8)341179C12 [44]No98.4
34.48Caffeoyl-quinic acid, cis-isomer C16H18O9 (1.9)353179C22 [45]No76.9
44.56O-Caffeoyl hexoseC15H18O9 (0.5)341179C12 [44]No78.4
55.49Caftaric acid, trans-isomerC13H12O9 (0.5)311179C11 (CF, 00384, 98)Yes [19]76.9
65.922-O-Feruloyl β-glucoseC16H20O9 (1.1)355193C11 (LC, [46], 92)No84.6
76.41O-Caffeoyl hexoseC15H18O9 (1.8)341179C12 [44]No87.6
87.72Caftaric acid, cis-isomer (tent.)C13H12O9 (0.9)311179C22 [45]No95.3
97.994-O-Feruloyl β-glucoseC16H20O9 (1.7)355193C11 (LC, [46], 92)No93.8
108.274-O-Caffeoyl-quinic acid, trans-isomerC16H18O9 (1.0)353179C11 (SA, 65969, 98)Yes [19]100
118.451-O-Caffeoyl β-glucoseC15H18O9 (0.8)341179C11 (MCE, W416228, 97)No100
128.731,4-Di-O-caffeoyl-quinic acidC25H24O12 (1.9)515353C11 (CF, 99122, 98)No95.3
139.221-O-Feruloyl β-glucoseC16H20O9 (1.0)355193C11 (Sy, FG509, 98)No100
149.43O-Caffeoyl hexoseC15H18O9 (0.9)341179C12 [44]No89.2
159.526-O-Feruloyl β-glucoseC16H20O9 (2.2)355193C11 (Sy, FG129, 98)No100
169.93Quercetin O-hexoside-O-hexuronideC27H28O18 (1.8)639477, 301F12 [47]No80
1710.26Scopoletin 7-O-glucoside (scopolin)C16H18O9 (1.8)353191Co1 (SA, PHL82649, 95)No100
1810.675-O-Caffeoyl-quinic acid, trans-isomerC16H18O9 (1.0)353179C11 (SA, 94419, 98)Yes [22,60]100
1911.143-O-Caffeoyl-quinic acid, trans-isomerC16H18O9 (0.5)353179C11 (MCE, N0055, 99)No100
2011.51Umbelliferone 7-O-glucoside (skimmin)C15H16O8 (1.1)323161Co1 (MCE, N2263, 99)No96.9
2111.90Apigenin-6,8-di-C-glucoside (vicenin 2)C27H30O15 (1.1)593503, 473, 413, 383, 353F21 (SA, 03980585, 98)Yes [22,60]100
2212.465-O-Caffeoyl-quinic acid, cis-isomerC16H18O9 (1.4)353179C21 (CR, 2063256, 95)No100
2312.72Caffeic acidC9H8O4 (0.3)179 C11 (SA, C06025, 98)Yes [60]92.3
2413.09Apigenin-6-C-glucoside (isovitexin)C21H20O10 (1.5)431383, 353F21 (SA, 17804, 98)No100
2513.17Eriodictyol O-hexoside (tent. eriodictyol 5-O-glucoside)C21H22O11 (0.9)449287F32 [48]No100
2613.88Eriodictyol 7-O-glucoside (pyracanthoside)C21H22O11 (0.8)449287F31 (SA, 19474, 99)No100
2714.03Apigenin-8-C-glucoside (vitexin)C21H20O10 (1.0)431383, 353F21 (SA, 00840595, 98)No89.2
2814.554-O-Feruloyl-quinic acid, trans-C17H20O9 (1.2)367193C11 (MCE, N6598, 99)No100
2914.97Luteolin 5-O-glucoside (galuteolin)C21H20O11 (1.1)447285F41 (MCE, N2008, 97)No92.3
3015.115-O-Feruloyl-quinic acid, trans-C17H20O9 (0.9)367193C11 (CF, 92889, 98)Yes [21]100
3115.53Diosmetin 7,3′-di-O-glucuronideC28H28O18 (0.5)651475, 299F41 (Sy, DD399, 95)No100
3215.89Eriodictyol O-hexoside (tent. eriodictyol 3′- or 4′-O-glucoside)C21H22O11 (1.2)449287F32 [49]No100
3316.021,5-Di-O-caffeoyl-quinic acidC25H24O12 (1.8)515353C11 (CF, 90937, 98)No100
3416.06Luteolin 7-O-glucoside (cynaroside)C21H20O11 (0.6)447285F41 (SA, 49968, 96)Yes [22]100
3516.55Chrysoeriol 7-O-glucoside (thermopsoside)C22H22O11 (0.3)461299F41 (BC, 3796, 98)No100
