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Peroxide Natural Products from Plakortis zyggompha and the Sponge Association Plakortis halichondrioides–Xestospongia deweerdtae: Antifungal Activity against Cryptococcus gattii
journal contribution
posted on 2016-02-09, 17:06 authored by Matthew
T. Jamison, Doralyn S. Dalisay, Tadeusz F. MolinskiCryptococcus gattii is a human pathogen and causative
agent of a pernicious, sometimes fatal, disseminated fungal disease.
Investigation of antifungal extracts of the marine sponge association Plakortis halichondrioides–Xestospongia deweerdtae and the sponge Plakortis zyggompha from the Bahamas
led to the discovery and isolation of 6-epi-7,8-dihydroplakortide
K (1), plakortide AA (2), and three new
plakinic acids, N–P (4–6;
unstable 1,2-dioxolanes bearing benzyl-substituted conjugated dienes),
along with known plakinic acids L, K, and M. Chiroptical comparisons and DFT calculations of 13C NMR
chemical shifts were used to assign the absolute stereostructure of 4. The stereospecific base-promoted rearrangement–saponification
of 1 to 10 was briefly investigated and
showed tight kinetic control and stereospecific formation of the new
C-2 stereocenter with inversion at C-3. Plakinic acid M and plakortides 9 and 11 exhibited antifungal activity against C. gattii (MIC90 = 2.4 to 36 μM), but plakinic
acids N–P were inactive under the same conditions.
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13 C NMR chemical shiftsPlakortis zyggomphaChiroptical comparisonsMIC 90Antifungal Activityantifungal activityCryptococcus gattii Cryptococcus gattiiDFT calculationsantifungal extractsdeweerdtaeplakinic acids Lsponge Plakortis zyggomphastereospecific formationplakinic acidsPeroxide Natural Productshalichondrioideplakortides 9
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