Alkannin

Structural formula
General
Surname	Alkannin
other names	Anchusin; ( S ) -5,8-Dihydroxy-2- (1-hydroxy-4-methyl-3-pentenyl) -1,4-naphthalenedione; CI Natural Red 20; CI 75530;
Molecular formula	C 16 H 16 O 5
Brief description	red-brown crystals
External identifiers / databases
EC number	208-245-7
ECHA InfoCard	100.007.497
PubChem	72521
ChemSpider	65430
Wikidata	Q418237
properties
Molar mass	288.30 g mol −1
Physical state	firmly
Melting point	149 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Alkannin is a dye obtained from the alkanna root ( Alkanna tinctoria ). The dye is used to color foods , cosmetics and medicines . It turns deep red in a greasy, oily environment and purple in an alkaline environment. The enantiomer of the alkannin is shikonin, the racemate is called shikalkin.

effect

Alkannin shows antimicrobial effects against Staphylococcus aureus and S. epidermidis . The drug was used as an ointment in ancient times and is used in recent studies to treat varicose veins . However, the effectiveness has not yet been adequately proven.

A derivative of shikonin, β-β-dimethylacrylshikonin, obtained from the Asian solder Onosma paniculata , could possibly drive tumor cells of black skin cancer ( melanoma ) into programmed cell death ( apoptosis ).

toxicity

Alkannin has a laxative effect and stains urine and feces. There are no known negative effects of the substance.

Individual evidence

↑ ^a ^b entry on alkannin. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Shmuel Yannai: Dictionary of Food Compounds . CRC Press, 2012, p. 478.
↑ Vassilios P. Papageorgiou, Andreana N. Assimopoulou, Elias A. Couladouros, David Hepworth, KC Nicolaou: The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products . In: Angew. Chem. Int. Ed. . 38, No. 3, 1999, pp. 270-300. doi : 10.1002 / (SICI) 1521-3773 (19990201) 38: 3 <270 :: AID-ANIE270> 3.0.CO; 2-0 .
^ ^A ^b Franz von Bruchhausen: Hager's Handbook of Pharmaceutical Practice. Springer-Verlag, 1930, ISBN 978-3-540-52688-9 , p. 179 ( limited preview in Google book search).
↑ Daniela Albat: Asian medicinal plant against skin cancer? - Active ingredient in solder root drives tumor cells to death . scinexx from September 18, 2019
↑ Nadine Kretschmer, Alexander Deutsch, Christin Durchschein, Beate Rinner, Alexander Stallinger, Juan Carlos Higareda-Almaraz, Marcel Scheideler, Birgit Lohberger, Rudolf Bauer: Comparative Gene Expression Analysis in WM164 Melanoma Cells Revealed That β-β-Dimethylacrylshiconin Leads to ROS Generation , Loss of Mitochondrial Membrane Potential, and Autophagy Induction . In: Molecules , 23 (11), October / November 2018, p. 2823, doi: 10.3390 / molecules23112823 , PMID 30380804 , PMC 6278572 (free full text).

[Römpp-1] try on alkannin. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[3] Shmuel Yannai: Dictionary of Food Compounds . CRC Press, 2012, p. 478.

[Nicolaou-4] Vassilios P. Papageorgiou, Andreana N. Assimopoulou, Elias A. Couladouros, David Hepworth, KC Nicolaou: The Chemistry and Biology of Alkannin, Shikonin, and Related Naphthazarin Natural Products . In: Angew. Chem. Int. Ed. . 38, No. 3, 1999, pp. 270-300. doi : 10.1002 / (SICI) 1521-3773 (19990201) 38: 3 <270 :: AID-ANIE270> 3.0.CO; 2-0 .

[Hager-5] A ^b Franz von Bruchhausen: Hager's Handbook of Pharmaceutical Practice. Springer-Verlag, 1930, ISBN 978-3-540-52688-9 , p. 179 ( limited preview in Google book search).

[6] Daniela Albat: Asian medicinal plant against skin cancer? - Active ingredient in solder root drives tumor cells to death . scinexx from September 18, 2019

[7] Nadine Kretschmer, Alexander Deutsch, Christin Durchschein, Beate Rinner, Alexander Stallinger, Juan Carlos Higareda-Almaraz, Marcel Scheideler, Birgit Lohberger, Rudolf Bauer: Comparative Gene Expression Analysis in WM164 Melanoma Cells Revealed That β-β-Dimethylacrylshiconin Leads to ROS Generation , Loss of Mitochondrial Membrane Potential, and Autophagy Induction . In: Molecules , 23 (11), October / November 2018, p. 2823, doi: 10.3390 / molecules23112823 , PMID 30380804 , PMC 6278572 (free full text).