Peniginsengins B–E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11

Abstract

Chemical examination of the EtOAc extract of the deep sea-derived fungus Penicillium sp. YPGA11 resulted in the isolation of four new farnesylcyclohexenones, peniginsengins B–E (1–4), and a known analog peniginsengin A (5). The structures of compounds 1–4 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1, 2, and 4 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compounds 1–5, characterized by a highly oxygenated 1-methylcyclohexene unit and a (4E,8E)-4,8-dimethyldeca-4,8-dienoic acid side chain, are rarely found in nature. Compounds 2–4 exhibited antibacterial activity against Staphylococcus aureus.

Aspterrics A and B, New Sesquiterpenes from Deep Sea-derived Fungus Aspergillus terreus YPGA10

“…The remaining acetyl group was located at C-14 (C 71.3) by the HMBC correlation from H2-14 to the acetyl carbonyl carbon (C 172.9). The strong NOESY correlations of H3-13/H2-5, H2-8/H-6, H3-15/H2-9, and H2-14/H-10 indicated that both Δ 6 and Δ 10 had an E configuration. The specific rotation of 1 ([] 20 D 0) indicated that 1 was racemic.…”

“…Some possess unique carbon skeletons and some exhibit remarkable bioactivities such as enzyme inhibition, antitumor activity, and antiviral activity. As part of our ongoing efforts to discover bioactive molecules from marine-derived fungi [9][10][11], chemical examination of a deep-sea sediment-derived Aspergillus terreus YPGA10 led to the isolation of a carotane-type sesquiterpene aspterric acid (3) and two new biogenetically related sesquiterpenes (1 and 2). Herein, the isolation and structural identification were described.…”

Antibiotics from Extremophilic Micromycetes

“…The chemical study of the extract of deep-sea fungus Penicillium sp. YPGA11 [ 327 ] led to the isolation of four new antibacterial meroterpenoids farnesylcyclohexenones, peniginsengins B–E ( 503 – 506 ), that contained rare motifs for natural compounds, i.e., 1‑methylcyclohexene cycle and (4 E ,8 E )-4,8-dimethyldeca-4,8-dienoic acid.…”

Terpenoids from the Deep-Sea-Derived Fungus Penicillium thomii YPGA3 and Their Bioactivities

“…In our efforts to search for new or bioactive molecules from deep-sea-derived Penicillium or Aspergillus strains [12][13][14][15], chemical examination of Penicillium thomii YPGA3 afforded a new austalide meroterpenoid (1) and seven known analogues (2−8) ( Figure 1). Compound 1 represented the third example of austalides bearing a phenol hydroxy at C-5 instead of the conserved methoxy in other known analogues.…”