Antifeedant rings B and D opened limonoids from Khaya senegalensis.
Three new rings B and D opened limonoids, two mexicanolides named khayanone (1) and 2-hydroxyseneganolide (2) and one rearranged phragmalin limonoid of 1-O-acetylkhayanolide A (3), were isolated together with six known B,D-seco compounds from the acetone extract of the stem bark of Khaya senegalensis. Structures of new compounds were elucidated by spectroscopic means, and the absolute stereochemistry of 1 was established by CD study of the dibenzoate derivative. The insect antifeedant and antiviral activities of the new compounds were also determined.
Nakatani
M
M
Department of Chemistry and Bioscience, Faculty of Science, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan. nakat@mail.sci.kagoshima-u.ac.jp
Abdelgaleil
S A
SA
Kurawaki
J
J
Okamura
H
H
Iwagawa
T
T
Doe
M
M
D000818:Animals; D019380:Anti-HIV Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002855:Chromatography, Thin Layer; D004305:Dose-Response Relationship, Drug; D004534:Egypt; D005247:Feeding Behavior / Q000187:drug effects; D015497:HIV-1 / Q000187:drug effects; D007814:Larva / Q000378:metabolism; D036701:Limonins; D009682:Magnetic Resonance Spectroscopy; D029582:Meliaceae / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D018411:Spodoptera / Q000378:metabolism; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
C439995:1-O-acetylkhayanolide A; C439994:2-hydroxyseneganolide; D019380:Anti-HIV Agents; D036701:Limonins; D010936:Plant Extracts; D014315:Triterpenes; C439993:khayanone