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Sulforaphane Glucosinolate Monograph

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Sulforaphane Glucosinolate Monograph amr Monograph Sulforaphane Glucosinolate Monograph Introduction of a basic structure consisting of a β-D-thioglucose Intake of broccoli sprouts, a rich source of the group, a sulphonated oxime group, and an amino glucosinolate glucoraphanin, has been associated acid-derived side chain.17 Glucosinolates must be with decreased incidence, multiplicity, and tumor enzymatically hydrolyzed to their associated growth in animal cancer models.1-3 In 1992, Paul isothiocyanate to become active.18 Sulforaphane Talalay, MD, and colleagues at Johns Hopkins (molecular formula C6H11NOS2) is the biologically University identified the isothiocyanate, sulfora- active isothiocyanate produced when glucora- phane, a biologically active metabolite of glucora- phanin is metabolized by the enzyme myrosinase phanin, as the compound in broccoli responsible (Figure 1).19 for many of its health benefits.4 Since that time, more than 500 studies have been conducted on the Pharmacokinetics mechanisms and biological activity of sulforaphane Glucoraphanin in broccoli is enzymatically and its precursor, glucoraphanin.5 Glucoraphanin, hydrolyzed by myrosinase, an enzyme compart- also referred to as sulforaphane glucosinolate mentally separated from glucoraphanin in plant (SGS), is the most potent naturally-occurring cells. Myrosinase is released when the plant is inducer of phase 2 detoxification enzymes4,6 and is chewed or processed.20 Heating broccoli partially an indirect, long-acting antioxidant.7-9 denatures and inactivates myrosinase, leaving the Sulforaphane also exhibits broad-spectrum glucoraphanin at least partially intact. In the gut of antimicrobial activity against numerous gram- healthy individuals any intact glucoraphanin is positive and -negative bacteria,10 most notably then metabolized by myrosinase-producing Helicobacter pylori.11 In addition, sulforaphane bacteria.21 Because broccoli sprout or seed extracts possesses anti-inflammatory activity; it inhibits taken orally contain no myrosinase to hydrolyze cytokine production in preclinical and clinical the glucoraphanin, transformation to sulforaphane studies.12-14 Sulforaphane’s multiple molecular must be carried out by the gut microflora.22 In targets and promising early research have led to individuals with compromised intestinal flora and 15 clinical trials currently underway to assess its low myrosinase activity, it is unclear if glucora- effects on various cancers, cardiovascular disease, phanin exerts the same systemic effects as upper airway inflammation, radiation dermatitis, observed in individuals with normal intestinal and vascular health.15 flora.23 Research in humans indicates approximately 74 Biochemistry percent of sulforaphane from broccoli extract is Glucoraphanin is a glucosinolate found in high absorbed in the jejunum.24 After absorption, concentrations in the Mariner variety of broccoli sulforaphane is metabolized via the mercapturic (Brassica oleracea italica) and other members of the acid pathway.25,26 Although this pathway involves a Brassica family.16 All glucosinolates are comprised complex interplay between the liver, small Volume 15, Number 4 Alternative Medicine Review 352 Copyright © 2010 Alternative Medicine Review, LLC. All Rights Reserved. No Reprint Without Written Permission. Monograph amr Figure 1. Glucoraphanin Metabolism HO O HO OH Glucose O S S H2O C CH OH 2 Myrosinase S N=C=S N OSO 3 HSO - 4 Sulforaphane Glucoraphanin (Sulforaphane glucosinate) intestine, and kidneys, the liver is thought to be Mechanisms of Action the primary site of activity and is the site of Indirect Antioxidant and Carcinogen Detoxification sulforaphane conjugation to glutathione. Sulforaphane is a pleotropic molecule and a Sulforaphane-glutathione conjugates are subse- potent inducer of numerous nuclear factor ery- quently converted to cysteinyl-glycine, cysteine, throid-derived 2 (Nrf2)-dependent phase 2 and N-acetylcysteine conjugates in the kidneys or enzymes involved in xenobiotic detoxification. gut and then cycled back to the liver for acetylation. Enzymes induced by sulforaphane include the Of these conjugates, sulforaphane-N-acetylcysteine antioxidant response element (ARE) targets: is the most prevalent.21 NQO1,4 γ-glutamylcysteine synthetase (GGCS),31 Upon absorption into the bloodstream, sulfora- HO-1,32 glutathione transferases (GST),33 glucuro- phane readily accumulates in tissue and exerts nosyl transferases,34 and epoxide hydrolases.35 anticarcinogenic effects. In one human study, a These enzymes are regulated by the Nrf2 transcrip- single 200 µM dose of sulforaphane from broccoli tion factor, which upon release from the Kelch-like sprouts yielded peak plasma concentrations ECH-associated