The ajmaline group of indole alkaloids

Alkaloids: Chemistry and Biology

Volumn 55, Issue C, 2001, Pages 1-87

  Lounasmaa, Mauri ^a   Hanhinen, Pirjo ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

AJMALINE; ANTIARRHYTHMIC AGENT; INDOLE ALKALOID; PLANT EXTRACT;

APOCYNACEAE; CHEMICAL STRUCTURE; CHEMISTRY; MASS SPECTROMETRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE; REVIEW; SYNTHESIS;

AJMALINE; ANTI-ARRHYTHMIA AGENTS; APOCYNACEAE; INDOLE ALKALOIDS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT EXTRACTS;

EID: 0035238311     PISSN: 10994831     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0099-9598(01)55002-6     Document Type: Review

References (326)

1. Taylor W.I. In: Manske R.H.F. (Ed). The Alkaloids Vol. 8 (1965), Academic Press, New York 785
2. Taylor W.I. In: Manske R.H.F. (Ed). The Alkaloids Vol. 11 (1968), Academic Press, New York 41
3. Koskinen A., and Lounasmaa M. In: Herz W., Grisebach H., and Kirby G.W. (Eds). Progress in the Chemistry of Organic Natural Products Vol. 43 (1983), Springer, Wien 267
4. Saxton J.E. Nat. Prod. Rep. 1 (1984) 21
5. Saxton J.E. Nat. Prod. Rep. 2 (1985) 49
6. Saxton J.E. Nat. Prod. Rep. 3 (1986) 353
7. Saxton J.E. Nat. Prod. Rep. 4 (1987) 591
8. Saxton J.E. Nat. Prod. Rep. 6 (1989) 1
9. Saxton J.E. Nat. Prod. Rep. 6 (1989) 433
10. Saxton J.E. Nat. Prod. Rep. 7 (1990) 191
11. Saxton J.E. Nat. Prod. Rep. 8 (1991) 251
12. Saxton J.E. Nat. Prod. Rep. 9 (1992) 393
13. Saxton J.E. Nat. Prod. Rep. 10 (1993) 349
14. Saxton J.E. Nat. Prod. Rep. 11 (1994) 493
15. Saxton J.E. Nat. Prod. Rep. 12 (1995) 385
16. Saxton J.E. Nat. Prod. Rep. 13 (1996) 327
17. Saxton J.E. Nat. Prod. Rep. 14 (1997) 559
18. Leonard J. Nat. Prod. Rep. 16 (1999) 319
19. Alvarez M., and Joule J.A. In: Saxton J.E. (Ed). Monoterpenoid Indole Alkaloids (1994), Wiley, Chichester 217 Supplement
20. Hamaker L.K., and Cook J.M. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 9 (1995), Pergamon (Elsevier), Oxford 23
21. Bi Y., Hamaker L.K., and Cook J.M. See also. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry Vol. 13 (1993), Pergamon (Elsevier), Amsterdam 383
22. Stöckigt J. In: Cordell G.A. (Ed). The Alkaloids Vol. 47 (1995), Academic Press, San Diego 115
23. Takayama H., and Sakai S. In: Cordell G.A. (Ed). The Alkaloids Vol. 49 (1997), Academic Press, San Diego 1
24. Takayama H., and Sakai S. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry Vol. 15 (1995), Elsevier, Amsterdam 465
25. Lounasmaa M., Hanhinen P., and Westersund M. (née Halonen). In: Cordell G.A. (Ed). The Alkaloids Vol. 52 (1998), Academic Press, San Diego 103
