Delphinium species

TLC and HPLC have been applied for the separation of the flower pigments of some Delphinium species. Anthocyanins were extracted with 70 per cent aqueous ACN containing... 

K. Honda, K. Tsutsui and K. Hosokawa, Analysis of the flower pigments of some Delphinium species and their interspecific hybrids produced via ovule culture. Sci. Hort. 82 (1999) 125-134. 

Chemical and Biological Studies with anAconitum and a Delphinium Species... 

The last Delphinium species we have investigated was D. linearilobum (Trautv.) N.Busch [20], from this plant we have isolated six known and two new compounds. The knownalkaloids were lycoctonine, 14-acetyltalatisamine,browniine,cammaconine, talatisamine and cochlearenine, the new alkaloids were named as linearilobin (12) and linearilin (13). 

Gardner DR, Panter KE, Pfister JA, Knight AP. 1999. Analysis of toxic norditerpenoid alkaloids in Delphinium species by electrospray, atmospheric pressure chemical ionization, and sequential tandem mass spectrometry. J Agric Food Chem 47 5049. 

The larkspur (Delphinium) species are generally divided into three... 

The diterpenoid alkaloids, isolated mainly from Aconitum and Delphinium species (Ranunculaceae), have been of great interest since the early 1800s because of their pharmacological properties. Extracts of Aconitum species were used in ancient times for treatment of gout, hypertension, neuralgia, rheumatism, and even toothache. Extracts have also been used as arrow poisons. Some Delphinium species are extremely toxic and constitute a serious threat to livestock in the western United States and Canada. Delphinium extracts also manifest insecticidal properties. In the last 30 to 40 years, interest in the diterpenoid alkaloids has increased because of the complex structures and interesting chemistry involved. 

Five new diterpenoid alkaloids have been isolated from Aconitum species (Ranunculaceae) and five from Delphinium species (Ranunculaceae). Four new Anopterus (Escalloniaceae) bases have been identified. The most significant synthetic achievement has been the total synthesis of racemic chasmanine. A detailed review of the alkaloids of Delphinium staphisagria has appeared.1... 

In a similar utilization of MS markers, the total ion chromatograms derived for extracts of Delphinium species vere scanned for the presence of toxic alkaloids (Section 13.6.1). 

Whilst gas chromatography has been used for the analysis of many of the lycoctonine-based alkaloids [52], the larger, less volatile, and more thermally labile MSAL compounds require analytical procedures such as TLC and HPLC for separation and detection. For example, both normal phase liquid chromatography [53] and reversed phase liquid chromatography [54] with UV detection have been used for separation, detection, and quantitation of alkaloids from Delphinium species associated with livestock poisonings in the western US and Canada. The introduction of API techniques has allowed the analysis of all types of diterpene alkaloids by direct MS methods and with MS methods coupled to liquid chromatography. 

Both normal phase [53] and reversed phase [54] HPLC methods have been used for the separation of diterpene alkaloids. Reversed phase HPLC coupled to APCI mass spectrometry has been used for the analysis of diterpene alkaloids of Aconitum spp. [64,65] and normal phase HPLC conditions [53] have been successfully used with APCI-MS for the detection of diterpene alkaloids in Delphinium species [56]. However, caution should be observed in the use of APCI sources with some normal phase HPLC solvents such as hexane, to ensure no oxygen is introduced into the system producing a possible explosive mixture in the API source. 

Fig. 13.23 Plot of the first three canonical variables from the discriminant analysis of the tabulated ESI-MS data for toxic Delphinium species according to Ewan [59]. Croups A and B are Delphinium barbeyi, group C is D. occidentale, group D is D. glaucum, and group E is a hybrid (barb, x occi.).

The structures of a number of new C19 alkaloids that have been obtained from various Aconitum and Delphinium species have been reported. These include ranaconitine from A. ranunculaefolium, septentrioine and septentriodine from A. septentrionale, delbiterine from D. biternatum, " and gadesine from D. pentagynum. These are reviewed in the Specialist Periodical Report on the Alkaloids. 

Rheum palmatum (rhubarb) Aconitum napellus (monkshood) Cimicifuga racemosa (black cohosh) Delphinium species (delphinium) Hydrastis canadensis (golden seal) Pulsatilla species (pasque flower) Ranunculus damascenus (buttercup)... 

Delphinium species contain complex diterpenoid alkaloids that cause acute intoxication and death in cattle (6). The alkaloids and their concentrations vary with the species and plant part involved, which causes variability in toxicity. In Delphinium consolida (larkspur) there are toxic alkaloids in the non-medicinal plant parts (root, seed, herb), but they are purportedly absent in the medicinal part (the flower). 

Research on diterpenoid alkaloids published during the past year has continued to expand the body of structural and synthetic information available on these complex plant bases. The structures of ten new alkaloids from Aconitum and Delphinium species, including seven new bisditerpenoid alkaloids, have been reported. Tlie most significant progress in methods of structure elucidation has been the very successful applications of n.m.r. to the study of complex diterpenoid alkaloids. The New Bruns wick group under Professor Karel Wiesner has continued its progress toward the syntheses of the Ci9-aconitine-type alkaloids. An historical account of the synthesis of talatisamine (1), the first synthesis of a hexacyclic aconite alkaloid, has been published. This work was reviewed in a previous Report. ... 

Another study of the bases from five Delphinium species in Armenia produced at least five new alkaloids 181). From D.flexuosum was isolated methyllycaconitine, two unnamed crystalline compounds, base A (C35H54N2O8) and base B (C18H29NO7), and base C, mp... 

The alkaloid content of the aerial parts of four Delphinium species growing in the Tran Shan region of the USSR was studied and found to vary markedly depending on the location and the year of harvest 182). The results are summarized in the following tabulation ... 

V. Miscellaneous Alkaloids Isolated from Aconitum and Delphinium Species 328... 

The two genera Aconitum and Delphinium, which belong to the family Ranunculaceae, produce several series of closely related monobasic alkaloids. In fact, the same alkaloid may be found in different species of the two genera thus, isotalatisidine and its acetyl ester condelphine occur in A. talassicum and in D. confusum, respectively, and esters of lycoctonine occur in A. lycoctonum and in several Delphinium species. On the other hand, closely similar plant species (e.g., A. septentrioncde and A. lycoctonum, and a series of East Asian Aconitum species) may be differentiated by their content of related but different bases. 

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