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17 December 2022

Comparison of Wild and Introduced Dracocephalum jacutense P.: Significant Differences of Multicomponent Composition

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1
N.I. Vavilov All-Russian Institute of Plant Genetic Resources, B. Morskaya 42-44, 190000 Saint-Petersburg, Russia
2
Institute of Life Science and Biomedicine, Far Eastern Federal University, Sukhanova 8, 690950 Vladivostok, Russia
3
Department of Biology, North-Eastern Federal University, Belinsky Str. 58, 677000 Yakutsk, Russia
4
Yakutsk Botanical Garden, Institute for Biological Problems of Cryolithozone Siberian Branch of Russian Academy Sciences, Lenina pr. 41, 677000 Yakutsk, Russia
Horticulturae2022, 8(12), 1211;https://doi.org/10.3390/horticulturae8121211
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Abstract

Dracocephalum jacutense is endemic to eastern Siberia of Russia and is accepted in the rare and endangered category. The plant was first collected by K.S. Baikov in 1985 in the vicinity of the village Sangar (Kobyaysky district, Yakutia) and then described by G.A. Peshkova in “Flora of Siberia” in 1997. D. jacutense has been introduced in the Botanical Garden of Yakutia since 2009. The aim of this work is to conduct a comparative analysis of the chemical composition of aerial parts (leaves, inflorescences, stems) of D. jacutense Peschkova collected both in controlled conditions (the Botanical Garden of Yakutia) and in a natural-grown area (the vicinity of the village of Sangar, Kobyaysky district of Yakutia). A total of 156 bioactive compounds were successfully characterized in extracts of D. jacutense based on their accurate MS (Mass Spectrometry) fragment ions by searching online databases and the reported literature. The detailed study of the composition by tandem mass spectrometry revealed a significant difference in the polyphenol composition of the samples. Wild-grown plant samples had a higher number of polyphenolic compounds (92 compounds) than plant samples grown in the Botanical Garden (56 compounds), which were not previously described in the genus Dracocephalum. In addition, a total of 37 compounds of other chemical groups were identified that were not previously identified in the genus Dracocephalum. In general, the extract of D. jacutense, which was grown in wild conditions, was found to be a richer source of flavones, flavanols, flavan-3-ols, phenolic acids, and anthocyanidins compared to plants grown in controlled conditions in the Botanical Garden. Our results build on the current understanding of the biochemical richness of wild-grown samples over controlled-grown ones and preserve a rare and endangered D. jacutense in the flora of Yakutia. We proposed to be preserved on the basis of the development of an in vitro micropropagation protocol in our lab in the near future.

1. Introduction

Dracocephalum L. is a genus of herbaceous plants of the Lamiaceae family. There are five species of the genus Dracocephalum L. in the flora of the Republic of Sakha (Yakutia): D. palmatum Steph., D. ruyschiana L., D. nutans L., D. stellerianum Hiltebr. and D. jacutense Peschkova. D. jacutense Peschkova is listed in the Red Data Book of Yakutia [1,2].
Dracocephalum jacutense is a local endemic of Eastern Siberia and is found in a narrow growing condition. D. jacutense was first collected by K.S. Baikov in 1985 in the vicinity of the village Sangar (Kobyaysky district, Yakutia) and then described by G.A. Peshkova in “Flora of Siberia” in 1997 [3]. The plant has been introduced in the Botanical Garden of Yakutia since 2009 (Figure 1).
Figure 1. Collection areas for wild and introduced D. jacutense Peshkova.
D. jacutense is an herbaceous perennial with an ascending, hairy stem up to 40 cm long. P.S. Egorova revealed that the ontogenesis of the species in culture lasts about 10 years, while the complete ontogeny of wild populations lasts 24–32 years [4]. Flowering is regular each year in contrast to seed production; therefore, non-systematic seed production can become a vulnerable point in the cultivation and maintenance of the optimal abundance of the specie (Figure 2A).
Figure 2. (A) Flowering of D. jacutense P. in the nursery of the Botanical Garden of Yakutia; (photo taken by Egorova, July 2019); (B) Flowering of D. jacutense P. in wild grown conditions on the territory of the Kobyaysky district of Yakutia (photo taken by Rozhina, July 2022).
The genus Dracocephalum L. is noted for its high medicinal properties and the presence of nutrients. The content of bioactive substances in the aerial part of plants is rich and diverse, including cardenolides, tannins, coumarins, flavonoids, etc. [5]. Terpenoids, steroids, flavonoids, lignans, phenols, coumarins, cyanogenic compounds, and glucosides have been identified in the chemical composition of the genus Dracocephalum L. Among them, some components have antioxidant, antihypoxic, and immunomodulatory effects [6]. By optimizing extraction, scientists isolated and studied oils from the seeds of Lallemantia iberica (Dracocephalum ibericum M. Bieb.) and proposed to use them as fatty acid sources [7]. It has been experimentally proven that extracts of D. palmatum S. and D. ruyschiana L. growing in Yakutia contain a large number of polyphenols with biological activity [8,9,10,11,12]. At the same time, research on the chemical composition of D. jacutense Peschkova has not been carried out so far due to the rare occurrence of the species.
At present, there is a great interest in the search for plant composition of wild and cultivated ones that provide health benefits, such as functional foods. Among them, those of plant origin have a wide content of nutrients and phytochemical components with a variety of chemical structures with different physiological effects on the human body. The interest in natural antioxidants, especially from plant origin, has increased in recent years as well. Different plants contain high concentrations of bioactive compounds such as polyphenols, including anthocyanins, phenolic acids, tannins, carotenoids, vitamins A, C, and E, folic acid, and minerals such as calcium, selenium, and zinc. The dietary intake of polyphenols is suggested to prevent and lower the risk of chronic diseases.
Thus, the aim of this work is to conduct a comparative analysis of the chemical composition of the aerial parts (leaves + inflorescences + stems) of D. jacutense Peschkova collected both in the controlled grown conditions in the Botanical Garden of Yakutia and in the wild growing condition in the vicinity of the village of Sangar, Kobyaysky district of Yakutia (Figure 2A,B).

