Heating decreases epithiospecifier protein activity and increases sulforaphane formation in broccoli.

Published on May 1, 2004in Phytochemistry3.044
· DOI :10.1016/J.PHYTOCHEM.2004.04.013
Nathan V. Matusheski10
Estimated H-index: 10
(UIUC: University of Illinois at Urbana–Champaign),
John A. Juvik36
Estimated H-index: 36
(UIUC: University of Illinois at Urbana–Champaign),
Elizabeth H. Jeffery50
Estimated H-index: 50
(UIUC: University of Illinois at Urbana–Champaign)
Sources
Abstract
Sulforaphane, an isothiocyanate from broccoli, is one of the most potent food-derived anticarcinogens. This compound is not present in the intact vegetable, rather it is formed from its glucosinolate precursor, glucoraphanin, by the action of myrosinase, a thioglucosidase enzyme, when broccoli tissue is crushed or chewed. However, a number of studies have demonstrated that sulforaphane yield from glucoraphanin is low, and that a non-bioactive nitrile analog, sulforaphane nitrile, is the primary hydrolysis product when plant tissue is crushed at room temperature. Recent evidence suggests that in Arabidopsis, nitrile formation from glucosinolates is controlled by a heat-sensitive protein, epithiospecifier protein (ESP), a non-catalytic cofactor of myrosinase. Our objectives were to examine the effects of heating broccoli florets and sprouts on sulforaphane and sulforaphane nitrile formation, to determine if broccoli contains ESP activity, then to correlate heat-dependent changes in ESP activity, sulforaphane content and bioactivity, as measured by induction of the phase II detoxification enzyme quinone reductase (QR) in cell culture. Heating fresh broccoli florets or broccoli sprouts to 60 °C prior to homogenization simultaneously increased sulforaphane formation and decreased sulforaphane nitrile formation. A significant loss of ESP activity paralleled the decrease in sulforaphane nitrile formation. Heating to 70 °C and above decreased the formation of both products in broccoli florets, but not in broccoli sprouts. The induction of QR in cultured mouse hepatoma Hepa lclc7 cells paralleled increases in sulforaphane formation.
Figures & Tables
Download
📖 Papers frequently viewed together
3 Authors (Jed W. Fahey, ..., Paul Talalay)
2,212 Citations
184 Citations
161 Citations
References47
Newest
#1Niclas Petri (Uppsala University)H-Index: 5
#2Christer Tannergren (Uppsala University)H-Index: 8
Last. Gary Williamson (Nestlé)H-Index: 119
view all 14 authors...
For the first time the human intestinal effective permeability, estimated from the luminal disappearance and intestinal metabolism of phytochemicals, sulforaphane and quercetin-3,4′-glucoside, as well as the simultaneous changes in gene expression in vivo in enterocytes, has been studied in the human jejunum in vivo (Loc-I-Gut). Both compounds as components of an onion and broccoli extract could readily permeate the enterocytes in the perfused jejunal segment. At the physiologically relevant, di...
188 CitationsSource
#1Fernando Vallejo (CSIC: Spanish National Research Council)H-Index: 20
Last. Cristina García-VigueraH-Index: 67
view all 3 authors...
Total aliphatic and indole glucosinolates, phenolic compounds (flavonoids and hydroxycinnamoyl derivatives), and vitamin C contents were evaluated in freshly harvested broccoli (Brassica oleracea L., var. italica, cv. Marathon) inflorescences. These were film-wrapped and stored for 7 days at 1 °C to simulate a maximum period of commercial transport and distribution. After cold storage, inflorescences were kept for 3 days at 15 °C to simulate a retail sale period. For wrapping, low-density polyet...
187 CitationsSource
#1Richard Mithen (University of Nottingham)H-Index: 57
#2K. Faulkner (JIC: John Innes Centre)
Last. Julietta Marquez (University of Nottingham)H-Index: 8
view all 6 authors...
Broccoli florets contain low levels of 3-methylsuphinylpropyl and 4-methylsulphinylbutyl glucosinolates. Following tissue disruption, these glucosinolates are hydrolysed to the corresponding isothiocyanates (ITCs), which have been associated with anticarcinogenic activity through a number of physiological mechanisms including the induction of phase II detoxification enzymes and apoptosis. In this paper, we describe the development of ITC-enriched broccoli through the introgression of three small...
197 CitationsSource
Broccoli inflorescences have been recognized as components of healthy diets on the basis of their high content of fiber, vitamin C, carotenoids, and glucosinolates/isothiocyanates. Broccoli sprouts have been recently shown to have high levels of glucoraphanin (4-methylsulfinylbutyl glucosinolate), the precursor of the chemoprotective isothiocyanate, sulforaphane. This study evaluated the effects of temperature and developmental stage on the glucosinolate content of broccoli sprouts. Seedlings cu...
