Chemical fact sheet: Luteolin 6-C-glucoside

The BCDB-database is not an authoritative database. This sheet collates data stored for chemical entry luteolin 6-C-glucoside and its related chemical compound entries isoorientin .

Luteolin 6-C-glucoside

Basics

Category
Flavone and flavonol derivatives
IUPAC-name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
Formula
No formula stored
Exact mass
464.09548 g/mol
Molecular weight
448.40000 g/mol
Structure
Chemical structure of luteolin 6-C-glucoside
Figure 1.1: Chemical structure of luteolin 6-C-glucoside

Sources

In summary, the chemical luteolin 6-C-glucoside has been analyzed from following sources:

Achillea millefolium  L.
1st 2nd
Isatis indigotina
1st
Isatis tinctoria French Woad  L.
1st
Isatis tinctoria Thüringer Waid  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. Ø. Andersen, and K. Markham, Flavonoids. Chemistry, biochemistry and applications.. CRC Press, 2006
  2. M. Dias, L. Barros, M. Duenas, E. Pereira, A. Carvalho, M. Oliveira, C. Santos-Buelga, and I. Ferreira, "Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction.," Food Chemistry , vol. 141 , no. 4 , pp. 4152–4160 , DOI: 10.1016/j.foodchem.2013.07.018 .
  3. M. Tobias, I. Plitzko, and M. Hamburger, "A comprehensive metabolite profiling of Isatis tinctoria leaf extracts.," Phytochemistry , vol. 70 , no. 7 , pp. 924-934 , DOI: 10.1016/j.phytochem.2009.04.019 .
  4. T. Nguyen, A. Jamali, E. Grand, K. Morreel, P. Marcelo, E. Gontier, and R. Dauwe, "Phenylpropanoid profiling reveals a class of hydroxycinnamoyl glucaric acid conjugates in Isatis tinctoria leaves," Phytochemistry , vol. 144 , pp. 127–140 , DOI: 10.1016/j.phytochem.2017.09.007 .

Analysis results

Analysis result 1

Detection technique Values Units
UV/Vis 350 nm
[M⁻ H]⁻ 447 m/z
MS²⁻ 285
297
327
357 		m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
HPLC-MS/MS
Organism
Achillea millefolium  L.
wild
dried, powdered
Sample note
The wild yarrrow inflorescences and upper leaves were collected by researchers from 50 plants growing in two different grasslands of about one hectare. The gathered material was mixed and made into a unique sample, dried and powdered (20mesh). A voucher specimen was deposited at the Herbarium fo the Excola Superior Agraria de Braganca (BRESA).
Drying methods
lyophilized
Extraction solvents
methanol
Extraction mass/volume-ratio
16.7 mg/mL
Extraction repeats
2
Extraction time
1 h
Extraction temperature
25 °C
Extract drying method
rotary evaporation
Extract drying temperature
40 °C
Analysis solvents
water
Detection note
The fragment ions were the following, at m/z 357 [M - H - 90]–, at m/z 327 [M - H - 120]– and at m/z 297 [M - H - 30]–.
References

M. Dias, L. Barros, M. Duenas, E. Pereira, A. Carvalho, M. Oliveira, C. Santos-Buelga, and I. Ferreira, "Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction.," Food Chemistry , vol. 141 , no. 4 , pp. 4152–4160 , DOI: 10.1016/j.foodchem.2013.07.018 .

Analysis result 2

Detection technique Values Units
UV/Vis 350 nm
[M⁻ H]⁻ 447 m/z
MS²⁻ 285
297
327
357 		m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD
Mass spectrometer description
HPLC-MS/MS
Organism
Achillea millefolium  L.
wild
dried, powdered
Sample note
The wild yarrrow inflorescences and upper leaves were collected by researchers from 50 plants growing in two different grasslands of about one hectare. The gathered material was mixed and made into a unique sample, dried and powdered (20mesh). A voucher specimen was deposited at the Herbarium fo the Excola Superior Agraria de Braganca (BRESA).
Drying methods
lyophilized
Extraction solvents
water
Extraction mass/volume-ratio
5 mg/mL
Extraction repeats
1
Extraction time
10 min
Extraction temperature
100 °C
Extract drying method
lyophilization, Infusion
Analysis solvents
water
Detection note
The fragment ions were the following, at m/z 357 [M - H - 90]–, at m/z 327 [M - H - 120]– and at m/z 297 [M - H - 30]–.
References

M. Dias, L. Barros, M. Duenas, E. Pereira, A. Carvalho, M. Oliveira, C. Santos-Buelga, and I. Ferreira, "Chemical composition of wild and commercial Achillea millefolium L. and bioactivity of the methanolic extract, infusion and decoction.," Food Chemistry , vol. 141 , no. 4 , pp. 4152–4160 , DOI: 10.1016/j.foodchem.2013.07.018 .

