Isopimpinellin

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Isopimpinellin
Chemical structure of isopimpinellin.
Names
IUPAC name
4,9-dimethoxyfuro[3,2-g]chromen-7-one
Other names
5,8-Dimethoxypsoralen
5,8-Dimethoxypsoralene
Identifiers
482-27-9
ChEBI CHEBI:28853
ChemSpider 61391
Jmol-3D images Image
KEGG C02162
PubChem 68079
Properties
C13H10O5
Molar mass 246.21 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Isopimpinellin is a natural product synthesized by Umbelliferae (or Apiaceae), also known as the carrot or parsley family. It can be found in celery, garden angelica, parsnip, fruits and in the rind and pulp of limes.[1] There have been several studies looking into the effects of Isopimpinellin and other so-called naturally occurring coumarins (such as bergamottin and Imperatorin) as anticarcinogens.[1][2] These studies have shown possible inhibition of 7,12-Dimethylbenz(a)anthracene, which are initiators of skin tumors.[1] Evidence has also been reported that links these compounds to the inhibition of breast cancers.[2]

Biosynthesis[edit]

Isopimpinellin is a furocoumarin thought to be synthesized through the mevalonate pathway via addition of dimethylallyl pyrophosphate (DMAPP) to a modified coumarate known as umbelliferone. The biosynthesis is shown below:[3] CHEM257 - 2.png

References[edit]

  1. ^ a b c Kleiner, Heather E.; Suryanarayana V.Vulimiri; Matthew F.Starost; Melissa J.Reed; John DiGiovanni (2002). "Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice". Carcinogenesis 23 (10): 1667–1675. doi:10.1093/carcin/23.10.1667. PMID 12376476. 
  2. ^ a b Prince, Misty; Cheryl T.Campbell; Taylor A.Robertson; Amy J.Wells; Heather E.Kleiner (2006). "Naturally occurring coumarins inhibit 7,12-dimethylbenz[a]anthracene DNA adduct formation in mouse mammary gland". Carcinogenesis 27 (6): 1204–13. doi:10.1093/carcin/bgi303. PMID 16387742. 
  3. ^ Dewick, Paul M. (2009). Medicinal Natural Products: A Biosynthetic Approach (3rd ed.). UK: John Wiley & Sons Ltd. ISBN 0-471-97478-1.