Cyclopeptide Alkaloids
Cyclopeptide alkaloids are defined as basic compounds embodying an ansa structure, in which a 10- or 12-membered peptide type bridge spans the 1,3 or 1,4 positions of a benzene ring (1). They are widely distributed among plants of the Rhamnaceae family, b
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GOURNELIS 1 , G. G. LASKARIS 2 ,
and R.
VERPOORTE 2
1 Laboratory
of Pharmacognosy, Department of Pharmacy, Aristotelian University of Thessaloniki, Thessaloniki, Greece 2 Division of Pharmacognosy, Leidenl Amsterdam Center for Drug Research, Leiden, The Netherlands
Contents 1. Introduction ..............................................
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2. Classification . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..
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3. Structure Elucidation - Stereochemistry . . . . . . . . . . . . . . . . . . . . . . . . . .. 3.1. NMR Spectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 3.2. UV, IR, and CD Spectroscopy ............................. 3.3. MS ................................................
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4. MS Fragmentation of Cyclopeptide Alkaloids and Related Compounds ..... 4.1. Fragmentation of 4(14)-Frangulanine- and -Integerrine-Type Cyclopeptide Alkaloids .................................. 4.2. Fragmentation of 4(14)-Pandamine-Type Cyclopeptide Alkaloids ..... 4.3. Fragmentation of 5(l3)-Zizyphine-A-Type and 5(14)-AmphibineB-Type Cyclopeptide Alkaloids. . . . . . . . . . . . . . . . . . . . . . . . . . . .. 4.4. Fragmentation of 5(l4)-Scutianine-A-Type Cyclopeptide Alkaloids (Hymenocardine included) ................................ 4.5. Fragmentation of 4(14)-Amphibine-F-Type Cyclopeptide Alkaloids ... 4.6. Fragmentation of 4(13)-Nummularine-C-Type Cyclopeptide Alkaloids . 4.7. Fragmentation of 4(15)-Mucronine-A-Type Cyclopeptide Alkaloids ... 4.8. Fragmentation of Linear Peptide Alkaloids. . . . . . . . . . . . . . . . . . . .. 4.9. Fragmentation of Neutral Compounds Related to Cyclopeptide Alkaloids ............................................ 4.10. Miscellaneous . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 4.11. Common Fragments ....................................
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5. Identification Strategy .......................................
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6. Physical and Spectral Data of Cyclopeptide Alkaloids and Related Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..
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7. Synthesis ................................................ 147
L. A. Collett et al., Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products © Springer-Verlag/Wien 1998
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D. C. GOURNELIS, G. G. LASKARIS, and R. VERPOORTE
8. Biological Activity. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 8.1. Sedative Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 8.2. Antibacterial Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 8.3. Antifungal Activity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
148 148 149 149
9. Biosynthesis - Tissue Culture .................................. 150 10. Conclusions. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. 150 11. G
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