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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).

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).

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.

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.

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.

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.

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.

 Institutional Review Board Statement

No applicable.

 Informed Consent Statement

No applicable.

 Data Availability Statement

No applicable.

 Conflicts of Interest

The authors declare no conflict of interest.

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Figures and Table
View Image - Figure 1. Collection areas for wild and introduced D. jacutense Peshkova.Enlarge this image.

Figure 1. Collection areas for wild and introduced D. jacutense Peshkova.

View Image - 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).Enlarge this image.

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).

View Image - Figure 3. CID-spectrum of isorhamnetin from extracts of D. jacutense, m/z 315.Enlarge this image.

Figure 3. CID-spectrum of isorhamnetin from extracts of D. jacutense, m/z 315.

View Image - Figure 4. CID-spectrum of kaempferol-3,7-di-O-glucoside from extracts of D. jacutense, m/z 611.Enlarge this image.

Figure 4. CID-spectrum of kaempferol-3,7-di-O-glucoside from extracts of D. jacutense, m/z 611.

View Image - Figure 5. CID-spectrum of malonyl-shisonin from extracts of D. jacutense, m/z 843.Enlarge this image.

Figure 5. CID-spectrum of malonyl-shisonin from extracts of D. jacutense, m/z 843.

The distribution of polyphenol content in examples from Botanical Garden (Yakutsk) and in examples from Sangar (Kobyaysky district, Yakutia).

№ Class of Compounds Identified Compounds Formula Botanical Garden of Yakutsk Wild Specimens
1 Flavone Formononetin * C16H12O4
2 Flavone Apigenin C15H10O5
3 Flavone Acacetin C16H12O5
4 Flavone Calycosin C16H12O5
5 Flavone Gengkwanin C16H12O5
6 Flavone Luteolin C15H10O6
7 Flavone Diosmetin C16H12O6
8 Flavone Chrysoeriol [Chryseriol] C16H12O6
9 Flavone Homoeriodictyol * C16H14O6
10 Flavone Cirsimaritin * C17H14O6
11 Flavone Dihydroxy-dimethoxy(iso)flavone * C17H14O6
12 Flavone 5,7-Dimethoxyluteolin * C17H14O6
13 Flavone Myricetin * C15H10O8
14 Flavone Isothymusin C17H14O7
15 Flavone Cirsiliol * C17H14O7
16 Flavone Dimethoxy-trihydroxy(iso)flavone * C17H14O7
17 Flavone Nevadensin C18H16O7
18 Flavone Gardenin B [Demethyltangeretin] * C19H18O7
19 Flavone Dihydroxy-tetramethoxy(iso)flavone * C19H18O8
20 Flavone 5-Hydroxy-6,7,8,3′,4′-pentamethoxyflavone * C20H20O8
21 Flavone Apigenin O-hexoside C21H20O10
22 Flavone Apigenin-7-O-glucoside C21H20O10
23 Flavone Aromadendrin 7-O-rhamnoside * C21H22O10
24 Flavone Apigenin 7-O-glucuronide C21H18O11
25 Flavone Acacetin 7-O-glucoside [Tilianin] C22H22O10
26 Flavone Luteolin 7-O-glucoside [Cynaroside; Luteoloside] C21H20O11
27 Flavone 3′-methoxyacacetin 7-O-beta-D-glucuronide C22H20O12
28 Flavone Acacetin 7-O-beta-D-glucuronide C22H20O11
29 Flavone 6,4′-Dimethoxyisoflavone-7-O-glucoside * C23H24O10
30 Flavone Diosmetin-7-O-beta-glucoside C22H22O11
31 Flavone Apigenin-O-rhamnoside * C22H22O11
32 Flavone Chrysoeriol-7-O-glucuronide * C22H20O12
33 Flavone Acacetin 7-beta-O-(6”-acetyl)-glucoside C24H24O11
34 Isoflavone Apigenin 7-O-beta-D-(6”-O-malonyl)-glucoside C24H22O13
35 Flavone Acacetin 7-O-beta-D-(6”-O-malonylated)-glucoside C25H24O13
36 Flavone Diosmetin-7-O-beta-D-(6”-malonyl)-glucoside C25H24O14
37 Flavone Chrysoeriol O-hexoside C-hexoside * C28H32O16
38 Flavone Isovitexin 2”-O-glucoside-7-O-glucoside * C33H40O20
39 Flavonol Kaempferol C15H10O6
40 Flavonol Quercetin C15H10O7
41 Flavonol Herbacetin * C15H10O7
42 Flavonol Dihydroquercetin (Taxifolin; Taxifoliol) C15H12O7
43 Flavonol Isorhamnetin C16H12O7
44 Flavonoid 3,5—Diacetyltambulin * C22H20O9
45 Flavonol Dihydrokaempferol-3-O-rhamnoside * C21H22O10
46 Flavonol Astragalin C21H20O11
47 Flavonol Quercitrin [Quercetin 3-O- rhamnoside; Quercetrin] * C21H20O11
48 Flavonol Kaempferol-3-O-glucuronide C21H18O12
49 Flavonol Taxifolin-3-O-hexoside [Dihydroquercetin-3-O-hexoside] * C21H22O12
50 Flavonol Kaempferol 3-O-rutinoside C27H30O15
51 Flavonol Kaempferol-3,7-Di-O-glucoside * C27H30O16
52 Flavonol Kaempferol dihexoside rhamnoside * C33H40O20
53 Flavan-3-ol (epi)Afzelechin * C15H14O5
54 Flavan-3-ol Catechin [D-Catechol] * C15H14O6
55 Flavan-3-ol (epi)catechin C15H14O6
56 Flavan-3-ol Gallocatechin * C15H14O7
57 Flavan-3-ol (epi)Afzelechin derivative * C18H16O10
58 Flavan-3-ol Catechin 3-O-gallate * C22H18O10
59 Flavan-3-ol Epigallocatechin-3-gallate C22H18O11
60 Flavanone Naringenin C15H12O5
61 Flavanone Eriodictyol C15H12O6
62 Isoflavanone Ferreirin * C16H14O6
63 Flavanone Prunin C21H22O10
64 Flavanone Eriodictyol-7-O-glucoside C21H22O11
65 Flavanone Eriodictyol-7-O-glucuronide * C21H20O12
66 Hydroxybenzoic acid Protocatechuic acid * C7H6O4
67 Hydroxycinnamic acid p-Coumaric acid C9H8O3
68 Hydroxycinnamic acid Caffeic acid C9H8O4
69 Hydroxycinnamic acid 3,4-Dihydroxyhydrocinnamic acid * C9H10O4
70 Phenolic acid 2,3,4,5-Tetrahydroxybenzoic acid C7H6O6
71 Phenolic acid Salvianic acid A [Danshensu] * C9H10O5
72 Phenolic acid 2,3-Dihydroxy-4-Mathoxycinnamic acid * C10H10O5
73 Hydroxybenzoic acid Ellagic acid C14H6O8
74 Phenolic acid Protocatechuic acid-O-hexoside * C13H16O9
75 Phenolic acid Salvianolic acid G C18H12O7
76 Phenolic acid Caffeic acid-4-O-beta-D-hexoside [Caffeoyl-O-hexoside] C15H18O9
77 Phenolic acid Chlorogenic acid [3-O-Caffeoylquinic acid] C16H18O9
78 Phenolic acid Isochlorogenic acid * C16H18O9
79 Phenolic acid Rosmarinic acid C18H16O8
80 3-Prenyl-4-(dihydrocinnamoyloxy)-cinnamic acid * C23H24O4
81 Phenolic acid Caffeic acid derivative C16H18O9Na
82 Phenolic acid 1/3/4/5-p-Coumaroylquinic acid * + C2H2O C18H20O9
83 Phenolic acid 8,8′-Aryl-Diferulic acid * C20H18O8
84 Phenolic acid Caffeic acid hexoside dimer * C31H40O17
85 Phenolic acid Didehydrosalvianolic acid B * C36H28O16
86 Phenolic acid Salvianolic acid B [Danfensuan B] * C36H30O16
87 Phenylpropanoic acid Sagerinic acid C36H32O16
88 Phenolic acid Clerodendranoic acid H * C36H32O16
89 Lignan Phillygenin [Sylvatesmin; Phyllygenol; Forsythigenol] * C21H24O6
90 Lignan Medioresinol * C21H24O7
91 Neolignan Urolignoside * + H2O C25H34O11
92 Dihydrochalcone Phloretin * C15H14O5
93 Hydroxycoumarin Umbelliferone * C9H6O3
94 Coumarin Fraxetin * C10H8O5
95 Hydroxycoumarin Umbelliferone hexoside * C15H16O8
96 Coumarin glycoside Fraxin (Fraxetin-8-O-glucoside) C16H18O10
97 Anthocyanidin Petunidin C16H13O7+
98 Anthocyanidin Pelargonidin-3-O-glucoside (callistephin) C21H21O10
99 Anthocyanidin Cyanidin-3-O-glucoside C21H21O11+
100 Anthocyanidin Cyanidin 3,5-O-diglucoside * C27H31O16
101 Anthocyanidin Peonidin-3,5-diglucoside * C28H33O16
102 Anthocyanidin Cyanidin-3-O-rutinoside-5-O-glucoside * C33H41O20
103 Anthocyanidin Delphinidin 3-O-rutinoside-5-O-glucoside * C33H41O21
104 Anthocyanidin Malonyl-shisonin * C39H39O21+

