Chemical fact sheet: Luteolin 7-O-glucoside

Luteolin 7-O-glucoside

Basics

Category
Flavone and flavonol derivatives
IUPAC-name
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-(((2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
Formula
No formula stored
Exact mass
448.10056 g/mol
Molecular weight
448.38000 g/mol
Structure
Chemical structure of luteolin 7-O-glucoside
Figure 1.1: Chemical structure of luteolin 7-O-glucoside

Sources

In summary, the chemical luteolin 7-O-glucoside has been analyzed from following sources:

Allium flavum subsp. flavum  L.
1st 2nd 3rd 4th
Daphne gnidium  L.
1st
Reseda luteola  L.
1st 2nd
Tanacetum balsamita  L.
1st
Tanacetum parthenium  (L.) Sch. Bip.
1st 2nd 3rd
Tanacetum vulgare  L.
1st

Note that an analysis result in the database may indicate either presence or lack thereof of a chemical in an analyzed sample.

References

  1. K. Bączek, O. Kosakowska, J. Przybył, E. Pióro-Jabrucka, R. Costa, L. Mondello, M. Gniewosz, A. Synowiec, and Z. Węglarz, "Antibacterial and antioxidant activity of essential oils and extracts from costmary (Tanacetum balsamita L.) and tansy (Tanacetum vulgare L.).," Industrial Crops and Products , vol. 102 , pp. 154–163 , DOI: 10.1016/j.indcrop.2017.03.009 .
  2. R. Marques, M. Sousa, M. Oliveira, and M. Melo, "Characterization of weld (Reseda luteola L.) and spurge flax (Daphne gnidium L.) by high-performance liquid chromatography–diode array detection–mass spectrometry in Arraiolos historical textiles.," Journal of Chromatography A , vol. 1216 , pp. 1395–1402 , DOI: 10.1016/j.chroma.2008.12.083 .
  3. C. Moiteiro, H. Gaspar, A. Rodrigues, J. Lopes, and V. Carnide, "HPLC quantification of dye flavonoids in Reseda luteola L. from Portugal.," Journal of Separation Science , vol. 31 , pp. 3683–3687 , DOI: 10.1002/jssc.200800383 .
  4. N. Simin, D. Orcic, D. Cetojevic-Simin, N. Mimica-Dukic, G. Anackov, I. Beara, D. Mitic-Culafic, and B. Bozin, "Phenolic profile, antioxidant, anti-inflammatory and cytotoxic activities of small yellow onion (Allium flavum L. subsp. flavum, Alliaceae)," LWT - Food Science and Technology , vol. 54 , no. 1 , pp. 139–146 , DOI: 10.1016/j.lwt.2013.05.023 .
  5. A. Villela, E. van der Klift, E. Mattheussens, G. Derksen, H. Zuilhof, and T. Beek, "Fast chromatographic separation for the quantitation of the main flavone dyes in Reseda luteola (weld).," Journal of Chromatography A , vol. 1218 , pp. 8544–8550 , DOI: 10.1016/j.chroma.2011.09.069 .
  6. G. Zengin, A. Cvetanonović, U. Gašić, A. Stupar, G. Bulut, I. Şenkardes, A. Dogan, K. Sinan, Z. Aumeeruddy-Elalfi, A. Aktumsek, and M. Mahomoodally, "Modern and traditional extraction techniques affect chemical composition and bioactivity of Tanacetum parthenium (L.) Sch. Bip.," Industrial Crops and Products , vol. 146 , pp. 112202 , DOI: 10.1016/j.indcrop.2020.112202 .

Analysis results

Analysis result 1

STD
True
TLC
False
UV/Vis detector description
HPLC-PDA
Mass spectrometer description
Organism
Tanacetum balsamita  L.
cultivated
dried, powdered
Sample note
Plant raw materials, herbs of T. balsamita, at full flowering state; were obtained from the Botanical Garden of Medicinal and Aromatic Plants (Koryciny, Poland). Voucher specimen were deposited at herbarium of Warsaw Universit of Life Sciences, WULS-SGGW, Poland.
Drying methods
air-dried, dark
Drying temperature
35 °C
Extraction solvents
ethanol:water, 40:60, v/v
Extraction mass/volume-ratio
100 mg/mL
Extraction repeats
10
Extraction time
5 h 10 min
Extract liquid storage temperature
-80 °C
Extract drying method
concentration under vacuum
Dried extract storage temperature
4 °C
Analysis solvents
MeOH
References

K. Bączek, O. Kosakowska, J. Przybył, E. Pióro-Jabrucka, R. Costa, L. Mondello, M. Gniewosz, A. Synowiec, and Z. Węglarz, "Antibacterial and antioxidant activity of essential oils and extracts from costmary (Tanacetum balsamita L.) and tansy (Tanacetum vulgare L.).," Industrial Crops and Products , vol. 102 , pp. 154–163 , DOI: 10.1016/j.indcrop.2017.03.009 .

