Pimpinellin CAS NO.131-12-4

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Chemical Properties of Pimpinellin

Source of Pimpinellin

The fruits of Psoralea corylifolia L.

Biological Activity of Pimpinellin

Protocol of Pimpinellin

Preparing Stock Solutions of Pimpinellin

References on Pimpinellin

The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.[Pubmed:23501157]

J Ethnopharmacol. 2013 May 2;147(1):232-7.

ETHNOPHARMACOLOGICAL RELEVANCE: Heracleum maximum is amongst the most commonly used plants by the indigenous peoples of North America. The First Nations of the eastern Canada use infusions of Heracleum maximum roots for the treatment of respiratory ailments including tuberculosis. Previous investigations of extracts derived from the roots of Heracleum maximum have shown it to possess antimycobacterial activity. AIM OF THE STUDY: To isolate and identify antimycobacterial constituents from the roots of Heracleum maximum. MATERIALS AND METHODS: A methanolic extract of Heracleum maximum roots was subjected to bioassay guided fractionation using the microplate resazurin assay (MRA) to assess inhibitory activity against Mycobacterium tuberculosis strain H37Ra. The antimycobacterial constituents were identified by NMR, MS and polarimetry. RESULTS: The polyacetylene (3R,8S)-falcarindiol and the furanocoumarins bergapten, isobergapten, angelicin, sphondin, Pimpinellin, isoPimpinellin and 6-isopentenyloxyisobergapten were isolated from the Heracleum maximum root extract. (3R,8S)-Falcarindiol and 6-isopentenyloxyisobergapten exhibited MICs of 24 muM and 167 muM and IC50s of 6 muM and 27 muM against Mycobacterium tuberculosis H37Ra respectively. The remaining furanocoumarins bergapten, isobergapten, angelicin, sphondin, Pimpinellin, and isoPimpinellin were less active, with MICs of 925, 1850, 2149, 1859, 812 and 1625 muM and IC50s of 125, 344, 350, 351, 389 and 406 muM. CONCLUSIONS: (3R,8S)-Falcarindiol, bergapten, isobergapten, angelicin, sphondin, Pimpinellin, isoPimpinellin and 6-isopentenyloxyisobergapten were identified as the principal constituents responsible for the antimycobacterial activity of the roots of Heracleum maximum. This work supports the ethnopharmacological use of Heracleum maximum by Canadian First Nations and Native American communities as a treatment for infectious diseases, specifically tuberculosis.

Simultaneous determination of pimpinellin, isopimpinellin and phellopterin in rat plasma by a validated UPLC-MS/MS and its application to a pharmacokinetic study after administration of Toddalia asiatica extract.[Pubmed:22418072]

J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Apr 1;891-892:102-8.

A rapid and selective ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was developed for simultaneous determination of three bioactive coumarins of Toddalia asiatica extract including Pimpinellin, isoPimpinellin and phellopterin in rat plasma for the first time. Phenacetin was used as the internal standard (IS). Plasma samples were extracted by liquid-liquid extraction with methyl tert-butyl ether. The chromatographic separation was carried out on an ACQUITY UPLC BEH C(1)(8) column with an isocratic mobile phase consisting of methanol-5 mmol/L ammonium acetate (65:35, v/v). The detection was performed on a triple quadrupole tandem mass spectrometer by multiple reaction monitoring (MRM) via electrospray ionization (ESI) source with positive ionization mode. The method was linear for all analytes over investigated range with all correlation coefficients greater than 0.9942. The lower limits of quantification (LLOQ) were 25.0 ng/mL for Pimpinellin, 10.0 ng/mL for isoPimpinellin and 5.00 ng/mL for phellopterin. The intra- and inter-day precision (RSD%) was within 12% and the accuracy (RE%) ranged from -2.3% to 5.5%. The rapid and sensitive method was fully validated and successfully applied to the pharmacokinetic study of Pimpinellin, isoPimpinellin and phellopterin in rats following oral administration of Toddalia asiatica extract.

Discovery and antitumor activities of constituents from Cyrtomium fortumei (J.) Smith rhizomes.[Pubmed:23379693]

Chem Cent J. 2013 Feb 4;7(1):24.

UNLABELLED: BACKGROUND: Cyrtomium fortumei (J.) Smith is an important Chinese herbal medicine because of its biological functions. However, systematic and comprehensive studies on the phytochemicals from Cyrtomium fortumei (J.) Smith and their bioactivity are limited. RESULTS: Using the bioassay-guided technique, the ethyl acetate and n-BuOH extracts of the rhizomes of Cyrtomium fortumei (J.) Smith were shown to exhibit good antitumor activities, consequently leading to the isolation of 23 compounds. All compounds were isolated from the plant for the first time. The inhibitory activities of these compounds were investigated on tumor cells MGC-803, PC3, and A375 in vitro by MTT (thiazolyl blue tetrazolium bromide) assay, and the results showed that Pimpinellin (3) had potent cytotoxic activities against the three cell lines, with the IC50 values of 14.4 +/- 0.3 muM, 20.4 +/- 0.5 muM, and 29.2 +/- 0.6 muM, respectively. The mechanism of the antitumor action indicated that Pimpinellin inhibited the growth of MGC-803 cells via the induction of tumor cell apoptosis, with apoptosis ratio of 27.44% after 72 h of treatment at 20 muM. CONCLUSIONS: This study suggests that most of the compounds from the roots of Cyrtomium fortumei (J.) Smith could inhibit the growth of human carcinoma cells. Moreover, Pimpinellin inhibited the growth of tumor cells via the induction of tumor cell apoptosis.

Phototoxicity from furocoumarins (psoralens) of Heracleum laciniatum in a patient with vitiligo. Action spectrum studies on bergapten, pimpinellin, angelicin and sphondin.[Pubmed:6627920]

Contact Dermatitis. 1983 Sep;9(5):364-6.

Investigations on light reactions in a patient with vitiligo are presented. The minimal erythema dose (MED) in the UVB area was approximately 1/3 of that in persons of skin type II. The application of furocoumarins (psoralens) increased light tolerance by 1 MED at 300-310 nm. Action spectrum studies with furocoumarins from Heracleum laciniatum showed the following order of potency: bergapten, Pimpinellin, angelicin and sphondin. The efficacy was highest at 325-350 nm, with maxima at 330-335 nm. Pimpinellin was recently found to be phototoxic, but an action spectrum of sphondin is reported for the first time.

Description

Pimpinellin is a constituent of Cyrtomium fortumei (J.). Pimpinellin inhibits the growth of tumor cells via the induction of tumor cell apoptosis.

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