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glucoraphanin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth

Description

glucoraphanin: precursor of sulforaphane [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

glucoraphanin : A thia-glucosinolic acid that is glucoerucin in which the sulfur atom of the methyl thioether group has been oxidised to the corresponding sulfoxide. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID6602383
CHEBI ID79311
SCHEMBL ID362015
MeSH IDM0305895

Synonyms (13)

Synonym
21414-41-5
glucoraphanin
4-methylsulfinylbutyl glucosinolate
[[5-methylsulfinyl-1-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpentylidene]amino] sulfate
[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1z)-5-methylsulfinyl-n-sulfooxypentanimidothioate
1-s-[(1z)-5-(methylsulfinyl)-n-(sulfooxy)pentanimidoyl]-1-thio-beta-d-glucopyranose
CHEBI:79311
SCHEMBL362015
AKOS025117266
4-(methylsulfinyl)butyl glucosinolate
(e)-5-(methylsulfinyl)-1-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-ylthio)pentylideneaminooxysulfonic acid
(((5-(methylsulfinyl)-1-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)thio)pentylidene)amino)oxy)sulfonic acid
AS-78020

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" is safe and effectively enhances NQO1 in all tissues evaluated."( Evaluation of the safety and bioactivity of purified and semi-purified glucoraphanin.
Jeffery, EH; Keck, AS; Lai, RH; Wallig, MA; West, LG, 2008
)
0.35

Bioavailability

This is the first study to report the bioavailability of glucoraphanin and sulforaphane from soups made with novel broccoli varieties. The lower limit of quantification was 10ng/mL; calibration curves encompassed the range of plasma concentrations.

ExcerptReferenceRelevance
" Results of this study indicate that the bioavailability of ITCs from fresh broccoli is approximately three times greater than that from cooked broccoli, in which myrosinase is inactivated."( Disposition of glucosinolates and sulforaphane in humans after ingestion of steamed and fresh broccoli.
Botero-Omary, M; Chung, FL; Conaway, CC; Getahun, SM; Liebes, LL; Pusateri, DJ; Topham, DK, 2000
)
0.31
" The lower limit of quantification was 10ng/mL; calibration curves encompassed the range of plasma concentrations expected to be found in bioavailability and pharmacokinetics studies with glucoraphanin."( Direct quantitation of glucoraphanin in dog and rat plasma by LC-MS/MS.
Cwik, MJ; Kapetanovic, I; McCormick, DL; Muzzio, M; Wu, H, 2010
)
0.36
" Therefore, a cross-over clinical trial was undertaken to compare the bioavailability and tolerability of sulforaphane from two of broccoli sprout-derived beverages: one glucoraphanin-rich (GRR) and the other sulforaphane-rich (SFR)."( Bioavailability of Sulforaphane from two broccoli sprout beverages: results of a short-term, cross-over clinical trial in Qidong, China.
Botting, NP; Chen, JG; Chen, TY; Chen, YS; Egner, PA; Fahey, JW; Friesen, MD; Groopman, JD; Jacobson, LP; Kensler, TW; Lu, JH; Muñoz, A; Ng, D; Qian, GS; Sun, Y; Talalay, P; Wang, JB; Wu, Y; Zhang, Q; Zhang, YH; Zhu, J; Zhu, YR, 2011
)
0.37
" In a previous study, biomarkers of SF bioavailability from a powder rich in GRP, but lacking myrosinase, were enhanced by co-consumption of a myrosinase-containing air-dried broccoli sprout powder."( Enhancing sulforaphane absorption and excretion in healthy men through the combined consumption of fresh broccoli sprouts and a glucoraphanin-rich powder.
Cramer, JM; Jeffery, EH; Teran-Garcia, M, 2012
)
0.38
" We compared the bioavailability and metabolism of sulforaphane from portions of lightly cooked fresh or frozen broccoli, and investigated the bioconversion of sulforaphane to erucin."( Isothiocyanate concentrations and interconversion of sulforaphane to erucin in human subjects after consumption of commercial frozen broccoli compared to fresh broccoli.
Barrett, DA; Hollands, W; Kroon, PA; Mithen, RF; Narbad, A; Needs, PW; Ortori, CA; Rossiter, JT; Saha, S; Teucher, B, 2012
)
0.38
" Sulforaphane bioavailability was about tenfold higher for the soups made from fresh compared to frozen broccoli, and the reduction was shown to be due to destruction of myrosinase activity by the commercial blanching-freezing process."( Isothiocyanate concentrations and interconversion of sulforaphane to erucin in human subjects after consumption of commercial frozen broccoli compared to fresh broccoli.
Barrett, DA; Hollands, W; Kroon, PA; Mithen, RF; Narbad, A; Needs, PW; Ortori, CA; Rossiter, JT; Saha, S; Teucher, B, 2012
)
0.38
" The analytical capacity of this novel method was further tested by determining the bioavailability of GR and its metabolic derivatives in urine from volunteers after the consumption of ½ and 1 servings of broccoli sprouts (30 and 60g, respectively)."( A new ultra-rapid UHPLC/MS/MS method for assessing glucoraphanin and sulforaphane bioavailability in human urine.
Dominguez-Perles, R; Ferreres, F; García-Viguera, C; Gil-Izquierdo, Á; Medina, S; Moreno, DÁ, 2014
)
0.4
"For the first time, the effect of residual MYR activity on isothiocyanate bioavailability was systematically and quantitatively studied."( In vivo formation and bioavailability of isothiocyanates from glucosinolates in broccoli as affected by processing conditions.
Dekker, M; Oliviero, T; Verkerk, R; Vermeulen, M, 2014
)
0.4
" Measures of sulforaphane metabolites in urine indicated that bioavailability did not decline over the 12-week daily dosing period."( Rapid and sustainable detoxication of airborne pollutants by broccoli sprout beverage: results of a randomized clinical trial in China.
Carmella, SG; Chen, JG; Chen, TY; Egner, PA; Fahey, JW; Groopman, JD; Hecht, SS; Jacobson, LP; Johnson, JL; Kensler, KH; Kensler, TW; Muñoz, A; Ng, DK; Qian, GS; Talalay, P; Wang, JB; Zarth, AT; Zhu, J, 2014
)
0.4
" We have focused upon evaluating the bioavailability of sulforaphane, either by direct administration of glucoraphanin (a glucosinolate, or β-thioglucoside-N-hydroxysulfate), or by co-administering glucoraphanin and the enzyme myrosinase to catalyze its conversion to sulforaphane at economic, reproducible and sustainable yields."( Sulforaphane Bioavailability from Glucoraphanin-Rich Broccoli: Control by Active Endogenous Myrosinase.
Fahey, JW; Holtzclaw, WD; Stephenson, KK; Talalay, P; Wade, KL; Wehage, SL, 2015
)
0.42
"We evaluated the stability and bioavailability of two stabilized SF preparations-an α-cyclodextrin inclusion (SF-αCD), and an SF-rich, commercial nutritional supplement."( Stabilized sulforaphane for clinical use: Phytochemical delivery efficiency.
Fahey, JW; Fuchs, E; Holtzclaw, WD; Liu, H; Stephenson, KK; Talalay, P; Wade, KL; Wehage, SL, 2017
)
0.46
"This is the first study to report the bioavailability of glucoraphanin and sulforaphane from soups made with novel broccoli varieties."( Bioavailability of Glucoraphanin and Sulforaphane from High-Glucoraphanin Broccoli.
Dainty, JR; Melchini, A; Mithen, RF; Needs, PW; Saha, S; Sivapalan, T; Tapp, H; Traka, MH, 2018
)
0.48
"Optimization of bioavailability of dietary bioactive health-beneficial compounds is as important as increasing their concentration in foods."( Bioavailability of Isothiocyanates From Broccoli Sprouts in Protein, Lipid, and Fiber Gels.
Capuano, E; Dekker, M; Lamers, S; Oliviero, T; Verkerk, R, 2018
)
0.48
" Samples in which sulforaphane and iberin were preformed by myrosinase led to a higher bioavailability of those compounds."( Bioavailability of Isothiocyanates From Broccoli Sprouts in Protein, Lipid, and Fiber Gels.
Capuano, E; Dekker, M; Lamers, S; Oliviero, T; Verkerk, R, 2018
)
0.48
"This explorative study suggests that ITCs bioavailability can be modulated by food structure and composition and further and deeper investigations are needed to develop food products that lead to an optimized ITCs bioavailability."( Bioavailability of Isothiocyanates From Broccoli Sprouts in Protein, Lipid, and Fiber Gels.
Capuano, E; Dekker, M; Lamers, S; Oliviero, T; Verkerk, R, 2018
)
0.48
"These results conclude that when powdered brown mustard is added to cooked broccoli, the bioavailability of sulforaphane is over four times greater than that from cooked broccoli ingested alone."( Supplementation of the Diet by Exogenous Myrosinase via Mustard Seeds to Increase the Bioavailability of Sulforaphane in Healthy Human Subjects after the Consumption of Cooked Broccoli.
Ghawi, SK; Kuhnle, G; Methven, L; Niranjan, K; Okunade, O, 2018
)
0.48