* Polyphenols firstly annotated in genus Dracocephalum.

Appendix A

Compounds identified from the extracts of D. jacutense in positive and negative ionization modes by HPLC-ion trap-MS/MS.

№ Class of Compounds Identified Compounds Formula Mass Molecular Ion [M-H]- Molecular Ion [M+H]+ 2 Fragmentation MS/MS 3 Fragmentation MS/MS 4 Fragmentation MS/MS References
POLYPHENOLS
1 Flavone Formononetin [Biochanin B; Formononetol] * C16H12O4 268.2641 269 213 170; 156; 129 141 Astragali Radix [35,36,37]; Huolisu Oral Liquid [38]
2 Flavone Apigenin [5,7-Dixydroxy-2-(40Hydroxyphenyl)-4H-Chromen-4-One] C15H10O5 270.2369 269 225 181 117 Dracocephalum palmatum [8]; Dracocephalum [12]; Lonicera japonicum [31]; Andean blueberry [39]
3 Flavone Acacetin [Linarigenin; Buddleoflavonol] C16H12O5 284.2635 285 268 211; 143 Dracocephalum palmatum [8]; Dracocephalum [12]; Dracocephalum moldavica [22]; Wissadula periplocifolia [40]
4 Flavone Calycosin [3′-Hydroxyformononetin] * C16H12O5 284.2635 285 253; 242; 225; 200 235; 221; 209; 203 Astragali Radix [35,36,37]; Huolisu Oral Liquid [38]
5 Flavone Genkwanin [Gengkwanin; Puddumetin; Apigenin 7-Methyl Ether] C16H12O5 284.2635 285 165 Dracocephalum palmatum [8]; Rosmarinus officinalis [14]; Mentha [41]
6 Flavone Luteolin C15H10O6 286.2363 287 286; 153 171 153 Dracocephalum palmatum [8]; Dracocephalum [12]; Lonicera japonicum [31]
7 Flavone Diosmetin [Luteolin 4′-Methyl Ether; Salinigricoflavonol] C16H12O6 300.2629 301 286 258 Dracocephalum [12]; Dracocephalum moldavica [22]; Lonicera japonicum [31]; Andean blueberry [39]; Mentha [41]
8 Flavone Chrysoeriol [Chryseriol] C16H12O6 300.2629 301 286; 167 258 203 Dracocephalum palmatum [8]; Rhus coriaria [34]; Propolis [15]
9 Flavone Homoeriodictyol * C16H14O6 302.2789 303 285; 177 163 145 Mentha [41]
10 Flavone Cirsimaritin [Scrophulein; 4′,5-Dihydroxy-6,7-Dimethoxyflavone; 7-Methylcapillarisin] * C17H14O6 314.2895 315 282 254 226; 119 Rosmarinus officinalis [14]; Ocimum [42]
11 Flavone Dihydroxy-dimethoxy(iso)flavone * C17H14O6 314.2895 315 300; 272 272 257; 243; 217; 201; 185; 167 Rosmarinus officinalis [14]; Propolis [15]; Astragali radix [36]
12 Flavone 5,7-Dimethoxyluteolin * C17H14O6 314.2895 313 285; 213; 185 185; 145 Syzygium aromaticum [43]; Rosa rugosa [44]
13 Flavone Myricetin * C15H10O8 318.2351 319 291; 219; 143 191; 143 173 Propolis [15]; Sanguisorba officinalis [24]; Andean blueberry [39]; millet grains [45]
14 Flavone Isothymusin C17H14O7 330.2889 331 303; 203 203; 275 203 Dracocephalum palmatum [8]
15 Flavone Cirsiliol * C17H14O7 330.2889 331 316; 298; 233; 157 297; 187; 134 Ocimum [42]
16 Flavone Dimethoxy-trihydroxy(iso)flavone * C17H14O7 330.2889 331 316; 226 298; 226 270; 226 Propolis [15]; Jatropha [46]
17 Flavone Nevadensin C18H16O7 344.3154 345 312; 241; 147 284; 269 269; 213; 135 Dracocephalum [12]; Mentha [41]; Ocimum [42]
18 Flavone Gardenin B [Demethyltangeretin] * C19H18O7 358.342 359 326; 298 298 270; 239; 162 Mentha [41]; Ocimum [42]; Actinocarya tibetica [47]
19 Flavone Dihydroxy-tetramethoxy(iso)flavone * C19H18O8 374.3414 375 342 313; 151 299; 151 Propolis [15]
20 Flavone 5-Hydroxy-6,7,8,3′,4′-pentamethoxyflavone * C20H20O8 388.3680 389 356 313 295; 221; 149 Mentha [41]
21 Flavone Apigenin O-hexoside C21H20O10 432.3775 431 269 269; 225; 149 224; 157 Dracocephalum palmatum [8]; F. glaucescens; F. pottsii [25]; Chamaecrista nictitans [48]
22 Flavone Apigenin-7-O-glucoside [Apigetrin; Cosmosiin] C21H20O10 432.3775 433 271 153 Dracocephalum palmatum [8]; Mentha [23]; Dracocephalum [12]
23 Flavone Aromadendrin 7-O-rhamnoside * C21H22O10 434.3934 433 287; 259; 229 257; 227; 199; 157 199 Eucalyptus [49]; Zostera marina [50]
24 Flavone Apigenin 7-O-glucuronide C21H18O11 446.361 447 271 153 271; 171 Dracocephalum [12]; Perilla frutescens [20]; Eucalyptus Globulus [51]; Bougainvillea [52]
25 Flavone Acacetin 7-O-glucoside [Tilianin] C22H22O10 446.4041 447 285; 149 270 242 Dracocephalum palmatum [8]; Dracocephalum [12]; Bougainvillea [52]