26. Le Men J., and Taylor W.I. Experientia 21 (1965) 508
27. Danieli B., Bombardelli E., Bonati A., and Gabetta B. Chim. Ind. (Milan) 53 (1971) 1042
28. Nasser A.M.A.G., and Court W.E. J. Ethnopharmacol. 11 (1984) 99
29. Iwu M.M., and Court W.E. Planta Med. 33 (1978) 360
30. Amer M.M.A., and Court W.E. Planta Med. (1980) 8 Suppl.
31. Iwu M.M., and Court W.E. Planta Med. 36 (1979) 208
32. Iwu M.M., and Court W.E. See also. Planta Med. 38 (1980) 260
33. Amer M.A., and Court W.E. Phytochemistry 20 (1981) 2569
34. Akinloye B.A., and Court W.E. Phytochemistry 19 (1980) 2741
35. Libot F., Miet C., Kunesch N., Poisson J.E., Pusset J., and Sévenet T. Ann. Pharm. Fr. 44 (1986) 477
36. Akinloye B.A., and Court W.E. Planta Med. 37 (1979) 361
37. Court W.E. See also. Can. J. Pharm. Sci. 3 (1968) 70
38. Akinloye B.A., and Court W.E. Phytochemistry 19 (1980) 307
39. Sabri N.N., and Court W.E. Phytochemistry 17 (1978) 2023
40. Iwu M.M., and Court W.E. Planta Med. 45 (1982) 105
41. Habib M.S., and Court W.E. Planta Med. 25 (1974) 331
42. Iwu M.M., and Court W.E. Planta Med. 34 (1978) 390
43. Gorman M., Neuss N., Djerassi C., Kutney J.P., and Scheuer P.J. Tetrahedron 1 (1957) 328
44. Roland M. J. Pharm. Belg. 14 (1959) 347
45. Akinloye B.A., and Court W.E. Planta Med. 41 (1981) 69
46. Timmins P., and Court W.E. See also. Planta Med. 26 (1974) 170
47. Pakrashi S.C., Djerassi C., Wasicky R., and Neuss N. J. Am. Chem. Soc. 77 (1955) 6687
48. Bose S. Naturwiss. 42 (1955) 71
49. Majumdar S.P., Poisson J., and Potier P. Phytochemistry 12 (1973) 1167
50. Djerassi C., and Fishman J. Chem. Ind. (London) (1955) 627
51. Djerassi C., Gorman M., Pakrashi S.C., and Woodward R.B. J. Am. Chem. Soc. 78 (1956) 1259
52. Yu D., and Lin M. Yaoxue Xuebao 17 (1982) 309
53. Yu D., and Lin M. Chem. Abstr. 97 (1982) 3591g
54. Bombardelli E., Bonati A., and Russo G. Fitoterapia 38 (1967) 126
55. Malik A., and Siddiqui S. See also. Pakistan J. Sci. Ind. Res. 22 (1979) 121
56. Iwu M.M., and Court W.E. Planta Med. 32 (1977) 88
57. Feng X., and Fu F. Yaoxue Xuebao 16 (1981) 510
58. Feng X., and Fu F. Chem. Abstr. 97 (1982) 3593j
59. Yu S.W.D., and Fu F. See also. Zhongcaoyao 12 (1981) 385
60. Yu S.W.D., and Fu F. See also. Chem. Abstr. 96 (1982) 196515w
61. Scheuer P.J., Chang M.Y., and Fukami H. J. Org. Chem. 28 (1963) 2641
62. Kan C., Potier P., Kan S.-K., Jokela R., and Lounasmaa M. Phytochemistry 25 (1986) 1783
63. Timmins P., and Court W.E. Phytochemistry 13 (1974) 281
64. Amer M.M.A., and Court W.E. Planta Med. 43 (1981) 94
65. Timmins P., and Court W.E. Planta Med. 29 (1976) 283
66. Iwu M.M., and Court W.E. Planta Med. 33 (1978) 232
67. Iwu M.M., and Court W.E. Experientia 33 (1977) 1268
68. Poisson J., Ulshafer P.R., Paszek L.E., and Taylor W.I. Bull. Soc. Chim. Fr. (1964) 2683
69. Hanaoka M., Hesse M., and Schmid H. Helv. Chim. Acta 53 (1970) 1723
70. Sierra P., and Novotný L. Planta Med. 42 (1981) 108
71. Sierra P., Novotný L., Samek Z., Buděšínský M., Dolejš L., and Bláha K. Collect. Czech. Chem. Commun. 47 (1982) 2912
72. Iwu M.M., and Court W.E. Phytochemistry 17 (1978) 1651
73. Orazi O.O., Corral R.A., and Stoichevich M.E. Can. J. Chem. 44 (1966) 1523
74. Mehri M.H., Rabaron A., Sévenet T., and Plat M.M. Phytochemistry 17 (1978) 1451
75. Iacobucci G., and Deulofeu V. Anales A soc. Quim. Arg. 46 (1958) 143
76. Iacobucci G., and Deulofeu V. Chem. Abstr. 53 (1959) 3595
77. Abaul J., Philogène E., Bourgeois P., Mérault G., Poupat C., Ahond A., and Potier P. J. Nat. Prod. 49 (1986) 829
78. Schuler B.O.G., and Warren F.L. J. Chem. Soc. (1956) 215
79. Koepfli J.B. See also. J. Am. Chem. Soc. 54 (1932) 2412
