Showing papers on "Isopimpinellin published in 2000"

Coumarin compounds in Ammi majus L. callus cultures.

Abstract: Callus cultures of Ammi majus L. (bishop's weed), Apiaceae, were maintained on variants of Linsmaier-Skoog's (L-S) medium differing in the content of the phytohormones, alpha-naphthaleneacetic acid (NAA) and 6-benzylaminopurine (BAP) (0.1-10.0 mg/l). The increments of callus tissue fresh weight showed considerable differences (1.4 bis 4.4-fold) during 4-week subcultures on the media tested. HPLC analysis revealed the presence of six compounds in the extracts of callus tissues, which are known metabolites in plants growing under natural conditions: the linear furanocoumarins psoralen, bergapten, xanthotoxin, isopimpinellin, imperatorin and their precursor umbelliferone. The total contents of coumarin compounds under examination showed marked differences dependent on the phytohormone concentrations in the medium. They ranged from 40.95 to 871.05 mg/100 g of dry weight. Imperatorin was the metabolite dominating among the furanocoumarins in calli from almost all tested variants of L-S medium (maximum content of 169.27 mg/100 g). Callus tissue cultured on one of the variants (0.1 mg/l NAA, 0.1 mg/l BAP) yielded in high content of xanthotoxin (145.33 mg/100 g). On the majority of media, umbelliferone was also accumulated at high quantities (maximum content of 536.29 mg/100 g). The medium containing 0.1 mg/l NAA and 0.1 mg/l BAP was the best for the accumulation of analysed coumarins. This medium favoured the formation of embryogenic callus. Xanthotoxin also dominated quantitatively among the furanocoumarins in the tested vegetative organs and fruits of the plant grown under natural conditions (leaves: 26.10 mg, roots: 5.55 mg, fruits: 3010.41 mg/100 g). Maximum contents of this metabolite in in vitro culture were many times higher than those found in vegetative plant organs but manifold lower than in fruits. On the other hand, maximum contents of imperatorin obtained in in vitro culture were many times higher in comparison with those detected in vegetative organs and fruits (leaves: 14.10 mg, roots: 3.30 mg, fruits: 94.70 mg/100 g of dry weight.). The A. majus L. callus culture, established in the course of the present experiments, can be considered a valuable model for studies of the biosynthesis of coumarin compounds, and a potential source of the psoralen 8-alkoxy derivatives imperatorin and xanthotoxin and their precursor umbelliferone.

Furanocoumarins in Pastinaca sativa L. in vitro culture.

Abstract: Callus cultures of Pastinaca sativa L. (parsnip), Apiaceae, were cultivated on variants of Linsmaier-Skoog's medium, containing varying quantities (0.1-10.0 mg/l) of phytohormones: NAA-BAP and IBA-BAP which allowed to obtain 1.5-3-fold fresh biomass growth during 6-week subcultures. HPLC analyses showed that tissues cultured in vitro produced psoralen, bergapten, xanthotoxin, isopimpinellin and umbelliferone which are well known metabolites in plants growing under natural conditions. Total content of coumarins depended on the nature and quantity of phytohormones present in the medium, and ranged from 115.7 to 408.5 mg/100 g of the dry weight, isopimpinellin being the metabolite which dominated quantitatively (maximum content of 238.9 mg/100 g). Psoralen was also accumulated in callus tissues at considerable amounts (maximum content of 108.8 mg/100 g). This metabolite dominated in vegetative plant parts that have been analysed in our study (leaves, stems, roots) but its contents were lower than in the material from in vitro culture (48.9 mg/100 g 10.6 mg/100 g and 14.9 mg/100 g, respectively). Imperatorin was not detected in callus tissues although it dominated in the analysed fruits of the studied plant (200.0 mg/100 g). The best of the tested media in respect of promoting tissue biosynthetic capabilities was that which contained 3 mg/l NAA and 1 mg/l BAP. The studies showed that in vitro cultures of Pastinaca sativa L. can be a convenient model to study the biosynthesis of furanocoumarins and also a potential rich source of these compounds, particularly isopimpinellin.

Isolation And Structure Elucidation Of 5,7-disubstituted Simple Coumarins In The Fruits Of Heracleum Mantegazzianum.

Abstract: In addition to bergapten ( 1 ), xanthotoxin ( 2 ), isopimpinellin ( 3 ), imperatorin ( 4 ), and pimpinellin ( 5 ), for the first time 5,7-disubstituted simple coumarins, limettin (5,7-dimethoxycoumarin) ( 6 ) and a new compound 5-methoxy-7-(3,3-dimethylalliloxy)-coumarin ( 7 ), have been isolated from the fruits of Heracleum mantegazzianum Somm. et Lev. The new compound 7 is a derivative of anisocoumarin B. The structures of 6 and 7 were determined on the basis of 1D and 2D NMR spectra.