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1 H and 13 C‐NMR and biological activity investigations of four lichen‐derived compounds
Author(s) -
König Gabriele M.,
Wright Anthony D.
Publication year - 1999
Publication title -
phytochemical analysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.574
H-Index - 72
eISSN - 1099-1565
pISSN - 0958-0344
DOI - 10.1002/(sici)1099-1565(199909/10)10:5<279::aid-pca464>3.0.co;2-3
Subject(s) - chemistry , usnic acid , stereochemistry , lichen , carbon 13 nmr , hopanoids , two dimensional nuclear magnetic resonance spectroscopy , proton nmr , botany , paleontology , structural basin , source rock , biology
The lichen‐derived natural products, atranorin ( 1 ), hopane‐6α, 22‐diol ( 2 ), usnic acid ( 3 ), and vulpinic acid ( 4 ) were analysed by both one and two‐dimensional ( 1 H, 13 C)‐NMR. Experiments employed included COSY, NOESY, XHCO, HMQC and HMBC. For 1 and 2 , fully assigned proton NMR data are reported for the first time; the reassigned 13 C NMR data for both 1 and 2 are also reported. For 3 , cross‐peaks were observed in the HMBC spectrum that suggest that CH long‐range coupling through H bonds is occurring. Biological activity investigations of each compound indicated hopane‐6α, 22‐diol ( 2 ) to have anti‐tubercular activity (MIC 8 µg/mL) and usnic acid ( 3 ) to be very weakly cytotoxic (ED 50 13 µg/mL). Copyright © 1999 John Wiley & Sons, Ltd.