Colchicum Species Research Articles

A New Colchicinoid from Colchicum tauri, an Unexplored Meadow Saffron Native to Jordan

This study reports the isolation, characterization, and biological evaluation of constituents of Colchicum tauri Siehe ex Stef. (Colchicaceae), an unexplored Colchicum species native to Jordan. Methanolic extraction, crude alkaloid fractionation, and separation using several different chromatographic techniques (open columns, preparative TLC, and semi-preparative HPLC), as directed by the brine shrimp lethality test (BST), resulted in the isolation and identification of nine compounds: (-)-colchicine (1), (-)-2-demethylcolchicine (2), (-)-3-demethylcolchicine (3), (-)-demecolcine (4), (-)- N-methyldemecolcine (5), (-)-3-demethyl- N-methyldemecolcine (6), β-lumicolchicine (7), 3-demethyl-β-lumicolchicine (8), and apigenin (9). Compounds 1–5 and 7–8 were isolated for the first time from this species, while compound (6) represents a new colchicinoid. The structure elucidations were achieved using a series of spectroscopic and spectrometric techniques, principally 1D-NMR (1H, and 13C), 2D-NMR (COSY, ROESY, HMBC, and HSQC), and low resolution EI-MS. All compounds were tested for general toxicity using the BST, and compounds 1 and 4 were found to be the most potent, with LC50 values of 2.5 and 8.1 μg/mL, respectively.

Morphological and Anatomical Investigations on Some Species of Colchicum L. Occurring in South East Anatolia, Turkey

Morphological and Anatomical Investigations on Some Species of Colchicum L. Occurring in South East Anatolia, Turkey

New Colchicinoids from a Native Jordanian Meadow Saffron, Colchicum brachyphyllum: Isolation of the First Naturally Occurring Dextrorotatory Colchicinoid

As part of our continuing investigation of Jordanian Colchicum species, the biologically active components of Colchicum brachyphyllum were pursued. Using bioactivity-directed fractionation, nine colchicinoids were isolated and characterized. One of these has a novel ring system, to which we have ascribed the trivial name (+)-demecolcinone (9), and it represents the first naturally occurring dextrorotatory colchicinoid. Another isolated compound was a new colchicinoid analogue, (-)-2,3-didemethyldemecolcine (8), while the remaining seven known colchicinoids were new to the species: (-)-colchicine (1), (-)-3-demethylcolchicine (2), (-)-cornigerine (3), beta-lumicolchicine (4), (-)-androbiphenyline (5), (-)-demecolcine (6), and (-)-3-demethyldemecolcine (7). The brine shrimp lethality test was used to direct the isolation of these colchicinoids. Moreover, all pure compounds were evaluated for cytotoxicity against a human cancer cell panel, for antimicrobial activity in an array of bacteria and fungi (including yeast), and for their potential to be allosteric modulators of the gamma-aminobutyric acid type A receptor.

Cytometric determination of genome size in Colchicum species (Liliales, Colchicaceae) of the western Mediterranean area

Genome size has been studied for the first time in the Colchicum genus. Values obtained by flow cytometry were quite stable and specific to each taxon: C. autumnale L., 2C=5.89±0.22 pg, equivalent to 5.7×109 bp (2n=4x=36); C. alpinum DC., 2C=8.06±0.24 pg, equivalent to 7.8×109 bp (2n=6x=56); C. lusitanum Brot., 2C=10.7±0.67 pg, equivalent to 10.3×109 bp (2n= approx. 10x=90–92 and 94–96); C. multiflorum Brot., 2C=16.5±0.69 pg, equivalent to 15.9×109 bp, (2n= approx. 16x=140–148); C. corsicum Baker, 2C=21.3±0.99 pg, equivalent to 20.6×109 bp (2n=22x= approx. 198±2). These values are well below those published for Liliaceae stricto sensu. In Colchicum species from the western Mediterranean area, genome size was highly correlated with ploidy level (R 2=0.99, P<0.001). This relationship is consistent with most previous results, with our new chromosome number count for C. corsicum and with our correction of published erroneous counts for C. lusitanum (2n=102–108). The Calabrian population appeared to be distinct from all of the other plants of the C. alpinum group. Reproducible and accurate, cytometry appears to be a particularly appropriate method for studying this polyploid genus in Western Europe, taking into account that chromosome numbers are difficult to enumerate. It can guide future taxonomic research because it reveals similarities or differences between taxa within this difficult complex.