80. Khan M.A. In: Atta-ur-Rahman (Ed). Nat. Prod. Chem., Proc. Int. Symp. Pak.-U.S. Binad. Workshop, 1st. 1984 (1986), Springer, Berlin 195-212
81. Khan M.A. Chem. Abstr. 106 (1987) 153050y
82. Court W.E., Evans W.C., and Trease G.E. J. Pharm. Pharmacol. 10 (1958) 380
83. Kidd D.A.A. J. Chem. Soc. (1958) 2432
84. Boonchuay W., and Court W.E. See also. Planta Med. 29 (1976) 201
85. Ky P.T., Mau N.D., Van Vinh P., Sau V.T., and Hien N.T. Tap Chi Duoc Hoc (1983) 11
86. Ky P.T., Mau N.D., Van Vinh P., Sau V.T., and Hien N.T. Chem. Abstr. 99 (1983) 191738y
87. Keck J. Naturwiss. 42 (1955) 391
88. Yamaguchi K., Shoji H., and Ito M. Eisei Shikenjo Hôkoku (1958) 78
89. Yamaguchi K., Shoji H., and Ito M. Chem. Abstr. 53 (1959) 17419e
90. Skakun N.M., and Kazarinov N.A. Farm. Zh. (Kiev) (1986) 66
91. Skakun N.M., and Kazarinov N.A. Chem. Abstr. 105 (1986) 178283u
92. Martinez J.A., Gomez C., Santana T., and Velez H. Planta Med. 55 (1989) 283
93. Chatterjee A., and Talapatra S.K. Naturwiss. 42 (1955) 182
94. Chaudbury N.A., and Chatterjee A. J. Sci. Ind. Res. 18B (1959) 130
95. Djerassi C., Gorman M., Nussbaum A.L., and Reynoso J. J. Am. Chem. Soc. 76 (1954) 4463
96. Ishidate M., Okada M., and Saito K. Pharm. Bull. (Japan) 3 (1955) 319
97. Ishidate M., Okada M., and Saito K. Chem. Abstr. 50 (1956) 13369f
98. Müller J.M. Experientia 13 (1957) 479
99. Martinez J.A., Sierra M., and Machua M. See also. Rev. Cubana Quim. 6 (1992) 54
100. Martinez J.A., Sierra M., and Machua M. See also. Chem. Abstr. 120 (1994) 73469r
101. Kan N.K. Chem. Nat. Comp. 26 (1990) 233
102. Kiang A.K., and Wan S.C. J. Chem. Soc. (1960) 1394
103. Iacobucci G., and Deulofeu V. J. Org. Chem. 22 (1957) 94
104. Martino V.S., Bandoni A.L., Hnatyszyn O., Rondina R.V.D., and Coussio J.D. See also. J. Pharm. Pharmacol. 30 (1978) 817
105. Martino V.S., Bandoni A.L., Hnatyszyn O., Rondina R.V.D., and Coussio J.D. See also. Chem. Abstr. 91 (1979) 16638d
106. van Poser G., Henriques A.T., and Henriques J.A.P. Rev. Bras. Farm. 69 (1988) 14
107. van Poser G., Henriques A.T., and Henriques J.A.P. Chem. Abstr. 111 (1989) 201453j
108. Siddiqui S., and Siddiqui R.H. J. Ind. Chem. Soc. 8 (1931) 667
109. van Itallie L., and Steenhauser A.J. Pharm. Weekblad 69 (1932) 334
110. Ruyter C.M., Akram M., Illahi I., and Stöckigt J. Planta Med. 57 (1991) 328
111. Djerassi C., Fishman J., Gorman M., Kutney J.P., and Pakrashi S.C. J. Am. Chem. Soc. 79 (1957) 1217
112. Arthur H.R., and Loo S.N. Phytochemistry 5 (1966) 977
113. Lin M., Yang B., and Yu D. Acta Pharm. Sinica 21 (1986) 114
114. Martinez Perez J.A., Navajas Polo C., and Torres Aleman M.A. Rev. Cubana Farm. 17 (1983) 221
115. Martinez Perez J.A., Navajas Polo C., and Torres Aleman M.A. Chem. Abstr. 101 (1983) 69406h
116. Martinez Perez J.A., Eckacka Oeckomby A.A., Amare Meressa A., and Machua Veitia M. Rev. Cubana Farm. 23 (1989) 117
117. Martinez Perez J.A., Eckacka Oeckomby A.A., Amare Meressa A., and Machua Veitia M. Chem. Abstr 113 (1990) 37702h
118. Martinez P J.A., Rodriguez A M.R., Dehesa M G., and Machua V M. See also. Rev. Cubana Quim. 4 (1988) 43
119. Martinez P J.A., Rodriguez A M.R., Dehesa M G., and Machua V M. See also. Chem. Abstr. 111 (1989) 229015s
120. Schlittler E., Schwarz H., and Bader F. Helv. Chim. Acta 35 (1952) 271
121. Chen W.-H., and Bai Y.-C. Yun-nan Chih Wu Yen Chiu 1 (1979) 37
122. Chen W.-H., and Bai Y.-C. Chem. Abstr. 92 (1980) 194470w
123. St. André A.F., Korzun B., and Weinfeldt F. J. Org. Chem. 21 (1956) 480
124. Martinez J.A., Valero R., Sosa M.E., and Manchúa M. Rev. Cub. Quim. 6 (1992) 48
