TY - JOUR
T1 - Eudistomidin G, a new β-carboline alkaloid from the Okinawan marine tunicate Eudistoma glaucus and structure revision of eudistomidin B
AU - Takahashi, Yohei
AU - Ishiyama, Haruaki
AU - Kubota, Takaaki
AU - Kobayashi, Jun'ichi
N1 - Funding Information:
Authors thank Ms. A. Tokumitsu, Center for Equipment Management Center, Hokkaido University, for measurements of ESIMS. 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 Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan .
PY - 2010/7/15
Y1 - 2010/7/15
N2 - A new β-carboline alkaloid, eudistomidin G (1), has been isolated from the Okinawan marine tunicate Eudistoma glaucus, and the structure was elucidated from spectroscopic data. Furthermore, the structure of eudistomidin B (2), which has been isolated from the same tunicate, was revised from 2a to 2b by detailed analyses of spectroscopic data. Asymmetric synthesis of the revised structure (2b) of eudistomidin B (2) and its (1S,10S)-diastereomer (2c) has been accomplished with the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of eudistomidin B (2) was confirmed to be 2b possessing (1R,10S)-configuration, from comparison of the 1H NMR data, CD spectra, [α] D values, and HPLC analysis of 2b, 2c, and natural eudistomidin B.
AB - A new β-carboline alkaloid, eudistomidin G (1), has been isolated from the Okinawan marine tunicate Eudistoma glaucus, and the structure was elucidated from spectroscopic data. Furthermore, the structure of eudistomidin B (2), which has been isolated from the same tunicate, was revised from 2a to 2b by detailed analyses of spectroscopic data. Asymmetric synthesis of the revised structure (2b) of eudistomidin B (2) and its (1S,10S)-diastereomer (2c) has been accomplished with the Noyori catalytic asymmetric hydrogen-transfer reaction. The absolute configuration of eudistomidin B (2) was confirmed to be 2b possessing (1R,10S)-configuration, from comparison of the 1H NMR data, CD spectra, [α] D values, and HPLC analysis of 2b, 2c, and natural eudistomidin B.
KW - β-Carboline alkaloids
KW - Eudistoma glaucus
KW - Eudistomidins B and G
KW - Tunicate
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U2 - 10.1016/j.bmcl.2010.05.071
DO - 10.1016/j.bmcl.2010.05.071
M3 - Article
C2 - 20541407
AN - SCOPUS:77953870936
SN - 0960-894X
VL - 20
SP - 4100
EP - 4103
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 14
ER -
