TY - JOUR
T1 - Isolation, structure determination, and total synthesis of hoshinoamide c, an antiparasitic lipopeptide from the marine cyanobacterium caldora penicillata
AU - Suenaga, Kiyotake
AU - Iwasaki, Arihiro
AU - Ohtomo, Keisuke
AU - Kurisawa, Naoaki
AU - Shiota, Ikuma
AU - Rahmawati, Yulia
AU - Jeelani, Ghulam
AU - Nozaki, Tomoyoshi
N1 - Funding Information:
This work was supported by JSPS KAKENHI (Grant Numbers 18K14346 and 20H02870).
PY - 2021
Y1 - 2021
N2 - Hoshinoamide C (1), an antiparasitic lipopeptide, was isolated from the marine cyanobacterium Caldora penicillata. Its planar structure was elucidated by spectral analyses, mainly 2D NMR, and the absolute configurations of the α-amino acid moieties were determined by degradation reactions followed by chiral-phase HPLC analyses. To clarify the absolute configuration of an unusual amino acid moiety, we synthesized two possible diastereomers of hoshinoamide C and determined its absolute configuration based on a comparison of their spectroscopic data with those of the natural compound. Hoshinoamide C (1) did not exhibit any cytotoxicity against HeLa or HL60 cells at 10 μM, but inhibited the growth of the parasites responsible for malaria (IC50 0.96 μM) and African sleeping sickness (IC50 2.9 μM).
AB - Hoshinoamide C (1), an antiparasitic lipopeptide, was isolated from the marine cyanobacterium Caldora penicillata. Its planar structure was elucidated by spectral analyses, mainly 2D NMR, and the absolute configurations of the α-amino acid moieties were determined by degradation reactions followed by chiral-phase HPLC analyses. To clarify the absolute configuration of an unusual amino acid moiety, we synthesized two possible diastereomers of hoshinoamide C and determined its absolute configuration based on a comparison of their spectroscopic data with those of the natural compound. Hoshinoamide C (1) did not exhibit any cytotoxicity against HeLa or HL60 cells at 10 μM, but inhibited the growth of the parasites responsible for malaria (IC50 0.96 μM) and African sleeping sickness (IC50 2.9 μM).
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U2 - 10.1021/acs.jnatprod.0c01209
DO - 10.1021/acs.jnatprod.0c01209
M3 - Article
AN - SCOPUS:85099112647
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
ER -