Biphenyl and Biphenyl Ether Quinolizidine N-oxide Alkaloids from Lagerstroemia indica L.

Abstract

Four new biphenyl and biphenyl ether quinolizidine N-oxide alkaloids, 5-epi-dihydrolyfoline N-oxide (1), decamine N-oxide (2), lagerstroemine N-oxide (3), and lagerine N-oxide (4), were isolated from the aerial parts of Lagerstroemia indica, and their structures were established by extensive spectroscopic studies. In addition, the inhibitory effects of isolated compounds on rat lens aldose reductase (RLAR) were examined.

Key words

Lagerstroemia indica - Lythraceae - quinolizidine alkaloid - molecular modeling - aldose reductase

References

• 1 Chopra R N, Nayar S L, Chopra I C. Glossary of Indian medicinal plants. (Including the Supplement). New Delhi: Council of Scientific and Industrial Research; 1986
• 2 Kirtikar K R, Basu B D. Indian medicinal plant. Vol. III Dehradun, India: International Book Distributors and Publishers; 1935
• 3 Ferris J P. Lythraceae alkaloids. I. Isolation and structural studies of the alkaloids of Decodon verticillatus (L.) Ell.  J Org Chem. 1962;  27 2985-2990
• 4 Ferris J P, Boyce C B, Briner C B. Lythraceae alkaloids. IX. The isolation and structure elucidation of the alkaloids of Lagerstroemia indica L.  J Am Chem Soc. 1971;  93 2958-2962
• 5 Kim H J, Lee I S, Youn U J, Chen Q C, Ngoc T M, Ha D T, Liu H, Min B S, Lee J Y, Seong R S, Bae K H. Biphenylquinolizidine alkaloids from Lagerstroemia indica.  J Nat Prod. 2009;  72 749-752
• 6 Bai Y, Desal H, Pelletier S. N-Oxides of some norditerpenoid alkaloids.  J Nat Prod. 1995;  58 929-933
• 7 Gao W, Li Y, Jiang S, Zhu D. Three lycopodium alkaloid N-oxides from Huperzia serrata.  Planta Med. 2000;  66 664-667
• 8 Kobayashi S, Satoh K, Numata A, Shingu T, Kihara M. Alkaloid N-oxides from Lycoris sanguinea.  Phytochemistry. 1991;  30 675-677
• 9 Lin F W, Wang J J, Wu T S. New pavine N-oxide alkaloids from the stem bark of Cryptocarya chinensis Hemsl.  Chem Pharm Bull. 2002;  50 157-159
• 10 Morita H, Yoshida N, Kobayashi J. Daphnezomines C, D, and E, new alkaloids with an N-oxide moiety from Daphniphyllum humile.  Tetrahedron. 1999;  55 12549-12556
• 11 Murakoshi I, Kidoguchi E, Nakamura M, Haginiwas J, Ohmiya S, Higashiyama K, Otomasa H. (−)-Epilamprolobine and its N-oxide lupin alkaloids from Sophora tomentosa.  Phytochemistry. 1981;  20 1725-1730
• 12 Velcheva M, Danghaaghiin S, Samdanghiin Z, Yansanghiin Z, Hesse M. Epimeric pavine N-oxides from Thalictrum simplex.  Phytochemistry. 1995;  39 683-687
• 13 Matsuda H, Morikawa T, Toguchida I, Yoshikawa M. Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity.  Chem Pharm Bull. 2002;  50 788-795
• 14 Jung S H, Lim S S, Lee S, Lee Y S, Shin K H, Kim Y S. Aldose-reductase inhibitory activity of methanol extracts from the Korean plants.  Nat Prod Sci. 2003;  9 34-37