TY - JOUR
T1 - Benzophenone and chromone derivatives and their dimers from the scale-insect pathogenic fungus Orbiocrella petchii BCC 51377
AU - Isaka, Masahiko
AU - Palasarn, Somporn
AU - Choowong, Wilunda
AU - Kawashima, Kyohei
AU - Mori, Seiji
AU - Mongkolsamrit, Suchada
AU - Thanakitpipattana, Donnaya
N1 - Funding Information:
Financial supported from National Center for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), Thailand, is gratefully acknowledged. Computational work at Ibaraki University was supported by Grants-in-Aid for Scientific Research (No. 18K05072 to S. M.) from JSPS , and a Grant-in-Aid for Scientific Research on Innovative Areas “Precise Formation of a Catalyst Having a Specified Field for Use in Extremely Difficult Substrate Conversion Reactions” from MEXT , Japan (No. 18H04233 to S. M.). The generous allotment of computation time from the Research Center for Computational Science (RCCS), the National Institutes of Natural Sciences, Japan, is also gratefully acknowledged.
Publisher Copyright:
© 2019 Elsevier Ltd
PY - 2019/11/8
Y1 - 2019/11/8
N2 - A benzophenone derivative, orbiophenone A, and its homodimer, orbiocrellone A, a chromone derivative, orbiochromone A, four benzophenone–chromone heterodimers, orbiocrellones B–E, and a benzophenone–tetrahydroxanthone dimer, ent-secalonic acid I, were isolated from cultures of the scale-insect pathogenic fungus Orbiocrella petchii BCC 51377. Their structures were elucidated by spectroscopic analyses and chemical correlations. Orbiochromone A was isolated for the first time as an optically active natural product, and its absolute configuration was determined by the ECD spectrum combined with TD-DFT calculations. Four of the dimeric compounds, orbiocrellones B–D and ent-secalonic acid I, exhibited antimalarial activity against Plasmodium falciparum K1 with IC50 values of 5.7, 5.6, 14, and 5.5 μM, respectively.
AB - A benzophenone derivative, orbiophenone A, and its homodimer, orbiocrellone A, a chromone derivative, orbiochromone A, four benzophenone–chromone heterodimers, orbiocrellones B–E, and a benzophenone–tetrahydroxanthone dimer, ent-secalonic acid I, were isolated from cultures of the scale-insect pathogenic fungus Orbiocrella petchii BCC 51377. Their structures were elucidated by spectroscopic analyses and chemical correlations. Orbiochromone A was isolated for the first time as an optically active natural product, and its absolute configuration was determined by the ECD spectrum combined with TD-DFT calculations. Four of the dimeric compounds, orbiocrellones B–D and ent-secalonic acid I, exhibited antimalarial activity against Plasmodium falciparum K1 with IC50 values of 5.7, 5.6, 14, and 5.5 μM, respectively.
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U2 - 10.1016/j.tet.2019.130646
DO - 10.1016/j.tet.2019.130646
M3 - Article
AN - SCOPUS:85072997329
SN - 0040-4020
VL - 75
JO - Tetrahedron
JF - Tetrahedron
IS - 45
M1 - 130646
ER -