125. Libot F., Miet C., Kunesch N., Poisson J.E., Pusset J., Sévenet T., Duhet D., Guegan P., and Debray M. Plant. Méd. Phytothér. 21 (1987) 189
126. Libot F., Miet C., Kunesch N., Poisson J.E., Pusset J., Sévenet T., Duhet D., Guegan P., and Debray M. Chem. Abstr. 108 (1988) 201749y
127. Ronchetti F., Russo G., Bombardelli E., and Bonati A. Phytochemistry 10 (1971) 1385
128. Paris R. Ann. Pharm. Fr. 1 (1943) 138
129. Weiming C., Yaping Y., and Xiaotian L. Planta Med. 49 (1983) 62
130. Libot F., Kunesch N., and Poisson J. Phytochemistry 19 (1980) 989
131. Nasser A.M.A.G., and Court W.E. Phytochemistry 22 (1983) 2297
132. Kiang A.K., Lee H., Goh J., and Wan A.S.C. Lloydia 27 (1964) 220
133. Kiang A.K., Loh S.K., Demanczyk M., Gemenden C.W., Papariello G.J., and Taylor W.I. See also. Tetrahedron 22 (1966) 3293
134. Meisel H., Döpke W., and Gründemann E. Tetrahedron Lett. (1971) 1291
135. Chatterjee A., Ghosh A.K., and Chakrabarty M. Experientia 32 (1976) 1236 (the compound originally identified as purpeline (24) was re-identified as rautlexine (23) in ref. 82b)
136. Chatterjee A., Chakrabarty M., Ghosh A.K., Hagaman E.W., and Wenkert E. Tetrahedron Lett. (1978) 3879
137. Plat M., Lemay R., Le Men J., Janot M.-M., Djerassi C., and Budzikiewicz H. Bull. Soc. Chim. Fr. (1965) 2497
138. Ali E., Giri V.S., and Pakrashi S.C. See also. Experientia 31 (1975) 876
139. Janot M.-M., and Le Men J. Ann. Pharm. Fr. 13 (1955) 325
140. Banerji A., and Chakrabarty M. Phytochemistry 13 (1974) 2309
141. Il'yashenko L.I., Malikov V.M., Yagudaev M.R., and Yunusov S.Y. Chem. Nat. Comp. 13 (1977) 324
142. Zhukovich E.N. Chem. Nat. Comp. 13 (1977) 324
143. Yagudaev M.R. Chem. Nat. Comp. 18 (1982) 693
144. Siddiqui S., Haider S.I., Ahmad S.S., and Siddiqui B.S. Tetrahedron 41 (1985) 4577
145. Siddiqui S., and Malik A. J. Chem. Soc. Pak. 1 (1979) 1
146. Koskinen A., and Lounasmaa M. See also. Heterocycles 19 (1982) 851
147. Atta-ur-Rahman, Zaman K., Perveen S., Habib-ur-Rehman, Muzaffar A., Choudhary M.I., and Pervin A. Phytochemistry 30 (1991) 1285
148. Khan N.H., Khan M.A., and Siddiqui S. Pakistan J. Sci. Ind. Res. 8 (1964) 23
149. Khan M.A., Horn H., and Voelter W. Z. Naturforsch. 37b (1982) 494
150. Habib M.S., and Court W.E. Phytochemistry 13 (1974) 661
151. Batista C.V.F., Schripsema J., Verpoorte R., Reich S.B., and Henriques A.T. Phytochemistry 41 (1996) 969
152. Madinaveitia A., Valencia E., Bermejo J., and Gonzalez A.G. Biochem. System. Ecol. 23 (1995) 877
153. Subhadhirasakul S., Takayama H., Aimi N., Ponglux D., and Sakai S. Chem. Pharm. Bull. 42 (1994) 1427
154. Akinloye B.A., and Court W.E. J. Ethnopharmacol. 4 (1981) 99
155. Ulshafer P.R., Bartlett M.F., Dorfman L., Gillen M.A., Schlittler E., and Wenkert E. Tetrahedron Lett. (1961) 363
156. Thomas D.W., and Biemann K. Lloydia 31 (1968) 1
157. Taylor W.I., Frey A.J., and Hofmann A. Helv. Chim. Acta 45 (1962) 611
158. Majumder P., and Basu A. Phytochemistry 21 (1982) 2389
159. Khan M.A., and Siddiqui S. Experientia 28 (1972) 127
160. Amer M.M., and Court W.E. Phytochemistry 19 (1980) 1833
161. Allam K., Beutler J.A., and Le Quesne P.W. J. Nat. Prod. 50 (1987) 623
162. Atta-ur-Rahman, Qureshi M.M., Ali S.S., de Silva K.T.D., and Silva W.S.J. Fitoterapia 61 (1990) 91
163. Banerji A., and Chakrabarty M. See also. Indian J. Chem. 11 (1973) 706
164. Banerji A., and Chakrabarty M. See also. Chem. Abstr. 79 (1973) 134384t
165. Burke D.E., Cook G.A., Cook J.M., Haller K.G., Lazar H.A., and Le Quesne P.W. Phytochemistry 12 (1973) 1467
166. Vercauteren J., Massiot G., Sévenet T., Lévy J., Le Men-Olivier L., and Le Men J. Phytochemistry 18 (1979) 1729
