Chemical fact sheet: Chrysophanol

Chrysophanol

Basics

Category
Anthraquinone and quinone derivatives
IUPAC-name
1,8-Dihydroxy-3-methylanthracene-9,10-dione
Formula
No formula stored
Exact mass
254.05790 g/mol
Molecular weight
254.24000 g/mol
Structure
Chemical structure of chrysophanol
Figure 1.1: Chemical structure of chrysophanol

Sources

In summary, the chemical chrysophanol has been analyzed from following sources:

Rhamnus saxatilis  Jacq.
1st
Rheum emodii
1st
Rheum officinale  Baill.
1st
Rheum palmatum  L.
1st
Rheum tanguticum  Maxim. ex Balf
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. L. Gao, T. Guo, X. Xu, and J. Yang, "Rapid identification and simultaneous analysis of multiple constituents from Rheum tanguticum Maxim. ex Balf. By UPLC/Q-TOF-MS.," Natural Product Research , vol. 31 , no. 13 , pp. 1529–1535 , DOI: 10.1080/14786419.2017.1280491 .
  2. J. Liu, L. Leng, Y. Liu, H. Gao, W. Yang, S. Chen, and A. Liu, "Identification and quantification of target metabolites combined with transcriptome of two rheum species focused on anthraquinone and flavonoids biosynthesis.," Scientific Reports , vol. 10 , no. 1 , pp. 20241 , DOI: 10.1038/s41598-020-77356-9 .
  3. M. Locatelli, F. Tammaro, L. Menghini, G. Carlucci, F. Epifano, and S. Genovese, "Anthraquinone profile and chemical fingerprint of Rhamnus saxatilis L. from Italy.," Phytochemistry Letters , vol. 2 , pp. 223–226 , DOI: 10.1016/j.phytol.2009.10.001 .
  4. S. Verma, N. Singh, and A. Sinha, "Determination and locational variations in the quantity of hydroxyanthraquinones and their glycosides in rhizomes of Rheum emodi using high-performance liquid chromatography.," Journal of Chromatography A , vol. 1097 , pp. 59–65 , DOI: 10.1016/j.chroma.2005.08.018 .

Analysis results

Analysis result 1

Detection technique Values Units
UV/Vis 225
260 		nm
[M⁻ H]⁻ 253.05020 m/z
MS²⁻ 197.04270
209.02040
225.05490 		m/z
STD
False
TLC
False
UV/Vis detector description
UPLC-UV/Vis
Mass spectrometer description
UPLC-QTOF-ESI-MS/MS, HDMS
Organism
Rheum tanguticum  Maxim. ex Balf
wild
dried, powdered
Collection dates
2007-10
Sample note
The root samples were identified by Prof. Zhichuan Bai at the College of Horticulture and Landscape, Southwest University. Voucher specimens (No. 200712) were deposited at the Institute of Medicinal Plant Development, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, China.
Extraction solvents
methanol
Extraction mass/volume-ratio
40 mg/mL
Extraction repeats
3
Extraction time
1 h 30 min
Extraction temperature
20±5 °C
Analysis solvents
methanol
References

L. Gao, T. Guo, X. Xu, and J. Yang, "Rapid identification and simultaneous analysis of multiple constituents from Rheum tanguticum Maxim. ex Balf. By UPLC/Q-TOF-MS.," Natural Product Research , vol. 31 , no. 13 , pp. 1529–1535 , DOI: 10.1080/14786419.2017.1280491 .

Analysis result 2

Detection technique Values Units
[M⁻ H]⁻ 253.20000 m/z
MS²⁻ 225.10000 m/z
STD
True
TLC
False
UV/Vis detector description
UV/Vis
Mass spectrometer description
UPLC-ESI-Q-TOF-MS/MS
Organism
Rheum officinale  Baill.
cultivated
fresh, powdered
Sample note
The identification of Rheum officinale from the collected rhizome specimens were conducted by Prof. Li Xiang at the Institute of Chinese Materia Medica, China Academy of Chinese Medical Science, Beijing, China.
Dried material storage temperature
-80 °C
Extraction solvents
methanol
Extraction repeats
1
Extraction temperature
4 °C
Analysis solvents
methanol
References

J. Liu, L. Leng, Y. Liu, H. Gao, W. Yang, S. Chen, and A. Liu, "Identification and quantification of target metabolites combined with transcriptome of two rheum species focused on anthraquinone and flavonoids biosynthesis.," Scientific Reports , vol. 10 , no. 1 , pp. 20241 , DOI: 10.1038/s41598-020-77356-9 .

