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Four unusual steckwaic acids E–H (<b>1</b>–<b>4</b>), possessing a rarely described acrylic acid unit at C-4 (<b>1</b>–<b>3</b>) or a double bond between C-12 and C-13 (<b>4</b>) are reported for the first time, along with four new analogues (<b>5</b>–<b>8</b>) and two known congeners (<b>9</b> and <b>10</b>). They were purified from the organic extract of <i>Penicillium steckii</i> AS-324, an endozoic fungus obtained from a deep-sea coral <i>Acanthogorgiidae</i> sp., which was collected from the Magellan Seamount at a depth of 1458 m. Their structures were determined by the interpretation of NMR and mass spectroscopic data. The relative and absolute configurations were determined by NOESY correlations, X-ray crystallographic analysis, and ECD calculations. All compounds were tested for their antimicrobial activities against human- and aquatic-pathogenic bacteria and plant-related pathogenic fungi.