2. Materials and Methods

2.1. Plant Material

Aerial plant parts (leaves, stems, inflorescences) of Dracocephalum jacutense Peschkova were collected both from wild growing plants (during expedition work on the territory of the Kobyaysky district of Yakutia from 14 July to 19 July, 2022, N 63°53′52.5−72.8″; E 127°30′39.9−49″ and from introduced plants (in Botanical Garden of Yakutia, Yakutsk, N 62°02′42″; E 129°61′54″). The aerial parts (leaves + stems + inflorescences) were collected at the stage of full flowering of the plant. A few seeds were at the stage of milky ripeness and were husked (extracted) from inflorescences during processing before drying the aerial parts.

2.2. Chemicals and Reagents

HPLC-grade acetonitrile was purchased from Fisher Scientific (Southborough, UK), and MS-grade formic acid was from Sigma-Aldrich (Steinheim, Germany). Ultra-pure water was prepared from SIEMENS ULTRA clear (SIEMENS water technologies, Germany), and all other chemicals were analytical grade.

2.3. Fractional Maceration

Fractional maceration technique was applied to obtain highly concentrated extracts. From 500 g of the sample, 10 g of sample was randomly selected for maceration. The total amount of the extractant (ethyl alcohol of reagent grade) was divided into 3 parts, and the parts of plant were consistently infused with the first, second, and third parts. The solid–solvent ratio was 1:20. The infusion of each part of the extractant lasted 7 days at room temperature.

2.4. Liquid Chromatography

HPLC was performed using Shimadzu LC-20 Prominence HPLC (Shimadzu, Kyoto, Japan) equipped with a UV sensor and C18 silica reverse phase column (4.6 mm × 150 mm, particle size: 2.7 μm) to perform the separation of multicomponent mixtures. The gradient elution program with two mobile phases (A, deionized water; B, acetonitrile with formic acid 0.1% v/v) was as follows: 0–2 min, 0% B; 2–50 min, 0–100% B; control washing 50–60 min 100% B. The entire HPLC analysis was performed with a UV–vis detector SPD- 20A (Shimadzu, Kyoto, Japan) at a wavelength of 230 nm for identification compounds; the temperature was 50 °C, and the total flow rate was 0.25 mL min−1. The injection volume was 10 μL. Additionally, liquid chromatography was combined with a mass spectrometric ion trap to identify compounds.

2.5. Mass Spectrometry

MS analysis was performed on an ion trap amaZon SL (Bruker Daltoniks, Germany) equipped with an ESI source in negative and positive ion modes. The optimized parameters were obtained as follows: ionization source temperature: 70 °C, gas flow: 4 l/min, nebulizer gas (atomizer): 7.3 psi, capillary voltage: 4500 V, end plate bend voltage: 1500 V, fragmentary: 280 V, collision energy: 60 eV. A four-stage ion separation mode (MS/MS mode) was implemented.
MS analysis was supported by the Decree No. 220 by the Government of the Russian Federation (Mega-grant No 20-2961-3099)

3. Results

The extracts of both wild-grown and introduced D. jacutense aerial parts were analyzed by HPLS-MS/MS ion trap to better interpret the diversity of available phytochemicals. Extracts of the aerial plant part (inflorescences + leaves + stems) of wild and introduced plants were analyzed. Each type of extract showed a significant difference in the polyphenol composition, as well as in the compositions of other bioactive compounds. The structural identification of each compound was carried out on the basis of their accurate mass and MS/MS fragmentation by HPLC-ESI-ion trap-MS/MS. A total of 156 bioactive compounds were successfully characterized in extracts of D. jacutense based on their accurate MS fragment ions by searching online databases and the reported literature.
All the identified compounds, along with molecular formulas, MS/MS data, and their comparative profile for D. jacutense, are summarized in Table A1 (Appendix A). A total of 105 polyphenolic compounds and 51 compounds of other chemical groups were identified in extracts of wild D. jacutense and introduced D. jacutense, respectively, a total of 156 compounds. Of these, polyphenols in wild plant extracts are 70.2% (91 compounds), and in introduced plant extracts—65% (52 compounds). For example: some newly annotated polyphenols from the genus Dracocephalum are described below. The flavonol isorhamnetin was found in extracts from the leaves and flowers of D. jacutense. The CID-spectrum (collision-induced dissociation spectrum) in negative ion modes of isorhamnetin from extracts of D. jacutense is shown in Figure 3.
Figure 3. CID-spectrum of isorhamnetin from extracts of D. jacutense, m/z 315.
The [M–H]− ion produced one fragment ion at m/z 283 (Figure 3). The fragment ion with m/z 283 yields three daughter ions at m/z 189, m/z 163, and m/z 137. The fragment ion with m/z 163 yields a daughter ion at m/z 135. It was identified in the bibliography in extracts of Embelia [13], Rosmarinus officinalis [14], propolis [15], and Actinidia valvata [16].
The flavonol kaempferol-3,7-di-O-glucoside was found in extracts from flowers of D. jacutense. The CID-spectrum in positive ion modes of kaempferol-3,7-di-O-glucoside from extracts of D. jacutense is shown in Figure 4.
Figure 4. CID-spectrum of kaempferol-3,7-di-O-glucoside from extracts of D. jacutense, m/z 611.
The [M + H]+ ion produced two fragment ions at m/z 287 and m/z 449 (Figure 4). The fragment ion with m/z 287 yields four daughter ions at m/z 231, m/z 213, m/z 175, and m/z 137. The fragment ion with m/z 213 yields two daughter ions at m/z 185 and m/z 157. It was identified in the bibliography in extracts of tomato [17], rapeseed petals [18], Taraxacum officinale [19]. The anthocyanidin malonyl-shisonin was found in extracts from flowers of D. jacutense. The CID-spectrum in positive ion modes of malonyl-shisonin from extracts of D. jacutense is shown in Figure 5.
Figure 5. CID-spectrum of malonyl-shisonin from extracts of D. jacutense, m/z 843.
The [M + H]+ ion produced four fragment ion at m/z 287, m/z 595, m/z 535, and m/z 491 (Figure 5). The fragment ion with m/z 287 yields three daughter ions at m/z 259, m/z 213, and m/z 147. The fragment ion with m/z 213 yields one daughter ion at m/z 185. It was identified in the bibliography in extracts of Perilla frutescens [20,21].