26 Flavone Luteolin 7-O-glucoside [Cynaroside; Luteoloside] C21H20O11 448.3769 449 287; 199 153 Dracocephalum [12]; Lonicera japonicum [31]; Passiflora incarnata [53]
27 Flavone 3′-methoxyacacetin 7-O-beta-D-glucuronide C22H20O12 476.3870 475 374; 347; 275 275; 247; 175 247; 175; 147 Dracocephalum moldavica [22]
28 Flavone Acacetin 7-O-beta-D-glucuronide C22H20O11 460.3876 461 270; 242; 153 242 Dracocephalum [12]; Dracocephalum moldavica [22]
29 Flavone 6,4′-Dimethoxyisoflavone-7-O-glucoside * C23H24O10 460.4307 461 285 270; 242; 153 242 Astragali radix [36]
30 Flavone Diosmetin-7-O-beta-glucoside C22H22O11 462.4035 463 287 168 123 Dracocephalum [12]; Dracocephalum moldavica [22]; Oxalis corniculata [54]
31 Flavone Apigenin-O-rhamnoside * C22H22O11 462.4035 463 273; 153 153; 171 171 Passion fruit [55]
32 Flavone Chrysoeriol-7-O-glucuronide * C22H20O12 476.3870 477 301 286 258 Propolis [15]
33 Flavone Acacetin 7-beta-O-(6”-acetyl)-glucoside C24H24O11 488.4408 489 472; 354; 296; 223 Dracocephalum moldavica [22]
34 Isoflavone Apigenin 7-O-beta-D-(6”-O-malonyl)-glucoside C24H22O13 518.4237 519 184; 500; 466; 371; 258 125 Dracocephalum [12]; Dracocephalum moldavica [22]; Zostera marina [56]
35 Flavone Acacetin 7-O-beta-D-(6”-O-malonylated)-glucoside C25H24O13 532.4503 533 371; 285; 191; 165 353; 285; 191; 165 147 Dracocephalum moldavica [22]
36 Flavone Diosmetin-7-O-beta-D-(6”-malonyl)-glucoside C25H24O14 548.4497 549 387; 285 370; 272; 147 328; 250; 208; 147 Dracocephalum moldavica [22]
37 Flavone Chrysoeriol O-hexoside C-hexoside * C28H32O16 624.5441 625 445; 463; 377; 347 357; 217 Triticum aestivum L. [57,58]
38 Flavone Isovitexin 2”-O-glucoside-7-O-glucoside [Apigenin 6-C-glucoside 2”-O-glucoside-7-O-glucoside] * C33H40O20 756.6587 757 595; 569; 464; 347; 273 577; 503; 431; 335; 242; 182 Passiflora incarnata [53]
39 Flavonol Kaempferol [3,5,7-Trihydroxy-2-(4-hydro- xyphenyl)-4H-chromen-4-one] C15H10O6 286.2363 287 269; 202 233; 205 216 Dracocephalum [12]; Rapeseed petals [18]; Lonicera japonicum [31]; Rhus coriaria (Sumac) [34]; Andean blueberry [39]
40 Flavonol Quercetin C15H10O7 302.2357 303 285; 228; 165 229; 165 141 Propolis [15]; Actinidia valvata [16]; Rhus coriaria [34]; Potato leaves [59]
41 Flavonol Herbacetin [3,5,7,8-Tetrahydroxy-2-(4-hydro- xyphenyl)-4H-chromen-4-one] * C15H10O7 302.2357 303 203; 275 221 Ocimum [42]; Rhodiola rosea [60,61]
42 Flavonol Dihydroquercetin (Taxifolin; Taxifoliol) C15H12O7 304.2516 305 287 286; 186 185 Dracocephalum [12]; Andean blueberry [39]; Eucalyptus [49];
43 Flavonol Isorhamnetin [Isorhamnetol; Quercetin 3′-Methyl ether; 3-Methylquercetin] * C16H12O7 316.2623 317 299; 257; 214; 173 281; 188 Embelia [13]; Rosmarinus officinalis [14]; Propolis [15]; Actinidia valvata [16]; Andean blueberry [39]
44 Flavonoid 3,5—Diacetyltambulin * C22H20O9 428.3888 427 381; 249 249; 161 161; 124 A. cordifolia [25]
45 Flavonol Dihydrokaempferol-3-O-rhamnoside * C21H22O10 434.3934 435 287; 261 259; 205 187 Vitis vinifera [62,63]
46 Flavonol Astragalin [Kaempferol 3-O-glucoside; Kaempferol-3-Beta-Monoglucoside; Astragaline] C21H20O11 448.3769 447 285; 327 241 199 Dracocephalum [12]; Lonicera japonicum [31]; Mexican lupine species [64]
47 Flavonol Quercitrin [Quercetin 3-O- rhamnoside; Quercetrin] * C21H20O11 448.3769 449 302 202; 174; 127 175 Embelia [13]; Propolis [15]; Rhus coriaria [34]; Bryophyllum pinnatum [54]; Euphorbia hirta [65]
48 Flavonol Kaempferol-3-O-glucuronide C21H18O12 462.3604 463 287 268; 169 241; 119 Dracocephalum [12]; A. cordifolia; G. linguiforme [25]; Rhus coriaria [34]; Strawberry [55]
49 Flavonol Taxifolin-3-O-hexoside [Dihydroquercetin-3-O-hexoside] * C21H22O12 466.3922 467 305; 259; 195; 153 259; 195; 153 231; 149 Andean blueberry [39]; millet grains [45]; Euphorbia hirta [65] Actinidia deliciosa [66];
50 Flavonol Kaempferol 3-O-rutinoside C27H30O15 594.5181 595 287; 345; 389; 449 287; 245; 153 171 Dracocephalum [12]; Lonicera japonicum [31]; Rhus coriaria [34];
51 Flavonol Kaempferol-3,7-Di-O-glucoside * C27H30O16 610.5175 611 287; 449 287; 213; 185; 137 185; 157 Tomato [17]; Rapeseed petals [18]; Taraxacum officinale [19]
52 Flavonol Kaempferol dihexoside rhamnoside * C33H40O20 756.6587 757 595; 287 287; 213; 137 185; 168 C. edulis [25]
53 Flavan-3-ol (epi)Afzelechin * C15H14O5 274.2687 275 228; 210; 175; 157; 132 212; 203; 183; 170 194 A. cordifolia; F. glaucescens; F. herrerae [25]; Cassia granidis [67]; Cassia abbreviata [68]
54 Flavan-3-ol Catechin [D-Catechol] * C15H14O6 290.2681 291 207; 123 123 Vaccinium macrocarpon [69]; Vigna inguiculata [70]; Camellia kucha [71]; Actinidia [72]
55 Flavan-3-ol (epi)catechin C15H14O6 290.2681 291 273; 117 255; 145 Dracocephalum [12]; C. edulis [25]; Andean blueberry [39]
56 Flavan-3-ol Gallocatechin [+(-)Gallocatechin] C15H14O7 306.2675 307 289 259 Dracocephalum [12]; G. linguiforme [25]; Licania ridigna [73]; Rhodiola rosea [74]
57 Flavan-3-ol (epi)Afzelechin derivative * C18H16O10 392.3136 393 275; 179 191 Zostera marina [50]
58 Flavan-3-ol Catechin 3-O-gallate * C22H18O10 442.3723 443 273; 205 263; 211; 171; 143 Vitis vinifera [62]; Camellia kucha [71]; Terminalia arjuna [75]
59 Flavan-3-ol Epigallocatechin-3-gallate * C22H18O11 458.3717 459 290; 207 207; 123 F. glaucescens [25]; Vitis vinifera [62]; Camellia kucha [71]
60 Flavanone Naringenin [Naringetol; Naringenine] C15H12O5 272.5228 273 153; 256 125 Dracocephalum palmatum [8]; Dracocephalum [12] Rapeseed petals [18]; Andean blueberry [39]
61 Flavanone Eriodictyol [3′,4′,5,7-tetrahydroxy-flavanone] C15H12O6 288.2522 289 163; 271 145 117 Dracocephalum palmatum [8]; Dracocephalum [12]; Mentha [23]; Andean blueberry [39]
62 Isolavanone Ferreirin C16H14O6 302.2789 303 177; 285 163 135 Mentha [23]
63 Flavanone Prunin [Naringenin-7-O-glucoside] C21H22O10 434.3934 433 271; 151 269; 151 Dracocephalum palmatum [8]; Dracocephalum [12]; Rapeseed petals [18]
64 Flavanone Eriodictyol-7-O-glucoside [Pyracanthoside; Miscanthoside] C21H22O11 450.3928 449 285; 151 243; 151 Dracocephalum [12]; Mentha [23]; Dracocephalum palmatum [7,8]
65 Flavanone Eriodictyol-7-O-glucuronide C21H20O12 464.3763 463 285; 151 285; 243; 151 Thymus vulgaris [76]; Mentha [77]
66 Hydroxybenzoic acid Protocatechuic acid C7H6O4 154.1201 155 127 117 Lonicera japonicum [31]; Rhus coriaria [34]; Eucalyptus Globulus [51]; Vaccinium macrocarpon [69]; Actinidia [72]
67 Hydroxycinnamic acid p-Coumaric acid [4-Hydroxycinnamic acid; P-Hydroxycinnamic acid; 4-Coumarate] C9H8O3 164.1580 165 147 119 Rapeseed petals [18]; F. pottsii [25]; Rhus coriaria [34]; Andean blueberry [39]; Brazilian propolis [78]
68 Hydroxycinnamic acid Caffeic acid C9H8O4 180.1574 181 135 119 Dracocephalum palmatum [8]; Dracocephalum [12]; Eucalyptus [49]
69 Hydroxycinnamic acid 3,4-Dihydroxyhydrocinnamic acid C9H10O4 182.1733 183 137 Eucalyptus Globulus [51]
70 Phenolic acid 2,3,4,5-Tetrahydroxybenzoic acid [2-Hydroxygallussaure; 3,4,5-Trihydroxysalicylic acid] C7H6O6 186.1189 187 144 PubChem
71 Phenolic acid Salvianic acid A [Danshensu] C9H10O5 198.1727 197 179; 135 135 Huolisu Oral Liquid [38]; Mentha [77]; Hedyotis diffusa [79]
72 Phenolic acid 2,3-Dihydroxy-4-Mathoxycinnamic acid C10H10O5 210.1834 211 192; 134 134; 174 A. cordifolia [25]
73 Hydroxybenzoic acid Ellagic acid [Benzoaric acid; Elagostasine; Lagistase; Eleagic acid] C14H6O8 302.1926 301 284 221 112 Dracocephalum [12]; Rhus coriaria [34]; Eucalyptus [49]; Eucalyptus Globulus [51]
74 Phenolic acid Protocatechuic acid-O-hexoside C13H16O9 316.2607 315 153; 123 123 Rhus coriaria [34]; Eucalyptus Globulus [51]; Euphorbia hirta [65]
75 Phenolic acid Salvianolic acid G C18H12O7 340.2837 341 296; 208 278; 208 235; 164 Dracocephalum [12]; Mentha [41]; Salvia miltiorrhiza [80]
76 Phenolic acid Caffeic acid-4-O-beta-D-hexoside [Caffeoyl-O-hexoside] C15H18O9 342.298 341 179; 119 143; 131 Dracocephalum [12]; Cherimoya, papaya [55]; Sasa veitchii [81]
