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Chemical investigation of two Irciniidae sponges collected by hand (SCUBA) from Australian near shore waters, afforded six new examples of a rare class of sesterterpene lactam; ircinialactams B ( 1 ), G ( 2 ), H ( 5 ), and I ( 6 ), and 8-hydroxyircinialactams C ( 3 ) and G ( 4 ); together with the new biosynthetically related lactone, ircinialactone A ( 7 ). Also isolated were seven biosynthetically related known Irciniidae metabolites; ircinialactams A ( 8 ) and C ( 9 ), (7 E ,12 E ,20 Z ,18 S )-variabilin ( 10 ), (7 Z ,12 Z ,20 Z ,18 S )-variabilin ( 11 ), (7 E ,12 Z ,20 Z ,18 S )-variabilin ( 12 ), (7 Z ,12 E ,20 Z ,18 S )-variabilin ( 13 ) and irciniafuran A ( 14 ). The structure elucidation of 1 – 14 was achieved by detailed spectroscopic analysis, and consideration of a plausible biosynthetic relationship linking Irciniidae sesterterpene β-furans, lactams and lactones. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the leaves of the Australian rainforest tree Cryptocarya mackinnoniana led to the discovery of three new oxygenated phenyl alkyl acids, cryptocaryoic acids A – C and two known compounds, cryptocaryone and 2′,6′-dihydroxy-4′-methoxychalcone. The structures of all the compounds were determined by detailed spectroscopic analysis. Mosher's analysis was used for absolute stereochemistry determination at C-11, while the remaining stereochemistry determination of the one remaining stereocenter C-13 was based on NOESY correlations. All compounds isolated were also evaluated for their anti-inflammatory properties by assessing their inhibitory effects on LPS and interferon-γ induced nitric oxide (NO) production and TNF- α release in RAW 264.7 macrophages. The new cryptocaryoic acids exhibited weak to moderate anti-inflammatory activity (NO inhibition) ranging from (18.4–56 μM). [Display omitted] • Three new phenyl alkyl acids, cryptocaryoic acids A – C, were isolated from the leaves of Cryptocarya mackinnoniana • Cryptocaryoic acids exhibited weak to moderate anti-inflammatory activity • Cryptocaryoic acids are the first in the series of molecules bearing the phenyl oxy-alkyl acid from C.mackinnoniana [ABSTRACT FROM AUTHOR]