New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata.
Bioactivity-guided fractionation led to the isolation of two new Annonaceous acetogenins, annocatacin A ( 1). and annocatacin B ( 2). from the seeds and the leaves, respectively, of Annona muricata. Compounds 1 and 2 are the first examples where the adjacent bis-tetrahydrofuran ring system is located at C-15. The new structures were elucidated and characterized by spectral and chemical methods. Both Annonaceous acetogenins 1 and 2 showed significant in vitro cytotoxicity toward the human hepatoma cell lines, Hep G2 and 2,2,15, and were compared with the known adjacent bis-tetrahydrofuran acetogenins, neoannonin ( 3). desacetyluvaricin ( 4). bullatacin ( 5). asimicin ( 6). annoglaucin ( 7). squamocin ( 8). and rollimusin ( 9).
Chang
Fang-Rong
FR
Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan, ROC.
Liaw
Chih-Chuang
CC
Lin
Chih-Yuan
CY
Chou
Chi-Jung
CJ
Chiu
Hui-Fen
HF
Wu
Yang-Chang
YC
D031041:Annona; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000494:pharmacology*; D006528:Carcinoma, Hepatocellular / Q000188:drug therapy / Q000473:pathology; D005663:Furans / Q000494:pharmacology*; D006801:Humans; D008113:Liver Neoplasms / Q000188:drug therapy / Q000473:pathology; D009682:Magnetic Resonance Spectroscopy; D008517:Phytotherapy; D018515:Plant Leaves; D028321:Plant Preparations / Q000737:chemistry / Q000494:pharmacology*; D012639:Seeds; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured / Q000187:drug effects
D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D028321:Plant Preparations; C474333:annocatacin A; C474332:annocatacin B