np501052a_si_001.pdf (1.07 MB)
Antipodal Crambescin A2 Homologues from the Marine Sponge Pseudaxinella reticulata. Antifungal Structure–Activity Relationships
journal contribution
posted on 2015-03-27, 00:00 authored by Matthew
T. Jamison, Tadeusz F. MolinskiInvestigation of antifungal natural products from the marine sponge Pseudaxinella reticulata from the Bahamas led to the discovery
of new crambescin homologues (1, 2) and
enantiomers (3, 4) of known natural products.
The cyclic-guanidine structures were solved through analysis of 2D
NMR, MS-MS, and CD data. The absolute configurations of 1–4 were established as 13Ropposite
of known homologues reported from Crambe crambe obtained
from the Mediterranean Seaby comparison of their CD spectra
with predicted Cotton effects obtained from DFT calculations. Antifungal
activities of 1–4 against the pathogenic
strains Candida albicans and Cryptococcus sp. were observed to correlate potency (MIC50 and MIC90) with the length of the alkyl side chain.
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homologueCrambe crambeCD spectraconfigurationalkyl side chainRelationshipsInvestigationMarine Sponge Pseudaxinella reticulataenantiomerantifungalCD dataCotton effectsDFT calculationsstrains Candida albicansAntifungal activitiescrambescinMIC 502 HomologuesBahamaspotencyCryptococcus spAntipodal CrambescinMediterraneananalysislengthmarine sponge Pseudaxinella reticulata2 D NMR
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