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A pair of new clerodane diterpenoid epimers, 3-methoxyl-teucvin () and 3-methoxyl-teucvin (), were isolated from the Roots of Their structures were completely established on the basis of spectroscopic methods, and the absolute configurations were determined by analysis of electronic circular dichroism (ECD) spectroscopy and X-ray diffraction analysis. Compounds and exhibited anti-inflammatory activities with IC values of 0.82 and 0.54 μM, respectively, while the IC value of dexamethasone as a positive control was found to be 0.14 μM.
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http://dx.doi.org/10.1080/14786419.2019.1601193 | DOI Listing |
Chem Biodivers
May 2025
State Key Laboratory of Discovery and Utilization of Functional Components in Traditional Chinese Medicine & School of Pharmaceutical Sciences, Guizhou Medical University, Gui-an New District, Guizhou, China.
Phytochemistry investigation of Euphorbia helioscopia led to the isolation of 22 diterpenoids, including five lathyranes, 11 jatrophanes, and six other types. Among them, eupholine A and B (1 and 2) are a pair of previously undescribed C-6' lathyrane epimers. The chemical structures of 1-22 were elucidated using spectral data analysis, and the absolute configurations of 1 together with another jatrophane diterpenoid (3) were determined by X-ray single-crystal diffraction techniques.
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August 2025
Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán (UNT), San Miguel de Tucuman, Argentina.
Two new labdane diterpenes, (4S,5R,10S,13S)-19-acetoxy-7-oxo-labd-8(9)-en-15-oic acid-15-methyl ester (1) and (4R,5R,10S,13S)-19-acetoxy-7-oxo-labd-8(9)-en-15-oic acid-15-methyl ester (2), along with two methyl ester derivatives of the known acid compounds, (4R,5S,9S,10R,13S)-ent-7-labden-17-acetoxy-18-hydroxy-15-oic acid (3), and (3R,5S,9S,10S,13S)-ent-7-labden-17-acetoxy-3-α-hydroxy-15-oic acid (4), were obtained from Grindelia puberula Hook & Arn, collected in northern Argentina. Their structures and absolute configurations were elucidated based on one- and two-dimensional nuclear magnetic resonance spectroscopy, mass spectrometry, and circular dichroism analysis. The CHCl sub-extract obtained from the aerial parts of this species, along with the pure compounds, were evaluated for antifungal activity against Botrytis cinerea, a widespread necrotrophic fungal pathogen responsible for significant economic losses worldwide.
View Article and Find Full Text PDFBioorg Chem
May 2025
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of Pharmacodynamic Substances Research & Translational Medicine of Immune Diseases of Shenyang, Shenyang Pharmaceutical University, Shenyang 110016, PR China; Key Laboratory of
Renal fibrosis is marker and common pathway of progressive chronic kidney disease (CKD), eventually leading to renal dysfunction. So far, there is still a lack of secure drugs and effective therapeutic strategies. Caesalpinia mimosoides is an edible Dai folk medicinal plant and exhibits good effect on inducing diuresis to alleviate edema, hinting that C.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Department of Medicinal Chemistry, University of Utah, 30 South 2000 East, Salt Lake City, Utah 84112, United States.
Soft corals are prolific producers of terpenoids, such as pseudopterosins. The exact biosynthetic pathway of these anti-inflammatory diterpene glycosides has eluded the scientific community for decades. Using a forward genetic approach, we have identified, cloned, and expressed the key genes involved in pseudopterosin biosynthesis.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Key Laboratory of Applied Surface and Colloid Chemistry & School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 West Chang'an Ave, Xi'an, 710119, China.
Ryanodane diterpenes are structurally complex natural products that are well-known for their high degree of oxidation and the challenges associated with synthesizing them within the terpene class. Herein, we present a two-stage synthetic strategy that draws inspiration from the broad biosynthesis of terpenes, allowing us to achieve the first chemical synthesis of garajonone, a ryanodane diterpenoid that occurs naturally at low abundance, as well as its epimer, 3-epi-garajonone. The key to this success lies in the rapid construction of the carbon framework of the target molecule by employing an early-stage palladium-catalyzed Heck/carbonylative esterification cascade annulation, followed by successive late-stage selective redox manipulation to establish the desired oxidation state of the molecule.
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