Sulforaphane

Structural formula
	( R ) -Sulforaphan (top) and ( S ) -Sulforaphan (bottom)
General
Surname	Sulforaphane
other names	( RS ) -1-Isothiocyanato-4-methylsulfinylbutane; ( R ) -1-Isothiocyanato-4-methylsulfinylbutane; ( S ) -1-Isothiocyanato-4-methylsulfinylbutane;
Molecular formula	C 6 H 11 NOS 2
Brief description	slightly yellowish liquid
External identifiers / databases
PubChem	5350
Wikidata	Q424489
properties
Molar mass	177.29 g · mol -1
boiling point	130-135 ° C (4 Pa)
solubility	almost insoluble in water; moderate in DMSO (40 g l −1 );
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sulforaphane , chemically 1-isothiocyanato-4-methylsulfinyl-butane, is an isothiocyanate . The mustard oil is produced by the enzymatic hydrolysis of the mustard oil glycoside glucoraphanin .

Properties and occurrence

Sulforaphane is a powerful indirect antioxidant . It was first isolated and described in 1992 by Paul Talalay and colleagues at Johns Hopkins University in Baltimore .

The secondary plant substance occurs as mustard oil glycoside glucoraphanin, especially in cruciferous plants such as cabbage and broccoli . In contrast to vitamin C , vitamin E or β-carotene, the active ingredient does not neutralize free radicals directly, but indirectly by activating phase II enzymes . This sets the body's long-term antioxidant defense mechanisms in motion.

Various studies have both in cell culture and in animal experiments , a tumor cell inhibitory effect are detected by sulforaphane. Certain components of dividing cancer cells, the so-called microtubules , are supposed to be destroyed by sulforaphane, which leads to the death of the cancer cell. Sulforaphane is currently (as of September 2012) in a large number of clinical studies . For example, in a phase II study for the treatment of prostate cancer .

In more recent experimental studies from Heidelberg University Hospital and the German Cancer Research Center , it has been shown that the ingredient sulforaphane from broccoli and related vegetables can inhibit the growth of pancreatic cancer and intensify the effects of chemotherapy. Sulforaphane blocks a certain metabolic pathway in cancer stem cells, which was shown for the first time in experiments on cancer cells and mice. According to a Canadian study, the weekly consumption of broccoli or cauliflower is said to reduce the metastasis of the tumor by 50 percent in patients with prostate cancer . In addition, the active substance is against the germ-killing stomach ulcer -Verursacher Helicobacter pylori act, even against strains that to common antibiotics resistance have formed.

metabolism

Metabolism of sulforaphane via the mercapturic acid route . (1) : glutathione ; (2) : sulforaphane; (3) : glutathione adduct; (4) : cysteine - glycine adduct; (5) : cysteine adduct; (6) : N -acetylcysteine adduct; (7) : erucine ; GST : glutathione S-transferase ; GTP : γ-glutamyl transpeptidase ; CGase : cysteine glycinase ; AT : Acetyltransferase (structural formulas without stereochemistry)

In mammals, sulforaphane is broken down and excreted mainly by means of a glutathione-S-transferase , in which it is converted into a dithiocarbamate , the thiol group of glutathione being added to the isothiocyanate group of sulforaphane. After the enzymatic cleavage of glutamic acid and glycine, an N -acetylcysteine adduct is formed by acetylation , which was found in animal experiments on rats (together with the glutathione adduct) in urine and bile . Sulforaphane can also lead to its thioether - analogue Erucin reduced are the exact mechanisms to are as yet unclear.

literature

BM Kaminski, D. Steinhilber u. a .: Phytochemicals resveratrol and sulforaphane as potential agents for enhancing the anti-tumor activities of conventional cancer therapies. In: Current Pharmaceutical Biotechnology . Volume 13, Number 1, January 2012, pp. 137-146, PMID 21466425 . (Review).
YS Keum: Regulation of the Keap1 / Nrf2 system by chemopreventive sulforaphane: implications of posttranslational modifications. In: Annals of the New York Academy of Sciences . Volume 1229, July 2011, pp. 184-189, doi : 10.1111 / j.1749-6632.2011.06092.x . PMID 21793854 . (Review).
CW Beecher: Cancer preventive properties of varieties of Brassica oleracea: a review. In: The American journal of clinical nutrition. Vol. 59, Number 5 Suppl, 1994, pp. 1166S-1170S, PMID 8172118 . (Review). PDF (free full text access, in English)
C. Fimognari, P. Hrelia: Sulforaphane as a promising molecule for fighting cancer. In: Mutation Research . Volume 635, number 2-3, 2007, pp. 90-104, doi : 10.1016 / j.mrrev.2006.10.004 . PMID 17134937 . (Review).
N. Juge, RF Mithen, M. Traka: Molecular basis for chemoprevention by sulforaphane: a comprehensive review. In: Cellular and molecular life sciences. Volume 64, Number 9, 2007, pp. 1105-1127, doi : 10.1007 / s00018-007-6484-5 . PMID 17396224 . (Review).

