1. Academic Validation
  2. α-Pyrone and Sterol Constituents of Penicillium aurantiacobrunneum, a Fungal Associate of the Lichen Niebla homalea

α-Pyrone and Sterol Constituents of Penicillium aurantiacobrunneum, a Fungal Associate of the Lichen Niebla homalea

  • J Nat Prod. 2019 Sep 27;82(9):2529-2536. doi: 10.1021/acs.jnatprod.9b00340.
Choon Yong Tan 1 Fengrui Wang 1 Gerardo D Anaya-Eugenio 1 Judith C Gallucci 2 Kristie D Goughenour 3 Chad A Rappleye 3 Richard W Spjut 4 Esperanza J Carcache de Blanco 1 5 A Douglas Kinghorn 1 L Harinantenaina Rakotondraibe 1
Affiliations

Affiliations

  • 1 Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy , The Ohio State University , Columbus , Ohio 43210 , United States.
  • 2 Department of Chemistry and Biochemistry , The Ohio State University , Columbus , Ohio 43210 , United States.
  • 3 Department of Microbiology , The Ohio State University , Columbus , Ohio 43210 , United States.
  • 4 World Botanical Associates, Bakersfield , California , California 93380 , United States.
  • 5 Division of Pharmacy Practice and Science, College of Pharmacy , The Ohio State University , Columbus , Ohio 43210 , United States.
Abstract

Four new metabolites, 4-epi-citreoviridin (1), auransterol (3), and two analogues (2 and 4) of paxisterol (6), together with two known metabolites (15R*,20S*)-dihydroxyepisterol (5) and (6), were isolated from cultures of the Fungal associate, Penicillium aurantiacobrunneum, of the Lichen Niebla homalea, endemic to California and Baja California. The structures of all compounds were determined by comprehensive spectroscopic and spectrometric methods, as well as single-crystal X-ray diffraction for the determination of the absolute configuration of 3. Compound 1 showed selective cytotoxicity toward MCF-7 breast and A2780 ovarian cells with IC50 values of 4.2 and 5.7 μM, respectively.

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