140 CitationsSource
#1Allan Brown (UIUC: University of Illinois at Urbana–Champaign)H-Index: 19
#2Gad G. Yousef (UIUC: University of Illinois at Urbana–Champaign)H-Index: 20
Last. John A. JuvikH-Index: 36
view all 7 authors...
Ten broccoli (Brassica oleracea L. (Botrytis Group)) accessions were grown in several environments to estimate glucosinolate (GS) variability associated with genotype, environment, and genotype × environment interaction and to identify differences in the stability of GSs in broccoli florets. Significant differences in genetic variability were identified for aliphatic GSs but not for indolyl GSs. The percentage of GS variability attributable to genotype for individual aliphatic compounds ranged f...
127 CitationsSource
#1Graham Basten (Norwich Research Park)H-Index: 6
#2Yongping Bao (Quadram Institute)H-Index: 35
Last. Gary Williamson (Nestlé)H-Index: 119
view all 3 authors...
Glucoraphanin in Brassica vegetables breaks down to either sulforaphane or sulforaphane nitrile depending on the conditions, and sulforaphane can be further conjugated with glutathione. Using a high-throughput microtitre plate assay and TaqMan real time quantitative RT-PCR to measure mRNA, we show that sulforaphane and its glutathione conjugate, but not the nitrile, increased significantly (P < 0.05) both UGT1A1 and GSTA1 mRNA levels in HepG2 and HT29 cells. These changes were accompanied by an ...
122 CitationsSource
#1Jed W. Fahey (JHUSOM: Johns Hopkins University School of Medicine)H-Index: 55
#2Xavier Haristoy (CNRS: Centre national de la recherche scientifique)H-Index: 2
Last. Alain Lozniewski (CNRS: Centre national de la recherche scientifique)H-Index: 26
view all 8 authors...
Gastric infection with Helicobacter pylori is a cosmopolitan problem, and is especially common in developing regions where there is also a high prevalence of gastric cancer. These infections are known to cause gastritis and peptic ulcers, and dramatically enhance the risk of gastric cancer. Eradication of this organism is an important medical goal that is complicated by the development of resistance to conventional antimicrobial agents and by the persistence of a low level reservoir of H. pylori...
672 CitationsSource
#1J. W. Chiao (NYMC: New York Medical College)H-Index: 8
#2Fung-Lung ChungH-Index: 52
Last. Conaway CcH-Index: 1
view all 6 authors...
Abstract The relation between the consumption of cruciferous vegetables and reduced prostate cancer occurrence has been documented, although the responsible phytochemicals are unknown. The effects of sulforaphane (SFN) which occurs as the precursor glucosinolate in broccoli and other cruciferous vegetables, and its metabolite N-acetylcysteine conjugate (SFN-NAC) on prostate cancer cells were investigated. SFN and SFN-NAC were analyzed with the androgen-dependent human prostate cancer LNCaP cell ...
187 CitationsSource
#1Virginia M. Lambrix (MPG: Max Planck Society)H-Index: 7
#2Michael Reichelt (MPG: Max Planck Society)H-Index: 51
Last. Jonathan Gershenzon (MPG: Max Planck Society)H-Index: 110
view all 5 authors...
Glucosinolates are anionic thioglucosides that have become one of the most frequently studied groups of defensive metabolites in plants. When tissue damage occurs, the thioglucoside linkage is hydrolyzed by enzymes known as myrosinases, resulting in the formation of a variety of products that are active against herbivores and pathogens. In an effort to learn more about the molecular genetic and biochemical regulation of glucosinolate hydrolysis product formation, we analyzed leaf samples of 122 ...
369 CitationsSource
#1Nathan V. Matusheski (UIUC: University of Illinois at Urbana–Champaign)H-Index: 10
Epidemiological and laboratory studies suggest that dietary broccoli may prevent or delay a variety of cancers. Broccoli and other crucifers contain a relatively unique family of secondary metabolites called glucosinolates. Glucoraphanin, the major glucosinolate in broccoli, is hydrolyzed by an endogenous plant myrosinase to form either the potent anticarcinogen sulforaphane (SF) or sulforaphane nitrile (SF nitrile). The bioactivities of SF and SF nitrile were compared in rats and in mouse hepat...
184 CitationsSource
Cited By213
Newest
#4Jun Liu (CAU: China Agricultural University)H-Index: 12
Source
#1Rui HeH-Index: 2
#2Meifang GaoH-Index: 1
Last. Houcheng LiuH-Index: 2
view all 7 authors...
To investigate the effects of supplementary UV-A intensity on growth and antioxidant compounds in Chinese kale (Brassica alboglabra Bailey) baby-leaves, three different UV-A intensity treatments (5, 10, 15 W·m−2, respectively) were applied 10 days before harvest in artificial light plant factory. In Chinese kale baby-leaves, supplemental 5 and 10 W·m−2 UV-A (UVA-5 and UVA-10) were beneficial for inter-node length, stem diameter, canopy diameter, fresh weight and dry weight, particularly in UVA-1...
Source
#1Liyang Wei (Hefei University of Technology)H-Index: 3
#2Changhong Liu (Hefei University of Technology)H-Index: 17
Last. Lei Zheng (Hefei University of Technology)H-Index: 29
view all 7 authors...
Source
#1Jan TřískaH-Index: 18
#2Josef Balík (Mendel University)H-Index: 9
Last. Petr Šnurkovič (Mendel University)H-Index: 2
view all 0 authors...
Broccoli sprouts contain 10–100 times higher levels of sulforaphane than mature plants, something that has been well known since 1997. Sulforaphane has a whole range of unique biological properties, and it is especially an inducer of phase 2 detoxication enzymes. Therefore, its use has been intensively studied in the field of health and nutrition. The formation of sulforaphane is controlled by the epithiospecifier protein, a myrosinase co-factor, which is temperature-specific. This paper studies...
Source
#1Iahtisham-Ul-Haq (Minhaj University Lahore)
#2Sipper Khan (University of Hohenheim)H-Index: 1
Last. Muhammad Iqbal (Minhaj University Lahore)H-Index: 57
view all 4 authors...
Sulforaphane belongs to the active class of isothiocyanates capable of delivering various biological benefits for health promotion and disease prevention. This compound is considered vital to curtail numerous metabolic disorders. Various studies have proven its beneficial effects against cancer prevention and its possible utilization as a therapeutic agent in cancer treatment. Understanding the mechanistic pathways and possible interactions at cellular and subcellular levels is key to design and...
Source
#1Wu Yuanfeng (Zhejiang University of Science and Technology)H-Index: 3
#2Lv Chengzhi (Zhejiang University of Science and Technology)H-Index: 1
Last. Mao Jianwei (Zhejiang University of Science and Technology)H-Index: 4
view all 7 authors...
Abstract The isothiocyanate sulforaphane (SF) is one of the most potent naturally occurring Phase 2 enzymes inducers derived from brassica vegetables like broccoli, cabbage, brussel sprouts, etc. Ingestion of broccoli releases SF via hydrolysis of glucoraphanin (GRP) by plant myrosinase and/or intestinal microbiota. However, both SF and plant myrosinase are thermal-labile, and the epithiospecifier protein (ESP) directs the hydrolysis of GRP toward formation of sulforaphane nitrile instead of SF....
4 CitationsSource
#1Saad M. Almuhayawi (KAU: King Abdulaziz University)H-Index: 3
#2Mohammed S. Almuhayawi (KAU: King Abdulaziz University)H-Index: 7
Last. Abdelrahim H.A. Hassan (Beni-Suef University)H-Index: 6
view all 5 authors...
Brassica sprouts are known as a good source of antimicrobial bioactive compounds such as phenolics and glucosinolates (GLs). We aim at understanding how He-Ne laser light treatment (632 nm, 5 mW) improves sprout growth and physiology and stimulates the accumulation of bioactive metabolites in three Brassica spp., i.e., mustard, cauliflower, and turnip. Moreover, how these changes consequently promote their biological activities. Laser light improved growth, photosynthesis, and respiration, which...
Source
#1Wei Zeng (USDA: United States Department of Agriculture)H-Index: 1
#2Han TaoH-Index: 1
Last. Huiying MiaoH-Index: 8
view all 9 authors...
Abstract Metabolic profiling of glucosinolates and their breakdown products in sprouts of 22 Chinese kale (Brassica oleracea var. alboglabra, BOA) varieties were investigated by using high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS). Relationships between glucosinolate metabolites and flavor of Chinese kale sprouts were also analyzed. Results showed that compositions and contents of both glucosinolates and their breakdown products varied greatly amon...
2 CitationsSource
#1Salah Abukhabta (University of Reading)H-Index: 1
#2Sameer Khalil Ghawi (University of Reading)H-Index: 6
Last. Chris I. R. Gill (Ulster University)H-Index: 28
view all 14 authors...
PURPOSE Studies on broccoli (Brassica oleracea var. italica) indicate beneficial effects against a range of chronic diseases, commonly attributed to their bioactive phytochemicals. Sulforaphane, the bioactive form of glucoraphanin, is formed by the action of the indigenous enzyme myrosinase. This study explored the role that digestion and cooking practices play in bioactivity and bioavailability, especially the rarely considered dose delivered to the colon. METHODS The antimicrobial activity of ...
4 CitationsSource
#2Jongkee Kim (CAU: Chung-Ang University)H-Index: 8
Last. Jinwook LeeH-Index: 15
view all 3 authors...
The aboveground parts of radish (Raphanus sativus L.) are typically discarded after harvesting the roots. However, numerous bioactive compounds have been identified in radish leaves, and dried leaf products have garnered attention as a health food owing to their high fiber content. Here, we assessed the morphological and physiological characteristics of the leaves of 14 commercial radish cultivars and the effects of postharvest drying treatment on their glucosinolate (GSL) contents. The morpholo...
1 CitationsSource