Alkaloids, Aconitum

Ameri A. Effects of the Aconitum alkaloid songorine on synaptic transmission and paired-pulse facilitation of CA1 pyramidal cells in rat hippocampal slices. Br J Pharmacol 1998 125 461—468. 

Amiya T and Bando H (1988) Aconitum alkaloids. The Alkaloids, Chemistry and Pharmacology (ed Brossi A) Vol 34. Academic, San Diego, pp 95-179. Atta-ur-Rahman and Choudhary MI (1998) Chemistry and biology of steroidal alkaloids. The Alkaloids, Chemistry and Pharmacology (ed Cordell GA) Vol 50. Academic, San Diego, pp 61-108. Atta-ur-Rahman and Choudhary MI (1999) Diterpenoid and steroidal alkaloids. Nat Prod Rep 16, 619-635. Earlier reviews 1997, 14, 191-203 1995, 12, 361-379. 

Mizugaki, M., Ito, K., Ohyama, Y., Konishi, Y., Tanaka, S. and Kurasawa, K. (1998) Quantitative analysis of aconitum alkaloids in the urine and serum of a male attempting suicide by oral intake of aconite extract. J. Anal. Toxicol. 22, 336-340. 

Sumio Umezawa became interested in the chemistry of natural products when he joined Suginome s group in 1941 and learned of their work on isolation and structure of Aconitum alkaloids. 

Atisine is the alkaloid long known (17) to be present (to the extent of about 0.5-1 %) in the roots of atis Aconiium heterophyllum Wall.) and appears to be identical with anthorine (18), the alkaloid isolated from A. anthora L. The fact that atisine is more readily accessible and also less complex than many of the other Aconitum alkaloids has stimulated interest in its investigation since its structure may provide a guide to that of the related alkaloids. In recent years the older formulation for atisine (19) has been corrected (20) and its properties have been studied intensively, so that it has proved possible (2) to postulate a tentative structural formula (I), on the basis of which the reactions may be discussed. 

Dehydrogenation of hetisine gives (26) 1,7-dimethylphenanthrene, a distinct difference from atisine, the characteristic dehydrogenation product of which is 1,6-dimethylphenanthrene. Since 1,7-dimethylphenanthrene is also obtained (31) from abietic acid and from another Aconitum alkaloid, staphisine, the relationship between some, at least, of the Aconitum alkaloids and the diterpenes may be more than formal. 

Aconitine, identical with some fractions of japaconitine (a mixture), is the most readily accessible of the Aconitum alkaloids. It has long been known (42) and can be separated from amorphous material as the insoluble perchlorate. The confusing and contfadictory studies on aconitine reported before 1900 have been fully and critically reviewed (39). This review and the accompanying repetition and extension of earlier work (39) first corroborated the now-accepted formulation of aconitine as C34H47O11N... 

C20H26O6. Mr 362.42, mp. 297-299°C decomp., [aJo -131.3° (pyridine), a diterpene of the kaurane type bitter principle from Rabdosia trichocarpa and R. ja-ponica shows antitumor and anti-inflammatory activity against Ehrlich ascites tumors and inhibits insect growth. E. can be transformed into numerous other di-terpenes such as abietanes, Aconitum alkaloids, gib-berellins. The biosynthesis proceeds from 16-kaurene. Lit. Agric. Biol. Chem. 43, 71 (1979) Karrer, No. 3712 Zechmeister 46, 77-157. - (CAS3776-39-4]... 

Atisane is the basic skeleton of various diterpene alkaloids (aconitum-alkaloids) found in the plant families of Ranunculaceae and Garryaceae. (-)-Atisine, as a typical representative, was isolated from the Atis plant Aconitum heterophyllum (Ranunculaceae), which also contains (-)-15,20-dihydroxy-16-atisen-19-oic acid as the lactone (19,20-olide). Erythroxylon monogynum and related speeies are reported to contain (-)-16-atisene. Euphorbiaceae such as Euphorbia acaulis and E. fidjiana produce (-)-16a,17-dihydroxyatisan-3-one. (+)-13-Atisene-16p,17-diol is known as serradiol due to its natural occurrence in Sideritis serrata (Labiatae). 

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

Four Aconitum alkaloids (aconitine, mesaconitine, hypaconitine, jesaconitine) were extracted from blood and separated on a 40°C C,g colunrn (2 = 260nm for jesaconitine and 235 nm for all others). A 14/86 THF/water (0.2% TEA) mobile phase generated baseline resolution and elution in 15 min. Calibration curves from 100 to 10000ng/mL and detection limits of 50ng/mL were reported [833]. 

Forgo P, Braesa B, Csupor D, Fodor L, Berkecz R, Molnar A, Hohmann J (2011) Diterpene alkaloids freon Aconitum anthora and assessment of the hREG-inhibitory ability of Aconitum alkaloids. Planta Med 77 368-373... 

Ameri A (1998) The effects of Aconitum alkaloids on the central nervous system. Prog Neurobiol 56 211-235... 

Bao Y, Yang F, Yang X (2011) CE-electrochemiluminescence with ionic liquid forthe facile separation and determination of diester-diterpenoid aconitum alkaloids in traditional Chinese herbal medicine. Electrophoresis 32 1515-1521. doi 10.1002/elps.201100040... 

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