Degraded cyanogenic glucosides from Sambucus nigra

Author:

DellaGreca Marina,Fiorentino Antonio,Monaco Pietro,Previtera Lucio,Simonet Ana M

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference8 articles.

1. DellaGreca, M.; Fiorentino, A.; Monaco, P.; Previtera, L.; Simonet, A. M. Nat. Prod. Letters 2000, 14, 175–182.

2. Compound 3: [α]D +15 (c 0.6, CHCl3); EIMS 353 [M]+, 237 [M−C8H6N]+, 221 [M−C8H6NO]+, 118 [C4H6O4]+; UV λmax (EtOH) 221 and 278 (ε 3150 and 2170); IR νmax (CHCl3) 3619, 3508, 1747 cm−1; anal. calcd for C16H19NO8: C, 54.39; N, 3.96; H, 5.42%. Found: C, 54.31; N, 3.99; H, 5.30%.

3. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1972, 95, 512–519.

4. Compound 4: [α]D −21 (c 0.3, CHCl3); EIMS 353 [M]+, 237 [M−C8H6N]+, 221 [M−C8H6NO]+, 118 [C4H6O4]+; UV λmax (EtOH) 225 and 276 (ε 3160 and 2190); IR νmax (CHCl3) 3621, 3510, 1749 cm−1; 1H NMR δ 7.43 (5H, m, H-4–H-8), 5.72 (1H, s, H-2), 5.05 (1H, d, J=2.6 Hz, H-1′), 4.46 (1H, d, J=2.6 Hz, H-2′), 4.57 (1H, dd, J=3.3 and 5.6 Hz, H-5′), 4.08 (1H, dd, J=3.3 and 10.4 Hz, H-6′), 3.81 (1H, dd, J=5.6 and 10.4 Hz, H-6′), 3.65 (3H, s, OMe), 3.84 (3H, s, OMe); anal. calcd for C16H19NO8: C, 54.39; N, 3.96; H, 5.42%. Found: C, 54.33; N, 4.11; H, 5.32%.

5. Compound 5: [α]D −3 (c 0.5, CHCl3); EIMS 353 [M]+, 237 [M−C8H6N]+, 221 [M−C8H6NO]+, 118 [C4H6O4]+; UV λmax (EtOH) 224 and 279 (ε 3130 and 2130); IR νmax (CHCl3) 3618, 3509, 1747 cm−1; 1H NMR δ 7.51 (2H, m, H-4 and H-8), 7.43 (3H, m, H-5–H-7), 6.02 (1H, s, H-2), 5.25 (1H, d, J=4.0 Hz, H-1′), 4.38 (1H, d, J=4.0 Hz, H-2′), 4.52 (1H, dd, J=3.2 and 6.7 Hz, H-5′), 4.09 (1H, dd, J=3.2 and 10.4 Hz, H-6′), 3.93 (1H, dd, J=6.7 and 10.4 Hz, H-6′), 3.68 (3H, s, OMe), 3.84 (3H, s, OMe); anal. calcd for C16H19NO8: C, 54.39; N, 3.96; H, 5.42%. Found: C, 54.27; N, 4.06; H, 5.37%.

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