Analysis result 2

STD
True
TLC
False
UV/Vis detector description
HPLC-PDA
Mass spectrometer description
Organism
Tanacetum vulgare  L.
cultivated
dried, powdered
Sample note
Plant raw materials, herbs of T. vulgare, at full flowering state; were obtained from the Botanical Garden of Medicinal and Aromatic Plants (Koryciny, Poland). Voucher specimen were deposited at herbarium of Warsaw Universit of Life Sciences, WULS-SGGW, Poland.
Drying methods
air-dried, dark
Drying temperature
35 °C
Extraction solvents
ethanol:water, 40:60, v/v
Extraction mass/volume-ratio
100 mg/mL
Extraction repeats
10
Extraction time
5 h 10 min
Extract liquid storage temperature
-80 °C
Extract drying method
concentration under vacuum
Dried extract storage temperature
4 °C
Analysis solvents
MeOH
References

K. Bączek, O. Kosakowska, J. Przybył, E. Pióro-Jabrucka, R. Costa, L. Mondello, M. Gniewosz, A. Synowiec, and Z. Węglarz, "Antibacterial and antioxidant activity of essential oils and extracts from costmary (Tanacetum balsamita L.) and tansy (Tanacetum vulgare L.).," Industrial Crops and Products , vol. 102 , pp. 154–163 , DOI: 10.1016/j.indcrop.2017.03.009 .

Analysis result 3

Detection technique Values Units
UV/Vis 255
348 		nm
[M⁻ H]⁻ 447 m/z
MS²⁻ 285 m/z
STD
False
TLC
False
UV/Vis detector description
LC-diode array (DAD), PDA
Mass spectrometer description
ESI-MS, ion trap
Organism
Daphne gnidium  L.
wild
Collection dates
2007-5, 2007-6
Sample note
The samples were identified and collected by the researchers.
Extraction solvents
water
Extraction time
1 h
Extraction temperature
100 °C
Analysis solvents
water: MeOH, 8:2
References

R. Marques, M. Sousa, M. Oliveira, and M. Melo, "Characterization of weld (Reseda luteola L.) and spurge flax (Daphne gnidium L.) by high-performance liquid chromatography–diode array detection–mass spectrometry in Arraiolos historical textiles.," Journal of Chromatography A , vol. 1216 , pp. 1395–1402 , DOI: 10.1016/j.chroma.2008.12.083 .

Analysis result 4

STD
True
TLC
False
UV/Vis detector description
HPLC-UV/DAD
Mass spectrometer description
ESI-MS, 3-D IT
Organism
Reseda luteola  L.
wild
dried, powdered
Collection dates
2005-5, 2005-6
Sample note
The reseachers identified and collected the samples.
Drying methods
air-dried
Drying temperature
20±5 °C
Dried material storage temperature
-15 °C
Dried material storage notes
dark; as ground
Extraction solvents
methanol:water, 8 : 2
Extraction mass/volume-ratio
33.3 mg/mL
Extraction repeats
1
Extraction time
15 min
Extraction temperature
20±5 °C
Analysis solvents
MeOH:water, 8:2
References

C. Moiteiro, H. Gaspar, A. Rodrigues, J. Lopes, and V. Carnide, "HPLC quantification of dye flavonoids in Reseda luteola L. from Portugal.," Journal of Separation Science , vol. 31 , pp. 3683–3687 , DOI: 10.1002/jssc.200800383 .