4. Discussion

The identity between individual compounds in extracts of wild and introduced plants is found in 15 flavones, 5 flavanols, 2 flavan-3-ols, 5 flavanones, hydroxybenzoic acid, 4 phenolic acids, phenylpropanoic acid, lignan, dihydrochalcone, coumarin, coumarin glucoside, and anthocyanidin, the total for 38 polyphenolic compounds (Table 1). A total of 50 polyphenols were identified only in extracts of wild D. jacutense, for example: flavonoid (3,5-diacetyltambulin), isoflavone (apigenin 7-O-bets-D-(6-O-malonyl)-glucoside), isoflavanone (ferreirin), hydroxycoumarins (umbelliferone, umbelliferone hexoside), etc. A total of 14 polyphenols were identified only in the introduction of D. jacutense. Identity was also found between compounds presented in other groups; extracts of wild and introduced plants equally contain benzenediol, L-tryptophan, two omega-3-fatty acids, pterocarpan, oxylipin, an anabolic steroid, and two triterpene acids, a total of nine individual compounds from different groups.
Table 1. The distribution of polyphenol content in examples from Botanical Garden (Yakutsk) and in examples from Sangar (Kobyaysky district, Yakutia).
A total of 58.9% of compounds from other chemical groups (23 compounds) were identified in wild D. jacutense extracts alone, including purine (adenosine), an alkaloid (mesembrenol), diterpenoid naphthoquinone (tanshinone B), four hydroxy fatty acids (hydroxyoctadecadienoic acid, hydroxy eicosenoic acid, 13-trihydroxy-octadecenoic acid, trihydroxy eicosatetraenoic acid), sterol (stigmasterol), carotenoids (cryptoxanthin, zeaxanthin, (all-E)-β-cryptoxanthin laurate), etc. A total of 42,8% of compounds from other groups (12 compounds) were identified only in extracts of introduced D. jacutense: two diterpenoids, two triterpenes, indole sesquiterpene alkaloid, etc.
The similarity between extracts of wild and introduced D. jacutense was noted for 54 compounds that belong to 12 groups of polyphenols and 12 groups of other compounds. The full similarity in quantity and individual compounds for polyphenols was noted in the group of flavanones. Benzene diol, pterocarpan, vebonol, phenylpropanoic acid, dihydrochalcone, coumarin, coumarin glucoside, stearidonic and linolenic acids were found in other groups of compounds in both wild and introduced D. jacutense. The difference between the extracts of wild and introduced D. jacutense was noted for 103 individual compounds, including 13 groups of polyphenols and 24 groups of other compounds.
Polyphenols present only in extracts of wild D. jacutense have also been described in representatives of D. moldavica [22], mentha [23], S. officinalis [24], G. linguiforme, A. cordifolia [25] and D. palmatum [12]. Polyphenols present only in extracts of the introduced D. jacutense were found earlier in Jasminum urophyllum [26].
Other groups of compounds that were identified only in extracts of wild D. jacutense were also previously described in D. komarovi [27], Sarsaparilla [28], Sceletium [29], Rosa rugosa [30], Lonicera japonica [31], carotenoids [32], olive leaves [33], and D. palmatum [12]. Other groups of compounds that were identified only in extracts of introduced D. jacutense were previously found in D. komarovi [27], Rhus coriaria [34], olive leaves [33], and D. palmatum [12].
Flavones, flavonols, flavanones, and phenolic acids from polyphenolic compounds, identified in extracts of wild and introduced D. jacutense, were previously described in representatives of D. moldavica, D. palmatum, D. ruyschiana, Mentha, Eucalyptus, Rosmarinus, L. japonica, P. incarnata, Rh. coriaria, and C. kucha.

5. Conclusions

The results indicated a high variability between the wild and introduced D. jacutense samples in the number of polyphenolic compounds. In general, it can be summarized that wild-grown D. jacutense had 40 polyphenolic compounds and 11 compounds from other groups indicated richness than the introduced D. jacutense samples. Wild D. jacutense extracts contain 39.4% more flavones, 46.1% more flavanols, 50% more flavan-3-ols, 57.1% more phenolic acids, eight times more anthocyanidins than the introduced plant sample of D. jacutense which means that these could represent a potential source of compounds to develop new drugs for human health. In addition, wild-grown D. jacutense had two times higher many triterpene acids than the introduced one. In plant samples, certain profiles of polyphenols were described for the first time. A total of 56 polyphenols were found in D. jacutense that were not previously described in the genus Dracocephalum. Furthermore, 37 compounds of other chemical groups were identified that were not previously identified in the genus Dracocephalum. The plant will be preserved by the propagation of in vitro micropropagation protocol. In the past years, a growing demand for healthy food has been noted in the market. More recently, people have been primarily interested in plant composition, which is appealing and helps in preventing various diseases and contains high levels of promoted bioactive compounds. Our results could therefore be very useful for further clinical and nutritional studies on the polyphenol-rich plant D. jacutense.

Author Contributions

Conceptualization, M.P.R., Z.M.O.; methodology Z.G.R., P.S.E. and K.S.G.; software, M.P.R. and K.S.G.; validation, Z.M.O., M.P.R. and K.S.G.; formal analysis, M.P.R. and Z.M.O.; investigation, Z.M.O. and K.S.G.; resources, K.S.G.; data curation Z.G.R. and P.S.E.; writing—original draft preparation—M.P.R., Z.G.R. and Z.M.O.; writing—review and editing M.P.R.; S.E. and K.S.G.; visualization, M.P.R.; S.E. and Z.M.O.; supervision, K.S.G.; project administration, Z.M.O., K.S.G. All authors have read and agreed to the published version of the manuscript.

Funding

The study was carried out at the North-Eastern Federal University at the expense of the Russian Science Foundation Grant No. 22-14-20031, https://rscf.ru/en/project/22-14-20031/ and the Grant of the Yakut Science Foundation based on Agreement No. 194-06_22D.

Institutional Review Board Statement

No applicable.

Data Availability Statement

No applicable.

Conflicts of Interest

The authors declare no conflict of interest.

