TY - JOUR
T1 - Cytotoxic and Noncytotoxic Metabolites from Teratosphaeria sp. FL2137, a Fungus Associated with Pinus clausa
AU - Padumadasa, Chayanika
AU - Xu, Ya Ming
AU - Wijeratne, E. M.Kithsiri
AU - Espinosa-Artiles, Patricia
AU - U'Ren, Jana M.
AU - Arnold, A. Elizabeth
AU - Gunatilaka, A. A.Leslie
N1 - Publisher Copyright: © 2018 American Chemical Society and American Society of Pharmacognosy.
PY - 2018/3/23
Y1 - 2018/3/23
N2 - A new naphthoquinone, teratosphaerone A (1), four new naphthalenones, namely, teratosphaerone B (2), structurally related to 1, iso-balticol B (3), iso-balticol B-4,9-acetonide (4), and (+)-balticol C (5), a new furanonaphthalenone, (3aS,9R,9aS)-1(9a),3(3a),9-hexahydromonosporascone (6), and the known metabolite monosporascone (7) were isolated from Teratosphaeria sp. FL2137, a fungal strain inhabiting the internal tissue of recently dead but undecomposed foliage of Pinus clausa. The structures of 1-6 were elucidated on the basis of their spectroscopic data including 2D NMR, and absolute configurations of 2, 3, and 6 were determined by the modified Mosher's ester method. When evaluated in a panel of five tumor cell lines, metabolites 1 and 7 isolated from a cytotoxic fraction of the extract exhibited moderate selectivity for metastatic breast adenocarcinoma cell line MDA-MB-231. Of these, 1 showed cytotoxicity to this cell line with an IC 50 of 1.2 ± 0.1 μM.
AB - A new naphthoquinone, teratosphaerone A (1), four new naphthalenones, namely, teratosphaerone B (2), structurally related to 1, iso-balticol B (3), iso-balticol B-4,9-acetonide (4), and (+)-balticol C (5), a new furanonaphthalenone, (3aS,9R,9aS)-1(9a),3(3a),9-hexahydromonosporascone (6), and the known metabolite monosporascone (7) were isolated from Teratosphaeria sp. FL2137, a fungal strain inhabiting the internal tissue of recently dead but undecomposed foliage of Pinus clausa. The structures of 1-6 were elucidated on the basis of their spectroscopic data including 2D NMR, and absolute configurations of 2, 3, and 6 were determined by the modified Mosher's ester method. When evaluated in a panel of five tumor cell lines, metabolites 1 and 7 isolated from a cytotoxic fraction of the extract exhibited moderate selectivity for metastatic breast adenocarcinoma cell line MDA-MB-231. Of these, 1 showed cytotoxicity to this cell line with an IC 50 of 1.2 ± 0.1 μM.
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U2 - 10.1021/acs.jnatprod.7b00838
DO - 10.1021/acs.jnatprod.7b00838
M3 - Article
C2 - 29373790
SN - 0163-3864
VL - 81
SP - 616
EP - 624
JO - Journal Of Natural Products
JF - Journal Of Natural Products
IS - 3
ER -