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Carcinogenesis Advance Access published online on March 17, 2005
Carcinogenesis, doi:10.1093/carcin/bgi068
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© The Author 2005. Published by Oxford University Press. All rights reserved. For permissions, please email: journals.permissions@oupjournals.org
Received August 10, 2004
Revised February 25, 2005
Accepted March 4, 2005

MOLECULAR EPIDEMIOLOGY AND CANCER PREVENTION

Chlorophyll, chlorophyllin and related tetrapyrroles are significant inducers of mammalian phase 2 cytoprotective genes

Jed W. Fahey 1*, Katherine K. Stephenson 2, Albena T. Dinkova-Kostova 2, Patricia A. Egner 3, Thomas W. Kensler 4, and Paul Talalay 1

1 School of Medicine, Lewis B. and Dorothy Cullman Cancer Chemoprotection Center, Department of Pharmacology and Molecular Sciences, Johns Hopkins University, Baltimore, MD USA; Johns Hopkins Bloomberg School of Public Health, Johns Hopkins University, Baltimore, MD USA; Center for Human Nutrition, Johns Hopkins University, Baltimore, MD USA
2 School of Medicine, Lewis B. and Dorothy Cullman Cancer Chemoprotection Center, Department of Pharmacology and Molecular Sciences, Johns Hopkins University, Baltimore, MD USA; Johns Hopkins Bloomberg School of Public Health, Johns Hopkins University, Baltimore, MD USA
3 Department of Environmental Health Sciences, Johns Hopkins University, Baltimore, MD USA
4 School of Medicine, Lewis B. and Dorothy Cullman Cancer Chemoprotection Center, Department of Pharmacology and Molecular Sciences, Johns Hopkins University, Baltimore, MD USA; Johns Hopkins Bloomberg School of Public Health, Johns Hopkins University, Baltimore, MD USA; Department of Environmental Health Sciences, Johns Hopkins University, Baltimore, MD USA

* To whom correspondence should be addressed.
Jed W. Fahey, E-mail: jfahey{at}jhmi.edu


  Abstract

Plant chlorophylls and carotenoids are highly colored, conjugated polyenes that play central roles in photosynthesis. Other porphyrins (tetrapyrroles), such as cytochromes that are structurally related to chlorophyll, participate in redox reactions in many living systems. An unexpected new property of tetrapyrroles including tetramethyl coproporphyrin III, tetrabenzoporphine, copper chlorin e4 ethyl ester, and of carotenoids including zeaxanthin and {alpha}-cryptoxanthin is their ability to induce mammalian phase 2 proteins that protect cells against oxidants and electrophiles. The capacity of these compounds to induce the phase 2 response depends upon their ability or that of their metabolites to react with thiol groups, a property shared with all other classes of phase 2 inducers, which show few other structural similarities. Pseudo-second-order rate constants of these inducers are correlated with their potency in inducing the phase 2 enzyme NAD(P)H:quinone oxidoreductase 1 (NQO1) in murine hepatoma cells. One of the most potent inducers was isolated from chlorophyllin, a semisynthetic water-soluble chlorophyll derivative. Although chlorophyll itself is low in inducer potency, it may nevertheless account for some of the disease-protective effects attributed to diets rich in green vegetables because it occurs in much higher concentrations in those plants than the widely studied "phytochemicals."

Keywords: thiol; reactivity; phytochemicals; carotenoids; chemoprotection; pigments.
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