Appendix A

Table A1. Compounds identified from the extracts of D. jacutense in positive and negative ionization modes by HPLC-ion trap-MS/MS.
Table A1. Compounds identified from the extracts of D. jacutense in positive and negative ionization modes by HPLC-ion trap-MS/MS.
№Class of CompoundsIdentified CompoundsFormulaMassMolecular Ion [M-H]-Molecular Ion [M+H]+2 Fragmentation MS/MS 3 Fragmentation MS/MS 4 Fragmentation MS/MS References
POLYPHENOLS
1FlavoneFormononetin [Biochanin B; Formononetol] *C16H12O4268.2641 269213170; 156; 129141Astragali Radix [35,36,37]; Huolisu Oral Liquid [38]
2FlavoneApigenin [5,7-Dixydroxy-2-(40Hydroxyphenyl)-4H-Chromen-4-One]C15H10O5270.2369 269225181117Dracocephalum palmatum [8]; Dracocephalum [12]; Lonicera japonicum [31]; Andean blueberry [39]
3FlavoneAcacetin [Linarigenin; Buddleoflavonol]C16H12O5284.2635 285268211; 143 Dracocephalum palmatum [8]; Dracocephalum [12]; Dracocephalum moldavica [22]; Wissadula periplocifolia [40]
4FlavoneCalycosin [3′-Hydroxyformononetin] *C16H12O5284.2635 285253; 242; 225; 200235; 221; 209; 203 Astragali Radix [35,36,37]; Huolisu Oral Liquid [38]
5FlavoneGenkwanin [Gengkwanin; Puddumetin; Apigenin 7-Methyl Ether]C16H12O5284.2635 285165 Dracocephalum palmatum [8]; Rosmarinus officinalis [14]; Mentha [41]
6FlavoneLuteolinC15H10O6286.2363 287286; 153171153Dracocephalum palmatum [8]; Dracocephalum [12]; Lonicera japonicum [31]
7FlavoneDiosmetin [Luteolin 4′-Methyl Ether; Salinigricoflavonol]C16H12O6300.2629 301286258 Dracocephalum [12]; Dracocephalum moldavica [22]; Lonicera japonicum [31]; Andean blueberry [39]; Mentha [41]
8FlavoneChrysoeriol [Chryseriol]C16H12O6300.2629 301286; 167258203Dracocephalum palmatum [8]; Rhus coriaria [34]; Propolis [15]
9FlavoneHomoeriodictyol *C16H14O6302.2789 303285; 177163145Mentha [41]
10FlavoneCirsimaritin [Scrophulein; 4′,5-Dihydroxy-6,7-Dimethoxyflavone; 7-Methylcapillarisin] *C17H14O6314.2895 315282254226; 119Rosmarinus officinalis [14]; Ocimum [42]
11FlavoneDihydroxy-dimethoxy(iso)flavone *C17H14O6314.2895 315300; 272272257; 243; 217; 201; 185; 167Rosmarinus officinalis [14]; Propolis [15]; Astragali radix [36]
12Flavone5,7-Dimethoxyluteolin *C17H14O6314.2895313 285; 213; 185185; 145 Syzygium aromaticum [43]; Rosa rugosa [44]
13FlavoneMyricetin *C15H10O8318.2351 319291; 219; 143191; 143173Propolis [15]; Sanguisorba officinalis [24]; Andean blueberry [39]; millet grains [45]
14FlavoneIsothymusinC17H14O7330.2889 331303; 203203; 275203Dracocephalum palmatum [8]
15FlavoneCirsiliol *C17H14O7330.2889 331316; 298; 233; 157297; 187; 134 Ocimum [42]
16FlavoneDimethoxy-trihydroxy(iso)flavone *C17H14O7330.2889 331316; 226298; 226270; 226Propolis [15]; Jatropha [46]
17FlavoneNevadensinC18H16O7344.3154 345312; 241; 147284; 269269; 213; 135Dracocephalum [12]; Mentha [41]; Ocimum [42]
18FlavoneGardenin B [Demethyltangeretin] *C19H18O7358.342 359326; 298298270; 239; 162 Mentha [41]; Ocimum [42]; Actinocarya tibetica [47]
19FlavoneDihydroxy-tetramethoxy(iso)flavone *C19H18O8374.3414 375342313; 151299; 151Propolis [15]
20Flavone5-Hydroxy-6,7,8,3′,4′-pentamethoxyflavone *C20H20O8388.3680 389356313295; 221; 149Mentha [41]
21FlavoneApigenin O-hexosideC21H20O10432.3775431 269269; 225; 149224; 157Dracocephalum palmatum [8]; F. glaucescens; F. pottsii [25]; Chamaecrista nictitans [48]
22FlavoneApigenin-7-O-glucoside [Apigetrin; Cosmosiin]C21H20O10432.3775 433271153 Dracocephalum palmatum [8]; Mentha [23]; Dracocephalum [12]
23FlavoneAromadendrin 7-O-rhamnoside *C21H22O10434.3934433 287; 259; 229257; 227; 199; 157199Eucalyptus [49]; Zostera marina [50]
24FlavoneApigenin 7-O-glucuronideC21H18O11446.361 447271153271; 171Dracocephalum [12]; Perilla frutescens [20]; Eucalyptus Globulus [51]; Bougainvillea [52]
25FlavoneAcacetin 7-O-glucoside [Tilianin]C22H22O10446.4041 447285; 149270242Dracocephalum palmatum [8]; Dracocephalum [12]; Bougainvillea [52]
26FlavoneLuteolin 7-O-glucoside [Cynaroside; Luteoloside]C21H20O11448.3769 449287; 199153 Dracocephalum [12]; Lonicera japonicum [31]; Passiflora incarnata [53]
27Flavone3′-methoxyacacetin 7-O-beta-D-glucuronideC22H20O12476.3870475 374; 347; 275275; 247; 175247; 175; 147Dracocephalum moldavica [22]
28FlavoneAcacetin 7-O-beta-D-glucuronideC22H20O11460.3876 461270; 242; 153242 Dracocephalum [12]; Dracocephalum moldavica [22]
29Flavone6,4′-Dimethoxyisoflavone-7-O-glucoside *C23H24O10460.4307 461285270; 242; 153242Astragali radix [36]
30FlavoneDiosmetin-7-O-beta-glucosideC22H22O11462.4035 463287168123Dracocephalum [12]; Dracocephalum moldavica [22]; Oxalis corniculata [54]
