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.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.joc.0c00637DOI Listing

Publication Analysis

Top Keywords

tricyclo-[4411] dodecane
8
dodecane skeleton
8
acylphloroglucinol derivatives
4
derivatives tricyclo-[4411]
4
skeleton fruits
4
fruits novel
4
novel polycyclic
4
polycyclic polyprenylated
4
polyprenylated acylphloroglucinols
4
acylphloroglucinols ppaps
4

Similar Publications

Proliferacorins A-M: Thirteen undescribed acorane sesquiterpenoids isolated from the fungus Fusarium proliferatum.

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 PDF

Discovery of the Caged-Vibsane Norditerpenoids with Unprecedented Chemical Architectures and Exploration of Their Various Acid Tolerances.

J 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 PDF

Eugenilones A-N: sesquiterpenoids from the fruits of Eugenia uniflora.

Phytochemistry

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 PDF

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 PDF

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.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!