Determination of Colchicine Content in Colchicum Hierosolymitanum and Colchicum Tunicatum Under Cultivation

Corms of Colchicum hierosolymitanum and Colchicum tunicatum were collected, identified and planted under field condition. We report here and for the first time the presence of colchicine in an appreciable amount in both species. The effect of different NPK fertilizer levels on colchicine content of the two Colchicum species at different growth stages were evaluated by HPLC. Results indicated that increasing NPK fertilizer levels significantly improve colchicine content in different plant parts and stages. The highest colchicine content observed in corms was at maturity stage 0.766 mg/g and 0.688 mg/g dry weight with C. hierosolimitanum and C. tunicatum , respectively.

A new soboliferous species of Colchicum in Turkey

Abstract A new species, Colchicum leptanthum K.Perss. (Colchicaceae), endemic to north-east Turkey, is described. The species is early spring-flowering (±winter-flowering), and has soboliferous corms, a feature it shares with only eight other species of the genus. The chromosome number is 2 n =18.

A new soboliferous species of Colchicum in Turkey

A new species, Colchicum leptanthum K.Perss. (Colchicaceae), endemic to north-east Turkey, is described. The species is early spring-flowering (±winter-flowering), and has soboliferous corms, a feature it shares with only eight other species of the genus. The chromosome number is 2 n=18.

The genus Colchicum in Turkey: I. New species

Six new species of Colchicum (Colchicaceae) are described (C. munzurense, C. minutum, C. sanguicolle, C. micaceum, C. heldreichii, C. inundatum). The first two flower in early spring with synanthous leaves, the rest are autumn-flowering. All are endemic to Turkey, and confined to small geographical areas. Chromosome numbers and notes on phenology, vegetative reproduction, phytogeography and ecology are provided for all the species.

The genus Colchicum in Turkey. II. Revision of the large-leaved autumnal species

Turkish autumn-flowering species of Colchicum (Colchicaceae) with large, broad hysteranthous leaves are taxonomically and morphologically revised, with comments on conditions in other areas covered by the distributions. Three new species are described (C. paschei, C. dolichantherum, C. imperatoris-friderici), all endemic to Turkey. Synonym lists, typifications, chromosome numbers, and notes on phenology, vegetative reproduction, phytogeography and ecology are provided for the whole group, and relationships to other species are discussed.

Une nouvelle espèce corse de Colchique: Colchicum arenasii sp. nov. (Liliaceae)

Summary A new species of Colchicum (C. arenasii) having tessellated tepals is described. It is compared to other Corsican and Sardinian species of hysteranthous Colchicum. The five species occurring in Corsica are keyed out. Some indications about distribution and ecology are given.

New and revised species ofColchicum (Colchicaceae) from the Balkan Peninsula

Three new species ofColchicum (Colchicaceae) are described (C. chimonanthum, C. rausii, C. confusum), all confined to Greece. The first one flowers in very early spring, the other two are autumn-flowering with hysteranthous leaves appearing in the spring. Revisions are included of two other autumn-flowering species (C. haynaldii andC. autumnale) which are geographically over-lapping with and may be confused withC. confusum. Synonym lists, typifications, chromosome numbers, and notes on differences from other species, phenology, vegetative reproduction, phytogeography and ecology are provided for all.

Chromatographic determination of constituents of the genus Colchicum (Liliaceae)

A high-performance liquid chromatographic method for the determination of colchicinoid alkaloids in plant material is described. The determination is performed separately in neutral and basic alkaloid fractions using a C 18-bonded silica column. Nine alkaloids, i.e., 3-demethylcolchicine, 2-demethylcolchicine, colchifoline, N-deacetyl-N-formylcolchicine, colchicine, cornigerine, 2-demethyldemecolcine, 3-demethyldemecolcine and demecolcine, in seven Colchicum plants were assayed. For identification of phenolic compounds, a method using gas chromatography-mass spectrometry was elaborated and twenty phenolic compounds were identified in extracts from five Colchicum species. As the presence of luteolin appeared to be of value for chemotaxonomic purposes, its simple densitometric determination was developed.

