520
Journal of Natural Products, 1999, Vol. 62, No. 3
Invited Review
Table 4. (Continued)
Mono-THF Acetogenins (Continued)
38. glabranin23 (C37H66O7, MW622)
Position12151619202324
1H (δ)3.823.823.403.403.405.355.38
13C (δ)79.3181.7274.4274.2374.59128.60130.18
Amorphous powder. MS: EIMS m/z 493, 475, 379, 361, 309, 295, 293, 291, 269, 267, 251, 249, 225. NMR:1H NMR (400 MHz, CDCl3),13C NMR (100 MHz, CDCl3). Derivatives: peracetate (1H NMR). Source: Annona glabra, seeds. goniodonin31 (reported as an epimeric pair) (C35H64O8, MW612)
goniodon
Position 10 15 16 19 20 34
1 H ( \delta ) 3.63 m 3.41 m 3.78 m 3.78 m 3.41 m ---
13 C ( \delta ) 71.5 74.4 82.5 82.7 74.3 105.0
Position 10 15 16 19 20 34
1 H ( \delta ) 3.63 m 3.41 m 3.78 m 3.78 m 3.41 m ---
13 C ( \delta ) 71.5 74.4 82.5 82.7 74.3 105.3
34-epi-goniodon
White amorphous powder. Mp: 78–80°C. [α]D: +3.4° (c O.17, MeOH). IR (νmax, film, cm⁻¹): 3514, 2921, 2852, 1734, 1467. MS: EIMS m/z 595, 577, 559, 541, 523, 413, 395, 377, 359, 341, 343, 325, 307, 289, 271, 257, 239, 221, 157, 139, 121. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: phenylhydrazone (¹H NMR), per-MTPA esters (¹H NMR), TMS (EIMS). Biological activities (μg/mL): HCT-81C50 <10. Source: Goniothalamus donnaiensis, roots. cis-goniodonin³¹ (reported as an epimeric pair) (C₃₅H₆1O₂. MW612)
cis-goniodonin
Position 10 15 16 19 20 34
1 H (δ) 3.63 m 3.41 m 3.78 m 3.78 m 3.41 m ---
13 C (δ) 71.4 74.5 82.6 82.6 74.2 105.0
Position 10 15 16 19 20 34
1 H (δ) 3.63 m 3.41 m 3.78 m 3.78 m 3.41 m ---
13 C (δ) 71.4 74.5 82.6 82.6 74.2 105.3
34-epi-cis-goniodon
White amorphous powder. Mp: 80–82°C. [α]D: +3.8° (c O.I.Q, MeOH). IR (νmax, film, cm⁻¹): 3413, 2920, 2851, 1735, 1465. MS: EIMS m/z 595, 577, 559, 541, 523, 413, 395, 377, 359, 341, 343, 325, 307, 289, 271, 257, 239, 221, 157, 139, 121. NMR: ¹H NMR (500MHz, CDCl₃), ¹³C NMR (125MHz, CDCl₃). Derivatives: phenylhydrazone (¹H NMR), per-MTPA esters (¹H NMR), TMS (EIMS). Biological activities (μg/mL): HCT-8IC₅₀ <10. Source: Goniothalamus donnaiensis, roots. isomurisolenin¹¹⁴ (reported as cis and trans mixture) (C₃₅H₆₂O₆, MW578)
(2,4-cis)-isomurisolenin
(2,4-trans)-isomurisolenin
Position 11 12 15 16 19 20
1H (δ) 5.36 5.38 3.40 m 3.80 m 3.80 m 3.40 m
13C (δ) 130.7 128.9 74.0 82.6 82.5 74.0
Position 11 12 15 16 19 20
1H (δ) 5.36 5.38 3.40 m 3.80 m 3.80 m 3.40 m
13C (δ) 130.7 128.9 74.0 82.6 82.5 74.0
White waxy solid. [α]D: +32.9° (c 0.31, CHCl_{3}). IR (νmax, film, cm^{-1}): 3500, 2910, 2860, 1760, 1710, 1460, 1250, 1050, 800. MS: EIMS m/z 391, 379, 373, 361, 291, 265, 211, 141. NMR: ^1H NMR (400 MHz, CDCl_{3}), ^13C NMR (100 MHz, CDCl_{3}). Biological activities (μg/mL): Hep. 2, 2, 2, 15 ED_{50} 1.4 × 10^{-1}, Hep G2 ED_{50} 4.7 × 10^{-2}, KB ED_{50} 1, CCM2 ED_{50} 8.5 × 10^{-2}. Source: Annona reticulata, seeds.