Choon Yong Tan1, Fengrui Wang1, Gerardo D Anaya-Eugenio1, Judith C Gallucci2, Kristie D Goughenour3, Chad A Rappleye3, Richard W Spjut4, Esperanza J Carcache de Blanco1,5, A Douglas Kinghorn1, L Harinantenaina Rakotondraibe1. 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.
Four new metabolites, 4-epi-citreoviridin (1), pan class="Chemical">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.
Authors: Leslie N Aldrich; Joanna E Burdette; Esperanza Carcache de Blanco; Christopher C Coss; Alessandra S Eustaquio; James R Fuchs; A Douglas Kinghorn; Amanda MacFarlane; Brittney K Mize; Nicholas H Oberlies; Jimmy Orjala; Cedric J Pearce; Mitch A Phelps; Liva Harinantenaina Rakotondraibe; Yulin Ren; Djaja Doel Soejarto; Brent R Stockwell; Jack C Yalowich; Xiaoli Zhang Journal: J Nat Prod Date: 2022-02-25 Impact factor: 4.803
Authors: Yan Zhang; Choon Yong Tan; Richard W Spjut; James R Fuchs; A Douglas Kinghorn; Liva Harinantenaina Rakotondraibe Journal: Phytochemistry Date: 2020-10-21 Impact factor: 4.072