Literature DB >> 24357105

Urinary 3,3'-diindolylmethane: a biomarker of glucobrassicin exposure and indole-3-carbinol uptake in humans.

Naomi Fujioka1, Cheryl E Ainslie-Waldman, Pramod Upadhyaya, Steven G Carmella, Vincent A Fritz, Charles Rohwer, Yunhua Fan, Diane Rauch, Chap Le, Dorothy K Hatsukami, Stephen S Hecht.   

Abstract

BACKGROUND: Brassica vegetable consumption may confer a protective effect against cancer, possibly attributable to their glucosinolates. Glucobrassicin is a predominant glucosinolate and is the precursor of indole-3-carbinol (I3C), a compound with anticancer effects. However, objective assessments of I3C uptake from Brassica vegetables have not been successful.
METHODS: We conducted a randomized, crossover trial to test whether 3,3'-diindolylmethane (DIM, a metabolite of I3C) excreted in the urine after consumption of raw Brassica vegetables with divergent glucobrassicin concentrations is a marker of I3C uptake from such foods. Twenty-five subjects were fed 50 g of either raw "Jade Cross" Brussels sprouts (high glucobrassicin concentration) or "Blue Dynasty" cabbage (low glucobrassicin concentration) once daily for 3 days. All urine was collected for 24 hours after vegetable consumption each day. After a washout period, subjects crossed over to the alternate vegetable. Urinary DIM was measured using a novel liquid chromatography-electrospray ionization-tandem mass spectrometry-selected reaction monitoring (LC-ESI-MS/MS-SRM) method with [(2)H2]DIM as internal standard.
RESULTS: Urinary DIM was consistently and significantly higher after Brussels sprouts feeding than after cabbage feeding, as evidenced by an average difference of 8.73 pmol/mg creatinine (95% confidence interval, 5.36-12.10; P = 0.00002).
CONCLUSION: We have successfully quantified urinary DIM after uptake of I3C from food, and demonstrated that differences in glucobrassicin exposure are reflected in urinary DIM levels. IMPACT: Our LC-ESI-MS/MS-SRM method and the results of our study indicate urinary DIM is a measure of I3C uptake from Brassica vegetables, a finding that can be utilized in prospective epidemiologic and chemoprevention studies.

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Year:  2013        PMID: 24357105      PMCID: PMC3935417          DOI: 10.1158/1055-9965.EPI-13-0645

Source DB:  PubMed          Journal:  Cancer Epidemiol Biomarkers Prev        ISSN: 1055-9965            Impact factor:   4.254


  16 in total

1.  Protection of humans by plant glucosinolates: efficiency of conversion of glucosinolates to isothiocyanates by the gastrointestinal microflora.

Authors:  Jed W Fahey; Scott L Wehage; W David Holtzclaw; Thomas W Kensler; Patricia A Egner; Theresa A Shapiro; Paul Talalay
Journal:  Cancer Prev Res (Phila)       Date:  2012-02-07

2.  LC-MS/MS quantification of sulforaphane and indole-3-carbinol metabolites in human plasma and urine after dietary intake of selenium-fortified broccoli.

Authors:  Johanna Hauder; Stefanie Winkler; Achim Bub; Corinna E Rüfer; Marc Pignitter; Veronika Somoza
Journal:  J Agric Food Chem       Date:  2011-07-06       Impact factor: 5.279

Review 3.  Molecular targets and anticancer potential of indole-3-carbinol and its derivatives.

Authors:  Bharat B Aggarwal; Haruyo Ichikawa
Journal:  Cell Cycle       Date:  2005-09-06       Impact factor: 4.534

Review 4.  Epidemiological studies on brassica vegetables and cancer risk.

Authors:  D T Verhoeven; R A Goldbohm; G van Poppel; H Verhagen; P A van den Brandt
Journal:  Cancer Epidemiol Biomarkers Prev       Date:  1996-09       Impact factor: 4.254

5.  Content of glucosinolates in cruciferous vegetables grown at the same site for two years under different climatic conditions.

Authors:  E Ciska; B Martyniak-Przybyszewska; H Kozlowska
Journal:  J Agric Food Chem       Date:  2000-07       Impact factor: 5.279

6.  Mechanisms of tumor modulation by indole-3-carbinol. Disposition and excretion in male Fischer 344 rats.

Authors:  D M Stresser; D E Williams; D A Griffin; G S Bailey
Journal:  Drug Metab Dispos       Date:  1995-09       Impact factor: 3.922

7.  Quantitative determination of 3,3'-diindolylmethane in urine of individuals receiving indole-3-carbinol.

Authors:  D W Sepkovic; H L Bradlow; M Bell
Journal:  Nutr Cancer       Date:  2001       Impact factor: 2.900

8.  Liquid chromatographic assay for the simultaneous determination of indole-3-carbinol and its acid condensation products in plasma.

