845 Isopimpinellin Isopimpinellin is found in angelica. Isopimpinellin is present in the seeds of Pastinaca sativa (parsnip) Isopimpinellin belongs to the family of Furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moeity. 482-27-9 68079 C13H10O5 246.052820 White powder. 151°C Isopimpinelin strongly inhibits insulin-stimulated lipogenesis. It induces hepatic GSTs and is potent inhibitor of cytochrome P450 1A1/1B1. Oral administration of isopimpinellin, blocks DNA adducts formation and skin tumor initiation by 7,12-dimehylbenz[a]anthracene in SENCAR mice and in mouse mammary gland (L579). The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts. (L579) Not listed by IARC. IARC has assessed other furocoumarins, classifying 8-methoxypsoralen as carcinogenic to humans (Group 1), 5-methoxypsoralen as possibly carcinogenic to humans (Group 2A), and certain other furocoumarins as not being classifiable as to their carcinogenicity to humans (Group 3). (L135) The furocoumarin 8-methoxypsoralen is carcinogenic to humans, and possibly 5-methoxypsoralen as well (L135). There is some evidence from mouse studies that other furocoumarins are carcinogenic when combined with exposure to UVA radiation (A15105). The SKLM regards the additional risk of skin cancer arising from the consumption of typical quantities of furocoumarin-containing foods, which remain significantly below the range of phototoxic doses, as insignificant. However, the consumption of phototoxic quantities cannot be ruled out for certain foods, particularly celery and parsnips, that may lead to significant increases in furocoumarin concentrations, depending on the storage, processing and production conditions. (L2157) Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. All photobiological effects of furocoumarins result from their photochemical reactions. Because many dietary or water soluble furocoumarins are strong inhibitors of cytochrome P450s, they will also cause adverse drug reactions when taken with other drugs. 2009-06-08T21:38:42Z 2014-12-24T20:22:53Z C02162 28853 PHYTOALEXIN-CMPD C015304 Isopimpinelin true COC1=C2OC(=O)C=CC2=C(OC)C2=C1OC=C2 C13H10O5 InChI=1S/C13H10O5/c1-15-10-7-3-4-9(14)18-12(7)13(16-2)11-8(10)5-6-17-11/h3-6H,1-2H3 InChIKey=DFMAXQKDIGCMTL-UHFFFAOYSA-N 246.2155 246.05282343 Exogenous Solid HMDB34312 CHEMBL140796 61391