Flavonoids of Teucrium hircanicum

Oganesyan, G. B.; Mnatsakanyan, V. A.

doi:10.1007/bf00596665

Cited by 6 publications

(7 citation statements)

References 8 publications

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“…The investigation of the essential oil of this species revealed the presence of (E)-βfarnesene, hexahydrofarnesyl acetone, linalool, dihydroedulane, and ar-curcumene, as major compounds [18]. Besides, avonoids pedalitin, and luteolin 7-O-B-D-glucopyranoside, and diterpenes furolactones have been isolated from T. hyrcanicum [19,20].…”

Section: Introductionmentioning

confidence: 99%

Isolation and structure elucidation of the compounds from Teucrium hyrcanicum L. and the investigation of cytotoxicity, antioxidant activity, and protective effect on hydrogen peroxide-induced oxidative stress

Ghasemi

Evazalipour

Peyghanbari

et al. 2023

Preprint

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Background: Teucrium hyrcanicum L. (family Lamiaceae) is widely distributed in the north and northwest of Iran. It has been used in form of tea, tonic, and tincture for the treatment of various diseases such as cough, rheumatism, and fever. Methods: In this study, the total phenolic and flavonoid contents, antioxidant and cytotoxic activities of total extract and different fractions of T. hyrcanicum were measured. Furthermore, the potential ability of T. hyrcanicum to protect H2O2-induced oxidative stress was tested on NIH3T3 cell line. Then, the isolation and structure elucidation of the compounds were performed on the most potent fractions. Finally, the quantification of isolated compounds in total extract (TE) was done by HPLC method. Isolated phytochemicals were assessed for cytotoxic and antioxidant activity. Results: The results indicated that the methanol fraction (MF) had the highest amount of phenolic and flavonoid contents (69.36 mg GAE/g extract and 68.95 mg QE/g extract). The highest radical scavenging activities were observed from MF and TE (IC50 44.32 and 61.12 μg.ml-1, respectively). The best cytotoxicity was obtained by ethyl acetate fraction (EF) against A431 and MCF7 (IC50 values of 235.4and 326.6 μg.ml-1, respectively). The pretreatment with MF exerts the highest reduction in malondialdehyde (MDA) formation (IC50= 2.51 μM, p<0.001) compared to the H2O2 group (5.77 μM). Also, MF significantly inhibited H2O2-induced Glutathione (GSH) oxidation (p<0.001). Furthermore, two phenolic compounds, including acteoside and quercetin were isolated and identified in MF and EF, respectively. The IC50 values of acteoside and quercetin in DPPH assay were 7.19 and 5.56 µg.ml-1, respectively. Both quercetin and acteoside significantly reduced the MDA formation and inhibited GSH oxidation which was comparable with BHA (as standard antioxidant) (p< 0.05). Acteoside demonstrated significant cytotoxicity against all tested cell lines (IC50=32 to 145 μg.ml-1). The HPLC quantification of isolated compounds revealed that the quantity of acteoside and quercetin in TE were 93.31 and 16.87 μg.mg-1, respectively. Conclusions: The isolated compounds (quercetin and acteoside) had significant antioxidant activity and revealed protective effect on H2O2-induced oxidative stress which was comparable with BHA.

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Section: Introductionmentioning

confidence: 99%

Isolation and structure elucidation of the compounds from Teucrium hyrcanicum L. and the investigation of cytotoxicity, antioxidant activity, and protective effect on hydrogen peroxide-induced oxidative stress

Ghasemi

Evazalipour

Peyghanbari

et al. 2023

Preprint

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“…The studies showed that a characteristic feature of D. multicaule is the presence of hydroxylated flavones (apigenin and luteolin) and their glucosides (cosmosiin, apigenin 5-O-β-D-glucopyranoside and cinaroside) [5,6] in addition to mono-(acacetin, genkwanin [5], isokaempferide), di-(cirsimaritin, kumatakenin), tri-(xanthomicrol, penduletin), tetra-(gardenin B, calicopterin), and pentamethoxylated (4′-methylcalicopterin) [4] flavones and flavonols with a 4′-O-substituted B-ring (besides luteolin and its derivatives). Starting with cirsimaritin and further (tri-and more methoxylated flavones and flavonols), flavonoids are 6-oxygenated.…”