3616.90Luteolin 4′-O-glucoside (juncein)C21H20O11 (0.9)447285F41 (MCE, N8309, 99)No100
3716.923,4-Di-O-caffeoyl-quinic acidC25H24O12 (1.1)515353C11 (SA, SMB00224, 90)Yes [19]100
3817.253,5-Di-O-caffeoyl-quinic acidC25H24O12 (0.5)515353C11 (SA, SMB00131, 95)Yes [60]100
3917.57Eriodictyol O-hexoside (tent. eriodictyol 3′- or 4′-O-glucoside)C21H22O11 (1.0)449287F32 [49]No100
4017.784,5-Di-O-caffeoyl-quinic acidC25H24O12 (0.7)515353C11 (SA, SMB00221, 95)Yes [60]100
4117.95Acacetin 7-O-glucoside (tilianin)C22H22O10 (0.9)445283F21 (MCE, N2555, 99)No100
4218.29Diosmetin 7-O-glucuronideC22H20O12 (1.1)475299F41 (Sy, DD601, 95)No100
4318.49Homoeriodictyol 7-O-glucosideC22H24O11 (1.0)463301F31 (CF, 98463, 98)No93.8
4418.92Apigenin 7-O-glucuronideC21H18O11 (1.6)445269F21 (CF, 98500, 98)No100
4519.21Diosmetin 3′-O-glucuronideC22H20O12 (1.0)475299F41 (Sy, DD321, 95)No100
4619.873-O-Feruloyl-4-O-caffeoyl-quinic acidC26H26O12 (1.9)529353, 367C11 (MCE, N10044, 95)No100
4720.263-O-Feruloyl-5-O-caffeoyl-quinic acidC26H26O12 (1.2)529353, 367C11 (LC, [50], 90)No90.7
4821.19Apigenin 4′-O-glucuronideC21H18O11 (1.4)445269F21 (LGC, A72613, 90)No92.3
4921.82Pinocembrin 7-O-glucosideC21H22O9 (0.8)417255F31 (MCE, N6615, 99)Yes [23,24]90.7
5022.09EriodictyolC15H12O6 (0.9)287 F31 (CF, 99719, 98)No100
5122.51Pinocembrin 7-O-glucuronideC21H20O10 (1.4)431255F31 (PB, 37180005, 90)No100
5222.70Luteolin 7-O-(6″-O-acetyl)-glucosideC23H22O12 (1.1)489447, 285F41 (LC, [51], 90)No100
5322.98Luteolin 7-O-(2″,6″-di-O-malonyl)-glucoside (anthriscoside C)C27H24O17 (0.4)619533, 447, 285F41 (LC, [52], 93)No100
5423.08Eriodictyol methyl ester (tent. eriodictyol 5-O-methyl ester)C16H14O6 (1.7)301287F32 [53]No100
5523.41Chrysoeriol 7-O-(2″-O-acetyl)-glucoside (2″-O-acetylthermopsoside)C24H24O12 (1.2)503461, 299, 285F41 (LC, [54], 92)No89.2
5623.52Luteolin 7-O-(3″,6″-di-O-acetyl)-glucosideC25H24O13 (0.9)531489, 447, 285F41 (LC, [55], 95)No92.3
5723.69Chrysoeriol 7-O-(6″-O-acetyl)-glucoside (6″-O-acetylthermopsoside)C24H24O12 (1.7)503461, 299, 285F41 (LC, [54,56], 90)No92.3
5823.99Eriodictyol 7-O-methyl ester (sternbin)C16H14O6 (1.0)301287F31 (CF, 78833, 98)Yes [60]100
5924.54NaringeninC15H12O5 (0.4)271 F31 (CF, 98742, 98)Yes [60]100
6024.75Naringenin 7-O-methyl ester (sakuranetin)C16H14O5 (0.7)285271F31 (Ex, 1247S, 99)Yes [60]100
6124.87Naringenin 5,7-di-O-methyl esterC17H16O5 (1.2)299285, 271F31 (Cy, BP2362, 95)No100
6225.04Diosmetin (luteolin 4′-O-methyl ester)C16H12O6 (1.5)299285F41 (SA, PHL82526, 95)No90.7
6325.51PinobanksinC15H12O5 (1.0)271 F51 (SA, 68530, 95)No84.6
6425.97Eriodictyol 4′-O-methyl ester (hesperetin)C16H14O6 (0.9)301287F31 (SA, W431300, 95)Yes [36]89.2
6526.25Eriodictyol 7,4′-di-O-methyl ester (persicogenin)C17H16O6 (1.7)315301, 287F31 (BC, 7744, 98)Yes [60]100
