Aconitum species

In Turkey there are about 31 Delphinium, 8 Consolida and only 4 Aconitum species. So far we had studied 17 Delphinium, 7 Consolida and 3 Aconitum species. From these studies we have obtained more than 100 alkaloids, about 50 of them were new compounds [17]. 

Recently we have studied the fourth Turkish Aconitum species namely A. cochleare Woroschin. The aerial parts and the roots were investigated separately. From the aerial parts four alkaloids talatisamine, 14-acetyltalatisamine, cochleareine (9) and acoleareine (10) were isolated [18]. 

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... 

Aconite Aconitum species Analgesic Alkaloid, cardiac and central nervous system effects Avoid... 

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. 

Kobusine has been isolated (52, 90-92) from A. sachalinense, A. yesoense Nakai, A. lucidusculum, and A. kamtschaticum, Aconitum species native to Japan. Okamoto and co-workers (93) initially assigned structure 83 or 84... 

Isohypognavine has been isolated (99, 106) from the roots of A. majijai Nakai and A. japonicum Thumb. Its name is unfortunate since it is not an isomer of hypognavine. This alkaloid has not been isolated from any other Aconitum species. On alkaline hydrolysis, isohypognavine gave an alkamine known as isohypognavinol. On the basis of chemical correlation (107) of isohypognavine with kobusine, the partial structures 108 and 109 were... 

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... 

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... 

Diterpene (C20) and norditerpene (C19) alkaloids are typically found in species of the Aconitum, Delphinium, and Consolida genera [43-46]. The toxic effects of the Delphinium and Aconitum species can be attributed to their norditerpene alkaloid content. Thus, many of the examples presented in this chapter have been taken from the analysis of norditerpene alkaloids however, similar experiments would be applicable for any of the diterpene alkaloids (Figure 13.19). 

APCI-MS has been used extensively for the structural analysis of diterpene alkaloids from various Aconitum species for both positional and stereoiosomeric determination [ 57,58]. By controlling the drift voltage between the first and second electrodes in... 

Aconitum Species, Pages 39-40, Christine Stork and Jeanna Marraffa SummaryPlus Full Text + Links PDF (54 K)... 

See also Aconitum Species Castor Bean Hemlock, Poison Jimsonweed Oleander Proteomics. 

Mesaconitine was first isolated (103) in 1929 and occurs in a large number of Aconitum species (1). Recent reports describe its isolation from A. japonicum (104), A. mitakense (101), A. aUaicum Steinb. (105), and A. carmichalei (the Chinese drug Chuan-wu) (73). It has long been known that mesaconitine differs from aconitine only in that the former has an iV -methyl whereas the latter has an JV-ethyl (1). Both alkaloids produce oxonitine (CXXXIII) from permanganate oxidation. Hence, since the structure of aconitine has been established as CXXI, mesaconitine follows as CCV. 

In recent years a wide range of Aconitum species native to Japan and India have been examined for alkaloids. Among those encountered are several which are modeled on an atisane skeleton but possess additional ring fusions. This section will. survey the chemistry of these interesting alkaloids. 

A number of studies of the pharmacology and toxicology of the diterpenoid alkaloids have appeared.These will not be reviewed, but are cited for reference. Of particular interest is a review of the toxicity data and structure-toxicity relationships for Cl 9- and C20 alkaloids of Aconitum species. 

Mesaconitine was first isolated in 1929 (29). This alkaloid occurs in a large number of Aconitum species reported in the earlier review (1). It has also been isolated from A. japonicum (29), A. mitakense (27), A. altaicum Steinb. (30), and the Chinese drug known as Chuan-Wu (14) ( . carmi-chalei). The structure of mesaconitine as 12 was based on the structure of aconitine. Because mesaconitine differs from aconitine only in possessing an JV-methyl instead of an N-ethyl group, the structure of mesaconitine must now be revised to 13. 

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. 

These three alkaloids have been isolated from different Aconitum species talatisine (3) from the rare A. talassicum Popov, songorine (9) from A. soongoricum, and napelline (14, 15) from A. napellus L. (the main alkaloid of which is aconitine). Whilst the empirical formulas and main functional groups of these alkaloids may be considered to be firmly established, none of them has yielded degradation products or other derivatives that throw light on the nuclear structures. 

Recently we have studied the fourth Turkish Aconitum species namely... 

Soviet researchers have reported chemotaxonomical studies of Aconitum species native to the Far East. The number and levels of alkaloids varied with both the species and the habitat. Some of their results are presented in Table 1. 

Table 1 Alkaloids found in Aconitum species grown in two areas of the lower Amur basin s...

A second alkaloid, mesaconitine (34), also is widely distributed in this group of plants, and predominates in some Aconitum species. It has similar properties to aconitine. Mesaconitine (34) has an LD50 s.c. in mouse of 0.2 mg/kg (Wink, 1993). 

Aconitum alkaloids a group of terpene alkaloids, some of them very poisonous, from various aconite (Aconitum) species. The best known representative is Aconitine (see). 

---