TY - JOUR
T1 - Nonthmicin, a Polyether Polyketide Bearing a Halogen-Modified Tetronate with Neuroprotective and Antiinvasive Activity from Actinomadura sp.
AU - Igarashi, Yasuhiro
AU - Matsuoka, Noriaki
AU - In, Yasuko
AU - Kataura, Tetsushi
AU - Tashiro, Etsu
AU - Saiki, Ikuo
AU - Sudoh, Yuri
AU - Duangmal, Kannika
AU - Thamchaipenet, Arinthip
PY - 2017/3/17
Y1 - 2017/3/17
N2 - Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.
AB - Nonthmicin (1), a new polyether polyketide bearing a chlorinated tetronic acid, was isolated from the culture extract of a soil-derived Actinomadura strain. The structure of 1 was elucidated by interpretation of NMR and MS spectroscopic data, and the absolute configuration of 1 was proposed on the basis of the crystal structure of its dechloro congener ecteinamycin (2) also isolated from the same strain. Tetronic acids modified by halogenation have never been reported from natural products. Compounds 1 and 2 were found to have neuroprotective activity and antimetastatic properties at submicromolar concentrations in addition to antibacterial activity.
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U2 - 10.1021/acs.orglett.7b00318
DO - 10.1021/acs.orglett.7b00318
M3 - Article
C2 - 28256141
AN - SCOPUS:85015664794
VL - 19
SP - 1406
EP - 1409
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 6
ER -