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confidence: 99%

“…et Auch. ex Benth.[3] isolated 13 bioactive flavones, flavonols, and flavone glucosides [4][5][6].In continuation of the study of the flavonoid composition of the aerial part of this plant, column chromatography (CC) of the CHCl 3 fraction of the aqueous extract (13 mg) over silica gel L (40/100 mesh) with subsequent preparative TLC on Silufol UV-254 plates (×4) using C 6 H 6 :ether (6:1) isolated calicopterin (5,4′-dihydroxy-3,6,7,8-tetramethoxyflavone, 1, 5.5 mg), which was identified by comparison of the TLC and mixed melting point with an authentic sample, and yellow needle-like crystals (2.6 mg), mp 248-251°C (C 6 H 6 ), molecular ion in the mass spectrum (EI, 70 eV, m/z, Irel, %): 314 (100), of a flavonoid (IR spectrum) with a positive cyanidine Mg/HCl reaction. This indicated the presence of two OH and two OMe groups in its structure.…”

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Minor flavonols from Dracocephalum multicaule

Oganesyan

2009

Chem Nat Compd

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Plants of the genus Dracocephalum L. (Lamiaceae) that contain flavonoids are widely used in folk medicine of various countries as sedative, antibacterial, anti-inflammatory, antitumor, and other agents. Their pharmacological activity has been confirmed experimentally [1,2].A study of the flavonoid composition of the aerial part of the herbaceous perennial Dracocephalum multicaule Montbr. et Auch. ex Benth.[3] isolated 13 bioactive flavones, flavonols, and flavone glucosides [4][5][6].In continuation of the study of the flavonoid composition of the aerial part of this plant, column chromatography (CC) of the CHCl 3 fraction of the aqueous extract (13 mg) over silica gel L (40/100 mesh) with subsequent preparative TLC on Silufol UV-254 plates (×4) using C 6 H 6 :ether (6:1) isolated calicopterin (5,4′-dihydroxy-3,6,7,8-tetramethoxyflavone, 1, 5.5 mg), which was identified by comparison of the TLC and mixed melting point with an authentic sample, and yellow needle-like crystals (2.6 mg), mp 248-251°C (C 6 H 6 ), molecular ion in the mass spectrum (EI, 70 eV, m/z, Irel, %): 314 (100), of a flavonoid (IR spectrum) with a positive cyanidine Mg/HCl reaction. This indicated the presence of two OH and two OMe groups in its structure.UV spectra with diagnostic additives according to the literature method [7] [MeOH, λ max (relative intensities, nm): 257 sh (0.30), 268 (1.00), 290 sh (0.70), 321 sh (0.53), 348 (0.62)] showed that the sample might have been a mixture of two structurally similar phloroglucinol compounds according to the first (348 nm) and second (268 nm) bands and the ratio of intensities in the initial MeOH solution and with added AlCl 3 and AlCl 3 + HCl in addition to NaOMe (formation of a third band at 331 nm and a bathochromic shift of the first to 394 nm with increased intensity) and NaOAc (272, 329, 398 sh nm). These were isokaempferide (5,7,4′-trihydroxy-3-methoxyflavone, 2) and kumatakenin (5,4′-dihydroxy-3,7-dimethoxyflavone, 3), which contains 3-OMe, 5-OH, 7-OMe (in addition to 7-OH), and 4′-OH groups [8][9][10].The mass spectrum of the sample showed ions with m/z 314 (100) [M] 3-methoxyflavone fragmentation [11-14]. However, there was no molecular ion for 2 with m/z 300 and ions with m/z 272 (8) [M -CO] + , 271 (30) [M -COH] + (also in the mass spectrum of 3 [12, 13]), 269 (3), 257 (4) [M -CH 3 CO] + , 153 (2) [A 1 + H] + , 152 (3) [A 1 ] + (B 1 and B 2 ions like for 3) may have belonged to 2 but were weak. This might have been due to the conditions under which the spectra were recorded. The small amount of sample did not enable its NMR spectrum to be obtained.PMR spectra of the acetates of isokaempferide (4) and kumatakenin (5), minor side products obtained from CC (conditions given above) of total acetates (Ac 2 O/Py) of mixtures of the apigenin (5,7,4′-trihydroxyflavone, 6) and isokaempferide in addition to cirsimaritin (5,4′-dihydroxy-6,7-dimethoxyflavone, 7) and kumatakenin, respectively, provided additional confirmation that isokaempferide (2) and kumatakenin (3) were native flavonols of D. mu...

