Mesaconitine

Abstract

The title compound, (1α,3α,6α,14α,15α,16β)-3,8,13,14,15-penta­hydr­oxy-1,6,16-trimeth­oxy-4-methoxy­methyl-20-methyl­acon­itan-8,14-diyl 8-acetate 14-benzoate, C33H45NO11, a C19 diterpenoid alkaloid, obtained from the roots of Aconitum kusnezoffii, has been crystallographically characterized in this study. Rings A, B and E have chair conformations, rings C and F display envelope conformations, and ring D adopts a boat conformation. There are inter- and intra­molecular O—H⋯O hydrogen bonds, the latter resulting in the formation of a non-planar seven-membered ring. The inter­molecular inter­actions link the mol­ecules into a two-dimensional network.

Crystal structure of sepaconitine, a C19-diterpenoid alkaloid from the roots ofAconitum sinomontanumNakai

“…For the synthesis of the title compound, see: Wei et al (1996). The absolute configuration of the title compound has been assigned to be the same as that reported for typical natural C 19 -diterpenoid alkaloids, see: Wang et al (2007); He et al (2008). The six-ring rigid-frame structure of the title compound is identical to that of lappaconitine and mesaconitine (Wang et al, 2007;He et al, 2008 Symmetry codes: (i) x þ 1 2 ; Ày þ 1 2 ; Àz þ 2; (ii) Àx þ 3 2 ; Ày; z þ 1 2 .…”

14-Benzoylmesaconine hydrochloride methanol monosolvate

“…For background to the strong toxicity of Aconitum alkaloids, see: Zhang et al (2002). For ring numbering and ring conformations of the title compound, see: He et al (2008).…”

“…The bond lengths and angles are in good agreement with expected values. For ring naming ( Figure 2) and ring conformations please refer to He et al (2008). The cation of the title compound has an aconitine carbon skeleton with four six-membered rings and two five-membered rings.…”

“…Methyl and hydroxyl hydrogen atoms were allowed to rotate at a fixed angle around the C-O bond to best fit the experimental electron density. View of the structure of the title compound with naming of the rings (He et al, 2008), showing 50% probability displacement ellipsoids. Refinement.…”

3-Deoxyaconitine from the root ofAconitum CarmichaeliDebx.

“…For the chemical structure of the title compound established from NMR and MS data, see: Pelletier et al (1984). For the structures of related C 19 -diterpenoid alkaloids, see : Tashkhodjaev & Sultankhodjaev (2009) ;He et al (2008 Table 1 Hydrogen-bond geometry (Å , ). Data collection: DIFRAC (Flack et al, 1992); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999 is shown in Fig.…”