Four rare polycyclic spiro lignans (1-4) and four new biphenyl tetrahydrofuranone lignans (5-8) were isolated from the whole plant of Gymnotheca involucrata. The structures of the new compounds were elucidated on the basis of detailed spectroscopic analysis and the absolute configuration of 1 was confirmed by single crystal X-ray diffraction. Bioassay results showed that compounds 2 and 6 exhibited weak antifungal activity against Uromyces viciae-fabae at 100 ppm in leaf-disc assays, while compound 3 demonstrated moderate insecticidal activity against Diabrotica balteata at 500 ppm in an artificial diet assay.
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http://dx.doi.org/10.1055/s-0042-100915 | DOI Listing |
J Am Chem Soc
December 2024
Department of Chemistry and Biochemistry, University of South Carolina, Columbia, South Carolina 29208, United States.
Discovery of cancer immunogenic chemotherapeutics represents an emerging, highly promising direction for cancer treatment that uses a chemical drug to achieve the efficacy of both chemotherapy and immunotherapy. Herein, we report a high-throughput screening platform and the subsequent discovery of a new class of cancer immunogenic chemotherapeutic leads. Our platform integrates informatics-based activity metabolomics for the rapid identification of microbial natural products with both novel structures and potent activities.
View Article and Find Full Text PDFOrg Lett
December 2024
State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
A bioinspired alkylation dearomatization reaction was developed to construct the 5/6/6 fused-spiro tricyclic core framework and spiro-quaternary carbon chiral center. The usage of this approach for assembling these natural products of spirocyclic polycyclic polyprenylated acylphloroglucinols with an octahydrospiro-[cyclohexan-1,5'-indene] core is demonstrated by the first asymmetric total synthesis of highly oxidized hyperbeanol A.
View Article and Find Full Text PDFMolecules
November 2024
Sichuan Provincial Key Laboratory for Structural Optimization and Application of Functional Molecules, College of Chemistry and Life Science, Chengdu Normal University, Chengdu 611130, China.
We report a step-economic strategy for the direct synthesis of novel polycyclic -heterocycle-fused naphthoquinones by merging intramolecular oxidative coupling and cascade [4 + 2] cycloaddition. In the protocol, mechanistic investigations suggest that the cascade reaction involves the intermediate spiro polycyclic -heterocycles and [4 + 2] cycloaddition processes. This protocol is featured with moderate to excellent yields, wide substrate scope, and divergent structures of products.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun, 130012, P. R. China.
Incorporation of heteroatoms and/or non-hexagonal rings into polycyclic aromatic hydrocarbons (PAHs) can alter their intrinsic structures and physical properties. However, it is challenging to construct PAHs featuring boron/carbon composition and non-hexagonal combination. Herein, we disclose the selective synthesis of spiro-type and pentagon/heptagon-containing boron-doped polycyclic π-systems by the Scholl reaction.
View Article and Find Full Text PDFDiscovery of cancer immunogenic chemotherapeutics represents an emerging, highly promising direction for cancer treatment that uses a chemical drug to achieve the efficacy of both chemotherapy and immunotherapy. Herein we report a high-throughput screening platform and the subsequent discovery of a new class of cancer immunogenic chemotherapeutic leads. Our platform integrates informatics-based activity metabolomics for rapid identification of microbial natural products with both novel structures and potent activities.
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