Isopimpinellin is a natural product synthesized by numerous plant species, especially species in the carrot family

Apiaceae Apiaceae () or Umbelliferae is a family of mostly aromatic flowering plants named after the type genus ''Apium,'' and commonly known as the celery, carrot, or parsley family, or simply as umbellifers. It is the 16th-largest family of flowering p ...

. The compound can be found in

celery Celery (''Apium graveolens'' Dulce Group or ''Apium graveolens'' var. ''dulce'') is a cultivated plant belonging to the species ''Apium graveolens'' in the family Apiaceae that has been used as a vegetable since ancient times. The original wild ...

, garden angelica,

parsnip The parsnip (''Pastinaca sativa'') is a root vegetable closely related to carrot and parsley, all belonging to the flowering plant family Apiaceae. It is a biennial plant usually grown as an annual. Its long taproot has cream-colored skin an ...

, fruits and in the rind and pulp of limes. Several studies have looked into the effects of isopimpinellin and other

furanocoumarin The furanocoumarins, or furocoumarins, are a class of organic chemical compounds produced by a variety of plants. Most of the plant species found to contain furanocoumarins belong to a handful of plant families. The families Apiaceae and Rutacea ...

s (such as

bergamottin Bergamottin (5-geranoxypsoralen) is a natural furanocoumarin found in the pulp of pomelos and grapefruits. It is also found in the peel and pulp of the bergamot orange, from which it was first isolated and from which its name is derived. Chemis ...

and imperatorin) as anticarcinogens. These studies have shown possible inhibition of 7,12-Dimethylbenz(a)anthracene, which are initiators of skin tumors. Evidence has also been reported that links these compounds to the inhibition of breast cancers.

Biosynthesis

Isopimpinellin is a

thought to be synthesized through the

mevalonate pathway The mevalonate pathway, also known as the isoprenoid pathway or HMG-CoA reductase pathway is an essential metabolic pathway present in eukaryotes, archaea, and some bacteria. The pathway produces two five-carbon building blocks called isopentenyl ...

via addition of dimethylallyl pyrophosphate ( DMAPP) to a modified coumarate known as

umbelliferone Umbelliferone, also known as 7-hydroxycoumarin, hydrangine, skimmetine, and ''beta''-umbelliferone, is a natural product of the coumarin family. It absorbs ultraviolet light strongly at several wavelengths. There are some indications that this c ...

. The biosynthesis is shown below:

References

{{coumarin Furanocoumarins O-methylated coumarins