31FlavoneApigenin-O-rhamnoside *C22H22O11462.4035 463273; 153153; 171171Passion fruit [55]
32FlavoneChrysoeriol-7-O-glucuronide *C22H20O12476.3870 477301286258Propolis [15]
33FlavoneAcacetin 7-beta-O-(6”-acetyl)-glucosideC24H24O11488.4408 489472; 354; 296; 223 Dracocephalum moldavica [22]
34IsoflavoneApigenin 7-O-beta-D-(6”-O-malonyl)-glucosideC24H22O13518.4237 519184; 500; 466; 371; 258125 Dracocephalum [12]; Dracocephalum moldavica [22]; Zostera marina [56]
35FlavoneAcacetin 7-O-beta-D-(6”-O-malonylated)-glucosideC25H24O13532.4503 533371; 285; 191; 165353; 285; 191; 165147Dracocephalum moldavica [22]
36FlavoneDiosmetin-7-O-beta-D-(6”-malonyl)-glucosideC25H24O14548.4497 549387; 285370; 272; 147328; 250; 208; 147Dracocephalum moldavica [22]
37FlavoneChrysoeriol O-hexoside C-hexoside *C28H32O16624.5441 625445; 463; 377; 347357; 217 Triticum aestivum L. [57,58]
38FlavoneIsovitexin 2”-O-glucoside-7-O-glucoside [Apigenin 6-C-glucoside 2”-O-glucoside-7-O-glucoside] *C33H40O20756.6587 757595; 569; 464; 347; 273577; 503; 431; 335; 242; 182 Passiflora incarnata [53]
39FlavonolKaempferol [3,5,7-Trihydroxy-2-(4-hydro- xyphenyl)-4H-chromen-4-one] C15H10O6286.2363 287269; 202233; 205216Dracocephalum [12]; Rapeseed petals [18]; Lonicera japonicum [31]; Rhus coriaria (Sumac) [34]; Andean blueberry [39]
40FlavonolQuercetinC15H10O7302.2357 303285; 228; 165229; 165141Propolis [15]; Actinidia valvata [16]; Rhus coriaria [34]; Potato leaves [59]
41FlavonolHerbacetin [3,5,7,8-Tetrahydroxy-2-(4-hydro- xyphenyl)-4H-chromen-4-one] * C15H10O7302.2357 303203; 275221 Ocimum [42]; Rhodiola rosea [60,61]
42FlavonolDihydroquercetin (Taxifolin; Taxifoliol)C15H12O7304.2516 305287286; 186185Dracocephalum [12]; Andean blueberry [39]; Eucalyptus [49];
43FlavonolIsorhamnetin [Isorhamnetol; Quercetin 3′-Methyl ether; 3-Methylquercetin] *C16H12O7316.2623 317299; 257; 214; 173281; 188 Embelia [13]; Rosmarinus officinalis [14]; Propolis [15]; Actinidia valvata [16]; Andean blueberry [39]
44Flavonoid3,5—Diacetyltambulin *C22H20O9428.3888427 381; 249249; 161161; 124A. cordifolia [25]
45FlavonolDihydrokaempferol-3-O-rhamnoside *C21H22O10434.3934 435287; 261259; 205187Vitis vinifera [62,63]
46FlavonolAstragalin [Kaempferol 3-O-glucoside; Kaempferol-3-Beta-Monoglucoside; Astragaline]C21H20O11448.3769447 285; 327241199Dracocephalum [12]; Lonicera japonicum [31]; Mexican lupine species [64]
47FlavonolQuercitrin [Quercetin 3-O- rhamnoside; Quercetrin] * C21H20O11448.3769 449302202; 174; 127175Embelia [13]; Propolis [15]; Rhus coriaria [34]; Bryophyllum pinnatum [54]; Euphorbia hirta [65]
48FlavonolKaempferol-3-O-glucuronideC21H18O12462.3604 463287268; 169241; 119Dracocephalum [12]; A. cordifolia; G. linguiforme [25]; Rhus coriaria [34]; Strawberry [55]
49FlavonolTaxifolin-3-O-hexoside [Dihydroquercetin-3-O-hexoside] *C21H22O12466.3922 467305; 259; 195; 153259; 195; 153231; 149Andean blueberry [39]; millet grains [45]; Euphorbia hirta [65] Actinidia deliciosa [66];
50FlavonolKaempferol 3-O-rutinosideC27H30O15594.5181 595287; 345; 389; 449287; 245; 153171Dracocephalum [12]; Lonicera japonicum [31]; Rhus coriaria [34];
51FlavonolKaempferol-3,7-Di-O-glucoside *C27H30O16610.5175 611287; 449287; 213; 185; 137185; 157Tomato [17]; Rapeseed petals [18]; Taraxacum officinale [19]
52FlavonolKaempferol dihexoside rhamnoside *C33H40O20756.6587 757595; 287287; 213; 137185; 168C. edulis [25]
53Flavan-3-ol(epi)Afzelechin *C15H14O5274.2687 275228; 210; 175; 157; 132212; 203; 183; 170194A. cordifolia; F. glaucescens; F. herrerae [25]; Cassia granidis [67]; Cassia abbreviata [68]
54Flavan-3-olCatechin [D-Catechol] *C15H14O6290.2681 291207; 123123 Vaccinium macrocarpon [69]; Vigna inguiculata [70]; Camellia kucha [71]; Actinidia [72]
55Flavan-3-ol(epi)catechinC15H14O6290.2681 291273; 117255; 145 Dracocephalum [12]; C. edulis [25]; Andean blueberry [39]
56Flavan-3-olGallocatechin [+(-)Gallocatechin]C15H14O7306.2675 307289259 Dracocephalum [12]; G. linguiforme [25]; Licania ridigna [73]; Rhodiola rosea [74]
57Flavan-3-ol(epi)Afzelechin derivative *C18H16O10392.3136 393275; 179191 Zostera marina [50]
58Flavan-3-olCatechin 3-O-gallate *C22H18O10442.3723 443273; 205263; 211; 171; 143 Vitis vinifera [62]; Camellia kucha [71]; Terminalia arjuna [75]
59Flavan-3-olEpigallocatechin-3-gallate *C22H18O11458.3717 459290; 207207; 123 F. glaucescens [25]; Vitis vinifera [62]; Camellia kucha [71]
60FlavanoneNaringenin [Naringetol; Naringenine]C15H12O5272.5228 273153; 256125 Dracocephalum palmatum [8]; Dracocephalum [12] Rapeseed petals [18]; Andean blueberry [39]