77 Phenolic acid Chlorogenic acid [3-O-Caffeoylquinic acid] C16H18O9 354.3087 355 179; 338; 227 127 Dracocephalum palmatum [8]; Rapeseed petals [18]; Lonicera japonicum [31]; Rhus coriaria [34]; Andean blueberry [39]
78 Phenolic acid Isochlorogenic acid C16H18O9 354.3087 355 323; 269; 165 295; 208; 133 295; 249; 221 Actinidia [72]
79 Phenolic acid Rosmarinic acid C18H16O8 360.3148 359 161 133 Dracocephalum palmatum [8]; Dracocephalum [12]; Mentha [41]; Zostera marina [56]; Salvia miltiorrhiza [80]; Lepechinia [82]
80 3-Prenyl-4-(dihydrocinnamoyloxy)-cinnamic acid C23H24O4 364.4343 365 261; 185 233; 179 179; 151 Brazilian propolis [78]
81 Phenolic acid Caffeic acid derivative C16H18O9Na 377.2985 377 341; 215 179 Dracocephalum [12]; Bougainvillea [52]
82 Phenolic acid 1/3/4/5-p-Coumaroylquinic acid +C2H2O C18H20O9 380.3460 381 321; 275; 233 260; 218; 143 Actinidia [72]
83 Phenolic acid 8,8′-Aryl-Diferulic acid C20H18O8 386.3521 385 193; 285 193; 161 millet grains [45]
84 Phenolic acid Caffeic acid hexoside dimer C31H40O17 684.6391 683 341 179; 161 143 Strawberry, Lemon, Cherimoya, Passion fruit [55]
85 Phenolic acid Didehydrosalvianolic acid B C36H28O16 716.5979 717 574 319; 263; 187 299; 177 Mentha [77]
86 Phenolic acid Salvianolic acid B [Danfensuan B] C36H30O16 718.6138 717 519; 321 321; 279 279; 185 Huolisu Oral Liquid [38]; Bougainvillea [52]; Mentha [77]; Salvia miltiorrhiza [80]
87 Phenylpropanoic acid Sagerinic acid C36H32O16 720.6297 719 359 161; 197 133 Dracocephalum palmatum [8]; Rosmarinus officinalis [14]; Perilla frutescens [20]; Huolisu Oral Liquid [38]; Mentha [41]
88 Phenolic acid Clerodendranoic acid H C36H32O16 720.6297 719 359 161 Lepechinia [82];
89 Lignan Phillygenin [Sylvatesmin; Phyllygenol; Forsythigenol] C21H24O6 372.4117 371 163; 325 119 Lignans [83]
90 Lignan Medioresinol C21H24O7 388.4111 387 207; 163; 119 163 Rosmarinus officinalis [14]; Lignans [83]; Punica granatum [84]
91 Neolignan Urolignoside + H2O C25H34O11 510.5309 511 493; 451; 421; 349; 285 349; 254; 147 331; 289; 259 Jasminum urophyllum [26]; Actinidia [72]
92 Dihydrochalcone Phloretin [Dihydronaringenin; Phloretol] C15H14O5 274.2687 275 255; 229; 131 237; 209; 164 G. linguiforme [25]; Rosa rugosa [44]; Punica granatum [84]
93 Hydroxycoumarin Umbelliferone [Skimmetin; Hydragin] C9H6O3 162.1421 163 145; 135; 117 117 Sanguisorba officinalis [24]; F. glaucescens [25]; Zostera marina [50]; Actinidia [72]
94 Coumarin Fraxetin [7,8-Dihydroxy-6-methoxycoumarin] C10H8O5 208.1675 209 191; 149 149 147 Embelia [13]; Jatropha [46]; Actinidia [72];
95 Hydroxycoumarin Umbelliferone hexoside C15H16O8 324.2827 325 307; 288; 271; 253; 241 127; 118 G. linguiforme [25]
96 Coumarin glycoside Fraxin (Fraxetin-8-O-glucoside) C16H18O10 370.3081 371 209 Rosa rugosa [44]; Actinidia [72]
97 Anthocyanidin Petunidin C16H13O7+ 317.2702 318 166; 300 121 Dracocephalum [12]; A. cordifolia; C. edulis [21]
98 Anthocyanidin Pelargonidin-3-O-glucoside (callistephin) C21H21O10 433.3854 433 271 153; 225 171 Dracocephalum [12]; Triticum aestivum [85]; Rubus ulmifolius [86]
99 Anthocyanidin Cyanidin-3-O-glucoside [Cyanidin 3-O-beta-D-Glucoside; Kuromarin] C21H21O11+ 449.3848 449 287 153 Dracocephalum [12]; Triticum aestivum [85]; Malpighia emarginata [87]
100 Anthocyanidin Cyanidin 3,5-O-diglucoside C27H31O16 611.5335 611 287; 449 287; 241; 213; 175; 149 213; 185; 172; 157; 145 Rapeseed petals [18]; Muscadine pomace [88]; Berberis microphylla [89]
101 Anthocyanidin Peonidin-3,5-diglucoside [Peonin; Peonidin 3-Glucoside-5-Glucoside] C28H33O16 625.5520 625 463; 374; 301 445; 373 Triticum aestivum [85]; Muscadine pomace [88]
102 Anthocyanidin Cyanidin-3-O-rutinoside-5-O-glucoside C33H41O20 757.6666 757 287; 449; 595 287; 213; 137 185 Camellia kucha [71]; Solanium nigrum [9]
