Two novel polycyclic polyprenylated acylphloroglucinols (PPAPs), garcibractinones A () and B (), as well as three known analogues doitunggarcinones A-B (-) and garcibracteatone () were isolated from fruits. Their structures were elucidated by comprehensive spectroscopic methods and single crystal X-ray diffraction. Compounds and possess an unprecedented caged tricyclo-[4.4.1.1] dodecane skeleton, and their biosynthetic pathways are also proposed. Compounds - were tested for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW 264.7 macrophages.
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http://dx.doi.org/10.1021/acs.joc.0c00637 | DOI Listing |
Phytochemistry
May 2024
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, PR China. Electronic address:
In this study, 13 previously undescribed acorane sesquiterpenoids, namely, proliferacorins A-M, were isolated from the solid fermentation of Fusarium proliferatum. Their structures and absolute configurations were confirmed via spectroscopic analyses, quantum-chemical NMR calculations with DP4+ probability analyses, ECD calculations and comparisons, and single-crystal X-ray diffraction techniques. Proliferacorins A-E (1-5) have a 7-oxa-tricyclo[6.
View Article and Find Full Text PDFJ Org Chem
September 2023
Key Laboratory of Computational Chemistry-Based Natural Antitumor Drug Research & Development, Liaoning Province, Engineering Research Center of Natural Medicine Active Molecule Research & Development, Liaoning Province, Key Laboratory of Natural Bioactive Compounds Discovery & Modification, Shenyang, and School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, Liaoning 110016, China.
Cyclovibsanones A-D (-, respectively), featuring unprecedented caged tricyclo[5.4.1.
View Article and Find Full Text PDFPhytochemistry
July 2023
Center for Bioactive Natural Molecules and Innovative Drugs, and Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, College of Pharmacy, Jinan University, Guangzhou, 510632, PR China. Electronic address:
(+) and (-)-Eugenilones A-K, 11 pairs of undescribed enantiomeric sesquiterpenoids, together with three undescribed biogenetically related members eugenilones L-N, were discovered from the fruits of Eugenia uniflora Linn. (Myrtaceae). Structurally, eugenilones A-D were four caged sesquiterpenoids featuring 9,10-dioxatricyclo [6.
View Article and Find Full Text PDFPhytochemistry
May 2022
Tobacco Research Institute of Chinese Academy of Agricultural Sciences, Qingdao, 266101, People's Republic of China. Electronic address:
The filamentous fungi Fusarium sp. are well-known for their ability to produce abundant specialised metabolites with attractive chemical structures and bioactivities. In this study, chemical analyses of the endophyte F.
View Article and Find Full Text PDFJ Am Chem Soc
June 2021
Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.
Herein, we describe the first total synthesis of sesquiterpene penicibilaenes A and B through a "C-C/C-H" approach. In the "C-C" stage, the Rh-catalyzed "cut-and-sew" transformation between trisubstituted alkene and cyclobutanone has been employed to construct the unique tricyclo[6.3.
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