TY - JOUR
T1 - Heteroaromatic alkaloids, nakijinamines, from a sponge Suberites sp.
AU - Takahashi, Yohei
AU - Tanaka, Naonobu
AU - Kubota, Takaaki
AU - Ishiyama, Haruaki
AU - Shibazaki, Azusa
AU - Gonoi, Tohru
AU - Fromont, Jane
AU - Kobayashi, Jun'Ichi
N1 - Funding Information:
We thank Ms. S. Oka, Ms. A. Tokumitsu, and Ms. T. Komiya, Instrumental Analysis Division, Equipment Management Center, Creative Research Institution, Hokkaido University, for measurements of ESIMS; Dr. Eri Fukushi, Graduate School of Agriculture, Hokkaido University and Mr. T. Hirose, Instrumental Analysis Division, Equipment Management Center, Creative Research Institution, Hokkaido University for measurements of a part of NMR spectra; Mr. Z. Nagahama and K. Uehara for their help with collection of the sponge. This work was partly supported by a research fellowship for young scientists from the Japan Society for the Promotion of Science (to Y.T.) and a Grant-in-Aid for Science Research from the Ministry of Education, Culture, Sports, Science, and Technology of Japan .
PY - 2012/10/14
Y1 - 2012/10/14
N2 - The structures of seven new secondary metabolites isolated from an Okinawan marine sponge Suberites sp., nakijinamines A (1), B (2), and F-I (3-6) and 6-bromoconicamin (7), have been elucidated on the basis of spectroscopic analysis, chemical conversion, and conformational analysis. These analyses disclosed that 1-6 were heteroaromatic alkaloids having the hybrid structures of an aaptamine-type alkaloid and an indole alkaloid, while 7 was a bromoindole alkaloid. Nakijinamine I (6) is the first example of an aaptamine-type alkaloid possessing a 1,4-dioxane ring. Antimicrobial activities of 1-7 were evaluated.
AB - The structures of seven new secondary metabolites isolated from an Okinawan marine sponge Suberites sp., nakijinamines A (1), B (2), and F-I (3-6) and 6-bromoconicamin (7), have been elucidated on the basis of spectroscopic analysis, chemical conversion, and conformational analysis. These analyses disclosed that 1-6 were heteroaromatic alkaloids having the hybrid structures of an aaptamine-type alkaloid and an indole alkaloid, while 7 was a bromoindole alkaloid. Nakijinamine I (6) is the first example of an aaptamine-type alkaloid possessing a 1,4-dioxane ring. Antimicrobial activities of 1-7 were evaluated.
KW - Heteroaromatic alkaloids
KW - Marine sponge
KW - Nakijinamines
KW - Suberites sp.
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U2 - 10.1016/j.tet.2012.08.018
DO - 10.1016/j.tet.2012.08.018
M3 - Article
AN - SCOPUS:84865584295
VL - 68
SP - 8545
EP - 8550
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 41
ER -