167. Hart N.K., Johns S.R., and Lamberton J.A. Aust. J. Chem. 25 (1972) 2739
168. Caron C., Yachaoui Y., Massiot G., Le Men-Olivier L., Pusset J., and Sévenet T. Phytochemistry 23 (1984) 2355
169. Tunmann P., and Rachor J. Naturwiss. 47 (1960) 471
170. Lyon R.L., Fong H.H.S., Farnsworth N.R., and Svoboda G.H. See also. J. Pharm. Sci. 62 (1973) 218
171. Gorman M., Burlingame A.L., and Biemann K. Tetrahedron Lett. (1963) 39
172. Douzoua L., Mansour M., Debray M.-M., Le Men-Olivier L., and Le Men J. Phytochemistry 13 (1974) 1994
173. Bombardelli E., Bonati A., Danieli B., Gabetta B., and Mustich G. Fitoterapia 45 (1974) 183
174. Titeux F., Richard B., Debray M.-M., Le Men-Olivier L., and Le Men J. Phytochemistry 14 (1975) 1648
175. Combes G., Fonzes L., and Winternitz F. Phytochemistry 5 (1966) 1065
176. Bruneton J., Cavé A., and Moretti C. Fitoterapia 50 (1979) 123
177. Bruneton J., Cavé A., and Moretti C. Chem. Abstr. 92 (1980) 160534e
178. Aynilian G.H., Farnsworth N.R., and Trojánek J. Lloydia 37 (1974) 299
179. Yuldashev P.K., and Yunusov S.Y. Dokl. Akad. Nauk SSSR 154 (1964) 1412
180. Yuldashev P.K., and Yunusov S.Y. Chem. Abstr. 62 (1964) 4409
181. Kasymov S.Z., Aripov K.N., Shakirov T.T., and Yunusov S.Y. See also. Chem. Nat. Comp. 3 (1967) 298
182. Yuldashev P.K., and Yunusov S.Y. Khim. Prin Soedin. 1 (1965) 110
183. Yuldashev P.K., and Yunusov S.Y. Chem Abstr. 63 (1965) 8428a
184. Vachnadze V.Y., Malikov V.M., Mudzhiri K.S., and Yunusov S.Y. See also. Soobshch. Akad. Nauk. Gruz. SSR 66 (1972) 97
185. Vachnadze V.Y., Malikov V.M., Mudzhiri K.S., and Yunusov S.Y. See also. Chem. Abstr. 77 (1972) 31539b
186. Shakirov R., Telezhenetskaya M.V., Bessonova I.A., Aripova S.F., Israilov I.A., Sultankhodzhaev M.N., Vinogradova V.I., Akhmedzhanova V.I., Tulyaganov T.S., Salimov B.T., and Telnov V.A. Chem. Nat. Comp. 32 (1996) 473
187. Zhukovich E.N., and Vachnadze V.Y. Chem. Nat. Comp. 20 (1984) 509
188. Timmins P., and Court W.E. Phytochemistry 13 (1974) 1997
189. Timmins P., and Court W.E. See also. Phytochemistry 15 (1976) 733
190. Court W.E. Planta Med. 27 (1975) 319
191. Hofmann A., and Frey A.J. Helv. Chim. Acta 40 (1957) 1866
192. Khalmirzhaev M.M., Malikov V.M., and Yunusov S.Y. Chem. Nat. Comp. 9 (1973) 657
193. Atta-ur-Rahman, Sultana A., Nighat F., Bhatti M.K., Kurucu S., and Kartal M. Phytochemistry 38 (1995) 1057
194. Ghedira K., Zèches-Hanrot M., Richard B., Massiot G., Le Men-Olivier L., Sévenet T., and Goh S.H. Phytochemistry 27 (1988) 3955
195. Crow W.D., Hancox N.C., Johns S.R., and Lamberton J.A. Aust. J. Chem. 23 (1970) 2489
196. Chérif A., Massiot G., Le Men-Olivier L., Pusset J., and Labarre S. Phytochemistry 28 (1989) 667
197. Cosson J.P. Thèse d'Université (1975), Université de Paris-Sud, Orsay
198. Lewin G., Tamini O., Cabalion P., and Poisson J. Ann. Pharm. Fr. 39 (1981) 273
199. Atta-ur-Rahman, Nighat F., and Choudhary M.I. Heterocycles 27 (1988) 961
200. Abe F., Yamauchi T., and Santisuk T. Phytochemistry 35 (1994) 249
201. Ratnayake C.K., Arambewela L.S.R., De Silva K.T.D., Atta-ur-Rahman, and Alvi K.A. Phytochemistry 26 (1987) 868. Note: The C-2 stereostructure in the formula given for vincamajine (39)_erroneous
202. Kam T., Iek I., and Choo Y. See also. Phytochemistry 51 (1999) 839. Note: The C-2 stereostructure in the formula given for vincamajine (39)_erroneous
203. Mamatas-Kalamaras S., Sévenet T., Thal C., and Potier P. Phytochemistry 14 (1975) 1849
204. Patel M.B., Poisson J., Pousset J.L., and Rowson J.M. J. Pharm. Pharmacol. 17 (1965) 323
205. Goodwin S., and Horning E.C. Chem. Ind. (London) (1956) 846
