Peroxide Natural Products from <i>Plakortis zyggompha</i> and the Sponge Association <i>Plakortis halichondrioides</i>–<i>Xestospongia deweerdtae</i>: Antifungal Activity
against <i>Cryptococcus gattii</i>
Matthew
T. Jamison
Doralyn S. Dalisay
Tadeusz F. Molinski
10.1021/acs.jnatprod.5b00951.s001
https://acs.figshare.com/articles/journal_contribution/Peroxide_Natural_Products_from_i_Plakortis_zyggompha_i_and_the_Sponge_Association_i_Plakortis_halichondrioides_i_i_Xestospongia_deweerdtae_i_Antifungal_Activity_against_i_Cryptococcus_gattii_i_/2076748
<i>Cryptococcus gattii</i> is a human pathogen and causative
agent of a pernicious, sometimes fatal, disseminated fungal disease.
Investigation of antifungal extracts of the marine sponge association <i>Plakortis halichondrioides</i>–<i>Xestospongia deweerdtae</i> and the sponge <i>Plakortis zyggompha</i> from the Bahamas
led to the discovery and isolation of 6-<i>epi</i>-7,8-dihydroplakortide
K (<b>1</b>), plakortide AA (<b>2</b>), and three new
plakinic acids, N–P (<b>4</b>–<b>6</b>;
unstable 1,2-dioxolanes bearing benzyl-substituted conjugated dienes),
along with known plakinic acids L, K, and M. Chiroptical comparisons and DFT calculations of <sup>13</sup>C NMR
chemical shifts were used to assign the absolute stereostructure of <b>4</b>. The stereospecific base-promoted rearrangement–saponification
of <b>1</b> to <b>10</b> 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 <b>9</b> and <b>11</b> exhibited antifungal activity against <i>C. gattii</i> (MIC<sub>90</sub> = 2.4 to 36 μM), but plakinic
acids N–P were inactive under the same conditions.
2016-02-09 17:06:07
13 C NMR chemical shifts
Plakortis zyggompha
Chiroptical comparisons
MIC 90
Antifungal Activity
antifungal activity
Cryptococcus gattii Cryptococcus gattii
DFT calculations
antifungal extracts
deweerdtae
plakinic acids L
sponge Plakortis zyggompha
stereospecific formation
plakinic acids
Peroxide Natural Products
halichondrioide
plakortides 9