TY - JOUR
T1 - Stereochemical Assignment and Biological Evaluation of BE-14106 Unveils the Importance of One Acetate Unit for the Antifungal Activity of Polyene Macrolactams
AU - Fujita, Kohei
AU - Sugiyama, Ryosuke
AU - Nishimura, Shinichi
AU - Ishikawa, Naoki
AU - Arai, Midori A.
AU - Ishibashi, Masami
AU - Kakeya, Hideaki
N1 - Publisher Copyright:
© 2016 The American Chemical Society and American Society of Pharmacognosy.
Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.
PY - 2016/7/22
Y1 - 2016/7/22
N2 - Heronamides are a class of potent antifungal metabolites produced by marine-derived actinomycetes. The number of hydroxy groups and the stereochemistry of the two hydroxylated methine carbons are important for the activity of heronamide C, whereas the effect of the hydrocarbon chains is not known. In this study, the stereochemistry and the biological activity of BE-14106, another member of the heronamide class of antibiotics, isolated from an actinomycete Actinoalloteichus cyanogriseus IFM 11549 was investigated. Spectroscopic analysis coupled with photo- and O2-induced conversion revealed that BE-14106 and the heronamides had the same stereochemistry. BE-14106 showed potent growth inhibition against fission yeast cells with an MIC value of 0.50 μM (0.21 μg/mL), being 4 times less potent than heronamide C, which revealed the importance of the structure of the hydrocarbon tail for the activity.
AB - Heronamides are a class of potent antifungal metabolites produced by marine-derived actinomycetes. The number of hydroxy groups and the stereochemistry of the two hydroxylated methine carbons are important for the activity of heronamide C, whereas the effect of the hydrocarbon chains is not known. In this study, the stereochemistry and the biological activity of BE-14106, another member of the heronamide class of antibiotics, isolated from an actinomycete Actinoalloteichus cyanogriseus IFM 11549 was investigated. Spectroscopic analysis coupled with photo- and O2-induced conversion revealed that BE-14106 and the heronamides had the same stereochemistry. BE-14106 showed potent growth inhibition against fission yeast cells with an MIC value of 0.50 μM (0.21 μg/mL), being 4 times less potent than heronamide C, which revealed the importance of the structure of the hydrocarbon tail for the activity.
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U2 - 10.1021/acs.jnatprod.6b00250
DO - 10.1021/acs.jnatprod.6b00250
M3 - Article
C2 - 27331864
AN - SCOPUS:84979642414
SN - 0163-3864
VL - 79
SP - 1877
EP - 1880
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 7
ER -
