On the basis of coupling constants and rotating frame nuclear Overhauser effect spectroscopy of vacidin A methoxycarbonylmethylamide, the stereochemistry of the antibiotic was established. The configuration of the aglycone was determined as (3R,7R,9R,11S,13S,15R,17S,18R,19S,21R, 36S,37R,38S). The aminosugar constituent of the antibiotic was identified as beta-(D)-mycosamine. The chiral center at C-41 remains to be assigned.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.7164/antibiotics.42.1639 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
3D QASR, Antimicrobial Activity and Molecular Docking Studies of C-14 Chiral Matrine Derivatives as Potential Antibiotics.
Chem Biodivers
January 2025
Guangxi University, School of Medicine, Xixiangtang district, 530004, Nanning, CHINA.
Antibiotic resistance is recognized as one of the top ten global public health threats, posing a significant challenge to human health. The stereochemistry of chiral molecules, alongside their specific interactions with biological targets, provides essential insights for the development of novel antibacterial agents, This study investigated the antibacterial activity of 32 previously synthesized 14-position chiral matrine derivatives. Among these derivatives, compound Q4 exhibited the strongest activity against Propionibacterium acnes, with a minimum inhibitory concentration (MIC) of 0.
View Article and Find Full Text PDFIsolation and biomimetic synthesis of acylphloroglucinol meroterpenoids as anti-breast cancer agents from .
Org Biomol Chem
January 2025
State Key Laboratory for Quality Ensurance and Sustainable Use of Dao-di Herbs, National Resource Center for Chinese Materia Medica, China Academy of Chinese Medical Sciences, Beijing, 100700, China.
Two new acylphloroglucinol-nerolidol meroterpenoids (APNMs) [(±)-1 and (±)-2], with a skeleton of mixed sesquiterpene and dimeric acylphloroglucinol biosynthetic origin, were isolated from the medicinal pteridophyte . Inspired by the proposed biosynthetic pathway, we initially completed the biomimetic syntheses of eight optically active APNMs (1-8) in a one-pot domino reaction. The structures of APNMs 1-8 including their absolute configurations were unambiguously established by a combination of NMR analysis, ECD calculations, and synthetic methods.
View Article and Find Full Text PDFThuwalamides A-E: Polychlorinated amides from the marine sponge Lamellodysidea herbacea collected from the Saudi Arabian Red Sea.
Phytochemistry
February 2025
Section of Pharmacognosy and Chemistry of Natural Products, Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, Athens, 15771, Greece. Electronic address:
Thuwalamides A-E (1, 3, 5, 6 and 8), previously undescribed polychlorinated amides, along with ten previously reported related compounds (2, 4, 7 and 9-15), were isolated from the organic extract of the marine sponge Lamellodysidea herbacea (Keller), collected off the village of Thuwal in the Red Sea at Saudi Arabia. The structures of the isolated compounds have been determined through extensive analysis of their NMR and MS data, while their absolute stereochemistry was unequivocally established via single crystal X-ray diffraction. Additionally, the absolute stereochemistry of the previously reported compounds 2 and 4, whose configuration was not determined, has also been established using single-crystal X-ray crystallographic analysis.
View Article and Find Full Text PDFThe biologically and ecologically important natural products from the Chinese sea hare Bursatella leachii: structures, stereochemistry and beyond.
Chin J Nat Med
November 2024
School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China; State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, China. Electronic address:
A novel amide alkaloid, bursatamide A (1), featuring an unprecedented propyl-hexahydronaphthalene carbon framework, was isolated from the infrequently studied sea hare Bursatella leachi, alongside a new 3-phenoxypropanenitrile alkaloid, bursatellin B (2), and twelve known compounds. The structures of 1 and 2 were elucidated through comprehensive spectroscopic data analyses, while their relative and absolute configurations (ACs) were established through total synthesis and a series of quantum chemical calculations, including calculated electronic circular dichroism (ECD) spectra, optical rotatory dispersion (ORD) methods, and DP4+ probability analyses. Bursatamide A (1) demonstrated inhibitory effects against the human pathogenic bacteria Listeria monocytogenes and Vibrio cholerae.
View Article and Find Full Text PDFThe Epiphyte sp. G2112 Produces a Large Diversity of Nobilamide Peptides That Promote Biofilm Formation in Pseudomonads and .
Biomolecules
October 2024
Department of Chemical Ecology/Biological Chemistry, University of Konstanz, Universitätsstraße 10, 78457 Konstanz, Germany.
Article Synopsis
- Isolate sp. G2112 from cucumber plants produces a variety of bioactive compounds including surfactins, iturins, fengycins, and multiple nobilamide peptides, which were characterized using advanced analytical techniques.
- Four known and fourteen novel nobilamide peptides were identified, featuring diverse acyl groups and amino acid sequences, and were shown to exist in both linear and cyclic forms.
- Testing revealed that specific nobilamides (A-3302-B, A-3302-A, and nobilamide J) demonstrated significant antibiotic activity against harmful pathogens, while promoting biofilm formation in various bacteria, highlighting the importance of a common amino acid sequence in this activity.
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!