It is one of the most important paintings by Antonello da Messina, dated 1473.
The polyptych was commissioned to the artist by the Nuns of the Church of “San Gregorio” in Messina and bears the inscription “Antonellus messanensis me pinxit” and the coat of arms of the Abbess Fabia Cirino.
Originally the tables were united by a carved and gilded frame in late Gothic style, which was perhaps removed already in the sixteenth century along with the carpentry to be reassembled at the beginning of the nineteenth century, after a clumsy restoration in the Museo Civico Peloritano.
The work is in a bad state of preservation because of very serious events: in the 16th century one of the six panels was lost, in 1842 it was cleaned with abrasive materials and in 1908 the rain that hit Messina after the earthquake caused the loss of large portions of the Virgin’s and St Gregorio’s mantles.
The work was partially restored between 1912-1914 by Luigi Cavenaghi in Milan, who traced the perimeter of some sections of the figure of St. Gregory. In 1941 the Central Institute of Restoration removed the additions of Cavenaghi, while in 1979 the painting with the Announcing Angel was restored by Ernesto Geraci, who completed the restoration of the remaining parts between 1996-2006.
The painting with “San Gregorio il Grande” is part of the five panels of the polyptych of San Gregorio, divided into two levels. The image is depicted in the lower left panel, while on the opposite side is that of Saint Benedict. The Benedictine nuns wanted in this way to express their devotion to the two saints connected to their monastic life: Saint Benedict, founder of the order, and Saint Gregory of the monastery. The central icon is that of the madonna on the throne with baby Jesus.

In the polyptych the traditional gold-colored background merges with important innovations like the unification of the space of the panels evident in the gray of the steps at the base of the throne that encroach on the side panels, use of fat color learned from Flemish and Catalan painters active in the Kingdom of Naples, intense psychological characterization of the characters, clear use of light and perspective that recalls the art of Piero della Francesca, a famous painter of the Italian Renaissance.
The attention to the details is evident in the cherries shining like gems that the Child takes from his mother’s hands and in the rosary beads at the Virgin’s feet.
The significance of the fruits in the Child’s hands refers to original sin (the apple) and the Passion (the cherries as red as blood).
In addition, the Child has a red coral pendant around his neck, an ancient good luck charm for children, which is also found in the works of Piero della Francesca and other 15th century artists.
The side panels (125 × 63 cm) depict the figures of St Gregory on the left and St. Benedict on the right, who converge towards the Marian group and advance towards the viewer.
In fact, the feet of the saints that “protrude” toward the viewer beyond the edge of the step represent illusionistic details that derive from the spatial research of Mantegna, a famous Renaissance painter from northern Italy.
In the upper register the middle panel is missing, where perhaps the Pietà or the Deposition of Christ was represented.
In the two side compartments (top left 65 × 62 cm and top right 65 × 55 cm) emerge the Announcing Angel on the left and the Announced Virgin on the right.
The white and red roses of the crown, which two little angels place on the Virgin’s head, also have symbolic meanings and refer to the Virgin’s purity and Christ’s martyrdom, respectively.
The offering hand of the Virgin is the center of the entire composition and the corolla-like opening of the fingers and the bending of the thumb suggest a rotating movement that breaks the static nature of the scene, involving the viewer.
The gesture also binds perfectly with that of the Child, representing the two figures in an affectionate mother-child dialogue, both wrapped in the same cloak.
