Chemical fact sheet: Indoxyl β-D-glucoside

Indoxyl β-D-glucoside

Basics

Category
Indolics & indole alkaloid derivatives
IUPAC-name
(2S,3R,4S,5S,6R)-2-((1H-indol-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
Formula
No formula stored
Exact mass
295.10560 g/mol
Molecular weight
No weights stored
Structure
Chemical structure of indoxyl β-D-glucoside
Figure 1.1: Chemical structure of indoxyl β-D-glucoside

Sources

In summary, the chemical indoxyl β-D-glucoside has been analyzed from following sources:

Isatis indigotina
1st
Isatis tinctoria 'IT BM'  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. T. Maugard, E. Enaud, P. Choisy, and M. Legoy, "Identification of an indigo precursor from leaves of Isatis tinctoria (woad).," Phytochemistry , vol. 58 , no. 6 , pp. 897–904 , DOI: 10.1016/S0031-9422(01)00335-1 .
  2. 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 results

Analysis result 1

Detection technique Values Units
UV/Vis 218
280 		nm
[M⁺ H]⁺ 296 m/z
STD
True
TLC
False
UV/Vis detector description
HPLC-DAD, UV
Mass spectrometer description
HPLC-MS
Organism
Isatis tinctoria 'IT BM'  L.
cultivated
fresh
Collection dates
2000-6
Sample note
The cultivar IT BM was grown in a field of CRITT (St Savin, France) and was collected by the researchers.
Extraction solvents
acetone:acetic acid 1% (v/v)
Extraction mass/volume-ratio
100 mg/mL
Extraction time
4 h
Extraction temperature
24 °C
Extract drying method
evaporation under reduced pressure
Analysis solvents
acetic acid (was left in the extract); MeOH
Detection note
In young leaves
References

T. Maugard, E. Enaud, P. Choisy, and M. Legoy, "Identification of an indigo precursor from leaves of Isatis tinctoria (woad).," Phytochemistry , vol. 58 , no. 6 , pp. 897–904 , DOI: 10.1016/S0031-9422(01)00335-1 .

Analysis result 2

Detection technique Values Units
UV/Vis 222
280 		nm
[M⁻ H]⁻ 294 m/z
MS²⁻ 131
276 		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
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 3

Detection technique Values Units
UV/Vis 222
280 		nm
[M⁻ H]⁻ 294 m/z
MS²⁻ 131
276 		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
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 .