The Hasubanan and Acutumine Alkaloids

Alkaloids: Chemistry and Biology

Volumn 73, Issue , 2014, Pages 161-222

  King, Sandra M ^a   Herzon, Seth B ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

Acutumine; Alkaloid; Biosynthesis; Hasubanan; Isolation; Natural product; Pharmacology; Total synthesis

Indexed keywords

EID: 84886412550     PISSN: 10994831     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-411565-1.00003-2     Document Type: Chapter

References (110)

1. Bentley K.W. The Alkaloids 1971, Vol. 13:1-163. Academic Press, New York. R.H.F. Manske (Ed.).
2. Inubushi Y., Ibuka T. The Alkaloids 1977, Vol. 16:393-430. Academic Press, New York. R.H.F. Manske (Ed.).
3. Matsui M. The Alkaloids 1988, Vol. 33:307-347. Academic Press, New York. A. Brossi (Ed.).
4. Yan M.-H., Cheng P., Jiang Z.-Y., Ma Y.-B., Zhang X.-M., Zhang F.-X., Yang L.-M., Zheng Y.-T., Chen J.-J. J. Nat. Prod. 2008, 71:760.
5. Wang X., Jin H., Li Z., Qin G. Fitoterapia 2007, 78:593.
6. Wang X.-L. Chin. J. Struct. Chem. 2008, 27:1250.
7. Dagne E., Gunatilaka L., Kingston D.G.I. J. Nat. Prod. 1993, 56:2022.
8. Kashiwaba N., Morooka S., Kimura M., Ono M., Toda J., Suzuki H., Sano T. J. Nat. Prod. 1996, 59:476.
9. Semwal D.K., Rawat U. Planta Med. 2009, 75:378.
10. Carroll A.R., Arumugan T., Redburn J., Ngo A., Guymer G.P., Forster P.I., Quinn R.J. J. Nat. Prod. 2010, 73:988.
11. Zhang H., Yue J.-M. J. Nat. Prod. 2005, 68:1201.
12. Jing-Zhen D., Shou-Xun Z. Phytochemistry 1993, 33:941.
13. Zhang H., Wang F.-D., Yue J.-M. Chin. J. Chem. 2006, 24:781.
14. Patra A. Phytochemistry 1987, 26:2391.
15. Xian-kai W., Yu-rui Z., Tong-feng Z., Sheng L., Chun-tao C. Phytochemistry 1993, 35:263.
16. Semwal D.K., Badoni R., Semwal R., Kothiyal S.K., Singh G.J.P., Rawat U. J. Ethnopharmacol. 2010, 132:369.
17. Montagnac A., Gallard J.-F., Litaudon M., Sevenet T., Pais M. Niger. J. Nat. Prod. Med. 1999, 3:83.
18. Cheng P., Ma Y.-B., Yao S.-Y., Zhang Q., Wang E.-J., Yan M.-H., Zhang X.-M., Zhang F.-X., Chen J.-J. Bioorg. Med. Chem. Lett. 2007, 17:5316.
19. Berthou S., Leboeuf M., Cave A., Mahuteau J., David B., Guinaudeau H. J. Org. Chem. 1989, 54:3491.
20. Doskotch R.W., Knapp J.E. Lloydia 1971, 34:292.
21. Furumoto T., Sugimoto Y. Planta Med. 2001, 67:194.
22. Tomita M., Okamoto Y., Kikuchi T., Osaki K., Nishikawa M., Kamiya K., Sasaki Y., Matoba K., Goto K. Tetrahedron Lett. 1967, 8:2421.
23. Tomita M., Okamoto Y., Kikuchi T., Osaki K., Nishikawa M., Kamiya K., Sasaki Y., Matoba K., Goto K. Tetrahedron Lett. 1967, 8:2425.