61FlavanoneEriodictyol [3′,4′,5,7-tetrahydroxy-flavanone]C15H12O6288.2522 289163; 271145117Dracocephalum palmatum [8]; Dracocephalum [12]; Mentha [23]; Andean blueberry [39]
62IsolavanoneFerreirinC16H14O6302.2789 303177; 285163135Mentha [23]
63FlavanonePrunin [Naringenin-7-O-glucoside]C21H22O10434.3934433 271; 151269; 151 Dracocephalum palmatum [8]; Dracocephalum [12]; Rapeseed petals [18]
64FlavanoneEriodictyol-7-O-glucoside [Pyracanthoside; Miscanthoside]C21H22O11450.3928449 285; 151243; 151 Dracocephalum [12]; Mentha [23]; Dracocephalum palmatum [7,8]
65FlavanoneEriodictyol-7-O-glucuronideC21H20O12464.3763463 285; 151285; 243; 151 Thymus vulgaris [76]; Mentha [77]
66Hydroxybenzoic acid Protocatechuic acidC7H6O4154.1201 155127117 Lonicera japonicum [31]; Rhus coriaria [34]; Eucalyptus Globulus [51]; Vaccinium macrocarpon [69]; Actinidia [72]
67Hydroxycinnamic acidp-Coumaric acid [4-Hydroxycinnamic acid; P-Hydroxycinnamic acid; 4-Coumarate]C9H8O3164.1580 165147119 Rapeseed petals [18]; F. pottsii [25]; Rhus coriaria [34]; Andean blueberry [39]; Brazilian propolis [78]
68Hydroxycinnamic acidCaffeic acidC9H8O4180.1574 181135119 Dracocephalum palmatum [8]; Dracocephalum [12]; Eucalyptus [49]
69Hydroxycinnamic acid3,4-Dihydroxyhydrocinnamic acidC9H10O4182.1733 183137 Eucalyptus Globulus [51]
70Phenolic acid2,3,4,5-Tetrahydroxybenzoic acid [2-Hydroxygallussaure; 3,4,5-Trihydroxysalicylic acid]C7H6O6186.1189 187144 PubChem
71Phenolic acidSalvianic acid A [Danshensu]C9H10O5198.1727197 179; 135135 Huolisu Oral Liquid [38]; Mentha [77]; Hedyotis diffusa [79]
72Phenolic acid2,3-Dihydroxy-4-Mathoxycinnamic acidC10H10O5210.1834 211192; 134134; 174 A. cordifolia [25]
73Hydroxybenzoic acidEllagic acid [Benzoaric acid; Elagostasine; Lagistase; Eleagic acid]C14H6O8302.1926301 284221112Dracocephalum [12]; Rhus coriaria [34]; Eucalyptus [49]; Eucalyptus Globulus [51]
74Phenolic acidProtocatechuic acid-O-hexosideC13H16O9316.2607315 153; 123123 Rhus coriaria [34]; Eucalyptus Globulus [51]; Euphorbia hirta [65]
75Phenolic acidSalvianolic acid GC18H12O7340.2837 341296; 208278; 208235; 164Dracocephalum [12]; Mentha [41]; Salvia miltiorrhiza [80]
76Phenolic acidCaffeic acid-4-O-beta-D-hexoside [Caffeoyl-O-hexoside]C15H18O9342.298341 179; 119143; 131 Dracocephalum [12]; Cherimoya, papaya [55]; Sasa veitchii [81]
77Phenolic acidChlorogenic acid [3-O-Caffeoylquinic acid]C16H18O9354.3087 355179; 338; 227127 Dracocephalum palmatum [8]; Rapeseed petals [18]; Lonicera japonicum [31]; Rhus coriaria [34]; Andean blueberry [39]
78Phenolic acidIsochlorogenic acidC16H18O9354.3087 355323; 269; 165295; 208; 133295; 249; 221Actinidia [72]
79Phenolic acidRosmarinic acidC18H16O8360.3148359 161133 Dracocephalum palmatum [8]; Dracocephalum [12]; Mentha [41]; Zostera marina [56]; Salvia miltiorrhiza [80]; Lepechinia [82]
80 3-Prenyl-4-(dihydrocinnamoyloxy)-cinnamic acidC23H24O4364.4343 365261; 185233; 179179; 151Brazilian propolis [78]
81Phenolic acidCaffeic acid derivativeC16H18O9Na377.2985377 341; 215179 Dracocephalum [12]; Bougainvillea [52]
82Phenolic acid1/3/4/5-p-Coumaroylquinic acid +C2H2OC18H20O9380.3460 381321; 275; 233260; 218; 143 Actinidia [72]
83Phenolic acid8,8′-Aryl-Diferulic acidC20H18O8386.3521385 193; 285193; 161 millet grains [45]
84Phenolic acidCaffeic acid hexoside dimerC31H40O17684.6391683 341179; 161143Strawberry, Lemon, Cherimoya, Passion fruit [55]
85Phenolic acidDidehydrosalvianolic acid BC36H28O16716.5979 717574319; 263; 187299; 177Mentha [77]
86Phenolic acidSalvianolic acid B [Danfensuan B]C36H30O16718.6138717 519; 321321; 279279; 185Huolisu Oral Liquid [38]; Bougainvillea [52]; Mentha [77]; Salvia miltiorrhiza [80]
87Phenylpropanoic acid Sagerinic acidC36H32O16720.6297719 359161; 197133Dracocephalum palmatum [8]; Rosmarinus officinalis [14]; Perilla frutescens [20]; Huolisu Oral Liquid [38]; Mentha [41]
88Phenolic acidClerodendranoic acid HC36H32O16720.6297719 359161 Lepechinia [82];
89LignanPhillygenin [Sylvatesmin; Phyllygenol; Forsythigenol]C21H24O6372.4117371 163; 325119 Lignans [83]
90LignanMedioresinolC21H24O7388.4111387 207; 163; 119163 Rosmarinus officinalis [14]; Lignans [83]; Punica granatum [84]
91NeolignanUrolignoside + H2OC25H34O11510.5309 511493; 451; 421; 349; 285349; 254; 147331; 289; 259Jasminum urophyllum [26]; Actinidia [72]
92DihydrochalconePhloretin [Dihydronaringenin; Phloretol]C15H14O5274.2687 275255; 229; 131237; 209; 164 G. linguiforme [25]; Rosa rugosa [44]; Punica granatum [84]
