Lepenine and Denudatine: New Alkaloids from<i>Aconitum kusnezoffii</i>

Uhrı́n, Dušan; Proksa, B.; Zhamiansan, J.

doi:10.1055/s-2006-960125

Cited by 21 publications

(14 citation statements)

References 1 publication

(1 reference statement)

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“…Herein, we describe the isolation and structural elucidation of the two new compounds. 4,5 The 1D NMR spectral data (Table 1) were similar to those of denudatine 6 except that there was an N=CH group in compound 1, instead of the NCH 2 CH 3 in denudatine. The existence of a double bond between the N and C-19 was finally verified by the HMBC correlations (Figure 2) between the olefinic proton of H-19 (δ H 7.29, br.s) and C-3, C-4, C -5, C-18 and C-20.…”

Section: Introductionmentioning

confidence: 67%

Two New Diterpenoid Alkaloids from Aconitum brachypodum

Shen¹,

Zuo²,

Jiang³

et al. 2010

Bulletin of the Korean Chemical Society

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Section: Introductionmentioning

confidence: 67%

Two New Diterpenoid Alkaloids from Aconitum brachypodum

Shen¹,

Zuo²,

Jiang³

et al. 2010

Bulletin of the Korean Chemical Society

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“…C-NMR spectrum suggested that the two moieties of this bis-C 20 -diterpenoid alkaloid consist of a denudatine-type C 20 -diterpenoid-alkaloid moiety and an atisine-type C 20 -diterpenoid-alkaloid moiety [1]. Comparison of the NMR data of the denudatine moiety of piepunine with those of denudatine [7], a representative denudatine-type C 20 -diterpenoid alkaloid, revealed that they shared a similar NMR spectral pattern. The presence of the denudatine moiety was confirmed by the correlations Me(18)/C(19), CH 2 (19)/C(20), HÀC(20)/C(8), and HÀC(7)/C(10) in the HMBC spectrum (Fig.…”

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confidence: 89%

Piepunine, A Novel Bis‐diterpenoid Alkaloid from the Roots of Aconitum piepunense

Cai

Song

Chen

et al. 2010

Helvetica Chimica Acta

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Further investigation on the roots of Aconitum piepunense led to the isolation of a novel bisditerpenoid alkaloid designated as piepunine (1). Its structure was established by extensive interpretation of its 1D-and 2D-NMR data, high-resolution ESI-MS, and IR spectra. Piepunine represents the first example of an atisine -denudatine-type bis-diterpenoid alkaloids.Introduction. -Diterpenoid alkaloids display a wide range of interesting bioactivities and chemical properties, as well as toxic and structural complexity. Most of these diterpenoid alkaloids were isolated from various species of Aconitum and Delphinium. Structurally, diterpenoid alkaloids can be classified as C 18 -, C 19 -, and C 20 -diterpenoid alkaloids. An entire and update profile of each type of diterpenoid alkaloids was described by us in The Alkaloids edited by Cordell [1 -3]. The naturally rare bis-diterpenoid alkaloids could be regarded as a class of C 20 -diterpenoid alkaloids. So far, only four types, namely the atisine -hetidine type, rearranged atisine -hetidine type, denudatine -denudatine type, and the heteratisine -hetidine type, of bisditerpenoid alkaloids have been isolated from nature [1].Aconitum piepunense Hand-Mazz. Symb. Sin. belongs to the genus Aconitum in the Ranunculaceae, and is distributed mainly at an altitude of over 3000 m in the northwest of Yunnan Province in China [4]. Our earlier chemical investigation on this plant led to the discovery of some new C 18 -and C 19 -diterpenoid alkaloids [5] [6]. Further investigation on the minor components of this plant now resulted in the isolation of a new bis-diterpenoid alkaloid, which we named piepunine (Fig. 1). This represents the first example of an atisine -denudatine-type bis-diterpenoid alkaloid. The isolation and structure determination of the new bis-diterpenoid alkaloid is described herein, and a plausible biogenetic pathway is proposed as well.

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“…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.…”

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