Individual evidence

↑ ^a ^b ^c ^d data sheet DL-Sulforaphane from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).
↑ Entry on mustard oils. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.
↑ CE Guerrero-Beltrán, M. Calderón-Oliver u. a .: Protective effect of sulforaphane against oxidative stress: recent advances. In: Experimental and Toxicologic Pathology . Volume 64, Number 5, July 2012, pp. 503-508, doi : 10.1016 / j.etp.2010.11.005 . PMID 21129940 .
↑ Y. Zhang, P. Talalay et al. a .: A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. In: PNAS . Volume 89, Number 6, March 1992, pp. 2399-2403, PMID 1549603 . PMC 48665 (free full text).
↑ Y. Zhang, TW Kensler u. a .: Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. In: PNAS. Volume 91, Number 8, April 1994, pp. 3147-3150, PMID 8159717 . PMC 43532 (free full text).
↑ clinicaltrials.gov: Sulforaphane. Retrieved September 25, 2012.
↑ Clinical study (phase II): Sulforaphane in Treating Patients With Recurrent Prostate Cancer at Clinicaltrials.gov of the NIH
↑ G. Kallifatidis, S. Labsch u. a .: Sulforaphane increases drug-mediated cytotoxicity toward cancer stem-like cells of pancreas and prostate. In: Molecular therapy. Volume 19, number 1, January 2011, pp. 188-195, doi : 10.1038 / mt.2010.216 . PMID 20940707 . PMC 3017446 (free full text).
↑ Annette Tuffs: Award-winning research results: How broccoli active ingredients support cancer therapy. Heidelberg University Hospital, press release from June 12, 2012 from Informationsdienst Wissenschaft (idw-online.de), accessed on August 24, 2015.
↑ JK Moon, JR Kim et al. a .: Analysis and anti-Helicobacter activity of sulforaphane and related compounds present in broccoli (Brassica oleracea L.) sprouts. In: Journal of agricultural and food chemistry . Volume 58, Number 11, June 2010, pp. 6672-6677, doi : 10.1021 / jf1003573 . PMID 20459098 .
↑ JW Fahey, X. Haristoy et al. a .: Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo [a] pyrene-induced stomach tumors. In: PNAS. Volume 99, Number 11, May 2002, pp. 7610-7615, doi : 10.1073 / pnas.112203099 . PMID 12032331 . PMC 124299 (free full text).
↑ X. Haristoy, K. Angioi-Duprez et al. a .: Efficacy of sulforaphane in eradicating Helicobacter pylori in human gastric xenografts implanted in nude mice. In: Antimicrobial agents and chemotherapy . Volume 47, Number 12, December 2003, pp. 3982-3984, PMID 14638516 . PMC 296232 (free full text).
↑ Ann Liza Piberger: Investigations into the influence of sulforaphane on the repair of DNA single-strand breaks and nucleotide excision . February 13, 2014, p. 5-9 , doi : 10.5445 / IR / 1000043295 .

Web links

sciencedaily.com: UIC Researchers Show How Cancer-Preventing Foods Work , July 13, 2005

[Sigma-1] ta sheet DL-Sulforaphane from Sigma-Aldrich , accessed on May 29, 2011 ( PDF ).

[2] Entry on mustard oils. In: Römpp Online . Georg Thieme Verlag, accessed on September 29, 2014.

[PMID21129940-3] CE Guerrero-Beltrán, M. Calderón-Oliver u. a .: Protective effect of sulforaphane against oxidative stress: recent advances. In: Experimental and Toxicologic Pathology . Volume 64, Number 5, July 2012, pp. 503-508, doi : 10.1016 / j.etp.2010.11.005 . PMID 21129940 .

[PMID1549603-4] Y. Zhang, P. Talalay et al. a .: A major inducer of anticarcinogenic protective enzymes from broccoli: isolation and elucidation of structure. In: PNAS . Volume 89, Number 6, March 1992, pp. 2399-2403, PMID 1549603 . PMC 48665 (free full text).

[PMID8159717-5] Y. Zhang, TW Kensler u. a .: Anticarcinogenic activities of sulforaphane and structurally related synthetic norbornyl isothiocyanates. In: PNAS. Volume 91, Number 8, April 1994, pp. 3147-3150, PMID 8159717 . PMC 43532 (free full text).

[6] trials.gov: Sulforaphane. Retrieved September 25, 2012.

[7] Clinical study (phase II): Sulforaphane in Treating Patients With Recurrent Prostate Cancer at Clinicaltrials.gov of the NIH

[PMID20940707-8] G. Kallifatidis, S. Labsch u. a .: Sulforaphane increases drug-mediated cytotoxicity toward cancer stem-like cells of pancreas and prostate. In: Molecular therapy. Volume 19, number 1, January 2011, pp. 188-195, doi : 10.1038 / mt.2010.216 . PMID 20940707 . PMC 3017446 (free full text).

[9] Annette Tuffs: Award-winning research results: How broccoli active ingredients support cancer therapy. Heidelberg University Hospital, press release from June 12, 2012 from Informationsdienst Wissenschaft (idw-online.de), accessed on August 24, 2015.

[PMID20459098-10] JK Moon, JR Kim et al. a .: Analysis and anti-Helicobacter activity of sulforaphane and related compounds present in broccoli (Brassica oleracea L.) sprouts. In: Journal of agricultural and food chemistry . Volume 58, Number 11, June 2010, pp. 6672-6677, doi : 10.1021 / jf1003573 . PMID 20459098 .

[PMID12032331-11] JW Fahey, X. Haristoy et al. a .: Sulforaphane inhibits extracellular, intracellular, and antibiotic-resistant strains of Helicobacter pylori and prevents benzo [a] pyrene-induced stomach tumors. In: PNAS. Volume 99, Number 11, May 2002, pp. 7610-7615, doi : 10.1073 / pnas.112203099 . PMID 12032331 . PMC 124299 (free full text).

[PMID14638516-12] X. Haristoy, K. Angioi-Duprez et al. a .: Efficacy of sulforaphane in eradicating Helicobacter pylori in human gastric xenografts implanted in nude mice. In: Antimicrobial agents and chemotherapy . Volume 47, Number 12, December 2003, pp. 3982-3984, PMID 14638516 . PMC 296232 (free full text).

[13] Ann Liza Piberger: Investigations into the influence of sulforaphane on the repair of DNA single-strand breaks and nucleotide excision . February 13, 2014, p. 5-9 , doi : 10.5445 / IR / 1000043295 .