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Journal of Natural Products, 1999, Vol. 62, No. 3
Invited Review
Table 4. (Continued)
4. 4-deoxyannoreticuin*109 (C35H64O6, MW580) Mono-THF Acetogenins (Continued)
Position915161920
1H (δ)3.58 m3.41 m3.80 m3.80 m3.41 m
13C (δ)71.9074.0882.5382.6474.06
White amorphous powder. [α]D: +6.8° (c QO15, CH₂Cl₂). UV (λmax, MeOH, nm): 218 (log ε 3.61). IR (νmax, film, cm-1): 3423, 2926, 2854, 1755. MS: EIMS m/z 345, 311, 293, 275, 211, 193. NMR: 1H NMR (500MHz, CDCl₃), 13C NMR (125 MHz, CDCl₃). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC50 8.9, A-549 ED50 3.9, MCF-7 ED50 2.2, HT-29 ED50 1.7, A-498 ED50 2.2, PC-3 ED50 2.7, PAC-2 ED50 2.9. Source: Annona squamosa, stem bark. 5. cis-4-deoxyannoreticquin*109 (C35H64O6, MW580)
Position 9 15 16 19 20
1H ( \delta ) 3.59 m 3.42 m 3.82 m 3.82 m 3.42 m
13C ( \delta ) 71.86 74.37 82.67 82.67 74.37
White amorphous powder. [α]D: +6.8° (c QO15, CHCl_{3}). UV (λmax, MeOH, nm): 218 (log ε 3.61). IR (νmax, film, cm^{-1}): 3423, 1916, 2854, 1755. MS: EIMS m/z 345, 311, 293, 275, 211, 193. NMR: 1H NMR (500MHz, CDCl_{3}), 13C NMR (125MHz, CDCl_{3}). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC_{50} 6.8, A-549ED_{50} 2.0, MCF-7 ED_{50} 1.7, HT-29 ED_{50} 1.4, A-498ED_{50} 1.8, PC-3 ED_{50} 2.1, PACA-2 ED_{50} 1.1. Source: Annona squamosa, stem bark. squamoxinone(9) (reported as a cis and trans mixture) (C_{6}-H_{2}-O, MW624).
squamoxinone109 (reported as a cis and trans mixture) (C37H68O7, MW624)
(2,4-cis)-squamoxinone
Position 11 17 18 21 22
1H (δ) 3.59 m 3.41 m 3.80 m 3.80 m 3.41 m
13C (δ) 71.86 74.02 82.63 82.58 73.97
Position 11 17 18 21 22
1H (δ) 3.59 m 3.41 m 3.80 m 3.80 m 3.41 m
13C (δ) 71.86 74.02 82.63 82.58 73.97
(2,4-trans)-squamoxinone
White amorphous powder. [α]D: +13.3° (c OO23, CH2Cl2). UV (λmax, MeOH, nm): 203 (log ε 3.20). IR (νmax, film, cm-1): 3445, 2919, 2850, 1755. MS: EIMS m/z 407, 389, 371, 337, 319, 255. NMR: 1H NMR (500MHz, CDCl 3), 13C NMR (125MHz, CDCl 3). Derivatives: per-MTPA esters (1H NMR). Biological activities (μg/mL): BST LC50 2.7, A-549ED50 1.9, MCF-7 ED50 1.7, HT-29 ED50 1.4, A-498ED50 1.5, PC-3 ED50 2.2, PAC-2 ED50 4.5 × 10-3. Source: Annona squamosa, stem bark. xylomaticinone39 (reported as a cis and trans mixture) (C37H69O7, MW624)
(2,4-cis)-xylomaticinone
Position 10 15 16 19 20
1H (δ) 3.59 m 3.41 m 3.80 m 3.80 m 3.41 m
13C (δ) 71.7 73.97 82.60 82.66 74.04
Position 10 15 16 19 20
1H (δ) 3.59 m 3.41 m 3.80 m 3.80 m 3.41 m
13C (δ) 71.7 73.97 82.60 82.66 74.04
(2,4-trans)-xylomaticinone
White wax. [α]D: +26.2° (c 0.08, CHCl 3). IR (νmax, film, cm-1): 3454, 2916, 2848, 1756, 1716, 1470, 1070.
White wax. [α]D: +26.2 (c 0.08, CHCl₃). IR (νmax, film, cm⁻¹): 3454, 2916, 2848, 1756, 1716, 1470, 1070. MS: EIMS m/z 379, 361, 343, 309, 297, 291, 279, 273, 241, 227, 141. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: per-MTPA esters (¹H NMR). Biological activities (μg/mL): BST LC₅₀, 0.4 × 10⁻¹, A-549ED₅₀, 1.4 × 10⁻², MCF-7 ED₅₀, 7.6 × 10⁻⁴, HT-29ED₅₀, 7.4 × 10⁻⁴, A-498ED₅₀, 1.2 × 10⁻¹, PC-3ED₅₀, 5.7 × 10⁻², PACA-2ED₅₀, 7.4 × 10⁻². Source: Annona squamosa, stem bark.