24. Goto K., Tomita M., Okamoto Y., Kikuchi T., Osaki K., Nishikawa M., Kamiya K., Sasaki Y., Matoba K. Proc. Jpn. Acad 1967, 43:499.
25. Tomita M., Okamoto Y., Kikuchi T., Osaki K., Nishikawa M., Kamiya K., Sasaki Y., Matoba K., Goto K. Chem. Pharm. Bull. 1971, 19:770.
26. Sugimoto Y., Babiker H.A.A., Saisho T., Furumoto T., Inanaga S., Kato M. J. Org. Chem. 2001, 66:3299.
27. Okamoto Y., Yuge E., Nagai Y., Katsuta R., Kishimoto A., Kobayashi Y., Kikuchi T., Tomita M. Tetrahedron Lett. 1969, 10:1933.
28. Chen J.-Y., Xie Y.-F., Zhou T.-X., Qin G.-W. Zhongguo Tianran Yaowu 2012, 10:292.
29. Yu B.-W., Chen J.-Y., Wang Y.-P., Cheng K.-F., Li X.-Y., Qin G.-W. Phytochemistry 2002, 61:439.
30. Sugimoto Y., Inanaga S., Kato M., Shimizu T., Hakoshima T., Isogai A. Phytochemistry 1998, 49:1293.
31. Sugimoto Y., Matsui M., Takikawa H., Sasaki M., Kato M. Phytochemistry 2005, 66:2627.
32. Yu B.-W., Chen J.-Y., Zhou T.-X., Cheng K.-F., Qin G.-W. Nat. Prod. Lett. 2002, 16:155.
33. Hart N.K., Johns S.R., Lamberton J.A., Suares H. Aust. J. Chem. 1972, 25:2289.
34. Goto K., Sudzuki H. Bull. Chem. Soc. Jpn. 1929, 4:220.
35. Goto K., Tomita M., Okamoto Y., Sasaki Y., Matoba K. Proc. Jpn. Acad. 1966, 42:1181.
36. Kato A., Yasui M., Yano N., Kawata Y., Moriki K., Adachi I., Hollinshead J., Nash R.J. Phytochem. Lett. 2009, 2:77.
37. Fadeeva I.I., Il'inskaya T.N., Perel'son M.E., Kuzovkov A.D. Chem. Nat. Compd. 1970, 6:139.
38. Fadeeva I.I., Il'inskaya T.N., Perel'son M.E., Kuzovkov A.D. Chem. Nat. Compd. 1971, 7:756.
39. Zhi-Da M., Ge L., Guang-Xi X., Iinuma M., Tanaka T., Mizuno M. Phytochemistry 1985, 24:3084.
40. Kupchan S.M., Suffness M.I., White D.N.J., McPhail A.T., Sim G.A. J. Org. Chem. 1968, 33:4529.
41. Lao A., Tang Z., Xu R. Yao Xue Xue Bao 1981, 16:940.
42. Matsui M., Yamamura Y., Takebayashi T., Iwaki K., Takami Y., Kunitake K., Koga F., Urasaki S., Watanabe Y. J. Nat. Prod. 1984, 47:858.
43. Kupchan S.M., Liepa A.J., Fujita T. J. Org. Chem. 1973, 38:151.
44. Yamamura Y., Matsui M. J. Nat. Prod. 1985, 48:746.
45. Kupchan S.M., Suffness M.I., McClure R.J., Sim G.A. J. Am. Chem. Soc. 1970, 92:5756.
46. Kupchan S.M., Suffness M.I. Tetrahedron Lett. 1970, 11:4975.
47. Il'inskaya T.N., Fesenko D.A., Fadeeva I.I., Perel'son M.E., Tolkachev O.N. Chem. Nat. Compd. 1971, 7:171.
48. Lao A.-N., Gao Y.-L., Tang Z.-J., Xu R.-S. Yao Hsueh Hsueh Pao 1980, 15:696.
49. Nishikawa M., Kamiya K., Tomita M., Okamoto Y., Kikuchi T., Osaki K., Tomiie Y., Nitta I., Goto K. J. Chem. Soc. B: Phys. Org. 1968, 652.
50. Ichikawa K., Kinoshita T., Itai A., Iitaka Y., Sankawa U. Heterocycles 1984, 22:2071.
51. Wang X., Liu Y., Yang B., Geng Y., Liu D., Huang L. Sep. Sci. Technol. 2011, 46:1534.
52. Sugimoto Y., Matsui M., Babiker H.A.A. Phytochemistry 2007, 68:493.
53. Schultz A.G., Wang A. J. Am. Chem. Soc. 1998, 120:8259.
54. Pihko A.J., Koskinen A.M.P. Tetrahedron 2005, 61:8769.
55. Tomita M., Kozuka M. Tetrahedron Lett. 1966, 7:6229.
56. Bruggink A., McKillop A. Tetrahedron 1975, 31:2607.
57. Toth J.E., Hamann P.R., Fuchs P.L. J. Org. Chem. 1988, 53:4694.
58. Tomita M., Ibuka T., Inubushi Y., Watanabe Y., Matsui M. Tetrahedron Lett. 1964, 5:2937.
59. Herzon S.B., Calandra N.A., King S.M. Angew. Chem. Int. Ed. 2011, 50:8863.
60. Soderquist J.A., Kock I., Estrella M.E. Org. Process Res. Dev. 2006, 10:1076.
61. Corey E.J., Shibata T., Lee T.W. J. Am. Chem. Soc. 2002, 124:3808.
62. Ryu D.H., Lee T.W., Corey E.J. J. Am. Chem. Soc. 2002, 124:9992.
63. Ryu D.H., Zhou G., Corey E.J. J. Am. Chem. Soc. 2004, 126:4800.
64. Crabtree R.H., Felkin H., Morris G.E. J. Organomet. Chem. 1977, 141:205.
65. Suggs J.W., Cox S.D., Crabtree R.H., Quirk J.M. Tetrahedron Lett. 1981, 22:303.
66. Inoki S., Kato K., Takai T., Isayama S., Yamada T., Mukaiyama T. Chem. Lett. 1989, 515.
67. Chuang K.V., Navarro R., Reisman S.E. Angew. Chem. Int. Ed. 2011, 50:9447.
68. Chuang K.V., Navarro R., Reisman S.E. Chem. Sci. 2011, 2:1086.
69. He L., Zhang Y.-H., Guan H.-Y., Zhang J.-X., Sun Q.-Y., Hao X.-J. J. Nat. Prod. 2011, 74:181.
70. Trauner D., Porth S., Opatz T., Bats J.W., Giester G., Mulzer J. Synthesis 1998, 653.
71. Ghosh R., Robinson R. J. Chem. Soc. 1944, 506.
72. Mulzer J., Dürner G., Trauner D. Angew. Chem. Int. Ed. 1996, 35:2830.
73. Ito Y., Hirao T., Saegusa T. J. Org. Chem. 1978, 43:1011.
74. Nguyen T.X., Kobayashi Y. J. Org. Chem. 2008, 73:5536.
75. Jacobi P.A., Kravitz J.I., Zheng W. J. Org. Chem. 1995, 60:376.
76. Jones S.B., He L., Castle S.L. Org. Lett. 2006, 8:3757.
77. Jones S.B., He L., Castle S.L. Org. Lett. 2009, 11:785.
78. Kurosawat K., Ollist W.D., Sutherland I.O., Gottlieb O.R., De Oliveira A.B. Phytochemistry 1978, 17:1389.
79. Reeder M.D., Srikanth G.S.C., Jones S.B., Castle S.L. Org. Lett. 2005, 7:1089.
80. Nielsen D.K., Nielsen L.L., Jones S.B., Toll L., Asplund M.C., Castle S.L. J. Org. Chem. 2009, 74:1187.
81. Nakamura M., Hirai A., Sogi M., Nakamura E. J. Am. Chem. Soc. 1998, 120:5846.
