Limonoids from the leaves and stems of Toona ciliata.
Three new norlimonoids, toonaciliatins A (1), F (6), and G (7), four new limonoids, toonaciliatins B-E (2-5), and five known compounds, 5alpha,6beta,8alpha-trihydroxy-28-norisotoonafolin (8), toonaciliatins H (9) and I (10), febrifugin (11), and khayasin T (12), were isolated from the leaves and stems of Toona ciliata. Compounds 1-3 have an unusual 1-en-3-one system with a 1,11-oxygen bridge, limonoids 11 and 12 have a mexicanolide-type structural frame, and others are typical A,B-seco- (4, 5, 9, and 10) or B-seco-29-nor- (3, 6, 7, and 8) limonoids. Toonaciliatins H (9) and I (10) were obtained for the first time as natural products. The structures were established by extensive spectroscopic methods, particularly 1D and 2D NMR techniques.
Liao
Shang-Gao
SG
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, People's Republic of China.
Yang
Sheng-Ping
SP
Yuan
Tao
T
Zhang
Chuan-Rui
CR
Chen
Hua-Dong
HD
Wu
Yan
Y
Xu
You-Kai
YK
Yue
Jian-Min
JM
D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification*; D036701:Limonins / Q000737:chemistry / Q000302:isolation & purification*; D029582:Meliaceae / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry
D004365:Drugs, Chinese Herbal; D036701:Limonins; C522943:toonaciliatin A; C522944:toonaciliatin F; C522945:toonaciliatin G