This painting, a small one if we compare it to the majority of the orders for the island of Madeira, came from the Madalena do Mar Church on the south coast of the island. The origins of the construction of the church date from the years 1454-1457, which correspond to the arrival in Funchal of the mysterious figure of Henrique Alemão (Henry, the German). The first and second concession of lands in this region were given under the name of the Knight of Saint Catherine, by Prince Henry, the Navigator.
An oral tradition that has not been cleared up by any documentation says that this was the Polish king, Ladislaw III, who took refuge in Madeira at the end of a pilgrimage he made to the Holy Land after the disastrous battle of Varna in 1444, in which the Christians under his command were defeated by the Turks. Taken in by D. Afonso V, he was recommended to João Gonçalves Zarco, who, treating him with deference, respected his wish for anonymity. He married a woman from the Algarve, named Senhorinha Anes, with whom he had two sons. Called to the court by the king, he died in a landslide in the area of Cabo Girão, on the island of Madeira. Being especially devoted to Saint Catherine of Mount Sinai, he ordered the first chapel to be built at Madalena do Mar, under the evocation of Saint Catherine or Saint Mary Magdalene.
We have a painting which depicts the Encounter of St. Joachim and St. Ann, next to the Golden Gate, having in the background the Announcement of the Angel to St. Joachim, representing the immaculate conception of Mary. Note, for example, the similarity of the theme with that of a painting of the Retable of the Cathedral of Evora, a work attributed to the circle of Gérard David.
The chromatic contrasts, as well as the features of the faces of the figures, or even the detailed treatment of the clothing, are reasons that point to a proximity with the panel of the Adoration of the Kings, attributed to the so-called Master of the Adoration of Machico¹, a painter who was a painter active in Antwerp in the last decades of the 15th century and the early 16th century, being influenced by Joos van Cleve, as well as the master of 1518, already identified as Jan van Dornicke, by Jan de Beer, Patenier and Metsys.

¹ Arte Flamenga, Museu de Arte Sacra do Funchal, Luiza Clode e Fernando António Baptista Pereira, EDICARTE, 1997, p. 56.