Analysis result 5

Detection technique Values Units
[M⁻ H]⁻ 447 m/z
MS²⁻ 285 m/z
STD
True
TLC
False
UV/Vis detector description
Mass spectrometer description
LC-ESI-MS/MS, triple-quadrupole mass spectrometer
Organism
Allium flavum subsp. flavum  L.
wild
ground, dried
Sample note
The whole plants (aerial parts, bulbs) of wild-growing A. flavum subsp. flavum were collected in Serbia. The voucher specimens were prepared, identified and deposited at the Herbarium of the Department of Biology and Ecology (BUNS Herbarium), University of Novi Sad, Faculty of Sciences. The code of the specimens from Dimitrograd was no. 2-1765. The aerial parts were analysed in this group.
Drying methods
air-dried
Extraction solvents
70 % aqueous methanol
Extraction mass/volume-ratio
125 mg/mL
Extraction repeats
1
Extraction time
3 d
Extraction temperature
30 °C
Extract drying method
rotary evaporation under vacuum
Extract drying temperature
45 °C
Analysis solvents
70 % aqueous MeOH; 0.5 % formic acid : MeOH (7 : 3)
Detection note
The precursor and product ions (m/z), respectively, are presented from the standard of this compound in the quantitative MS/MS-analysis.
References

N. Simin, D. Orcic, D. Cetojevic-Simin, N. Mimica-Dukic, G. Anackov, I. Beara, D. Mitic-Culafic, and B. Bozin, "Phenolic profile, antioxidant, anti-inflammatory and cytotoxic activities of small yellow onion (Allium flavum L. subsp. flavum, Alliaceae)," LWT - Food Science and Technology , vol. 54 , no. 1 , pp. 139–146 , DOI: 10.1016/j.lwt.2013.05.023 .

Analysis result 6

Detection technique Values Units
[M⁻ H]⁻ 447 : ND m/z
STD
True
TLC
False
UV/Vis detector description
Mass spectrometer description
LC-ESI-MS/MS, triple-quadrupole mass spectrometer
Organism
Allium flavum subsp. flavum  L.
wild
ground, dried
Sample note
The whole plants (aerial parts, bulbs) of wild-growing A. flavum subsp. flavum were collected in Serbia. The voucher specimens were prepared, identified and deposited at the Herbarium of the Department of Biology and Ecology (BUNS Herbarium), University of Novi Sad, Faculty of Sciences. The code of the specimens from Dimitrograd was no. 2-1765. The bulbs were analysed in this group.
Drying methods
air-dried
Extraction solvents
70 % aqueous methanol
Extraction mass/volume-ratio
125 mg/mL
Extraction repeats
1
Extraction time
3 d
Extraction temperature
30 °C
Extract drying method
rotary evaporation under vacuum
Extract drying temperature
45 °C
Analysis solvents
70 % aqueous MeOH; 0.5 % formic acid : MeOH (7 : 3)
Detection note
Luteolin 7-O-glucoside was not detected in the bulbs, contrary to the aerial parts of this onion taxa.
References

N. Simin, D. Orcic, D. Cetojevic-Simin, N. Mimica-Dukic, G. Anackov, I. Beara, D. Mitic-Culafic, and B. Bozin, "Phenolic profile, antioxidant, anti-inflammatory and cytotoxic activities of small yellow onion (Allium flavum L. subsp. flavum, Alliaceae)," LWT - Food Science and Technology , vol. 54 , no. 1 , pp. 139–146 , DOI: 10.1016/j.lwt.2013.05.023 .

Analysis result 7

Detection technique Values Units
[M⁻ H]⁻ 447 m/z
MS²⁻ 285 m/z
STD
True
TLC
False
UV/Vis detector description
Mass spectrometer description
LC-ESI-MS/MS, triple-quadrupole mass spectrometer
Organism
Allium flavum subsp. flavum  L.
wild
ground, dried
Sample note
The whole plants (aerial parts, bulbs) of wild-growing A. flavum subsp. flavum were collected in Serbia. The voucher specimens were prepared, identified and deposited at the Herbarium of the Department of Biology and Ecology (BUNS Herbarium), University of Novi Sad, Faculty of Sciences. The code of the specimens from Babusnica was no. 2-1767. The aerial parts were analysed in this group.
Drying methods
air-dried
Extraction solvents
70 % aqueous methanol
Extraction mass/volume-ratio
125 mg/mL
Extraction repeats
1
Extraction time
3 d
Extraction temperature
30 °C
Extract drying method
rotary evaporation under vacuum
Extract drying temperature
45 °C
Analysis solvents
70 % aqueous MeOH; 0.5 % formic acid : MeOH (7 : 3)
Detection note
The precursor and product ions (m/z), respectively, are presented from the standard of this compound in the quantitative MS/MS-analysis.
References

N. Simin, D. Orcic, D. Cetojevic-Simin, N. Mimica-Dukic, G. Anackov, I. Beara, D. Mitic-Culafic, and B. Bozin, "Phenolic profile, antioxidant, anti-inflammatory and cytotoxic activities of small yellow onion (Allium flavum L. subsp. flavum, Alliaceae)," LWT - Food Science and Technology , vol. 54 , no. 1 , pp. 139–146 , DOI: 10.1016/j.lwt.2013.05.023 .

