Carbon-13 nuclear magnetic resonance: aconitine-type diterpenoid alkaloids from Aconitum and Delphinium species

Abstract

The 13C NMR spectra of the aconitine-type diterpenoid alkaloids aconitine, mesaconitine, deoxyaconitine, delphinine, chasmanine, delphisine, neoline, condelphine, isotalatizidine, as well as 17 related derivatives, have been obtained by the Fourier transform technique at 25.03 MHz. The signal due to each carbon atom has been assigned, and some previously published assignments in the alkamine, delphonine, and the alkaloid, isotalatizidine, are corrected. The spectra are analyzed in terms of substituent effects. On the basis of chemical correlation of chasmanine-neoline-delphisine, and similar values for the resonances in the 13C spectra of chasmanine, deoxyaconitine, delphinine, and delphonine, especially in the case of the ring A carbons, the configuration for the methoxyl at C-l in chasmanine has been revised to an «-equatorial methoxyl group. The results of a study of the "pyrodelphonine chromophore" in the electronic ground state of the molecule, using 13C and NMR techniques, are presented.

Physicochemical quality evaluation of natural compounds isolated from crude drugs

“…The structures of the alkaloids obtained are shown in Fig. 1, and were identified by comparing NMR, MS, UV and IR data with references [8][9][10][11][12][13]. Specification values were established by actual measurements of in-house products and/or commercial products.…”

Norditerpenoid alkaloids from Aconitum manshuricum

“…Until recently, there were few chemical studies on the constituents of A. manshuricum, and only one alkaloid, mesaconitine, had been isolated [2,3]. Reinvestigation of the constituents of this plant led to the isolation of a new norditerpenoid alkaloid named manshuritine (1), as well as seven known alkaloids; beiwudine (2) [4], beiwutine (3) [5], 16-epi-pyromesaconitine (4) [6], mesaconitine (5) [7], aconitine (6) [7], hypaconitine (7) [8] and 14-benzoylmesaconine (8) [9,10].…”

A New C19-Diterpenoid Alkaloid fromAconitum vilmorinianum

“…由于植物的 产地、气候等因素对其化学成分影响较大, 2008 年, 谭 宁 华 等 [3] 报 道 了 从 该 植 物 中 分 离 得 到 一 个 具 C(8)-C(9)-C(10)三元环体系的新骨架的 C 19 -二萜生物碱. 为了更好的开发利用我国乌头属植物的药用资源, 本课 题组对其进行更深入的系统研究, 从该植物中共分离得 到 20 个化合物(Scheme 1), 其中一个为新的 C 19 二萜生 物碱 epi-16β-hydroxycardiopetaline (1), 其余 19 个已知 化合物分别为: talatisamine (2) [4] , karakoline (3) [5] , sachaconitine (4) [6] , 14-O-veratroylneoline (5) [7] , vilmorrianine A (6) [8] , yunaconitine (7) [9] , condelphine (8) [10] , 14-acetyl-sachaconitine (9) [11] , indaconitine (10) [12] , 14-acetylkarakoline (11) [13] , 14-acetyltalatizamine (12) [14] , cammaconine (13) [15] , isotalatizidine (14) [16] , 8-deacetylyunaconitine (15) [17] , 16β-hydroxycardiopetaline (16) [18] , pseudaconine (17) [19] , columbianine (18), denudatine (19) [20] , panicutine (20) [21] . 新 化 合 物 的 结 构 应 用 HRESIMS, 1D-和 2D-NMR, 单晶 X 射线衍射等方法予 以确证.…”