Monoterpenoid Indole Alkaloids from the Bark of Alstonia scholaris

Abstract

Six new monoterpenoid indole alkaloids, scholarisines B−G (1–6), together with 15 known analogues (7–21), were isolated from the bark of Alstonia scholaris. Their structures were determined by 1D and 2D NMR spectra and MS analyses. The structure of 1 was further supported by the single-crystal X-ray.

Alstonia scholaris - Apocynaceae - monoterpenoid indole alkaloids - scholarisines B–G

References

• 1 Li P T, Leeuwenberg A JM, Middleton D J. Flora China, Vol. 16. Beijing; Science Press 1995: 154
• 2 Hutchinson C R. Camptothecin: chemistry, biogenesis and medicinal chemistry.  Tetrahedron. 1981;  37 1047-1065
• 3 Buckingham J. Dictionary of natural products on CD‐ROM. England; CRC Press 2006
• 4 Cai X H, Du Z Z, Luo X D. Unique monoterpenoid indole alkaloids from Alstonia scholaris.  Org Lett. 2007;  9 1817-1820
• 5 Cai X H, Tan Q G, Liu Y P, Feng T, Du Z Z, Li W Q, Luo X D. A cage-monoterpenoid indole alkaloid from Alstonia scholaris.  Org Lett. 2008;  10 577-580
• 6 Abe F, Chen R F, Yamauchi T, Marubayashi N, Ueda I. Alschomine and isoalschomine, new alkaloids from the leaves of Alstonia scholaris.  Chem Pharm Bull. 1989;  37 887-890
• 7 Abe F, Yamauchi T. Indole alkaloids from leaves and stems of Leuconotis eugenifolius.  Phytochemistry. 1994;  35 169-171
• 8 Zhou H, He H P, Luo X D, Wang Y H, Yang X W, Di Y T, Hao X J. Three new indole alkaloids from the leaves of Alstonia scholaris.  Helv Chim Acta. 2005;  88 2508-2512
• 9 Abe F, Yamauchi T, Shibuya H, Kitagawa I, Yamashita M. Indole alkaloids from the leaves of Alstonia villosa in Sunbawa.  Chem Pharm Bull. 1998;  46 1235-1238
• 10 Raimo U, Mauri L. ¹³C NMR data of 3-isoajmalicine and 19-epiajmalicine.  Planta Med. 1981;  41 406-418
• 11 Lewin G, Kunesch N, Cave A, Sevenet T, Poisson J. Alcaloids d'Alstonia lanceolifera.  Phytochemistry. 1975;  14 2067-2071
• 12 Atta-ur-Rahman, Alvi K A, Abbas S A, Voelter W. Isolation of 19,20-Z-vallesamine and 19,20-E-vallesamine from Alstonia scholaris.  Heterocycles. 1987;  26 413-419
• 13 Kuehne M E, Xu F, Brook C S. Syntheses of strychnos- and aspidospermatan-type alkaloids. 6. Total syntheses of (±)-echitamidine, (±)-alstogustine, (±)-19-epi-alstogustine, and (±)-akuammicine.  J Org Chem. 1994;  59 7803-7806
• 14 Hu W L, Zhu J P, Hesse M. Indole alkaloids from Alstonia angustifolia.  Planta Med. 1989;  55 463-466
• 15 Yamauchi T, Abe F, Fu C R, Nonaka G I, Santisvk T, Padolima W G. Alkaloids from the leaves of Alstonia scholaris in Taiwan, Thailand, Indonesia and the Philippines.  Phytochemistry. 1990;  29 3547-3552
• 16 Morita Y, Hesse M, Schmid H. Alstonia scholaris: Struktur des Indolalkaloides Narelin.  Helv Chim Acta. 1977;  60 1419-1434
• 17 Lavaud C, Massiot G, Vercauteren J, Le Men-Olivier L. Alkaloids of Hunteria zeylanica.  Phytochemistry. 1982;  21 445-447
• 18 Subramaniam G, Hiraku O, Hayashi M, Koyano T, Komiyama K, Kam T S. Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia.  J Nat Prod. 2007;  70 1783-1789