103 Anthocyanidin Delphinidin 3-O-rutinoside-5-O-glucoside C33H41O21 773.5769 773 303; 465; 611 257; 303; 229; 165 257; 229; 201; 116 Berberis microphylla [89]; Solanium nigrum [90]; Iris dichotoma [91]
104 Anthocyanidin Malonyl-shisonin C39H39O21+ 843.7144 843 595; 535; 491; 287 287; 259; 213; 147 213; 185 Perilla frutescens [20,21]
OTHERS
105 Benzenediol Catechol derivative C6H6O3 126.1100 127 124; 118 Embelia [13];
106 Alkyl cinnamate Methyl cinnamate [Methyl 3-Phenylacrilate] C10H10O2 162.1852 164 144 Strawberry [92]
107 Amino acid Phenylalanine [L-Phenylalanine] C9H11NO2 165.1891 166 147; 120 Rapeseed petals [18]; Lonicera japonica [31]; Passiflora incarnata [53]; Potato leaves [59]
108 Amino acid Tyrosine [(2S)-2-Amino-3-(4-Hydroxyphnyl)Propanoic acid] C9H11NO3 181.1885 182 165; 150 113 Euphorbia hirta [65]; Vigna unguiculata [93]; Hylocereus polyrhizus [94]
109 Monobasic carboxylic acid Hydroxyphenyllactic acid C9H10O4 182.1733 181 163; 135 119 Mentha [95]
110 Amino acid L-Tryptophan [Tryptophan; (S)-Tryptophan] C11H12N2O2 204.2252 205 188 144 118 Dracocephalum [12]; Rapeseed petals [18]; Huolisu Oral Liquid [38]; Rosa acicularis [44]
111 Aminoalkylindole 5-Methoxydimethyltryptamine C13H18N2O 218.2948 219 201 159; 118 Dracocephalum [12]; Camellia kucha [71]
112 Omega-5 fatty acid Myristoleic acid [Cis-9-Tetradecanoic acid] C14H26O2 226.3550 227 209 139 Dracocephalum [12]; F. glaucescens [25]
113 Germacranolide Costunolide C15H20O2 232.3181 233 187; 215 145 143 Rosa davurica [44]; Weichang’an Pill [96]
114 Medium-chain fatty acid Hydroxy myristic acid [2S-Hydroxytetradecanoic acid; Alpha-Hydroxy Myristic acid] C14H28O3 244.3703 246 228; 159 199; 172 144 F. pottsii [25]
115 Xanthone Mangiferitin [Norathyriol; 1,3,6,7-Tetrahydroxyxanthone] C13H8O6 260.1990 261 193; 135 179; 124 111 Rhus coriaria [34]
116 Aporphine alkaloid Anonaine C17H15NO2 265.3065 266 248; 171; 122 229; 182; 116 212; 182 Rosa rugosa [44]; Magnolia [97]
117 Ribonucleoside composite of adenine (purine) Adenosine C10H13N5O4 267.2413 268 136; 258 Dracocephalum [12]; Lonicera japonica [31]
118 Omega 3-fatty acid Stearidonic acid [6,9,12,15-Octadecatetraenoic acid; Moroctic acid] C18H28O2 276.4137 277 177; 247 175 G. linguiforme [25]; Rhus coriaria [34]; Jatropha [46]; Salvia Miltiorrhiza [80]
119 Omega 3-fatty acid Linolenic acid (Alpha-Linolenic acid; Linolenate) C18H30O2 278.4296 279 219; 259 159 Jatropha [46]; Salvia Miltiorrhiza [80]; Pinus sylvestris [98]
120 Fatty amide Linoleic acid amide C18H33NO 279.4607 280 262; 244 244; 234; 216; 196; 172 196; 168; 151 Propolis [15]; Rhus coriaria [34]
121 Fatty amide Oleamide C18H35NO 281.4766 282 263; 246; 192 245; 228; 217; 197; 170 Propolis [15]
122 Alkaloid Mesembrenol C17H23NO3 289.3694 290 242; 122 184; 149 Dracocephalum [12]; Sceletium [29]
123 Diterpenoid naphthoquinone Tanshinone IIA [Tanshinone II; Tanshinone B] C19H18O3 294.3444 295 277; 259; 193; 149 259; 241; 199; 149 241; 147 Huolisu Oral Liquid [38]
124 Unsaturated hydroxy fatty acid Hydroxyoctadecatrienoic acid C18H30O3 294.4290 293 275; 235; 185; 172 231; 205; 177 231; 163 Jatropha [46]
125 Polyunsaturated fatty acid Alpha-Kamlolenic Acid [18-Hydroxy-9Z,11E,13E- Octadecatrienoic Acid] C18H30O3 294.4290 293 275; 231; 171 231; 177 231 G. linguiforme; F. glaucescens; F. pottsii [25]
126 Essential fatty acid Hydroxyoctadecadienoic acid C18H32O3 296.4449 295 277; 251; 195; 171; 152 233; 179; 155 A. cordifolia; F. glaucescens; F. herrerae [25]; Jatropha [46]
127 Pterocarpan 3-Hydroxy-9,10-dimethoxypterocarpan C17H16O5 300.3059 301 286; 257; 229; 177; 153 163; 149 145 Astragali radix [36]; Huolisu Oral Liquid [38]
128 Diterpenoid Tanshinone IIB [(S)-6-(Hydroxymethyl)-1,6-Dimethyl-6,7,8,9-Tetrahydrophenanthro [1,2-B]Furan-10,11-Dione] C19H18O4 310.3438 311 283; 137 119 Huolisu Oral Liquid [38]; Salvia Miltiorrhiza [80]
129 p-hydroxyphenacyl-β-D-glucopyranoside C14H18O8 314.2879 313 161; 213 133; 161 133 Rhodiola crenulata [99]
130 Long-chain fatty acid Hydroxy eicosenoic acid C20H38O3 326.5139 327 295; 268; 181; 125 268 237; 135 A. cordifolia; F. pottsii [25]
