Heterophyllum

A. hakusanense, Nakai (Japan). Aconitine, hypaconitine, mesaconitine. A. heterophyllum.. Wall. Atisine (p. 687). 

A. heterophyllum, in which atisine was the chief alkaloid, after standing four years, yielded 8 grams of isoatisine, due to isomerisation with heter-atisine. O 4 gm., and atisine hydrochloride, 0-35 gm. ... 

Jacobs and Craig found two other alkaloids in the mother liquors accumulated during the isolation of atisine from A. heterophyllum. 

Asparagus cochinenesis (Lour.) Merr., A. falcatus Benth, A. insularis Hance, A. lucidus Lindl., A. officinalis L. Arisaema amurense Maxim., A. peninsulae Y. C. Chu et D. C. Wu, A. peninsulae Nakai, A. heterophyllum Blume,... 

Achillea alpina, A. millefolium, Arisaema amurense, A. consanguineum, A. erubescens, A. heterophyllum, A. peninsulae, A. thunbergii, Caesalpinia pulcherrima Capsella bursa-pastoris, Caragana sinica,... 

The Structure of Atidine.—An X-ray crystallographic analysis of atidine [C22H33NO3 m.pt 182.3—183.5 °C] has been reported.21 This compound has been isolated from plants of Aconitum heterophyllum Wall. Its structure was solved by direct phasing methods and refined to a final R of 0.045. Since atidine... 

Dihydroatisine, a minor alkaloid of the roots of A. heterophyllum Wall, was isolated (SO) from the strong base fraction and its structure (78) was established by comparison with the sodium borohydride reduction product of atisine or isoatisine. Recently, an X-ray analysis of dihydroatisine confirmed (30) its structure and determined the absolute configuration as 45, 55, 87 , 107 , 127 , and 155. So far dihydroatisine has not been reported in any other plant. 

Hetisine (125) was isolated as a minor alkaloid from the roots of A. heterophyllum Wall (80) in 1942 by Jacobs and Craig (118, 119). Later it was also isolated from D. cardinale Hook (120). Several papers were published (121, 122) regarding the chemistry and structure elucidation of hetisine, but the structure of hetisine (125) was eventually established by an X-ray diffraction study (123, 124). Earlier work on the chemistry of hetisine has been reviewed in Volume XII of this treatise (6). 

Hetisinone (128) has been reported to occur in D. cardinale (120), D. denudatum (126), and A. heterophyllum (80). Structure 128 originally assigned for hetisinone was confirmed (127) by H-NMR and mass spectral studies. Two other possible structures for hetisinone (134 and 135) were discarded on the basis of the following arguments. 

Hetidine has been isolated (50) in very small quantity from the strongly basic fraction of the extracts of the roots of A. heterophyllum Wall. The presence of an. V-methyl group, a tertiary methyl group, two acetylable hydroxyl functions, two ketones, and an exocyclic double bond in hetidine... 

Delphinium cardinale, D. denudatum Aconitum heterophyllum Chemically correlated with hetisine Refs. 80, 120, 126, 127... 

Alkaloids of Aconitum heterophyllum Wall.—The nature of acid-catalysed rearrangement of hetisine (61), an alkaloid isolated from A. heterophyllum and Delphinium cardinale, eluded researchers for a number of years. A compound (m.pt 278—279.5 °C) with the same molecular formula as hetisine, i.e. C20H27NO3, was isolated from A. heterophyllum. This same compound was formed by treatment of hetisine with 5% sulphuric acid.24 Wiesner and co-workers2S observed an acid-catalysed rearrangement in the formation of a methiodide of hetisine. They proposed structure (62) for this rearrangement product. 

Melampodin A Melampodium heterophyllum, M. leucanthum Insect antifeedant... 

Aconitum heterophyllum Wall, ex Royle, Ranunculaceae Atish Root Fever, cold and cough, diarrhea, piles... 

Isolation Wright isolated the alkaloid in 1878.The powdered rhizome of A. heterophyllum is extracted with a mixture of alcohol and tartaric acid by the process of percolation. On evaporation of the percolate, Atisine crystallizes. 

Hetidine (C21H27NO4). An X-ray analysis of the hydriodide of this minor base from A. heterophyllum showed it to have structure (4), from which it follows that hetidine is (5) (absolute stereochemistry assumed). Its anomalous u.v. spectrum (A ,a,j 209 nm, e 5200) and its biosynthetic interest will be discussed later. 

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