Analysis result 8

Detection technique Values Units
[M⁻ H]⁻ 447 m/z
MS²⁻ 285 m/z
STD
True
TLC
False
UV/Vis detector description
Mass spectrometer description
LC-ESI-MS/MS, triple-quadrupole mass spectrometer
Organism
Allium flavum subsp. flavum  L.
wild
ground, dried
Sample note
The whole plants (aerial parts, bulbs) of wild-growing A. flavum subsp. flavum were collected in Serbia. The voucher specimens were prepared, identified and deposited at the Herbarium of the Department of Biology and Ecology (BUNS Herbarium), University of Novi Sad, Faculty of Sciences. The code of the specimens from Babusnica was no. 2-1767. The bulbs were analysed in this group.
Drying methods
air-dried
Extraction solvents
70 % aqueous methanol
Extraction mass/volume-ratio
125 mg/mL
Extraction repeats
1
Extraction time
3 d
Extraction temperature
30 °C
Extract drying method
rotary evaporation under vacuum
Extract drying temperature
45 °C
Analysis solvents
70 % aqueous MeOH; 0.5 % formic acid : MeOH (7 : 3)
Detection note
The precursor and product ions (m/z), respectively, are presented from the standard of this compound in the quantitative MS/MS-analysis.
References

N. Simin, D. Orcic, D. Cetojevic-Simin, N. Mimica-Dukic, G. Anackov, I. Beara, D. Mitic-Culafic, and B. Bozin, "Phenolic profile, antioxidant, anti-inflammatory and cytotoxic activities of small yellow onion (Allium flavum L. subsp. flavum, Alliaceae)," LWT - Food Science and Technology , vol. 54 , no. 1 , pp. 139–146 , DOI: 10.1016/j.lwt.2013.05.023 .

Analysis result 9

Detection technique Values Units
UV/Vis 350 nm
STD
True
TLC
False
UV/Vis detector description
LC-diode array (DAD)
Mass spectrometer description
ESI-MS, ion trap
Organism
Reseda luteola  L.
cultivated
ground, dried
Collection dates
2007-8
Sample note
The reseachers identified the sample. The voucher specimen was deposited at Wageningen and identified by W. Olsder s.n. (WAG, barcodes WAG0248296–WAG0248298).
Drying methods
air-dried, dried outdoors daytime, dried indoors nighttime, 10 days
Dried material storage notes
dark; as ground
Extraction solvents
methanol:water, 8:2 (v/v)
Extraction mass/volume-ratio
20 mg/mL
Extraction time
16 h
Extraction temperature
20±5 °C
Analysis solvents
MeOH:water, 8:2 (v/v)
References

A. Villela, E. van der Klift, E. Mattheussens, G. Derksen, H. Zuilhof, and T. Beek, "Fast chromatographic separation for the quantitation of the main flavone dyes in Reseda luteola (weld).," Journal of Chromatography A , vol. 1218 , pp. 8544–8550 , DOI: 10.1016/j.chroma.2011.09.069 .

Analysis result 10

Detection technique Values Units
[M⁻ H]⁻ 447.09106 m/z
MS²⁻ 285
286 		m/z
MS³⁻ 175
199
217
241
257 		m/z
STD
False
TLC
False
UV/Vis detector description
UHPLC
Mass spectrometer description
UHPLC-MS, HRMS, LTQ OrbiTrap, UHPLC–LTQ OrbiTrap MS/MS, HESI, heated ESI
Organism
Tanacetum parthenium  (L.) Sch. Bip.
wild
ground, dried
Sample note
The samples were collected in Turkey (Taskopru, Karacaoglu village). Taxonomic spotting was performed at Marmara University, Istanbul, Turkey, voucher number: MARE-19056./ Microwave-assisted extraction (MAE) was performed at 600W microwave power.
Drying methods
air-dried
Extraction solvents
ethanol
Extraction mass/volume-ratio
50 mg/mL
Extraction repeats
1
Extraction time
30 min
Extract drying method
concentration under vacuum
Extract drying temperature
40 °C
Dried extract storage temperature
4 °C
Detection note
MS2 fragments (% base peak): 286 (10), 285 (100); MS3: 257 (30), 241 (100), 217 (75), 199 (85), 175 (95); MS4: 241 (5), 226 (15), 213 (30), 197 (100)
References

