Aphanorphine, a novel tricyclic alkaloid from the blue-green algaAphanizomenon flos-aquae

作者: Nanda Gulavita , Akira Hori , Yuzuru Shimizu , Parkanyi Laszlo , Jon Clardy

DOI: 10.1016/S0040-4039(00)80500-6

关键词: TricyclicFlosBenzazepineChemistryNeosaxitoxinSaxitoxinAphanizomenon flos-aquae (dietary supplement)StereochemistryAlkaloidAphanizomenonOrganic chemistry

摘要: Abstract An alkaloid with a benzazepine skeleton, aphanorphine (1) was isolated from the blue-green alga, Aphanizomenon flos-aquae together its previously known constituents neosaxitoxin and saxitoxin.

参考文章(9)
KEMMOTSU MITSUHASHI, SHUNSAKU SHIOTANI, RIKIO OHUCHI, KOWASHI SHIRAKI, Syntheses of Azabenzobicycloalkanes Chemical & Pharmaceutical Bulletin. ,vol. 17, pp. 434- 453 ,(1969) , 10.1248/CPB.17.434
Miyoshi Ikawa, Karin Wegener, Thomas L. Foxall, John J. Sasner, Comparison of the toxins of the blue-green alga Aphanizomenon flos-aquae with the Gonyaulax toxins Toxicon. ,vol. 20, pp. 747- 752 ,(1982) , 10.1016/0041-0101(82)90122-2
Tadashi Kometani, Shunsaku Shiotani, Synthesis and analgetic activity of some benzomorphan analogs Journal of Medicinal Chemistry. ,vol. 21, pp. 1105- 1110 ,(1978) , 10.1021/JM00209A003
E. Jackim, J. Gentile, Toxins of a Blue-Green Alga: Similarity to Saxitoxin Science. ,vol. 162, pp. 915- 916 ,(1968) , 10.1126/SCIENCE.162.3856.915
Yuzuru Shimizu, Manuel Norte, Akira Hori, Almoursi Genenah, Masaru Kobayashi, Biosynthesis of saxitoxin analogs: the unexpected pathway Journal of the American Chemical Society. ,vol. 106, pp. 6433- 6434 ,(1984) , 10.1021/JA00333A062
Yuzuru Shimizu, Chien-Ping Hsu, William E. Fallon, Yasukatsu Oshima, Iwao Miura, Koji Nakanishi, Structure of neosaxitoxin Journal of the American Chemical Society. ,vol. 100, pp. 6791- 6793 ,(1978) , 10.1021/JA00489A060
Maktoob Alam, Yuzuru Shimizu, Miyoshi Ikawa, John J. Sasner, Reinvestigation of the toxins from the blue‐green alga, Aphanizomenon flos‐aquae, by a high performance chromatographic method Journal of Environmental Science and Health Part A-toxic\/hazardous Substances & Environmental Engineering. ,vol. 13, pp. 493- 499 ,(1978) , 10.1080/10934527809374828