6626.51Chrysoeriol (luteolin 3′-O-methyl ester)C16H12O6 (1.0)299285F41 (CF, 98785, 98)No100
6726.59Pinobanksin 5-O-methyl esterC16H14O5 (1.0)285271F51 (CF, 89500, 98)No81.5
6826.97Luteolin 7,4′-di-O-methyl esterC17H14O6 (1.7)313299, 285F41 (ACB, X210855, 97)No89.2
6927.32Naringenin 4′-O-methyl ester (isosakuranetin)C16H14O5 (0.9)285271F31 (Ex, 1122S, 99)No100
7027.49Naringenin 7,4′-di-O-methyl esterC17H16O5 (1.6)299285, 271F31 (Cy, EBA42496, 95)No100
7127.92PinocembrinC15H12O4 (0.7)255 F31 (CF, 98740, 98)Yes [60]100
7228.33Luteolin 7,3′,4′-tri-O-methyl ester (gonzalitosin I)C18H16O6 (0.4)327313, 299, 285F41 (MCE, N7012, 98)No90.7
7328.52Pinocembrin 5-O-methyl ester (alpinetin)C16H14O4 (1.4)269255F31 (CF, 98489, 98)No95.3
7428.90Acacetin (apigenin 4′-O-methyl ester)C16H12O5 (1.1)283269F21 (CF, 98744, 98)No96.9
7529.94Eriodictyol 7,3′-di-O-methyl esterC17H16O6 (1.0)315301, 287F31 (CF, 89533, 98)Yes [60]90.7
7630.02Eriodictyol trimethyl esterC18H18O6 (1.7)329315, 301, 287F32 [57]No98.4
7730.33Pinocembrin 7-O-methyl ester (pinostrobin)C16H14O4 (0.7)269255F31 (Ex, 1095, 95)No93.8
7831.01Eriodictyol 7,3′,4′-tri-O-methyl esterC18H18O6 (2.0)329315, 301, 287F31 (CF, 89491, 98)No95.3
7931.48Naringenin 5,7,4′-tri-O-methyl esterC18H18O5 (2.2)313299, 285, 271F31 (CF, 98616, 98)No100
8031.78Pinocembrin 5,7-di-O-methyl esterC17H16O4 (1.7)283269, 255F31 (Ex, 1296, 95)No100
1 UV patterns. Cinnamates: C1—caffeic/ferulic acid derivatives, trans-form (λmax 322–324 nm); C2—caffeic/ferulic acid derivatives, cis-form (λmax 316–318 nm); Co—simple coumarins (λmax 320–322 nm); F1—quercetin derivatives (λmax 254–256, 353–355 nm); F2—apigenin derivatives (λmax 266–268, 330–332 nm); F3—flavanone derivatives (λmax 289–291 nm); F4—luteolin derivatives (λmax 253–255, 348–350 nm); F5—pinobanksin derivatives (λmax 285 nm). 2 Identification levels: (1) identified compounds after comparison of retention times, UV spectra, and mass spectral data with previously isolated compounds or commercial reference standard (in brackets—manufacturer: ACB—Advanced ChemBlocks (Hayward, CA, USA); BC—BioCrick (Chengdu, China); CF—ChemFaces (Wuhan, China); CR—Carl Roth (Karlsruhe, Germany); Cy—Cymit Qyimica (Barselona, Spain); Ex—Extrasynthese (Lyon, France); LC—Laboratory collection (ref., purity percentage); LGC—LGC Standards (Beijing, China); MCE—MedChemExpress (Monmouth Junction, NJ, USA); PS—Push BioTechnologies (Chengdu, China); SA—SigmaAldrich (St. Louis, MO, USA); Sy—Synthose (Concord, Canada); catalog number; purity percentage); (2) putatively annotated compounds based on comparison of retention times, UV spectra, and mass spectral data with literature sources (In brackets—ref.). 3 Occurence of each compound was calculated as [(number of cites positive for the compound)/(total number of cites)] × 100%.