G. Zengin, A. Cvetanonović, U. Gašić, A. Stupar, G. Bulut, I. Şenkardes, A. Dogan, K. Sinan, Z. Aumeeruddy-Elalfi, A. Aktumsek, and M. Mahomoodally, "Modern and traditional extraction techniques affect chemical composition and bioactivity of Tanacetum parthenium (L.) Sch. Bip.," Industrial Crops and Products , vol. 146 , pp. 112202 , DOI: 10.1016/j.indcrop.2020.112202 .

Analysis result 11

Detection technique Values Units
[M⁻ H]⁻ 447.09106 m/z
MS²⁻ 285
286 		m/z
MS³⁻ 175
199
217
241
257 		m/z
STD
False
TLC
False
UV/Vis detector description
UHPLC
Mass spectrometer description
UHPLC-MS, HRMS, LTQ OrbiTrap, UHPLC–LTQ OrbiTrap MS/MS, HESI, heated ESI
Organism
Tanacetum parthenium  (L.) Sch. Bip.
wild
ground, dried
Sample note
The samples were collected in Turkey (Taskopru, Karacaoglu village). Taxonomic spotting was performed at Marmara University, Istanbul, Turkey, voucher number: MARE-19056./Sonication of plant-ethanol mixture was done in ultrasonic bath for an hour at 30 °C.
Drying methods
air-dried
Extraction solvents
ethanol
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
1
Extraction time
1 h
Extraction temperature
30 °C
Extract drying method
concentration under vacuum
Extract drying temperature
40 °C
Dried extract storage temperature
4 °C
Detection note
MS2 fragments (% base peak): 286 (10), 285 (100); MS3: 257 (30), 241 (100), 217 (75), 199 (85), 175 (95); MS4: 241 (5), 226 (15), 213 (30), 197 (100)
References

G. Zengin, A. Cvetanonović, U. Gašić, A. Stupar, G. Bulut, I. Şenkardes, A. Dogan, K. Sinan, Z. Aumeeruddy-Elalfi, A. Aktumsek, and M. Mahomoodally, "Modern and traditional extraction techniques affect chemical composition and bioactivity of Tanacetum parthenium (L.) Sch. Bip.," Industrial Crops and Products , vol. 146 , pp. 112202 , DOI: 10.1016/j.indcrop.2020.112202 .

Analysis result 12

Detection technique Values Units
[M⁻ H]⁻ 447.09106 m/z
MS²⁻ 285
286 		m/z
MS³⁻ 175
199
217
241
257 		m/z
STD
False
TLC
False
UV/Vis detector description
UHPLC
Mass spectrometer description
UHPLC-MS, HRMS, LTQ OrbiTrap, UHPLC–LTQ OrbiTrap MS/MS, HESI, heated ESI
Organism
Tanacetum parthenium  (L.) Sch. Bip.
wild
ground, dried
Sample note
The samples were collected in Turkey (Taskopru, Karacaoglu village). Taxonomic spotting was performed at Marmara University, Istanbul, Turkey, voucher number: MARE-19056./The plant samples were macerated at room temperature at dark for 24 h.
Drying methods
air-dried
Extraction solvents
ethanol
Extraction mass/volume-ratio
50 mg/mL
Extraction repeats
1
Extraction time
1 d
Extraction temperature
20±5 °C
Extract drying method
concentration under vacuum
Extract drying temperature
40 °C
Dried extract storage temperature
4 °C
Detection note
MS2 fragments (% base peak): 286 (10), 285 (100); MS3: 257 (30), 241 (100), 217 (75), 199 (85), 175 (95); MS4: 241 (5), 226 (15), 213 (30), 197 (100)
References

G. Zengin, A. Cvetanonović, U. Gašić, A. Stupar, G. Bulut, I. Şenkardes, A. Dogan, K. Sinan, Z. Aumeeruddy-Elalfi, A. Aktumsek, and M. Mahomoodally, "Modern and traditional extraction techniques affect chemical composition and bioactivity of Tanacetum parthenium (L.) Sch. Bip.," Industrial Crops and Products , vol. 146 , pp. 112202 , DOI: 10.1016/j.indcrop.2020.112202 .