Isopimpinellin

About: Isopimpinellin is a research topic. Over the lifetime, 227 publications have been published within this topic receiving 4740 citations. The topic is also known as: 5,8-Dimethoxypsoralen & 5,8-Dimethoxypsoralene.

Furocoumarins of Heracleum Laciniatum: isolation, phototoxicity, absorption and action spectra studies

Abstract: Isolation of the furocoumarins (psoralens) bergapten, isobergapten, sphondin, isopimpinellin and pimpinellin from the Umbilliferous plant Heracleum laciniatum was carried out by column chromatography, and the structure and absorption spectra for the 5 furocoumarins isolated are described. Photoepicutaneous testing showed the strongest phototoxic effects from bergapten, marked effects from pimpinellin, weak effects from sphondin and none from the others. These in vivo findings were confirmed by the in vitro Candida test. Action spectrum studies demonstrated peak photosensitivity in the range 330-335 nm, bergapten being more than twice as phototoxic as pimpinellin.

Foeniculum vulgare Mill. A Medicinal Herb

Abstract: Foeniculum vulgare .Mill. commonly known as Fennel belonging to the family Apiaceae , is a small, erect and aromatic herb. A number of chemical constituents and various therapeutic effects of this herb have been reported by different workers. Extensive investigations have been carried out on different parts of herb and as a consequence, varied classes of compoundsfatty acids, hydrocarbons and sterols, Fu­rocoumarins; (imperatorin, psoralen, ber­gapten, xanthotoxin and isopimpinellin), Flavonoids; (isorhamnetin 3-O-α-rhamnoside, quercetin and kaempferol) and quercetin; (3-O-rutinoside, kaempferol 3-O-rutinoside and quercetin 3-O- β-glucoside) have been isolated . So, it has been used in ethnomedicine to exploit its medicinal properties including antioxidant, anti-inflammatory, anticancer, antifungal, antibacterial, antinociceptive, anti-inflammatory and antiviral activities. The presented review summarizes the information about the ethnopharmacology, toxicity, phytochemistry and biological activity of F. vulgare .

Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy via screening of a natural product repository.

Abstract: CYP1A1 is thought to mediate carcinogenesis in oral, lung and epithelial cancers. In order to identify a CYP1A1 inhibitor from an edible plant, 394 natural products in the IIIM's natural product repository were screened, at 10 μM concentration, using CYP1A1-Sacchrosomes™ (i.e. microsomal enzyme isolated from recombinant baker's yeast). Twenty-seven natural products were identified that inhibited 40–97% of CYP1A1's 7-ethoxyresorufin-O-deethylase activity. The IC50 values of the ‘hits’, belonging to different chemical scaffolds, were determined. Their selectivity was studied against a panel of 8 CYP-Sacchrosomes™. In order to assess cellular efficacy, the ‘hits’ were screened for their capability to inhibit CYP enzymes expressed within live recombinant human embryonic kidney (HEK293) cells from plasmids encoding specific CYP genes (1A2, 1B1, 2C9, 2C19, 2D6, 3A4). Isopimpinellin (IN-475; IC50, 20 nM) and karanjin (IN-195; IC50, 30 nM) showed the most potent inhibition of CYP1A1 in human cells. Isopimpinellin is found in celery, parsnip, fruits and in the rind and pulp of limes whereas different parts of the Indian beech tree, which contain karanjin, have been used in traditional medicine. Both isopimpinellin and karanjin negate the cellular toxicity of CYP1A1-mediated benzo[a]pyrene. Molecular docking and molecular dynamic simulations with CYP isoforms rationalize the observed trends in the potency and selectivity of isopimpinellin and karanjin.