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“…In the Flora Iranica, this genus is represented by 12 species [1]. Various species of the genus Teucrium are used as antiseptic, antipyretic, antiinflammatory, antispasmodic, antinociceptive, anti-rheumatic, anthelmintic, diuretic, hypoglycemic, diaphoretic, and tonic in folk medicine [2].Phytochemically, several diterpenoids, diterpenelactones, triterpenoids, flavonoids, and minor phenolic compounds have already been isolated from this plant and analyzed [3][4][5][6][7].A literature survey on the essential oil composition of some Teucrium species revealed that in T. melissoides, T. polium subsp. capitatum, T. haenseleri, and T. capitatum, monoterpenes such as α-pinene, β-pinene, p-cymene, and limonene were the main constituents.…”

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“…Phytochemically, several diterpenoids, diterpenelactones, triterpenoids, flavonoids, and minor phenolic compounds have already been isolated from this plant and analyzed [3][4][5][6][7].…”

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Chemical composition of the essential oil of Teucrium hyrcanicum and T. chamaedrys L. SUBSP. chamaedrys from Iran

2008

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The genus Teucrium (Lamiaceae) is comprised of about 340 species widespread over the world. In the Flora Iranica, this genus is represented by 12 species [1]. Various species of the genus Teucrium are used as antiseptic, antipyretic, antiinflammatory, antispasmodic, antinociceptive, anti-rheumatic, anthelmintic, diuretic, hypoglycemic, diaphoretic, and tonic in folk medicine [2].Phytochemically, several diterpenoids, diterpenelactones, triterpenoids, flavonoids, and minor phenolic compounds have already been isolated from this plant and analyzed [3][4][5][6][7].A literature survey on the essential oil composition of some Teucrium species revealed that in T. melissoides, T. polium subsp. capitatum, T. haenseleri, and T. capitatum, monoterpenes such as α-pinene, β-pinene, p-cymene, and limonene were the main constituents. Also in the oils of T. oriental L. var. oriental, T. fruticans, T. abutiloides, T. salviastrum, T. turredanum, and T. betonicum, sesquiterpenoids such as β-caryophyllene, germacrene D, and α-humulene were reported to be the major components [8][9][10][11][12][13][14][15].In this paper the essential oil composition of Teucrium hyrcanicum, which is an endemic plant related to the Caspian sea area, is reported for the first time [16].Thirty-six components were identified in the oil of T. hyrcanicum representing 93.1% of the oil, and also forty-two components were characterized in the oil of T. chamaedrys ssp. chamaedrys representing 94.1% of the oil.The identified components with their percentages are given in Table 1. These components are listed in order of their elution from the DB-5 column.As it is shown, the oil of T. hyrcanicum consists of oxygenated monoterpenes (16.3%), sesquiterpene hydrocarbons (32.3%), and oxygenated sequiterpenes (24.9%). Hexahydrofarnesyl acetone (12.7%), linalool (11.7%) and E-β-farnesene (10.7%), dihydroedulane (8.6%), and ar-curcumene (8.5%) were the main constituents in this oil. As a result, in the oil of T. hyrcanicum, sesquiterpenes (61.7%) predominated over monoterpenes (16.3%).In contrast, the oil of T. chamaedrys ssp. chamaedrys is rich in sesquiterpenes (63.8%), with α-muurolene (15.3%), β-caryophyllene (15.0%), and Z-β-farnesene (7.6%) as the major components. Among the identified monoterpenes (26.5%) in this oil, α-pinene (7.9%), β-pinene (5.9%), and limonene (5.1%) are the most abundant.The composition of the essential oil of T. chamaedrys (subspecies not referred to) has been reported in the literature. Some differences in the quantity and quality of the oil composition may be due to different subspecies, chemotype, and geographic and climatic factors. For example, in two of them, germacrene D and β-pinene were reported as the main constituents [17,18].

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Flavonoids of Teucrium hircanicum

Cited by 6 publications

References 8 publications

Isolation and structure elucidation of the compounds from Teucrium hyrcanicum L. and the investigation of cytotoxicity, antioxidant activity, and protective effect on hydrogen peroxide-induced oxidative stress

Isolation and structure elucidation of the compounds from Teucrium hyrcanicum L. and the investigation of cytotoxicity, antioxidant activity, and protective effect on hydrogen peroxide-induced oxidative stress

Minor flavonols from Dracocephalum multicaule

Chemical composition of the essential oil of Teucrium hyrcanicum and T. chamaedrys L. SUBSP. chamaedrys from Iran

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