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Xanthanolide-type sesquiterpenoids are a diverse family of natural products isolated primarily from the genus Xanthium (Compositae). The intriguing molecular architectures and biological profiles of these natural products have rendered them attractive targets for total synthesis. This focus review aims to provide an up-to-date summary of progress in the chemical synthesis of xanthanolide-type sesquiterpenoids. Different synthetic strategies to form 5/7-cis- and 5/7-trans-bicyclic xanthanolides are presented in chronological order, with an emphasis on the key elements used to forge the characteristic 5/7-bicyclic cores of the targets. Recent advances in the total syntheses of structurally more complicated polycyclic and dimeric xanthanolides are also discussed.
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http://dx.doi.org/10.1002/asia.201900040 | DOI Listing |
Org Lett
May 2025
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Main University Campus, 54124 Thessaloniki, Greece.
The biosynthetic pathways leading to pseudoguaianolides and seco-guaianolides remain unclear. In this work, we demonstrate that highly oxidized 8,12-guaianolides serve as unprecedented precursors, enabling chemoselective, one-step access to pseudoguaianolide, seco-guaianolide, and xanthanolide-type sesquiterpenoids. Key mechanistic insights reveal the pivotal role of peroxide substituents on the guaianolide core and stereoelectronic factors in controlling reaction outcomes.
View Article and Find Full Text PDFPlant J
January 2025
Shanghai Key Laboratory of Bio-Energy Crops, Synthetic Biology Research Center, School of Life Sciences, Shanghai University, Shanghai, 200444, China.
Phytochemistry
April 2023
School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210023, PR China. Electronic address:
The traditional Chinese medicine Xanthium sibiricum Patrin ex Widder is used to treat wind-cold headache, nasal congestion, nasal discharge, allergic rhinitis, sinusitis, urticaria, and arthritis. Our previous studies found that sesquiterpene lactones, the main bioactive constituents of X. sibiricum, relieved airway inflammation in an asthma mouse model.
View Article and Find Full Text PDFChem Asian J
June 2019
School of Pharmaceutical Sciences, MOE Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology, Tsinghua University, Beijing, 100084, China.
Xanthanolide-type sesquiterpenoids are a diverse family of natural products isolated primarily from the genus Xanthium (Compositae). The intriguing molecular architectures and biological profiles of these natural products have rendered them attractive targets for total synthesis. This focus review aims to provide an up-to-date summary of progress in the chemical synthesis of xanthanolide-type sesquiterpenoids.
View Article and Find Full Text PDFPlanta Med
May 2013
Key Laboratory of Mountain Ecological Restoration and Bioresource Utilization & Ecological Restoration Biodiversity Conservation Key Laboratory of Sichuan Province, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China.
Chemical investigation of the aerial parts of Xanthium sibiricum led to the isolation of four new xanthanolide-type sesquiterpene lactones, including two xanthanolide dimers, pungiolide D (1) and pungiolide E (2), and two xanthanolide monomers, 8-epi-xanthatin-1α,5α-epoxide (3) and 1β-hydroxyl-5α-chloro-8-epi-xanthatin (4), together with four known compounds, pungiolide A (5), 8-epi-xanthatin-1β,5β-epoxide (6), xanthatin (7), and 11α,13-dihydro-8-epi-xanthatin (8). The structures of these compounds were elucidated on the basis of spectroscopic data analysis. Pungiolide D (1) displayed an unusual structure featuring a 5/5/6-fused tricyclic system in the unit B.
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