206. Strouf O., and Kavkova K. Chem. Listy 56 (1962) 987
207. Strouf O., and Kavkova K. Chem. Abstr. 57 (1962) 16673a
208. Aliev A.M., and Babaev N.A. Farmatsiya 25 (1976) 30
209. Aliev A.M., and Babaev N.A. Chem. Abstr. 85 (1976) 106639k
210. Vachnadze V.Y., and Mudzhiri K.S. See also. Khromatogr. Metody Farm. (1977) 156
211. Vachnadze V.Y., and Mudzhiri K.S. See also. Chem. Abstr. 90 (1979) 164704s
212. Chkhikvadze G.V., Vachnadze V.Y., and Mudzhiri K.S. Khim. Prir. Soedin. (1980) 850
213. Chkhikvadze G.V., Vachnadze V.Y., and Mudzhiri K.S. Chem. Abstr. 94 (1981) 1361716
214. Janot M.-M., and Le Men J. C. R. Acad. Sci. Paris, Sér. C 241 (1955) 767
215. Ilyashenko L.I., Malikov V.M., Yagudaev M.R., and Yunusov S.Y. Chem. Nat. Comp. 13 (1977) 324
216. Ratnayake C.K., Arambewela L.S.R., de Silva K.T.D., Atta-ur-Rahman, and Alvi K.A. Phytochemistry 26 (1987) 868
217. Gosset J., Le Men J., and Janot M.-M. Bull. Soc. Chim. Fr. (1961) 1033
218. Janot M.-M., Le Men J., Gosset J., and Lévy J. See also. Bull. Soc. Chim. Fr. (1962) 1079
219. Zhukovich E.N., and Vachnadze V.Y. Chem. Nat. Comp. 21 (1985) 682
220. Muquet M., Pousset J.-L., and Poisson J. C. R. Acad. Sci. Paris, Sér. C 266 (1968) 1542
221. Sadykov Y.D., Khodzhimatov M., and Degtyarev V.A. Dokl. Akad. Nauk Tadzh. SSR 28 (1985) 289
222. Sadykov Y.D., Khodzhimatov M., and Degtyarev V.A. Chem. Abstr. 104 (1986) 17633x
223. Sharipov M.R., Khalmirzaev M.M., Malikov V.M., and Yunusov S.Y. Chem. Nat. Comp. 12 (1976) 355
224. Kaul J.L., and Trojánek J. Lloydia 29 (1966) 26
225. Kaul J.L., and Trojánek J. Chem. Ind. (London) (1966) 853
226. Kaul J.L., Trojánek J., and Bose A.K. Coll. Czech. Chem. Commun. 35 (1970) 116
227. Chkhikvadze G.V., Asatiani V.S., Vachnadze V.Y., and Mudzhiri K.S. Soobshch. Akad. Nauk. Gruz. SSR 64 (1971) 345
228. Chkhikvadze G.V., Asatiani V.S., Vachnadze V.Y., and Mudzhiri K.S. Chem. Abstr. 76 (1972) 700976
229. Lewin G., Kunesch N., Poisson J., and Sévenet T. J. Indian Chem. Soc. 55 (1978) 1096
230. Lewin G., Kunesch N., Cavé A., Sévenet T., and Poisson J. Phytochemistry 14 (1975) 2067
231. Morfaux A.-M., Mouton P., Massiot G., and Le Men-Olivier L. Phytochemistry 29 (1990) 3345
232. Guillaume D., Morfaux A.M., Richard B., Massiot G., Le Men-Olivier L., Pusset J., and Sévenet T. Phytochemistry 23 (1984) 2407
233. Janot M.-M., Le Men J., and Hammouda Y. C. R. Acad. Sci. Paris, Sér. C 243 (1956) 85
234. Trojánek J., and Hodková J. Coll. Czech. Chem. Soc. 27 (1962) 2981
235. Siddiqui S., Haider S.I., and Ahmad S.S. Heterocycles 26 (1987) 463
236. Morfaux A.-M., Mouton P., Massiot G., and Le Men-Olivier L. Phytochemistry 31 (1992) 1079
237. Mukherjee B., Ray A.B., Chatterjee A., and Das B.C. Chem. Ind. (London) (1969) 1387
238. Poisson J., Goutarel R., and Janot M.-M. C. R. Acad. Sci. Paris, Sér. C 241 (1955) 1840
239. Haack E., Popelak A., and Spingler H. Naturwiss. 42 (1955) 627
240. Siddiqui S., Ahmad S.S., and Haider S.I. Planta Med. 53 (1987) 288
241. Iwu M.M. Planta Med. (1980) 13 Suppl.
242. Said I.M., Din L.B., Yusoff N.I., Wright C.W., Cai Y., and Phillipson J.D. J. Nat. Prod. 55 (1992) 1323
243. Elderfield R.C., and Gilman R.E. Phytochemistry 11 (1972) 339
244. Chatterjee A., Ghosh A.K., and Hagaman E.W. J. Org. Chem. 47 (1982) 1732
245. Keawpradub N., and Houghton P.J. Phytochemistry 46 (1997) 757. Note: The C-2 stereostructure in the formula given for alstomacroline (80) is erroneous.
246. Keawpradub N., Eno-Amooquaye E., Burke P.J., and Houghton P.J. See also. Planta Med. 65 (1999) 311. Note: The C-2 stereostructure in the formula given for alstomacroline (80) is erroneous.
