Journal
CHEMICO-BIOLOGICAL INTERACTIONS
Volume 192, Issue 1-2, Pages 72-80Publisher
ELSEVIER IRELAND LTD
DOI: 10.1016/j.cbi.2010.10.007
Keywords
Biological reactive intermediates; Botanical dietary supplements; Chemoprevention; Electrophiles; Epoxides; Carbocations; Nitrenium ions; Quinones
Funding
- NCCIH NIH HHS [P50 AT00155, P50 AT000155] Funding Source: Medline
- NCI NIH HHS [CA135237, R21 CA135237] Funding Source: Medline
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The use of botanical dietary supplements is increasingly popular, due to their natural origin and the perceived assumption that they are safer than prescription drugs. While most botanical dietary supplements can be considered safe, a few contain compounds, which can be converted to biological reactive intermediates (BRIs) causing toxicity. For example, sassafras oil contains safrole, which can be converted to a reactive carbocation forming genotoxic DNA adducts. Alternatively, some botanical dietary supplements contain stable BRIs such as simple Michael acceptors that react with chemosensor proteins such as Keap1 resulting in induction of protective detoxification enzymes. Examples include curcumin from turmeric, xanthohumol from hops, and Z-ligustilide from dang gui. Quinones (sassafras, kava, black cohosh), quinone methides (sassafras), and epoxides (pennyroyal oil) represent BRIs of intermediate reactivity, which could generate both genotoxic and/or chemopreventive effects. The biological targets of BRIs formed from botanical dietary supplements and their resulting toxic and/or chemopreventive effects are closely linked to the reactivity of BRIs as well as dose and time of exposure. (C) 2010 Elsevier Ireland Ltd. All rights reserved.
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