Table 3. Overview of phenolic groups identified in global and Siberian populations of A. dracunculus.
Table 3. Overview of phenolic groups identified in global and Siberian populations of A. dracunculus.
Phenolic GroupPresence in Global PopulationsPresence in the Siberian Population
PhenolsEurope [20], East Asia [36]Not found
BenzaldehydesEast Asia [37]Not found
Benzoic acidsEurope [16,17,18,20,21,22], West Asia [26], East Asia [37]Not found
Cinnamic acidsEurope [16,18,19,20], West Asia [26], East Asia [36,37]Detected
Hydroxycinnamoylquinic acidsEurope [16,17,18,19,20,21,22], West Asia [26], North America [42]Detected
CoumarinsEurope [11,13,14,15,22], West Asia [26,28], Central Asia [31], North America [36,38], North Africa [43]Trace
IsocoumarinsEurope [11,13,14,15,25], Central Asia [14,31,32,33,34,35], East Asia [36], North America [36,38]Not found
Flavonol glycosidesEurope [12,16,17,19,21], West Asia [27,28], Central Asia [29,30], East Asia [1]Trace
Flavone glycosidesEurope [17,19,21,22,23,24]Detected
Flavanone glycosidesEurope [18,19,23,24]Detected
CatechinsEast Asia [37]Not found
ChalconesEurope [18], East Asia [37], North America [40,41,42]Not found
LignansEurope [19]Not found
StilbenesEurope [20]Not found
Lipophilic aglycones
flavonesEurope [16,23], West Asia [26], Central Asia [29,30], East Asia [37]Detected
flavonolsEurope [12,16,18,22], West Asia [26], Central Asia [29,30], East Asia [37]Not found
flavanonesEurope [18,23,24], West Asia [26], East Asia [36,37], North America [40,41,42]Detected
flavanonolsEast Asia [37]Traces
methoxylated flavonolsEurope [21,22]Not found
methoxylated flavonesEurope [22]Detected
methoxylated flavanonesCentral Asia [31], East Asia [36], North America [36,38]Detected
methoxylated flavanonolsNorth America [36,38]Not found
Table 4. Content of phenolic compound groups in A. dracunculus from the Siberian population.
Table 4. Content of phenolic compound groups in A. dracunculus from the Siberian population.
Phenolic GroupMin, mg/g DWMax, mg/g DWMedian, mg/g DWS.D.
Flavonoid glycosides
Apigenin glucosides1.812.582.220.28
Acacetin glucosides14.2115.9815.140.40
Luteolin glucosides6.838.177.440.41
Diosmetin glucosides7.088.638.000.40
Chrysoeriol glucosides15.0216.0415.520.29
Pinocembrin glucosides1.081.591.390.14
Eriodictyol glucosides0.871.791.410.30
Homoeriodictyol glucosides0.260.530.450.08
Total flavone glucosides45.5350.6548.321.41
Total flavanone glucosides2.233.803.250.49
Total flavonoid glycosides48.2954.4451.571.90
Flavonoid aglycones
Flavone methyl esters<0.010.070.020.02
Nonmethylated flavanone aglycones7.8310.599.120.64
Pinocembrin methyl esters0.120.570.430.10
Naringenin methyl esters34.7141.3838.781.99
Eriodictyol methyl esters0.300.760.530.15
Flavanone methyl esters35.2242.4339.742.23
Total flavonoid aglycones43.0652.5348.902.70
Total flavonoids92.00106.97100.464.61
Hydroxycinnamates
Monocaffeoyl-quinic acids2.543.763.300.40
Dicaffeoyl-quinic acids12.3214.5113.570.56
Feruloyl-quinic acids1.41.971.780.16
Feruloyl-caffeoyl-quinic acids0.881.311.130.12
Caffeoyl glucoses/hexoses0.220.70.510.16
Feruloyl glucoses<0.010.090.050.03
Caffeoyl tartaric acids0.050.140.100.02
Total caffeoyl-quinic acids14.8617.9816.870.96
Total hydroxycinnamoyl-quinic acids17.3221.0619.791.20
Total hydroxycinnamoyl glucoses/hexoses0.230.770.560.17
Total hydroxycinnamic acid derivatives17.6121.8420.461.40
Trace compounds
Coumarins<0.01<0.01<0.01—
Flavonol glucosides<0.01<0.01<0.01—
Flavanonol methyl esters<0.01<0.01<0.01—
Total phenolics109.61128.81120.936.00
Table 5. Summary of content and reported bioactivity of the ten dominant compounds in A. dracunculus.
