A spontaneous conversion of gagamine, a steroidal alkaloid, into lineolon via internal acyl migrations and the following elimination

Bulletin of the Korean Chemical Society

Volumn 23, Issue 1, 2002, Pages 9-10

  Lee, Dong Ung ^a  

^a Dongguk University   (South Korea)

Author keywords

Acyl migration; Gagamine; Lineolon; Molecular modelling study

Indexed keywords

ALKALOID DERIVATIVE; CARBON; CARBONYL DERIVATIVE; GAGAMINE; ISOLINEOLON; LINEOLON; PREGNANE DERIVATIVE; SOLVENT; STEROID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; CRYSTALLIZATION; CYNANCHUM CAUDATUM; EXTRACTION; HYDROGEN BOND; HYDROLYSIS; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; MEDICINAL PLANT; MELTING POINT; MOLECULAR MODEL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037138259     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: 10.5012/bkcs.2002.23.1.009     Document Type: Article

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13. The mother liquid obtained from recrystallization of gagamine produced nicotinic acid, which was identified by the comparison of TLC and mixed melting point measurement (mp. 232-235 °C) with an authentic sample.
14. All calculations were run using the SYBYL 6.5 molecular modelling package (Tripos Associates, St. Louis, MO). Gasteiger-Hueckel charges: ε= 1, Energy: 38.47 kcal/mole, Distance: C52-067 3.68. Energy increases only by 4.2 kcal/mole.
15. 3): δ 13.0 (18-C), 19.0 (19-C), 23.3 (11-C), 27.2 (15-C), 30.9 (2-C), 31.9 (21-C), 33.2 (16-C), 34.3 (7-C), 37.0 (10-C), 38.7 (1-C), 42.0 (4-C), 44.1 (9-C), 55.9 (13-C), 60.7 (17-C), 68.3 (12-C), 71.9 (3-C), 74.6 (8-C), 85.7 (14-C), 117.5 (6-C), 141.2 (5-C), 214.8 (20-C).