Alkaloids from Delphinium Species

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. 

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... 

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). 

Perhaps the most important examples of terpenoid alkaloids from a pharmacological point of view are those found in aconite or wolfsbane (Aconitum species Ranunculaceae) and species of Delphinium (Ranunculaceae). Whilst Aconitum... 

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. 

Even though much is already known about the toxicity of diterpene alkaloids that contribute to the toxicity of Consolida, Delphinium, and Aconitium species, no antiviral study has been so far reported on this type of alkaloids. Therefore, no SAR studies have been encountered by us on the antiviral or antimicrobial activities of these alkaloids. However, a quantitative SAR analysis performed on a number of diterpene alkaloids isolated from an Aconitum sp. indicated that biological activity of these alkaloids may be related to their toxicity rather than to a specific pharmacological action [40]. In a current study on 43 norditerpenoid alkaloids from Consolida, Delphinium, and Aconitum species against several tumor cell lines, lycoctonine and browniine were... 

Alkaloids of Delphinium elisabethae.—Soviet researchers28 have reported the isolation of an alkaloid fraction from the roots of this species by extraction with methanol-acetic acid-water. From this mixture they separated five alkaloids. On... 

Alkaloids of Delphinium formosum.—Tanker and Ozden29 obtained an alkaloid fraction from the roots of this species, growing in Turkey, by treatment with ammonium hydroxide and benzene percolation. Thin-layer-chromatographic separation afforded six alkaloids. Two of these were identified as lycoctonine (39) and delsemine (see Alkaloids of D. tricorne , p. 228). 

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. 

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. ... 

DITERPENE ALKALOIDS FROM ACONITUM, DELPHINIUM, AND GARRYA SPECIES THE C -DITERPENE ALKALOIDS... 

The alkaloid condelphine (CCCLII) was first isolated in 1942 from Delphinium confusum Popov and was found to be an 0-acetate derivative of isotalatizidine (CCCLIII) (142). The latter alkaloid, along with its C-1 epimer talatizidine (CCCLIV), had been isolated 2 years earlier from Aconitum talassicum Popov, a rare species native to the mountainous... 

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... 

Structural and synthetic studies of the diterpene alkaloids of the Aconitum, Delphinium, and Garrya species continue to provide more insight into the chemistry of these complex bases. In recent years Japanese workers have isolated a series of isoprenoid alkaloids from plants of Daphniphyllum macropodum Miquel. Structural work on four new alkaloids representing three new structural types has been reported during this year. 

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

MISCELLANEOUS ALKALOIDS ISOLATED FROM ACONITUM AND DELPHINIUM SPECIES... 

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