Seven new Lycopodium alkaloids, lycoposerramines-C, -D, -E, -P, -Q, -S, and -U, from Lycopodium serratum Thunb.

Tetrahedron Letters

Volumn 43, Issue 46, 2002, Pages 8307-8311

  Takayama, Hiromitsu ^a   Katakawa, Kazuaki ^a   Kitajima, Mariko ^a   Yamaguchi, Kentaro ^a   Aimi, Norio ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

Alkaloids; Lycopodium; NMR; Structure elucidation; X ray crystal structures

Indexed keywords

ALCOHOL DERIVATIVE; ALKALOID DERIVATIVE; LYCOPODIUM SERRATUM EXTRACT; LYCOPOSERRAMINE C; LYCOPOSERRAMINE D; LYCOPOSERRAMINE E; LYCOPOSERRAMINE P; LYCOPOSERRAMINE Q; LYCOPOSERRAMINE S; LYCOPOSERRAMINE U; PLANT EXTRACT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG ISOLATION; LYCOPODIACEAE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

BRYOPHYTA; HUPERZIA SERRATA SERRATA; LYCOPODIUM;

EID: 0037064495     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02026-9     Document Type: Article

References (38)

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30. 3) δ: 3.86 (1H, t, J=2.4 Hz, H-8), 3.24 (1H, brd, J=14.3 Hz, H-17), 3.03 (1H, ddd, J=3.8, 9.5, 13.3 Hz, H-9), 2.95 (1H, ddd, J=3.7, 13.7, 13.7 Hz, H-1), 2.88 (2H, m, H-1, 9), 2.70 (1H, ddd, J=2.4, 8.2, 10.5 Hz, H-7), 2.66 (1H, m, H-17), 2.63 (1H, m, H-6), 2.53 (1H, dd, J=13.1, 18.0 Hz, H-14), 2.43 (1H, dd, J=9.3, 13.9 Hz, H-11), 2.20 (4H, m, H-10, 11, 14, 15), 2.03 (1H, dd, J=8.2, 18.2 Hz, H-6), 1.98 (2H, m, H-3, 3), 1.80 (2H, m, H-2, 10), 1.34 (1H, m, H-2), 1.06 (3H, d, J=6.4 Hz, H-16).
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34. 6) δ: 4.37 (1H, m, H-2), 3.57 (1H, dd, J=5.6, 13.9 Hz, H-1), 3.18 (1H, ddd, J=3.2, 14.3, 14.3 Hz, H-9), 2.70 (1H, dd, J=5.2, 14.3 Hz, H-9), 2.54 (1H, m, H-3), 2.37 (1H, dd, J=11.7, 17.9 Hz, H-6), 2.27 (2H, m, H-1, 11), 2.10 (1H, m, H-15), 2.04 (3H, m, H-6, 10, 14), 1.92 (3H, m, H-3, 4, 7), 1.53 (2H, m, H-8, 11), 1.38 (2H, m, H-8, 10), 1.30 (1H, m, H-14), 0.89 (3H, d, J=6.4 Hz, H-16).
35. 3) δ: 5.57 (1H, d, J=3.4 Hz, H-14), 3.96 (1H, q, J=4.9 Hz, H-5), 3.09 (1H, brd, J=12.8 Hz, H-1), 2.97 (3H, m, H-1, 9, 9), 2.23 (1H, m, H-15), 2.13 (1H, m, H-7), 1.92 (2H, m, H-3, 10), 1.85 (2H, m, H-4, 11), 1.75 (3H, m, H-2, 6, 6), 1.69 (1H, m, H-2), 1.57 (1H, ddd, J=4.3, 12.5, 12.5 Hz, H-11), 1.51 (2H, m, H-8, 10), 1.35 (1H, q, J=12.7 Hz, H-3), 1.26 (1H, m, H-8), 0.98 (3H, d, J=7.0 Hz, H-16).
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38. 3), 2.21 (1H, m, H-9), 2.01 (1H, ddd, J=1.9, 4.8, 13.4 Hz, H-1), 1.94 (1H, m, H-7), 1.87 (1H, m, H-15), 1.75 (2H, m, H-3, 6), 1.69 (2H, m, H-2, 14), 1.57 (1H, m, H-4), 1.49 (1H, m, H-11), 1.48 (1H, m, H-10), 1.43 (2H, m, H-8, 11), 1.34 (3H, m, H-3, 6, 10), 1.20 (1H, m, H-2), 1.05 (1H, ddd, J=3.2, 13.0, 13.0 Hz, H-8), 1.00 (1H, ddd, J=2.7, 12.2, 12.2 Hz, H-14), 0.88 (3H, d, J=6.4 Hz, H-16).