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X-ray and DFT Study of Glaucocalyxin A Compound with Cytotoxic Activity
Fu-dong Wang,Tao Wang,An-an Wu,Lan Ding,Han-qing Wang*
Author NameAffiliationE-mail
Fu-dong Wang State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, ChinaGraduate School of the Chinese Academy of Sciences, Beijing 100039, China  
Tao Wang Collage of Physics and Mechanical Electrical Engineering, Xiamen University, Xiamen 361005, China Department of Chemistry and Chemical Engineering, Heze University, Heze 274015, China  
An-an Wu State Key Laboratory of Physical Chemistry of Solid Surfaces, Collage of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China sebastien.weber@irsamc.ups-tlse.fr 
Lan Ding College of Life Science, Northwest Normal University, Lanzhou 730070, China  
Han-qing Wang* State Key Laboratory of Solid Lubrication, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China whqwt@yahoo.com.cn 
Abstract:
The title compound glaucocalyxin A (1) (7α,14β-dihydroxy-ent-kaur-16-en-3,15-dione) isolated from the leaves of isodon excisoides was characterized by IR, 1H NMR, 13C NMR,1H-1H COSY, HMQC, HMBC, and EIMS, and its crystal structure was determined by singlecrystal X-ray diffraction. The X-ray crystal structure revealed that the molecular backbone of the chosen crystal is a tetracyclic system, including three six-membered rings and a five-membered ring, and the three six-membered rings are in a chair-like conformation. The five-membered ring adopts a twisted envelope-like conformation, and its geometrical parameters were compared with theoretical calculations at the B3LYP and HF level of theory. The molecules form extensive networks through the intra- and intermolecular hydrogen bonds.The experimental NMR data were interpreted with the aid of magnetic shielding constant calculations, by means of the GIAO (gauge-lncluding atomic orbitals) method. Calculated and experimental results were compared with a satisfactory level of agreement. Molecular electrostatic potential map was used in an attempt to identify key features of the diterpenoid glaucocalyxin A that is necessary for its activity. Calculations of molecular electrostatic potential and stabilization energies suggest that the protonation of glaucocalyxin A will be able to occur on carbonyl oxygen atoms.
Key words:  Isodon excisoides, Glaucocalyxin A, X-ray structure, Density functional theory
FundProject:
X-ray and DFT Study of Glaucocalyxin A Compound with Cytotoxic Activity
王福东,汪涛,吴安安,丁兰,汪汉卿*
摘要:
采用单晶X射线衍射技术对化合物的晶体结构进行了研究. 研究结果表明,Glaucocalyxin A分子含3个六元环和1个五元环,其中六元环均为椅式构象,五元环为扭曲信封式构象. Glaucocalyxin A晶体结构属正交晶系. 采用密度函数理论和Hartree-Fock方法对该化合物晶体的键长、键角和两面角进行计算,并与X衍射测定值进行比较,结果表明理论值与实验值符合相当好. 应用规范不变原子轨道,分别在不同水平上,计算了Glaucocalyxin A的1H和13C NMR化学位移,并对理论计算值的误差
关键词:  拟缺香茶菜,Glaucocalyxin A,X单晶衍射结构,密度泛函理论
DOI:10.1088/1674-0068/22/03/275-284
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