Authors:  Mark J Anderton; Rebekah Jukes; John H Lamb; Margaret M Manson; Andreas Gescher; William P Steward; Marion L Williams
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2003-04-25       Impact factor: 3.205

9.  In vivo disposition of the natural anti-carcinogen indole-3-carbinol after po administration to rainbow trout.

Authors:  R H Dashwood; L Uyetake; A T Fong; J D Hendricks; G S Bailey
Journal:  Food Chem Toxicol       Date:  1989-06       Impact factor: 6.023

10.  Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice.

Authors:  Mark J Anderton; Margaret M Manson; Richard D Verschoyle; Andreas Gescher; John H Lamb; Peter B Farmer; William P Steward; Marion L Williams
Journal:  Clin Cancer Res       Date:  2004-08-01       Impact factor: 12.531

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  11 in total

1.  Intranasal delivery of liposomal indole-3-carbinol improves its pulmonary bioavailability.

Authors:  Jung Min Song; Ameya R Kirtane; Pramod Upadhyaya; Xuemin Qian; Silvia Balbo; Fitsum Teferi; Jayanth Panyam; Fekadu Kassie
Journal:  Int J Pharm       Date:  2014-10-11       Impact factor: 5.875

2.  Identification and analysis of a mercapturic acid conjugate of indole-3-methyl isothiocyanate in the urine of humans who consumed cruciferous vegetables.

Authors:  Pramod Upadhyaya; Adam T Zarth; Naomi Fujioka; Vincent A Fritz; Stephen S Hecht
Journal:  J Chromatogr B Analyt Technol Biomed Life Sci       Date:  2017-12-02       Impact factor: 3.205

3.  3,3'-diindolylmethane potentiates tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis of gastric cancer cells.

Authors:  Yang Ye; Shuhan Miao; Yan Wang; Jianwei Zhou; Rongzhu Lu
Journal:  Oncol Lett       Date:  2015-03-03       Impact factor: 2.967

4.  Harnessing the Power of Cruciferous Vegetables: Developing a Biomarker for Brassica Vegetable Consumption Using Urinary 3,3'-Diindolylmethane.

Authors:  Naomi Fujioka; Benjamin W Ransom; Steven G Carmella; Pramod Upadhyaya; Bruce R Lindgren; Astia Roper-Batker; Dorothy K Hatsukami; Vincent A Fritz; Charles Rohwer; Stephen S Hecht
Journal:  Cancer Prev Res (Phila)       Date:  2016-08-18

5.  DNA-Methyltransferase 1 Induces Dedifferentiation of Pancreatic Cancer Cells through Silencing of Krüppel-Like Factor 4 Expression.

Authors:  Victoria K Xie; Zhiwei Li; Yongmin Yan; Zhiliang Jia; Xiangsheng Zuo; Zhenlin Ju; Jing Wang; Jiawei Du; Dacheng Xie; Keping Xie; Daoyan Wei
Journal:  Clin Cancer Res       Date:  2017-06-28       Impact factor: 12.531

6.  Current Knowledge and Challenges on the Development of a Dietary Glucosinolate Database in the United States.

Authors:  Xianli Wu; Pamela R Pehrsson
Journal:  Curr Dev Nutr       Date:  2021-07-23

7.  A randomized, placebo-controlled trial of diindolylmethane for breast cancer biomarker modulation in patients taking tamoxifen.

Authors:  Cynthia A Thomson; H H Sherry Chow; Betsy C Wertheim; Denise J Roe; Alison Stopeck; Gertraud Maskarinec; Maria Altbach; Pavani Chalasani; Chuan Huang; Meghan B Strom; Jean-Philippe Galons; Patricia A Thompson
Journal:  Breast Cancer Res Treat       Date:  2017-05-30       Impact factor: 4.872

Review 8.  Chemopreventive properties of 3,3'-diindolylmethane in breast cancer: evidence from experimental and human studies.

Authors:  Cynthia A Thomson; Emily Ho; Meghan B Strom
Journal:  Nutr Rev       Date:  2016-05-31       Impact factor: 7.110

9.  Dietary Glucosinolates Sulforaphane, Phenethyl Isothiocyanate, Indole-3-Carbinol/3,3'-Diindolylmethane: Anti-Oxidative Stress/Inflammation, Nrf2, Epigenetics/Epigenomics and In Vivo Cancer Chemopreventive Efficacy.

Authors:  Francisco Fuentes; Ximena Paredes-Gonzalez; Ah-Ng Tony Kong
Journal:  Curr Pharmacol Rep       Date:  2015-01-30

10.  3,3'-Diindolylmethane Enhances Paclitaxel Sensitivity by Suppressing DNMT1-Mediated KLF4 Methylation in Breast Cancer.

Authors:  Fenfen Xiang; Zhaowei Zhu; Mengzhe Zhang; Jie Wang; Zixi Chen; Xiaoxiao Li; Tao Zhang; Qing Gu; Rong Wu; Xiangdong Kang
Journal:  Front Oncol       Date:  2021-06-03       Impact factor: 6.244

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