TY - JOUR
T1 - Zamamidine C, 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A, and 3,4-dihydromanzamine J N-oxide, new manzamine alkaloids from sponge Amphimedon sp.
AU - Yamada, Mika
AU - Takahashi, Yohei
AU - Kubota, Takaaki
AU - Fromont, Jane
AU - Ishiyama, Aki
AU - Otoguro, Kazuhiko
AU - Yamada, Haruki
AU - Omura, Satoshi
AU - Kobayashi, Jun'ichi
N1 - Funding Information:
We thank Ms. S. Oka, Center for Instrumental Analysis, Hokkaido University, for measurements of ESIMS, and Mr. Z. Nagahama for his help with collection of the sponges. This work was partly supported by funds from the Drugs for Neglected Diseases initiative (DNDi), and a grant for All Kitasato Project Study (AKPS), and Grant-in-Aid for Science Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan.
PY - 2009/3/14
Y1 - 2009/3/14
N2 - New manzamine alkaloids, zamamidine C (1), 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2), and 3,4-dihydromanzamine J N-oxide (3), have been isolated from an Okinawan marine sponge Amphimedon species. The structures and stereochemistries of 1-3 were elucidated from the spectroscopic data and chemical derivatization. Zamamidine C (1) is a new manzamine alkaloid possessing a second β-carboline ring via an ethylene unit at N-2 of manzamine D, while 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2) is the first manzamine alkaloid possessing an epoxide ring at C-10 and C-11. Zamamidine C (1) showed significant antitrypanosomal activity against Trypanosoma brucei brucei, the parasite associated with sleeping sickness, and antimalarial activity against Plasmodium falciparum, the causative agent of malaria in vitro.
AB - New manzamine alkaloids, zamamidine C (1), 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2), and 3,4-dihydromanzamine J N-oxide (3), have been isolated from an Okinawan marine sponge Amphimedon species. The structures and stereochemistries of 1-3 were elucidated from the spectroscopic data and chemical derivatization. Zamamidine C (1) is a new manzamine alkaloid possessing a second β-carboline ring via an ethylene unit at N-2 of manzamine D, while 3,4-dihydro-6-hydroxy-10,11-epoxymanzamine A (2) is the first manzamine alkaloid possessing an epoxide ring at C-10 and C-11. Zamamidine C (1) showed significant antitrypanosomal activity against Trypanosoma brucei brucei, the parasite associated with sleeping sickness, and antimalarial activity against Plasmodium falciparum, the causative agent of malaria in vitro.
KW - 3,4-Dihydro-6-hydroxy-10,11-epoxymanzamine A
KW - 3,4-Dihydromanzamine J N-oxide
KW - Antimalarial activity
KW - Antitrypanosomal activity
KW - Manzamine alkaloid
KW - Sponge
KW - Zamamidine C
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U2 - 10.1016/j.tet.2009.01.032
DO - 10.1016/j.tet.2009.01.032
M3 - Article
AN - SCOPUS:59949095679
SN - 0040-4020
VL - 65
SP - 2313
EP - 2317
JO - Tetrahedron
JF - Tetrahedron
IS - 11
ER -
