ABSTRACT
Two unusual polyketide-sesquiterpene metabolites, craterodoratins T (1) and U (2), along with the known compound craterellin A (3), were isolated from the higher fungus Craterellus odoratus. The structures of isolated compounds were characterized based on nuclear magnetic resonance (NMR) and mass spectrum (MS) spectroscopic analysis, while the absolute configuration of the compounds was determined by theoretical NMR and electronic circular dichroism (ECD) calculations. Compound 1 possessed a rare structure with two aromatic groups. Compounds 1 and 3 showed immunosuppressive activity with IC50 values ranging from 5.516 to 19.953 µM.
Subject(s)
Basidiomycota , Molecular Structure , Basidiomycota/chemistry , Fungi , Magnetic Resonance Spectroscopy/methods , Circular Dichroism , Immunosuppressive AgentsABSTRACT
Eight undescribed lanostane triterpenoids, physivitrins A-H, along with four known analogues, were isolated from cultures of the fungus Physisporinus vitreus. Their structures were elucidated on the basis of extensive spectroscopic methods, in which the absolute configuration of physivitrin A was elucidated using electronic circular dichroism calculation and nuclear magnetic resonance (NMR) calculation with DP4+ analysis. Physivitrins B and C showed inhibitory activities against nitric oxide (NO) production in LPS-activated RAW264.7 macrophages with IC50 values of 7.5 and 23.5 µM, respectively. Meanwhile, proinflammatory cytokines (TNF-α, iNOS and IL-1ß) mRNA expression was also inhibited by physivitrin B significantly.
Subject(s)
Polyporales , Triterpenes , Triterpenes/chemistry , Molecular Structure , Nitric Oxide , Magnetic Resonance Spectroscopy , SteroidsABSTRACT
The unusual fused ß-lactone vibralactone was isolated from cultures of the basidiomycete Boreostereum vibrans and has been shown to significantly inhibit pancreatic lipase. In this study, a structure-based lead optimization of vibralactone resulted in three series of 104 analogs, among which compound C1 exhibited the most potent inhibition of pancreatic lipase, with an IC50 value of 14 nM. This activity is more than 3000-fold higher than that of vibralactone. The effect of compound C1 on obesity was investigated using high-fat diet (HFD)-induced C57BL/6 J obese mice. Treatment with compound C1 at a dose of 100 mg/kg significantly decreased HFD-induced obesity, primarily through the improvement of metabolic parameters, such as triglyceride levels.
ABSTRACT
Nine previously-unreported farnesylphenols, involving eight neogrifolin derivatives (1-8) and one grifolin analogue (9), together with three known compounds, were isolated from the fruiting bodies of the mushroom Albatrellus caeruleoporus. Their structures were elucidated as (S)-17-hydroxy-18,20-ene-neogrifolin (1), (S)-18,19-dihydroxyneogrifolin (2), (S)-9-hydroxy-10,22-ene-neogrifolin (3), (9S,10R)-6,10-epoxy-9-hydroxyneo grifolin (4), (9S,10R)-6,9-epoxy-10-hydroxyneogrifolin (5), (-)-13,14-dihydroxyneogrifolin (6), albatrelin G (7), albatrelin H (8), and one grifolin analogue, (S)-10-hydroxygrifolin (9), grifolin (10), neogrifolin (11), and albatrellin (12) by extensive spectroscopic analyses and chemical methods. Compounds 7 and 8 showed weak cytotoxic activity to cell lines HL-60, SMMC-7721, A-549, and MCF-7, in vitro.
ABSTRACT
Four cadinane-type sesquiterpenes and four 13-carbon γ-lactones, together with three known compounds, were isolated from cultures of the basidiomycete Trichaptum pargamenum. Their structures were elucidated on the basis of extensive spectroscopic methods. The absolute configurations of two of the cadinene type sesquiterpenes 1 and 3 were confirmed by single crystal X-ray diffractions.
Subject(s)
Lactones/isolation & purification , Sesquiterpenes/isolation & purification , Basidiomycota/chemistry , Cell Line, Tumor , Cell Survival/drug effects , Crystallography, X-Ray , Fruiting Bodies, Fungal/chemistry , Humans , Lactones/chemistry , Lactones/pharmacology , Magnetic Resonance Spectroscopy , Molecular Structure , Polycyclic Sesquiterpenes , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacologyABSTRACT
Three new compounds, named as vibralactones K-M (1-3), together with vibralactone (4) have been isolated from cultures of the Basidiomycete Boreostereum vibrans. Their structures were determined on the basis of spectroscopic evidences (1D and 2D NMR, HRMS, UV, and IR data), chemical methods and literature data. None of the compounds was cytotoxic against five human cancer cell lines and showed inhibitory activity on the pancreatic lipase.
Subject(s)
Basidiomycota/chemistry , Lactones/isolation & purification , Lipase/antagonists & inhibitors , Humans , Lactones/chemistry , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Pancreas/enzymologyABSTRACT
Three new compounds, vibranether (1), myrrhlalkyldiol (2), vibralactone H (3), together with three known compounds, 2-methyl-6-p-tolylheptane-2,3-diol (4), 2-hydroxy-2-methyl-6-p-tolylheptan-3-one (5), and vibralactone (6), were isolated from the cultures of the basidiomycete Boreostereum vibrans. Their structures were determined on the basis of spectroscopic evidences (1D and 2D NMR, HRMS, UV, and IR data), chemical methods, and the literature data. The new compounds displayed no significant cytotoxicities against five human cancer cell lines (IC50>40 µM).
Subject(s)
Basidiomycota/chemistry , Lactones/isolation & purification , Drug Screening Assays, Antitumor , Humans , Lactones/chemistry , Lactones/pharmacology , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
(±)-Guajadial B (1), an unusual humulene-based meroterpenoid, was isolated as a racemate from the leaves of Psidium guajava, collected from Vietnam. The structure of this novel secondary metabolite was established on the basis of extensive analysis of NMR spectra and confirmed by biomimetic synthesis in a domino three-component coupling reaction.
Subject(s)
Psidium/chemistry , Terpenes/chemical synthesis , Molecular Structure , Monocyclic Sesquiterpenes , Nuclear Magnetic Resonance, Biomolecular , Plant Leaves/chemistry , Sesquiterpenes/chemistry , Stereoisomerism , Terpenes/chemistry , VietnamABSTRACT
Trefolane A (1), an unprecedented skeleton with a 5/6/4 tricyclic ring system, was isolated from cultures of the basidiomycete Tremella foliacea. The structure was elucidated by means of spectroscopic methods and further confirmed by single crystal X-ray diffraction analysis. A possible biogenesis for trefolane A (1) was also proposed.
Subject(s)
Basidiomycota/chemistry , Sesquiterpenes/chemistry , Sesquiterpenes/isolation & purification , Crystallography, X-Ray , Drug Screening Assays, Antitumor , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
Four new vibralactone derivatives, named vibralactones G-J (1-4), together with vibralactone (5) have been isolated from cultures of the basidiomycete Boreostereum vibrans. The new structures were elucidated by means of spectroscopic methods.