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

Jed W. Fahey (Lead / Corresponding author), Katherine K. Stephenson, Albena T. Dinkova-Kostova, Patricia A. Egner, Thomas W. Kensler, Paul Talalay

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

Plant chlorophylls and carotenoids are highly colored, conjugated polyenes that play central roles in photosynthesis. Other porphyrins (tetrapyrroles), such as cytochromes, which 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 α-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'.

Original languageEnglish
Pages (from-to)1247-1255
Number of pages9
JournalCarcinogenesis
Volume26
Issue number7
DOIs
Publication statusPublished - 1 Jul 2005

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Tetrapyrroles
Chlorophyll
Carotenoids
Genes
Polyenes
Porphyrins
Photosynthesis
Phytochemicals
Cytochromes
Sulfhydryl Compounds
Oxidants
Vegetables
NAD
Oxidation-Reduction
Copper
Hepatocellular Carcinoma
Oxidoreductases
Esters
Diet
chlorophyllin

Cite this

Fahey, Jed W. ; Stephenson, Katherine K. ; Dinkova-Kostova, Albena T. ; Egner, Patricia A. ; Kensler, Thomas W. ; Talalay, Paul. / Chlorophyll, chlorophyllin and related tetrapyrroles are significant inducers of mammalian phase 2 cytoprotective genes. In: Carcinogenesis. 2005 ; Vol. 26, No. 7. pp. 1247-1255.
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Chlorophyll, chlorophyllin and related tetrapyrroles are significant inducers of mammalian phase 2 cytoprotective genes. / Fahey, Jed W. (Lead / Corresponding author); Stephenson, Katherine K.; Dinkova-Kostova, Albena T.; Egner, Patricia A.; Kensler, Thomas W.; Talalay, Paul.

In: Carcinogenesis, Vol. 26, No. 7, 01.07.2005, p. 1247-1255.

Research output: Contribution to journalArticle

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