Chasmanthinine

A reexamination of the roots of Aconitum chasmanthum revealed the presence of four new alkaloids—chasmaconitine, chasmanthinine, chasmanine, and homochasmanine—in addition to indaconitine which was originally described in 1905 (124). Chasmanine and homochasmanine will be discussed in the following section. 

Chasmanthinine is the first diterpene alkaloid of this family that has been found to be esterified with cinnamic acid. Since chasmanthinine has been correlated with bikhaconine, whose absolute configuration is known, the absolute configuration of chasmanthinine is also known. 

Chasmaconitine and chasmanthinine, two closely related alkaloids, were isolated (68) during reexamination of the roots of A. chasmanthum. The structure and stereochemistry of chasmaconitine (38) were assigned on the basis of the conversion of this alkaloid to delphinine. Since the structure of delphinine has been revised, chasmaconitine must be represented by structure 40. Chasmanthinine was also correlated with chasmaconitine and other alkaloids, and structure 39 was originally assigned to it. With the revision of the structure of chasmaconitine, the structure for chasmanthinine must be revised to 41. Thus far, neither of these two alkaloids has been isolated from any other plants. 

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