247. Albright J.D., and Goldman L. J. Am. Chem. Soc. 89 (1967) 2416
248. Anet F.A.L., Chakravarti D., Robinson R., and Schlittler E. J. Chem. Soc. (1954) 1242
249. Khan M.A., and Ahsan A.M. Tetrahedron Lett. (1970) 5137
250. Schübel H., Treiber A., and Stöckigt J. Helv. Chim. Acta 67 (1984) 2078
251. Stöckigt H., Ruyter C.M., and Stöckigt J. See also. Phytochemistry 28 (1989) 491
252. Ruyter C.M., and Stöckigt J.H.H. Helv. Chim. Acta 74 (1991) 1707
253. Cook J.M., and Le Quesne P.W. J. Org. Chem. 36 (1971) 582 For revised structure of alstonisidine (7) see Ref. 157
254. Burke D.E., Cook J.M., and Le Quesne P.W. J. Am. Chem. Soc. 92 (1973) 546
255. Burke D.E., Cook J.M., and Le Quesne P.W. See also. J. Chem. Soc., Chem. Commun. 11 (1972) 697
256. Masamune S., Ang S.K., Egli C., Nakatsuka N., Sarkar S.K., and Yasunari Y. J. Am. Chem. Soc. 89 (1967) 2506
257. Mashimo K., and Sato Y. Tetrahedron 26 (1970) 803
258. Mashimo K., and Sato Y. See also. Tetrahedron Left. (1969) 901
259. Yoneda N. Chem. Pharm. Bull. 13 (1965) 1231
260. Cloudsdale I.S., Kluge A.F., and McClure N.L. J. Org. Chem. 47 (1982) 919
261. Magnus P., Mugrage B., DeLuca M.R., and Cain G.A. J. Am. Chem. Soc. 112 (1990) 5220
262. Mashimo K., and Sato Y. Tetrahedron Lett. (1969) 905
263. Bailey P.D., and McLay N.R. See also. J. Chem. Soc., Perkin Trans. 1 (1993) 441
264. Li J., and Cook J.M. J. Org. Chem. 63 (1998) 4166
265. Yu P., and Cook J.M. See also. J. Org. Chem. 63 (1998) 91160
266. Cox E.D., Hamaker L.K., Li J., Yu P., Czerwinski K.M., Deng L., Bennett D.W., Cook J.M., Watson W.H., and Krawiec M. J. Org. Chem. 62 (1997) 44
267. van Tamelen E.E., and Oliver L.K. Bioorg. Chem. 5 (1976) 309
268. van Tamelen E.E., and Oliver L.K. See also. J. Am. Chem. Soc. 92 (1970) 2136
269. Lounasmaa M., and Hanhinen P. Tetrahedron 52 (1996) 15225
270. Lounasmaa M., and Hanhinen P. Planta Med. 64 (1998) 572
271. Gamick L., and Le Quesne P.W. J. Am. Chem. Soc. 100 (1978) 4213
272. Khan Z.M., Hesse M., and Schmid H. Helv. Chim. Acta 50 (1967) 1002
273. Lounasmaa M., and Hanhinen P. Seminar on Indole A lkaloids. Espoo (March 31, 1999)
274. Takayama H., Phisalaphong C., Kitajima M., Aimi N., Sakai S., and Stöckigt J. Chem. Pharm. Bull. 39 (1991) 266
275. Endress S., and Stöckigt J. Helv. Chim. Acta 76 (1993) 2544
276. Takayama H., Kitajima M., Suda S., Aimi N., Sakai S., Endress S., and Stöckigt J. Tetrahedron 48 (1992) 2627
277. Endress S., Takayama H., Suda S., Kitajima M., Aimi N., Sakai S., and Stöckigt J. See also. Phytochemistry 32 (1993) 725
278. Phisalaphong C., Takayama H., and Sakai S. Tetrahedron Lett. 34 (1993) 4035
279. Morfaux A.-M., Guillaume D., Massiot G., and Le Men-Olivier L. C. R. Acad. Sci., Sér. 2 309 (1989) 33
280. Stöckigt J., and Zenk M. J. Chem. Soc., Chem. Commun. (1977) 646
281. Rueffer M., Nagakura N., and Zenk M.H. See also. Tetrahedron Lett. (1978) 1593
282. Scott A.O., Lee S.L., de Capite P., Culver M.G., and Hutchinson C.R. Heterocycles 7 (1977) 979
283. Atta-ur-Rahman, and Basha A. Biosynthesis of Indole Alkaloids (1983), Clarendon Press, Oxford 68
284. Luckner M. Secondary Metabolism in Microorganisms, Plants, and Animals. 3rd ed. (1990), Springer Verlag, Berlin 353
285. Bruneton J. Pharmacognosie, Phytochimic, Plantes Médicinales. 2nd ed. (1993), Technique et Documentation, Lavoisier, Paris 821
286. Stöckigt J. Tetrahedron Lett. (1979) 2615
287. Stöckigt J., Pfitzner A., and Keller P.J. Tetrahedron Lett. 24 (1983) 2485
