The absolute configuration was established as (S,S,S) by the R-factor test and by careful measurement of 197 enantiomorph-sensitive Friedel pairs of reflections. The determination also confirms the absolute stereochemistry of (-)-3-aminoquinuclidine, a compound used in the preparation of the title material. The cyclohexane/tetrahydrofuran ring fusion is cis. The quinuclidine moiety has almost perfect threefold symmetry; the front and rear halves are twisted about this axis by 15 degrees. Quinuclidine-N--H ... Cl- and amide-N--H ... Cl- hydrogen bonds link screw-dyad-related molecules along the b axis.
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http://dx.doi.org/10.1107/s0108270193000824 | DOI Listing |
J Nat Prod
January 2025
Department of Nephrology, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, People's Republic of China.
In the search for novel natural products with hepatoprotective effects against acetaminophen-induced acute liver injury, the marine-derived fungus WHUF0198 was investigated. Seventeen undescribed pyranopyridone alkaloids, aculeapyridones A-Q (-), were isolated by bioactivity-guided fractionation of an extract obtained by coculture of the WHUF0198 with the mangrove-associated fungus sp. DM27.
View Article and Find Full Text PDFJ Nat Med
January 2025
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan.
A new diterpenoid, carneadiol (1), with an unprecedented tricyclic carbon skeleton, was isolated from the culture extracts of Nocardia carnea IFM 12324. The structure of compound 1 was elucidated using spectral studies, including various NMR data. The absolute configuration of 1 was determined using X-ray crystallographic analysis with the crystalline sponge method.
View Article and Find Full Text PDFJ Nat Prod
January 2025
Department of Pharmacy, University of Salerno, Via Giovanni Paolo II 132, IT-84084 Fisciano, Salerno, Italy.
As a continuation of our pharmacognostic studies on different species growing in Türkiye, the phytochemical investigation of the roots of Hub.-Mor., a licorice species endemic to Türkiye, was carried out.
View Article and Find Full Text PDFJ Am Chem Soc
January 2025
Institute of Chemical Biology, Shenzhen Bay Laboratory, Shenzhen 518132, China.
The absolute and relative configurations of bioactive chiral molecules are typically relevant to their biological properties. It is thus highly important and desirable to construct all possible stereoisomers of a lead candidate or a given bioactive natural compound. Synergistic dual catalysis has been recognized as a reliable synthetic strategy for a variety of predictable stereodivergent transformations.
View Article and Find Full Text PDFPlanta Med
January 2025
Instituto de Química, Departamento de Productos Naturales, Universidad Nacional Autónoma de México, Mexico City, Mexico.
An approach combining enzymatic inhibition and untargeted metabolomics through molecular networking was employed to search for human recombinant full-length protein tyrosine phosphatase 1B (PTP1 B) inhibitors from a collection of 66 mangrove-associated fungal taxa. This strategy prioritized two strains (IQ-1612, section , and IQ-1620, section ) for further studies. Chemical investigation of strain IQ-1612 resulted in the isolation of a new nonanolide derivative, roseoglobuloside A (1: ), along with two known metabolites (2: and 3: ), whereas strain IQ-1620 led to the isolation of four known naphtho-γ-pyrones and one known diketopiperazine (4: -8: ).
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