Hong Zhou,Bailin Cong,Yongqi Tian,Yu He,Huanghao Yang
Three new cyclic lipopeptides (compounds 1–3) were isolated from Bacillus sp. SY27F, which collected from the deep-sea hydrothermal vent in the Indian Ocean. The planar structures of compounds 1–3 were characterized by LC–MS, GC–MS and NMR, whereas their absolute configurations were determined by modified Marfey’s analysis and optical rotation contrast. They shared the same heptapeptide chain (N-L-Gln 1 -D-Leu 2 -L-Leu 3 -L-Val 4 -L-Asp 5 -D-Leu 6 -L-Ile 7 -C), differing only by the length of the fatty acid chain. Compounds 1–3 displayed significant cytotoxic activity against DU145, MCF-7 and HepG2 cancer cell lines with IC 50 values of 96.8–190.7 nM and moderate to weak cytotoxicity against A549, HeLa and HT1080, with IC 50 values of 9.3–43.2 μM, respectively. However, none of the three compounds showed any antibacterial activity against Escherichia coli, Staphylococcus aureus and Monilia albicans .
Hong Zhou,Yu He,Yongqi Tian,Bailin Cong,Huanghao Yang
Bacilohydrin A, a new cyclic lipopeptide composed of seven mixed D/L-amino acids (L-Ile1—L-Leu2—D-Asp3—L-Val4—L-Leu5—L-Leu6—L-Gln7) and a (R)-3-hydroxy-12-methyltetradecanoic acid (HMT) residue, was isolated from the crude culture extract of Bacillus sp. SY27F, which was obtained from the Indian Ocean hydrothermal vent. Its planar structure was elucidated by spectroscopic analyses, including 1D and 2D NMR spectroscopy, mass spectrometry (MS), and secondary ion mass spectrometry (MS/MS), whereas its absolute configuration was determined by modified Marfey's analysis. Bacilohydrin A displayed significant cytotoxicities against DU-145, MCF-7 and HepG2 cancer cell lines with IC50 values of 50.3-175.1 nM. Additionally, this is the first time to determine the absolute configuration of a D-aspartic acid residue in surfactin class.