Squamostatin-A: Unprecedented bis-tetrahydrofuran acetogenin from Annona squamosa

Acetogenins from Annonaceae

“…Densicomacin-l = 13, 14-erythro-Densicomacin Densicomacin-2 = 13, 14-threo-Densicomacin = Gigantetrocin Annona squamosa (seeds) (13,14,15); Annona cherimolia (seeds) (16), (roots) (17) erythro trans threo OH 34 28 19 01, 12 16 OH OH OH threo trans 37 Squamostatin-A was first described without assignment of relative configuration (15) and with 13C nmr data which apparently corresponded to the configuration threo-threo-cis-erythro (12,16) while almunequin was assigned configuration threo-threo-trans-erythro (16). In a subsequent paper dealing with squamostatin-A the Japanese authors presented 13C nmr data for squamostatin A identical with those of almunequin and proposed the configuration trans-threo-threo-transerythro (20).…”

“…[a]D = + 13S (c = 0.14, CHCI 3 ) (13,14) IR (13,15,16); UV (13,15) lH nmr (10), (500 MHz) (13,15), (400 MHz) (16); 13C nmr (10), (125 MHz) (13,14,15), (100 MHz) (16) F ABms (13,15,16), F ABms/ms (15), elms (10,15,16), Elms (10,11) HRms (13), HRElms (13,14) tetraacetate: 1 H nmr (10), (500 MHz) (13,14,15) tetra-TMSi derivative: Elms (11) mesitoate: 1 H nmr (C6D6' 500 MHz) (13,14) tetra-( + )-MTPA ester: 1 H nmr (10), (500 MHz) (15) (25) UV (25) lH nmr (500 MHz) (25); 13C nmr (125 MHz) (25) F ABms (25), HRF ABms (25) hexaacetate: 1 H nmr (500 MHz) (25), 13C nmr (125 MHz) (25) TMSi derivative: Elms (25), HRElms (25) …”

“…C37H660S; M = 638 mp = 87-89 °C (15), mp = 105-106 DC (13,14) [a]D = + 11 0 (c = OA, MeOH) (15), [aJo = + 25° (c = 0.38, MeOH) (16),…”

Saturated long-chain hydrocarbons fromAnnona squamosaL. bark

“…The plant has been reported to possess insecticidal and cytotoxic activities (Fujimoto et al, 1998). The hydrocarbons are responsible for this cytotoxic activity (Choo, Chan, Sam, Hitotsuyanagi, & Takeya, 2001).…”

Annona squamosa

“…Squamolone (a diazepine) (Yang and Chen 1972) and aporphine alkaloids anonaine, roemerine, norcorydine, corydine, norisocorydine, isocorydine and glaucine were isolated from A. squamosa (Bhakuni et al 1972). Also cytotoxic bis-tetrahydrofuran squamocin and squamostatin-A were isolated from A. squamosa (Fujimoto et al 1988(Fujimoto et al , 1990.…”