82. Li F., Tartakoff S.S., Castle S.L. J. Am. Chem. Soc. 2009, 131:6674.
83. Li F., Tartakoff S.S., Castle S.L. J. Org. Chem. 2009, 74:9082.
84. King S.M., Calandra N.A., Herzon S.B. Angew. Chem. Int. Ed. 2013, 52:3642.
85. Li F., Castle S.L. Org. Lett. 2007, 9:4033.
86. Myers A.G., Hammond M., Wu Y. Tetrahedron Lett. 1996, 37:3083.
87. Corey E.J., Helal C.J. Angew. Chem. Int. Ed. 1998, 37:1986.
88. Smith A.B., Han Q., Breslin P.A.S., Beauchamp G.K. Org. Lett. 2005, 7:5075.
89. Dess D.B., Martin J.C. J. Am. Chem. Soc. 1991, 113:7277.
90. Moreau R.J., Sorensen E.J. Tetrahedron 2007, 63:6446.
91. Navarro R., Reisman S.E. Org. Lett. 2012, 14:4354.
92. Hersel U., Steck M., Seifert K. Eur. J. Org. Chem. 2000, 1609.
93. Novak B.H., Hudlicky T., Reed J.W., Mulzer J., Trauner D. Curr. Org. Chem. 2000, 4:343.
94. Sugimoto Y. Biotechnol. Agric. For. 2002, 51:281.
95. Barton D.H.R., Kirby A.J., Kirby G.W. J. Chem. Soc. C 1968, 929.
96. Matoba K., Karibe N., Yamazaki T. Chem. Pharm. Bull. 1982, 30:3906.
97. Matoba K., Karibe N., Yamazaki T. Chem. Pharm. Bull. 1984, 32:2639.
98. Waller D.L., Stephenson C.R.J., Wipf P. Org. Biomol. Chem. 2007, 5:58.
99. Sugimoto Y., Hori R. Alkaloids: Properties, Applications and Pharmacological Effects 2010, 139-169. Nova Science Publishers, Hauppauge (NY). N.M. Cassiano (Ed.).
100. Sugimoto Y., Uchida S., Inanaga S., Kimura Y., Hashimoto M., Isogai A. Biosci. Biotechnol. Biochem. 1996, 60:503.
101. Babiker H.A.A., Sugimoto Y., Saisho T., Inanaga S., Hashimoto M., Isogai A. Biosci. Biotechnol. Biochem. 1999, 63:515.
102. Zenk M.H., Rueffer M., Amann M., Deus-Neumann B., Nagakura N. J. Nat. Prod. 1985, 48:725.
103. Hori R., Sugimoto G., Matsui M., Yamauchi Y., Takikawa H., Sugimoto Y. Biosci. Biotechnol. Biochem. 2009, 73:440.
104. Babiker H.A.A., Sugimoto Y., Saisho T., Inanaga S. Phytochemistry 1999, 50:775.
105. Sugimoto Y., Uchida S., Inanaga S., Isogai A. J. Plant Physiol. 1997, 150:376.
106. Jacquet Y.F., Klee W.A., Rice K.C., Iijima I., Minamikawa J. Science 1977, 198:842.
107. Likhitwitayawuid K., Angerhofer C.K., Chai H., Pezzuto J.M., Cordell G.A., Ruangrungsi N. J. Nat. Prod. 1993, 56:1468.
108. Nozaka T., Watanabe F., Tadaki S., Ishino M., Morimoto I., Kunitomo J., Ishii H., Natori S. Mutat. Res. Genet. Toxicol. Test. 1990, 240:267.
109. Qin, G. -W.; Tang, X. -C.; Lestage, P.; Caignard, D. -H.; Renard, P. Acutumine and Acutumine Compounds, Synthesis and Use. Patent WO2004000815A1, 2003.
110. Min Y., Choi S., Lee K. Arch. Pharmacal Res. 2006, 29:627.