Analysis result 3

Detection technique Values Units
UV/Vis 211
268
348 		nm
[M⁺ H]⁺ 449 m/z
[M⁻ H]⁻ 447 m/z
MS²⁻ 327
357
429 		m/z
STD
False
TLC
False
UV/Vis detector description
HPLC-PDA, photodiode array (PDA)
Mass spectrometer description
HPLC-ESI-MS, ion trap, HPLC-TOF-MS, APCI
Organism
Isatis tinctoria Thüringer Waid  L.
cultivated
ground, dried, cut into small pieces
Collection dates
2003-9
Sample note
The plants were cultivated on the experimental plots of the Agricultural Research Station of Thuringia (TLL), Dornburg, Germany. Specimens of seeds from the strains are kept at the TLL, under accessions number 153/PG 1 (Thüringer Waid).
Drying methods
oven-dried
Drying temperature
40 °C
Dried material storage temperature
15 °C
Dried material storage notes
dark; in the brown glass bottles
Extraction solvents
methanol
Extraction repeats
2
Extraction time
12 min
Extraction temperature
70 °C
Analysis solvents
MeOH
Detection note
[M + Na]+ = 471
References

M. Tobias, I. Plitzko, and M. Hamburger, "A comprehensive metabolite profiling of Isatis tinctoria leaf extracts.," Phytochemistry , vol. 70 , no. 7 , pp. 924-934 , DOI: 10.1016/j.phytochem.2009.04.019 .

Analysis result 4

Detection technique Values Units
UV/Vis 211
268
348 		nm
[M⁺ H]⁺ 449 m/z
[M⁻ H]⁻ 447 m/z
MS²⁻ 327
357
429 		m/z
STD
False
TLC
False
UV/Vis detector description
HPLC-PDA, photodiode array (PDA)
Mass spectrometer description
HPLC-ESI-MS, ion trap, HPLC-TOF-MS, APCI
Organism
Isatis indigotina
cultivated
ground, dried, cut into small pieces
Collection dates
2003-9
Sample note
The plants were cultivated on the experimental plots of the Agricultural Research Station of Thuringia (TLL), Dornburg, Germany. Specimens of seeds from the strains are kept at the TLL, under accessions number 153 PG 12 (I. indigotina).NOTE. There are conflicting views on the taxonomy of I. tinctoria (European woad) and I. indigotica (Chinese woad). I. indigotina was described for the first time by Fortune in 1846, and initially considered as a distinct species. Afterward, some taxonomists have classified it as a variety of I. tinctoria. Nowadays, I. indigotina is considered as a synonym of I. tinctoria [e.g. The Plant List, IPNI (International Plant Name Index), Tropicos]. (Speranzo et al. 2020). In this database, we use the names similarly as the authors.
Drying methods
oven-dried
Drying temperature
40 °C
Dried material storage temperature
15 °C
Dried material storage notes
dark; in the brown glass bottles
Extraction solvents
methanol
Extraction repeats
2
Extraction time
12 min
Extraction temperature
70 °C
Analysis solvents
MeOH
Detection note
[M + Na]+ = 471
References

M. Tobias, I. Plitzko, and M. Hamburger, "A comprehensive metabolite profiling of Isatis tinctoria leaf extracts.," Phytochemistry , vol. 70 , no. 7 , pp. 924-934 , DOI: 10.1016/j.phytochem.2009.04.019 .

Analysis result 5

Detection technique Values Units
[M⁻ H]⁻ 447.09310 m/z
MS²⁻ 327
357
429 		m/z
STD
False
TLC
False
UV/Vis detector description
Mass spectrometer description
ESI, LTQ orbitrap, LTQ linear ion trap
Organism
Isatis tinctoria French Woad  L.
cultivated
fresh, frozen, cut into small pieces, frozen in liquid nitrogen
Sample note
The seeds were provided by the botanical garden of Amiens (Jardin des Plantes), France, where specimens of seeds from the strain were kept under accession number 061003-3. The seeds were sown in soil and grown in a greenhouse at 16h/8h day/night regime, 24 C, 70% moisture. The samples ere taken from 11-week-old plants at the rosette stage.
Extraction solvents
methanol
Extraction repeats
2
Extraction time
10 min
Extraction temperature
70 °C
Extract drying method
evaporation in the speed vacuum
Analysis solvents
water: MeOH
References

T. Nguyen, A. Jamali, E. Grand, K. Morreel, P. Marcelo, E. Gontier, and R. Dauwe, "Phenylpropanoid profiling reveals a class of hydroxycinnamoyl glucaric acid conjugates in Isatis tinctoria leaves," Phytochemistry , vol. 144 , pp. 127–140 , DOI: 10.1016/j.phytochem.2017.09.007 .

Isoorientin

Basics

Category
None
IUPAC-name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
Formula
No formula stored
Exact mass
448.10056 g/mol
Molecular weight
No weights stored
Structure
Chemical structure of isoorientin
Figure 2.1: Chemical structure of isoorientin

Sources

No links to any potential source for this chemical in the database.

References

  1. Ø. Andersen, and K. Markham, Flavonoids. Chemistry, biochemistry and applications.. CRC Press, 2006

Analysis results

No analysis results for this entry in the database.