Five pairs of optically pure meroterpenoid enantiomers (1a/1b-5a/5b) and two known compounds (6 and 7) were isolated from Rhododendron fastigiatum. Compounds 1a/1b-5a/5b were resolved from naturally scalemic mixtures by chiral HPLC. Their structures were elucidated by spectroscopic methods, X-ray crystallographic experiments, and ECD analyses. Compounds 1a/1b, 2a/2b, 3b, 4a/4b, and 5a/5b were new meroterpenoids with different polycyclic systems. Two enantiomeric pairs (2a/2b and 3a/3b), 6, and 7 exhibited inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) in vitro.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/S1875-5364(19)30119-0 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
2D Chiral Ag(I) Complexes with A-π-- and D-π--Type Dicarboxylic Acid Ligands: Presenting Significant Differences in Nonlinear Optical Responses.
Inorg Chem
January 2025
Henan Provincial Key Laboratory of Surface and Interface Science, Zhengzhou University of Light Industry, Zhengzhou 450002, P. R. China.
Three two-dimensional (2D) chiral Ag(I) complexes with formulas [Ag(L)(5-nipa)] (), [Ag(L)(5-nipa)] (), and {[Ag(L)(5-hipa)]·2HO} () were prepared through the reactions of AgO with enantiopure -monodentate N-donors (L/L) and different dicarboxylic acids bearing A (acceptor)-π-- and D (donor)-π--type structural features, where / = (-)/(+)-2-(4'-pyridyl)-4,5-pinene-pyridine, 5-Hnipa = 5-nitroisophthalic acid, and 5-Hhipa = 5-hydroxyisophthalic acid. A study of their nonlinear optical responses reveals that chiral and enantiomeric pairs with the A-π--type dicarboxylic acid ligand simultaneously display second- and third-harmonic generation (SHG and THG) responses, while chiral containing the D-π--type dicarboxylic acid ligand only exhibits a very strong THG response. The THG intensity of is 451 × α-SiO, being about 27 and 24 times larger than those of and , respectively.
View Article and Find Full Text PDFFilicinic Acid-Based Meroterpenoids with Antiproliferative Activity against Prostate Cancer PC-3 Cells from .
J Org Chem
January 2025
Department of Pharmacy, The First Affiliated Hospital, Jinan University, Guangzhou 510630, China.
Nine new structurally diverse filicinic acid-based meroterpenoids (-) with four kinds of carbon skeletons were isolated from the rhizomes of . Their structures, including the absolute configurations, were elucidated by comprehensive analysis of spectroscopic data, quantum chemical calculations, and single-crystal X-ray diffraction. Structurally, compounds - feature an unprecedented 6/6/5/6/6/6 hexacyclic system with a rare oxaspiro[4.
View Article and Find Full Text PDFAchieving Precise Control Over the Molecular Periphery of Dibenzoixenes Through Modular Synthesis.
Chemistry
December 2024
Department of Chemistry, Ulsan National Institute of Science and Technology (UNIST), 50 UNIST-gil, Ulsan, 44919, Republic of Korea.
Nanographenes and polycyclic aromatic hydrocarbons, both finite forms of graphene, are promising organic semiconducting materials because their optoelectronic and magnetic properties can be modulated through precise control of their molecular peripheries. Several atomically precise edge structures have been prepared by bottom-up synthesis; however, no systematic elucidation of these edge topologies at the molecular level has been reported. Herein, we describe rationally designed modular syntheses of isomeric dibenzoixenes with diverse molecular peripheries, including cove, zigzag, bay, fjord, and gulf structured.
View Article and Find Full Text PDFToward Rhenium-Based Circularly Polarized OLEDs Using Tailored Chiral Re(CO) Emitters.
Angew Chem Int Ed Engl
December 2024
Nikolaev Institute of Inorganic Chemistry, SB RAS, 3, Lavrentiev Ave., 630090, Novosibirsk, Russia.
Chiral rhenium(I) emitters exhibiting circularly polarized phosphorescence (CPP) are an attractive mainstay for CP organic light-emitting diodes (CP-OLEDs). However, the efficiency of such emitters is not ideal, and they have never been explored for circularly polarized electroluminescence (CPEL) applications. Here, we have tailored robust chiral Re(I) complexes with improved CPP properties, and demonstrated CPEL from rhenium emitters for the first time.
View Article and Find Full Text PDFFace-controlled chirality induction in octahedral thiacalixarene-based porous coordination cages.
Nanoscale
December 2024
Université de Strasbourg, CNRS, CMC UMR 7140, F-67000 Strasbourg, France.
Nanosized chiral octahedral M coordination cages were prepared self-assembly of sulfonylcalix[4]arene tetranuclear M(II) clusters (M = Co or Ni) with enantiomerically enriched linkers based on tris(dipyrrinato)cobalt(III) complexes, appended with peripheral carboxylic groups. Two pairs of enantiomers of cages were obtained and unambiguously characterized from a structural point of view, using single crystal X-ray diffraction. Chiral-HPLC was used to evidence the enantiomers.
View Article and Find Full Text PDFWant 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!