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Alterbrassicicene A (1), a fusicoccane-derived diterpenoid with an unprecedented framework, together with two known biosynthetic intermediates (2 and 3), were characterized from Alternaria brassicicola. The absolute structure of 1 was assigned by extensive spectroscopic analyses and quantum chemical calculations. Compound 1 represents a newly transformed monocyclic carbon skeleton of a highly functionalized diterpenoid bearing unique dihydro-2(3 H)-furanone and 2-cyclopenten-1-one motifs. Compound 1 was the first fusicoccane-derived diterpenoid functioning as a potent PPAR-γ agonist (EC = 744.1 nM).
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http://dx.doi.org/10.1021/acs.orglett.8b03553 | DOI Listing |
Bioorg Chem
July 2020
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, People's Republic of China. Electronic address:
Fusicoccane-derived diterpenoids bearing a unique bridgehead double-bond-containing tricyclo[9.2.1.
View Article and Find Full Text PDFOrg Lett
October 2019
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College , Huazhong University of Science and Technology, Wuhan 430030 , P. R. China.
Alterbrassinoids A-D (-), the first examples of fusicoccane-derived diterpenoid dimers furnished by forming an undescribed C-12-C-18' linkage, were isolated from modified cultures of . Compounds and represent unprecedented heterodimers, whereas and represent unprecedented homodimers, and also features an undescribed anhydride motif. Their structures were assigned via spectroscopic methods, electronic circular dichroism calculations, and single-crystal X-ray diffraction.
View Article and Find Full Text PDFAlterbrassicicene A (1), a fusicoccane-derived diterpenoid with an unprecedented framework, together with two known biosynthetic intermediates (2 and 3), were characterized from Alternaria brassicicola. The absolute structure of 1 was assigned by extensive spectroscopic analyses and quantum chemical calculations. Compound 1 represents a newly transformed monocyclic carbon skeleton of a highly functionalized diterpenoid bearing unique dihydro-2(3 H)-furanone and 2-cyclopenten-1-one motifs.
View Article and Find Full Text PDFThe structure-stability relationships of 1-6 were investigated to show that 1 converted to 5 via a kinetic, solution-mediated autoxidation. In addition, alterbrassicene A (7), a fusicoccane-derived diterpenoid bearing an unprecedented 5/9/4-fused carbocyclic skeleton with a rare fused 2-cyclobuten-1-one motif, was characterized from Alternaria brassicicola. Its absolute structure was elucidated by spectroscopic analyses and quantum chemical calculations.
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