Crystal structure of tuguaconitine, a diterpene alkaloid from Aconitum sibiricum.
The three-dimensional structure of a natural product, tuguaconitine (C23H35NO7) from Aconitumrn sibiricum was determined by single crystal X-ray diffraction analysis. The compound was recrystallized from a methanol solution into orthorhombic crystal system, with a = 18.093(4), b = 12.075(11), c = 9.824(4) A, Dm = 1.35, Dx= 1.354 g/cm3, space group P2(1)2(1)2(1), and Z=4. The structure was solved by direct method and refined by least-squares procedure to the final R value of 0.046 for 1495 observed reflections with I > or = 2sigma(I). Aconitines are diterpene alkaloid composed of six rings. In the molecule, two 6-membered rings have stable chair conformation, but other two 6-membered rings have unstable boat conformation because of their bonding strain and hydrogen bonds. Based on the three-dimensional structure of tuguaconitine, we suggest another 2D-diagram for the compound which is far better in imagination of the spatial shape of the molecule than the ordinary one.
Kang
Chang Kyun
CK
College of Pharmacy, Chungbuk National University, Cheongju 361-763, Korea.
Lee
Soo Jae
SJ
Kim
Yang Bae
YB
Lee
Hyeong Kyu
HK
Jeong
Eun Ju
EJ
Park
Il Yeong
IY
D000157:Aconitine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000302:isolation & purification; D031841:Aconitum / Q000737:chemistry*; D002725:Chloroform; D003460:Crystallization; D006586:Hexanes; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D012997:Solvents; D014961:X-Ray Diffraction
D006586:Hexanes; D012997:Solvents; C528440:tuguaconitine; D002725:Chloroform; D000157:Aconitine