Six new cyathane diterpenoids, cyahookerins A-F (-), as well as nine known analogues (-), were isolated from the liquid culture of the basidiomycete . Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HRESIMS, and ECD), and the absolute configurations of compounds and were determined by single-crystal X-ray crystallography. Compounds and represent the first unusual cyathane acetals featuring a dioxolane ring. Compounds - displayed differential nerve growth factor-induced neurite outgrowth-promoting activity in PC-12 cells at concentrations of 10 μM. In addition, cyahookerin B (), cyathin E (), cyathin B (), and cyathin Q () showed significant nitric oxide production inhibition in Lipopolysaccharide (LPS)-activated BV-2 microglial cells with IC values of 12.0, 6.9, 10.9, and 9.1 μM, respectively. Similar binding modes of the four compounds were indicated by molecular-docking studies, and structure-activity relationships are discussed.
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http://dx.doi.org/10.1021/acs.jnatprod.9b00091 | DOI Listing |
J Am Chem Soc
September 2024
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.
A powerful Pt-catalyzed asymmetric diboration/desymmetric double-allylboration cascade reaction has been developed for the construction of synthetically useful, densely functionalized hydrindanes with five stereocenters, including three quaternary ones, in good yields and excellent enantiomeric excess (ee) values within a single synthetic operation. A unified strategy utilizing this key tandem methodology enabled the concise asymmetric total synthesis of cyathane diterpene (-)-Cyathin B in 14 steps from commercially available starting materials, thereby demonstrating its remarkable potential in the synthesis of hydrindane-containing natural products and pharmaceuticals.
View Article and Find Full Text PDFNat Prod Res
December 2024
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling, China.
Two previously undescribed natural cyathane diterpenoids Me-dentifragilin A () and Epi-neocyathin O (), and three known cyathane diterpenoids -, cyathin O, neocyathin P, and cyathin I, were isolated from the rice medium of the CBPFE A06. Their structures were established by NMR spectra, and HR-ESI-MS. Compounds - displayed encouraging neurotrophic activity in PC-12 cells at doses of 5 µM.
View Article and Find Full Text PDFPhytochemistry
January 2022
Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China. Electronic address:
Eight undescribed cyathane diterpenoids, representative specialised metabolites of the genus Cyathus, named cyathins Q-X, along with five known congeners, were isolated from the liquid fermentation of Cyathus africanus. Their structures and absolute configurations were elucidated by integrating NMR spectroscopic analyses, electronic circular dichroism (ECD) calculations, and X-ray diffraction. Reasonable correction to the C-12 configuration of cyathin I was corroborated by the crystal data.
View Article and Find Full Text PDFPharmacol Res
September 2020
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, People's Republic of China.
The presence of a fused 5/6/7 tricyclic core characterizes the group of cyathane diterpene natural products, that include more than 170 compounds, isolated from fungi such as Cyathus africanus and Hericium erinaceus. These compounds have a common biosynthetic precursor (cyatha-3,12-diene) and can be produced bio- or hemi-synthetically, or via total syntheses. Cyathane diterpenes display a range of pharmacological properties, including anti-inflammatory (possibly through binding to the iNOS protein) and neuroprotective effects.
View Article and Find Full Text PDFJ Nat Prod
June 2019
Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Chemistry & Pharmacy, Northwest A&F University, Yangling 712100, Shaanxi, People's Republic of China.
Six new cyathane diterpenoids, cyahookerins A-F (-), as well as nine known analogues (-), were isolated from the liquid culture of the basidiomycete . Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HRESIMS, and ECD), and the absolute configurations of compounds and were determined by single-crystal X-ray crystallography. Compounds and represent the first unusual cyathane acetals featuring a dioxolane ring.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!