The Dibenzocycloheptylamine Alkaloids

Androcymbium palaestinum of Jordanian origin has 2 yielded the new alkaloid (―)-androbiphenyline, which in CDCl 3 solution exists as 2 conformers. Two previously known and related alkaloids are K-3 and K-4 obtained from a colchicum species (―)-androbiphenyline, K-3, and K-4 are the only known representatives of the dibenzocycloheptylamine class of alkaloids

Alkaloids and Phenolics ofColchicum cilicicum1,2

The distributions of the alkaloids colchicine, 2-demethylcolchicine, 3-demethylcolchicine, demecolcine, 2-demethyldemecolcine, and 3-demethyldemecolcine in the corms, stems, leaves, flowers, and seeds of COLCHICUM CILICICUM were analysed by HPLC. In addition, the alkaloids cornigerine, N-formyl- N-deacetylcolchicine, N-methyl-demecolcine, beta-lumicolchicine, gamma-lumicolchicine, beta-lumidemecolcine, gamma-lumidemecolcine, and N-ethoxycarbonyldemecolcine were identified, the last named being reported for the first time from a COLCHICUM species. The flavones luteolin and apigenin were isolated and benzoic, 2-hydroxy-6-methoxybenzoic, and vanillic acids were also detected.

Alkaloids of Colchicum visiani*

From the bulbs, flowers and flowerstalks of Colchicum visiani Parl. of Yugoslavian origin, were isolated and identified the neutral-phenolic and alkaline alkaloids listed in Table II. This investigation showed that the alkaloid content of Colchicum visiani Parl. is similar to that of Colchicum autumnale L., with the exception of a tropolonic alkaloid hR (f)-16 (found as well in Colchicum dörfleri) and a tropolonic alkaloid hR (f)-13, which had so far been unidentified in Colchicum species.

Biosynthesis of the indole and Colchicum alkaloids.

Abstract

Phytochemical investigations of some species of Colchicum

Abstract A colorimetric assay for colchicine and its congeners has been devised. It is based on the yellow colour produced by the treatment of these alkaloids with mineral acid and is useful over the range 0·0005–0·0025% w/v. Together with the method of Pesez (1957) it has been used to assay extracts of species of Colchicum and the individual alkaloids were identified by paper chromatography. It was concluded that C. tunicatum, a native of Israel, contained sufficient colchicine to make it a useful source of this alkaloid.

DIAGNOSTIC ANATOMICAL FEATURES OF CERTAIN SPECIES OFCOLCHICUM

The histological features of the epidermises of the brown scale leaf and foliage leaf of six species of Colchicum are described, together with some features of the bulb scales of some other liliaceous plants. It is considered that species of Colchicum can be best distinguished by the presence or absence of papillae, proteinoplasts, beads and cuticular depressions around the stomata of the epidermis of the foliage leaf. The epidermis of the brown scale leaf is diagnostic only in C. ritchii, where it is lignified, but its appearance serves to distinguish species of Colchicum from the other liliaceous plants examined.

Plant Distribution in the Northern Hemisphere

PLANT GEOGRAPHY is the study of the existing distribution of floras and plant communities, and the underlying causes of this distribution and its bearing on the evolution of plants. The plant geographer is particularly interested in how a particular plant or a particular plant community reached a certain area and how the present distributions of floras have come about. Plant geography is a very complex subject, because so many different factors are responsible for the distribution of plants. The subject is so large that I am confining my remarks to giving very shortly some of the main factors that affect the distribution of plants in the northern hemisphere, and illustrating it by showing how these factors apply in one genus, Paeonia, which is confined to the northern hemisphere. During the ages the geography of the world has continually changed, some? times quickly but more often slowly, hardly perceptibly. Meanwhile climate has also changed. Climate is one of the main factors determining the distribu? tion of plants. It is a complex factor, introducing not only heat and cold, but also humidity and the amount of sunshine. All species of plants have a certain tolerance of climate; for instance, certain plants such as Dryas octopetala, the dwarf birch, and Rubus arcticus will grow in Greenland, while other plants, like the olive, require a Mediterranean climate. The climate of the Mediterranean area is very different from that of central Europe. The hot dry summers and main rainfall in a mild winter encourage the growth of evergreen trees, like the olive, the evergreen oaks, and the myrtles, and also plants, such as most species of cyclamen and colchicum, which are dormant during the hot summers andflower with the autumn rains, so that they grow and ripen their seed during the mild winters. In central Europe on the other hand the trees are largely deciduous, like the apple, flowering late in spring and fruiting in the autumn. Other types of plants growing on high mountains, such as the lovely little Eritrichium nanum and the species $oldanella, require a long resting period under the snow, where they lie prdtected all the winter until, with the hot sun and damp ground conditions of summer, growth begins again. These are just a few examples of plant behaviour under different sorts of climate.