288. Pfitzner A., and Stöckigt J. Planta Med. 48 (1983) 221
289. Pfitzner A., and Stöckigt J. Tetrahedron Lett. 24 (1983) 5197
290. Pfitzner A., and Stöckigt J. J. Chem. Soc., Chem. Comm. (1983) 459
291. Pfitzner A., Krausch B., and Stöckigt J. Tetrahedron 40 (1984) 1691
292. Schmidt D., and Stöckigt J. Planta Med. 61 (1995) 254
293. Martin G.E., and Zektzer A.S. Two-Dimensional NUR Methods for Establishing Molecular Connectivity (1988), VHC-Publishers, Weinheim
294. Atta-ur-Rahman. One and Two Dimensional NMR Spectroscopy (1989), Elsevier, Amsterdam
295. Günther H. La Spectroscopy de RMN (1993), Masson, Paris
296. Neukomm G., Kletzhändler E., and Hesse M. Helv. Chim. Acta 64 (1981) 90
297. Yagudaev M.R. Chem. Nat. Comp. 18 (1982) 442
298. Gabetta B., and Mustich G. Spectral Data of Indole Alkaloids (1975), Inverni della Beffa, Milan
299. Lounasmaa M., and Tolvanen A. Heterocycles 24 (1986) 3229
300. Lounasmaa M., Jokela R., and Kan S.-K. Heterocycles 23 (1985) 1503
301. Koskinen A.M.P., and Lounasmaa M. See also. Heterocycles 24 (1986) 331
302. Jokela R., and Lounasmaa M. Planta Med. 62 (1996) 577
303. Wehrli F.W., Marchand A.P., and Wehrli S. Interpretation of Carbon-13 NMR Spectra (1988), Wiley, Chichester
304. Danieli B., Palmisano G., and Severini Ricca G. Tetrahedron Lett. 22 (1981) 4007
305. Danieli B., Lesma G., Palmisano G., and Severini Ricca G. Tetrahedron 40 (1984) 5255
306. Johnston Jr. M.D., Soltero L.R., and Martin G.E. J. Heterocycl. Chem. 25 (1988) 1803
307. Crouch R.C., and Martin G.E. J. Heterocycl. Chem. 32 (1995) 1665
308. Morales-Rios M.S., Espiñeira J., and Joseph-Nathan P. Magn. Reson. Chem. 25 (1987) 377
309. Verpoorte R., van Beek T.A., Riegman R.L.M., Hylands P.J., and Bisset N.G. Org. Magn. Reson. 22 (1984) 328
310. See also, J. Schripsema and R. Verpoorte, in "Studies in Natural Products Chemistry", (ed. Atta-ur-Rahman), Vol. 9. Elsevier, Amsterdam, pp. 163-199
311. Biemann K. Mass Spectrometry, Organic Chemical Applications (1962), McGraw-Hill, New York
312. Biemann K. See also. In: McLafferty F.W. (Ed). Mass Spectrometry of Organic Ions (1963), McGraw-Hill, New York
313. Budzikiewicz H., Djerassi C., and Williams D.H. Structure Elucidation of Natural Products by Mass Spectrometry, Vol. 1, Alkaloids (1964), Holden-Day, San Francisco
314. Budzikiewicz H., Djerassi C., and Williams D.H. Mass Spectrometry of Organic Compounds. See also (1967), Holden-Day, San Francisco
315. Spiteller G. Massenspektrometrische Strukturanalyse organischer Verbindungen (1966), Verlag Chemie, Weinheim
316. Hesse M. In: Budzikiewicz H. (Ed). Progress in Mass Spectrometry Vol. 1 (1974), Verlag Chemie, Weinheim (Teil 1)
317. de Hoffmann E., Charette J., and Stroobant V. Spectrométrie de Masse (1994), Masson, Paris
318. Biemann K., Bommer P., Burlingame A.L., and McMurray W.J. J. Am. Chem. Soc. 86 (1964) 4624
319. Spiteller G., and Spiteller-Friedmann M. Tetrahedron Lett. (1963) 147
320. Biemann K., Bommer P., Burlingame A.L., and McMurray W.J. Tetrahedron Lett. (1963) 1969
321. Stöckigt J., Pfitzer A., and Firl J. Plant Cell. Rep. 1 (1981) 36
322. Kleinsorge H. Med. Klin. 54 (1959) 409
323. Petter A., and Engelmann K. Arzneim.-Forsch. 24 (1974) 876
324. Heeg E. Arzneim.-Forsch. 27 (1977) 114
325. Makarovich I.F., Ivanov L.V., Khadzhai Y.I., Belokon V.F., Pavlova V.V., Klimenko O.I., Bondar N.Y., and Uryupina E.V. Chem. Nat. Comp. 21 (1985) 224
326. Makarovich I.F., Khadzhai Y.I., Nikolaeva A.V., and Pavlova V.V. See also. Chem. Nat. Comp. 15 (1979) 466