93HydroxycoumarinUmbelliferone [Skimmetin; Hydragin]C9H6O3162.1421 163145; 135; 117117 Sanguisorba officinalis [24]; F. glaucescens [25]; Zostera marina [50]; Actinidia [72]
94CoumarinFraxetin [7,8-Dihydroxy-6-methoxycoumarin]C10H8O5208.1675 209191; 149149147Embelia [13]; Jatropha [46]; Actinidia [72];
95HydroxycoumarinUmbelliferone hexosideC15H16O8324.2827 325307; 288; 271; 253; 241127; 118 G. linguiforme [25]
96Coumarin glycoside Fraxin (Fraxetin-8-O-glucoside)C16H18O10370.3081 371209 Rosa rugosa [44]; Actinidia [72]
97AnthocyanidinPetunidinC16H13O7+317.2702 318166; 300121 Dracocephalum [12]; A. cordifolia; C. edulis [21]
98AnthocyanidinPelargonidin-3-O-glucoside (callistephin)C21H21O10433.3854 433271153; 225171Dracocephalum [12]; Triticum aestivum [85]; Rubus ulmifolius [86]
99AnthocyanidinCyanidin-3-O-glucoside [Cyanidin 3-O-beta-D-Glucoside; Kuromarin]C21H21O11+449.3848 449287153 Dracocephalum [12]; Triticum aestivum [85]; Malpighia emarginata [87]
100AnthocyanidinCyanidin 3,5-O-diglucosideC27H31O16611.5335 611287; 449287; 241; 213; 175; 149213; 185; 172; 157; 145Rapeseed petals [18]; Muscadine pomace [88]; Berberis microphylla [89]
101AnthocyanidinPeonidin-3,5-diglucoside [Peonin; Peonidin 3-Glucoside-5-Glucoside]C28H33O16625.5520 625463; 374; 301445; 373 Triticum aestivum [85]; Muscadine pomace [88]
102AnthocyanidinCyanidin-3-O-rutinoside-5-O-glucosideC33H41O20757.6666 757287; 449; 595287; 213; 137185Camellia kucha [71]; Solanium nigrum [9]
103AnthocyanidinDelphinidin 3-O-rutinoside-5-O-glucosideC33H41O21773.5769 773303; 465; 611257; 303; 229; 165257; 229; 201; 116Berberis microphylla [89]; Solanium nigrum [90]; Iris dichotoma [91]
104AnthocyanidinMalonyl-shisoninC39H39O21+843.7144 843595; 535; 491; 287287; 259; 213; 147213; 185Perilla frutescens [20,21]
OTHERS
105BenzenediolCatechol derivativeC6H6O3126.1100 127124; 118 Embelia [13];
106Alkyl cinnamateMethyl cinnamate [Methyl 3-Phenylacrilate]C10H10O2162.1852 164144 Strawberry [92]
107Amino acidPhenylalanine [L-Phenylalanine]C9H11NO2165.1891 166147; 120 Rapeseed petals [18]; Lonicera japonica [31]; Passiflora incarnata [53]; Potato leaves [59]
108Amino acidTyrosine [(2S)-2-Amino-3-(4-Hydroxyphnyl)Propanoic acid]C9H11NO3181.1885 182165; 150113 Euphorbia hirta [65]; Vigna unguiculata [93]; Hylocereus polyrhizus [94]
109Monobasic carboxylic acidHydroxyphenyllactic acidC9H10O4182.1733181 163; 135119 Mentha [95]
110Amino acidL-Tryptophan [Tryptophan; (S)-Tryptophan]C11H12N2O2204.2252 205188144118Dracocephalum [12]; Rapeseed petals [18]; Huolisu Oral Liquid [38]; Rosa acicularis [44]
111Aminoalkylindole5-MethoxydimethyltryptamineC13H18N2O218.2948 219201159; 118 Dracocephalum [12]; Camellia kucha [71]
112Omega-5 fatty acidMyristoleic acid [Cis-9-Tetradecanoic acid]C14H26O2226.3550 227209139 Dracocephalum [12]; F. glaucescens [25]
113GermacranolideCostunolideC15H20O2232.3181 233187; 215145143Rosa davurica [44]; Weichang’an Pill [96]
114Medium-chain fatty acidHydroxy myristic acid [2S-Hydroxytetradecanoic acid; Alpha-Hydroxy Myristic acid]C14H28O3244.3703 246228; 159199; 172144F. pottsii [25]
115XanthoneMangiferitin [Norathyriol; 1,3,6,7-Tetrahydroxyxanthone]C13H8O6260.1990 261193; 135179; 124111Rhus coriaria [34]
116Aporphine alkaloidAnonaineC17H15NO2265.3065 266248; 171; 122229; 182; 116212; 182Rosa rugosa [44]; Magnolia [97]
117Ribonucleoside composite of adenine (purine)AdenosineC10H13N5O4267.2413 268136; 258 Dracocephalum [12]; Lonicera japonica [31]
118Omega 3-fatty acidStearidonic acid [6,9,12,15-Octadecatetraenoic acid; Moroctic acid]C18H28O2276.4137 277177; 247175 G. linguiforme [25]; Rhus coriaria [34]; Jatropha [46]; Salvia Miltiorrhiza [80]
119Omega 3-fatty acidLinolenic acid (Alpha-Linolenic acid; Linolenate)C18H30O2278.4296 279219; 259159 Jatropha [46]; Salvia Miltiorrhiza [80]; Pinus sylvestris [98]
120Fatty amideLinoleic acid amideC18H33NO279.4607 280262; 244244; 234; 216; 196; 172196; 168; 151Propolis [15]; Rhus coriaria [34]
121Fatty amideOleamideC18H35NO281.4766 282263; 246; 192245; 228; 217; 197; 170 Propolis [15]
122AlkaloidMesembrenolC17H23NO3289.3694 290242; 122184; 149 Dracocephalum [12]; Sceletium [29]
123Diterpenoid naphthoquinoneTanshinone IIA [Tanshinone II; Tanshinone B]C19H18O3294.3444 295277; 259; 193; 149259; 241; 199; 149241; 147Huolisu Oral Liquid [38]
124Unsaturated hydroxy fatty acidHydroxyoctadecatrienoic acidC18H30O3294.4290293 275; 235; 185; 172231; 205; 177231; 163Jatropha [46]
125Polyunsaturated fatty acidAlpha-Kamlolenic Acid [18-Hydroxy-9Z,11E,13E- Octadecatrienoic Acid]C18H30O3294.4290293 275; 231; 171231; 177231G. linguiforme; F. glaucescens; F. pottsii [25]
