Dietary oleuropein and its acyl derivative ameliorate inflammatory response in peritoneal macrophages from pristane-induced SLE mice via canonical and noncanonical NLRP3 inflammasomes pathway

Systemic lupus erythematosus (SLE) is a multifactorial autoimmune disease without an effective and safe treatment.

Indole type akuammiline from Vinca erecta: Crystal structure of 10-OAc-Akuammine

Single crystal X-ray diffraction has established the absolute configuration of the indole alkaloids from Vinca erecta such as akuammiline-o-acyl derivative of akuammine with a 3D stable polycyclic framework. Crystal data for C24H28N2O5: orthorhombic, space group P212121 (no. 19), a = 7.349(3) Å, b = 16.099(5) Å, c = 17.323(5) Å, V = 2049.5(12) Å3, Z = 4, T = 293(2) K, μ(CuKα) = 0.789 mm-1, Dcalc = 1.376 g/cm3, 1742 reflections measured (7.496° ≤ 2Θ ≤ 119.792°), 1742 unique (Rsigma = 0.0374) which were used in all calculations. The final R1 was 0.0608 (I > 2σ(I)) and wR2 was 0.1680 (all data). The polycyclic framework of the well-known picrinine and akuammine is compared. The ether bridges located in different positions of the framework and forming five-membered cycles do not change the conformation of the polycyclic akuammiline framework. In V. erecta alkaloids, the exomethylene fragment (C18-C19=C20-C21) of the polycyclic backbone always takes on the E-condition.

Development of the HERON Reaction: A Historical Account

This account describes the discovery and development of the HERON reaction, a reaction with special connection to the Heron Island Conferences on Reactive Intermediates and Unusual Molecules. This modern ‘named’ reaction describes an unusual rearrangement of bisheteroatom-substituted amides RCON(X)(Y) whereby the more electron deficient group, X, migrates from nitrogen to the carbonyl carbon giving an acyl derivative, RC(O)X, and Y-stabilised nitrenes. In it, the origins, mechanistic elucidation, and theoretical validation are described in more or less chronological order. Along that time line we introduce the concepts of ‘anomeric amides’, ‘amidicity’ in anomeric amides, and their role in the HERON reaction. All known versions of the reaction that have since been discovered are outlined and a basic understanding of the relative roles of reduced resonance and the anomeric driving force, both functions of the heteroatom substituents at the amide nitrogen, are quantified.

Melanocrocin, a Polyene Pigment from Melanogaster broomeianus (Basidiomycetes)

A new polyene pigment, melanocrocin, has been isolated either from fruit bodies or myce­lial cultures of the subterranean fungus Melanogaster broomeianus. The structure of the pig­ment was determined by spectroscopic methods and chemical transformations. Melanocrocin is the N-acyl derivative of ʟ-phenylalanine methyl ester with a polyolefinic carboxylic acid