Dosage Studied

ExcerptRelevanceReference
" Elimination rates were considerably slower with GRR, allowing for achievement of steady-state dosing as opposed to bolus dosing with SFR."( Bioavailability of Sulforaphane from two broccoli sprout beverages: results of a short-term, cross-over clinical trial in Qidong, China.
Botting, NP; Chen, JG; Chen, TY; Chen, YS; Egner, PA; Fahey, JW; Friesen, MD; Groopman, JD; Jacobson, LP; Kensler, TW; Lu, JH; Muñoz, A; Ng, D; Qian, GS; Sun, Y; Talalay, P; Wang, JB; Wu, Y; Zhang, Q; Zhang, YH; Zhu, J; Zhu, YR, 2011
)
0.37
" Measures of sulforaphane metabolites in urine indicated that bioavailability did not decline over the 12-week daily dosing period."( Rapid and sustainable detoxication of airborne pollutants by broccoli sprout beverage: results of a randomized clinical trial in China.
Carmella, SG; Chen, JG; Chen, TY; Egner, PA; Fahey, JW; Groopman, JD; Hecht, SS; Jacobson, LP; Johnson, JL; Kensler, KH; Kensler, TW; Muñoz, A; Ng, DK; Qian, GS; Talalay, P; Wang, JB; Zarth, AT; Zhu, J, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
sulfoxideAn organosulfur compound having the structure R2S=O or R2C=S=O (R =/= H).
thia-alkylglucosinolic acidA glucosinolic acid that is an alkylglucosinolic acid in which one on the carbons in the alkyl side-chain has been replaced by a sulfur or an oxidised sulfur.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (161)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (0.62)18.2507
2000's18 (11.18)29.6817
2010's111 (68.94)24.3611
2020's31 (19.25)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials16 (9.82%)5.53%
Reviews14 (8.59%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other133 (81.60%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]