131 Fructose-phenylalanine C15H21NO7 327.3297 328 310; 292 292; 264; 244; 216; 198; 178 244; 216; 198; 171; 156 Potato leaves [59]
132 Oxylipins 9,10-Dihydroxy-8-oxooctadec-12-enoic acid [oxo-DHODE; oxo-Dihydroxy-octadecenoic acid] C18H32O5 328.4437 327 229 209 183 Dracocephalum [12]; Phyllostachys nigra [81]; Bituminaria [100]
133 Oxylipins 13- Trihydroxy-Octadecenoic acid [THODE] C18H34O5 330.4596 329 229; 293; 211; 171 211; 229; 155 183; 211 Dracocephalum [12]; Sasa veitchii [81]; Bituminaria [100]
134 Unsaturated essential fatty acid Dihydroxy eicosatrienoic acid C20H34O4 338.4816 339 321; 177; 145 145 117 G. linguiforme; A. cordifolia; C. edulis [25]
135 Diterpenoid Komarovinone A C21H28O4 344.4446 345 312; 240 284; 121 268; 135 Dracocephalum komarovi [27]
136 Triterpene Dracocephalone A C20H26O5 346.4174 347 319; 287; 219 219 191 Dracocephalum komarovi [27]
137 Unsaturated omega-3 fatty acid Trihydroxy eicosatetraenoic acid C20H32O5 352.4651 353 261; 293; 243; 207 243; 201; 159; 132 162 F. glaucescens [25]
138 Tetracyclic diterpenoid Komaroviquinone C21H28O5 360.4440 361 343; 302 310; 269; 218; 161 282 Dracocephalum komarovi [27]
139 Triterpene Squalene (Trans-Squalene; Spinacene; Supraene) C30H50 410.718 411 393; 36; 291; 244; 198 Olive leaves [33]; squalene [101]
140 Sterol Stigmasterol [Stigmasterin; Beta-Stigmasterol] C29H48O 412.6908 413 395; 301; 237; 189 189 Dracocephalum [12]; A.cordifolia; F. pottsii [25]; Olive leaves [33]; Hedyotis diffusa [79]
141 Anabolic steroid; Androgen; Androgen ester Vebonol C30H44O3 452.6686 453 435; 336; 226 336 209 Dracocephalum [12]; Rhus coriaria [34]; Hylocereus polyrhizus [94]
142 Triterpenic acid Betulonic acid [Betunolic acid; Liquidambaric acid] C30H46O3 454.6844 455 436; 353; 313; 249 393; 336; 319; 282 154 Rhus coriaria [34]; Rosa rugosa [44]
143 Triterpenic acid 1-Hydroxy-3-oxours-12-en-28-oic acid C30H46O4 470.6838 471 453; 425; 407; 389 365; 335; 283; 205 177; 121 Pear [102]
144 Triterpenic acid Pomolic acid C30H48O4 472.6997 473 454; 371; 302; 144 Sanguisorba officinalis [24]; Pear [102]; Malus domestica [103]
145 Triterpenic acid Tormentic acid [Jacarandic acid; Tomentic acid] C30H48O5 488.6991 487 470; 423; 372 403; 377 Sanguisorba officinalis [24]; Actinidia [72]; Pear [102]
146 Monoterpene glycoside Rhodioloside C [(2E,4R)-4-hydroxy-3,7-dimethyl-2,6-octadienyl β-D-glucopyranosyl(1-3)-β-D-glucopyranoside] C22H38O12 494.5299 493 447; 329; 285 309; 285 294; 187 Rhodiola crenulata [99]; Rhodiola rosea [104,105,106]
147 Carotenoid (all-E)-lutein 3′-O-myristate C40H54O 550.8562 551 533; 509; 429; 385; 355 133 Rosa rugosa [30]; Carotenoids [107]
148 Indole sesquiterpene alkaloid Sespendole C33H45NO4 519.7147 520 184; 359 124 Dracocephalum [12]; Rhus coriaria [34]; Hylocereus polyrhizus [94]
149 Carotenoid Cryptoxanthin [Beta-cryptoxanthin] C40H56O 552.872 553 535; 325; 223 517 Dracocephalum [12]; Sarsaparilla [28]; Carotenoids [107,108];
150 Carotenoid Zeaxanthin [All-Trans-Zexanthin; Anchovyxanthin] C40H56O2 568.8714 569 553; 534; 471; 359 534; 486; 326; 262 516; 473; 308; 262 Sarsaparilla [28]; Carotenoids [107]; orange juice [109]
151 Product of chlorophyll breakdown Pheophorbide a C35H34N4O6 606.6677 607 547; 503; 461 461; 433 433 Product of Chlorophylle breakdown [110]
152 Cycloartanol Cyclopassifloic acid glucoside C37H62O12 698.8810 699 537 375; 331; 259; 185 Passiflora incarnata [53]
153 Carotenoid Carotenoid C41H59O10 711.9012 712 695; 605; 543; 474; 456 412; 369; 200; 143 Carotenoids [32]
154 Carotenoid (all-E)-beta-cryptoxanthin laurate [Beta-Cryptoxanthin-Laurate] C52H78O2 735.1745 735 323; 521; 277 295; 163 249; 173; 134 Sarsaparilla [28]; Carotenoids [107]; Carica papaya [111]
155 Product of chlorophyll degradation Pheophytin A C55H74N4O5 871.1999 593; 533 533; 461 461; 433 Product of Chlorophylle breakdown [110]; Physalis peruviana [112]; Capsicum [113]

