Invited Review
Journal of Natural Products, 1999, Vol. 62, No. 3
533
Table 4. (Continued)
104. 10-hydroxytrilobacin124(C37H66O8, MW638)
Position10151619202324
1H (δ)3.59 m3.39 m3.83 m3.97 m4.05 m3.83 m3.39 m
13C (δ)71.874.583.281.680.982.673.9
Colorless oil. [α]D: +8.3° (c 0.36, CHCl_{3}). IR (νmax, film, cm^{-1}): 3365, 2928, 2856, 1752, 1590, 1456, 1420, 1120, 1036. NMR: 1H NMR (500 MHz, CDCl_{3}), 13C NMR (125 MHz, CDCl_{3}). Derivatives: peracetate (^{1}H NMR), per-MTPA esters (^{1}H NMR), acetonide (^{1}H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC50 2.6 × 10^{-1}, A-549 ED50 1.0 × 10^{-8}, MCF-7 ED50 1.9 × 10^{-8}, HT-29 ED50 1.4, A-498 ED50 1.0 × 10^{-2}, PC-3 ED50 3.8 × 10^{-1}, PAC-2 ED50 2.0 × 10^{-1}. Source: Asimina triloba, stem bark.
squamolinone125 (reported as a cis and trans mixture) (C35H62O7, MW594)
(2,4-cis)-squamolinone Position 15 16 19 20 23 24
1H (δ) 3.40 m 3.86 m 3.93 m 3.86 m 3.93 m 3.86 m
13C (δ) 74.09 83.18 82.39 82.18 82.83 71.56
(2,4-trans)-squamolinone
Position 15 16 19 20 23 24
1H (δ) 3.40 m 3.86 m 3.93 m 3.86 m 3.93 m 3.86 m
13C (δ) 74.09 83.18 82.39 82.18 82.83 71.56
White amorphous powder. [α]D: +21.4° (c O073, CH₂Cl₂). UV (λmax, MeOH, nm): 203 (log ε 285). IR (νmax, film, cm⁻¹): 3426, 2920, 2850, 1767. MS: EIMS m/z 363, 345, 311, 283. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀ 7.4 × 10⁻², A-549ED₅₀ 1.9, MCF-7 ED₅₀ 1.8, HT-29ED₅₀ 1.7, A-498ED₅₀ 1.8, PC-3ED₅₀ 2.6, PACA-2ED₅₀ 1.1. Source: Annona squamosa, stem bark. 9-oxoasimicinone125 (reported as a cis and trans mixture) (C37H64O8, MW636)
(2,4-cis)-9-oxoasimicinone
Position 9 15 16 19 20 23 24
1H (δ) - 3.39 m 3.83 m 3.86 m 3.86 m 3.83 m 3.39 m
13C (δ) 211.05 74.05 83.11 81.80 81.77 83.16 73.93
(2,4-trans)-9-oxoasimicinone
Position 9 15 16 19 20 23 24
1H (δ) 3.39 m 3.83 m 3.86 m 3.86 m 3.83 m 3.39 m
13C (δ) 211.02 74.05 83.11 81.80 81.77 83.16 73.93
White amorphous powder. [α]D: +19.7° (c Q10, CHCl3). UV (λmax, MeOH, nm): 203 (log ε 3.55). IR (νmax, film, cm-1): 3390, 2921, 2851, 1770, 1705. MS: EIMS m/z 377, 359, 341, 325, 307, 289, 225, 207. NMR: 1H NMR (500MHz, CDCl3), 13C NMR (125MHz, CDCl3). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC50 6.7 × 10-1, A-549 ED50 5.7 × 10-3, MCF-7 ED50 2.6 × 10-1, HT-29 ED50 4.0 × 10-3, A-498 ED50 4.6 × 10-1, PC-3 ED50 1.1, PAC-2 ED50 1.2. Source: Annona squamosa, stem bark.
bullacin125 (C37H66O7, MW622)
Position6151619202324
1H (δ)3.62 m3.39 m3.84 m3.88 m3.88 m3.84 m3.39 m
13C (δ)71.3773.8082.8681.6581.6582.8673.80
White amorphous powder. [α]D: +43.8° (c OO3, CH2Cl2). UV (λmax, MeOH, nm): 211 (log ε 3.79). IR (νmax, film, cm-1): 3418, 2925, 2853, 1756 MS: EIMS m/z 433, 415, 397, 363, 345, 327, 311, 293, 275, 169, 151. NMR:1H NMR (500MHz, CDCl3),13C NMR (125 MHz, CDCl3). Derivatives: peracetate (1H NMR), per-MTPA esters (1H NMR), formal acetal (1H NMR), TMS (EIMS). Biological activities (μg/mL): BST LC50 1.9 × 10-2, A-549 ED50 9.0 × 10-7, MCF-7 ED50 2.5 × 10-7, HT-29 ED50 4.5 × 10-3, A-498 ED50 >1, PC-3 ED50 >1, PAC-2 ED50 4.1 × 10-1. Source: Annona squamosa, stem bark.