Isolation, X-ray crystallography, and computational studies of calydaphninone, a new alkaloid from Daphniphyllum calycillum

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1355-1358

  Di, Ying Tong ^a,c   He, Hong Ping ^a   Wang, Yun Song ^d   Li, Ang Bo ^a   Lu, Yang ^b   Gong, Jian Bo ^b   Fang, Xin ^a   Kong, Ning Chuan ^a   Li, Shun N ^a   Zhu, Hua Jie ^a   Hao, Xiao Jiang ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b INSTITUTE OF MATERIA MEDICA   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^d YUNNAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTINEOPLASTIC AGENT; CALYDAPHNINONE; FUSED HETEROCYCLIC RINGS; PLANT EXTRACT; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN; ISOLATION AND PURIFICATION; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF; PLANT STEM; SAXIFRAGACEAE; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT LEAVES; PLANT STEMS; SAXIFRAGACEAE;

EID: 34147158803     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070218r     Document Type: Article

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27. + 386.2331, found 386.2333.
28. Crystallographic data for calydaphninone (1) have been deposited at the Cambridge Crystallographic Data center (deposition no. CCDC-618286). Copies of data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving. html.
29. 5; for more details see Supporting Information.
30. Configuration of C-11 or C-12 is relative to a reference plane, which is determined by C-5, C-9, and C-10.
31. 5 (3:1). For more details, see Supporting Information.
32. Rapid interconversion between confromers at room temperature was also observed in other Daphniphyllum alkaloids: (a) Monta, H.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 3553-3563.
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34. (a) Gaussian 03 was used to search for the stable conformations of 1 and transition state structures. The crystal structure of 1 was used in the stable conformations search of 1. B3LYP/6-31G(d) was used to optimize all conformations and transition states. Only one negative eigenvalue and one imaginary frequency were obtained for each TS in computations. The frequency calculations and eigenvalues for transition state structures were passed the analyses. The free energy magnitudes were used throughout the theoretical studies.
35. (b) Frisch, M. J. et al. Gaussian 03, revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003. Full references for Gaussian programs are provided in Supporting Information.
36. The calculated bond lengthes, bond angels, and dihedral angels of CTC are in good agreement with the crystallography results. The average rms differences are 0.012 Å, 0.97°, 2.7°, respectively. For more details, see Supporting Information.
37. The ratio of two set of peaks remained almost unchanged after heating at 333 K for 1 h.
38. DFT calculations at the B3LYP/6-31G(d) level were carried out on a model of the HCl salt of calydaphninone (1). Three stable conformers were found. Among them, BHC-HCl is the stablest conformer. The other two, CC-HCl and CTC-HCl, are 2.36 and 1.65 kcal/mol higher in free energy than the stablest conformer CC, respectively. For details, see Supporting Information.