Table 5. Summary of content and reported bioactivity of the ten dominant compounds in A. dracunculus.
Content in A. dracunculus, %CompoundReported Bioactivity [Ref.]
1.5–1.7Naringenin 7-O-methyl ester (sakuranetin)Anticancer, antiviral, antioxidant, antimicrobial, anti-inflammatory, antiparasitic, antimutagenic, antiallergic [65]
1.5–1.6Chrysoeriol 7-O-glucoside (thermopsoside)Neuroprotective [66]
1.4–1.6Acacetin 7-O-glucoside (tilianin)Anticancer, antidiabetic, anti-inflammatory, antioxidant, anti-depressant, cardioprotective, neuroprotective [67]
1.0–1.23,5-Di-O-caffeoyl-quinic acidAnticancer, antioxidative, cardioprotective, antibacterial, antiviral, hypoglycemic, hepatoprotective, anti-inflammatory, neuroprotective [68]
1.0–1.2Naringenin 7,4′-di-O-methyl esterAnticancer [69], antimicrobial, antifungal [70], sleep-promoting [71]
0.7–0.9NaringeninAnticancer, antidiabetic, antiatherosclerosis, hypoglycemic, anti-neurodegenerative, antioxidant [72,73]
0.6–0.8Diosmetin 7-O-glucuronideAnticancer [74], hyaluronidase inhibitor [75], α-amylase/α-glucosidase inhibitor [76]
0.6–0.7Luteolin 7-O-glucoside (cynaroside)Anticancer, antibacterial, antifungal, antileishmanial, antioxidant, hepatoprotective, antidiabetic, anti-inflammatory [77]
0.5–0.7Naringenin 4′-O-methyl ester (isosakuranetin)Antibacterial [78], stimulates melanogenesis [79], cardioprotective [80], antioxidant [81]
0.4–0.5Naringenin 5,7-di-O-methyl esterNo data
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Olennikov, D.N.; Kashchenko, N.I.; Chirikova, N.K. Siberian Tarragon: A Promising Source of Flavone O-Glycosides and Methylated Flavanone Aglycones in North Asian Accessions of Artemisia dracunculus. Horticulturae 2025, 11, 1393. https://doi.org/10.3390/horticulturae11111393

AMA Style

Olennikov DN, Kashchenko NI, Chirikova NK. Siberian Tarragon: A Promising Source of Flavone O-Glycosides and Methylated Flavanone Aglycones in North Asian Accessions of Artemisia dracunculus. Horticulturae. 2025; 11(11):1393. https://doi.org/10.3390/horticulturae11111393

Chicago/Turabian Style

Olennikov, Daniil N., Nina I. Kashchenko, and Nadezhda K. Chirikova. 2025. "Siberian Tarragon: A Promising Source of Flavone O-Glycosides and Methylated Flavanone Aglycones in North Asian Accessions of Artemisia dracunculus" Horticulturae 11, no. 11: 1393. https://doi.org/10.3390/horticulturae11111393

APA Style

Olennikov, D. N., Kashchenko, N. I., & Chirikova, N. K. (2025). Siberian Tarragon: A Promising Source of Flavone O-Glycosides and Methylated Flavanone Aglycones in North Asian Accessions of Artemisia dracunculus. Horticulturae, 11(11), 1393. https://doi.org/10.3390/horticulturae11111393

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