Lipid of the Month

Each month we highlight a lipid of scientific interest. The LIPID MAPS® Lipid of the Month Archive lists lipids highlighted from 2015 - present.

September 2024

Lipid of the month Bergamottin

For reasons which are unimportant, your Lipid of the Month author has quite a lot of sparkling grapefruit drinks at home. Fortunately, your author is not on any medication, as certain drugs and grapefruit can be a bad combination.

The cause, possibly among others, is a molecule found in grapefruit called bergamottin, which was identified nearly 90 years ago1. It’s a furanocoumarin flavonoid linked to a geranyl chain, so really both a polyketide and a prenol combined. Along with related compounds, such as dihydroxybergamottin, it affects metabolism of many drugs, including some very common ones, for instance some used to treat high blood pressure or high cholesterol2.

It isn’t that bergamottin reacts with drugs directly, but rather it inhibits cytochrome P450 enzymes which metabolise those drugs. Drugs are administered at a dose which takes this into account, so inhibiting the enzyme can effectively lead to overdosing3. Alternatively, if the drug is administered in a pre- form, relying on enzymes to convert it to the active form, under dosing can occur as the active drug isn’t produced in the expected amount.

That’s not to say that grapefruit is bad for you, it’s a source of vitamin C and there’s even a suggestion that bergamottin itself has potential as an anticancer agent4. Your author will continue enjoying the beverage- in moderation, obviously. Cheers!

References

  • Uber Bergamottin und über die Auffindung von Limettin im Bergamottol (XXXIV. Mitteil. uber naturliche Cumarine)
    Berichte der Deutschen chemischen Gesellschaft
    1937
    DOI 10.1002/cber.19370701115
  • The effects of fruit juices on drug disposition: a new model for drug interactions
    Eur J Clin Invest
    2003
    DOI 10.1046/j.1365-2362.33.s2.2.x
  • Grapefruit–medication interactions: Forbidden fruit or avoidable consequences?
    CMAJ
    2013
    DOI 10.1503/cmaj.120951
  • Pharmacological Utilization of Bergamottin, Derived from Grapefruits, in Cancer Prevention and Therapy
    Int J Mol Sci
    2018
    DOI 10.3390/ijms19124048

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