Reinvestigation of the secondary metabolites of the soft coral-derived fungus Pestalotiopsis sp. (ZJ-2009-7-6), cultured in a bromine-modified medium, led to the isolation of three new rhamnosylated phenol derivatives, pestarhamnoses A–C ( 1 – 3 ), together with the former metabolites, (±)-pestalachlorides C and D ( 4 and 5 ). Their structures were elucidated through extensive 1D and 2D NMR spectroscopy and mass spectrometry. The relative configurations of the rhamnosyl moieties were determined as α-rhamnoses by their anomeric 1 J CH coupling constants. The absolute configurations of 1 – 3 were determined as L-rhamnose residues by HPLC analysis of their thiocarbamoyl-thiazolidine derivatives and that of authentic L-rhamnose. This is the first report of phenol glycosides with α-L-rhamnose in nature.
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Acknowledgment
We thank Dr. X. Liu (Beijing CIQ) for HR-ESI-MS spectra and acknowledge funding from the Program of National Natural Science Foundation of China (Nos. 41130858; 41322037; 41176121; 81172977), the Natural Science Foundation of Shandong Province (Nos. ZR2011DQ019; ZR2011HM085), and the Program for New Century Excellent Talents in University, Ministry of Education of China (No. NCET-11-0472).
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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2015, pp. 931–934.
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Xing, Q., Li, D., Guo, ZY. et al. Pestarhamnoses A–C, Rhamnosylated Phenol Derivatives from the Soft Coral-Derived Fungus Pestalotiopsis sp.. Chem Nat Compd 51, 1080–1084 (2015). https://doi.org/10.1007/s10600-015-1497-z
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DOI: https://doi.org/10.1007/s10600-015-1497-z