Two new annonaceous acetogenins from seeds of Annona squamosa / 中草药

ABSTRACT

Objective: To study the chemical constituents from the seeds of Annona squamosa. Methods: Modern methods such as silica gel column and preparation liquid phase were used to isolate and purify the components of annonaceous acetogenins from the seeds of A. squamosa. The structures of the compounds were identified by their physico-chemical properties, UV, NMR and mass spectrometry data. Results: Ten adjacent bistetrahydrofuran annonaceous acetogenins were isolated from CO2 supercritical extract of the seeds from A. squamosa. They were 3-((13R)-13-((2R,2'R,5R,5'R)-5'-((1S)-1,5-dihydroxynonyl) octahydro-[2,2'-bifuran]-5-yl)-13-hydroxytridecyl)-5-methylfuran-2 (5H)-one (1), 3-((2R,9R)-2,9-dihydroxy-9-((2R,2'R,5R,5'R)-5'-((S)-1-hydroxypentadecyl) octahydro-[2,2'-bifuran]-5-yl) nonyl)-5-methylfuran-2 (5H)-one (2), 6-hydroxy-desacetyl-uvaricin (3), 6-hydroxy-4-deoxy-squamotacin (4), bullanin (5), 10-hydroxy-asimicin (6), folianin A (7), annosquacin I (8), annosquacin C (9), and squamocin I (10). Conclusion: Compounds 1 and 2 are two new compounds named as 28-hydroxy-squamocin L (1) and 4-hydroxy-squamocin Y (2), respectively. Compounds 3-7 are isolated from A. squamosa for the first time.