Three new tetranortriterpenoids from neem seed oil.
Three new tetranortriterpenoids, 1alpha,2alpha-epoxy-17beta-hydroxyazadiradione (1), 1alpha,2alpha-epoxynimolicinol (2), and 7-deacetylnimolicinol (3), have been isolated from a methanol extract of neem oil (Azadirachta indica, seed oil) along with the known compounds epoxyazadiradione, 17beta-hydroxyazadiradione, gedunin, nimbin, and nimolicinol (4). Spectral studies and chemical transformations were used to establish the structure of compounds 1-3. The characterization of the epoxides 1 and 2 in neem oil is of biogenetic significance, as they may be considered as intermediates between A-ring enones and 1,3-diols among the A. indica tetranortriterpenoids.
Department of Chemistry, Indian Institute of Technology, Powai, Mumbai 400 076, India.
Gurulingappa
G
Hallur
Apoorba
A
Sivramakrishnan
Sujata V
SV
Bhat
D000107:Acetylation; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D005989:Glycerides / Q000737:chemistry*; D007194:India; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification*
C466380:1alpha,2alpha-epoxy-17beta-hydroxyazadiradione; C466382:1alpha,2alpha-epoxynimolicinol; C466381:7-deacetylnimolicinol; D005989:Glycerides; D013729:Terpenes; D014315:Triterpenes; C002443:neem oil