Analysis result 3

Detection technique Values Units
[M⁻ H]⁻ 253.20000 m/z
MS²⁻ 225.10000 m/z
STD
True
TLC
False
UV/Vis detector description
UV/Vis
Mass spectrometer description
UPLC-ESI-Q-TOF-MS/MS
Organism
Rheum palmatum  L.
cultivated
fresh, powdered
Sample note
The identification of Rheum palmatum from the collected rhizome specimens were conducted by Prof. Li Xiang at the Institute of Chinese Materia Medica, China Academy of Chinese Medical Science, Beijing, China.
Dried material storage temperature
-80 °C
Extraction solvents
methanol
Extraction repeats
1
Extraction temperature
4 °C
Analysis solvents
methanol
References

J. Liu, L. Leng, Y. Liu, H. Gao, W. Yang, S. Chen, and A. Liu, "Identification and quantification of target metabolites combined with transcriptome of two rheum species focused on anthraquinone and flavonoids biosynthesis.," Scientific Reports , vol. 10 , no. 1 , pp. 20241 , DOI: 10.1038/s41598-020-77356-9 .

Analysis result 4

STD
True
TLC
False
UV/Vis detector description
photodiode array
Mass spectrometer description
Organism
Rhamnus saxatilis  Jacq.
wild
Collection dates
2008-10
Sample note
The samples were authenticated in-house by F. Tammaro (Faculty of Biotechnology, University of L'Aquila, L'Aquila, Italy). A voucher specimen (GS-2008-1) was stored at the herbarium of the Giardino dei Semplici ot the University "G. D'Annunzio" of Chieti-Pescara./Ultrasonication was used in the extraction and the extract was hydrolysed with 6N HCl.
Extraction solvents
methanol (100 %), hydrochloric acid (6N), ethyl acetate
Extraction mass/volume-ratio
100 mg/mL
Extraction repeats
1
Extraction time
1 h
Extraction temperature
20±5 °C
Extract drying method
evaporation under vacuum
Dried extract storage temperature
-20 °C
Analysis solvents
methanol
Detection note
The methanol (100%) extract was hydrolyzed and organic phases were separated with liqui-liquid extraction with ethyl acetate and dried under vacuum.
References

M. Locatelli, F. Tammaro, L. Menghini, G. Carlucci, F. Epifano, and S. Genovese, "Anthraquinone profile and chemical fingerprint of Rhamnus saxatilis L. from Italy.," Phytochemistry Letters , vol. 2 , pp. 223–226 , DOI: 10.1016/j.phytol.2009.10.001 .

Analysis result 5

Detection technique Values Units
UV/Vis 224
256
287
429 		nm
STD
True
TLC
False
UV/Vis detector description
HPLC, HPLC-UV/Vis, HPLC-PDA
Mass spectrometer description
Organism
Rheum emodii
wild
dried, powdered
Sample note
The researchers collected the rhizomes of R. emodii from western Himalaya, Himachal pradesh, from three locations, India. /The extractions were performed separately with methanol using an ultrasonicator. The same compounds were analysed from the samples of all three origins.
Drying methods
air-dried
Drying temperature
25±2 °C
Extraction solvents
methanol
Extraction mass/volume-ratio
50 mg/mL
Extraction repeats
3
Extraction time
30 min
Extract drying method
evaporation under reduced pressure
Analysis solvents
methanol
References

S. Verma, N. Singh, and A. Sinha, "Determination and locational variations in the quantity of hydroxyanthraquinones and their glycosides in rhizomes of Rheum emodi using high-performance liquid chromatography.," Journal of Chromatography A , vol. 1097 , pp. 59–65 , DOI: 10.1016/j.chroma.2005.08.018 .