Biologically active dibenzofurans from Pilidiostigma glabrum, an endemic Australian myrtaceae

Shou, Qingyao, Banbury, Linda K., Renshaw, Dane E., Lambley, Eleanore H., Mon, Htwe, Macfarlane, Graham A., Griesser, Hans J., Heinrich, Michael M. and Wohlmuth, Hans (2012) Biologically active dibenzofurans from Pilidiostigma glabrum, an endemic Australian myrtaceae. Journal of Natural Products, 75 9: 1612-1617. doi:10.1021/np300433r

Author Shou, Qingyao
Banbury, Linda K.
Renshaw, Dane E.
Lambley, Eleanore H.
Mon, Htwe
Macfarlane, Graham A.
Griesser, Hans J.
Heinrich, Michael M.
Wohlmuth, Hans
Title Biologically active dibenzofurans from Pilidiostigma glabrum, an endemic Australian myrtaceae
Formatted title
Biologically active dibenzofurans from Pilidiostigma glabrum, an endemic Australian myrtaceae
Journal name Journal of Natural Products   Check publisher's open access policy
ISSN 0163-3864
Publication date 2012-09-28
Sub-type Article (original research)
DOI 10.1021/np300433r
Open Access Status Not Open Access
Volume 75
Issue 9
Start page 1612
End page 1617
Total pages 6
Place of publication Washington, DC, United States
Publisher American Chemical Society
Language eng
Formatted abstract
n an effort to identify new anti-inflammatory and antibacterial agents with potential application in wound healing, five new dibenzofurans, 1,3,7,9-tetrahydroxy-2,8-dimethyl-4,6-di(2-methylbutanoyl)dibenzofuran (1), 1,3,7,9-tetrahydroxy-2,8-dimethyl-4-(2-methylbutanoyl)-6-(2-methylpropionyl)dibenzofuran (2), 1,3,7,9-tetrahydroxy-2,8-dimethyl-4,6-di(2-methylpropionyl)dibenzofuran (3), 1,3,7,9-tetrahydroxy-4,6-dimethyl-2-(2-methylbutanoyl)-8-(2-methylpropionyl)dibenzofuran (4), and 1,3,7,9-tetrahydroxy-4,6-dimethyl-2,8-di(2-methylpropionyl)dibenzofuran (5), were isolated from the leaves of Pilidiostigma glabrum together with one previously described dibenzofuran. Structure elucidation was achieved by way of spectroscopic measurements including 2D-NMR spectroscopy. Compounds with 2,8-acyl substitutions had potent antibacterial activity against several Gram-positive strains (MIC in the low micromolar range), while compounds with 4,6-acyl substitutions were less active. All compounds except 3 inhibited the synthesis of nitric oxide in RAW264 macrophages with IC50 values in the low micromolar range. Compounds with 2,8-acyl substitutions also inhibited the synthesis of PGE2 in 3T3 cells, whereas 4,6-acyl-substituted compounds were inactive. None of the compounds inhibited the synthesis of TNF-α in RAW264 cells. The compounds showed variable but modest antioxidant activity in the oxygen radical absorbance capacity assay. These findings highlight that much of the Australian flora remains unexplored and may yet yield many new compounds of interest. Initial clues are provided on structure/activity relationships for this class of bioactives, which may enable the design and synthesis of compounds with higher activity and/or selectivity.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
School of Chemistry and Molecular Biosciences
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Created: Sat, 27 Oct 2012, 01:46:01 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences