Journal
JOURNAL OF NATURAL PRODUCTS
Volume 72, Issue 10, Pages 1857-1863Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np900465e
Keywords
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Funding
- NIH [RO1 CA 047135, U19 CA52955, GM56062, S10 RR19918, S10-RR20939]
- NSF [CHE 0342912]
- NIGMS [GM007910-29]
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Enzyme screening of crude sponge extracts prioritized a 2005 Papua New Guinea collection of Hyrtios sp. for further study. The MeOH extract contained puupehenone and four puupehenone analogues (1, 2, 3, 5, and 7) along with a new diastereomer, 20-epi-hydroxyhaterumadienone (4), and a new analogue, 15-oxo-puupehenoic acid (6). The drimane terpene core of 4 and 6 was rapidly dereplicated, and the modified Mosher's method identified 4, while 1D and 2D NMR techniques were used to solve 6. These compounds plus noteworthy repository natural products and standards were tested against three hpoxygenase isozymes, human 5-, 12-, and 15-lipoxygenases. Significant potency and selectivity profiles were exhibited in the human 5-lipoxygenase assay by puupchenone (1) and jaspaquinol (9) and structural factors responsible for activity identified.
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