protein 1 (KEAP1), binds to ARE between 0.943 and 2.27 µmol/L at one hour post sites in the enzymes’ genes and upregulates feeding; the half life of sulforaphane was 1.77 ± carcinogen detoxification.36,37 Other Nrf2-mediated 0.13 hours.27 A pilot study in eight healthy women effects of sulforaphane include inhibition of LDL undergoing reduction mammoplasty demonstrated oxidation,38 inhibition of dopamine oxidation,39 a broccoli sprout extract containing 200 µM improvement of age-related TH1 immunity via Key words: sulforaphane, sulforaphane given orally one hour prior to tissue restoration of redox equilibrium,40 and reduction of broccoli, glucoraphanin, SGS, isothiocyanate, Crucera, removal resulted in average tissue uptake of 1.45 ± oxidative stress caused by electrophilic carcino- 41 detoxification, detox, 1.12 pmol/mg in the left breast and 2.00 ± 1.95 gens. Sulforaphane also modulates phase 1 phase 2, phase II, pmol/mg in the right breast. Both detoxification cytochrome p450 (CYP) enzymes by decreasing H. pylori, Helicobacter, Brassica, cruciferous, enzyme genes for NADH quinone reductase CYP1A1, CYP2B1/2, and CYP3A4 activity, thereby chemoprotection, (NQO1) and heme oxygenase-1 (HO-1) were inhibiting the activation of procarcinogens and chemoprotectant, measureable in the excised breast tissue, indicating preventing the generation of DNA adducts during anticarcinogen, carcinogen, 42 cancer, inflammation, cancer blocking activity after sulforaphane con- the initiation stage of cancer. The overall net 28 Gilbert’s syndrome, sumption. Research in mice has also demon- effect on phase 1 and 2 enzymes is an increase in anti-inflammatory, strated colonic tissue uptake of sulforaphane after metabolism and detoxification of chemical antioxidant, Nrf2 oral dosing, accompanied by a reduction in carcinogens.43 adenoma formation.29 Excretion of sulforaphane conjugates in the urine is via first-order kinetics Other Chemopreventive Mechanisms with metabolites being cleared from the body Sulforaphane exerts a direct effect on human within 72 hours of dosing.27,30 cancer cells post-initiation. Research has demon- strated sulforaphane directly inhibits cell cycle 44,45 progression, primarily via G2M arrest, and induces apoptosis of cancer cells via caspase 353 Alternative Medicine Review Volume 15, Number 4 Copyright © 2010 Alternative Medicine Review, LLC. All Rights Reserved. No Reprint Without Written Permission. amr Monograph activation, resulting in reduced tumor weight and Miscellaneous Mechanisms volume both in vitro and in animal cancer Sulforaphane’s anti-inflammatory effects have models.45,46 In human tissue samples, reductions in been attributed to inhibition of pro-inflammatory histone acetylation correlate with increased cancer signaling molecules and cytokines13 such as NFκB, grade and risk of cancer recurrence.47 Studies show prostaglandin E2, and nitric oxide.12 Sulforaphane sulforaphane directly inhibits histone deacetylase also appears to reduce upper airway inflammation (HDAC), which correlates with induction of G2M via increased phase 2 enzyme detoxification of air cell cycles arrest and apoptosis.48 Sulforaphane also pollutants and pollen, apparently via decreased appears to upregulate apoptosis in cancer cells by cellular oxidative stress, inhibition of inflamma- modulating nuclear factor kappaB (NFκB) activity49 tory cytokine production, and decreased tissue and increasing mitochondrial reactive oxygen inflammation.14 In vitro research has also shown species, causing disruption of mitochondrial sulforaphane inhibits the production of interleukin membrane potential and release of cytochrome C.50 and tumor necrosis factor-alpha (TNF-α) in And finally, sulforaphane potently inhibits angio- rheumatoid T cells.53 Sulforaphane exhibits genesis and metastasis of tumors by reducing broad-spectrum antimicrobial activity, inhibiting microcapillary formation and inhibiting cell the growth of several gram-positive and -negative migration.51 These effects were associated with bacteria, including E. coli 0157:H7, Helicobacter down regulation of angiogenesis factors, including pylori, Salmonella, Shigella, Staphylococcus aureus, vascular endothelial growth factor (VEGF).52 Figure Streptococcus pyogenes, Pseudomonas aeruginosa, and 2 summarizes the tumor inhibition effects of Cryptococcus neoformans.10,11 sulforaphane. Figure 2. Sulforaphane Mechanisms of Tumor Inhibition Sulforaphane Induction of Phase 2 Antibiotic Response H. Pylori Indirect Variable Eects Antioxidant on Phase I Eects Anti- Cell Cycle Inammatory Arrest & Apoptosis Tumor Inhibition Volume 15, Number 4 Alternative Medicine Review 354 Copyright © 2010 Alternative Medicine Review, LLC. All Rights Reserved. No Reprint Without Written Permission. Monograph amr Clinical Indications Clinical Studies Cancer The first direct
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