* Compounds, firstly identified in genus Dracocephalum.

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© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.

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.

Details

Title
Comparison of Wild and Introduced Dracocephalum jacutense P.: Significant Differences of Multicomponent Composition
Author
Razgonova, Mayya P 1   VIAFID ORCID Logo  ; Okhlopkova, Zhanna M 2   VIAFID ORCID Logo  ; Rozhina, Zoya G 2 ; Egorova, Polina S 3 ; Ercisli, Sezai 4   VIAFID ORCID Logo  ; Golokhvast, Kirill S 5   VIAFID ORCID Logo 

1  N.I. Vavilov All-Russian Institute of Plant Genetic Resources, B. Morskaya 42-44, 190000 Saint-Petersburg, Russia; Institute of Life Science and Biomedicine, Far Eastern Federal University, Sukhanova 8, 690950 Vladivostok, Russia 
2  Department of Biology, North-Eastern Federal University, Belinsky Str. 58, 677000 Yakutsk, Russia 
3  Yakutsk Botanical Garden, Institute for Biological Problems of Cryolithozone Siberian Branch of Russian Academy Sciences, Lenina pr. 41, 677000 Yakutsk, Russia 
4  Department of Horticulture, Faculty of Agriculture, Ataturk University, 25240 Erzurum, Turkey 
5  Department of Biology, North-Eastern Federal University, Belinsky Str. 58, 677000 Yakutsk, Russia; Laboratory of Supercritical Fluid Research and Application in Agrobiotechnology, Tomsk State University, Lenin Str. 36, 634050 Tomsk, Russia; Siberian Federal Scientific Centre of Agrobiotechnology, Centralnaya, Presidium, 633501 Krasnoobsk, Russia 
First page
1211
Publication year
2022
Publication date
2022
Publisher
MDPI AG
e-ISSN
23117524
Source type
Scholarly Journal
Language of publication
English
DOI
https://doi.org/10.3390/horticulturae8121211
ProQuest document ID
2756706600
Copyright
© 2022 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.