Bisabolane Sesquiterpenoids from the Plant Endophytic Fungus Paraconiothyrium brasiliense

Journal of Natural Products
Ling LiuYongsheng Che

Abstract

Brasilamides E-J (1-6), the bisabolane sesquiterpenoids with the 3-cyclohexylfuran (1 and 2) and 3-cyclohexylfuranone (3-6) skeletons, were isolated from the scale-up fermentation cultures of the plant endophytic fungus Paraconiothynium brasiliense Verkley. Although brasilamide E (1) is a known metabolite, its structure elucidation has yet to be described. The structures of 1-6 were elucidated primarily by NMR experiments. Compounds 3-6 were found to be racemic, and 3 was further separated into enantiomers 3a and 3b on a chiral HPLC column. The absolute configurations of 3a and 3b were assigned by electronic circular dichroism calculations. Compound 1 selectively inhibited the proliferation of the breast (MCF-7) and gastric (MGC) cancer cell lines, with IC50 values of 8.4 and 14.7 μM, respectively. Initial mechanistic investigation revealed that compound 1 inhibited the expression of a key energy metabolic enzyme, hexokinase II (HK2), in MCF-7 cells, which resulted in dysfunction of glucose metabolism and ATP depletion and eventually inhibited the proliferation of the breast cancer cells.

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Citations

Aug 15, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zhe GuoLing Liu
Dec 30, 2015·Phytochemistry·Supichar ChokpaiboonKhanitha Pudhom
May 1, 2018·Biotechnology Progress·Marina Arredondo-SantoyoGerardo Vázquez-Marrufo
Jan 26, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Longfang GuoLing Liu
May 31, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·De-Li ChenGuo-Xu Ma
May 15, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Li-Hua ZhangYue-Hu Pei
May 26, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Chen ZhaoYongsheng Che
May 6, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Roman O ShcherbakovMaxim G Uchuskin
Jul 3, 2021·Critical Reviews in Microbiology·Junfei WangShaohua Wu

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