126Essential fatty acidHydroxyoctadecadienoic acidC18H32O3296.4449295 277; 251; 195; 171; 152233; 179; 155 A. cordifolia; F. glaucescens; F. herrerae [25]; Jatropha [46]
127Pterocarpan3-Hydroxy-9,10-dimethoxypterocarpanC17H16O5300.3059 301286; 257; 229; 177; 153163; 149145Astragali radix [36]; Huolisu Oral Liquid [38]
128DiterpenoidTanshinone IIB [(S)-6-(Hydroxymethyl)-1,6-Dimethyl-6,7,8,9-Tetrahydrophenanthro [1,2-B]Furan-10,11-Dione]C19H18O4310.3438 311283; 137119 Huolisu Oral Liquid [38]; Salvia Miltiorrhiza [80]
129 p-hydroxyphenacyl-β-D-glucopyranosideC14H18O8314.2879313 161; 213133; 161133Rhodiola crenulata [99]
130Long-chain fatty acidHydroxy eicosenoic acidC20H38O3326.5139 327295; 268; 181; 125268237; 135A. cordifolia; F. pottsii [25]
131 Fructose-phenylalanineC15H21NO7327.3297 328310; 292292; 264; 244; 216; 198; 178244; 216; 198; 171; 156Potato leaves [59]
132Oxylipins9,10-Dihydroxy-8-oxooctadec-12-enoic acid [oxo-DHODE; oxo-Dihydroxy-octadecenoic acid]C18H32O5328.4437327 229209183Dracocephalum [12]; Phyllostachys nigra [81]; Bituminaria [100]
133Oxylipins13- Trihydroxy-Octadecenoic acid [THODE]C18H34O5330.4596329 229; 293; 211; 171211; 229; 155183; 211Dracocephalum [12]; Sasa veitchii [81]; Bituminaria [100]
134Unsaturated essential fatty acidDihydroxy eicosatrienoic acidC20H34O4338.4816 339321; 177; 145145117G. linguiforme; A. cordifolia; C. edulis [25]
135DiterpenoidKomarovinone AC21H28O4344.4446 345312; 240284; 121268; 135Dracocephalum komarovi [27]
136TriterpeneDracocephalone AC20H26O5346.4174 347319; 287; 219219191Dracocephalum komarovi [27]
137Unsaturated omega-3 fatty acidTrihydroxy eicosatetraenoic acidC20H32O5352.4651 353261; 293; 243; 207243; 201; 159; 132162F. glaucescens [25]
138Tetracyclic diterpenoidKomaroviquinoneC21H28O5360.4440 361343; 302310; 269; 218; 161282Dracocephalum komarovi [27]
139TriterpeneSqualene (Trans-Squalene; Spinacene; Supraene)C30H50410.718 411393; 36; 291; 244; 198 Olive leaves [33]; squalene [101]
140SterolStigmasterol [Stigmasterin; Beta-Stigmasterol]C29H48O412.6908 413395; 301; 237; 189189 Dracocephalum [12]; A.cordifolia; F. pottsii [25]; Olive leaves [33]; Hedyotis diffusa [79]
141Anabolic steroid; Androgen; Androgen esterVebonolC30H44O3452.6686 453435; 336; 226336209Dracocephalum [12]; Rhus coriaria [34]; Hylocereus polyrhizus [94]
142Triterpenic acidBetulonic acid [Betunolic acid; Liquidambaric acid]C30H46O3454.6844 455436; 353; 313; 249393; 336; 319; 282154Rhus coriaria [34]; Rosa rugosa [44]
143Triterpenic acid1-Hydroxy-3-oxours-12-en-28-oic acidC30H46O4470.6838 471453; 425; 407; 389365; 335; 283; 205177; 121Pear [102]
144Triterpenic acidPomolic acidC30H48O4472.6997 473454; 371; 302; 144 Sanguisorba officinalis [24]; Pear [102]; Malus domestica [103]
145Triterpenic acidTormentic acid [Jacarandic acid; Tomentic acid]C30H48O5488.6991487 470; 423; 372403; 377 Sanguisorba officinalis [24]; Actinidia [72]; Pear [102]
146Monoterpene glycosideRhodioloside C [(2E,4R)-4-hydroxy-3,7-dimethyl-2,6-octadienyl β-D-glucopyranosyl(1-3)-β-D-glucopyranoside] C22H38O12494.5299493 447; 329; 285309; 285294; 187Rhodiola crenulata [99]; Rhodiola rosea [104,105,106]
147Carotenoid(all-E)-lutein 3′-O-myristateC40H54O550.8562 551533; 509; 429; 385; 355133 Rosa rugosa [30]; Carotenoids [107]
148Indole sesquiterpene alkaloidSespendoleC33H45NO4519.7147 520184; 359124 Dracocephalum [12]; Rhus coriaria [34]; Hylocereus polyrhizus [94]
149CarotenoidCryptoxanthin [Beta-cryptoxanthin]C40H56O552.872 553535; 325; 223517 Dracocephalum [12]; Sarsaparilla [28]; Carotenoids [107,108];
150CarotenoidZeaxanthin [All-Trans-Zexanthin; Anchovyxanthin]C40H56O2568.8714 569553; 534; 471; 359534; 486; 326; 262516; 473; 308; 262Sarsaparilla [28]; Carotenoids [107]; orange juice [109]
151Product of chlorophyll breakdownPheophorbide aC35H34N4O6606.6677 607547; 503; 461461; 433433Product of Chlorophylle breakdown [110]
152CycloartanolCyclopassifloic acid glucosideC37H62O12698.8810 699537375; 331; 259; 185 Passiflora incarnata [53]
153CarotenoidCarotenoidC41H59O10711.9012 712695; 605; 543; 474; 456412; 369; 200; 143 Carotenoids [32]
154Carotenoid(all-E)-beta-cryptoxanthin laurate [Beta-Cryptoxanthin-Laurate]C52H78O2735.1745 735323; 521; 277295; 163249; 173; 134Sarsaparilla [28]; Carotenoids [107]; Carica papaya [111]
155Product of chlorophyll degradationPheophytin AC55H74N4O5871.1999 593; 533533; 461461; 433Product of Chlorophylle breakdown [110]; Physalis peruviana [112]; Capsicum [113]
* Compounds, firstly identified in genus Dracocephalum.

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