The first limonoid peroxide in the Meliaceae family: walsuronoid A from Walsura robusta.
Walsuronoid A (1), a limonoid featuring an unprecedented 3,4-peroxide-bridged A-seco skeleton, together with walsuronoids B (2) and C (3) possessing a rare 18(13-->14)-abeo-limonoid skeleton, was isolated from Walsura robusta. The structures were elucidated by spectroscopic analysis and chemical correlation, and that of 1 was confirmed by single-crystal X-ray diffraction. Biosynthetic pathway of 2 and 3 was proposed and was chemically mimicked. Compounds 1 and 2 showed weak antimalarial activity.
Yin
Sheng
S
State Key Laboratory of Drug Research, Institute of Materia Medica, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, 555 Zuchongzhi Road, Zhangjiang Hi-Tech Park, Shanghai 201203, People's Republic of China.
Wang
Xiao-Ning
XN
Fan
Cheng-Qi
CQ
Liao
Shang-Gao
SG
Yue
Jian-Min
JM
D000818:Animals; D000962:Antimalarials / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018360:Crystallography, X-Ray; D036701:Limonins / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D029582:Meliaceae / Q000737:chemistry*; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D008968:Molecular Conformation; D021261:Parasitic Sensitivity Tests; D010545:Peroxides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects; D012015:Reference Standards; D012680:Sensitivity and Specificity; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000962:Antimalarials; D001952:Bridged-Ring Compounds; D036701:Limonins; D010545:Peroxides; C521917:walsuronoid A; C521919:walsuronoid B; C521920:walsuronoid C