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 - Funding Information:
Financial support for this work was provided by Grant R01 CA090265 funded by the National Cancer Institute (NCI, NIH) and Grant P41 GM094060 funded by National Institute of General Medical Sciences (NIGMS, NIH). We thank the Fulbright Visiting Scholar Program, Council for International Exchange of Scholars, Institute of International Education, Washington, D.C., for awarding a Fulbright Fellowship to C.P., and Prof. Lijiang Xuan of Center for Modernization of TCM, Shanghai Institute of Materia Medica, PR China, for obtaining HRESIMS data.
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
AN - SCOPUS:85044515815
VL - 81
SP - 616
EP - 624
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 3
ER -